My first time being with a real boy happened a few weeks ago and I wanted to tell you all about it!
I'm not really gay, but I am a huge sissy, and I guess bi? I'd had fantasies for a long time about dressing up and being with a boy, and I finally felt able to make that fantasy a reality.
I had a friend at university a few years ago called Steve. Steve and I used to party together a lot, and we'd get drunk and sometimes things would happen. Nothing major, just lots of kissing. Once or twice we had exciting little squeezes of eachother's cocks through our jeans, but nothing more than that. Steve knew all about my love of dressing up like a sissy but I'd never done it in front of him or anything.
I got in touch with Steve again a few weeks ago. It had been about a year since we finished university and he'd moved away. We were still good friends but didn't talk often. I confessed to him that I sometimes stroked my cock when thinking about when we'd kissed, and he said he did the same. I told him about my fantasy of dressing up like a girl for him, and I was pleased to hear he was excited about it. We decided to meet up. The plan was that he'd come to mine, I'd dress up and we'd "see what happens". I was very excited! I had no idea how far we'd go...!
The big day came and I was very excited. I'd ordered a special outfit just for the occasion, a very sissy strappy top, and a skirt with frilly knickers (all pink and white!) and I had some new make up too. When Steve arrived though, I was dressed up in my normal boy clothes.
We sat down and had a drink, and spoke about everything other than why he was here. We were pretty drunk by the time we ended up kissing, and I said "So...would you like me to dress up for you?" He nodded, and I went into my bedroom to get ready.
I was shaking and my heart was beating so fast. Of course my dick was throbbing as I stripped off and began to pull on my sissy clothes. The best part was putting on the make up, and doing my long curly hair in a feminine style. I have feminine facial features, and I'm chubby in quite a girly way, with big sissy-boobs and a round bum, so I looked pretty good with all my make up on! I love getting dressed up anyway, but this time it was even more intense because I was doing it for him.
I stepped out and he whistled. "Turn around" he said. I couldn't believe I was doing it, and already breathing so heavily. I was as turned on as i've ever been. I sat down next to him and we started to kiss passionately. His hand went slowly up my leg, and I was feeling his throbbing dick through his jeans. I couldn't wait, I had to finally see it.
"Can I see your cock?" I said breathily. He nodded and unfastened his trousers, and his beautiful stiff uncircumicised cock sprung out of them. "Oh Steve!" I said as I looked at it. "Mmmm!" I wasn't surprised to see it was quite a bit bigger than mine.
"Let me see yours" he said, and I couldn't wait to show him. I pulled my frilly knickers down my ankles and then lifted up my skirt to show him how excited I was. He stared at my hard dick and I loved it.
After that we just did what came naturally, which was slowly stroking eachother's hard cocks as we kissed passionately. It felt so good, but I knew what I had to do next. I pulled his hands to make him stand up, then got down on my knees. I then slowly licked his cock, like a good girl.
When I took his cock into my mouth, it was amazing. I slowly licked and sucked his hard dick for about five minutes. I only very gently stroked my own, because I knew that if I tugged my clitty hard while I had his dick in my mouth, I'd make sissy spurties right away and I wanted it to last. :)
All I'd imagined was that I'd maybe suck his dick, and swallow his cum, but what he whispered next excited me so much. "I want to be inside you" he said. My first thought was "But you are inside my mouth!"....then I realised what he meant, and I didn't think my face could get any redder. I stopped sucking him and nodded. I wanted it.
i got up and went to the toilet to grab my lube. I fucked myself with dildos but never a real cock before, so luckily I had lube on hand and I I knew I could take it. I handed the lube to Steve, and he took control.
At this point I was wearing my full sissy outfit, other than my knickers, and that's how I wanted to be as I got fucked for the first time. Instead of bending me over like I expected, Steve pushed up my legs so I could look him in the face as he fucked me. I couldn't wait.
He lubed up his own cock, and then me. I felt his hard cock slowly slide into me, and it was one of the best feelings in the world. It took nearly ten full minutes of the most exciting, heart pounding pleasure I ever felt to get his huge dick inside me. He went slow, which I loved.
Once he was fully inside me, it felt incredible. His hot cock was so, so much better than a cold dildo! I also felt like such a girl, such a slut, with a hard dick inside me. As he began to slowly fuck his cock in and out of me, I was in heaven.
"Oh Steve! Oh Steve!" I said as he fucked me. I LOVED it. Neither of us lasted very long. After the first minute of fucking his cock in and out of me slowly, he speeded up a little, and as he did he started to tug on my little clitty which was so excited.
I came first, and my clitty spurted a lot, which is unusual for me as it just dribbles usually. It was the most intense orgasm I have ever had. Steve came inside me almost 30 seconds later, and he seemed to enjoy it too!
Being a little sissy slut for Steve was a great experience. I still don't describe myself as gay or even bi really. I'd never fuck a guy without all my sissy clothes on. I just think that pleasing a real man is part of being a sissy, and being fucked by a hard cock is the ultimate sissy submission!
Steve and I aren't going to make a habit of it, and I doubt I'll do it with anyone else anytime soon, but if I ever get cuckolded I might do it then, in front of my girlfriend/wife for her to laugh at the sissy cocksucker. I'd love that! :)
