I left off the story with me exploring my femininity with my girlfriend, Anna. We had gone to the mall, and Anna had bought a little something special for me…

Day 7

As I woke up, I noticed that Anna was lying awake in my arms. I kissed her and told her good morning, and she did the same. The combination of her closeness and the feeling of my new nightgown was exhilarating. This was definitely the life.

Anna was unfortunately leaving for a week. She was going back to her hometown to visit her family. I really wish she didn’t have to go, but I know how important family is to her.

Before we got up, Anna said that she wanted to give me a little treat for all of the effort I’ve put into becoming a woman. I got very excited as she pulled down my panties. She released my dick from its prison and it sprung to attention. She had me lay down on my back and she got to work.

She started by giving me a handjob. As she rubbed her hands along my member, her long nails would click and sometimes touch my skin. Her pretty nails could have made me cum on their own, but she kept the pace slow so that I didn’t explode too soon. She then took her hands off of me and lowered herself onto my penis. She moved little by little before I was fully inside her. I could feel her wetness with my penis, and it acted as a lubricant for our intimate love-making session. I was getting ready to cum, but she lifted herself off of my member before that could happen. She waited a little bit before she spoke.

“Before I let you cum, you’ve got to beg me for it like the girl you are.”

I was a little confused at first, but I understood. “I wanna cum sooooo bad.”

“I don’t know if that’s girly enough. I want to hear you talk about being a sissy and having your clitty sucked.”

“Please let me cum, my clitty is desperate to be sucked. I’m such a little sissy and need to have some release.”

“That’s better. Now keep saying it while I suck you.”

As she sucked on my dick, I cried out that I was such a sissy for having my clitty played with. I talked about how much of a girl I was and I was such a slut for wanting sex so much. Soon enough, my penis spasmed, and I began to cum in Anna’s mouth. Every little squirt was a wave of pleasure. She used her tongue to make sure that she could make me cum as much as possible. My dick became very small and was the same size as after the last blowjob. Anna, with cum still in her mouth, move up to kiss me. She released all my semen into my mouth and had me swallow. I still wasn’t a big fan of the taste, but in that moment, I did feel like a sissy slut.

Anna got up and grabbed something out of the shopping bag she had from our trip to the mall. Before I even knew what was happening, she took my dick and attached something to it. When I looked down, I saw a pink piece of plastic in place of my penis.

“This is called a chastity cage. It prevents you from getting hard or even touching yourself. I’ve got to make sure you stay a good girl while I’m gone. I’ll have the key with me, so there’s no way you’ll be able to get it off.”

I was a little stunned. Where the hell did this idea come from? I had to admit, it was more comfortable than the tucking, but still. I guess I was under her control at this point, and I just had to live with it.

We spent some of the morning hanging out before Anna had to get to the airport. I decided to drive her there in her car, since I didn’t want her to have to pay for a taxi or parking. Once we got there, we kissed each other goodbye. Before she went in, she mentioned something to me.

“I know you’re kind of disappointed about the little cage you have now, especially since you can’t masterbate like you normally do. But I couldn’t let you suffer, so if you get desperate for some release, I left a few surprises in my bag to help you do that. Bye, baby, I’ll miss you.” With that, she walked through the doors of the airport.

“More surprises,” I thought. “That’s just great. And how can I get release without having Anna and with my penis locked up?” I wondered what I had gotten myself into the whole time I was driving home.

Day 12

The first couple of days without Anna weren’t too bad. My nails had chipped a little, so I repainted them, with a French manicure on my fingers and red on my toes. I also kept practicing doing my makeup, even though I was already good at it. I tried on the clothes we bought last week again, making sure that I still liked them.

After a while, though, things got harder. With all of the feminine activities I was doing, I was getting horny. My penis would constantly try to get hard, so it kept straining against its cage with no luck, making me a little uncomfortable. At this point, I was feeling so hot and bothered that I couldn’t take it any longer.

I went to Anna’s bag to find what her surprises were. There was a bunch of things in the bag, but one of them had a note attached to it. It read:

Lauren,

I knew you would cave at some point, you little sissy slut. Since your penis is useless right now, you need a new way to get pleasure. This bag has many things for you to use, but I want you to start out with the toy this note is taped to. Use it on your virgin pussy, preferably while you’re on your back. There’s some lube in the bag, and I recommend using plenty of it. Have fun!

I looked at the toy and my eyes widened. It was a dildo! “I can’t use this, this is way too far!” I said aloud. But I started to wonder if it wasn’t. I was already completely like a girl in every way. During the past week, the way I looked, moved, and even had sex was in no way like a guy. Does that mean I should try to masterbate like a girl, too? I’ve been curious about what it’s like, and obviously Anna thought that I should try it out.

I was so horny that any worries were out the window. I took the dildo and examined it more. It was about 6 inches long and 1 inch wide. Could this thing really fit inside of me? I guess there is only one way to find out.

I stripped down to just my bra, grabbed the dildo and lube, and layed on my bed. I propped my legs up, with my asshole in full view, and got to work. I squirted some lube into my hand and rubbed it all over the dildo. I also used a little bit around the inside of my opening. I took the dildo and slid it in between my buttcheeks. As it entered my hole, I gasped. It was such a weird and wonderful sensation.

It didn’t take long for the dildo to be completely inside me. I slowly started moving it in and out, trying to mimic how I’ve fucked Anna before. I started to moan, it was almost involuntary. I soon found a spot that made me feel amazing and pumped the dildo so that it would consistently hit that spot. My moans were in line with the movements of the dildo. I kept at this pace for about 30 minutes before my body began to feel tingly. I rode this tingling sensation as it increased, and soon, my entire body was floating on a cloud. After a few more fucks of my opening, I felt a huge wave of pleasure rush over me, and I tensed up as I exploded with enjoyment. It felt almost like an orgasm, but different, and a lot more satisfying.

