---------------This is an almost true story, in that the names have been changed and a few of the locations. Other than that, this is basically what happened.-----------
It was just before my fifteenth birthday in 1997 in Portsmouth, and I decided I need a day off school, so I skipped the day. I went home and did what I really wanted to do, went into my sisters bedroom and took a few items to wear under my clothes so I could just enjoy myself. I stripped off my school uniform and put a garter belt on first, then slid the stockings up my legs, revelling in the feel of the smooth black nylon. I’d shaved in the bath last night, my legs were smooth. I’d decided to risk shaving my pubic area and just hope I could keep that hidden at school in gym as much as possible. It was always the last lesson of the day for me so I knew I could skip the shower like most did before going home. My armpits were smooth, which I was less worried about as I never wore a vest in gym, only a tee shirt. Once I’d clipped the stockings in place, I pulled on the panties, stepping into them and tucking myself back and my balls in, using the methods I’d learnt recently. I looked good down as I admired myself in the mirror. Next was the bra, and like the panties it was black. Thankfully it was February, so even though I was putting my school uniform back on, my jumper would hide it. I slipped my sisters chicken fillets in the bra, adjusted everything to give myself something that almost looked like a cleavage, then put my shirt back on.
It felt very wrong, so I went back into her room and found one of her old school uniform blouses, and it felt much better. I was already used to buttons being on the opposite side, but saw that she also had an old pair of her school trousers there as well. I’d never worn them before, but they fit and looked ok, although the lack of pockets was something that would probably take getting used to. Even though I was nervous about doing this, I wasn’t worried about getting caught. Everything looked ok, and I’d skipped school before and no one took any notice of me in my school uniform. I found a pair of her black trainers that she used to wear to school, which thankfully fit me, and I slid them on as well. She’s two years older than me and at a sixth form college, but she had her growth spurt in her last year of school so they all still fit me well.
I looked at her makeup and spare handbags, but decided against it; I didn’t feel quite that confident. I put my coat on, and went out the door, heading for the park about three miles form my home. I would often go there with my best friend when we skipped school, and it felt like a good idea today. After being there about half an hour, I need the toilet badly, so headed over to them and at the last minute undid my coat to let my boobs be more obvious and walked into the ladies. I’d been in them before, but this was the first time in daylight and when not fully dressed so again, fear caught me a bit, but I just went for it. I went in a stall, sat down to pee, clean myself up and walked out before I did my jacket back up and hoped to become invisible again.
As I walked back to near the play area and swings, I heard my name being called out. I looked around in fear thinking I’d been busted by a teacher, but it was Steve, my best friend. He ran over and told me he’d decided to skip school as well, so we went and sat on the swings, both not really sure what to do. I asked why he decided to bunk off for the day.
He said, “I just didn’t feel like it today. You?”
I told him the same, realising that for the rest of the day I was going to have to try and hide what I wearing from him, wondering if I can at least get the chicken fillets out my bra to make my boobs less obvious. After about 20 minutes he suggested we head down to beach. We just walked along, talking about this and that, no big deal and I relaxed a bit about what I was wearing, he didn’t seem to notice the trouser, blouse or what I though were the quite obvious snaps of my stockings and suspenders. It was cold enough to not have to take of my jacket and I put of his suggestion of going to his house for that reason.
As we were walking along the promenade he pointed at something on the beach and said ‘What’s that?’ As he did that he put his hand on my back to get my attention and it was directly on the clasp of the bra, but he didn’t notice it because of my coat.
We stepped onto the beach and walked over to what turned out to be a big lump of seaweed, kicked at it for a minute then he sat down in boredom. I sat on the beach next to him, keeping my hands over the garter snaps. Steve looked at me and said, “Dude, was that a bra I felt?”
I felt my world drop away from me at that point.
I went to get up and go, but he grabbed my arm. “Mate, it’s ok, I’m just asking.” I looked at him and realised I had no way out of this, and begged him not to tell anyone. “Ok, our secret.” I felt a bit more relaxed but also aware that he could say anything at anytime. I explained I just felt like trying it and how I had her chicken fillets in to see what it felt like having boobs for the day. He then said “Are you wearing her pants as well?” I think my blush answered it, but I nodded as well just in case. “No worries” he said.
The next two hours was just like every other time we’d skipped school together, but at least now I was less worried. After looking around the shops, and sitting in the park again for a bit we did what we normally did and at half one and went back to my house. We got in and I grabbed us a couple of drinks and he turned on the sega mega drive. I took my coat off; he knew I was wearing a bra and what was the point of trying to hide it? He did cop a quick feel though saying he couldn’t resist it. We played for a little bit then he turned to me and asked if he could see what I looked like in the underwear, and I told him no.
We played for a bit and he bet me on the next game that if I lost I had to show him what I was wearing. “Come on, it’s not like I’m going to tell anyone, and you’ll have to get changed soon anyway before your sister comes home.”
I felt trapped and not sure what to do. If I did or didn’t show he could still tell everyone, either way it felt like blackmail and I had no choice. I took my jumper off and he saw I was wearing a blouse as it was fitted much better than a shirt would be. I was embarrassed to hell, but in for a penny…… I slipped of the shoes and he saw my stocking covered feet. “Are they Bev’s shoes?” I nodded. His eyes went wide when he saw me unzip the trousers from the side not the front and he realised I was wearing her clothes. I slowly lowered them and then let them drop to the floor as he looked at my suspenders and stockings as I stepped out of the trousers. Then I undid the blouse and dropped it to the floor as well.
Steve looked at me and asked, “Where’s your dick?”
I replied, “It’s tucked back to make everything look smooth. I read it online.”
He asked if it was uncomfortable, and I told him I’m used to it now. “I’d better get changed” I told him, and he said why, we have at least an hour before it’s a problem. So I sat next to him in my lingerie and we played on the mega drive. It was a lot of fun actually.
After forty minutes I told him I needed to put stuff away and he looked at me and I could see he wanted to ask something. I thought he was going to ask how it all felt but he surprised me when he said, “Can I have a feel of your stockings?” I asked what he meant and he said he just wanted to run his hand up them, and as I felt like I had no choice I let him. He slowly placed his hand on my leg and gently stroked it. I have to say it caught me by surprise. I’d always loved running my hands over them, but feeling someone else do it was even better.
He stroked from my ankle to my thigh, back and forth with both hands on both legs. I could feel a stirring in my panties which scared me, but it had happened when I run my hands over my legs, so someone else doing it would have the same effect, right? Anyway, this went on for what seemed forever, but only a few seconds and I stood up to go get changed. He carried on caressing my legs and told me how good it felt. This time when he ran his hands up my legs, he kept going and went past my stocking tops and felt my skin as well.
“You’re so smooth.”
I didn’t know what to say, so just said, “Thank you.”
One of his hands went up and stroked the part of my bum that the panties had revealed when I was sitting; I’d wanted to fish the wedgie out for a while and now wished I had. As that hand went back down my leg, his other hand went up the inside of the thigh on my other leg and the feeling I got then told me I needed to stop this. I stepped back and turned to go and get changed, picking up my clothes as I left the room. I looked back to tell him to get a drink if he wanted one, but never said anything as I saw him adjust his trousers and realised he had an erection. He looked at me and just blushed.
Once everything was put away and I was back in the room with him, we carried on as if nothing had happened. My sister came home, he left shortly after and the rest of the evening was normal. I did find myself thinking about his hands running over my legs, and as a typically horny teenager, I got hard quite a few times.
The next day, I bumped into Steve just before we got to school, and again, we didn’t mention the previous day. As always, school accepted my explanation that my parents were going to call later about me being ill, but it was no big deal.
On Saturday I was at Steve’s and he finally asked me if I planned on doing it again. I said maybe, and left it at that, although I was sitting there in a pair of Bev’s panties. I kept trying to let him see them down the back of my jeans, but he never did. But I did get some news from my parents and sister that evening that I told Steve about on Monday morning.
I said, “So, on Wednesday, my parents and sister are going to look at a university for her, and won’t be back till about midnight. They’re trusting me to look after myself, and I wondered…”
“Yes. I’ll tell my folks I’m eating at yours after school.” He was as excited as I was. I told him to go home first, get out of his school clothes then come to mine. That would give me about 40 minutes to get changed and use what little make up skills I already had.
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We both walked home very quickly on Wednesday and he carried on walking as I went inside. I was stripping as soon as I got and jumped in the shower. I’d shaved and moisturised everything the night before, had picked the clothes I wanted to wear and started getting ready as quickly as I could. I sat at my sister’s vanity and powered my face as I didn’t need foundation. Next I put some eyeliner on, not very well but good enough, then a touch of eye shadow and mascara. A bit of blusher and red lipstick to finish the look off. I’d already made sure I had enough makeup remover and everything needed to be off and clean by ten pm just in case they came back early. I played about with my hair as much as could, I’d kept it as long as I could for a while, but I had no experience of styling it so I just brushed it to give it as much volume as I could when I dried it, but it wasn’t really that long enough to look how I wanted it too.
Feeling very nervous, I waited for Steve to ring the bell. When he arrived I checked it was him and opened the door, keeping myself hidden from any neighbours who might be looking. I closed the door behind him and turned to face him. “Wow, you look good” he said. I smiled and thanked him, and he waited for me to walk past him to lead the way. I realised he was looking at my bum so I worked it a little bit. I was wearing a red, sleeveless dress, with a skater skirt, and underneath almost the same lingerie I wore the other day, except this time I wore a thong. On my feet I had a pair of four-inch heels on, which helped me swing my hips a bit.
We went into the living room, and he asked a few questions about what I was wearing with me saying I didn’t want to feel quite as exposed as the other day. He asked if I was wearing stocking again and I gave him a quick flash and we sat down to play the mega drive. Other than what I was wearing it was just like the other day. I did sit with my legs together and often crossed. When I wanted to beat him at a game, I would scoot forward and flash my stock tops to distract him, and I was aware that I was giving him a boner. It made me feel very good to know that at least to one guy, I made an attractive girl, even if it was my best friend.
It didn’t take us long to get hungry so I put the pizza in the oven and we sat to eat it, surprisingly at the table in the kitchen. We’d never done that before. When he finished his slices, he asked if he could feel my stockings again and I told him he would have to clean his hands first. He ran to the sink and for the first time I felt power over him. If he wanted to keep stroking my legs he would have to keep my secret. I poured myself another glass of soda and watched him dry his hands as I decided I wanted to keep some of the power in this.
He sat down and reached out for my legs, but I stood up as he touched them. I turned around, smoothed out my skirt and sat on his lap. ”I thought this would be easier”, I told him. He put one hand on my hip, and the other on my crossed leg. He was stroking them and I forced him to talk about schoolwork as he did it. I wanted to try and distract him, and myself from what I was feeling in my thong, and also feeling from his trousers. I could feel him pressed against me, so I uncrossed my legs and wiggled about telling him I wanted to get comfortable. I could feel his erection pressing against my bum, and I rested my head on his shoulder as he carried on stroking my legs.
They had fallen slightly apart when I moved so now he was stroking the inside of my thigh as well as right up under my skirt, above my stocking tops. “I’ve always wanted to do this to a girl.” He told me. ‘Do what?” I asked him, looking into his eyes. “Run my hands along her legs and under her skirt when she’s sitting on my lap.” He told me.
I’d never felt more like a girl in my life, and was loving every second of this. I knew we were in dangerous territory, but I also wasn’t’ afraid. Still looking in his eyes, I said, “Whenever we get the chance, I’ll be the girl who lets you do this.” I meant it, I really did, plus I felt power, girl power and wanted to enjoy the feeling. I stood up and he kept his hand under my skirt and on my inner thigh, above the stocking and he knew to keep stroking with his thumb. I bent down and gave him a kiss on the cheek and he didn’t pull away.
“Come on, we’ve got plenty of time. Lets watch a film.” I said.
We went back into the living room and he put a video on, I can’t even remember what it was as I put my legs over him when we sat on the two seater sofa together. He kept stroking my legs through the film, often as high as my hips and once he ran a finger over the front of my thong. I was stroking him with my legs as we sat there, slowly moving them so he got some extra fun from it. Every so often I felt that he was still hard, so I teased him by resting my right foot on his leg, with my toe resting on it, tickling him.
After ten minutes of this torture for both of us, he said he needed to go the bathroom, so I made him pick my legs up and swing them out to get up. When he put them down I tried to make myself look as sexy and seductive as possible, and told him to hurry back. In reality I probability looked really nervous. As soon as he was out of the room, I jumped up and lowered my thong so I could rearrange my tuck as it was getting uncomfortable down there. After about five minutes I wondered where we was and hoped he hadn’t left without me hearing. I went to the bathroom and was about to knock when I could hear him in there. I realised he was jacking off, so I carefully unlocked the door with a coin, waited a few seconds and then opened it.
My timing was perfect as he came as I opened the door. He stood there with his erection in his hand, shooting cum in my direction and unable to hide it. Thankfully it missed me, but it was close. He was trying to cover up, but I just stepped in and grabbed some tissue as I started to clean his cum up from the floor. While kneeling down looking up at him, I asked “was that because of me?” He nodded. I dropped the tissue in the toilet and then gently took his hands and with fresh tissues cleaned the cum from his hands. Then, feeling the girl power rushing through me, I took his penis in my hands and cleaned that of cum, squeezing the last drops out.
I stood back and looked at him and said “Thank you, that’s the best compliment you could have given me.” And gave him another peck of the cheek before walking back downstairs. I wondered if I had gone to far, but he came back and sat down to watch the film. I put my legs over him and he stroked my legs again, a bit less than before, but still doing it. About six o’clock, I decided I’d had enough of this and turned to snuggle up to him and he put his arm around me, stroking my arm with his thumb.
“Thank you for tonight, I’m really enjoying it.” I told him. He looked me in the eye and said “me too.” Then he kissed me. On the lips.
It wasn’t a long kiss, or full of passion or tongue, but it was a kiss and he started it. I gave him a kiss back and cuddled up to him again. This was new, and I wasn’t sure what it would me. Without looking at him, I asked, “Did it bother you when I held your penis to clean it?” He answered straight away. “No. Once you saw me cum and the surprise of it, I realised it was no big deal. You were being my girlfriend and helping me.” I looked up at him, and put my hand on his semi erect dick. “I can help you again if you like?” I said. He nodded, and I slowly unzipped him. It was hard to do with one hand, so I moved into a kneeling position next to him, and undid his belt and jeans.
Now I had a new problem, I was hard trying to pull them down from here, even when he lifted his hips, so I moved to kneel in front of him as I pulled his jeans off and started to stroke him. He was hard in my hand for the first time. This was a new feeling to me, plus he was bigger than me. He opened his legs to let me get closer as I knelt between them, and I realised I was in the perfect position to give him a blowjob. I thought, should I shouldn’t I? I was enjoying stroking him and watching his face when I saw the first drop of precum on the tip and I thought, in for a penny…..
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The next day at school I felt a little awkward when I saw him but he treated me differently to how he treated the other me, his girlfriend Amy. To him I was a different person, but to me I felt the same, Amy was me as well, just dressed differently. On Friday at school I decided to take a risk and I wore the thong under my trousers. When we went into town lunchtime, we were sitting watching people go past and I asked if he thought that girl was wearing the same thong as me. He looked at me in surprise and said, ‘Really?” I nodded walked away and he followed. When no one was around, he put his hand on my bum and knew I was telling the truth. We walked home together after school and he came into mine and I quickly put a bra on and made out with him, swallowed a load arranged to see him the next day.
When he came round and we headed out on Saturday morning with no idea where we were going, he told me he had a surprise for me. He opened up his bag and inside was a Styrofoam head. I looked at him confused and he said look inside again. I saw some hair and he quickly explained. His mum had had alopecia when he was born so had a wig. She threw it out the yesterday and he rescued it. Now you’ll look even better. That evening in my room I tried it on and it was a long wavy blonde wig and it felt like real hair, and more importantly it I could see how it would make me look more like a real girl. This was a big deal and must have been very expensive.
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Tuesday afternoon was a non school day because of some weird religious thing, so we went back to mine and I wore the wig for him. I could tell it made him hard immediately and as we had more time, things moved a bit faster than I expected it to. Today I had only worn lingerie and the wig for him, and we spent the whole time in my room, kissing and making out. I swallowed his cum once already and was just kissing him and playing with his dick when he rolled me over onto my back. I’d been in this position with him before, but this was the first time he’d been naked and his erection with pressing against my stomach.
With one hand stroking my leg, he moved it up and for the first time cupped and felt me as if I had a vagina. His finger was pushing and stroking me through the panties as if he was trying to finger me. I was so turned on I was pushing my hips into his hand as his penis was dripping pre cum onto my stomach. I barely noticed when he moved my panties to one side and a finger was playing at my hole, only that I was loving every second of this. Then it was in me, and I loved it. I’d fingered myself in the bath, but like stroking my stocking covered legs, this was better. I wasn’t in control of the movement I was feeling inside me. I reached down and stroked his penis as he fingered me and I kissed my boyfriend. This was the first time I thought of him as my boyfriend rather than me as his girlfriend.
He took his finger out of me and changed position as I kept stroking him. I realised I was stroking his cock as it touched my hole. I could feel the warm slickness of his pre cum there. He whispered in my ear “I have lube.” I looked him the eye, kissed him quickly and nodded. He jumped of the bed and grabbed his bag. He had some KY jelly and was in too much a rush to open he couldn’t open it. I took it from his hands, opened it and smeared some on him. He felt even better like this and I made a mental note to try and get some of this for myself. He got back between my legs and I pulled the panties to one side again as he got in position. The lube was cold, and he slid about a bit. I reached down and guided him into me as he pushed.
Dear god, it felt amazing! I’d been using the handle of a hairbrush for a few months now, but this, this was even better. He pushed in and we kissed as he slid in and out of me. It was an amazing feeling and I realised we were both losing our virginity with each other. He didn’t last long, it was his first time, but I will always treasure it. The feeling of being spread and held open by him, how it felt as he moved into and out of me. How it twitched as he came and the feeling of warmth inside as he did so.
We lay there, locked together kissing until he slide out of by getting smaller. I missed having him in me. After cleaning up, we arranged to skip school on Friday, and made plans to do something we had only done once before with another friend from school, Michael and his girlfriend Nicola; get the train to the next town for the day.
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Friday he came to meet me and I had sorted everything I needed for the day. Under my school clothes I was wearing the lingerie and thong. My coat was gender neutral and looked ok with what I planned to wear. My bag had a skirt, shoes, the wig, make up, hairbrush and another bag. At the station we got our tickets and I knew I had exactly 30 minutes to do what I had planned. When we got on the train, Steve got on a different carriage to me, and as soon as it pulled out the station I went to the toilet. The trains were different then and the toilets were out of sight of everyone else. I opened my bag and started stripping to my lingerie while keeping the jumper on as it was my sisters and pulled the skirt on. The skirt was a short A line one, and I was already wearing over the knee socks. I pulled the ankle boots with two-inch heels on and zipped them up. I slipped a necklace on and took the wig out, brushing it as best I could. The train pulled into the next station and I looked through the little circle to see which one. I still had plenty of time. Slipping on the wig, I adjusted it and made sure it looked good as the train started to move.
The next step was more tricky in a train, so I took the chance to put my boy clothes in the bag, and then put them in the other bag, a big shoulder one that my sister used when she was carrying everything and the kitchen sink. My money was already in the purse inside it, and I moved my return train ticket to it as well. I started to put the foundation power on as while the moving train I didn’t need to worry too much about the shaking. We pulled into the next station and this was my chance; I quickly put mascara and eye shadow on (I’d put the eyeliner on in the station toilet, it was a risk, but it seemed a better option). I finished the last part of mascara as the train started moving, and the blusher went on next as I waited for the next station. As pulled in, I started to put lipstick on and had it done in plenty of time.
