Now it’s tme for some perverted emails.

‘Am I obsessed with anal sex?’

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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 that 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

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 (Harper Collins) 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.”

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

“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.

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 blowjob 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

“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 www.iamnotmyselfthesedays.com.

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

Well said, CS, well said.

I am a 17-year-old straight girl with a boy problem—and as such I am fairly sure it won’t be terribly interesting to read, and will thus avoid publication, but I figured it would be worth a try.

I’ve known this boy for three years. A year ago, he asked me out but wanted me to keep the whole thing secret. We had the prototypical movie-theater-back-row kissing extravaganzas. Alas, we eventually split. I spent months crying and sulking, openly loathing the prick. Eventually I gave up hating him, and soon after we “hooked up,” as the youths call it these days.

During a fateful conversation shortly thereafter, he informed me that I was no more than an easy, alcoholic “no big deal.” This resulted in yet another period of sulking and crying. I confronted him. Soon we were at it again, and I was feeling sluttish about my inability to have a platonic relationship with a straight boy. His response: “Just because two people have amazing sex doesn’t mean they’re not real friends.” Since that conversation, we’ve gotten together a few times, but never as friends. I never thought of myself as someone shallow enough to go through all this just because he’s good in bed—Christ, is he!—but I suppose that’s really beside the point. Anyway, my questions:

1. Is it actually possible for two people to have both friendship and sex?

2. Will anything more come from this? Is there any chance at an actual relationship? …. Just Another Silly Girl

1. Yes, absolutely—and I speak from experience. (Hey there, Mike.)

2. Nothing will come of this, JASG. Sorry.

Let me clue you and other youths in on something that ought to be covered in sex ed but isn’t (nothing useful ever is): some people seek out sex partners for whom they feel nothing or, worse yet, for whom they feel nothing but contempt. Why? Because some people are insecure assholes, JASG. Since it’s impossible to have sex with someone without making yourself vulnerable, and since the more attracted you are to someone the more vulnerable you have to make yourself, insecure assholes will sleep with people they don’t care about. Being rejected by someone you actually like and/or being exposed as a bumbling beginner is scary, so insecure assholes avoid the emotional risk by seeking out, say, an easily manipulated person with low self-esteem.

The mistake you’ve made, JASG, is assuming that this guy must like you because he wants to fuck you. While that’s often the case, it’s not always the case, and this boy’s desire to keep your relationship secret was a red flag. Now that you know he’s been using you, JASG, you have a choice to make. You can go back to loathing the prick, and that’s probably what most people would advise you to do. But if you’re digging the amazing sex, and you can accept that nothing more will ever come of this relationship, hey, why not use him right back?

I’m a first-year student at a university in Canada. Everybody is quite accepting of homosexuals like myself, so I don’t have to deal with people calling me names and things like that. However, discrimination is the least of my worries. My roommate, let’s call him Stephen, has homosexual tendencies too, though I’m having doubts that he is completely gay like me. Growing up in a rather conservative city in the U.S., it was great for me to become close to a rather free-spirited Canadian. Though tall and confident, he is still in the closet about these tendencies (the only person who knows about them is me), so the rest of the people who live near us only know me to be gay.

At the beginning of the year it was great. We would change in front of each other, have great conversations, and once we even had an inadvertent fling. But recently, things aren’t carrying on in the same uninhibited way they used to. Lately he comes home drunk from partying with straight guys and then crawls into my bed and has sex with me. The sex doesn’t resemble the fling that happened earlier in the year—there is no sweet talk, no personal connection. I don’t have the heart to make him stop once he’s started, and afterward he just goes into his bed and passes out. It’s hard to know how to deal with this.

There isn’t anyone I can talk about this with. I feel like it was fate that the two of us were assigned as roommates, but on the other hand, he causes me a lot of unhappiness. Should I confront him about the situation? I could tell him outright that he’s hurting me, but that might lead to awkwardness between us. …. Sometimes Misery Doesn’t Love Company

You’re also being used, SMDLC. Your drunken roommate isn’t ready to come out as gay or bi, and so long as you’re willing to be his private come dump, he doesn’t have to. With you around he can play it straight, get drunk with his pals, and have all the gay sex he wants after each inhibition-lowering binge. And while your predicament may sound desperately hot to others—I’m gonna get lots of mail from guys offering to trade places with you for a night—for you the hotness has worn off because you’ve been out long enough, and you’re emotionally healthy enough, to want something more from a guy than just his loads.

So what do you do? Assert yourself. You have more power in your situation than JASG has in hers, SMDLC. While it would be relatively easy for JASG’s boy to go find himself another girl, your roommate can’t find another guy without taking some baby steps out of the closet. So make up your mind about what you really want, SMDLC, and what you’re willing to settle for, and then confront your roommate. I doubt he’s ready for a relationship, but at the very least you should be able to leverage a little more compassion, tenderness and sweet talk out of him.

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