The two things that I dig most on a woman are a nice big pair of … swim fins. Some of my earliest sexual fantasies revolve around Jacqueline Bisset in The Deep. It's frustrating to have such a bizarre fetish. One day I'm heading somewhere tropical like Hawaii, where I hope to meet scuba divas. Until then, what do you suggest? Give up my fetish and embrace vanilla? Or redouble my efforts to find one of the maybe half-dozen women in the world into this?
Fin Fun Fan
It's amazing how the sight of something as innocuous-yet-titillating as the poster for The Deep can, if a young man lays eyes on it at just the right moment, endow that boy with a lifelong love-life-complicating fetish. I ponder this phenomenon every time I see that ad for Old Spice's new body wash featuring an impossibly hot centaur soaping up in the shower. (While you regard your fetish as a burden, FFF, at least you can find scuba gear. Where are all the fetishists being created by Old Spice supposed to find centaurs?)
The odds that you will one day meet one of the very few women out there who share your fetish are slim. But let's say you manage to track one down. What are the odds that you'll be attracted to her physically? And emotionally? Slim and slimmer. Your best bet is to date women you find attractive, demonstrate that you're a decent and loving guy who can enjoy vanilla sex, and then roll out your fetish.
Some would argue that withholding info about your fetish is dishonest. I would argue, however, that "withholding" info about a harmless fetish — FFF just wants to play dress-up, he's not into shit or shunts or shin splints — demonstrates a certain degree of emotional intelligence. Waiting until about three months in says to prospective scuba babes, "Hey, I wanted you to get to know me before I told you this, because I realize that it might strike you as odd. And while I'm kinky, I'm not obtuse or insensitive."
I am a straight 22-year-old man who identifies as a crossdresser. I enjoy it, and I'm OK with myself. But my ex-girlfriend revealed to me that it made her feel like less of a woman and that I was doing the female version of emasculation to her. (Ask.com says the word is "femasculation.") How can we work through this so we can get back together?
Bashfully Oblivious Ovary Buster
Either your ex was honestly threatened by your crossdressing, BOOB, or she's doing what a lot of us do when a seemingly decent relationship goes to shit for no good reason: She's looking for an explanation, and your crossdressing is the low-hanging fruit. Blaming the crossdressing allows her to rationalize the breakup in a way that leaves you both blameless, i.e., the relationship was done in by your panties and not by something that she did or by something that you had any real control over.
Can you work through this? Probably not, particularly if she's truly feeling "femasculated." You could agree to stop, but you'll only wind up doing it on the sly; you'll get caught in panties and end up dumped all over again. And if pointing to your crossdressing was just a rationalization, then there's no way of working through this. Find a new girlfriend.
I'm a 24-year-old guy, and I just got a blow job from (and gave a half-assed one to) a transsexual male-to-female prostitute. It was no accident: I'd spent about two years looking at TS porn, and the whole thing seemed like a hot idea. But the plastic-surgery scars around her tits and her cock in my mouth kind of made me nauseated. I went through the motions only because I didn't have the guts to walk out. (We both had condoms on.)
I'm not sure if I can face my girlfriend of a year. I've been faithful to her until now, and I feel like crying. I don't know if it's because it was illegal (prostitution), because I was cheating on her (unfaithful) or because I can't say I'm totally straight anymore (cock in my mouth). I don't know how to tell my girlfriend. She knows I look at porn, but she doesn't know I look at TS porn — no one does.
Regrets About Gay Experience
Paradoxically, RAGE, going down on a she-male escort shores up your heterosexual bona fides. Gay guys don't frequent and/or fellate she-male escorts; getting with she-males is an entirely straight-male pursuit. So you can go right on identifying as straight. (Offer void the day you start blowing he-male escorts.)
As for the rest of your angst: If you're serious about this woman, then cheating on her like this was a shitty thing to do. But you're not married yet, and now's the time to get out there and satisfy any outstanding sexual curiosities — before marriage and before kids. And while unburdening yourself to the girlfriend may sound like the noble thing to do — honesty being the best policy and all — each of us gets to take at least one big secret to the grave. If this truly was a one-time, lesson-learned, never-again experience, let it be the secret you're buried with.
Finally, good on you and your escort for using condoms. But there are a whole host of sexually transmitted infections you could've picked up from her, condom or no condom. Make whatever excuse you need to in order to get out of having sex with the girlfriend, go get a full STI screening, and refrain from having sex until you get the all-clear from your doctor.
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