.A Fin-Tastic Fetish

Snorkel kink, cross-dressing woes, and a straight dude wonders about his trannie blowjob.

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. There is a small subculture devoted to scuba fetishism
on the Internet, but it’s a total sausage/snorkel fest. 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 Live Wire 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, FFF. 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 male who identifies as a
cross-dresser. I enjoy it, and I’m okay 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 I work through this with my ex so we can get
back together?

Bashfully Oblivious Ovary Buster

Either your ex was honestly threatened by your cross-dressing, BOOB,
or she’s doing what a lot of us do when a seemingly decent relationship
comes to shit for no good reason: She’s looking for an explanation, and
your cross-dressing is the low-hanging fruit. Blaming the
cross-dressing 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 help her work through this? Probably not, BOOB, particularly
if she was actually feeling “femasculated.” You could agree to stop
cross-dressing, 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 cross-dressing was just a rationalization, BOOB, then there’s
nothing to solve here, no way of working through this. Find a new
girlfriend.

I’m a 24-year-old guy, and I just got a blowjob 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 (as well as
regular guys-doing-it-with-girls 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 shemale escort shores up your
heterosexual bona fides. Gay guys don’t frequent and/or fellate shemale
escorts (on purpose or by accident); getting with shemales is an
entirely straight-male pursuit. So you can go right on identifying as
straight, RAGE. Of course you aren’t totally straight — try
thinking of yourself as something more than straight, not less —
but you’re close enough that you can round yourself down to straight
with a clear conscience. (Offer void the day you start blowing hemale
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, RAGE, 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 — honestly 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, RAGE, good on you and your escort for using condoms. But
there is 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.

While your response for To Rape Or Not To Rape is great advice to
keep a horny guy out of a legal jam, you failed to consider whether the
woman TRONTR is corresponding with is an actual consenting person. Just
because TRONTR has couple of IMs, a photo, and e-mail consent to rape
one [email protected]
doesn’t mean he’s actually corresponding with a person who shares his
fantasy. He could be corresponding with a person impersonating Jane
Doe. I have friends who’ve had personal ads placed online with their
names, photos, and addresses imploring someone to abduct and rape them.
The situation reeks of a setup, and your advice is
irresponsible.

Poster Bitch

TRONTR indicated in his letter that he wouldn’t do anything with
this person until he met her in person for drinks and verified her
identity and interests. I encouraged him to get it in writing in
addition to getting a verbal and visual confirmation, not in place of
either. There are people out there maliciously posting personal ads;
there are also people out there sincerely interested in rape and
abduction role-play scenes. Anyone thinking about realizing a fantasy
as extreme and edgy as abduction/rape role-play needs to get it in
writing and from the lips of the person or persons with whom he or she
intends to play.

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