if you read my profile you will see I am a gay crossdresser in my forties, but my master/boyfriend wants to see me dressed up having sex with a woman. Should I do it has I have never been with a woman before. As Katy Perry sang in her song I have kissed a girl but nothing else as I have only been attracted to guys before. The idea of going with a woman scares me a bit but I'm also finding myself wanting to try it, if only to see what it is like. I've never even fucked a guy never mind a girl and need advice.
Wow! Where did that come from?
Okay, I think your biggest problem is going to be mental. If yot can't get turned on by it then it's not going to happen. I honestly think that you might be better in a threesome.
My first time was a disaster but that was because I didn't fancy her at all. I got hard but couldn't cum, even after nearly an hour, so I gave up. I did get much better at it though!
I also think she should keep some lingerie on, the feel of it should help turn you on. Maybe find a dominant woman who can play on your submissiveness.
"insensitive prick!" – Danielle Algo
If you really want to try it, just go for it. I think her getting on top is probably the easiest way to start. Start exploring from there.
Enjoy! And please let us know what is was like.
=== Not ALL LIVES MATTER until BLACK LIVES MATTER ===
