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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 demur 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.”
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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 woman.
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.iamnotmy
selfthesedays.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.
mail@savagelove.net
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