M(36) my first 19MM gay experience
My first bi experience.
When I was at university I (19) had a bi sexual friend, we shall call him 'Tom'(18) (not his real name.)
We were housemates in the first year and became best friends. At the time I had only experiences with women and thought of myself as straight. He himself was a virgin.
In the second year, one night watching some adult tv we were talking about being horny all the time. We'd had a little to drink. He suggested he didn't mind if I wanted to jerk off. I was hesitant but eventually though 'why not' and soon we were both sitting there jerking off watching porn.
I am 6'3 broad with dark hair, I was clean shaven at the time. He is about 5'8/9 with slender build. We did this a few more times, I didn't really look at him while we were stroking ourselves but evidently he was looking at me because one night he complimented me on my cock. It's about 7.5 inches while his is about 5 inches, I laughed and thanked him. He asked if he could stroke it, I could just sit back at relax.
I was surprised and initially I refused but he said he wouldn't tell anyone, he just wanted to do it once. I thought about it and let him do it. He reached across the sofa, took it in his surprisingly soft hand and just started pumping. Even though I felt hesitant I relaxed into it, I put my hands behind my head and let him jerk me till I came on his hand. It felt pretty damn good. A week later we did this again and again and again until it became a regular thing. To prevent anyone walking in we would sit on the bed in his room or mine while watching porn.
I was still hung up on m/m stuff so I never touched him and just let him stroke me. However, after about 2 months while stroking me he asked if he could use his mouth. I was pretty close to cumming so I just said yes. It was the best blowjob I had ever had, he licked and sucked and it felt fantastic. I came in his mouth and he swallowed it all. The next day I didn't know what to think but that night he did it again, this time sucking me from the get go. I felt it was only fair to do something so I would jerk him while he sucked me. This was when I started to feel really confused, I was really excited by what we were doing but still thought of myself as straight.
When I asked him about this he just said enjoy it. He admitted he had a crush of me since the first year and he had wanted to touch me for a while. I was kinda touched by that.
After about of stroking and blow jobs he asked me if I would be his first. He wanted me to fuck him. He said he was cool if I said no. I wasn't sure about taking this step but I eventually agreed.
I was nervous and excited; I'd never had anal sex with a girl before and now I was going to do it with my best friend. It turned out to be a really romantic night.
We bought plenty of lube, had a bit of music going and locked ourselves in his room. He stroked me to get me hard. He got on his hands and knees and I applied lube to his hole and tried putting a finger in to get the lube inside. He really liked that feeling. I put on a condom and lubed myself up and very slowly tried to push in. It did not go well, he couldn't seem to relax his ass and there was a lot of resistance. He insisted I kept going and eventually I got a couple of inches in. He said it hurt too much and we stopped. He suggested he should try getting on top. We applied more lube and he climbed on top of me and tried lowering himself on to me. This seemed to take a really long time, but seemed so erotic. I stroked his cock a bit and eventually he got me all the way in. I think controlling the speed and depth himself helped with the pain. He stayed still for a while before he started to ride me slowly. It didn't take long for either of us to cum, he came on my chest while I came inside him.
We stopped for a break and then tried again this time doggystyle again, this went much better and I was able to fuck him faster which he loved. We did it three times in total, lastly with him on his back.