Laying on my bed, I still felt unbelievable. That was the best orgasm I had ever had, there was no doubt in my mind. Looking at my clitty, I noticed only a few drops of cum came out of me. All that pleasure, and I only cummed a little?

I realized that I still felt horny and decided to go at it again. Over the next hour, that dildo stayed inside me as I wanted to keep fucking myself. I orgasmed three more times over that time period. After the final one, I just collapsed on the bed. The dildo slid out of me on its own, making a distinct popping sound. I definitely had to do this again.

As I was getting up, I decided to see what else was in Anna’s bag. There were multiple dildos of various shapes and sizes, and one even vibrated. She also had an array of butt plugs in different sizes. I decided to see what they felt like and picked up the smallest one. I took a little more lube and squeezed the plug into my opening. “Ooh, that feels nice,” I thought.

I put my clothes back on and just chilled out for the rest of the day. I couldn’t help but tighten my sphincter every now and then, reminding me that the plug was still there. I loved having something inside of me. Anna was definitely right about me being a sissy.

Day 14

I drove to the airport to pick Anna up after her trip. As soon as she walked out, I got out of the car and greeted her. We made out for a little bit before I helped put her suitcase into the back of the car. People were probably a little weirded out seeing a “lesbian” couple kissing each other for so long, but I honestly didn’t care. We got into the car and drove off.

“Did you use any of the surprises I left for you?” Anna asked.

“I did. Actually, I’m using one of the butt plugs right now.”

“Mmm, I can’t wait to get back and see you with it. What about the dildo?”

“All I’ll say is my pussy isn’t a virgin anymore. I fucked myself silly the other day.”

“Oh my god, Lauren, that’s so damn hot. I think I need to fuck you later. I haven’t had any release all week, it was a little hard to do anything with my parents in the next room.”

Once we got to the house, we practically jumped out the car with excitement. After I closed the front door, we began to make out again. We took off each other’s clothes, leaving us in our sexy lingerie as we moved to the bedroom. “I wanna take a look at your pussy,” Anna exclaimed. “I need to know what I’m in for.”

I complied and took off my panties. I layed face down on the bed with my ass in the air. Anna smiled when she saw the butt plug, taking it in her hands and yanking it out. A little squeak came out of me when she did that.

“Before we get to it, I need you to do something. I can’t work with an unclean pussy, it’s unsanitary.” She grabbed something new out of the bag and gave it to me. “I want you to give yourself an enema. Make sure that the liquid that comes out of you is clear before you return to me.” I did as she said and came out with a nice, clean opening. “Now we’re ready.”

Anna had me get on all fours while she prepared herself. She played with my buttcheeks a little before spreading them out. She took some lube, spread it on her fingers, and got to work. She started by teasing the rim of my pussy before inserting one finger. She rhythmically moved her finger in and out of me before adding a second finger. I moaned with pleasure as she finger-fucked me as hard as she could. Once she added a third finger, I was in heaven. That small amount of effort made me orgasm in no time.

Obviously, we were still horny, so we weren’t done yet. Anna turned me on my back and moved her head towards my pussy. She was about to eat me out! She stuck her tongue out and got to work. It started out with just a light licking, but soon her tongue became its own fucking machine. Her tongue explored my pussy, and it consistently hit the sweet spot. I moaned even more than last time as she continued to devour me. This was amazing! I let out one last squeal before I orgasmed again.

“You up for more?”

“I’m still so fucking horny, of course I am!”

Anna got one of the dildos and used an attachment to strap it onto her. Looking at the dildo, it was about 8 inches long and 1 1/2 inches wide. God, that’s so big! “Now, this dildo is a little special, and you’re going to see why in a little bit.”

Staying on my back, I lifted my legs up onto Anna’s shoulders so she could have full access. She took a generous amount of lube and put it on the dildo and my pussy. When she entered me, I let out a little moan. It felt so good having my pussy stretched! She started with a slow pace and was only a couple inches deep. As time went on, she increased the speed a little, progressively getting the dildo further inside of me. Before I knew it, the whole thing was inside me.

I could feel an orgasm start to build up, but knew that it would still be a little while before it happened. I wanted this to be the best orgasm possible, so I said, “Fuck me harder! I want to feel everything!” Anna complied and quickened up the pace. I moaned with pleasure, and my moans began to sound more girly the more she fucked me.

We kept at this for about 10 minutes before I felt like I was going to orgasm again. “Oh god, I think I’m about to cum!” Right before the release, I felt the dildo jerk a little and something warm and sticky shot into my pussy. Whatever it was, it sent me over the edge. This time, as I orgasmed, a huge squirt of cum came out of me and hit Anna in the face. I was a little surprised by that, since I’ve only ever had a few little drops come out of me while locked up. We both collapsed on the bed, with the dildo still inside of me.

“I see you liked the little surprise this dildo had in store,” Anna said. “If you haven’t figured it out, it simulates the male orgasm and shoots out its own version of cum. So, you just got fucked in the most girly way possible.”

I was still catching my breath from that amazing experience. I honestly didn’t care that I practically had a penis cum inside of me. This newfound form of orgasm was life-changing, and I don’t think I ever wanted to go back to having a male orgasm.

Anna and I snuggled together in bed. I wondered what the rest of the month would be like as we fell asleep in each other’s embrace.

To be continued…