Jacking off with a friend turns into much more Sex Stories Cool – Y2Stories

I make the transition from fully heterosexual male to crossdressing sissy slut.

I was single, in my twenties, and very much heterosexual. I had always liked girls but didn’t have a girlfriend at the time. I was addicted to porn and was constantly ordering VHS porno tapes. This was before the internet. An acquaintance of mine named Allan had heard about my porn collection. He mentioned it one time, and I casually invited him to drop by sometime and watch some tapes. Two days later he was at my door with a six pack and a smile. We got comfortable (he on the couch and I in my recliner), drank our beers, and I put in a porno tape that had mostly black men with huge dicks fucking white women. We watched several videos and I noticed that from time to time he would rub his crotch with his hand. The next tape featured transexual shemales (chicks with dicks). It was not something that most people knew much about back then. As the video began, two shemales were picked up in a bar by two white guys, and then they went to an apartment. After some kissing and flirting, they got down to business. When the two shemales undressed, I looked over at Allan and his eyes were about to pop out. He was looking at their big tits and their hard cocks and now he was openly rubbing his cock through his pants. He saw me watching him and he said, “You know what this makes me want to do?” I didn’t answer except to excuse myself and leave the room. When I returned from the bathroom, I had a bottle of hand lotion. I undid my belt and pants, slipped them off, and got back in the recliner. As I told Allan, “I don’t want to get lotion on my pants.” I then pulled my penis out of my underwear, got a squirt of lotion, and said, “Help yourself to the lotion” as I began to casually jack off. I could tell that he was excited. He wasted no time stripping off his pants and he wasn’t wearing any underwear. His cock was already very hard and I was a bit envious. It was quite a big longer and fatter than mine. Allan sat back down on the couch and began to jerk his hard cock. The two of us sat there jerking (I was secretly watching him stroke his beautiful dick) and at just the moment in the video where a guy began fucking one of the shemales in the ass, he started spurting his hot cum straight up in the air. It was a huge amount of cum. I got up and went to the kitchen for some paper towels which I gave to him. I commented on how fast he had orgasmed. He assured me that this was not typical for him, but that he had never seen transgender porn, and that it definitely aroused him. After cleaning himself up, he thanked me for hosting him, and I told him he was invited to come back anytime. After Allan left I returned to my recliner and continued with my own jack off session, but I wasn’t really paying attention to the videos. I was thinking about Allan’s big hard beautiful cock and how it had spurted hot cum so high in the air when he orgasmed. Then I had one of the best orgasms I had ever had.
About three days later Allan called and asked if he could visit again. I anxiously said yes, and I prepared for his arrival. I had two more transgender videos that I hoped would turn him on. Once again when he arrived he had a six pack of beer. We drank one each and talked for a bit, and then I put in a video. The first one was about a huge black tranny with gigantic tits and milk chocolate nipples and her white boy slave. She had that white boy sucking on her enormous prick and begging to be fucked. I got up and went to the bathroom for the hand lotion, but when I returned and took off my jeans, I was wearing some pink lace panties underneath. Allan’s eyes got big when he saw me wearing girls’ panties. I explained to him that I liked the way that they felt and that I sometimes liked to crossdress when I was alone. Then I said, “Watch this!” I walked behind a wall, tucked my dick up in my ass crack, and returned. “Which do you think is sexier” I asked him. “This (I pointed at my crotch) like a girl? ” Then I slipped back behind the wall and stroked my dick to and erection and came back out. “Or this.” I asked. My hard cock could be seen clearly as it bulged behind the silky panties. Allan did not hesitate to respond. “I like the second one best,” he said. “Me too,” I replied. “Boys are so much sexier than girls. Girls just have a slit while boys have things you can actually play with. I sat back down and we began to jack off just as we had done before. Watching his hand stroking up and down on his magnificent cock was doing something to me. I was getting so very horny. I asked him if he jacked off a lot, and he replied that he did. I said that I did too. Then I took a chance. “Have you ever been jacked off by another guy? He said, “no.” I got up from the recliner and walked over to him. “Would you mind if I did it for you?” I asked. He seemed a bit nervous, but he said okay. I squirted some more hand lotion on my palm, and reached for his dick. The head was already quite red and his cock was rock hard. I began to stroke…slowly at first and when I noticed his reaction. He had closed his eyes and tilted his head back and was starting to moan. I increased my speed, and in just a few seconds he was spurting cum all over again just as he had before. This time instead of running for paper towels, I asked if I could “borrow” some of his cum. He said okay, so I scouped up as much as I could in my right hand and then began to smear his jism all over my cock. I was using his cum as lubricant to jack off my own dick, and the thought of it was so sexy that I could not last long…I began to spurt long ropes of my own cum all over the carpeted floor. In Part 2, I hope to tell you more about my sexual adventures with Allan, and how we began to explore crossdressing together, and how I eventually seduced him into fucking me . (more later)