My apologies to the late Helen Gurley Brown, the long-time editor of Cosmo and the author of Sex and the Single Girl, but my title seems appropriate because sex can be especially tricky ground to negotiate when you start dating pre-op or non-op ladyboys.
Alright, sex can be a minefield when you start dating a cisgender woman, too. But there are special things a man has to take into account when he and his new TS girlfriend are ready to be intimate. And in case you’re wondering, almost none of this applies if she is post-op.
Love what your ladyboy girlfriend have or hate It
Perhaps the biggest potential landmine is how she feels about her genitals. A relatively small number of transsexual women hate their penis. They don’t want it touched or fondled, and definitely do not want you to perform oral sex. Early on, a man who is smart and caring will gently ask her attitude about it. The way I usually raise the subject is softly but directly: “So it seems like we’re heading towards becoming a couple but before I accidentally do something in bed that you don’t like, how do you feel about me touching your penis?”
Depending on the woman, sometimes I use a slang word. The question often provokes a laugh or smile, sometimes an embarrassed giggle. Only a very few women have said “Leave it alone.” But over the years, most told me in no uncertain terms something like, “I love having orgasms and if you don’t use your hands and mouth on me, we’re not going to be a couple for very long!”
Dating a ladyboy and getting her excited can be a challenge
Remember the effect of the female hormones she may be taking. Simply put, they can kill her ability to become aroused – and even take away her desire in some cases. Emotionally she may want you as much as you want her but the hormones may stifle her ability to turn vague desire into wanton lust. Hormone therapy can also have a negative effect on her ability to achieve a climax.
Rather than rushing into bed, I’ve found that fooling around on the sofa often turns the key in her body and her psyche. A prolonged “make out session” may seem like being back in high school hoping the girl’s parents don’t come home early but often it is a sure-fire way for your partner to turn on.
I don’t mean a few minutes of fast kissing followed by an impatient, demanding “Are you ready yet?” I am talking about long, slow, deep, wet kisses that seem to last until next week. Move your hands softly around the back of her neck as you kiss, down her arms, across her torso and abdomen, along the lower part of her thighs – but don’t wander into the sacred territory between her legs until she gives you a sign that she’s ready.
If all else fails there’s a pharmaceutical solution: A prescription for the “little blue pill” can work wonders if she is unable to become excited even if she is emotionally aroused. Tracy, the transsexual woman I lived with for five years, kept a supply for “just in case” as did some other T-women I have dated. But don’t buy the cheap versions sold on-line that you may find advertised in your spam folder. Health experts agree that they are almost always counterfeit and won’t work, and could be dangerous.
Ladyboys and their sexual roles
I can generalize about the sexual preferences of transsexual women based only on those I’ve known intimately. And I have found that just as each cisgender women’s sexual interests differ widely, so too do the desires of ladyboys. However, it is safe to assume that she will want you to initiate sex much of the time. She wants to feel like a woman and that means being “pursued,” even when you are in a relationship.
That said, don’t be surprised if she suddenly crawls all over you wanting it right now. Her sex drive and desires are likely as complicated as her personality. Some ladyboys I’ve been with were strictly bottoms because they didn’t like feeling as if they are having “gay sex” the way they did before starting their transition. A few wanted to be on top most of the time but they are the exception. Most are versatile and like variety in bed, and making sure that the man in their life is finding pleasure in her body as much as she is finding ecstasy in his.
The important thing to remember is that you are with a unique woman. Treat her with respect and dignity, and when you are making love be sure she always knows that you adore the woman gracing your life.