Author: windycityboy20

21[M] First Gay Experience

My whole life I’ve considered myself straight and have had girlfriends. The only experience I’ve had with another guy was a few drunk make outs. This past semester I decided to live by myself.

The last few girls I’ve gotten with, I wasn’t as turned on and had troubles staying hard. It made me curious about being with another guy. I always get turned on watching gay porn and surfing gay Reddit pages. I decided to give Tinder a shot to maybe find a guy to hookup with.

My experiences on Tinder weren’t great at first. I had a few conversations and flirted a little but was always too afraid to actually meet up. I matched with a much older guy in his 40s who messaged me right away with a long paragraph about just wanting a friends with benefits. It was Sunday afternoon and I was pretty horny so I told him sure and said I could host. I told him to bring condoms and lube since I didn’t have any. Read more »

22[M] My first and only Trans hookup on Spring Break a few years ago

I was on my first Spring Break in PCB a few years ago with some of my fraternity brothers. It was one of the first nights and I was way too drunk at the bar so decided to leave by myself and walk back to the hotel. The walk was kinda far but I thought it would help me sober up.
While walking back, a car pulled up next to me and asked where I was going and offered a ride. I normally don’t get in the car with strangers but she was a hot MILF and I got tired of walking.
It didn’t take long before she asked to suck my dick. I immediately thought something was weird about the situation but on my first spring break, and I wanted a good story so I said sure.
My guard was definitely up. She pulled into a subdivision and we started making out and she gave me some of the best head I’ve ever had. I was still pretty drunk so I didn’t cum. After a bit she stopped and drove me back. At that point, I had no idea where we were and couldn’t figure out where my hotel was.
While trying to find it, she was asking me questions about my fraternity and myths about sucking dick during pledging and if I would ever do it. She kept going on about it and it soon clicked that she might be trans.
I’ve never thought about doing it and maybe it was the alcohol but I reached over and grabbed her thigh and said I would try it. She pulled down her pants and there it was… a nice size cock and I started sucking her while she drove. I don’t think I was very good but she seemed to like it.
We decided to go back to her hotel and once we got there we both started sucking each other at the same time and I got so horny that I told her I wanted her to fuck me.
She laid me on my side and lubed me up with her fingers before sliding in her good size cock. It hurt so bad at first but definitely helped being drunk. After a few minutes it started to feel absolutely amazing. We then switched to missionary with my legs on her shoulders made it feel even deeper. I ended up cumming without even touching myself. To this day, it was the best orgasm I’ve ever had.
She pulled out and came on my stomach. I had two big loads on my stomach then she got me a towel to clean up. I felt regret after and left in a hurry. She gave me her my number but never responded to her calls/texts. Looking back on it. It’s definitely something I’d try agin.