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How to be a skank without breaking hearts



I am a 22-year-old woman, generally happy, but I have a problem with cheating. My peers seem to have no problems staying faithful, but I do. I have never been faithful to anyone, and I have had many relationships with men and women. Some found out, some didn't. I have finally found someone I feel like I can spend the rest of my life with, I am happy with him on every level, but I still cheat. I have been told this could be sociopathic, but I'm not sure. I have always really loved sex, all kinds, and have done everything short of urine/feces or anything illegal. I don't have any guilt, but I don't want my boyfriend to find out and leave me, or worse, stay with me as I continue to break his heart through constant cheating. Would therapy help? I hope you have some advice. I just wish I could stop.

She Kraves Acrobatic Nookie Konstantly

Why stop, SKANK?

You say it's not the skanking around that's making you unhappy -- you enjoy the sex, you enjoy multiple partners, you enjoy everything short of urine/feces/criminal. If you're telling the truth -- if you're not glossing over some deep-seated pain -- the sex isn't the problem. What's troubling you is the deceit. You're worried that this boy, like the boys and girls before him, will be hurt when he finds out you're a lying, cheating skank.

But you can be a skank -- and I'm using the term in the sex-positive sense -- without lying or cheating. Have you tried being honest with potential boyfriends and girlfriends about your tastes and track record? Where there are no lies of commission or omission, SKANK, there's no deceit. And where there's no deceit, there are no boys whose hearts are broken when they find out they are being cheated on. Let prospective partners know who you are and what you're about before things get serious, SKANK, and your problem will be solved -- i.e., boys and girls who want monogamy won't get involved with you. You'll encounter some rejection, sure, but if you keep the honesty thing up, sooner or later you'll find a partner who doesn't mind/thoroughly enjoys being cheated on. Ta-da, everybody wins.

Now, my advice would conclude with the previous paragraph if it weren't for the last line of your letter: "I just wish I could stop." If that's how you truly feel, SKANK, then perhaps there is something pathological about your behavior. And here's a little more evidence that your sexual adventures may not be coming from a particularly healthy place: Someone like you, SKANK, surely knows that there are men and women out there -- wannabe swingers, the polyamorous, the growing legions of cuckold fetishists -- that would kill to be with a woman like you. The fact that you haven't sought out any of these people and have instead dated and deceived the monogamously inclined is revealing. And what it reveals isn't pretty: If you've avoided the swingers, the polyamorous, and the cuckold fetishists, SKANK, and sought out only guys and girls that will be hurt by your actions, then you're not skanking around because you enjoy it. You're doing it to wound and drive off people who attempt to get close to you. And that's something you should definitely hash out with a shrink.

My boyfriend and I met nearly three years ago when I was a call girl and he was a guy who wanted to be pegged (a big, big part of my business). We became friends, then partners, and now we've been together for three years. We share a home and we're bringing up my 7-year-old son together. It's the best relationship I've ever been in -- he's loving, communicative, patient, supportive, and WAY fun sexually. His dad told me recently that he's never seen his son so happy. He's got a good job, and in addition to being a stay-at-home mom, I occasionally see my old regulars. In fact, we've done a few calls together, for trusted clients who wanted to experience a threesome.

My question is, how common is it for prostitutes and clients to end up together? Of course the business is full of pitfalls, and is not for the timid or directionless, but human beings in proximity do tend to fall in love given the chance ... or are we just an anomaly?

Lucky In Love

Sex workers and clients do occasionally fall in love (check out the wonderful memoir Concertina by Susan Winemaker), so it does happen, LIL. But it happens so rarely that I was reluctant to print your letter, as it will give countless johns false hope. But I'm sleep deprived, so here it is. Congrats on finding the love of (fingers crossed) your life, LIL.

I was recently seeing an alpha-male type -- Ivy League grad, big executive, loud laugh, etc. He found me on a Web site, one thing led to another, and he was showing me pictures of him in his ex-girlfriend's panties!

We went out for the first of many coffee dates and it ended with me putting my hand down the back of his pants and feeling a silky thong! We made plans to meet for some actual dress up. Girly Boy stood me up! A couple of times! I got annoyed, but I put up with it because his apologetic e-mails were so abject -- and filled with new dirty pictures. We eventually planned a whole Sunday afternoon of him cleaning my house, me putting makeup on him, and a grand finale of him eating me out on the couch. And he stood me up again!

I come to my point now: I gave him my FAVORITE black thong and push-up bra at our last coffee date. He then supplied me with a hot selection of pics that got me very excited for Sunday fun. But Sunday fun never happened! He didn't even call! All I want now are my panties and bra back! I told him to mail them to me and he HASN'T. This is my favorite set of underwear! I KNOW he's parading around in them and thinking, "I won!" Typical alpha male! How do I get my panties back?

Lost My Favorite Panties

By threatening to create a YouTube slideshow using the pics Alpha Male already sent you, LMFP, or by threatening to e-mail the pics to [email protected]. Or, hell, go with a retro, low-tech threat and tell him you're going to print up fliers and drop them over Nazi-occupied Europe. Not that you should do any of those things, LMFP, but his willingness to mess with your head -- all those twat-teasing e-mails, all those flirty coffee meetings, all those dates for play that he broke -- gives you carte blanche to mess with his head.

Finally, LMFP, alpha males in lacy panties don't do anything for me personally -- seriously! -- but your letter aroused my professional curiosity. Panty thieves had been in the news last year; a few were busted and chucked into the cable-news meat grinder. These guys tend to be dweeby in the extreme, i.e., the kind of men who can only collect women's panties by stealing them. I would like to lay eyes on the pics of a panty collector alluring enough to seduce multiple women -- I guarantee that you're not the first -- into parting with their favorite panties and bras. I promise not to drop his pics over Nazi-occupied Europe.

YouTube however ...

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