Transsexual Male / 22
Experience
As a transgender man, I'm not really open with my sexuality. I don't feel the manliest when I think about how I like men. I like both men and women, I'd pick up both at socials and hook-up every now and then. I was always a top when it came to men. Never liked anything inside me cause I would feel uncomfortable and less like a man.
There was this dude who I had a mutual friend with. He had soft eyes, black hair, freckles and all around handsome and a bit of a twink. I'm not one to be flustered but he hugged me one time and I blushed. I started to text him a bit more often, and eventually we agreed to meet up with just us. We had a great time, he was very sweet and I tried my best to be charming. We'll call him James. James and I hit it off and one day we were in my car. I made sure to play some music to get the mood going and we started making out. I moved down to his neck and made sure to leave a mark here and there. He was a fairly skinny dude, not a lot of muscle mass if any really. He was about an inch taller than me but I looked bigger out of the both of us. I felt him get hard through his jeans. I pulled down his pants and began to stroke his dick. I teased him with a bit of head as I had done with previous partners. I had a prosthetic on in order to top him so I had to use a bit of lube to get my cock inside him. I began to fuck him and as I did, I stroked his dick as well. He shifted and got on top of me to ride my dick. He was really good and I loved seeing his cock swing up and down as his him moved. I thrusted into him and reached for his cock to stroke it and after about a minute of that he came. We cleaned up and I took him home.
After a few more hook ups, he said that he said he wanted to talk to me. James asked if I'd be down to be a bottom. I was immediately hesitant but after a bit of convincing, I decided to try it out. He was really kind and said that if I didn't like it, we could do things just how we had been doing them before. I went over to his apartment and we immediately started to get things on. I was really nervous but also excited. I had experimented with my fronthole before but I wasn't too keen on it, but I never actually had a dick in there. He kissed down my body and removed my pants. He started giving me head and I had never had head that good. He sucked my dick(actually clit but I call it my dick in this case) and used a generous amount of tongue. I was gripping onto his hair and I started getting close. I told him that I didn't want any fingers up there so once I was really close, he pulled out his cock. When you're topping, dick size doesn't matter but when you're bottoming, it does. He didn't have a massive dick, it was fairly average, 5.5inches maybe, but he definitely knew how to use it. He got on top of me and started slow. It hurt for a second but after about a minute, my body relaxed and it started to feel good. He kissed at my neck as he fucked me and I pulled him closer. His stroke was insanely good, I could feel every inch going in and out of me.
I wanted to see how things felt if I was bent over in doggystyle so we rearranged things. Doggystyle felt even better. I felt even more of his cock and he began to pick up speed. He was moaning and I was biting the sheets cause it felt so good. He pulled out and told me to get on top. I sat down on his cock but wasn't really sure HOW I was supposed to ride him. He laughed and put his hands on my hips to guide me. Eventually I got the hang of it and didn't want to stop. He felt so good inside of me, I felt completely hazed over and all I wanted was him. He started thrusting into me as I rode him and thing he squeezed my sides. I felt something warm explode inside of me and I started cumming after him. I slowly got off of his cock and he immediately started apologizing for cumming inside me. I explained that he was lucky cause I had a hysto when I was 20 to remove the uterus (still hate thinking about that thing was inside me). We cleaned up and just laid in bed for a while.
We had a thing going for some time until he moved away after he graduated. I do miss him from time to time. I prefer topping over bottoming, but the only person I think I would ever bottom with is him anyways.
There was this dude who I had a mutual friend with. He had soft eyes, black hair, freckles and all around handsome and a bit of a twink. I'm not one to be flustered but he hugged me one time and I blushed. I started to text him a bit more often, and eventually we agreed to meet up with just us. We had a great time, he was very sweet and I tried my best to be charming. We'll call him James. James and I hit it off and one day we were in my car. I made sure to play some music to get the mood going and we started making out. I moved down to his neck and made sure to leave a mark here and there. He was a fairly skinny dude, not a lot of muscle mass if any really. He was about an inch taller than me but I looked bigger out of the both of us. I felt him get hard through his jeans. I pulled down his pants and began to stroke his dick. I teased him with a bit of head as I had done with previous partners. I had a prosthetic on in order to top him so I had to use a bit of lube to get my cock inside him. I began to fuck him and as I did, I stroked his dick as well. He shifted and got on top of me to ride my dick. He was really good and I loved seeing his cock swing up and down as his him moved. I thrusted into him and reached for his cock to stroke it and after about a minute of that he came. We cleaned up and I took him home.
After a few more hook ups, he said that he said he wanted to talk to me. James asked if I'd be down to be a bottom. I was immediately hesitant but after a bit of convincing, I decided to try it out. He was really kind and said that if I didn't like it, we could do things just how we had been doing them before. I went over to his apartment and we immediately started to get things on. I was really nervous but also excited. I had experimented with my fronthole before but I wasn't too keen on it, but I never actually had a dick in there. He kissed down my body and removed my pants. He started giving me head and I had never had head that good. He sucked my dick(actually clit but I call it my dick in this case) and used a generous amount of tongue. I was gripping onto his hair and I started getting close. I told him that I didn't want any fingers up there so once I was really close, he pulled out his cock. When you're topping, dick size doesn't matter but when you're bottoming, it does. He didn't have a massive dick, it was fairly average, 5.5inches maybe, but he definitely knew how to use it. He got on top of me and started slow. It hurt for a second but after about a minute, my body relaxed and it started to feel good. He kissed at my neck as he fucked me and I pulled him closer. His stroke was insanely good, I could feel every inch going in and out of me.
I wanted to see how things felt if I was bent over in doggystyle so we rearranged things. Doggystyle felt even better. I felt even more of his cock and he began to pick up speed. He was moaning and I was biting the sheets cause it felt so good. He pulled out and told me to get on top. I sat down on his cock but wasn't really sure HOW I was supposed to ride him. He laughed and put his hands on my hips to guide me. Eventually I got the hang of it and didn't want to stop. He felt so good inside of me, I felt completely hazed over and all I wanted was him. He started thrusting into me as I rode him and thing he squeezed my sides. I felt something warm explode inside of me and I started cumming after him. I slowly got off of his cock and he immediately started apologizing for cumming inside me. I explained that he was lucky cause I had a hysto when I was 20 to remove the uterus (still hate thinking about that thing was inside me). We cleaned up and just laid in bed for a while.
We had a thing going for some time until he moved away after he graduated. I do miss him from time to time. I prefer topping over bottoming, but the only person I think I would ever bottom with is him anyways.
