Becoming His “Girlfriend”


I always knew that I liked men from the very beginning. I kind of always had in the back of my mind that one day I might do more than just have normal sex. I grew up around women. I heard a lot about women’s issues. And I think the world of women. I probably would’ve done something like this sooner if I didn’t respect women so much. I thought it was an insult to compare myself to one, or try to be one. But I’ve always known that there’s a girl inside me. One day, it was always going to win.

Not only did I always know I like guys, I always knew I was going to be a total bottom. It’s what comes naturally to me. I’ve never had any desire to top whatsoever. So naturally, I’ve always been thought of as kind of girly. My main audience of guys would be bi/’straight’ guys who loved that I would never ask them to bottom. And I had heard it all from some of them. I’ve been called a faggot, a sissy, a girl (in a derogatory manner) by guys in private. I don’t have a big problem with that. I kind of wear the titles proudly.

The first time I went full girl was my junior year of college. I had met a football player named Kevin at a few parties I was dragged to by my friends. He was slowly exploring his sexuality, and since I was now standing out a bit more for being gay, it made me a little bit of an easy target for someone like him. He was a very nice guy. He was a back up offensive lineman, and he was BIG. He was 6’5 284 pounds. I’m 5’9 130 pounds at the time. He had sought me out he would later tell me and we talked once or twice. He was cute, and when he put my hand on his cock, I didn’t mind. He didn’t seem to mind kissing me when I tried. After that he would let me give him a bj. I would always offer to go all the way, but Kevin said, “I only fuck girls.”

Now, I would be honored to be compared to a girl. I would always say,

“You can think of me that way. Pretend there’s nothing in the front. Just think of me as your girl.”

But he wanted to go slow. That’s no problem. I respect everyones process.

Until one night in December. By now, I had been blowing Kevin for over 2 months. He was getting more and more comfortable. Late at night, he didn’t mind being seen with me. Then one night in late December, we were talking dirty to each other. Kevin and I really got each other revved up to the point where he picked me up and bent me over the desk in his room. He pulled down my pants and sadly got a look at the front, which turned him off. He just came up and said,

“I just can’t do it. I’m sorry, I can’t do it.” And he walked out of the room.

A week went by before we saw each other. Kevin just seemed to disappear from me. Until one day at lunch, we saw each other and took our food back to my place.

“I’m sorry.” Kevin told me. “I’m exploring more, but I’m just not sure how much I like guys.”

Which was a very understandable position.

“I understand.” I told him.

I was about to go on when he got the courage to talk,

“I think at this point I’m still only comfortable fucking girls. But after all of this and what you’ve told me, you’re as much a girl as some that I’ve known.”

I was delighted to hear all of this and he finished with a hurried sort of worried look on his face,

“So if you can find a way to be more girly, I’d be more comfortable going all the way.”

That was a really defining thing to say. It’s something I’ve long thought about since I learned about gender as a child. I’d always been comfortable as a man. I always had feminine desires, that’s true, but I knew I never had what it takes to switch genders, at least, not yet. But ever since I knew I both liked guys, and my sexual need was to only bottom, I expected a day like this would always come. I had thought about it. Would I say ‘yes’ or ‘no’? Sometimes I would think ‘yes’. Other times it was a quick ‘nope’. But here it was being said to me in the real world. My instinct took over.

“I can be girly if that’s what you need.” That’s what I ended up saying. It would go on to define much about me, but that’s many other stories.

“How girly?” I needed anime porno to know.

“Make me believe that you’re a girl, and if you do it right, I’ll let you know.” He said with a grin on his face before he gave me a tap on the butt.

So now it was on. I’m one of those people that has to do my best when I do something. I’m not one to pace myself. I know how to give 100% or 0. I don’t really have much in between. So if Kevin wanted a girl, then he’d get a GIRL.

I’m very lucky I have my friend Veronica. She was the first person I came out to publicly I should say. She was the person I told that I only want to bottom. And she told me it was ok. She has been my rock from the very beginning. So when I told her that I needed to be girly, it’s safe to say that she jumped at the opportunity.

Off we went, buying makeup, panties, a wig and some high heels. Picking out the outfit was tough. Veronica wanted me to get a dress. I tried a couple but they really didn’t work for me. They didn’t say what I wanted them to say. We ended up picking out a pink and white look. Pink heels, white stockings, a pink pleated mini skirt, a white blouse all topped off by a pink beret (I’ve been told they’re girly all my life, so if I’m going to be a girl, there’s no way I’m not wearing one). I had never felt more cute in my entire life. Shopping with Veronica was amazing. We also picked up a chastity cage. If Kevin wanted a girl, I was going to go as far as possible.

