Dear Jamie,
I have a transexual fantasy that gets me so horny like nothing else. I love pre-op transgender women most—the contrast of breasts and soft skin and curves with a male appendage. I love cis women too, but my orientation is mainly towards this type of transgender woman.
I want to be fucked by a woman like this. I use anal sex toys and I want to be penetrated with the real thing. But if I write this in my online dating profile, I don’t get much in way of response.
I could solve this problem by seeking a gay male partner for anal. The cock is central to my desire, but it’s the fact that it’s on a woman that is hot for me. The excitement of a woman’s secret, and that she can reverse the roles and penetrate me.
I have also tried not putting my desires in my online dating profile and bringing it up with transexuals I get involved with. Most of them want ME to fuck her up the ass, or to give me blow jobs.
I honestly don’t know what to do and am really hoping I can someday have the kind of sex I’ve always wanted! – Jeffrey, 49
Hi Jeffrey! Thank you for being so candid and direct because you’re not alone. Many trans admirers are attracted to TS girls in general, but many are attracted to pre-operative trans women uniquely, and you are not the only man who is turned on by these thoughts.
There are some good reasons, however, why it is proving so difficult to realize your fantasy.
For the vast majority of transgender women, her connection to her penis is not like the connection a man has with his. In other words, while she may have experienced pleasure or used it to urinate, the mechanics of having a penis feel disconnected from her because she is really female, not male.
Many transgender women still experience pleasure and orgasm because the penis is what is there, but she may feel as if it’s a pussy or that it doesn’t work like it does with men.
Then, when a trans woman is taking hormones as part of her treatment, the cock often stops functioning and erections may be weak, and orgasm becomes more difficult.
Those trans women who work in shemale porn may be the exception, but remember they are actors. They also may use testosterone for filming, steroids, or any other number of tricks.
This still leaves you and your desire unfulfilled!
Some fantasies don’t have a realization. We all have imagined things that are simply unlikely.
That said, there are some transexuals who can and do use their cocks for fucking men up the ass. I would research transgender dominatrixes and you may find some success there. I advise you to keep a dating profile running that is respectful but direct. If and when a trans woman who shares your fantasy, and can fulfill it, finds you, you’ll be happy you did.
The realistic option however is a compromise that will feel fantastic but requires some imagination. When you’re with a trans lady, she can fuck you using a strap-on. It might seem strange to use a strap-on dildo when she already has a dick, but if you think of the fact that she is a woman, it makes sense that she needs to strap on an artificial penis in order to penetrate you.
Take my word for it—as a woman who has made love to a few trans women in my day, and a woman with a hungry vagina AND asshole, I keep my trans and cis girlfriends’ well stocked with an array of fun strap-on toys. Give it a try.
Tell us what you think