Note: It’s very likely I will unintentionally misuse current gender roles/labels. Ignore it, even if it really kills you. Unless I misuse the oxford comma. Then have at me.
Years ago I used to enjoy going to bars where TS women would host get-togethers and a good time. Sometimes it would be a front for escorts, sometimes just people with like-minded interests getting together for a potential good time. Even though the majority of people I’ve slept with are women, If I had to put a label to myself, I would say I’m more bi than anything. When I would go to these parties I was usually drinking. Not because I was ashamed about what I enjoy, but because I was nervous to be around the people at the party. I didn’t know what to say or do or how to act. The only thing I knew was that gay men and TS women loved me. Just loved me. They liked to flirt with me, rub my hair, touch my lips, and sometimes grab my ass. I’ve always loved attention. I knew I was good looking and that was part of it, but there was a certain appeal and attraction to these people who were so outward and direct with me. It was a drug for me. I knew when I would go to these places that I would be touched and flirted with. Maybe they sensed my nervousness and my uncharacteristic shyness. Maybe they just truly loved my lips and imagined them wrapped around their cocks. I don’t know. It just worked.
This night I was in NYC and at the last party I had luck finding someone there. To be frank, I don’t recall that sexual experience too much. It was this particular one I loved. I was already a bit tipsy and proceded to have a few drinks. I was being flirted and touched with by a few beautiful women but I ended up talking to a hispanic woman. She was a bit younger than me, in her early 20’s, and attractive (I think). We talked, kissed, groped, and she invited me back to her place.
I went against my better senses here. One of the alluring factors was when she whispered in my ear that she hated condoms as we walked towards a cab. The other was that we went all the way to Washington Heights. No clue what I was thinking there. That’s a ridiculous place to get a cab heading anywhere.
When we got back to her place, it was obvious she was sharing it with others, but we went off to a cordoned off area and got naked. She was slender and small. We made out passionately and kissed each other all over. I was on top of her, kissing her when she spread her legs and guided my cock inside her. I never saw her getting the lube, I had no idea how she did it so deftly. I was inside this insanely passionate person feeling their tight ass squeezing against me. I was in heaven and threw all caution to the wind. I went slow, enjoying every part of me going in and out while she moaned into me. She preferred us being close and it was hot.
There was a point where she asked me to stop and switch. Nervously I got on my stomach as she instructed and felt her enter me. It was like something I’ve not felt before. I’ve been fucked in my ass before, but sometimes they were too rough, too eager, too big, too everything. This time, this time it was like heaven (or the alcohol numbing me). It probably helped she wasn’t that big, but I’ve never felt a sensation like that. At least not for many years . She was hitting every spot. I was in ecstasy but also scared to hell. I did not want this random persons cum inside me no matter how much it turned me on and she was intent on cumming. She was going hard inside me, loving how tight I was. I had to put an end to it. I had to stop it. She wasn’t happy but I made my excuses and left. We both didn’t cum and she was mad at me.
To this day, I’ve never felt anything like that. I can’t figure out if it was the position or her. I’ve tried to repeat it with others but the guys never want to do that position. She was the last non-pro transgender person I was with, but the ones after her were so damn good at what they did I didn’t mind. I do have to say I’m very lucky I didn’t catch anything. That wasn’t the last time I’ve done risky sex with random people, but It was certainly one of the top 10 idiotic sex-related moves on my end.
Source: reddit.com/r/gonewildstories/comments/c6c6mn/a_night_out_at_a_tscd_bar_mt