Before the train pulled out, I opened the door and walked along the train like someone who had just got on. I saw Steve sitting and waiting for me so I went and sat down with him, smoothing my skirt out as I sat. I smiled at him as I crossed my legs while he was checking me out. I felt truly amazing. When we arrived at the town station, the first thing I did was go to the ladies to check my makeup, which meant I had to go over the footbridge to the other platform. I did a few touch ups, and then went back out to see Steve. He smiled and said when I went up the stairs a few men looked to watch me and look up my skirt.
The rest of the day was us walking around as a couple, holding hands and kissing. We looked in HMV, and I looked in a few clothes stores. I brought a pair of tights in case I felt like I needed to cover up later. No one did a double take when I was walking around, other than to check me out, when I spoke to people in shops no one took me for anything other than a girl. The air up my skirt as always felt amazing and wearing a short skirt felt good, although I was pleased it was lined even if it was short. In Top Shop I was coming out the changing rooms and as I hung up the clothes I tried on, thinking about what we could do for lunch, I turned around and there was Nicola. I tried to ignore her, but she noticed me as I stopped for a second when I saw her. She looked at me, then tilted her head to look and think and then her eyes went wide. I was trying not to panic, but she took my arm and led me to one side away from anyone.
“Oh my god! Is that really you D____?” She asked me. I was trying not to hyperventilate as I told her it was. I quickly gave her some details and what was happening, when something occurred to me. “Wait, what are you doing here?”
She told me that her and Michael skipped school as well. Now I was really panicking as I couldn’t see him. She said he was looking in a shop and would get him away from me. She left the shop first, with me promising to speak to her later to explain everything, then I walked out looking for Steve. He was talking to Michael with a look of fear on his face. Nicola took my hand and said, “Don’t worry, I’ll handle Mike.” We both walked over to them together. I smiled to Steve but I think I was as nervous as him. Michael looked at Nicola, looked at me, then at Steve and before he said anything, Nicola kissed him.
“Look honey, I bumped in Amy in the shop. Hi Steve, shall we all go to the park?”
We all followed Nicola for the short walk to the nearby park, with Michael constantly looking back at me and Nicola telling him to stop staring. In the park Nicola told him what I had told her and he was shocked, but when Nicola said she would break up with him if he did anything to hurt me, he knew he was beaten. After a bit, we got up to go and get something to eat at McDonalds, and Nicola walked with me asking, “So how long have you been dating?” I told her a bit more details, and she told me how amazing I looked which I totally loved, and we just complemented each about our looks. She offered to teach me some makeup stuff to help me, and in the ladies in McDonalds she re did my eye shadow for me.
At one o’clock, me and Steve got the train home, and I decided not to change and risk walking to my door in daylight. My confidence was sky high right now, and Nicola said she would handle Michael to keep him quiet. When we walked through the door Steve was all over me and I let him. Kissing and caressing him was amazing and he told me he’d been hard all day because of how I looked. I told him I knew as I was checking it, and every time it flagged a bit, I teased him to bring it up. Right by the door, I knelt down and gave him a very sloppy blowjob, swallowing his cum and enjoying the girl power I felt running through me as he was trapped by my mouth and the pleasure I gave him.
We went to up to my room, and as I walked in front of him up the stairs his hand was stroking my inner thigh, his thumb teasing my hole. In my room I pulled his trousers down and used my mouth to make him hard again. It didn’t take long and for the first time that we’ve had sex, he put his hand up my skirt and pulled my knickers down. My own smaller erection sprung free, making a little tent in my skirt as he kissed me and lay me down. I pulled one booted foot through a panty leg, and opened my legs for him. He already had some KY jelly in his hands and was spreading it one him as he laid on top of me and in one smooth movement entered me. It took both our breaths away.
We slowly made love in that moment, my legs wrapped around him as he slid in me, kissing and caressing me. With my feet I pushed his trousers of and he moved deeper into me. It was the first time we both came together.
We lay there embracing and kissing each other as he stayed hard inside me. “I needed that as much as you I think.” He whispered in my ear. I kissed him deeply in agreement as I wrapped my arms and legs around him to hold him tight, with my panties hanging off one ankle.
And then I heard a cough.
We both opened our eyes and looked to my open doorway and my sister was standing there.
“Errrr. Hi sis” I said.
The day of the first show we would all be excused classes and do a final full rehearsal before the whole school came in to watch us, then in the evening it was another show for parents. On the Saturday we had one final evening show which is the one people are buying tickets for and the one we had to knock it out the park. We all felt ready, but more than that, I felt happy.
On Monday morning I had a doctors appointment so was excused the first lesson. Me and mum walked in and the doctor was lovely to me. She said I looked really pretty and admired my new eyebrow shape. We were given the results from my blood tests and everything was ok, although I still hadn’t gone through puberty which explained why I looked so pretty, although I was pleased about that to be honest, I didn’t want to look like a boy again. Mum and the doctor talked about that and it was kind of hard to follow as I realised I hadn’t been listening after hearing about not going through puberty when I realised mum was talking about testosterone shots with the doc. I said, “Hang on, shouldn’t I have a say if I have them?” They both stopped and looked at me and mum asked if I had been listening. I went quiet and she looked at the doctor and said, “Girls eh, probably thinking either fashion or boys!” And they both had a little laugh at me, when the doctor then re explained everything to me. Basically, I could have them if I want to go that way, or I could have a puberty blocker seeing that I seem to want to go down the route of being a girl as they can’t give me girl hormones for a while yet. I needed to go away and think about, then come back in a week to decide.
I went quiet as I thought about this, do I say anything. The doctor sensed I wanted to say something now, but mum thought I was just scared, so the doctor finally said, “Or would you like to me to write the prescription now as you’ve already made your mind up?” I blushed and lowered my face but nodded. The doctor said I need to say it out loud, so I said it, “Yes, I would like that please.” It was explained again the risks and I was referred to something called a gender clinic, but it might be a while before I hear from them, so in the meantime we should carry on as needed. She also made it very clear to me I must not try and cut corners as it could be very dangerous for me and arranged for me to come back for my first blocker shot. On the drive to back to school, we talked a lot about what we would do now, but I just said there was no point me changing anything, the worst has already been thrown at me. We then discussed my name and making it legal so she said she would look into it but was there a middle name I might like. I looked at her and could only think of one name I could think of. “Amy Joanne.” Mum went quiet for a bit then said, “Amy Joanne, Amy Jo, AJ!” You know people will call you AJ”. I was horrified, “No they won’t! They can call me Amy! It’s my name, I picked it and you will call me it.” I practically stamped my foot in the car and mum almost had to pull over as she was laughing so much. She told me she loved me and to stop being so serious, she was here for me, and I had friends who accepted me and loved me, and I would be happy no matter who I chose to be. I told her I loved her. We arrived at school, and I went to main office to sign the book saying I had arrived and as there was only ten minutes left till the end of class I just went and waited for Nicola to finish her lesson. We walked through the school together and I almost told her about my decision, but not yet. The school would need to be formally told, then I would need to finish the show and then it was a week of half term, and I would come back as Amy and surprise everyone. I suspect that might be the worse time for me, but I was a survivor, not a victim.
Friday morning, I arrived at school but not in uniform as I would be in costume pretty much all day so I arrived in leggings but a short jumper so anyone who looked would wonder what had happened to me down there. My tuck was on point that day, and I had used some of the tape that looks like a plaster to hold me in place. Walking through the school I got the looks, but quickly caught up with my Pink Lady’s and headed to the drama studio. I had made the right choice as we were all in leggings that day, although I was wearing trainers and the girls were in uggs. We were the first to go into makeup and hair while the woodwork and art classes were rehearsing the scene changes. Miss Reeves was running about like a loon making sure everything was being done, but for us it was just so much fun and, being spoiled rotten! Sarah’s mum and dad did our hair and we were cautioned not to be too silly and be very careful during our costume changes. Once that was done, we went to get into our first costume, the big petticoats and long skirts and then waited while everyone else was having theirs done. It was now I started to feel nervous, but Miss Reeves had thought of everything as even though we were waiting, we had a photoshoot with the T Birds and our Sandy (who had never really joined in with the rest of the Pink Lady’s as she was a bit snooty, but totally focused on being a star when she left school). Walking about the school, all done up and having your photo taken is a lot of fun, and they wanted a few done during break as they wanted the other kids in the background. They were a nightmare and what should have been easy became a bit crazy and we all felt our skirts being lifted up at some point, so we all screamed a fair bit, afraid that they would see our suspenders and stockings.
We then headed back for our final dress rehearsal and Miss Reeves only had a few pointers and lots of praise. She really liked how we the Pink Lady’s worked together when we sang Look at me, I’m Sandra Dee and the T Birds were great singing Greased Lightening and really funny. The school had said they had to use different lyrics for the swear words, but they had all been rehearsing the real lyrics and I think Miss Reeves knew what they were planning. She’d had enough trouble getting in the bits about virginity and a pregnancy scare but had argued that it was a useful learning experience, so it got approved. After a light lunch for everyone, and making sure we all had water with straws for us girls, we stood backstage waiting for everyone to come in. The headmaster did a little speech, then Miss Reeves talked as they started playing the title music Grease and as soon she finished talking, the curtain went up. The T Birds were doing their opening bit, and my nerves were terrible and I was shaking but the girls hugged me and said, come on, we’re on and I walked out onto the stage and sat on the bench ready.
There were a few little errors, but it worked out really well. They laughed where they were meant to laugh (especially my opening line about wearing glasses for school and Sarah as Rizzo saying she could still my face), sometimes they sang along with us and the other pupils were really surprised when our teachers played the teachers in the show. We had been sworn to secrecy over that and they had only been able to rehearse with us here and there so when they made a mistake or forgot their lines it worked even better for us. After the show we were squealing with excitement, and I felt so tired. Miss Reeves told us that it was our nerves from earlier, so we had to take it easy, have something to eat and then we would reset for the parents show. The Parents show went well, and I will still nervous but not as bad as for the school only show. When mum drove me and Bev home afterwards, I fell asleep in the car and it was only a short a drive. I woke up very late on the Saturday and wasn’t due at school until 2pm and knew Jo needed some rest so just had a lazy day at home in leggings and fluffy socks.
For this show we had to do our own hair and makeup, which I thought was funny seeing that these are people who paid for a ticket, and they hadn’t told us if they had sold many of them. Surprisingly, when we peeked through the curtain the seats were filling up and while it wasn’t sold out, it almost was. This show everyone sang along with us and seemed to know the lines as well as we did. We were told afterwards that it was people who were big fans and do that in the cinema, which is why we sold so many tickets and they paid for all the bits that needed to be paid for. After the show we had a little party and we each were given a programme and were each signing them for each other. It was the first time I had written my name out as Amy, and I wrote it so many times it felt natural by the 30th time. Kim’s mum drove the Pink Lady’s home and we agreed to meet up on Monday in town. It was funny, most people thought I would be going back to being a boy, but they kept talking about it being a girls day out shopping so maybe they knew something I didn’t.
On Sunday when I woke up there was a card next to my bed addressed to Amy and it was from my mum and Bev saying how proud of me they were, and also £200 pounds to get myself a wardrobe and that I should maybe spend a bit at charity shops. I was so touched, and suddenly the girls day out shopping made a bit of sense. They knew this was happening, mum had arranged it with them but asked them to keep it quiet. The girls suspected Amy might be here to stay for a bit longer so when mum asked them to meet up with me. I was still tired today so I did literally nothing other than sit in front of the TV watching some awful stuff, but not bothered enough to watch anything else.
But Monday was the big day, and I selected what I would wear very carefully. I wore an old pair of flats to start the day, a short tennis skirt, a white tight tee shirt. I still had my Pink Lady’s jacket and decided to wear it, with my hair down. I picked up my bag and headed out for the bus for a quick detour. Martin and Jo were both still in their dressing gowns and Jo looked very tired. I didn’t want to spoil their time together so said I was just here to pick up my knee-high boots and Jo hugged me, said I was looking great but she needed to go back to bed as she was still tired. While I was putting them on in the living room, Martin was chatting to me and asked what my plans were. When I told him about the money for clothes, he asked what that meant, so I told him about my visit to the doctor and that the school will be told this week, but Amy is here to stay. He gave me a huge hug, which turned into a kiss, which turned into us on the floor with my legs wrapped around him and my thong across the room somewhere. We kept the noise down so Jo could sleep, but I felt my toes curl in my boots as he came inside me and I came on our stomachs. I held my skirt up as Martin cleaned my cum from me before he cleaned himself and I put my thong back on and tucked. I repaired my makeup and told him I would try and see him again over the holidays, but I expected I would be spending time with the girls and would need to meet up with Steve and talk with him about this.
Meeting up with the girls was a lot of fun, we had all worn our Pink Lady’s jackets and they showed me around the shops. I got a selection of skirts, tops some new shoes and my own ankle boots. I brought my first dresses, a couple of summer dresses and a couple of going out dresses and treated all the girls to lunch in McDonalds as they had been so nice to me, and I told them my news. None of them were surprised, they had seen it coming weeks ago they said. We arranged to meet later in the week, and I loaded up all my bags and got the bus home, feeling like a very lucky girl. Bev showed me the paper which had a review of our show from the parent’s night and it was really nice, especially what they said about Miss Reeves for putting it on. I read the article carefully as I was scared they would talk about the boy playing a girl, but there was nothing so I felt very relieved, I really didn’t want my life splashed across the front pages. I rang Steve and arranged to meet him the next day on Sunday, and went to bed feeling very happy and comfortable in myself. The next day I put on one of my new sundresses and borrowed one of Bev’s jackets heading to Steve’s. I wasn’t sure what he would say when I got there but hoped it would work out ok. He opened the door and looked at me and walked in saying nothing, leaving the door wide open for me. I shut it behind me and found him in his living room playing a game on his console.
I sat down and he asked if I wanted to play, pointing at a controller. Ok, it’s going to be like that is it?. Fine, I like this game and can kick his arse with it, so I did. When I won, I said, “I’m staying as Amy.” He looked at me and said nothing, just loading up another game. “I thought this was just you messing around.” He finally said. I told him about all the fun I’ve had, how much more comfortable I feel and I’m sorry if this makes it difficult for him but this is who I am and who I will be. He played the game saying nothing and I just sat there waiting for him to say something. He said, “I meant to tell you, I have a girlfriend now.”
Wow, I wasn’t expecting that. He never said another word, but I refused to be pushed around on this. “I’m really pleased for you. When did you get together?” And then it really did feel like a slap in the face as he started seeing her just after we started having sex together. I was his bit on the side while he cheated on her with me! But then I thought, well, I can’t even tell him that I was cheating on him, but it does make me feel a lot better about it. He told me a bit more about her, how they met and so on, and I realised that really I was just his practice girlfriend so he could get a real one. Well that’s ok, he was my practice boyfriend really and because of him I became Amy for real. I looked at him and said, “Thank you.” He played for a second and then paused the game, asking me what I meant, and I told him that if I hadn’t bumped into him that day when bunking off, I wouldn’t be sitting here as my true self. He re started the game and just said ok. I picked up the other controller and we played the game together. By the end of the day we had slowly started to return to a bit more normal friends, but there was still some awkwardness as he said I really needed to leave before his folks came home. I kissed him on the cheek and said I hope to meet his girlfriend soon and that maybe if I get a boyfriend for a double date. He looked at me and asked if I wanted a boyfriend and decided to inflate his ego a bit, “Of course I do, if nothing else I really miss getting laid and if he is half as good as you I will be very happy.” And I gave him a wink and started walking home.
I kissed him on the cheek and said I hope to meet his girlfriend soon and that maybe if I get a boyfriend for a double date. He looked at me and asked if I wanted a boyfriend and decided to inflate his ego a bit, “Of course I do, if nothing else I really miss getting laid and if he is half as good as you I will be very happy.” And I gave him a wink and started walking home.
I was heading round to Kim’s in the afternoon as we were going clubbing in the evening, and I felt a little sad about it being over with Steve but glad we could at least be friends. I put on one of my new dresses, a nice blue skater dress with my boots and made my way there, feeling a bit exposed on the short walk to meet up with the girls. We hung out a bit and I ended up wearing Jodie’s dress, while she wore Sarah’s mini skirt and cropped top. Kim’s mum gave us a lift and we joined the queue. There was a boy a couple of places in front of us and he kept looking back at me. He looked a bit familiar so I guessed he must have gone to our school but once we got inside, he came straight up to me. “Hi.” He said. I said hi back and tried to not act too freaked out he might say something about who I was, but when he started talking again I realised he wasn’t from my school. “I was really hoping to see you here again Amy.” He told me, and it all came flooding back. This was the boy I had been making out with! We chatted for a bit and found out we were from rival schools. In the club it seemed I barely spent any time with the girls as I was either dancing with James, chatting with James or making out with him. I really regretted the last one as he suggested we leave a little early to go outside and I agreed to go. I found the girls and said I would meet them outside the club when it closes and walked out with James, holding hands.
We headed over to a bench that was opposite the club, looking out to sea and, well, we didn’t chat as much as I hoped, but we did kiss a lot. The skater style skirt on the dress I was wearing meant it wasn’t long until his hand was on my hip on the inside, and I had to force myself to keep my legs together. I did manage to hold him off and when he tried to put my hand on his penis, I managed to stop it and slapped his hand when he started to pull my thong down a little, just to let him know I’m happy with this, but not going further. I told him that this is all he will get tonight, and realised I was setting myself up for trouble later as I was implying he will get more later. While we were kissing, I was keeping an eye on the club over his shoulder to see when people started to come out and when they did I broke away from him saying I will need to meet my friends. “Do you want to go to McDonald’s tomorrow?” He asked me. Wow, a boy has just asked me on a date, this is something very new to me, but I found myself agreeing to meet him at 11 in town, just as I saw the girls come out looking for me. I stood up and he reluctantly got up as well, trying to hide his erection, so I gave him a quick treat by giving him a kiss and putting my hand into his trousers and rearranging him to help hide it. I felt it twitch it my hand so got out of there quickly in case it went off in my hand!
We walked back to the club, and he put his hand around my waist and that’s how the girls saw us. I gave him a quick kiss and said I will see him tomorrow and walked off with the girls, who all squealed in delight at me having a date. We went to get some chips and then waited for Kim’s mum to arrive and take us all home, who couldn’t stop laughing as we were all trying to swap clothes back to what we had started with in the back of the car without being seen by any other drivers. That night in bed I was thinking a lot about my date and what I should wear, when I realised it was less about what I would wear and more about what I would do, or more what I should do. In the morning as I was getting ready to go into town, I think I had decided. I wore a jeans skirt with a pair of trainers and black roll neck jumper and waited for him outside s store as agreed. I waited for what seemed like forever but was really only about five minutes when I noticed him waiting at the other entrance for me. He kept checking his watch, so I just stood there looking at him waiting for him to see me. Finally, he looked in my direction and a big smile broke on his face as he walked over. When he got to me I gave him a kiss on the cheek, took his offered hand and we walked towards McDonalds. He explained he thought I was late as he had been waiting since half ten, but the store has a lot of doors and we never said which one. Walking through town on a date with a boy was new, normally they only want to have sex with me in secret, but James didn’t know about me so wasn’t trying to hide me. He paid for a burger and fries for me and was very good at making me laugh. I learnt a bit more about him, his family and so on and he was definitely one of the good guys, even if he did try and pull my thong down in public while we were kissing. He is a boy after all.