So we hatched a plan, when he was out that Saturday night, Veronica would tell him that there’s something special waiting in his room. And there I would be, all dolled up.

It was the most fun I’ve ever had. Veronica helped me with my makeup. Some foundation, some blush, eyeliner, eye shadow and then finally some pink lipstick. After she helped me with my makeup, she went to go find Kevin. I put my wig on. Put on my new heels, stockings, underwear, skirt and blouse. Then I looked at myself in the mirror. It was one of the most amazing feelings in the world. I looked how I wanted to look. I felt like myself for the first time. And the clothes were really sexy. I loved the freedom a skirt gave me. I got a text from Veronica, ‘He’s on the way!’

I ran over to his bed quickly and got in what I felt was a sexy position. But I didn’t like that after a few seconds. I got up and thought about sitting down. I wanted him to know that I was ready. I was so busy thinking that I didn’t even hear his key in the door! From my left, all I could hear was, ‘WOW’. I looked over, and there was Kevin standing in the doorway.

I was surprised, so all I could say was, “I hope you like it.”

As I was saying that, Kevin lunged towards me. I had barely finished my sentence when Kevin started kissing me.

Now these kisses were different from any in the past. They were deep and passionate. His tongue dominated my mouth. We kept making out as he walked me over to his bed, where he fell on top of me. He started rubbing me all over my body. Those massive hands felt great. He reached under my skirt after a while and felt my new cage. “Now that’s more like it” was all he broke off our making out to say. We kept making out for a little while when I decided I needed his cock. While we were still kissing I flipped us over so I was on top of him. I started kissing down his chest while I unzipped his jeans.

There was his beautiful cock. 7 inches and thick, also cut. And it was rock hard for me. I attacked his cock with my mouth. It was the most aggressive bj I’ve ever given. Going up and down on his shaft with such passion, keeping my tongue around his head.

I could hear him moaning in pleasure, “oh my god that feels so good.” And “that’s the way a bitch sucks.”

I felt so good hearing that that I could’ve gone all night just sucking him.

But Kevin had other ideas.

I would’ve sucked him until he came, but after another few minutes, I heard him say, “stop stop stop!” So I backed off.

“Is everything ok?” was all I could say. He did sound a little frantic.

“Yeah, everything is fine.” anne porno He said, catching his breath a little.

So I went back up to his mouth and started kissing him some more. I could tell he was letting out more pleasure moans than I had heard in our time together. I was really starting to feel proud of myself for my looks when he wrapped his arms around me, and picked me up. We kept kissing as he held me in his big, meaty arms. Then he put me down.

“Time to go all the way” he said.

This is what I had been waiting for.

I did bring one other thing with me, some lube. I grabbed the bottle, and put some on his cock. He let out a moan or two as I was doing this. He kept thrusting with his cock like he was already inside me, which I found incredibly hot.

Once his cock was ready, I started to ask him, “how do you want to do…” when all of a sudden his passion took over.

He lunged for my lips again and we kissed deeply. We were in the middle of this kiss when he broke it off.

“Turn around” he whispered to me, and I complied.

As soon as I turned around, I could feel his hand on my back. I opened my eyes to see we were at his desk again. He bent me over and I could feel his hands around my panties. He pulled them down, and started lining up his cock with my hole. Our first attempt didn’t go too well. His head popped in, and in one big thrust, he pushed all the way in.

My hole wasn’t ready yet, “hold on there stud!” was all I could say.

He took his cock out of me while the pain subsided.

“Ok, now I’m ready” I said with my head against his desktop.

Again he lined up his beautiful cock. He pushed in and the head got in. This time, it was only pleasure. I let out a moan of approval, and he slowly pushed all the way inside me. I WAS IN HEAVEN! My dream was coming true. Here I was, with this very handsome guy, and I finally got to be the girl I always knew I was. He first started fucking me tenderly. Long, slow thrusts, in and out. I could only moan in pleasure at the overwhelmingly good feeling of his cock. This was something special. I was far from a virgin. But this was the most special sex I’d had up to that point. My body was on fire. Everything just felt right in ways that hadn’t existed before.

“You make a good bitch.” He said as he kept fucking me.

“I’m your bitch.” Was all I could manage to say back.

This seemed to get him going, as he started to pick up the pace a bit. He kept up his fast pace for a little bit but then slowed down, then totally stopped.

When words returned to me I looked behind me and asked, “are you ok?”

“Yeah, I just need a break.” He said as he slowly pulled his cock out of me.

This gave me a minute to adjust myself. My beret had fallen down over my eyes, so I adjusted back to its original position.

“This has been amazing” Kevin said as he sat on his bed.

“I’m glad” I told him.

“Come over here” Kevin said.

