Ask QC: Should I Date A Trans-man? What Will The Sex Be Like?

My name is David. I met Johnathan at a local bar and we played a quick game of pool and traded numbers. We ended up hanging out the next weekend, going to his friend’s picnic and playing ultimate frisbee together. He’s fun, smart, competitive, and sexy—he has a deep voice, a hairy chest, facial scruff, and nice muscular calves. Here’s the catch though, he recently revealed to me that he was biologically born female.

It kinda blew my mind and I asked him a few times if he wasn’t kidding. He apparently started transitioning in his teens and pretty much passes for male now. The thing is, I see no hint of the feminine in him whatsoever—he’s all dude as far as I can tell. There’s just one little thing… I’m not sure whether I wanna date this fella and I haven’t really followed up with him yet because I’m kinda nervous about what the sex will be like.

I’ve done some research online and apparently female-to-male genital reconstructive surgery doesn’t always make the most attractive or functional dicks. I’m afraid that I won’t know what to do with his penis when he whips it out—will there be some pump involved? Does it feel sensations like my dick? Can it cum? Will I always have to be the top?

Even though I’ve never known a trans person before and I’m not afraid of dating Johnathan (OK, well maybe a little), but I just wanna know what to expect and how to please him. We’ve already kissed and I know we’d go a lot further if given a night together. Does anyone have any experience or suggestions?

Not every guy you meet is perfect, we all have our histories and our own unique sexual styles. Some people feel like they were born into the wrong gender just as some gays feel like they weren’t meant to be heterosexual. It’s cool that Jonathan’s trans-identity doesn’t have to be a deal breaker, but what can our advice seeker expect from the sex? Is there anything else David should keep in mind and would you date a very sexy trans-man if you found yourself in David’s position? Please share your advice and experiences in the QComments section.
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Apr 26, 2011 By paperbagwriter 17 Comments