When we finished we walked to the nearby park and I decided it was only fair that I told him the truth about me. I had already shown him the newspaper article about the show, but that never mentioned about my bits, and he was so nice I didn’t want to upset him. We sat on a bench and I told him the truth, kinda, that I auditioned for the play and was offered the part of Marty, even though I was born a boy and I intend to be a girl forever. He went really quiet and didn’t say much for a bit and I was very nervous he was going to beat me up. I was ready to run and wondered how fast I could pull my skirt up a bit to get away from him. Finally, he said, “You should have told me last night.” I told him I was sorry, that I got carried away and didn’t mean to hurt him. “This is a lot for me to take in, I mean, who else knows about you?” I tried to move away from him, but he was still holding my hand and didn’t let go. I told him the whole of my school knew about me being in the play and that I had spent the last two months at school as a girl already and that now most people accept me as the girl I am, but after the holidays it will be official. We sat there in silence for a bit longer, so I told him I needed to go home, and gave him my number in case he wanted to talk about it and stood up. He stood up as well and kept holding my hand. I wasn’t sure if I should let go and break the spell, so I just stood there looking at him. Finally, he asked if he could see me tomorrow. I agreed to see him again and that I would buy the McDonalds this time. He nodded and I started to move away but stopped suddenly as he was still holding my hand. I looked at him and he stepped towards me and put his arms around me, and we kissed. I literally melted in his arms at that point, but I broke the kiss and told him I needed to go.
Twenty minutes after I got home, the phone rang and it was James asking for me. We chatted for about half an hour and he asked me a lot of questions about my transition and what I felt, was I gay, does him liking me make him gay and so on. He really made me laugh when he pointed out I rearranged his erection for him and ‘that I was the first girl to ever touch it’. I asked how he felt about that and he admitted he really liked it. I asked him if he was a virgin and that he shouldn’t be embarrassed if he was, and he mumbled a yes, he was. He then asked me the same and I decided to be honest, kinda, with him and said that I wasn’t, there was a boy who found out about me and for a while we had sex until he broke up with me and got a girlfriend. He wanted to know a bit about how we had sex and I told him that was private, and that maybe one day he would find out for himself.
I met up with James again the next day in town, but this time we knew which door to meet at. I decided to go with leggings today, I needed him to feel comfortable with me and with nothing down there I hoped he would. He looked at me down there a lot and in McDonald’s he put a hand on my leg and I wondered if he would try and feel me there, but he was the perfect gentleman and didn’t. We went and sat on the grass in the park and I sat opposite him crossed legged and he was literally staring at my crotch while we chatted and I said to him, “So what do you want to ask me about it?” He looked up at me and asked what I meant and I told him he’s not stopped looking at me down there. Finally he asked if I had already had a sex change, and I told him all about tucking. If we do end up going further he will find out so I may as well deal with his curiosity now. We got up and walked around the park just holding hands and chatting away until I realised he was walking us towards a part of the park that’s out of site of everyone. Once we were in a little wooded area we sat on a fallen tree and started kissing and I really enjoyed the feel of his hands on my legs and I had already held his penis once so I just worked my hand towards it again to have a little feel. I was gently stroking him through his jeans when I realised one of his hands was on my inner thigh and my legs were opening for him.
I decided to let this happen and I undid his fly and put my hand in, wrapping it around him, stroking him slowly. This is technically our third date after all. His hand finally got to my crotch and cupped me, rubbing me gently and I loved this! We got a bit hotter and my hand started working faster on him as he pressed his hand against me and I was getting hard myself now and he was running his fingers along my tuck, his fingers tickling the top of my own little erection as I felt him getting closer to cumming. He practically squeezed me down there as he came over my hand inside his jeans, my fingers getting wet as he got slippery. I collected as much as I could in my fingers and took my hand out, licking them clean as he looked me in the eye and never once stopped rubbing me down there. He started to speed up the rubbing me and he really was trying to rub me off as I sat there with my legs wide open and his hand on me.
He sensed that my breathing was changing and focussed his fingers on the head of my own tucked erection. I wrapped my arms around him and pulled him close to me, my legs closing on his hand as I started to cum in my thong. How can I be cumming while tucked is all I could think? He slowed down but kept his hand there and we kissed. Slowly his hand worked it’s way up my body towards my stomach and he tried to work his hand into the waistband of my leggings.
I stopped him, and just whispered in his ear ‘not right now’, and we started to sort ourselves out. When I stood up I was acutely aware of the cum in my thong and I was scared I had left a damp mark that everyone could see. I was desperate for us to get to the toilets so I could clean up. Thankfully it didn’t look like it had left a mark so we had a little walk around the shops and both went our separate ways. We had arranged to go to the cinema on Friday evening and he would come and pick me up at mine. I was really worried about him meeting my mum and sister, but would only tell them just before he was due to arrive. I would be seeing the girls during the day and tell them of course, but tomorrow I have a much more important date and one I was very worried about as I couldn’t stop thinking about a conversation from what seemed like years ago but was about to come true.
———-
When I knocked on Jo and Martin’s door I was nervous. I had worn my tennis skirt, boots and a spaghetti strap vest that showed my pretty pink bra. My make up was on point and although I was nervous I also felt a bit fierce and if I was going to go out, then I was going to get banged on the way! Martin opened the door and I threw myself into his arms, kissing him immediately. He kept saying ‘slow down’ but I was pushing him towards the bedroom and had my hand down his shorts as he backed into the door and I then I froze. On the bed was Jo with her legs over the shoulder of a man who was literally ploughing her. They both stopped and he was clearly deep in her and he laughed and said, “Shit Martin, I didn’t realise she was cute too!” I was so surprised at seeing this I hadn’t moved and my hand was still in Martin’s shorts wrapped around him as we both stood side by side watching them. The man slowly slid out of Jo and it seemed to go on forever as he pulled out; he was huge! He was covered in Jo’s juices and so big that even though he was fully hard it couldn’t point upwards. He walked over to me and kissed my cheek and said, “Hi, I’m Dave, Jo’s bull.” The sweat made his black skin glow and he was looked beautiful. Martin gave me a nudge and I realised I was squeezing his penis as I looked at Dave. Jo stood up and walked over to give me a hug. I’d seen her boobs before when we were trying on clothes but this was the first time she was naked and I was hoping that one day my body would look as amazing as hers. She whispered in my ear that Martin was meant to keep me out, but never mind.
I hadn’t once stopped playing with Martin and Dave looked at me and said, “Well, if you’re not going to stop doing that, you may as well use the other side of the bed.” And he guided Jo back and they started kissing as they laid down. I looked at Martin and his eyes were clearly asking me if I wanted to, so I walked to the bed. I’d had sex with others watching before, been caught more times than I can think of so I sat on the edge and started to pull Martin’s shorts down so I could blow him. Dave and Jo had started having sex again and I looked across at them. Jo gave me a smile and a wink and I was looking at Dave while sucking on Martin. Martin slipped my jacket off and my vest while I undid the zip on my skirt. He stepped out of his shorts and pulled his tee shirt over his head. I was sitting there in my lingerie and clearly not thinking about what was going to happen next. Martin leant down to kiss me and moved me backwards on the bed till I was laying next to Jo. He kissed down from neck to my stomach and lowered my thong and I lifted my hips for him and my legs opened as he moved between them, sliding into me smoothly. I looked at Jo and we smiled at each other as our partners made love to us and we held hands. Martin leant across while still in me and kissed Jo, then he kissed me. I felt my head being turned and Dave was looking right at me and moved in to kiss me while Martin was in me.
O.M.G! I’m officially in a threesome!
After sharing the kiss I focused on Martin and just enjoyed being with him. I desperately wanted to tell both of them I loved them, but with Dave inside Jo it may have been weird. I watch his face as he came inside Jo and saw how happy she looked with him in her. I realised as Martin came inside me I had never once seen them have sex, only flirt with each other. The guys climbed off us and I looked at Jo and we turned to each and hugged. I felt my own erection touch her and was embarrassed about it, but she didn't try and move away from it and it and I sensed it was no big deal for her. When we parted and went to stand up, Dave saw my erection and said, “Wow, a trap!” I had no idea what he meant and neither did Jo or Martin so he explained and I really didn’t like it, it felt insulting and he apologised saying he meant no harm and gave me a hug. His now limp penis felt huge when it pressed against my stomach and when my own erection touched his leg I moved it away from him. I felt strange to be standing there in just my bra with three naked people who had all just had sex while we just chatted. I never mentioned anything about being at school and it was never mentioned by anyone else so I figured it was wise to say nothing now. I’m not sure when it happened but things had started to get a bit flirty again and Dave was clearly flirting with me. Finally he slipped his arms around me and unhooked my bra. My forms had bounced out ages ago and were still on the floor in the bedroom and once the bra was off he kissed me. Now all four of us are naked and I still had my erection and felt Dave’s getting bigger against me. I felt a hand on my shoulder and looked across at Jo. “It’s ok, you can do it.” She said to me, and I reached out and held what was clearly too big to go in my mouth, let alone anywhere else as it kept getting harder in my hand.
Dave took my free hand and led me back to the bedroom and Martin and Jo followed behind, holding hands. Martin was getting harder as he walked and I licked my lips as I looked at him and stroked Dave. I thought to myself this is just so weird, I just hope it doesn’t stop. In the bedroom, I sat on the edge of the bed and Jo sat next to me as Martin stepped forward and she took him into her mouth. She looked so pretty sucking on him and I hoped I looked that good with him in my mouth as I felt Dave’s penis touch my cheek. I turned to face it and kissed it, licking it and slowly starting to get more and more turned on by him. Opening my mouth I could just about get the head in and ran my tongue around it as much as possible. After a short while I felt myself being laid back and I just opened my legs for him as he lay on top of me. I could feel his cock touch me but I was so scared at the size of him I felt like I had tightened up, but he didn’t seem concerned. We just kept kissing and caressing each other while he was there, hard, waiting at the door. I looked across at Jo and Martin and he was inside her, kissing each other and I went back to Dave. I heard Martin cum and Jo sigh and I so wanted to feel Dave in me but just wasn’t sure if it would happen as he was just so big. Martin and Jo sat up and looked over and she must have seen I was nervous as they suggested that Dave stop, but I wrapped my legs around him.
Jo ran her hand around Dave and felt that he wasn’t in me. She suggested we try something else. Dave picked me up and and he laid on his back and I was astride him thinking why didn’t I think of this earlier? Jo grabbed some lube and wiped it all over Dave while I lifted myself up on my knees. Jo then suggested than I instead crouch over him, “it will help.” She said. I lifted myself up and looked down at Dave as I lined him up. Jo told me to take my time and I pushed down on him. He wasn’t going in and I was getting more and more desperate to get laid as Martin told me to relax and Dave was stroking my legs. He was pushing in, but not quite making it, every time I thought we had it, he was just too big for me. Then suddenly he wasn’t too big for me and he was inside me, not by much but just that little bit was a start and he was so big it hurt me for the first time in a long time. I needed to relax and Jo and Martin supported me. I was able to lower myself a bit more and relax, then a bit more and relax then suddenly I was able to slide down him and the thing that was too big for my mouth turned out not to be too big for me at all as he went deeper than I’ve ever experienced.
I just sat on him, feeling him in me and wondering what this would mean for me with something so big, would Martin feel tiny now? And what about James, he’s not as big as Martin and I really like him and want him to like me. Thinking about James made having Dave’s massive tool inside me feel better and I started to ride him. I really like James and hope that we may have something going forward and I hope he doesn’t mind that I have a penis, but Dave didn’t mind and he seemed to like trying to make me cum. Something Dave was doing was hitting an amazing spot in me and I knew I wouldn’t last much longer and didn’t know what to do. I could feel myself tightening up on Dave and then it happened, I came. I tried to turn my body away from him but the first spurt landed on his chest and neck. The second and third spurts hit Jo and Martin, with the fourth landing on the bed. I sat on Dave, my body in spasms as I came down from my high feeling amazing. Jo gave me a quick kiss and told me how happy I looked and I watched some of my cum drip from her right boob and then Martin gave me a kiss with my cum on his stomach, telling me now I needed to do the same for Dave. I looked at him and leant down to give the man inside me a kiss, and I started to roll my hips on him, raising myself up and lowering myself. I was working him and wanted to put a smile of his face. I rode him like I had never rode anyone before until he grabbed my hips and pulled me onto him as he thrust up. I could feel him unloading into me, again and again and it felt like he was putting so much into me I would burst! Finally he relaxed his grip on me and I leant down to give him a kiss.
I was about to move off him, but Jo stopped me saying that Dave was a heavy cummer and I should just relax for a bit. I could feel him going soft but the shear size of him kept him in me. Jo said if I just got of him now it would all drip out and she knew how much I liked the feeling of it when I was walking around. As I was coming down from my own high and my lust was fading I suddenly had a thought, this man inside me was older than Martin and he may tell people about this and I was worried about their jobs. I looked at them both and they smiled as I said, “I’m worried about people finding out about this.” Dave looked a bit confused and Jo told me not to worry. Dave rolled me to the side and slid out of me and he kissed me, high fives Martin and gave Jo a kiss saying it was time for him to go. He got up and went to their bathroom and I heard the shower start. Jo handed me my thong and put her own underwear on so I did the same and the three of us went into the kitchen and Dave shortly joined us, pulling on his shirt. He gave Jo a kiss and shook Martin’s hand and then pulled me into a kiss, thanking me before he left. I looked at them and said, “I guess we need to talk?” We went and sat down and Martin was still naked which was funny in a way as I knew the deal was if Amy starts going to school this has to stop so very soon I wouldn’t get to see him naked anymore and just be another girl with a crush on him. Both of them were happy I was the one who started talking about this, and I explained it was why I wouldn't let Martin talk in case he tried to stop it happening, but in the end it became the best possible farewell. I told Martin how much I was looking forward to crushing on him and he said it will be hard not to respond when I do, but it has to be that way now. I told them both I loved them and couldn’t say thank you enough for what they have done for me.
I then told them all about James and how much I was looking forward to what will happen with him, and how scared I will be when we have sex. Then I reached over and held Martin’s penis saying it’s unlikely he will be this big. I kept hold of it and stroked him a little with my hand and he gave a little kiss saying he needed to go to the bathroom. He moved off and I looked at Jo and apologised for cumming on her and she laughed saying it was ok. She slipped off her bra and grabbed a wet wipe to clean herself and I told her how amazing her body was and I hope mine looks like it soon. She gave me a hug and kissed me saying it was ok, one day I will have my own boobs. Martin returned and was fully erect and he took my hand saying we still had time to say goodbye and we went to bedroom, with Jo following. Jo said we can all say goodbye and she dropped her underwear and started to lower mine as we walked until I stepped out of them. Martin stood behind me and wrapped his arms around me, pressing against me and I reached down and lined him up and he was in me. But Jo, well I wasn’t expecting this, she laid on the bed and opened her legs and Martin walked me towards her. My brain was confused but my body wasn’t as I was already hard and although I must be the smallest she’ve ever seen, she took my hands and lowered me to her while her boyfriend was in me. I was nervous, I’ve never been with a girl and wasn’t really sure how this would work, how can I be with both at the same time?
Afterwards, laying there together we all kissed and said our goodbyes. I enjoyed being inside Jo but I’m not sure she would have felt much, and I wonder if I would have done it if Martin hadn’t been inside me at the same time. We all got cleaned up and dressed chatting together and I did wonder if I would ever tell anyone about this. I think I knew that I would tell someone about Dave as that really was amazing. I certainly had a lot to think about on the way home, and strangely sitting on the bus with a pervert next to me playing with himself didn’t bother me this time. At home I was told the girls had all been trying to reach me about tomorrow and I just lied saying I was with Nicola knowing she would cover for me. I rang Jodie to find out what was happening tomorrow and it was another trip into town shopping and I was excited about this, I still had a little money and I could buy something for my date with James in the evening, so after dinner I curled up on the sofa to watch TV day dreaming about James, and thinking how lucky I am to have so many people helping me.
I was very happy.
The next day though, I was very sore and wore leggings and a crop top that hung off one shoulder. Maybe after yesterday I felt a little dirty, I don’t know, but I tried not to let it play on my mind. I actually saw Steve on a date with his new girlfriend and gave them a little wave, so I suspect they both had a few things to talk about after that. I paid for the girls lunch and introduced them to Nicola as her mum was getting her some new school uniform. I was really pleased they all liked her and I planned to meet with her on Sunday to I could let her know about Amy officially starting school on Monday. The girls had a lot of opinions on what I should wear for my date.
While we were in Primark, I had one of the best experiences of my girlhood. The boy that attacked me was being led round by his mother getting him some new shoes. When he saw me with the girls his eyes went wide and I decided I wasn’t going to let him cower me. I walked over and he was trying to make his mum mover away from me. The girls were watching me walk towards him, almost marching over, and only realised where I was going when I reached him. His mum looked at me and asked if I went to his school, and I said, “Not his new school, I go to the one he was expelled from.” He mum looked at him with anger, then apologised to me for what he did. I looked at her for the first time, glad I looked so good today, and said to her, “I’m the last girl he spoke to there before he had to run away suddenly. You could say I’m the last girl he touched and why he left.” His mum looked me up and down, shot him an angry look and said to me, “I’m sorry.” She looked like she meant it, and I felt sorry for her for having such an evil shit of a son. “Well, I need to go, I think I saw a police officer outside and I still have plenty of time to speak to them!” I spun on my heel and walked back to the girls. They told me that the evil shit was literally dragged out the store by his mum, clearly telling him off as they walked out.
I like being a survivor!
That evening I was putting the last touches to my makeup on for my date, and still couldn’t believe I had settled for what I wore yesterday as I love the tennis skirt and spaghetti strap top. I had only told mum about James an hour ago and reassured her he knew all about me and was ok with everything. She insisted on driving us to the cinema and gave me some money for a cab home. The date was wonderful! I can’t even remember what the film was. We held hands, I cuddled up to him, we kissed and chatted. He liked me. Mum dropped me off first, but gave us a little time to kiss goodbye and arrange to meet up during the week. It felt really good to have a date with someone who didn’t try and have sex with me, just wanted to be with me and get to know me. He made me feel special and I wanted to feel it more and more.
After he got home he texted me, and we kept talking for hours. I’m not sure what time I fell asleep, but I had left James on ‘read’ and was so worried I had upset him., I sent loads of texts before I got a reply. He had fallen asleep waiting for my reply. I think I was falling in love with him for real. We chatted for a couple of hours on Sunday and he was really worried for my official first day of school. I was so pleased that he was trying to keep me feeling safe and reassured. I don’t know why I felt so nervous, everyone has seen me but I just couldn't shake it. Nicola kept talking to me to help me and the girls were all there for me.
I woke up having barely slept and got ready for school. The black tights, the short pencil skirt, fitted shirt and tie, blazer and the boring flats. I put two studs in my ear piercings, did my light make up and out my books in my shoulder bag. Mum offered to take me into school, but I knew if I didn’t walk in as usual I would be scared forever. I opened the door to walk out, and there was James. He was waiting for me to walk me to school. I gave him a quick kiss and we walked hand in hand and he was such a gentleman he never once complained about me squeezing his hand when I saw people. He walked me to meet the girls, then we kissed goodbye with a promise to keep texting him through the day to let him know I was ok. I watched him walk off and Sarah looked at me and said “Well I don’t like him.” I was heartbroken, why wouldn't she like him! He’s lovely! Sarah said, “Did you see what school he goes to! How could you date the kindest, cutest guy who clearly has a big cock in his trousers who goes to that school!” She linked arms with me, and the girls all linked arms in a line as we walked towards Amy’s first school day. Sarah looked at me and with a big smile on her face said, “I’m not sure we can be friends anymore.”
This survivor has the best friends in the world, and quite possibly the best boyfriend.
The end
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How much of this is based on truth? Well everything up being caught by the teacher when asked to empty out the pockets is real, from then on it's what I wished would have happened, although I did go to the teens disco a bit later
The rest of the day at school I had classes with Nicola so we sat together and I had to keep reminding myself not to be so girly in public, but at least for the first time, I now felt that I had a BFF I could be a girl with. I also realised that I had now seen another erection, and Bev was right, I am a lucky girl, but not by much. It also occurred to me that I had held another man’s cum, even if it was in his used condom.
