Crossdressers, Trannies, And Famous Tricks

Are you a nervous crossdresser? A fan of trannies? Curious to know if The Old Whore has had any famous tricks? Read on, and all shall be revealed. Up next week: Sharing-the-RentBoys: are you cheating if you hire a friends fav hustler? And bodywork vs. massage: what's the difference?

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I like to cross dress. I like to get fucked in girl's panties and sometimes a bra. Should I tell a hustler that I'll be wearing panties before I hire him? Or just surprise him. I don't want to be laughed at.

Well, I don't know which scenario will be less likely to cause giggles, but rest assured, your hustler will not be surprised. I once made it with a Greek tycoon (ok, he owned a few diners in Queens) who wanted me to rub him down with olive oil and rosewater while he played Connie Francis records and humped a pillow. No shit. A trick wearing panties won't even raise an eyebrow in the pay-2-play world.

If it makes you feel better, you could use the code term "role play" when negotiating with your hustler. Once you say that, he has a warning that all will not be what it appears. 'Role Play' could mean anything from the classic Coach/player scenario to the current vogue for old white guy punked by slim black dudes known as the McCain/Obama. Just make sure you wash your panties. So many CD Johns show up with a briefcase of stinky lace things that they can't wash at home. As long as you're clean, on time and tipping, you'll be fine. Hustlers are known for being tolerant and accepting to those with the money.

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I love trannies! The idea of a chick with a dick is a real turn on for me. But why do so many of these special ladies turn themselves into cartoon versions of porn stars?! Giant fake titties and cheek implants just make them look like Asiatic sex monsters. Where can a guy find a nice, normal, sexy tranny with a fat 8 inches??

Asiatic Sex Monsters! Great band name!

Now what were you saying? Tranny hookers that go too far??? Really? I imagine that anyone who is willing to clip off their wiener isn't too attached to their original cheeks. Maybe you need to alter your shopping habits? The back of a straight porn mag is not the place to discover fresh talent. I suggest finding a soft-faced doughboy with big child-bearing hips and buy him a new lacy outfit. What could be more special than creating your own ladyboy complete with fetish wardrobe of your choice?

Now for those of you that are thinking, "Why doesn't he just hook up those last two guys?" Well, that would be pandering or procuring for the act of solicitation. That would be illegal. As we learned in last week's column, the laws around sex work are varied and fucked up. Many readers felt compelled to school me on the ins-n-outs of hooking. Thanks but I got a guy on retainer for that. But to be clear, I'm an Old Whore, not a practicing attorney. My experiences are presented as info-tainment, at best, and never to be confused with legal advice. That would be like taking diet suggestions from Dr. Phil.

And while I'm throwing myself on my sword -

CORRECTION: Recently, the Old Whore was caught out on the definition of an Alaskan Pipeline. I foolishly thought it was a frozen turd dildo. Nope, or more exactly, not always. A DIY sex-pert reader pointed out that a REAL Alaskan Pipeline is when you milk a dozen or so bull fuckers and collect their spunk in a condom and then freeze it. Later, usually at a group event, the icy phallus is used to grease the holes of the lucky bottoms. And before you doubt him, he sent me a link to a vid that illustrates his theory. Graphically.

Honestly, this seems like a lot of work. This is one of those sex tips for guys who smoke their own turkeys at thanksgiving. I'm lucky if I remember to wear my 'good' cock ring to an orgy not to mention my condom filled with frozen spooge.

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Have you ever had a famous trick? Any blind item you can give us??

Since I was based in NYC during my most active periods, I can honestly say that I've slept with 4 Tony award winners and 8 nominees and yet, no one famous. Really, it's the Tonys. How gay is it to blab about screwing some guy who played the second lead in "Big River"? If I tried to blackmail any of these guys the best I could get would be a few hundred dollars and a "Phantom" tour jacket. But….

In the early nineties, I worked for an agency that was over a 3-star Chinese restaurant known for its Peking Duck. A certain former NYC mayor LOVED his Asian specialties. Twice a week sometimes. I never served him but word was that he was a great tipper and had a mouth like a hoover. The vacuum ,not the president.

My favorite brush with infamy is the ex-husband of a two-time Oscar winner who is so gay that no one will even waste the page space on outing him anymore. Often caught leaving decidedly non-Swank hotels with his big ,black strapping escorts, this d-list actor is spinning down the celebrity drain with guest shots on ER and the various CSI's. My only experience with him took place in DC for a party that required three tops and enough ski equipment to take on Mount Fuji. When I offered the dirt to a tabloid writing friend of mine, he laughed and showed me a 2 inch file, with incriminating pics, on my 'celebrity'. Some guys can't even get arrested in this town.

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Got more questions? Just ask!

Previously: Ask The Old Whore Archive