I’m a straightish guy but I love botto[M]ing for transwomen, and occasionally men.

I’d consider myself straight. I have a girlfriend who I love dearly and have never cheated on. Before we met thoug, I spent years sleeping around. I went through a rough breakup and started watching a lot of porn. Eventually transgender and gay porn. I started fantasizing about tasting cock. At the time, craigslist still had personals and escort pages. I found myself browsing them and masturbating to the ads. Eventually I got up the nerve to try a TS escort. I’d already been with several female escorts so that part didn’t really bother me. I met this trans escort at her apartment. She was a gorgeous athletic latina with a fat cock. I was nervous so she sucked me for a while before I got up the nerve to suck her. I’d had one gay experience before so this wasn’t the first cock is sucked. Afterwards I topped her. I came so hard in her ass and felt so dirty after.

Almost a year went by and I had the urge to try again. I’d had sex a hand full of times since then. Mostly with women. One guy that I met on craigslist. He sucked me in a show house he had access to and I fucked his ass on the floor. I just wasn’t feeling it though. I really wanted a trans woman. I’d started getting more into TS domination porn and wanted to try bottoming. At this point I’d discovered Eros.com, Backpage, and The Erotic Review. I was seeing escorts maybe twice a month from those sites. I found a knockout TS escort traveling through my area. Her reviews said exactly what I wanted. She was latina and had nice slim cock. My first experience bottoming wasn’t great, but I was addicted. Over the next few years I had a lot of sex. I saw more TS escorts. Got better at bottoming and enjoyed it a lot more. I eventually had a threesome where they took turns topping me. I upped the ante when I took a work trip to the Philippines. I was able to see 3 gorgeous trans women at once. I tried poppers with them for the first time and was in ecstasy.

All the while I continued to be attracted to women. I had a hard time committing to relationships because of my past heartbreak. Tinder was my best friend. I think I hooked up with 4 women for every TS escort I met with. Sometimes the escorts were cis women but I generally reserved paying for sex for the trans women since I was keeping that part of my life compartmentalized. As far as anyone is concerned, I was a completely straight man.

Seeing escorts is expensive though and sometimes I just had to satisfy my craving for cock. I tried grindr and craigslist couple times to find men but wasn’t comfortable with how close that got personally. It was then that I discovered cruising. I found a local adult bookstore with a theater and read the reviews on it. I went there and was incredibly nervous. It was 40 minutes from where I lived but even then I wasn’t comfortable having my car out front. My first visit was before I started bottoming. I went in and wandered around for a bit. It was dark and smokey. Found a younger twink dude and followed him into a booth. He sucked me in a chair before turning around and sitting on my cover cock. He worked his hips a bit and I think I came in about 30 seconds. This was maybe a month or so after my breakup. (I know this is all out of order. Bear with me. I’m going to write some more stories about individual events later. I went back at least once every few months. Eventually I started sucking men off. Only the guys my age or a little younger, or the older affluent looking guys in business casual with wedding rings. Always in the dark.

I moved for work a couple years ago and the place I live has a couple bathouses. One really nice one I frequented often. Far better than any adult bookstore. I love the music, everyone is clean, and the place has less of a creepy vibe. I preferred to get a private room so I could relax without wandering endlessly. I’ve had a number of experiences there, from orgies to bdsm. A month before I met my girlfriend I went to their bi night. I went into a private room with this cute alt couple and had shared the guys cock with his girl. I fucked her while taking him in my mouth and vice-versa. I fucked several other guys’ wives while I was there and also took some cocks. I had a blast.

I still only date women. I have no desire to ever date a man, although at this point I’d consider a trans woman. I don’t know. I don’t even really find men attractive. Every sexual encounter I’ve had has been in the dark of a theater or bath house. I’d also never cheat, so I’ve contained my dwindling urge for cock by masturbation.

Source: reddit.com/r/gonewildstories/comments/cigtrq/im_a_straightish_guy_but_i_love_bottoming_for