Early this year I messaged a younger trans guy who was looking to start hooking up with people. His partner had “a slutty phase” and wanted him to have the same experience, but he was anxious about meeting a stranger, so he was planning to have her come to watch and encourage him.
Moreover, he was essentially a virgin and wanted to be eased into having sex at all. I’d done this for others before, and actually helped another redditor with their first time a couple months ago, so I was eager for the opportunity. Plus, I’d get to help out a trans couple, which is who I prefer (DMs welcome! 👀)
We exchanged face pics after a couple messages and really hit it off. I’m really into twinks, and he’s really into physically larger guys. Since there was potential, we started exchanging porn clips to figure out what kind of sex he was interested in having. It was an interesting combination of gentle and caring, and violent or even taboo.
He’d mentioned filming was a kink, so at some point I sent video of me roughly fucking one of my FWBs. He responded:
“I wish that was me…”