---------------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.