The Sleepover

When I was in college, I would spend the night at a friend's house whose parents lived close to the university. One very hot night we were sleeping only in undershorts in the same bedroom. We were both virgins and started talking about girls and both got a little hard. One of us suggested that we "practice" how we would fuck a girl, so we took turns being on the bottom, while the other dry humped the bottoms' crack. From the start, I always wanted to be on the bottom because I loved the way his dick felt rubbing my across my anus. We did this a few times and even tried kissing (for practice of course). One time he lost his load on my back.

On another occasion, when my friend was humping me, I was really excited as his dick head was sliding through my butt crack, and it 'accidentally' caught in my anus. The slight intrusion felt so good I told him to keep doing it. He managed to get the point of his dick about 1/2" in, but no further. At this point we knew that we were in new territory. Next sleepover I noticed a jar of vaseline in the bathroom, and used it to lube my tight little hole. When we were in bed spooning, I felt his warm little prick on my back side. When he started to hump me his dick was sliding easily between my virgin cheeks. I was so turned on by the sensation of having my anus rubbed that I reached back and guided his dick onto my now oily little indentation. He pressed in and it hurt like hell. I winced, but he grabbed my hips and pushed into me. In what seemed like forever, but was less than a minute, he ejaculated inside me. We repeated this on the next sleepover and I started to like the way being fucked felt, but it changed our relationship because we both knew this was queer. I tried pulling away, but he said he would tell all our friends I was a fag and that I begged him to fuck me.

One night his brother came into the room and asked what we were doing. He sat down on the bed and he was in his boxers, but I noticed he had a huge erection, and we all compared dick sizes. I admired his size with it bulging veins, and asked if I could touch it and he said yes, so I wrapped my hand around his big warm hard cock but pretended to recoil. Later that night, when I returned from using the toilet, big brother asked me into his room. I sat on the edge of his bed and he had the same big erection. He asked if I wanted to touch him again and I said yes. And gave him a hand job and he spurted his hot cum all over my hand. He said he saw me getting fucked by his brother and wanted to do it too. I told him I didn't think it would fit, so he said I should suck his cock, which I had never done before. Long story short, I sucked his dick for a minute and he came instantly filling my mouth with his hot goo. I was so surprised at the volume and taste that I spit it out. What happened after that was that I also became his bitch, and he eventually fucked me with his giant cock. My friend discovered us one night and became jealous and started with the threats again, but I just told him to stop bothering me and he did except for veiled threats.

It got to the point where big brother and I couldn't carry on at their house any more - too many fluids, noises, an suspicious eyes to hide from, so we met after class in an abandoned house in the neighborhood. One afternoon, I was summoned by him and inside the house was a mattress. After I got there he threw a piece of clothing at me. It was baby doll nightie from his sister. I acted put-out, but loved putting it on feeling the soft polyester and lace, and then servicing him. This is how it was for a while. I let my hair grow a bit and tried lipstick. We would meet a couple of days a week in the vacant house, where I would get girlie, suck his dick and get fucked. Eventually I moved away and had a more normal life. I denied it until after college and I was living alone. One day I saw a dress in the window of a second hand store and couldn't resist buying it with a lame story about it being a present. I later got to know that store very well as I started collecting women's garments. That led to the online hookups I am describing in this diary.