It was break time, and Nicola and I got up to go and meet up with the guys, but the teacher asked me to hang on for a word. I told Nicola to head off and I would meet her before our final lesson of the day. Mr Christian was waiting patiently for me as I walked to his desk, so I assumed I hadn’t done anything wrong as he didn’t looked annoyed. He waited for the classroom door to shut as the last of my classmates walked out and cleared his throat.
“I don’t want you to be embarrassed, but would you mind emptying your pockets?”
I looked at him and suddenly felt scared and my eyes went wide. My trousers didn’t have pockets because they weren’t boy’s trousers. He smiled and said it’s ok, as I hung my head in shame at being caught. “You had drama this morning, didn’t you?” I nodded but still said nothing. “Well, you know me and Miss Reeves are dating and live together? Well, she noticed what you are wearing and mentioned it to me. You don’t need to worry, but we wanted to let you know we have seen what you’ve been wearing recently but we don’t think anyone else has noticed, so we want you to be careful”.
I looked up at him from under my eyelashes while biting my lip and realised I was doing the full Princess Diana to him. I barely whispered when I replied “Sorry sir” to him. He smiled and told me there was nothing to be sorry for, he was just looking out for me. I left the classroom scared and was trying to stretch my jumper down to cover more of my body, especially my bum and lack of pockets or zips where there should be zips. I could feel Mr Christian’s eyes on me as I left. I was scared. I never mentioned any of this to Nicola or Steve, I didn’t want to draw attention to the fact that I would need to be a little less Amy at school in future. As I was leaving school at the end of the day, living the remaining hour in pure fear and trying as hard as possible to hide it while thankful it was Friday, Miss Reeves called out to me. I stopped and looked and was tempted to run, but I would be seeing her next week regardless so reluctantly walked over to her. She smiled at me all the way. When I got there, she told me to relax and not worry, I wasn’t in trouble, she was just concerned about me. She reached into her bag and handed me a slip of paper which had an address on it.
“Look, you can’t tell anyone this, but if you want to come round to my flat it’s a safe space for you and you can talk about this and also be who you want to be for a bit. How does that sound?”
I looked at her and she was smiling gently at me. “Both of us know about you, and I will be there from ten tomorrow while Martin, I mean Mr Christian will be playing football so please, if you are free come round and you can relax and we can chat.” I put the slip of paper into my school bag, said a quiet thank you and rushed off. This was a bit different to a couple of school friends, my sister and the boy I’m having sex with knowing about, this was grown ups and I was more scared they would tell on me and everyone at school would laugh at me all the time. I was a bit distant from my mum and sister that night, barely doing anything as I knew no matter what I needed to go and see Miss Reeves. Every time I thought about it I was thinking I would just go in my normal boys clothes, but I also knew I had spent the whole day walking around the next town over and no one batted an eye. If I was going to be there as Amy, then Amy wasn’t going to hide, even if she would have to hide a little on the way over.
Saturday morning I woke up, showered and made sure my legs and everywhere else was smooth and quietly got changed and packed some clothes in my bag. I planned to do pretty much the same as I did for my daytrip and even selected the same clothes from my limited supply and headed over to see Miss Reeves telling my mum I was just heading over to a friends for the day. The walk there was scary, I felt like everyone knew I was wearing a bra and that I had VPL, but I got to her building. I was a little early and trying to work out what to do, should I ring the intercom a bit early or wait in case she wasn’t home yet. Now I was worried she wouldn’t be there and I now had a bag full of girl clothes and nowhere to go! I was trying to keep calm when I saw Mr Christian come out the building and walk towards me. A big smile broke on his face as he said hello and told me that it was ok, I should ring the buzzer. Nervously I walked to the door and pressed the buttons. Miss Reeves answered in seconds, “Have you forgot your keys?”
I was completely thrown and just said “Miss Reeves?”
“Oh hi, sorry I thought you were Martin, come on up.” And with that the door buzzed and I went in. As I got out the lift for her floor, I could see the door was open, but I still knocked and was invited in. I felt really scared now, but Miss Reeves walked out of a room and came up and gave me a big hug, holding me for what seemed like forever as I started to relax.
“I’m so glad you decided to come today. Now, let’s have a look at you.” She looked me up and down, then said, “I could feel your bra, so I’m guessing you have a change of clothes. The bedroom is over there, take your time and come out when you’re ready”.
Going into the room I realised it was a spare bedroom as it didn’t look lived in. I put my bag on the bed and started to get my clothes out, stopped and then pulled the curtains almost shut. I didn’t think it was likely that anyone could see in, but I felt quite exposed. My jacket and trousers came off, my chicken fillets went in the bra, and I put my skirt on, then my boots. I sat on the edge of the bed and carefully brushed out my wig and put that on, looking in the mirror as I did so. Then it was time to start with the make-up and at least unlike the train I had a bit of time. There was a knock on the door and Miss Reeves asked if I was ok and I replied, “It’s ok, I’m just doing my makeup.” She asked if I was decent and when I said I was dressed she opened the door and for the first time an adult saw me dressed.
“Well don’t you look pretty.” She said as she walked over to me and gave me another hug, then sat down next to me. “I wasn’t expecting you to bring makeup, if I had known I would have made sure there was a chair and dresser in here for you.” She stood up. “Come on, it will be easier in my room.” We both took my make-up into her room, and I sat on the stool in front of her dresser and admired the sheer volume of makeup. When I was finished, I looked at her and said, “Thank for this Miss.” She laughed and told me to call her by her first name here, Jo.
She gave me another hug and asked, “So what should I call you?” I told her I was Amy.
We went into her living room and I loved that she has a balcony, with a view rather than just looking at a carpark. She got a can of coke and gave me a straw and she made herself a coffee and we both stood on the balcony chatting. She hadn’t asked me anything about being Amy, just chatted to me about music and TV. After about an hour or so of this I started to calm down and although she was an adult, she had pointed out that her and Martin were only 25, so not really much older than me, even though it didn’t feel that way. She even let me try on some of her clothes after I had said how much I admired one of her dresses. It was kinda strange at first as we were trying clothes on with one of us going out the room when the other got changed, but finally I just took one of her dresses off in front of her. She was a bit taken aback at first and then just took hers off as well and then it was no big deal, we were just two girls together trying on clothes. None of her shoes fitted me, so some things looked a bit weird with my boots on, but some of the things I got to wear were designer clothes, so I didn’t care.
As much fun as it was, it couldn’t go on forever, so Jo made us both a salad and we had lunch. Finally, she asked me the question that I knew was coming. “So Amy, tell me about boys?” I decided to try and avoid it. “Do you mean what it feels like to be a boy?” I replied.
She smiled and said, “You know full well what I meant”. I took a deep breath, and told her about me and Steve, how it started, I even admitted about the day we both bunked off school and then met Nicola and Michael, how my sister caught me with Steve inside me, and how I decided to start trying to dress as much like a girl at school as I could. Jo asked me how I got started with dressing and having told her I’d had sex it was no big deal anymore. She felt like a cool aunt, not that I had one but I felt like I could trust her, so I told her my story, trying things on, feeling guilty, all the usual stuff really.
We both turned our heads as the front door opened and Mr Christian walked in. He looked at me and just said, “Wow, you look gorgeous!” And he went to the fridge and got himself a can of coke and sat down opposite us. Jo looked at him and said “Her name is Amy, and she is my friend.” Mr Christian told me to call him Martin, and then they both laid down the law to me. I could use their first name only when I was Amy and never to use it at school, that I could come and talk to them whenever I wanted and that I shouldn’t feel scared. We all chatted for a couple more hours and then Jo asked me if I was going to see Steve this weekend, and I admitted I didn’t know yet, but we will probably meet up tomorrow somehow, maybe when his parents were at church. Jo looked at Martin and said, “Steve is her boyfriend.” I blushed and wanted to hide my face, but Martin said Steve is a lucky boy and I should be pleased to have him. Jo and me giggled at that and he said, “ok, he is lucky to have you then by the sounds of it.”
At four I knew it was time for me to leave, but Jo insisted I come round after school on Tuesday for some more girly time, and I went to take my makeup off and get changed back to being a boy. I did take my bra off for the walk home though, and both Jo and Martin gave me a hug and told me how much they enjoyed spending time with Amy as I left. Walking home I felt a lot better, for the first time I had been able to talk about this with someone, and I although I couldn’t tell Steve about meeting up with Jo and Martin as it would risk their jobs, I was still looking forward to seeing him if he was free.
He was, and we had two wonderful hours of fun together.
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On Monday I didn’t wear the clothes I really wanted to as we had PE, and other than a quick nod from Jo or Martin in the corridors, the day was just like any other. Steve wanted to slip off to the staircase at the library at lunchtime, but as I was dressed in all boy clothes, I didn’t really want to do that. But on Tuesday we did, even though I was wearing boy trousers, everything else I was wearing was girl and once again I was on my back with Nicola laying near me as both of our boyfriends used our bodies to enjoy themselves and we all went back to school with a smile. At the end of the day, I know Steve was hoping to walk me home and was disappointed not get home with me, so I promised him that he will get something on the way to school tomorrow, at lunch time and again after school and that made him happy. I made sure no one could see us and gave him a kiss and had to stop him getting over excited as I was already tempted to just lay down where we were in a corridor and let him have his way. I smiled as I watched him walk away trying to hide his erection as I made my way to Jo and Martin’s.
When I got there, Jo was in but there was no Martin to be seen and she was dressed in workout gear pushed me into the bedroom, told me she had noticed my VPL and to get changed. On the bed was another workout leotard and a pair of trainers and she told me us girls have to work for our figures, and it would be nice to have a workout partner for a change. I stripped down to my underwear and took off my tights and was wishing I had a bra with me when I noticed there was a sports bra and a pair of chicken fillets and that the trainers were a cheap pair from the market in my size. I quickly put them on, and went out to see Jo, who was holding a wig from the drama store that was shorter than mine, but a similar colour. She helped me put it on and put a scrunchie on it to keep it in a ponytail. “Your hair isn’t too bad but giving it a better style wouldn’t be a good idea. Anyway, let’s get some lippy on you.” Jo stuck an exercise DVD on and I tried to do the moves to keep up with her, and it was tough! I couldn’t believe how difficult it was and was glad I hadn’t put any other makeup on as it would have run for sure. I was really worried about my tuck falling apart while we were working out, but it stayed secure and the leotard definitely helped.
When the workout was over, I turned around and there was Martin, standing in the doorway looking at us. He looked both of us up and down and at first I was a bit weirded out by it, but then I remembered this is Martin, not Mr Christian, and it’s not like I wasn’t flaunting it when bunking off school for older men, so what’s the big deal. Plus, I’d never seen him do that with any of the girls at school who fancied him, so I was one up on them! He said, “Does this mean I can now watch the news?” Jo told him he could and he sat down as we both got a drink and then joined him. He looked at Jo and said, “Seriously hun, you look great, you don’t need to do that.” She pointed out that she looks good because she does this, and he has never complained before. He looked at me, “You too Amy, you look great too. In fact, I have to admit I did quite enjoy watching you both for the last ten minutes.”
Oh. My. God! The last ten we were both bent over at the waist with our bums facing the door and he was watching us! I was blushing for a thousand people as Jo got up and walked over to him, gave him a kiss and then turned around and bent at the waist looking back at him and said, “You mean like this?” Jo gave me a wink, and I thought screw it, if she can do it I can as well. Besides, he’s already been watching so what’s the point, especially as I will be here on Thursday doing the same. So I got up, and did a similar pose and said to Jo, “No, it was more like this.” And we both did a mini version of what had killed me a second ago before we both started laughing and fell on the floor. He slid down to floor and started tickling Jo and trying to kiss her, and I moved out of the way laughing with them both. I also realised I had just purposely tried to turn a man on, not a boy, and this man knew not only what I was but also how old I was. Martin slowed down the tickling and increased the kissing and they were both making out a little bit and I’m sure I saw Jo stroke Martin’s penis, but I couldn’t really see. While I was trying to work out if I did see that, Martin moved Jo out of the way, and lunged for me, surprising me as he started to tickle me.
“You think I forgot you were just as guilty as Jo, did you?” He said, tickling me as I was laughing and screaming at the same time. It was both torture and fun at the same time and he slowed down the tickling as I lay on my side with my back to him and he leant over me as my breathing calmed down. “I’m sorry, I didn’t mean it.” I told him, realising that once again I was doing the Princess Diana to him and that I’ve felt Steve’s erection pressed against me enough times to know what it feels like when a man is hard. He stopped and I rolled ever so slightly towards him, pressing against him a bit more. He never moved away, and I kept the pressure up when Jo pointed out we should both get changed. As we both got changed Jo offered to wash the sports bra for me and told me she hoped the tickling session wasn’t too weird for me. “No, I think I need to apologise to you, I shouldn’t have joined in with the teasing.” She told me not to worry, it was just harmless fun, but I kept trying to say sorry as it looked like they were about to do it, and she kept telling me it was fine, but then said, “I’m sorry I gave him the erection he had when he started tickling you.” I told her it was no big deal, although it was definitely bigger than anything I had experienced before and we both started giggling. We chatted a bit more but for some reason I didn’t want Martin to see me as a boy, even though he would tomorrow anyway in lessons. As I walked home, I was playing back the conversation and realised that jo hadn’t said she had given him the erection, but ‘we’ had given it to him. I knew I needed to talk to Jo about that, but it couldn’t happen at school, so I had to wait. When I saw Steve that evening in the park in my sister’s old jeans, I did find myself comparing him to Martin, even though I had only felt it touching me.
After school on Thursday I was really nervous going to Jo’s, but she was completely normal with me and never once mentioned what happened on Tuesday. We had our workout, but this time Martin came home a bit earlier and just sat on the sofa as we did the routine. It was starting to feel a bit easier, learning the moves and almost keeping up with the video, but I was nowhere near as good as Jo. When we finished, Martin got us both a drink and apologised to me for the tickling and was a complete gentleman. He got us both towels as we sat there and got our breaths back, and I noticed he had a semi erection. Jo saw me looking and told me not to worry about it, so as quickly as possible I said to her, “I can’t believe how quickly you can get him like that.” Jo looked at me and replied, “just like last time, we’re both responsible for that one.” I was blushing once again when he handed me a towel and I found it hard to look up at him, especially as his semi erect penis was at eye level. I was feeling very awkward and finally Jo broke it by telling him I was embarrassed at his erection. I felt like the earth would open up and swallow me whole, and when it didn’t, I started wishing it would. He was a gentleman once again and apologised for it, but said it was an involuntary reaction to seeing two beautiful women in tight clothing. I felt a lot better at being called beautiful, but then he really surprised me by putting his hand down his pants and saying he needed to rearrange everything and moved his penis from pointing down to pointing up and it made it look even more obvious!
Jo looked at me and said, “Ignore him.” So we did. We chatted together while he looked at us. As Jo and me were getting changed back, she asked me if I wanted to come round again this Saturday and I really did, even with the slight weirdness of Martin and his erection, I still enjoyed spending time with both of them.
The next day at school was a Friday and I had a lesson with both of them and decided to wear my sister’s old school trousers and fem myself up as much as I dared. Steve was very aware of how I was dressed and knew we would have a very nice lunchbreak together. I’m glad that Nicola and Michael weren’t with us this time as it made it feel more intimate when he entered me and we kissed and less like we were putting on a show. Jo noticed what I was wearing and almost called me Amy during drama, but changed it into saying ‘and’, but I was already prepared for that happening. Steve had done it to me once in front of his parents so a teacher saying it in a room full of kids is nothing. At the end of the lesson, she sat us all down early which usually means a big announcement of some sort, and I noticed the ‘star’ students were looking a bit smug.
Jo Said, “Ok you lot, it’s that time of year again, time for the school show. Some of you I’ve already approached for parts, but there will be auditions next week each lunch break so if anyone would like to try out for the show, please come along.” She kept looking at me as she was saying this, but if there was a message she wanted to get across, I was missing it but wasn’t worried as she would tell me tomorrow. She knew I enjoyed drama but had no interest in acting on stage. She went on to say she would need some people to help with setting it up and hoped that anyone who didn’t get a part would still help in some way. “And even though some people may think they are going to get a starring role, it will depend on the auditions and if someone is better for the part, they will get it instead.” She was known for being really tough with her casting choices and once a girl went home in tears for not getting the role she thought she deserved. I’ll be honest, I wasn’t paying a huge amount of attention as Steve was sitting next to me and stroking my leg so no one could see and I knew he wanted us to get to the library as quickly as possible.
We rushed there as soon as we were let out and once in the stairway, I opened his zip and put my hand in. I was desperate for him at this point and took his hard cock out and walked up the stairs, leading him by it as his hands were stroking my bum. Once we were at a safe place, I turned around and took him into my mouth, I needed to taste him and needed to taste him right now. He must have been turned on as it didn’t take a lot of licking and sucking on him till he exploded in my mouth. There was so much cum it felt like he had been saving it for me especially and I was regretting not having just gone for the main course and riding him to feel it inside me. We went a bit further up the stairs and kissed for a bit while I kept stroking him before he started to undress me. Before long I was wearing nothing but my hold ups, thong and a lacy vest as he slowly laid me down and opened my legs, getting between them with his hardness pointing at where it wanted to be. I pulled my thong to the side and guided him in me. He entered me slowly at first as I got used to him in me and he was all the way in. I was pulling him into me with my hands as I kissed him. We started off by making love and then he got faster as he began to thrust into me as quickly and hard as he could. We both came at the same time and kissed each other gently. As he lay on top of me, inside me still twitching, I kissed him and said, “Thank you, I needed that.” He smiled, gave me a kiss and started pulling out of me but I lifted my hips to keep him in me. “I needed you too.” He said as his penis left me feeling empty. He looked at me and thrust forward hard and was once again deep inside me, and even though he had had just cum, we made love slowly, kissing all the time for what seemed like forever. We both froze when we heard a door open and voices below us, not moving. We looked at each other and stifled a giggle as we heard them open another door and leave us alone, when we realised he stopped when we had both thrust forward. I looked at his watch and saw we were running out of time to get back to school so we tried to get dressed without him pulling out but had to separate from each other and rushed back, just getting to our classes on time. I took my seat next to Nicola and she looked at me, and Mr Christian was looking at me, smiled then looked away. Nicola whispered to me, “You look like you’ve been royally fucked.” I blushed and she smiled. I sneaked at look at Mr Christian, and he was smiling at me and I realised he knew about Steve and could work out what we had been doing.
On Saturday when I arrived at Jo’s, she pulled me into the bedroom to get changed. Today I had worn my hold ups, my skirt was on under my trousers and chicken fillets in my bra. The first thing she asked me is did I have fun on my lunch break in the library with Steve. “How did you know!” I asked her. She told me that her and Martin had seen us going in there and he told her how I looked like I had just been fucked within an inch of my life when I got to his lesson. I admitted I had and told her all about it and like girls do, we talked about our sex lives as I was putting on my makeup. As soon as I was finished, she asked me try a jacket on to see how it looked, handed me a handbag and dragged me out the door saying we were going shopping. A short drive in her car and we were looking around the shops, trying things on. I brought myself a pair of heels as I really wanted my own and we picked up a few outfits in charity shops including a calf length pencil skirt and a pair of white pedal pushers and a couple of tops, plus some underwear that I could leave at hers for when I needed it. We went back to hers and I hung up and put away my clothes in their spare room and we sat down to watch Grease, right as Martin came home. I saw them both look at each other saying nothing and realised that Martin must have had it confirmed that I had sex yesterday before his class. No biggie, he had already guessed but I hope he doesn’t ask. We watched the film together and although I hadn’t seen it for a while, me and Jo did sing along to some of the songs and demand that Martin take part. When it finished, she asked me if I was going to audition for the play and I pointed out I don’t really look like a T Bird. She looked at me and said, “No, I was thinking a Pink Lady.” She hit pause and said, “That one.”
I looked at her and was a bit confused and just said, “Huh?”
