Shemale Sampler: What Men Like

No wonder men desire me! I desire myself!

No wonder men desire me! I desire myself!

“A woman’s vagina is a scary place for a guy to understand,” a Trannychaser named Chris tells me. “But because he has a penis, a guy knows what makes it feel nice. A girl like you has both a penis and breasts, so I’d feel less pressured because I would know what I’m doing.”

Even more experienced guys express this same sentiment — a mixture of fear and loving of the opposite sex — to justify their attraction to shemales, foreign but familiar. “Men fear the inability to bring a woman to orgasm. We can never be sure,” says Mike. “But when a t-girl comes, it’s obvious, even if she’s embarrassed, as some are, of that male part of her body.”

Plus, according to a correspondent named Victor, “T-girls don’t come with all that perplexing emotional baggage of genetic girls that men can never explain. I don’t find beauty in the male form. But, unfortunately, I relate better with males. With a t-girl, subconsciously I’m probably thinking here is a guy who looks like a girl.”

So it’s a guy thing, so much so that so-called tranny-chasers are sometimes defined as latent homosexuals. That’s the conventional wisdom. But it’s not so simple. In my experience, these men are definitely women-lovers, attracted to the feminine, at least a man’s idea of the feminine, while sexually repulsed by masculinity. If latent anything, they’re wannabee t-girls themselves, although I’ve only had a couple of guys actually admit to this uncomfortable self-knowledge.

“Being with a transsexual is not gay, because the transsexual’s femininity provokes the initial attraction. It is not a man’s cock; it is a woman’s cock,” proclaims a self-described “43-year-old married man with two great kids.” Certainly, from my own transsexual point of view, he is the kind of man I find most attractive — legitimizing me as a woman, since he prefers to fuck me rather than the real cunt back home. Indeed, most of the men I “date” — a large enough sample, I’m sure, to be statistically valid — have been married straight guys.

“All men at some point want to suck their own dick, but we can’t, most of us,” laments another married man named John. “As men we have been raised to think sucking dick is gross, and gay. However, when we see a beautiful t-girl in a heavenly woman’s body, it just might be all right to suck that dick. And to fuck that booty or even submit to anal penetration.” Asking his wife to fulfill his fantasy with a strap-on dildo, John says, “would freak her out.”

Fantasy: that’s the recurring key word in the male vocabulary defining their attraction to girls like me. First, we ourselves are phantasmal — deceptive, or illusory, women. As such, we can make any forbidden male fantasy come true. “It’s a fantasy of mine to have done to me what I have done to woman my entire life, consume them sexually,” says Ralph. “Oh, to have a beautiful, full-lipped woman throw me down on the bed and just start ravaging my body, all the while growing inch by inch until it’s proudly sticking out of her panties. It’s a complete surrender, I guess. I never have given a second look to any man, but I would take her dick in my mouth and just go to town. That image I have of being fucked by a woman is enough to get me rock hard.”

Integral to the fantasy is the assumption that shemales must be purely sexual creatures, combining the come-hither desirability of the most brazenly alluring woman with the unquenchable lust of the horniest man. So says Lawrence: “From a very early age, I think it’s fair to say that most men are taught that things like high heels, long painted nails, and porn-star-looking makeup are sexy. I can’t remember the last time I saw a t-girl who was not sporting all three of these little ideals. Why stick with boring everyday women when you can have super-glamorous, fantasy women who actually make a point of putting as much thought into what shoes to wear as the girl next door does into her pension plan?”

Indeed, why else would a transsexual go through such a painful, time-consuming, and expensive transformation, except to attract and please men? After all, we know what men want, because we were once men ourselves! We know that the mere glimpse of a woman putting on lipstick is incredibly sexy. She is advertising herself, making herself ready and receptive. Being a shemale is so self-absorbed and time-consuming, there is time for nothing else except making yourself ready.

That’s the male assumption, and yes, to the extent that male desire validates us as the females we long to be, an assumption grounded in truth. And so we do indeed craft and creatively package ourselves into the supreme sex object, the embodiment of sinful lust, insatiable in our desire to be desired by men. I am desired, therefore I am. With exaggerated femininity and all its fetishistic accruements — big boobs and a finely sculpted ass, not to mention painstakingly applied makeup and suggestive clothes — we advertise that we’re ready and willing and “want it.” Indeed, want it as much as any man.

“That willingness to make an effort, the attention to detail, the openly sexual nature of their look and their attitude,” drools an admirer named Jim. “They embody the ultimate fantasy woman.” Another long-time admirer, Allen, gushes: “Transsexuals attract me because they have declared their femininity and in taking on the ‘weaker sex,’ by implication, their submissiveness. Not that I’m a dom, but I love the fact that they have chosen to be vulnerable, making themselves available to being used by men.”

“Then you have the thrill of everyone thinking you are going out with a really gorgeous girl, but they don’t know she has a penis just like you!” says a long-time shemale fan who identifies himself as Smidsy. Of course, sinful secrets and edgy risk-taking provide a spark to any sexual relationship.

Sometimes I think I’m like one of those life-like, blow-up women dolls that lonely men make love to. As a fantasy, I’m not real. I’m a simulacrum, a virtual woman. (Virtual: one of my transsexual sisters once said, “I wouldn’t have ever existed without the Internet!”) Since I can never be an authentic woman (even with SRS), I become an exaggerated artifice, more feminine and seductively alluring than any real woman can ever be. Shemales are to women as Las Vegas is to Paris or Venice.

But this much is real: I want what every woman wants — not just to be desired, but to be loved. I want romance and flowers. And so my favorite tranny-chaser fan mail comes from Gilbert, who says: “It doesn’t matter what’s between your legs. It’s all about whether you really fall for someone. True love.”

True love for an untrue woman? Maybe, just maybe, Gilbert is on to something. Any student of romantic love knows that the most enduringly passionate love requires obstacles. Think Romeo and Juliet. Think the adulterous affairs on daytime soap opera. And think of that medieval romance of Tristram and Isolde. Since she was already married to King Mark, Tristram laid his sword between their two bodies, his and Isolde’s, as they prepared to sleep together. I am Isolde, and what’s between my legs is Tristram’s sword.

About Joy Saint James

Day job in Big Banking. Elsewhere I'm @ScholarlySlut, whose essays and erotica have appeared in various print anthologies and websites. Email: joy.st.james@hotmail.com.

7 responses to “Shemale Sampler: What Men Like

  1. Hey lovely from a young womanreader maintain the awesome posts

  2. Candice Neadona

    Joy, I’m only a part-time girl, a crossdresser, not a transsexual, but what you say resonates so much with my own feelings, aspirations and experiences! You just proved, if need was, that a pretty head does not mean an empty head! Kisses, Candice

  3. The prominent Confucius said an individual can not
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  4. Jim

    I enjoy your stories very much and have to agree I am sexually attracted to the female form but I am also attracted to thought of sucking and being fucked by a beautiful hard cock. I am also as you state in your story a straight, married guy. I do however disagree with the being scared of pussy/inability to get a woman to climax thing. I have always been very sexual since my mid teens and have been with many, many women. I was the Don Juan of my group of friends and I have to say the majority of women if not all of them always orgasmed, usually 2-3 times. Not bragging but i like foreplay a lot and if you get a woman off with your fingers and/or tongue 1 or 2 times, then she orgasms pretty easily during intercourse. So I think my attraction to shemales in general is just more of it being something new and different aside from the fact some if you ladies are super hot, like you. Any chance your bringing your beautiful self to Las Vegas anytime soon? Had to ask, nothing ventured nothing gained, right?

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