This story happened several years when I was 31M and she was 28T.
Disclaimer: I’ll be using she/her throughout. Transwomen are women, sorry. ♡
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I met Monica on a transgender-focused dating site. She is my height, Pacific Islander but quite slim & fit with long black hair. I can’t remember how she told me but she let me know her porn star name (she had done solo/masturbation scenes) so I had already seen her nude prior to meeting. Between that and some things she had texted me, it was clear that we would absolutely be fucking and that I would be bottoming for her.
We agreed to meet at a known a gay-friendly bar. She was at the pool table with her friend, another trans woman who was very shy, skinny and quiet and wearing bland, loose fitting clothes. Total opposite of Monica who was loud, brash and pushy and wearing a dark red tight cotton dress that only went about halfway up her thigh, along with leather boots & jacket and big hoop earrings. There was another guy there who was apparently set up with the shy girl: he was a tall, pudgy bald dude who didn’t talk much either
As I walk up she announces “there he is! Come here!” Then kisses me deeply and squeezes my balls from the outside of my clothing. This is the very first time I’ve seen her in person. She tells me to go get a round of drinks, which I do. When I get back we start taking turns playing pool and she’s sort of annoyingly flirty, almost like trying to make people feel uncomfortable. Groping me as I made my shots and pulling up her dress as she made hers, so that I would know she wasn’t wearing underwear. At one point she reaches into my pants and grabs all my junk and says “lick my asshole when I play.” The place is not well-lit and not many people are there but it did seem like anybody would be able to watch all of this happen. So for the next couple shots I would get down on my knees to lick from her ass to her balls. At some point she tells her friend to play for her because she has to go to the restroom. She walks a couple feet away, turns and says to me “are you coming or not?”
She leads me to a stall in the women’s room, and sits me down on the toilet so I can blow her. She’s enjoying herself and not bothering to be quiet at all and saying stuff like,
“You love that dick?
“I was going to suck your dick on the drive home but maybe I should drive, you’re a good bitch.
“How do you like to be fucked? I didn’t say stop sucking!”
I’m really enjoying myself too because hers is thinner and shorter than mine is, so I can easily “perform”. I start to take my dick out to either jerk off or invite her to suck it. She pulls out and says “Nope. Later.” and then continues the blowjob by pointing her cock straight out with one hand holding my head/forehead with the other and saying “open wide” then doing long slow in/outs all the way before saying “okay, go ahead.” (Keep blowing like I was before). Eventually she quiets down and I realize she wants to finish. After some more work (I have no idea how long we were in there, but people came and went so several minutes), I get her cum in my mouth and she says “move, I gotta piss.”
I leave the women’s room and go to the men’s room to pee. I see myself in the mirror and I look like shit, with messed up hair, a wet face and some drips on my shirt. I’m annoyed but having fun. Meanwhile, karaoke has started up and she loves sing so we stick around for another beer or 2 each, and plans are made to go back to the girl’s house. I drive her in my car and get some road head. They apparently rent a finished upstairs room together in a house. It’s like a studio/1 bedroom apartment except there are two people living there. Nobody pretends like we’re there to hang out. The other couple go 10′ away and start making out and hooking up. We do the same, except before long she opens up her laptop and starts webcam streaming this all. She sucks my dick in a way to make herself gag and seems to enjoy it and she has me do it harder to her.
After that she’s standing on her knees and I’m in a doggy position sucking her (still on camera) when she reaches across my back and inserts a somehow-lubed middle finger in my ass and starts pulling me toward her to fuck my face. She pulls out and points my ass more toward the camera and does increasingly aggressive fingering with 2 fingers and jerking me and squeezing my balls as well.
She turns off the laptop and lays down indicating that I should get on top to ride. It’s at this point I realize that the last couple drinks are kicking in and she seems sorta sleepy and out of it. Nonetheless I rode her dick really well and eventually she tells me she’s cumming and I got so excited I kept fucking until she couldn’t take it anymore. She slaps my thighs really hard and curses at me a bit as I slowly wiggled my hips on her.
Not for the first time, I looked over at the other couple to see him penetrating her or her sucking him and judged them for being boring, haha. Monica turns over in a side-sleep kind of pose (one leg up, one leg straight) and mumbles to turn off her lamp and seems to almost immediately fall asleep. I’m still incredibly horny so I masturbate while continuing to lick her ass, and suck on her balls. She isn’t really sleeping because she is raising her ass and moving her hips around. Finally I cum on her ass and taint and lick her clean.
Then I go home with my head spinning.
We meet up one other time, watching movies and fucking then sleeping over and some morning sex. Never saw her again.
Source: reddit.com/r/gonewildstories/comments/e16uhz/mt_an_unforgettable_night