DILFs, Trunk Butt, And Carol Channing

What do a DILF, a case of trunk butt and Carol Channing all have in common? This edition of Ask The Old Whore.

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I'm a forty-something gay man who is often mistaken for a hunky 30-something. I have always held a good job, but with the market tanking, my 401K is pretty much wiped out. I'm thinking of trying my hand in the porn business. Just for some extra change and maybe a few kicks. Any suggestions?

Damn you Bernard Madoff! Will we now have to suffer an explosion of hedge fund manager porn due to your greed?! I can just see the pervy titles now: The Day the DILF Made Porn, 30RockHard, or worse, an all-nude remake of Frost/Nixon. I shiver at the thought. But as for you Mr. DaddyCakes, so you want to make porn? Great. But don't count on established producers seeing your potential. If you were smart, you would invest in some cameras, an editing program and hire a cute Internet wunderkind to help you create a website and market yourself out the wazoo. With Xtube, porntube, and a fistful of other 'amateur' sites, the time is right for a homegrown porno explosion. And so what if the idea of a 45 yr old middle-management type in black socks and a cock ring makes me puke in my mouth a bit, somebody out there is sure to pay 9.99 a month to watch it.

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I love everything about musical theatre. I live, eat and breathe Broadway. I'm heading to NYC in the spring to see if I can get my career started. I'm a triple threat, an actor who can sing and dance. But to get to NYC, I'll need money. I have a chance at making some j/o porn here in San Diego. Nothing too hardcore, just wanking with a bud. Do you think it will hurt my chances at a Tony?

Broadway legend Carol Channing once told me that the road to Broadway is slick with sweat and spunk, or something like that. Her dentures were loose and I was fucked up on X. The point is, no, a jerk off vid shouldn't hinder your chances of success on the great white way. You may never get a chance to star alongside Zac Efron in some grotesque Disney abortion, but a J/O video won't hurt you with the casting directors of any reputable Broadway show. Hell, think of it as an audition tape. Tell your porn director that when you come you spontaneously break into a number from Hairspray. If you're jackin buddy is an aspiring thespian too, you guys can break new porn ground by jacking off while doing the bedroom scene from Death of a Salesman. I always assumed Biff was waxing the monkey in that scene anyway.

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I know you're a whore and not a doctor, but before I seek the advice of my MD, let me ask: What do you know about a prolapsed anus?

Oh, someone's got trunk butt. For those readers without a degree in anatomy or advanced hooking skills, a prolapsed anus is when part of the rectum pops through your ass like a big pink turd that won't dive into the pool. This isn't so painful, but it is awkward in 'social' situations. I always called it trunk butt since it makes your asshole look like it has a baby elephant trying to wiggle its way out. This can happen from too much straining during bowel movements but baby, who are you kidding? Someone got too many weed wackers working in his rose garden? Maybe you got a little ambitious with your Ben Andrews dildo? Tsk tsk, This Old Whore isn't here to judge, just snicker and dispense advice. As gross as it sounds, this is an easy fix. Really nothing more than when you got your neck done. Any plastic surgeon can remove the 'redundant' colon and stuff the rest back into your fuck chute. If you are already experiencing fecal incontinence (are you shitting yourself?) they can also do a sphincter tightening while they're in the area. When it's all over, you'll feel like showing it off all over town, but then again, that's what probably got you into this trouble in the first place.

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In the last TOW posting, I replied to a letter regarding a FTM top that crossed the line. Not the line of good taste, which really doesn't exist in my world, but the line between humor and being unnecessarily offensive. While I love commenting on the very explicit sexual perversions, fetishes, kinks, and down-right twisted shit our sexually liberated community engages in, it can be difficult to edit myself responsibly. I would never want to make any of our readers feel maligned or singled out for ridicule. I offer my sincerest apologies to anyone who was offended.

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Previously: Ask The Old Whore Archive