I had a pretty good date with a woman last week. We spent the afternoon together then she came back to my house. It was my first time having sex with a trans woman - although I’ve been with men and cis women before. I really wanted to suck some dick (it’s been a while!) so I started by giving her a blowjob for a while before she returned the favour. It was really intense and I had to tell her a couple of times to slow down. We calmed down for a bit with just some hugging and touching / stroking and grinding. She bit me a lot and left some big bruises on my neck, which really enhanced the pleasure of her hands on my dick and made it a whole-body feeling. She then straddled me and started face-fucking me, which I’ve never done before. I don’t know that I liked it, but I was masturbating as she did so and I came incredibly hard, so part of me must have enjoyed it! I cleaned myself up (there was a lot of cum) and watched as she finished herself. Very successful date overall :)
As a slight aside, I was really happy with myself. I felt I communicated really well and although I felt she did less well there, we both really enjoyed ourselves. It’s something that I’ve been working on and I think I nailed it :)
So hot. You kind of buried the lede on messing around with a trans woman. The communication and such was great. Do you have any other notes on the experience? Would you do it again? How far do you think you’d go with her? :-)
No other notes really. It was nice. We’re almost certainly going to go on more dates together, but having sex is tricky logistically because we both live with other people. I did want to bottom for her but I hadn’t prepared so yeah… she did lie behind me at one point and just grind against me while giving a reach-around, which was a good alternative. TBH, I don’t know if she’d want to top me. We did originally plan for anal (me fucking her) but I got overexcited with the face-fuck so we didn’t get that far 😅. We’d been going for about an hour at that point so we were both happy to call it quits there for that day
I had a pretty good date with a woman last week. We spent the afternoon together then she came back to my house. It was my first time having sex with a trans woman - although I’ve been with men and cis women before. I really wanted to suck some dick (it’s been a while!) so I started by giving her a blowjob for a while before she returned the favour. It was really intense and I had to tell her a couple of times to slow down. We calmed down for a bit with just some hugging and touching / stroking and grinding. She bit me a lot and left some big bruises on my neck, which really enhanced the pleasure of her hands on my dick and made it a whole-body feeling. She then straddled me and started face-fucking me, which I’ve never done before. I don’t know that I liked it, but I was masturbating as she did so and I came incredibly hard, so part of me must have enjoyed it! I cleaned myself up (there was a lot of cum) and watched as she finished herself. Very successful date overall :)
As a slight aside, I was really happy with myself. I felt I communicated really well and although I felt she did less well there, we both really enjoyed ourselves. It’s something that I’ve been working on and I think I nailed it :)
So hot. You kind of buried the lede on messing around with a trans woman. The communication and such was great. Do you have any other notes on the experience? Would you do it again? How far do you think you’d go with her? :-)
No other notes really. It was nice. We’re almost certainly going to go on more dates together, but having sex is tricky logistically because we both live with other people. I did want to bottom for her but I hadn’t prepared so yeah… she did lie behind me at one point and just grind against me while giving a reach-around, which was a good alternative. TBH, I don’t know if she’d want to top me. We did originally plan for anal (me fucking her) but I got overexcited with the face-fuck so we didn’t get that far 😅. We’d been going for about an hour at that point so we were both happy to call it quits there for that day