When the film finished, she asked me if I was going to audition for the play and I pointed out I don’t really look like a T Bird. She looked at me and said, “No, I was thinking a Pink Lady.” She hit pause and said, “That one.”
I looked at her and was a bit confused and just said, “Huh?”
“Seriously, you can sing ok for the backing vocals you’ll be doing, you look great and think what a great excuse this would be! I know who Sandy and Rizzo will be, the T Birds are already cast. All I need now are a few people to be background people, one other pink lady and a couple of the background girls. Plus you.”
I was dumbstruck, this was a really big thing to do and I looked at the screen at Marty and thought about her style all through the film and how much I wanted to have her part, how much fun it would be. But I was nervous about being on stage. Jo pointed out that every time I go out I either have to act as a girl or as a guy so being on stage is no different. All I would need to do is audition and she would do the rest, but I would need to audition each day as she went through the process before offering me the role. I really wasn’t sure, but Jo kept humming the bars of the songs, and had me to a mini fashion show for Martin (which is when I realised that we had been buying Marty’s costume for the show that would fit me). Even after getting changed and walking home I was still a bit dumbstruck, so much so that on Sunday I mentioned I to both my mum and sister that I was thinking of auditioning for it, even though I knew I was going to do it. When I told Steve on the way to school on Monday I was going to audition he thought I was a bit mad (plus it meant we wouldn’t get to go to the library together), so I think he was a bit upset with me and while he wasn’t giving me the cold shoulder, he was very much not treating me like Amy anymore.
Anyway, that lunchtime I went to the audition and when asked what role I wanted just shrugged and said I don’t mind. I knew what I would get but couldn’t exactly say out loud I was going for a girl part. Each day that week I had to go back until on the Friday it was me and a girl auditioning together. We had to sing different songs, and each of us singing both parts to You’re the one that I want, when at the end Jo talked to both of us one by one, starting with the girl. They were on the other side of the room when I heard the girl say out loud, “Are you serious!”, but Jo must have said something that calmed her down as she walked out and looked at me with a smile that said she got the part and I didn’t. Then Jo walked over to me and sat down on the floor with me. She looked about the room as if she was going to give me bad news, but the moment she looked at me she smiled and said, “You got the part.” For half a minute I was massively excited, and I squealed in delight. Then realisation set in. “How will I be able to do this?”, but she patted my knee and said don’t worry, we’ll talk tomorrow.
On Saturday I Arrived at Jo’s and this time Martin was there as well. After I got changed we talked a lot and discussed how to make this happen. Basically, I was going to talk to my mum about it, and Jo was going to get it finalised with the school who had agreed I could have the role if my parents were ok with it. Then it would be the rehearsals and talking it over with the rest of the Pink Lady’s and the girls cast were ok with it. That night I mentioned to my mum that I had been offered a part in the school show and with a question-and-answer session I told her it was Grease, but I was waiting to be told exactly what part I would play. She was thrilled and even my sister was excited as she loves Grease but told me it would be rubbish as it was a school thing. Later, I told my sister what part I had been offered and that a girl I had to compete with was turned down. She was really worried about this, but I made her promise not to tell mum. The next day mum asked me if I had really been offered the part of a girl. My sister had grassed me up, and I now felt a bit scared of what else might have said. I was easier to admit that yes I think I have, but I’m not sure if it was a joke. My mum burst out laughing and said that ‘at least it would mean more people are likely to come and see the boy acting a women’s part’. We chatted a bit about it, and I said that I hadn’t yet said no, but wasn’t really sure if I had got it wrong as I was offered the part of Marty, but Marty in the film is a girl. So once again I ended up watching Grease, but this time with my mum and we both sang along to the film and she admitted I could probably play that part but maybe they meant a different Marty, but that if I wanted to do the part she wouldn’t have a problem, so long as I was ok with it.
So on Monday, when I saw Jo in the corridor I gave her the thumbs up and everything went into overdrive. I was told there were a lot of discussions and phone calls, but finally I was called to the headmaster’s office where both Jo and my mum were waiting. There I was formally told that yes, I had been offered the part of Marty, a Pink Lady and if I wanted the part it was mine. The only other role being offered to me was one of the boring cheerleaders who hate the Pink Lady’s, and the girl offered that part would understudy me. If I decide to do this the I have to take it seriously and if I do not take the role seriously I would get a lot of detention for wasting people’s time.
I looked at them, and said, “This is the sort of thing that seems silly, but I may never get a chance like this again so I will do it.”
There was a lot more discussion about the role and what I needed to do which basically meant Jo was going to give up some of her own time to help me. After the meeting finished and before I went back to class mum gave me a big hug and asked me again if I wanted to do this, and I nodded and went back to class with the instruction of reporting to the drama studio after school. I met up with Nicola as soon as I could in break and told her I was going to be in Grease and a Pink Lady. She screamed in excitement and gave me a hug. Next we told Michael and then Steve. Michael thought it was funny, but Steve just said, “Oh’, and Nicola looked at me. She said she was going to get a drink and asked me to come and told me that she thinks Steve is worried what people will say about him as you are both close. I was worried that it might be over with him, but she pointed out he’s a man and will do pretty much anything if you promise them a blowjob. We looked at each other and started giggling and couldn’t stop when we got back to the guys. Steve was still a bit cold with me for the rest of the day, but I managed to get him to agree to come to the drama studio with me before we went home. I had a suspicion of what Jo was going to do when I got there.
We walked in and Jo, sorry, Miss Reeves looked up and saw both of us. She put on a show for Steve and said that if I was going to do this I had to take it seriously and it started right now. She walked to the drama store and came out with a shoe box, a shoe box I recognised. She opened it and showed them to me and said, “These might fit you. Try them on now please.” And passed the box to me. What was funny is that Steve wasn’t surprised I was wearing tights that day, and neither was Jo, but Miss Reeves stopped me and asked. “What are they?” she said, pointing at my feet. I looked at her and said I had borrowed them from Nicola as I guessed something like this was coming. Miss Reeves looked at me sternly, and said, “I would rather you didn’t try and second guess my direction.” I looked at Steve and he was blushing madly and looking away and when I looked back at Miss Reeves, Jo smiled at me and winked. I slipped the shoes on and stood up. Miss Reeves asked me how they felt, and I said they seemed to fit ok, and she told me to try walking in them. For Steve, I worked it and really worked it as I walked. I could feel his eyes looking at my legs and bum as walked, swaying my hips doing the full model runway walk that I had practiced hundreds of times. When I got back I sat down and lifted one leg over the over and dangled the shoe from my toes. I could practically feel the heat from Steve’s erection, but Miss Reeves told me I needed to practice walking in them as much as I could at home so that eventually I would be able to walk like a woman while wearing them. While Steve was looking at my legs, Jo gave me a wink.
Miss Reeves said, “Most of the pupils will have gone by now, but I expect you to at least try walking to the gate while wearing them, then you can change them, although I suspect it won’t take long for people to find out what you’ve agreed to do.” She looked away at this point and I just knew she was trying to hide a smile from Steve. Then she looked at him, “Steve, I’m glad you’re here, I need you to stay with her for as long as possible to make sure she doesn’t fall over.” He never noticed that Jo was calling me ‘she’. Steve looked at Miss Reeves and she said, “Please take care of her, this is a very brave thing to do.”
I stood up and walked the two steps to pick up my bag and crouched down to put my shoes in them. I looked at Steve and he had a very clear erection straining at his trousers. I put my arm on his and asked if it was ok, as I needed a little help. He croaked a yes, and we started walking to the door, but I clearly didn’t need any help. I looked back at Jo and she gave me a wink. I glad she didn’t mime giving a blowjob as it was going to happen soon, or Steve might pass out from lack of blood to the brain. We walked into the corridor and the clipping of my heels made me very happy, especially as I was holding onto Steve’s arm. I stopped him when we turned a corner into a small alcove and put my finger to my lips so I could listen. Silence.
“Kiss me.” I told him, and he did. We were on school grounds, everything I was wearing were women’s clothes, we were in public and making out. I couldn’t stop myself and he didn’t stop me either as I put my hand in his trousers and took his very hard cock out. I stroked it and crouched down to suck him, but I could feel his orgasm rising very quickly and I had barely licked it when he came, shooting over my face. I couldn’t believe, my first facial happened on school grounds, and I don’t have any tissues or anything to wipe it off with. The nearest toilets meant walking out of this block and across a courtyard with cum on my face.
“Come on,” I told him, “I need to clean up.”
And I took his hand and we walked out into the courtyard and the 100 metre walk outside to get to the toilets. I could feel his cum on my face as we walked together in silence, holding hands. Going into the other block, we headed towards the toilets and he let go of my hands as I was about to go in. “Oh, the girls are over there!” a voice called out. I looked up and it was one of the custodians pointing to the girls’ toilets. They must have seen my heels and just assumed, so while Steve waited outside, I went into the girl’s toilets at school for the first time. In the stall I wiped the cum from my face, lowered my trousers and sat down to have a pee. Once I was cleaned up, I went out and Steve wasn’t there, but then I heard the taps running in the boys’ toilet and he came out shortly. I guess he needed to clean up as well. He took my hand and we started to head towards the gate and now he was coming down from his orgasm high, he let go of my hand, explaining we were still on school grounds. I wanted to walk all the way home in the heels, but I had never walked this far in them before and I really wasn’t used to it, so not far from the school gates I had to change them. At least Steve was ready by the time we got back to mine and while it was only a quickie, I knew he needed it and I was more than ready to let him have me.
Tuesday after school I was once again at Jo’s and Martin’s working out to an exercise video, but this time she was taking it a bit easier while making sure I kept the aerobics going as usual. Jo was telling me what would be happening over the next two months as we rehearsed the show. While the schedule hadn’t been worked out, I was going to be expected at each rehearsal as I had a lot to learn. Tomorrow the cast list and roles would be formally published, so everyone will know what I am doing, and the rehearsals start the following week. Jo was being given this week this to give me some training and I was expected to report any bullying I got, although she knew that would make it worse so suggested I make sure I am always somewhere a teacher is to protect myself. Martin suggested I maybe not wear what I would like to for a couple of weeks from now on and that just made me feel a bit sad, but Jo sad she would arrange hair extensions for me to wear rather than a wig so it can be styled and feel more like me than wearing something that will just make me sweat a lot. The story for when I got home today was that Jo introduced me to makeup. I managed to finally corner my sister as well when I got home without mum hearing us. She admitted she told mum about the show as she was so surprised but hadn’t told her anything else. At first I didn’t quite believe her but as we carried on chatting I realised she really hadn’t. We talked a bit more about what was going on and I told her I was still dressing a little bit but couldn’t work out if it was because I liked looking like a girl or something else, or maybe it was just a sex thing. Like her and her boyfriend, we both sometimes thought we loved them and other times were just using them for the fun we could have with them, but we both agreed in the end that Steve was just a crush that I was getting to enjoy a lot, and that whenever it is over I will heartbroken, but more than likely for him as with most boys, I was just somewhere for him to get his dick wet.
When I arrived at school the next day, I walked past the drama studio and saw that the cast list and roles were up on the wall and some people were looking at it. No one paid me any attention yet, but I wasn’t looking forward to PE later on as by then it would be around the school. Sure enough, when I got to the changing room later that day, everyone knew as it went very quiet when I walked in. There weren’t any comments, but while I was in there no one changed, and no one said anything. I kept my back to them and got out as soon as I could. I was the last picked for cricket when normally I’m just one of the last ten or so, and I asked the teacher if I could finished early to get changed before anyone else was in there and he nodded, saying nothing else to me. I was showered, changed and got out of the room before they finished, walking away as quickly as I could hoping to meet up with Nicola or Michael as they finished their class. Instead, something really surprising happened. As I was walking along the corridor away from the changing rooms, the girls PE class was coming back and I was stopped by a girl called Sarah. “Hiya, I hear you’re going to be one of my Pink Lady’s!” She was smiling as she said it and there was no meanness in her eyes. Sarah was going to be Rizzo. I admitted I was and hoped I wouldn’t make a fool of myself of her. She touched my arm to reassure me and said, “Don’t be silly, I saw you sing at the second audition and think you will be great. Us Pink Ladies were going to have lunch together and I would love it if you could join us? We’ll be out of here in about 20 minutes, will you wait?” Sarah asked me. She seemed really genuine and I definitely wanted to, but didn’t want to wait here for that long with no teachers around and no one to keep an eye out for me in such an exposed area. Sarah realised I was a bit worried and told me to hold on a minute, and she jogged back the way the girls came from the sports field. She came back with one of the women PE teachers, who looked at me, and told me to follow her, so I did. Twenty minutes later in the girl’s PE teachers office, Sarah came and got me, the teachers were lovely and said they would talk to the other teachers and get me out of PE from now on, which is a shame as I did enjoy some of the sports.
I had an amazing lunch break with the other Pink Lady’s Kim and Jodie, as well as Sarah. I thought they might be a bit mean as they were a little bit older than me and also the ones who always do these shows at school. Sarah wants to be a singer when she leaves school, Jodie likes acting as it’s fun, but wants to be an engineer and Kim doesn’t care what she does. After explaining that Miss Reeves is helping me this week to at least give me an idea of how to be a girl, then it’s up to me to keep the role by working at it. The one question I was waiting for wasn’t asked until just before the next lesson which is why I’m doing this. Obviously, I didn’t tell them the real reason why, but just that I thought doing the show would be fun and then that I was given time to decide if I wanted this part and thought why not? Then I asked them if they would act as a man for a school show and they all instantly said yes, just to see what it was like. Point made, and real reason nicely avoided, thank you for the advice, Martin, x.
Kim offered to walk me to class, and I found out from Jo after school that she had asked them to look after me and to make the Pink Lady’s a team by trying to include me in the things they do. I didn’t find out till Friday that this included going to Jodie’s as her mum was making the Pink Lady jackets for us. Jo had given Jodie one of my bras and the chicken filets so that when I was measured it would fit me correctly. They were all surprised when I slipped my arms through the straps and did it up behind my back and just looking at me when I finished. “What?” I said, “Miss Reeves has been helping me. I have a pair of heels at home I have to walk around in all the time as well.” The girls loved this and wanted to see me in them, but I pointed out they will see it every time in rehearsals, so you can wait. The measuring for the jacket was a new experience, having a tape measure go round my bust was strange and being told by Jodie’s mum that maybe I should go up a cup size as it would look better on me. I asked her a bit more about this and she said she would make the jacket for the next size up in case I decide to.
I mentioned this to Jo the next day and Martin thought it would be a good idea. Jo said she would pop out to the store to see what there was and I was to keep practicing walking in the heels and the pencil skirt and the restricted movement. It was funny chatting to Martin while walking around and strutting my stuff, sitting and crossing my legs and just getting used to moving in the skirt and heels. Martin got up to make a drink and asked me if I wanted one and I asked for a cup of tea. In their kitchen they have a breakfast bar with those swivel stools, and I went to sit on one while we chatted as the kettle boiled, but in the pencil skirt couldn’t get on it. Martin walked to me, put his hands on my waist and picked me up effortlessly and placed me on the stool.
O.M.G!
I giggled. I felt like I creamed my knickers at that moment, the teacher the girls crush on just picked me up like I was a plaything. The teacher who with Jo I gave two erections. The teacher who pressed his erection up against me and I pushed back on it. No, not a teacher, Mr Christian is a teacher, Martin is the boyfriend of my friend, and she thought it was funny we gave him an erection. That was who picked me up like a plaything and made me cream my knickers, the man who I’m sitting here squirming for as I realise, I want to get to know that erection, I want to feel it again, I want to taste it, I want to feel it in me. He smiles at me as we wait, and I smile back. I look him up and down.
Why am I thinking this! Ok, this is new to me. I like Steve, I like having sex with Steve but that’s because he was attracted to me when I was wearing lingerie. Martin I fancy and I fancy him a lot. It was him I was thinking about when Steve was last inside me, him I was thinking about when I was teasing Steve in the drama studio. I need to work out what I’m going to do here. I let my heels dangle from my toes as I sit there looking at him.
“Stop flirting with me.” He says. “What do you mean?” I ask back. He gives me a smile that melts me and says, “You know what you’re doing.” I bite my lip and look up at him from under my lashes. “What am I doing?” I ask. Oh god, this is amazing, please let all flirting with men be like this.
“Can I ask you something?” I say to him. “Sure, what do you want to ask?” he replies. I pause for a bit, do I really want to say this and spoil the moment, is the fantasy better that what might go wrong? “It was something Jo said.” I say, I didn’t want to mention her name in case it broke the spell, but Jo is my friend and I know I am flirting with her boyfriend, but I also need to know this. “She said that we both gave you an erection and I wanted to know if I had caused some of it?” I look away, embarrassed. I was stupid and shouldn’t have said it but I did and now it’s all over and I’ve ruined it. I can feel him moving closer and now I’m scared. I feel a finger go under my chin and gently lift my face to look at him. Oh, he is so handsome, so gorgeous I just want him to kiss me. It can’t happen, it mustn’t happen.
He looks me in the eye and says, “Yes.”
“Can I ask you something?” I say to him. “Sure, what do you want to ask?” he replies. I pause for a bit, do I really want to say this and spoil the moment, is the fantasy better that what might go wrong? “It was something Jo said.” I say, I didn’t want to mention her name in case it broke the spell, but Jo is my friend and I know I am flirting with her boyfriend, but I also need to know this. “She said that we both gave you an erection and I wanted to know if I had caused some of it?” I look away, embarrassed. I was stupid and shouldn’t have said it but I did and now it’s all over and I’ve ruined it. I can feel him moving closer and now I’m scared. I feel a finger go under my chin and gently lift my face to look at him. Oh, he is so handsome, so gorgeous I just want him to kiss me. It can’t happen, it mustn’t happen..
He looks me in the eye and says, “Yes.”
Martin leans in towards me I know he is going to kiss me and I should move away, but I don’t. His lips brush mine ever so gently as he gives me a gentle kiss and I close my eyes. I want to devour him but know I mustn’t, this wrong on so many different levels. Our lips move gently, but neither of us opens our mouths to let our tongues explore. I suddenly realise this is the most romantic kiss I’ve ever had and that he is moving away from me but keeps both of his hands on my arms and I notice for the first time my hands are on his shoulders. We look into each other’s eyes, and he is smiling gently at me. I seem to suddenly snap out of it and try to slide off the stool and his hands move to my hips and helps me down and I try to walk away but he takes my hand, not roughly, but enough to make me stop. I look at him and say, “This is wrong.”
He keeps holding my hands and keeps smiling. Grrrrr! Why does he have to be so handsome and why do I know that even though this is wrong I don’t want this to stop. “Why?” is all he says. I try to get the thought of the kiss out my head and point out I am 14, but he just says so if I was 24 and he was 35 would that be wrong? He walks me over to the sofa and we sit down, still holding hands with his thumb gently stroking the back of my hand. “I don’t know, I mean yes and no, but you know what I mean about this?” I tell him. He puts both of his hands on mine and tells me that Amy doesn’t go to his school, Amy is a friend of his and Jo’s. I point out Jo is my friend and It’s wrong to kiss my friend’s boyfriend. He smiles at me gently and says, well if that’s the problem then it isn’t really a problem and for the first time I learn about open relationships and that Jo has a regular lover and so does he. He picked up a digital camera, turns it on and starts showing me pictures of both him and Jo with other people clearly being intimate with them but not having sex, just naked togther, just kissing and being very handsy while smiling. This is a lot to take in.
