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