Q: I'm a straight guy with conventional tastes in women. But a few years ago I accidentally ended up at a bar with drag queens. I found myself surprisingly turned on by this drag queen in a G-string who came over and shook her tits in my face. Ever since then I've had fantasies about male-to-female transsexuals who still have their male parts.
I really want to find out what it's like to be with a transsexual. How can I meet some? I've heard that they just want to be treated like every other woman, so they try to blend in. I'm not just interested in sex — I'd like to have a real relationship. Any tips on how to meet transsexuals? It seems a bit tricky because I live down South and people are pretty conservative here. —Seeking Tits And Balls
A: Your e-mail arrived, STAB, on the same day that the snail mail brought me a copy of the new book I Am Not Myself These Days (HarperCollins) and a request to allow its author, Josh Kilmer-Purcell, to serve as a guest expert in my column. Kilmer-Purcell's book is a memoir about his first year in New York City, where he was an ad executive by day, a drag queen by night, and shared his apartment with his boyfriend, a crack-addicted BDSM escort. Kilmer-Purcell would, the pitch went, make an excellent guest expert if the subjects of drag, trannies or escorting ever came up. There are no coincidences, STAB, only miracles, so I passed your letter and a few others on to Josh.
His first bit of advice? Stop lumping all the girly boys together.
"There are drag queens, trannies/she-males, and transvestites," Josh says. "Transvestites are generally straight, and use women's clothing as a fetish. Trannies are generally as demure as she-males are exotic, but under both their wigs they've got some of the same 'trapped in the wrong body' feelings. Drag queens are like rental birthday clowns at gay parties. We're not women trapped in male bodies. We're celebrities trapped in normal people's bodies."
And what's a guy who seeks a lady with tits and balls?
"He's a tranny chaser," says Josh. "And where do tranny chasers find hot, horny trannies to hook up with? Online. Try Craigslist, Casual Encounters, search M4T. Where do you find hot, horny trannies that you can bring home to your mother in the Deep South? You don't. The sequined, G-stringed vixen that shook her tits in your face at the club is usually not the marryin' kind. They don't try to blend in. The ones who do try to blend in don't have double-D tits. Which means the reality is probably not gonna live up to your fantasy."
Q: I am happily married to a great woman. For a couple of years I have had fantasies about fucking or being fucked by a she-male (and occasionally, these fantasies have been augmented by including my wife in the equation). I never fantasize about men, and the gay porn I've seen does nothing for me. Does fantasizing about she-males make me gay? Also, I've never shared this fantasy with my wife. She has the ability to be GGG, but I worry that if I ever bring this fantasy up, it might be a complete turnoff. Is there a delicate way to probe the waters with her? And are there a lot of guys out there like me? —Titillated By Nutted Nymph
A: "When I first moved to New York City, there were about six ads for tranny hookers in the back pages of the Village Voice," says Josh. "Now there are six pages of them. I never believed in sexual fads, but I'm quickly being converted. So, yes, if numbers console you, TBNN, there are a lot of guys out there like you."
Before we get to the wife, a word about whether a thing for she-males makes you gay: "Yes, it does," says Josh, "because all gay men secretly desire to titty fuck, and are consistently frustrated that there are not more butch men out there with huge tits and collagen lips." (Mr. Kilmer-Purcell is being sarcastic, TBNN. Gay men are not, as a general rule, attracted to she-males. A taste for she-male cock — sometimes called, distressingly enough, "stick pussy" — is pretty much exclusive to straight-identified males.)
On to the wife: "Getting your wife to play along might not be as hard as you think," says Josh. "Has she ever watched a little lezzie porn with you? Has she indulged your ass needs from time to time? Seems to me that a she-male might be a good middle ground. If she knows you like getting your ass pegged and she has no aversion to the occasional foreign set of tits in your bed, bring up a threesome and leaf through the sex ads with her. When you come to the tranny section, just act surprised as you point out the benefits for you both."
Or not.
To get to your wife signing off on a three-way with a she-male, Josh presumes your wife watches lezzie porn, pegs your ass, and has "no aversion" to another set of tits in your bed — or to prostitution. Those four assumptions taken together rank up there with "welcomed as liberators." Nevertheless, Josh's last bit of advice — innocently flipping through the she-male ads together — would be a good way to predict your wife's reaction to your fantasy. Best of luck with that, TBNN.
Q: I'm a 40-year-old white male who has been with over 100 women. Now I am obsessed with she-males. In the past year, I've met a couple of she-males. They were both hookers, of course, but I made out with both of them and got a blow job from one without having to pay. But I didn't get to the part I wanted: giving them the big ram right up the anus. Am I obsessed with anal sex? Or is my problem that I have some dark desire to break my self-imposed "one penis" rule? —Loving The T-Girls In Minneapolis
A: "Good God," says Josh, "just pay the nice ladies. It doesn't matter whether you're obsessed with anal sex or multiple penises. You're obsessed with fucking she-males, and they're obsessed with paying the rent."
Both Josh and I were less than impressed by your chiseling ways. "Trying to get free goods from a hooker is not terribly chivalrous," says Josh. "We all go to our different jobs every day, and we all expect to get paid. If you 'really, really' want to fuck she-males, and the ones you're meeting are prostitutes, then do the polite thing and make everyone happy."
You can read more about Josh Kilmer-Purcell's new book by going to iamnotmyselfthesedays.com.
Q: Your advice for Just Another Silly Girl last week was great, but I think you missed an important factor. She was having sex with a boy who wasn't being particularly nice to her. They can use each other till they get good and sore, but she does need him to stop being an asshole about it. Here's what I'd recommend she say to him: "You like to fuck me, I like to fuck you too; we have fun, I'd like to continue having fun. But if you ever insult me again, I will tell everyone you know that I'm using you for sex. I like the kicks I get with you, but I'm no longer willing to trade my self-esteem for them." —Concerned Stoner
A: Well said, CS, well said.
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