I often fantasize about the shemale escort thing too... Something about a nice cock and nice tits at the same time.. mmmmm.
I fantasize about this kind of thing quite a lot, but I'm too chicken to make it happen. That said, I have done a few crazy things myself in my younger days. I was on Craigslist myself from time to time, and I eventually met up with a dude who I thought seemed to be cool and had a nice cock. Turns out the guy was really old and fat in real life, so it sorta burst my bubble. I was a teenager so I wanted to fuck someone maybe around 20 or 30. This was back in the day when we'd trade photos via Yahoo mail, so I didn't really ask him for a full body pic at that time -- and I was a stupid teenager. He ended up being nice though, I sucked his cock and he sucked mine, then I finished in a sock. I felt kinda gross though, so I just left after that and never talked again.Back when finding a good fuck on Craigslist was still a thing. I had come into a couple thousand bucks. I rented a mid expensive hotel for a week and hit Craigslist. My goal for the week, SUCK COCK and lots of it.
The second time I used Craigslist, I met someone who showed me some pics that they were a shemale, so I met them at a seedy Motel (again crazy me). Turns out they were a crossdresser, but I had a beer then just fucked them from behind until I came, then left. Super anonymous.
I also was part of Yahoo groups for a while, and I met up at a pornstar's party where she sucked many dudes off and let them cum in her mouth. She was a MILF type, so I just jerked off with other dudes while watching her get bukkake'd and then I proceeded with my turn to cum into her mouth. It was a bit hard for me to cum while other guys were watching but I just shut out the thought and did it anyway. In retrospect, I really liked that pornstar a lot more, and now she makes me hard a lot when I think about eating my own cum; I imagine her telling me to do it and her enjoying cum loads too.
I stopped using Craigslist though because it was always sketchy and I'd hear about people getting shot or robbed or both. So I am wiser in the sense I no longer risk my life to meet up with people I don't know, but I still often think about the fantasy of meeting up. A lot of my old college fantasies creep in from time to time, so I often think about the times when I'd be in the college men's bathroom where other dudes were showering and I'd read all the dirty writings on the toilet wall about sucking cock or calling for a good time. I jerked off a lot in college, and my favorite porns were of college guys jerking off together and eating cum. I think that's probably how I stumbled into these forums -- had a huge cum fetish back then and still do today, a lot of it is fueled by these fantasies.
I got married as a straight guy in real life, so it's way harder to do anything; but if I'm by myself I kinda revert to being "bi/gay" since I don't give that side as much attention. Lately been just using my VR devices like Oculus along with a bunch of Fleshlight and anal toys I have to simulate I'm fucking hot shemales or getting fucked by hot guys and then eating cum loads; I even bought fake cum to put all over my face if I want to pretend I'm being blasted by some hot pornstar in the VR. Clean up is super easy after; always just a quick shower, then hot tub and good read of these forums!
My biggest fantasy is to get with a shemale. I had set something up with an escort but got scared and didn’t go. I’ve been fantasizing about shemales for a long time.