Last weekend, I flew up to New York to be a date for a very cute boy…the only problem is that he likes dick, just about as much as me. I was his cover date, some of his family is very conservative and he just wasn’t ready to deal with the pain of coming out to them. It was a win for him and I got a free trip and hotel, with a much needed weekend away from the real world.
Brian and I have been friends since high school. He was like that gay brother that I never had. Secretly, I always wanted to fuck him. He’s never been with a woman before, on some level, I was curious if I could convert him. But I thought it would never happen.
But Friday night, after the wedding rehearsal, we drunk and alone in the hotel room. It was early, only like ten o’clock. We talked about going out and finding some bars, but we found some other entertainment.
We were talking and we were comparing notes. We were talking about giving blowjobs, anal sex and facials. We have a lot in common. He’s the bottom and I guess you can say that as a female, I’m always on the receiving end.
Out of nowhere, he told me that he had jerked off thinking about me a few times. I didn’t know what to say. It shocked me. He told me that he had imagined what it would be like to have sex with a woman, me in particular. I had always wanted to have sex with him, but it was more in a curious way, not the way I lust for most guys. I didn’t know what to say.
He started joking around about it, saying how crazy it was, how much he loved his boyfriend. I joked around too, but we were both curious and very horny.
Then I changed the mood, when I said “Let’s do it.”
There was definitely a feeling of nervousness as I started to unbutton my blouse. (I was actually dressed up for once) He starred at me, not saying a word.
I asked him if he had ever seen boobs before. And believe it or not, that lightened up or mood again.
He told me that he had seen Kelly’s, a mutual friend of ours. But he said her’s were half the size of mine and he had never felt any before.
I finished taking off my shirt, then undid my bra and let it fall to the ground. He had been sitting on a chair next to the bed, now he climbed on to the bed with me. He reached out and gently squeezed them. The way he did it was more playful then erotic and it made us both laugh.
He caressed them and pinched my nipples. He leaned forward and start to suck on my nipples. That’s when I went from just horny, to very turned on.
I let him play with them for a few more minutes, then I stood up so that I could take the skirt off. He starred again as I pulled down my panties. I asked him if it was the first pussy he had seen. When he answered Kelly again, we both called her a slut even, if it had only been when she was changing in front of him.
I laid down on the bed next to him and he reached over and started to rub my pussy. The way he looked at it as he was touching me, was different. He was definitely doing some exploring.
Then he slid two fingers inside of me. I let out a soft moan and he smiled.
After a minute or two, I asked if he wanted to go down on me.
He may have never gone down on a woman before, but his tongue did feel pretty good. I told him a couple of tricks and it wasn’t long before I was breathing hard.
That’s when I told him to take off his clothes. He has an amazing body. I told him about how me and the other girls would talk about how it’s a shame that he’s gay.
His cock was rock hard and pointing at me when his underwear came off. We looked at each other, neither of us really believing that we were about to do this.
I reached out and guided his cock to my pussy. Slowly, he pushed inside of me. The look on his face was sheer pleasure. He even let out some soft moans.
I wasn’t sure what to expect. He had the rhythm but not the technique. I felt like the older teacher, giving him more tips and lessons.
After a few minutes, I was really starting to enjoy it. We were really getting into it. The bed was shaking and our bodies were working well together.
Then he exploded, filling me with his cum. He collapsed on to me and I held him.
We fell asleep not long after that. The next morning when we woke up naked, we both looked at each other and smiled. I think he’s officially bisexual now.
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