“I don’t want you to do anything you don’t want to do.” He tells me, knowing full well what I want to do, and I can’t help but smile as I think about it, sneaking a look at him. He is looking at me and smiles, then leans towards me again and this time I pull him towards me as we start kissing. Oh my god this is amazing! Steve is never this gentle and romantic and I knew I needed to draw some boundaries, so I break away from the kiss. “Ok,” I tell him, “We can kiss but nothing else.” He nods as we start kissing again. Our hands were caressing each other as and his bum is so taught and just amazing to hold. I feel one of his hands run down my legs and he takes off one heel, then the other and runs it back up my leg going as far under the pencil skirt as it would let him. He is laying on top of me and once again I feel his erection pressing against me and I giggle. He tells me he is sorry and puts his hand down his trousers to move it so it’s less uncomfortable for both of us. Ok, so my hand didn’t take long to reach down and have a feel and it was much, much bigger than Steve and all I could think was will it fit in my mouth and will it hurt going into to me? Martin breaks away from the kiss and pulls me to my feet, lifting my skirt up my legs between kisses telling me he wants to be able to stroke my legs. I look down and see that it would crease the skirt so I reach behind me and start to pull the zip down, but he stops me, and takes over removing my skirt. He gently lowers the zip while kissing me and it hangs on my hips, before he slowly starts working it over them and it falls to the floor. I’m standing in front of him in a thong and hold ups and he pulls me to him and his hands run down my back, heading for my bum as he presses his erection against me as we kiss. I lead him back to the sofa as I want to lay back and be kissed with him laying on me, caressing me, and as lay down one of his legs goes between mine. We keep kissing and caressing each other and I don’t know when it happened, but both of his legs were between mine and he was rubbing his erection against me while I was pushing back against it.
I stop and push him up a little, but we both keep the pressure below. “Well this isn’t fair!” I tell him. He looks a bit confused for a second, so I say I’m in my underwear, why isn’t he? And before he gets a chance to say I start pushing his trousers down at the back and he lifts his hips. I run my hands around his waist, and undo his trousers, pushing them down. I can see the clear outline of his erection in his underwear as we both work to get his trousers off. Finally, they are on the floor next to my skirt and I decided to take his tee shirt off him as well. Once it’s off he looks at me and says, “Well this isn’t fair!” and I giggle at him as I start to take my jumper off, being careful not to dislodge my wig. We go back to kissing, caressing and rubbing against each other but now feeling each other’s skin as we kiss. I keep thinking this is so wrong but just don’t want to stop. I’m worried where it might go knowing full well what the next step is, me pulling his underwear down, so I just decide if it’s going happen I may as well do it now. So I run my hand down the front of his body and he lifts up from me as my hand just goes in and wraps around his hardness. He is huge, or at least bigger than anything I’ve previously experienced, which isn’t a lot to be fair, but still, I’m holding Jo’s boyfriend’s cock in my hand, stroking it slowly, and thinking about all the other girls at school who would love to be where I am right now. Screw it I think, and push his underwear down and it ends up on the floor as we keep kissing and now I am very aware that there is only a thin bit of cotton keeping him out of me. He adjusts his position, and my legs open further as we keep kissing. I feel him pressing against me and I know at this point it’s going to happen, no matter how much I might try and pretend to myself I don’t want this, I really do want this, and we both know we want this. I can feel the pressure in my own thong as I strain to get fully hard to match Martin, but trapped and driving me even crazier as he presses against me, trying to get past the cotton barrier.
It’s too much for me and I finally say it, “Please get some lube.” He smiles at me and reaches across to small table and opens a draw. Wow, I think. This isn’t KY jelly anymore but something I’ve never felt brave enough to buy, real lube. I take it from his hand and start putting it on him. He goes to pull my thong down, but I shake my head and he knows I just want it pulled to the side, so he kneels up with his slick hard penis pointing at me and I see it properly for the first time and feel scared. Martin takes the lube from me, puts some on a finger and pulls my thong to one side as he fingers me slowly. My eyes roll back into my head as he works me gently, first with one, then two and finally three fingers. I can feel him touching somewhere and I am on fire and I think he senses it and his fingers come out of me and I am desperate for him to put something, anything in me. He kisses me and I feel him working to find the hole his dick is trying to find, so I reach down and guide him to where we both need him to be. I gasp as he pushes in and feel myself open for him. He is big, much bigger than I am used to, so he goes slowly, sensing both my lust and my pain, so he is in me, moving gently and leans down to kiss me. I start to relax as he slowly moves into me as my body relaxes and he is in. I have never felt so full, so held open and so happy as this moment.
We made love on the sofa in the flat he shares with his girlfriend, my friend and also my drama teacher as my English teacher is in me. I felt no guilt, I felt wanted for who I was rather than wanted for being someone who will have sex with them. As we both started getting close to orgasm I was hoping we would both cum together to feel it, but he made me cum just before I felt him cumming inside me. He thrust fully in me and we kissed as he came. I opened my eyes to look at him and see him cumming, but in the doorway looking at us was Jo. My world crumbled as I could feel Martin cumming in me. From where she was standing she would see him going into me. Once he finished and relaxed and was kissing my neck and I was looking Jo in the eye while her boyfriend was in me. There was no expression on her face as she looked and finally Martin looked at me, saw my expression and then Jo said, “Well that looks like you are both having fun.” It made Martin jump which made him go even deeper into me which made me moan and made Jo laugh.
Oh no, oh no, oh no was all I kept thinking this is horrible. Why do I keep getting caught while having sex? Jo walked across the room and knelt down next to us, her face inches from both of us. Still her expression was blank and still Martin was in me. Suddenly she started to laugh and so did Martin, with each roll of his body twitching him inside me and I couldn’t help it but I moaned again. Martin gave me a kiss, and Jo said she’s not mad, she knew he fancied me after the first visit but neither knew if anything would happen, especially with one of their pupils. She then said to me, “He’s good, isn’t he?” I could only nod. She gave Martin a kiss which I fought was funny as he was still inside me, I was still on my back with my legs spread under him and it was just so silly. She smiled and gave me a quick peck on the cheek and said she would get us both a drink. Martin told me to wrap my arms and legs around him and he started to stand up, still in me and while not as rigid as before, still quite hard. I was worried I would push him out and his cum would drip on their carpet, but he held me very close and carried to their kitchen area and sat my bum on the stool. Jo smiled at me as she handed me a can of coke and said, “The seat is exactly the right height, isn’t it?” I blushed and tried to bury my head in Martin’s chest, just feeling so embarrassed about this. It was even weirder sitting there with him in me still, moving back and forth in me slowly as we talked about what happened. We all promised not to tell anyone, as this had just got very serious, so we did a three-way pinkie swear to tell no one, ever. Plus, they pointed out, if no one knows then this can carry on, when someone knows it is all over for each of us in the worst way possible.
We carried on chatting away, with Martin still not pulling out of me and when I asked why he hadn’t yet, he just said he wanted me to get used to him so each time will be amazing for both of us. I gave him a kiss and my eyes then went wide. I looked at Jo and she asked if I was alright. “Yes, I just wasn’t expecting to feel this right now.” I told her. “You mean happy?” she asked, and Martin said, “No, I’m getting fully hard again.” Jo laughed and I started to as well, and Martin looked like he was heaven as I felt myself tighten up around him and he literally sprung to full hardness in me. I kissed him then and felt him pick me up again. Jo went and sat down as he took me to the bedroom, and I went to bed with him.
When we both walked back into the living room, I was embarrassed again as my clothes were now over the back of a chair, so I got dressed as we all chatted. Jo told me a bit more about the play and the plan for the next couple of weeks and was really pleased that the Pink Lady’s were being friendly to me. When I finally got changed to go home I saw how much a mess my makeup was after a huge amount of sex and I could feel some of Martin’s cum running down my leg inside my trousers and I have to admit I loved every second of the walk!
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Monday at school was fun, everyone knew what I was doing in the show, but the other Pink Lady’s were looking after me. Steve was being a bit distant again, despite us managing to meet up the day before. Come lunchtime we had the first show meeting where Miss Reeves explained what was expected of us, that we were meant to be taking seriously and she has no problem kicking anyone out of the show if they didn’t behave not just for her but everyone. Jo handed out pages to everyone by calling out our character names and when she called Marty I got up and walked across. “Stop.” I stopped and looked at Miss Reeves looked at me and said, “You need to wear the heels every time you are in here for rehearsals. Put them on.” I walked back to my bag with everyone watching me, and sheepishly took them out of my bag, along with the tights socks. I took my shoes and socks off, put the tights socks on and slipped on the heels and stood up. I walked across to her, but not like a girl, more like a boy wearing heels. As she handed me my pages, she said, “Ok, but you need to work more on how you should be walking. Sarah, can you help him please?” Sarah got up as I got back and we went to the other end of the drama studio and gave me some lessons in how to walk in heels. I needed to make it look like I was slowly getting better, but every so often she was directing me and saying I was getting it. Twenty minutes later we walked back to the rest of the group and I was walking like a girl in them as we both sat down with the other Pink Lady’s. I then pulled my legs together and crossed them and each of us was sitting there in the same pose. Miss Reeves looked across and smiled at us as the background characters left and the last half hour was the Pink Lady’s and T Birds as Miss Reeves explained that we were expected to be at every rehearsal as there would always be something for us to do.
When it came time to go to our next lessons, I accidently on purpose forgot I was wearing the heels and walked out the drama studio and into the corridor with the Pink Lady’s. A few more steps and the very distinct sound of my heels in the corridor. I looked at them and each smiled at me, and Jodie said, “Honey, own it.” So, I did, and they walked me to my next class. Once in there I did change my shoes but saw no reason to put my socks on. After the last lesson I made my way over to the studio and slipped my heels on as soon as I was through the door, and we all rehearsed the first scene with our pages and Miss Reeves reading out any other character. We also had to perform a scene with our on-stage partners to see how we behaved together, and while my ‘Sonny’ was a bit nervous, Miss Reeves pointed out to him that the most he would have to do is hold my hand so don’t worry. We did ok, it was a bit awkward for both of us, but we got through it and we both felt relieved. We did have to hold hands on stage in the scene, but as we both had to say ‘I love you’ several times it helped us both get over the weirdness of him needing to say that to a boy in heels. When we had all finished Miss Reeves suggested that we make we sure we get together whenever we can, in pairs or more to work on our parts and to make sure we started learning all the lines. We all walked out together, and I kept my heels on and walked as far as I could until I needed to take them off, with Sarah holding my arm as I changed them. At home, my calves really ached and both mum and my sister thought it was hilarious saying now I should understand why women are always complaining about their feet at the end of the day.
Tuesday after the rehearsal, Miss Reeves asked me to hang back for a minute to chat, and I did wonder if she was going to give me a lift to hers so we could work out and that was why. It wasn’t. She told me I wouldn’t be able to do that during the week for a while now, but that tomorrow she was going to get me to wear a wig in rehearsal and the day after was going to give take me into the store and give me a bra as well. She then surprised me by saying on Saturday while I was a busy with Martin, she had got the next size up of chicken fillets and they were in the store ready. So the next day at lunch time rehearsal I was given a wig to wear to ‘help the others visualise me better’ and the day after at lunch time a bra was added with my boobs in them. By Friday I had decided it was too much of an annoyance to take the bra off between rehearsals, so I left it on. By Wednesday the next week I left the chicken fillets in as well, but not the wig as it just looked a bit silly coming out of the store each day. I even walked home in the bra and left it on when mum came home. She noticed it straight away and told me that most women can’t wait to take them but did compliment me on my improved posture. On Saturday I told mum I was meeting up with one of the Pink Ladies, put my bra and thong on, a pair of jeans and carried my heels downstairs. She saw me carrying them and told me to put them in bag, and I pointed out I was going to do that and headed over to Jo and Martin’s. When I got there, I headed off to get changed and came out to Jo sitting at a table working on a model of the stage and clearly very busy. Martin looked at me, smiled and said, “Come on, let’s get out of the way.” And we headed to the kitchen, then as we were told we were making too much noise we moved to the bedroom. Jo then had to come in and ask us to have sex a lot quieter please, so we kept the moaning down as much as possible. Today I managed to give him a blow job, I’m not sure I was very good as I couldn’t get more than half in my mouth as he was so much bigger than Steve, but he came and I swallowed so I guess it worked out ok.
At the end of the day after I had cleaned up, Jo did drive me most of the way home and apologise for us not spending a lot of time together today, but I understood and we hugged. The next day I really was meeting up with the Pink Lady’s at Sarah’s house and her mum and dad kept telling me how brave I was as I sat there in my heels and bra. Her dad owned a hairdressers’ and asked me what I was doing with my hair. I explained about the wig and he offered to give me hair extensions as he was going to helping for the show anyway. I said I would need to think about it, but he said it wasn’t a problem at all, and would be a lot more comfortable. The girls all wanted me to do it, and I knew I did as well, but I hoped that didn’t show. We were meant to go over some lines, but in fact we ended up just having a sing along to the film and playing our parts. I mentioned to my mum the offer of hair extensions and she wasn’t against it, in fact she said it made sense but was worried about me being bullied. “Mum! Everyone is looking after me and making sure I am never alone and always near a teacher. I can see the looks and feel them judging me, but I want to try this as I may never get a chance to try something like this again.” She gave me a hug and said she was ok with it, so long as I was fully aware of the risks I faced.
The next week at school was pretty much the same, but Steve was definitely being off with me. Well screw him, just because he hasn’t been laid for a week, he will have to get over it. Besides, I knew we would have Wednesday evening together if he wanted it as both my mum and sister were going to be out. When I managed to tell him this, he looked at me and said ok, but not if he was going to come round or not. In rehearsal I told Sarah that mum was ok with me getting extensions and she said she would speak to her dad but asked for a small clipping of my hair to match the colour. I was worried she was going to take a huge chunk, but it was only a little so biggie. The week went along like before and I don’t know if people were getting used to me walking around the school in heels and a bra or not, but I still hadn’t faced any problems other than looks. On Wednesday evening I wasn’t sure if Steve would turn up, so I kept my heels and bra on as the pizza arrived and the delivery guy called me ‘miss’ which I thought was nice. And then Steve walked to the door right behind him, and almost snuck inside trying to hide his face. He wasn’t very talkative with me, in fact, he was a little rough and clearly needed to get off and used me to do it. I went to kiss him and after a quick peck on the lips, he pushed down and to my knees to give him a blow job. He didn’t last very long but it was clear he needed it and we shared the pizza. Once it was over it I tried to snuggle up to him but it was clear he wanted to get inside me and after very little foreplay, I was bent over the table and he was thrusting in me. It was still nice, but I was being used and I let him use me as I didn’t want to lose him. After he had finished and we cleaned up, he then gave me a hug, a quick kiss and said he had to go, leaving me there feeling really used, but I wasn’t going to let him know that his behaviour had hurt me. I almost cried myself to sleep at feeling so used.
I was as over it as I could be the next day at school and when I saw Steve I tried to act as we normally did but he was still a bit cold towards me. Fine, at least I have a real man who wants to have me and treat me like a woman! The week carried on and this Saturday I was going to meet up with the Pink Lady’s in the afternoon to rehearse a bit and then go out in the evening to see a film together. My visit with Jo and Martin on Saturday was shorter than usual and included me rushing to get cleaned up to meet the girls. This time we really did rehearse at Sarah’s learning our parts for Summer Lovin’ and the talking parts before and after. At four we headed out for the film but instead stopped in at her parent’s hairdressers, I thought just to say hi and Sarah to get some money. Instead, her dad asked me if I was ready, and then it was sprung on me, it was time to get the extensions. I thought this would happen much later, but the girls said they agreed I should get used to it now. So I sat in the chair for an hour or so, as they were fitted and it was explained to me they should last until the show if I look after them and that new ones would be put in the week before the show. We then headed back to Sarah’s house with my new long hair coming down just below my shoulders. I had to keep tucking it behind my ear as we walked to keep it out of my face but other than a bit of tightness, it was a lot more comfortable than wearing a wig and a lot less hot as well. I had thought we were going to the cinema but instead we watched all watched a film together as the girls taught me even more about hair to look after my hair. When I got home mum thought it was funny it was sprung on me, but that Sarah’s parent had called her and talked about it. Sleeping with long hair was weird, and in the morning it took me a while to brush out the tangles.
Sunday I was at home, rehearsing by myself with the CD we had been given and doing my homework. I hadn’t done any during the week so had a bit to catch up on so just did some singing and dancing to give myself a break from the books.
Monday for school I brushed it out and put it in a ponytail, but when I met up with Nicola on the way she loved my hair. I think I got a lot more looks and Martin, I mean Mr Christian snuck a wink at me in the hall which just made me blush every time I thought about it. Lunchtime rehearsal, it was suggested I tie the ponytail higher up on the back of my head and I really liked the way I could feel it swinging about. For one of my scenes, Miss Reeves suggested I let it down so I could play with it, and it definitely made me feel more feminine and Jodie told me after it really looked like I was flirting with the stand in for Vince Fontaine and just looked amazing when I looked up at him. I put the ponytail high up again for the afternoon and walked through the school in my heels and bra with the girls truly feeling like one of them for once. On the way to the evening rehearsal, Sarah and Kim took me to one side and on the way said to me, “You really need this.” And they both started to put eyeliner and mascara on me. One again I let my hair down and in the scene with Vince Fontaine I really felt a lot better and Miss Reeves and everyone said it looked like I was starting to get into the role now and that whatever I was doing I should keep up. Miss Reeves came over to the Pink Lady’s and asked them if it was their idea to give me some makeup, and when they said it was said, ok, teach him how to do makeup so she can do her own for the show. I loved how she mixed up the pronouns! On Tuesday at lunchtime rehearsal, they once again did my eyes and gave me my own eyeliner pencil and mascara and I didn’t bother taking it off for the afternoon. I didn’t care, people knew I was in the show, and I even kept my heels on in class and sat by the side during PE wearing them, playing with my hair while the boys did sport stuff. At least Steve was looking at me more now, even if he was basically ignoring me.
That evening rehearsal was the first time I went to the storeroom and changed into a skirt for the session. It was the girls idea and wasn’t a costume skirt, but a discarded school uniform skirt. I suspect that Jo had picked it up at a charity store as it just happened to be my size. Strangely, this rehearsal us and the T Birds didn’t have much to do as it was making sure the background chorus knew what we were doing so they could learn their parts, so I spent most of it sitting down with the girls. They were teaching me how to move in one, how to sit in one and so on. We went out to the toilets and as we got there, I suddenly remembered what I was wearing and didn’t want to go into the boys toilet. I knew the school was empty, but I knew dressed and looking like I did it just wouldn’t be safe for me. Jodie saw me hesitate and took my arm saying, “Come on, Pink Lady’s do everything together!” And with that I went into the girls toilet with them. There were four stalls and we each took one. I lifted my skirt, dropped my knickers and sat down to pee. I was glad I decided to not to wear a thong today, if the girls had noticed I think I would have died. I wiped when I finished and went out t join the girls, making sure my skirt wasn’t tucked into my knickers as instructed and joined them at the mirror as I washed my hands, then copied them touching up my makeup. Sarah looked at me and said, “See, that was no big deal.” As we walked back, this time we all went into Pink Lady mode and really worked it, and Mr Christian walked out of the staffroom. He laughed when he saw us and told us not to keep Miss Reeves waiting and the other girls went really shy around him, and I realised they all fancied the man who has been fucking me! Now that made me feel really good. The next day at lunch rehearsal, I once again went into the skirt and did my makeup. The session went really well and I was mainly dancing along with a little back up singing, but it was so much more fun being much more in role. Of course during a break I needed a pee and Jodie noticed and said, come on, we’ll go together. So in a skirt, with my hair down, makeup and a bra we walked out into the corridor and to the girls toilet. I walked in with her and I’m not sure if anyone noticed it was me, but I felt like everyone was looking. Jodie really helped to keep me calm and said it was no big deal, this is a role you’re playing, be Marty. So we went in, got in the stall and while I was peeing some other girls came and talked about Mr Christian and how much they fancied him, how they were trying to work out if the bulge in his pants was all him. I was literally dying but couldn’t keep hiding in there as I had heard Jodie finish, so I had to go out. I smoothed my skirt, opened the door and the other two girls looked at me in the mirror. One instantly knew who I was and whispered in her friends ear and just said “Really?” She looked at me as I touched up my mascara next to Jodie and finally the girl asked me. “Are you the boy playing the girl in the show?” I mumbled a yes and saw Jodie giving me the eye saying, ‘be Marty’, so I straitened myself out and look at her and said, “Yes, I am. Why?” She looked me up and down and said, “Ok. I like your hair, but you really need to get a better skirt for school, that is so old.” I looked at what she was wearing, and yeah, mine was nothing like what she was wearing. Hers was shorter and tighter, mine was longer and more flared. I had noticed, but beggars can’t be chooser they say. The other girl didn’t look impressed I was in there, so I turned to Jodie and asked her, “I’m really glad I don’t have to kiss him in the show, I would die with everyone watching me.” Jodie caught up very quickly and said, “But he is really cute, you said so yourself that you could fancy him, and that stage kiss you did was something else!” The other girls left us and we both giggled away when the door opened and another girl came in as we made our way back. I wasn’t brave enough to keep the skirt on in the afternoon but wore it again that evening. The next day Jodie handed me a carrier bag with a smile when I arrived at school and when I looked in there was a more recent skirt for me to wear. I took her to one side and hugged her, and I felt even better at lunchtime and we even had a little walk around the school when we had a short break. All the Pink Lady’s told me I may as well wear it in the afternoon as what was the point in changing back as it only takes more time. Kim had a spare pair of uniform tights she gave me and while I was tempted, I just couldn’t. But in the evening the four of us went to Miss Reeves and before I even opened my mouth, they all starting talking at the same time. Miss Reeve held up her hand and said, “Stop! One at a time please and be quick, we have a lot to do.” They all looked at me, but I couldn’t speak, so Sarah as our unofficial leader said it. “We think it would be easier if he stopped changing back for forth in the afternoon and just wore the skirt for the rest of the day.” Miss Reeves looked at them all and me. I looked back both pleading her to say yes and also pleading her to say no. In the end she just said, “Let me think about this, I will need to talk to people.”
