how to have sex with a shemale? tips?

[BlueVelvet8]

I'm attracted to feminine ladyboys and even went to see one, and it all started off pretty well. We both put on condoms and she was sucking my dick and I was sucking hers. But she got very horny and said "you have a very nice cock" and then begged me to fuck her. I have never done anal before, either with a woman or with a ladyboy, so I didn't really know how to do it and felt pretty uncomfortable, so I was unable to stay erect enough in order to enter her. How do I get over this, so that I will be able to be comfortable enough to have anal sex with a ladyboy?

Anyway, she finished me off with a handjob and I sprayed 4 times, so it was a pretty good cumshot. I'd like to go back to her but I want to know that I'll be able to satisfy her this time. WHat is you guys advice?

[virtualflowe]

My experience: I've never been able to fuck anyone anally.

Not for the lack of trying - it's just that I am not that long and I am prone to premature ejaculation.

So generally what happens is that I try to penetrate, then cum before I do :-(

My advice to you, get so much foreplay with your gurl that you are past the point of caring that you will be penetrating her - and just go for it!

Originally Posted by BlueVelvet8

I'm attracted to feminine ladyboys and even went to see one, and it all started off pretty well. We both put on condoms and she was sucking my dick and I was sucking hers. But she got very horny and said "you have a very nice cock" and then begged me to fuck her. I have never done anal before, either with a woman or with a ladyboy, so I didn't really know how to do it and felt pretty uncomfortable, so I was unable to stay erect enough in order to enter her. How do I get over this, so that I will be able to be comfortable enough to have anal sex with a ladyboy?

Anyway, she finished me off with a handjob and I sprayed 4 times, so it was a pretty good cumshot. I'd like to go back to her but I want to know that I'll be able to satisfy her this time. WHat is you guys advice?

[a9127]

Not getting “hard” happens to every guy at one time or another (except in porn movies… ) I wouldn’t worry about it. I think virtualflowe gave you some good advice. Spend a lot of time on “foreplay,” relax, and have fun! You could also let her get on top but if you’re not real hard she will have to be very careful and not get too “wild.” Or as girish suggested, let her fuck you.