I took his virginity!
We've been in contact for a long time. He has been with trans girls before but never managed to get fucked because he always feels pain. I told him about my trick for first timers and he agreed to give it a try.
For those who don't know how my trick works, it's really simple: I let my cock get soft and push it slowly in, with a lot of lube. It doesn't hurt, because it's soft, but it's tricky to get it to go inside. Once I manage to get in, I start getting hard and it feels really good.
It was not easy with him. He kept squeezing his ass and it pushed my cock out. After almost giving up, I finally managed to get inside of him (if you wanna go straight to it, it was around minute 18) and he took a soft pouding (didn't manage to be fucked like a pro). After that, he fucked me and I rewarded him with my milk in his mouth.
Edit: I almost lost this video. Two of my cameras didn't record. Thank God I was filming from 3 different angles and one of them filmed everything 🙏🏻