I changed to go home and when I got there mum asked to see my new school skirt. I just looked at her and she said, “Miss Reeves told me that the other girls might be bullying you into wearing one in classes and we wanted to make sure they weren’t.” I told her that wasn’t it, it was just that it meant I lost time at the start of both rehearsals, and they were trying to help, plus it was really helping my performance. She asked how I felt about it and I told her about my walk around the school at lunchtime and that although I got a few looks, it probably had more to do with them not me seeing before. She said she would think about it.
In the morning mum handed me a letter to give to Miss Reeves before lessons and told me to have enjoy my day. As usual I got changed in the storeroom and Miss Reeves had a quick word with me as I came out of the room. “You can leave your trousers in there and pick them up at the end of the day if you like.” And she gave me a quick wink. I looked at her and she nodded and told me to tell the other girls. They all squealed in delight, and I found myself joining in until we were told to be quiet. At the end of the session, Miss Reeves called everyone together and reminded them of her rules. She also said that I would from now on in the afternoon be presenting as a girl as it was easier than changing back and slowing everyone down, they were to report any bullying of me for it, and generally be nice and that the whole cast needed to look out for me as that is what theatre people do. I could feel my ears burning bright red as I sat there on the floor, trying to keep my skirt from showing my knickers. She then said something that really surprised me. “And finally, I spoke to our Marty and we agreed we can’t call her D_____, so when she is dressed like this I expect everyone to call her Amy. There isn’t another Amy in the cast, and I felt like it was the easiest name to use. So everyone say hello to Amy.”
There was a chorus of hello’s and people saying Amy and it truly felt wonderful. The pink Ladies walked me to my next class and I felt very nervous. They each hugged me before I opened the door, and when I walked in everyone stopped to look at me. The teacher gave me a nod and I took my seat next to Steve, who was sitting there wide eyed. I think he wanted to get away from me, but I had already seen he had an erection, so it wasn’t going to happen. The teacher then spoke to everyone in the class, literally repeating what Miss Reeves had said. He then reminded me that he understood I was wearing those shoes for the show, but I would need more suitable shoes if this will be the norm from now on. I said, “Yes sir” in my girl voice which I think surprised everyone. Everything in class settled down after that and Steve was still not talking to me, but he also couldn’t stop looking at my legs. I decided to tease him and let the skirt ride up and talked to him like normal until he could see my pants with the little hearts showing clearly through the tights. I waited till he had a good look, apologised, and pulled it down hiding them. We were pretty much at the back of the class and I thought, ok, see if you can keep ignoring me, so I put my hand in his lap, and just gently stroked his erection in class. I wanted him to suffer and made sure he stayed hard all through class, and while I only got single words out of him, I never got any of our usual banter. Mind you, I was teasing him a lot. When the lesson finished, I got up and left him saying I would see him later and walked out, leaving him there suffering and trying to hide it. In the break, Nicola was waiting for me and gave me a huge hug, saying that they had been told about me and everyone was under threat of severe punishment if they did anything to me. I felt really touched and Miss Reeves must had done some good work with all the teachers.
When I got to PE, ready to sit on the sides as usual with the others who for whatever reason don’t take part, the PE teacher stopped me and said I would be too much of a distraction, so I can sit in the girls PE lesson. I spun on my heel, really proud at myself for doing that and walked back to the where the girls were. The girls PE teacher smiled at me and said it was nice of me to join them, showed me where I could sit, and whispered that I could use the toilets in the girls changing room while they were in the lesson if I needed it. During the lesson the girls played Netball and the teacher told me what they were doing, let me know some of the rules and when the girls went to get changed told me a bit more about what had been agreed. The teachers knew I had already used the girls toilet and while it wasn’t a big deal as no one had complained, she said if someone does I will have to come to the teacher’s lounge and asked to use theirs. Jo was really looking out for me. After the end of day rehearsal, I did get changed back to go home.
The next day, the Pink Lady’s and Nicola were disappointed that I started the day as a boy but I pointed out that it might freak a few people out if I did that. After school I decided it was too much hassle to change back and wanted to just go home in my skirt, but Miss Reeves pulled me to one side before I left. She pointed out I was wearing heels and had great legs and probably wasn’t used to men looking at me the way they were going to and asked me to be careful and not walk too far, so I got the bus. Yes, I definitely felt a lot of men on their way home from work looking at the schoolgirl in the short tight skirt in high heels and it felt horrible! The man I sat next to one the bus was openly looking at my legs and I realised he was playing with himself under his jacket as he looked at me! Gross, he must have been in his 50’s and I felt a bit dirty over the whole thing. When I got in, mum was home and could see I was a bit upset, and eventually I told her about the bus and the man. She looked at me and said, “Ok, no more heels on the way home, lets go shopping.” And she picked up her bag, handed me one of Bev’s jacket’s and we went to get a more suitable pair of shoes for school. I wore them home and felt at least now I will fit in with the girls. They may not have been as cute as the heels or as nice as the ankle boots I really wanted, but I knew what I was going to do in the morning. Tomorrow I would go to school as a girl for the entire day.
“Ok, no more heels on the way home, let's go shopping.” And she picked up her bag, handed me one of Bev’s jacket’s and we went to get a more suitable pair of shoes for school. I wore them home and felt at least now I will fit in with the girls. They may not have been as cute as the heels or as nice as the ankle boots I really wanted, but I knew what I was going to do in the morning. Tomorrow I would go to school as a girl for the entire day.
The next day I got up early to get ready and mum was surprised when I came down in the skirt and my hair down, wearing some light makeup. She looked at me and asked with her eyes if I was sure. “Mum, everyone knows, everyone has seen me, and this saves time!” She looked at me again and then asked why I had got up earlier than usual to make sure my hair and makeup was perfect if it saves time. I had a little sulk and mumbled, “You know what I mean.” And she looked at me, gave me a hug and said, “You are just like your sister, and I had forgotten what it’s like having a young teen girl going to school. Be safe.” And she kissed me on the top of my head and left for work. I finished my breakfast and with my new shoes felt I could walk in as I felt like I wasn’t really ready to get the bus after yesterday. I bumped into Steve on the way and this time he did talk to me. We had a mini argument about why he wasn’t talking to me anymore and finally I found out was going on. He was a bit freaked about me taking the role and people had been winding him up calling me his girlfriend and then when he saw me strutting around with the girls’ he was annoyed I wasn’t with him, but also didn’t want me near him to avoid the name calling. I got him to agree to not be a shit towards to me anymore and that I wouldn’t spend as much time with him as before, but I hoped we could go back to normal once the show had finished, and I started to walk faster than him with my arms as crossed. I was annoyed. He caught up with me and said, “Look, you know what school is like, but you know, can we still…?” I stopped and looked at him. He wanted to ignore me but still get laid! Men!
I was furious when I got to school and it took the excitement of the Pink Lady’s at seeing me to cheer me up. I almost forgot about Steve until I saw him later. Lessons and rehearsals all went as usual and other than looks and the odd comment nothing special happened. Nicola did catch up with me and gave me a message from Steve that he was sorry and hoped we could make it up somehow. I told her what had happened with him, and she gave me hug and told me that he just needed to calm down and ignore what they were saying, and it would all calm down soon. The next day was Saturday and after seeing Mr Christian a few times during the week, I was really looking forward to seeing Martin in the morning and the Pink Ladies in the afternoon. I borrowed some clothes from Bev and after breakfast made my way over as usual. When Martin opened the door he looked at me and just said wow! I was wearing a denim mini skirt, a sleeveless top that showed a little of my stomach and the boots I had brought when I went shopping with Bev. He scooped me up, we said hi to Jo and he carried me straight to the bedroom. After making love, we chatted about all sorts of things, and I told him about Steve. Martin was amazing and brought Jo in to give me advice. Basically, they said I was being a bit of a bitch for not thinking of his feelings as I had changed in public, but he might not be ready to do that so I should give the space he needs. After leaving to meet up with the girls at Sarah’s, I stopped to call Steve. I used my boy voice and asked to speak to him, then once he was on the phone I went back to being Amy and told him I was sorry for what he was going through, but I will be here for him. He then wanted to see me, but I had to say not right now, the show must go on. He laughed! He finally became Steve again with me, even if only for a little bit, but I felt we might be able to save something. Just before I got to Sarah’s I had to rush into a public toilet as I felt Martin’s cum leaking out of me and running down my leg and couldn’t leet the girls see that!
They loved my outfit when I got there and did a few poses for them, and we did our rehearsals and chatted like girls. Sarah suggested I try a dress on to see how it looked and I took off my top and dropped my skirt. The girls suddenly went quiet, and I was worried that I was leaking more cum and asked them what was wrong. Kim said, “You’re wearing a thong!” And I said, “I know, I put it on.” And we giggled. They then asked me a few questions one of which is why I have a flat front, so I explained about tucking and what I had done and how the thong holds everything in place really well. They asked if I ever wear them at school and I admitted that sometimes I do, but mostly it’s just boring pants with little hearts on as I was worried about boys trying to lift up my skirt. Sarah said, “Well that’s not a problem anymore with the tighter one is it. Come on get the dress on and let’s see how you look.” It was red bandage dress and really fitted me tightly. I absolutely loved it! It felt amazing on me and just felt really nice. Kim said, “You should wear that tomorrow as we’re going to club in the evening. They only sell soft drinks, but it will be a Pink Lady’s outing?” They all started asking me to go and I said I would need to ask my mum and Sarah said, “We have a phone.” So I made the call and mum was worried but I said it will be me and the girls and we will be very safe. She relented and agreed to me going, so after rehearsal here tomorrow, I was going on a girl’s night out.
Chatting with Bev in the morning, I borrowed one of her short denim skirt to go with a tee shirt and a her jacket, pointing out to me I really needed to get some more clothes and said she would take me some charity shops to get some good things, and a lot cheaper than anywhere else. I made my way round to Sarah’s, strutting my stuff in my ankle boots with the three inch heel. Ok, they were Bev’s really, but she was ok with it, but a car pulled up next to me and Kim was sitting the passenger seat with her dad driving, offering me a lift. I jumped in the back and realised I needed to do that as a girl as apart from flashing myself, it was also a bit hard with the heels and I almost fell over. With the girls, we practiced our dance moves and went over our lines, then stopped to have a quick snack and get ready. Kim and Jodie had brought their own makeup and clothes, and I just thought I would get changed into the dress and off we go. But the girls has other ideas, and it involved a full make over for me, starting with my eyebrows being shaped. They plucked at them really carefully and slowly, and it stung a bit but not too bad really. My makeup set was a cheap one from Argos but the girls had a much better selection and helped me find my colours, gave me some smoky eyes and I learnt a lot from them. There was a bit of work done on my hair. I really liked it being straight, but they took some curling tongs to it and gave it a really nice shape, I guess Sarah being the daughter of two hairdressers helps you to learn a lot about hair. Then it was time for us all to get dressed and it felt strange as we all stripped down to our underwear in the room, but Jodie pointed out we are all girls here, so not biggie. Although my eyes did go wide when they changed their bras in front of me. I did look and said I was jealous of them having them as it would be so much easier for me rather than needing the inserts, which then led to us comparing how I felt to them, talking about the size of our boobs and there was nothing felt sexual about it all.
Once we were ready, we headed downstairs and Sarah’s mum told me I looked very pretty and to enjoy my first girl’s night out and we went out to the people carrier and she gave us a lift to the club. As we got close it was already clear there were lots of other teens like us, queuing up waiting for the doors to open so we had three hours of pretending we were older and clubbing for real, but for us it was only from six till nine. We joined the queue and I think I only recognised a couple of kids from our school, but with so many of us in the queue it was hard to tell. Giggling and chatting excitedly the queue started to move forward and we finally paid to get in. We went to bar and finally managed to get a glass of diet coke and we drank them through a straw before we hit the dance floor. I had so much fun, dancing with the girls and having the odd boy here and there try to dance with us, but we were a group, and no one messed with us on the floor! I’ve no idea how long we danced, but we headed to the toilets and stood in the queue with the other girls and finally got in, and it was a lot nicer in there than I expected, but really busy. Finally, it was our turn and two stalls became free and I told Sarah to go first but she took my hand and we both went in one together while Jodie and Kim went in the other. Sarah wiped down the seat, lifted her skirt and pulled down her underwear as she sat down and peed, never once stopping talking to me. She wiped and stood up and it was my turn. She had wiped the seat, so I didn’t, and I pulled up my dress and lowered my thong as I sat down. We kept talking as I peed, took some paper and wiped myself, then realised I had a problem. I would need to tuck again and there was no way that Sarah wouldn’t see what I was doing, so I mouthed a ‘sorry’ to her, stood up and sorted my tuck with Sarah watching me as we talked. I then pulled up my thong and made sure I was secure as I lowered my dress and smoothed it out. She looked at me and gave me a hug whispering in my ear it was ok, she wouldn’t say anything about it.
Back in the club we had got another diet coke and were standing at the side when two boys I didn’t recognise came over and asked me and Kim to dance. I looked at them and Kim instantly said yes to her boy and after looking at Sarah and Jodie, I nodded to the boy and he took my hand as we walked to the dance floor. It was no big deal really, just dancing with him and asking a few questions, my name, where I go to school and so on. After a couple of songs, we stopped dancing and he went to buy me a drink. I was going to walk back to the other girls but couldn’t see them so I stayed with the boy. I thought it made sense to go back to where the girls had been standing against the wall and he chatted to me and when I put my glass down I noticed it looked like he had an erection. What was it with me giving boys erections all the time! Anyway, we chatted for a bit more and he was moving closer and before I knew it, his hands was on my hip and was slowly stroking me. It was a clumsy attempt at foreplay or trying to turn me on, but it was all new to me so I let him carry on. When was really close to me, he leant down to put his glass on the floor and he kissed my leg. I was so surprised I barely moved, so as he stood up he kissed my hip, my stomach, between my boobs, then my neck and it didn’t take an expert to know where he will kiss me next. And that is how the girls found me, making out with this boy whose name I couldn’t even remember with his erection pressing against my stomach and with one leg lifted up and his hand trying to get up the dress and to feel my bum. I looked at them and blushed, but the boy pulled me back into the kiss and I was enjoying it, feeling him rub against me.
I managed to stop him and asked him to get me another drink, and I chatted with the girls as much as was possible in a club with loud music. None of them had an issue with what they saw, and pointed out as far as they were concerned, I was a girl so get over it, and carry on! I danced with the boy a few more times, kissed him a lot more and the slow dance with him was really nice, it felt so romantic. The night finished and I kissed him goodbye while Kim had a snog with her boy. Outside, everyone was making their own way in different directions, and other kids were getting picked up by parents. We were waiting for Sarah’s mum to pick us up and drop us at our houses and then she arrived and off we went, but this time I got in bum first, I had learnt my lesson. I was dropped off at home and opened the door wearing the red bandage dress. My mum saw it and after a chat about being appropriately dressed, she asked me I had had enjoyed myself. As I was leaving to get changed for bed, mum said, “Don’t forget to take your makeup off, although it looks like someone has already tried to remove your lipstick with their lips.” I looked in a mirror and yes, it looked like I had been kissing someone for quite a while. Mum never mentioned it again to me for weeks, but by then my life was already changing.
The next couple of weeks it all carried on as normal and I had a couple more girls night out, and regular sex with Martin and sometimes squeezing in a meeting with Steve, but about two weeks away from the show something awful happened to me. By this time no one was bothering me, sure, there were still looks and comments, but it seemed that everyone had accepted me, so I had no problem walking around the school by myself. I was walking along a corridor and there were only a few others there when suddenly I was grabbed and pushed to the floor, I felt hands grabbing me and suddenly an older boy, a real evil piece of shit was lifting me up and pushed me against the wall, his face right in mine and I was really scared. Unless someone walked right past us, in the little alcove we were in no one would see us. He said, “You’re just a little prick tease, aren’t you? Walking around here like a big deal and thinking everyone has forgotten who you are. Well, I’m going to show what it really means to be a girl!” and I felt his hands going up under my skirt, pulling at my tights and underwear, trying to get them down. I tried to struggle out of his grip and was about to scream, but he put his hand over my mouth and pushed my head back and it hurt a lot. I completely froze, not knowing what was going to happen to me as he got my underwear and tights down to my knees. I tried to keep my legs together to stop my tuck from coming undone, but he kicked my legs apart and I felt myself fall free, too scared to move. Now he was happy I was half naked and he started to take his own penis out. He was hard and pressing against me, he stroked it and stroked me down there at the same time and even though I had frozen in fear, my body reacted to his touch and I hated myself for it at that moment. Suddenly I was free and the boy was on the floor with his own erection pointing up and Mr Christian was standing in front of me, asking if I was ok, but I was still frozen in fear. Mr Christian started to lift my tights and underwear up for me, to help me cover up and I looked at my attacker, laying there knowing he was in big trouble as he put his deflating penis away. Mr Christian told him to get out of his sight, his parents will be called and probably the police as well and the boy run away. Mr Christian, no Martin gently took my still erect penis and gently put me in my underwear, but it wasn’t tucked and there was an obvious bulge. I fell into his arms and the tears came for the first time as he picked me up and carried me to the nurse’s office. I don’t know how long it was before my mum arrived, but Miss Reeves had already visited me and the Pink Lady’s were all there as well. At some point I must have tucked as my bulge had gone so I guessed the girls had made sure I sorted that out.
