In my early 20s I went through a devastating breakup. My girlfriend of several years admitted to fucking one of my friends. I went into a depression and filled the void with porn and eventually, random sex. I got really into TS and gay porn on top of my regular stuff. I found myself browsing craigslist personals in search of my first gay or trans encounter. Trans was a lot harder to find in my area. This was the days before grindr and I didn’t like the exposure of a dating site.
I found a guy looking for mutual fun in an adjacent city, roughly a 90 minute drive. He was my age and moderately fit. White with brown hair and hazel eyes. Not weird looking, and I really didn’t have a gauge for attractiveness in men. Not feminine at all, which might have helped later, but I didn’t have a lot of options. Most of the guys on craigslist were way older, overweight, and extremely hairy. That’s a hard sell for a guy who’s only been with women.
I nervously drove the 90 minutes to the guy’s apartment building. I considered turning around several times but I was horny. Parked outside and he met me at the building door. We exchanged pleasantly and he lead me inside. It was dark out so that help my desire for anonymity. I let him know if never done this before. He had a nice apartment in the city and made decent money. He said we had to be quiet so as not to wake his roommate.
We stripped our clothes off and got into bed. I was nervous at first so we started just exploring each others bodies. He was fit with abs and a little chest hair. His body was harder than I was used to touching with the women is been with. His smell was different too. Not bad, just not like a woman. I was hard a a rock but not feeling it at the same time if that makes any sense. We kept exploring though and my hand found is cock. He was rock hard and HUGE. I mean, I’m slightly above average in length but I have a girthy cock. Like a can’t fit into a toilet paper roll. This guys was massive. I think he was at least 10 inches and thick. Like my fingertips barely touched when I wrapped them around.
I decided to take the plunge and started trying to suck his cock. It was difficult with the size. I could barely take him in my mouth and I was trying really hard not to scrape him with my teeth. He seemed to enjoy it. All kinds of new sensations flooded me. The feel of his head, soft yet hard at the same time, his precum, that tasted slightly bitter and made me think of urine, his soft moans and writhing as I stroked and licked, his hand on the back of my head. I tried to make it wet and slippery like I’d seen in porn but my mouth felt dry and I was getting tired. I kissed up and down his shaft and would have taken his balls into my mouth had they not been hairy.
He rose and went to the bathroom and I rolled onto my back. He came back with some lube. He lubed my cock and began to stroked it which felt great. Then he started sucking. I was conflicted. His mouth was wet and warm, but I could feel his stubble scratch and tickle when he licked my shaft. Definitely didn’t love that. I asked if I could fuck him. He politley declined saying he was more of a top, and that my cock would probably hirt him. He continued to stroke me as he leaned in and kissed me, full on the mouth, sticking his tongue in. It was sloppy and I definitely hated it. To this day I can’t kiss a guy on the mouth when we’re being intimate. It’s a huge turn off. I pushed him away gently and he moved to kissing my neck and shoulders. The whole encounter was very intimate. That was much better, but at the same time I could feel his massive cock resting right between my ass cheeks, sliding up and down gently and he stroked and kissed me. It felt great. It felt amazing. It was terrifying. I was always the more dominant one in bed. I’d never felt so submissive in my life.
That was the point I ended it. It was too much I was straight. I was into girls. I told him to stop and that I had to go. He was a little shocked. He assured me that we weren’t going to do anal, but if already made up my mind. I was dressed and out of there. I felt dirty the whole drive home. When I finally got home I beat off furiously to some straight porn and went to sleep. The next morning I woke up to a text from him complaining of blue balls and asking for another chance. I ignored him.
Since then I’ve explored more. I’ve been with men, women, and transwomen. I love them all. I guess I’d consider myself verse. I’m most likely bisexual but I could never do anything but sex with another man. Like I said, kissing men is still a high turn off. Also, I learned that I can’t bottom after I’ve cum. To this day my biggest regret about that encounter is that I didn’t take him inside me. I’ve only had one other cock that was close to that size and it was a Transwoman. I often fantasize about that night now, except this time I don’t run away. This time I let him lube that massive cock up and penetrate me missionary. I take every inch of him as he thrust slow and deep and when he’s ready I take his entire load in my mouth. Oh well, life is full of regrets.
Source: reddit.com/r/gonewildstories/comments/cihce5/first_time_with_another_man_mm