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 :)