I walked over to his bed, leaned in and started kissing him. His hands went right for my blouse, and he started unbuttoning it. He took off my blouse and then pulled down my skirt.

“You’re so sexy, let me see” Kevin said while we were still kissing.

So I broke it off and walked to the middle of his room in my heels, stockings, panties, bra, wig and beret. I did a slow turn for him.

“You’re so beautiful this way.” Kevin said, as he got up off the bed. Our lips locked again.

I could feel Kevin pushing me somewhere as we were kissing, but I had my eyes closed and I couldn’t tell. All of a sudden, I felt a bar in my hip. As it turns out, he was pushing me towards his bed. He kept pushing, until we both fell on his bed together, with Kevin on top of me. We kept kissing until I felt one of Kevin’s hands around my leg. He took it and put it on his shoulder. Then he took the other leg and put it on his other shoulder. I knew what was going on, and I was very happy about it. Kevin lined up his cock again, and pushed in to me again.

This time was different though. Where Kevin arap porno had been mostly silent at his desk, seeing my face brought out the alpha male in him. He made one big thrust and I moaned in pleasure at the feeling.

“You like that?” Kevin said as he looked at me.

“Oh yeah, I love it!” was all I could manage to say.

That seemed to be the answer he wanted, as he pulled back, almost all the way out of me, and then slammed back in. I guess he could see the pleasure on my face, because he started to get a lot more verbal.

“That’s right, take it like my girl!” Kevin said.

“Yes sir, I’m your girl.” I got out in between moans.

“Are you my little sissy bitch?” Kevin asked as he continued to fuck me.

“I’m your little sissy bitch.” I managed to say.

“You love cock don’t you?” asked Kevin as he continued to fuck me at the same pace.

“I love it. I love it. I love it. I love it.” Was all I could manage to say.

This pushed Kevin in to overdrive. His thrusts were full of passion. Harder and harder and harder. This continued for a minute or so. I could see the look on Kevin’s face change. He was tensing up.

“Oh baby I’m close.” He said.

A few more big thrusts was all it took.

“Oh baby I’m cumming!” Kevin said.

He took one last big thrust, then pushed his cock as deep as It could go. I felt the wonderful feeling of him cumming in me. The warm feeling of cum in my stomach, combined with his cock being as deep as it could touched off something inside me. My body was on fire from head to toe.

“Oh Kevin, Kevin, KEVIN!” was all I could say as my first sissygasm overtook my body. I screamed out in pleasure as the most amazing feeling overtook my body. It’s the most intense orgasm I’ve had so far. My body would have been shaking if it wasn’t for Kevin’s huge body on top of me. I was lying there in heaven as Kevin pulled out of me.

Then, everything changed. Before I knew what was going on, Kevin had his underwear on.

“You gotta go.” He said.

“I will.” I said still laying there.

“No, I mean you gotta go now.” Kevin said in a dead serious voice.

I was still laying there trying to figure out what was going on.

“Seriously, get your shit and get out of my room.” Kevin said. I could tell the seriousness in his voice.

“Ok, just give me a second.” I said. I had come in male clothing which I still had a bag. I started moving towards the bag, but Kevin got there first. He picked it up, and threw it in to the hallway of his dorm.

“Get outta here you little bitch faggot!” he said seeming very angry.

So I did the only thing I could. I put my panties back on and my skirt. Buttoned up my blouse. Put on my heels and walked in to the hallway.

The walk back to my dorm was one of the craziest experiences of my life. Here I was, in full women’s clothing and makeup. Some people knew I was gay. But to most people I could pass very well as a guy. My walk back stripped away all of that. At first I was nervous. I didn’t have anywhere to change, so I’d have to make it back to my room looking like this. Two guys passed me in the hallway. They went right past and just kept walking.

“Maybe this will be ok” I thought to myself.

Down the stairs I went to the first floor of the dorm. I passed a few people. No comments. No bad things said. I passed them and they passed me.

It was night and my campus was pretty dark at the time. My dorm was only about a 5 minute walk away. Those were the most empowering 5 minutes of my life. My nerves had given way to confidence. I didn’t pass too many people on campus, but I kept my head high when I did. This was the me I had always wanted to be deep down. And she was finally coming out. With Kevin’s still warm cum in my ass, I strode across campus.

“Yes, I’m a sissy. Yes I just had sex. Yes I loved every second of it.” Was all I could think to myself.

I got back to my dorm, and went up the stairs to my floor. I put my key in the lock to my room and opened the door. Sitting on his side of the room, was my roommate Julien. He got up and looked at me, stunned.

“What’s wrong?” I asked him seeing a funny look on his face.

“You look interesting.” Julien said.

By that point, I had pumped myself up mentally so much, I had forgotten I was still dolled up!

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