Mum took me to the doctors and on the way there I was more worried about missing rehearsal and she told me that Miss Reeves had said it was ok, and that Sarah, Kim and Jodie were coming to ours that night for a sleepover as they didn’t want to leave me alone and it was the only way she could get them to agree to go back to classes. The doctor didn’t even bat an eyelid as I walked in with mum, dressed as Amy. She asked how I wanted to be called and if I would like to have my records changed. I nodded. After being checked out physically for any damage, the doctor asked my mum to leave and we chatted for what seemed like an hour. She was amazing and made me feel much better about myself. I made her promise not to tell my mum about me dressing up before the agreeing to the show and when she asked if I was sexually active and I blushed, she just told me she lost her virginity when she was 13 and she wasn’t judging me. I never told her about Martin, but did tell her about Steve, and we chatted about if Amy was something I wanted to forever and it was at that moment I decided that I don’t care what anyone else thought, I like being Amy. She said that I would need some blood tests, but she would see what she could to help and I asked if that meant I would be able to get my own boobs and she laughed and gave me a hug, saying all in good time if that is what I want.
Once at home Bev had run me a bath and sat with me as I soaked to make sure I was ok. Strangely, as awful as the experience was, I felt ok as I had pretty much made my mind up that after the show I was going to carry on being Amy at school. I loved my friends and while I might not want to be an actor, I was loving the chance to do this. Once I put on fresh underwear and my PJ’s I went downstairs and the girls were all there, rushing over and giving me hug. The boy was expelled and there was talk of getting the police involved but I didn’t want that, I didn’t want to be in a courtroom and the boy was gone and apparently lived a fair bit away from me so I wouldn’t see him again. I wanted to move on. With the girls we watched a couple of movies, ate pizza and climbed into our sleeping bags. Before I went to class the next day I had to report to the nurses office and she asked me a lot of questions until she finally accepted I was ok and would come see her as soon as I felt I needed it. I made my way to class, taking a detour to where it happened so that I wouldn’t feel scared being there in the future. I stopped and looked at the little alcove and the floor where I last saw my attacker, laughing at the memory of him putting his small penis away while trying to stand up. There, I was a survivor, not a victim. The rest of the week carried on as normal and some of those people who had been giving the looks and making the comments had gone very quiet and kept their distance from me.
On Saturday morning, I arrived at Martin’s and Jo’s as usual and they both pulled me into their flat, hugging me at the time, asking over and over again if I was ok. Once they had calmed down, we sat together having a cup of tea and we chatted as I wanted things to be normal, so I told Jo to go back to work planning the show and I looked at Martin, putting a hand on his leg and said, “And we will do what we usually do.” As I kissed him. Jo and Martin shared a look, but he stood up when I did and we went to the bedroom. I kept kissing him trying to get him going, but he was more gentle than usual. When I stopped and started to sulk, he admitted he didn’t want to push me after what had happened to me, so I kissed him and said, “Martin, I want to thank you for being so kind to me and being very gentle with me as you put me back into my underwear.” I kissed him. “That was very sweet.” He said he knew he had to cover me up, but the official story was I had done it myself and it was only my tights pulled down as he wanted to protect me. We ended up laying down on the bed kissing but we didn’t have sex. I did give him a hand job as we kissed and for the first time, I let him lower my thong and he gave me a hand job as well. Afterwards he admitted he had never done that before, so I told him he had done a wonderful job and I felt very satisfied. A few weeks later when I asked about this visit, he told me that any man who doesn’t behave the way he did after I had a traumatic experience is someone I should instantly dump.
Rehearsal with the girls in the afternoon went on as usual, we had all talked it out on the sleepover, but today I found out that Sarah had tucked me as she knew I would be upset with a bulge showing. I was really surprised and asked how she knew what to do, and she pointed out she has been in the toilets with a few times now so has seen me do it. Which then became me showing Kim and Jodie as well in case something like this happened in the future, even though it was very unlikely. They were the first people I told about what happened in the doctors and my decision to carry on being me after the show. They were so excited and after calming down a bit they all agreed to not tell anyone until I did as I wasn’t quite ready yet. On Sunday I managed to meet up with Steve and he gave me what Martin was held back from me and I needed to feel someone inside me, feel their body move with mine and to feel them have the orgasm I made them give me. I felt truly satisfied as I left him and started to head to Jodie’s for our Pink Lady’s jacket fitting. I loved it and her mum said I looked better being one cup size up and had made the jacket for me that way just in case. After that, I went back with Sarah to hers, and her dad took my extensions out and fitted new ones. The next week we had dress rehearsals each session after school and wearing the pencil skirt, the big petticoats and fully made up with my hair pinned up felt amazing. The Saturday before show week we had a full-dress rehearsal in the afternoon and I arrived there right after Martin had finally relented and I felt very full, standing on stage in costume feeling that a part of him was still in me. And then I had a real surprise as he was doing the part of Vince Fontaine, the TV presenter that I had to flirt with and I’m standing there, on stage, with us flirting with each other and I could still feel his seed slowly leaking from me. We had a break for some food before doing another run through. I went for a walk by myself around the empty school thinking how strange it was with no one here. The teacher’s lounge was unlocked and I couldn’t resist going in to have a look and see what was in there. It looked very run down, chairs with the stuffing coming out of them, a few tables and a lot of dirty cups, a dirty kettle and a small fridge. The door opened behind and there was Martin, looking surprised so see me there. “You know you’re not meant to be in here?” He said, but he was smiling, so didn’t really mean it. As I walked around the room looking at bits and pieces, he said, “You know you look great in that skirt and all those petticoats.” I did my Princess Diana look again, and smiled coyly at him, swishing my skirt around. “It does feel nice.” I told him. We were slowly walking towards each other, and I finally asked him what I really wanted to know more than anything right now, “So, is anyone likely to come in here today?” He looked at me and shook his head slowly. “Does the door lock?” I asked. He looked at me and slowly walked back to door.
“Do you know, I think it does.” He said, as he slipped the lock in place. We walked towards each other, slowly at first and then getting faster until I threw myself at him and we started kissing, thankful I had picked up my handbag with my lipstick in it. I pushed him backwards into a chair and lifted my skirts up so I could straddle him as we kissed. I could feel him getting hard so I reached down and undid his trousers, taking Martin’s cock into my hand as he was running his hands up my stockings, over my bum and pulled my thong to the side. I grabbed my bag and took a small tube of lube out, quickly spread it on him and sat down on his cock, feeling it go as deep as I could get it in one go, riding him slowly, rolling around on his hips, feeling him swell and move in me as we kissed. We seemed to make love for hours, but it must have just been a few minutes till I felt him start to swell in me and get harder, pointing into me, so I pushed down onto him to get him as far in me as possible as he started to twitch in me over and over again. Finally, he seemed to stop so we sat there holding each other and just enjoying the moment. “Come on,” he said, “you need to get back.” I kissed him one more time, but even as I started to climb off him, I slid back down his length, just enjoying the last moments of him in me. I lifted myself of him and rearranged my thong, smoothing out my petticoats and skirt, and walked over to the mirror with my lipstick to repair it. There were some tissues on the table next to Martin and he used them to clean himself up and wipe the lipstick off himself when someone tried to open the door. A key went in the lock and it opened and there was Miss Reeves, looking at us and smiling. She smiled at us and said, “Somehow I expected to find you both in here. Martin, you need to look after the rehearsal while I take a quick break.” And she walked across to the staff toilet in the corner of the room while Martin gave me a kiss on the cheek and headed out.
I waited for Jo to come out and we sat down and chatted for a bit, she was telling me how proud of me she is, and also thanked me for keeping Martin happy while she has been so busy. I still sometimes felt really bad about what we were both doing and asked her about it, but she just shushed me and said if I was happy then she was happy. We both walked back to the drama studio and did another run through in the afternoon. Miss Reeves gave us all notes and said that the rehearsals during the week will now be spilt into complete scenes focussing on the bits that she said needed work. The day of the first show we would all be excused classes and do a final full rehearsal before the whole school came in to watch us, then in the evening it was another show for parents. On the Saturday we had one final evening show which is the one people are buying tickets for and the one we had to knock it out the park. We all felt ready, but more than that, I felt happy.
Previously......
We lay there embracing and kissing each other as he stayed hard inside me. “I needed that as much as you I think.” He whispered in my ear. I kissed him deeply in agreement as I wrapped my arms and legs around him to hold him tight, with my panties hanging off one ankle.
And then I heard a cough.
We both opened our eyes and looked to my open doorway and my sister was standing there.
“Errrr. Hi sis” I said.
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Day off
Being caught by your sister with your boyfriend inside you is embarrassing, but not as embarrassing as it happening while you’re wearing all of her clothes and you sigh as he pulls out of you with her watching. Steve tried to cover up, but she saw his still hard penis. She smiled and said, “Well, who’s a lucky girl then?” I reached down and put my other still booted foot through the leg of my panties and pulled them up, tucking myself as best I could. Bev said we need to talk and headed to her room. Steve wanted to leave but I told him that would be worse, so we walked to her door, knocked and went in.
She looked at me and said at least I knocked this time and told us to sit down. The first thing she said was I could keep everything I was wearing and that in future I should ask if I wanted to borrow any of her clothes, but would need to get my own underwear. She then asked a few questions about the two of us, which were horrible to answer, but honesty was a better option now as it would be a lot less fun if she decided to fuck me!
After explaining about me and Steve, he had to leave and I needed to get changed. Bev helped me take off the makeup leaving no trace, then we talked a bit more about my dressing. I explained that I’d been borrowing her stuff for a while now, and we worked out a plan that I could borrow some things, but not others. “You’re my sister and you have to accept this. I will help you as much as I can, but at some point it’ll either need to stop or you’ll have to tell everyone.”
Neither of those options appealed to me right now. She made some space in her wardrobe where she would keep the stuff I could wear, and part of a drawer for my underwear, that way I could just put stuff in the wash and she would put it back in there and I wouldn’t need to worry. She even made some space for the wig, but as hidden as possible to make it easier for me, until I could do something better with my own hair.
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The next day our folks were out all day, so Bev took me shopping in mum’s car. I had to wear yesterdays underwear, which was a bit uncomfortable as I could still feel Steve’s cum in them where it leaked out me. I wore a pair of tights, jean skirt, the same jumper as Friday and this time one of her jackets that she let me borrow. Walking out the house on a Saturday morning dressed was nerve wracking, but I was quickly in the car and off we went. The drive to the next town took about an hour, and we went to a few shops, I picked up several pairs of pants and bras, a long wrap around satin skirt, a pair of jeans and a couple of tops. Being there with her was the first time I went into a girls toilet with another girl, and of course we just chatted away like any other girls in there. It was funny in a way, previously I’d always been really nervous when I went in them, but this time it actually felt natural.
Yesterday with Steve was different because he was being my boyfriend, and when we met Nicola that was more about explaining some of what was going on. This time I was just a girl with another girl hanging out for the day. I also really liked being checked out by guys; Bev told me to get used to it and just enjoy it when it happens but pointed out that sometimes you will hate it and feel threatened by them She pointed at my ankle boots and said, “How easy do you think it will be to run in those heels?” I took her point.
We went home about 1pm and sat in the kitchen together having lunch, and then sorted out my clothes for her wardrobe. I’d also picked up a pair of boots that I’d worn out the shop right after buying them, knee high and lace up, a three-inch heel that tapered to narrow point. They were much easier to walk in than the ankle boots, and they still made me feel sexy. I was hoping I wouldn’t be asked what happened to the £150 birthday money I’d been saving, but the risk was worth it.
Bev helped me for the rest of the day work out my make up looks, and we played around with my hair to see if anything could be done; if nothing else it would stop me being scared of it being pulled off by accident. With quite a bit of mousse and use of the hairdryer and brush we could give me a similar style to Shaznay Lewis from the girl group All Saints. After washing it all out, I tried to do it myself and it worked, sorta, but I figured even if I did it myself I could pull it off.
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Sunday was a homework day, but Monday at school I was a little nervous. I’d spoken to Steve a bit, but Michael and Nicola were a different matter. Turned out I had nothing to worry about. Michael didn’t mention it at all, and Nicola just said to me when we were alone how much she enjoyed the day and hoped we could hang out again. Wednesday evening she invited me round after school to do some homework with her, and as soon as we got in she said she’d put some old clothes aside for me if I wanted them. I thanked her and said I would arrange to pick them up with Bev as there was no way I could get the three bags of clothes in without questions being asked. I did ask if she had any old school uniform stuff I could have as I didn’t have enough. She looked at me confused, asking what I meant. I stood up and showed he the trousers I was wearing came from Top Shop, and that my shirt was actually a blouse.
Her jaw dropped when she realised and found a spare blouse for me to wear. The next day at school, I wore her old blouse, and as I was feeling really brave, one of my new thongs, the trousers with a side split and under the blouse one of Bev’s fitted white tee shirts, with her black trainers. I was even wearing a pair of her socks, with a pair of black tights on underneath. The only part of my uniform I wore that day was my tie and the jumper, but that was unisex anyway. I bumped into Steve near school and we went in together as normal. Just before we went in I told him I wasn’t wearing any of my clothes, and when he looked at my shoes and trousers he realised I was telling the truth. He checked no one was near us and asked, “Stockings?” I smiled and said he’d have to find out later.
Nicola spotted what I was wearing right away, but no one else did. At lunch-time Steve and me went to the big library near the school and headed for our usual hiding spot in the fire escape. It was really cool there as it was quiet, people rarely came in and the windows gave a great view of the city. This time we didn’t get to look out them, and it had barely registered with me that Steve had suggested we go here this time. Once through the doors we headed up the stairs and I felt his hand on my bum. So that’s why he wanted to come here I thought. I turned to face him in the first landing and he kissed me straight away, telling me how much he had to keep reminding himself not to call me Amy, how hard he had been all morning. I reached down and felt it, and he was rock solid; he moaned as I rubbed it and undid the zip reaching in and pulling him out.
We went up another flight of stairs, his penis pointing the way and I thought if anyone looks through the window they’ll have a treat, but less of one than I’m going to get. Once we were at the top we kissed again and I dropped to my knees, taking him in my mouth, licking and sucking at him, enjoying the harness, softness and warmth in my mouth. It didn’t take him long to come, and once again I swallowed it all. When I stood up I was about to get my bag to rinse my mouth out to kiss him, but he pulled me close and kissed me deeply. I don’t know if he could taste himself, but I felt like I loved him in that moment. We both sat down to look out the window and he put his arm around me, puling me close to him. I felt so protected at that moment as I rested my head on his shoulder. He rested a hand on leg and stroked my inner thigh and every now and then we would look at each other and kiss, never saying a word.
After what seemed like forever, I looked at him and said, “You never asked.” He just smiled and said ‘Why do you think I’ve been stroking your leg?” I nudged him in the ribs and pulled me closer. We ended up falling backwards and laughing, which became kissing and caressing. I felt him undoing the zip on my trousers and I never stopped him. We were in public, anyone could walk in on us. He pulled my trousers down as I undid his and pushed them down along with his boxers. He sprung free, hard and erect again. My trousers came down and I kicked my shoes off. I needed him in me badly right now, I wanted to feel him in me. He pulled my tights down, but when he got them to my calf’s, I lifted my legs and with my knees open I put them over his head and he climbed between my legs, laying on top of me and kissing, I had no idea if he had any lube with him, but I was so desperate for him to be in me I would have tried it without.
He grabbed his bag and pulled it over, taking something out while his erection was pressing against me. I was already pulling the thong to the side for him, but he moved away and knelt up. It was uncomfortable with the tights still on, but seeing his hardness there was a beautiful sight to see. He finally got whatever it was he wanted from his bag, and it was a small tube of lube. I took it from him, and started to squeeze some out, stroking him while coating him with it. As he lay back down on top of me, I wiped the excess lube on my legs and I felt him push against my hole. I opened up to accept him and he slowly pushed into me, kissing me as he did so.
Laying there on the fire escape staircase, with a window overlooking the city, he fucked me and I loved every second of him in me. Being stretched by him as he moved about in me, kissing me, tasting his tongue in my mouth as his cock was filling me. I felt so satisfied to be under him right now, so privileged to feel him in me, so close to him. He came inside me and kissed me as he did so. Feeling him expand and twitch inside me as he bred me. We lay there locked together as we came down from our high and heard a door open on a lower floor. I kept my legs wrapped around him and didn’t want him to move, this moment was too perfect, and I didn’t care if someone found us.
We listened to footsteps going up, then another door being opened and closed. I kissed him and released my grip on him as he slowly pulled out. Before I did anything, I grabbed my bag, took out some tissue and wiped the lube off his slowly deflating erection, then lifted my legs to let him move away. I rearranged my thong and stood up. As I bent down to pull the tights back up, I felt a bit of his cum seep out of me and into my thong, hoping that the tights would help hide it. Once my tights were up, I pulled my trousers up, zipped them and gave him a kiss. After waiting a bit to calm down, we headed back to school.
It was a shame that once there we couldn’t be honest about what had happened, and we had to change how we behaved towards each other. A couple of times I had to stop myself from kissing him, and he acted the same. In our final break of the day, I made sure we kept a bit of distance, and Nicola spoke to me about it. I confessed that we’d had sex lunchtime, and I told her where it happened. She was really interested in knowing the location and how to get there, so I guessed that Michael was going to get lucky there too at some point.
The next day at school I dressed pretty much the same, except I spent more time on my hair in the morning, trying to keep my usual style, but to give it a bit more body. I even put some mascara on, feeling very brave. I made sure that Steve knew about it, and this time I had prepared a bit better and managed to pick up some lube of my own. At lunchtime we headed to the library and I made sure he knew where we were going. We opened the door and inside was Nicola and Michael, making out. When I made eye contact with her, we both squealed in delight, knowing what each of us was here for.
Steve and Michael were embarrassed, but I thought screw it, the guys know, so lets just do it. I hugged Nicola and said, “It’s safer to go to the top.” I took Steve’s hand and started walking, hearing Nicola and Michael start to follow us. At the top I turned and kissed Steve, and with one hand I unzipped the trousers, letting them fall. I wanted them both to see what I was wearing today, and Steve got the message and started stroking my nylon covered bum and legs. I looked over and Nicola and Michael were kissing and his hand was up her skirt. I wondered how long it would take for him to start fingering her, and Steve started playing with my hole.
I wasn’t sure about having full sex in front of them, so I reached down and took Steve’s erection out his trousers, knelt down and started sucking him. Michael looked at us and we looked each other in the eye. I gave him a wink as I took more of Steve into my mouth making him moan. I watched Michael put his hands in Nicola’s panties and start to finger her. The experience of both of us having a sexual experience next to each other was quite a turn on for me and my tuck was struggling to hold itself. I watched Michael lay Nicola on the floor as he took her tights off with her panties in them. He then knelt between her legs, took his own penis out and Nicola handed him a condom. I felt a bit bad then as we’ve never used one, but then I can’t get pregnant.
Michael rolled it down his dick as quick as he could, then lay on top of her. At that point I knew I wanted Steve in me as well. I quickly pulled my tights down and stepped out of them, pulling Steve down on top of me. With all the salvia from sucking him, and too be honest I was too hot for him right now, I opened my legs, pulled my thong to the side and he was in me. I looked over at Nicola and she was watching us, smiling at me. We then both focused on our own guys and let them fuck away, occasionally looking at each other as we rocked back and forth from the action going on between our legs.
Steve didn’t need a lube cleaning this time, so he put himself away as I watched Michael take off the condom. He had no idea what to do with it, so I grabbed a tissue and held it out him, but he put the used condom in my hand. Me and Nicola just laughed as I wrapped it up and handed it back to him. As the guys tried to talk as if nothing had happened, Nicola and me put our tights back on.
“That was amazing!” I told her. She agreed, saying the first time they both had sex was at party on a bed with another couple next to them, and it reminded her of that. She told me that my mascara had run and lent me hers with a mirror to touch it up. The boys were chatting and occasionally looking back at us. We helped each other with our hair, and I realised that mine had gone a bit flat, but I could live with it. The rest of the day at school I had classes with Nicola so we sat together and I had to keep reminding myself not to be so girly in public, but at least for the first time, I now felt that I had a BFF I could be a girl with. I also realised that I had now seen another erection, and Bev was right, I am a lucky girl, but not by much. It also occurred to me that I had held another man’s cum, even if it was in his used condom.