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Boy Does World (Excerpt) I

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I realized over cocktails one night that my life had undergone a radical change of heretofore unknown proportions: I no longer joke about dildos. I have actual, serious discussions with friends about dildos, butt plugs, and various other anal-insertive devices.

Boy Does World
Boy Does World

For some reason, at an earlier age, I had thought of dildos as the last refuge of the undesirable, the one who couldn’t get laid. Of course, I also thought I would look eighteen forever. Now, older and somewhat wiser, I know there are a plethora of uses for surrogate penises beyond the above.

Nothing particularly earth-shattering in all this, except for one thing: I had never bought a dildo.

On the basis of this realization (plus the fact that I found myself on a Saturday night without anything or anyone better to do), I resolved to buy a new friend, of the rubber sort. I didn’t have any particular set of criteria in mind. Just something vaguely humanoid with no inflatable body attached.

I chose what I considered to be a reputable dealer and made the trek to Dupont Circle. The first thing to strike me on entering the store was the lack of other customers. This went against my assumption that the place would be swarming with guys picking up those last-minute items to make the evening just right.

I asked the guy behind the counter if things were usually a little busier on a Saturday night. ”I think there’s a big party tonight,” he said. Socially humbled, I said no more and meekly moved to the back.

Not much to choose from back there, but having recently come off a two-and-a-half year hiatus from bottoming, I was somewhat unsure of my limits—though the double-headed number that looked to be as big as a bodybuilder’s thigh seemed to be outside them.

I started with the butt plugs, of which there were three sizes: ballpoint pen, Mt. McKinley, and ”just right.” It seemed like a good idea to get something that would stay put and do its job with little help. However, for the purposes of self-amusement, I didn’t see how putting something shaped like an elf’s hat up my butt would help much in the fantasy department.

I wanted your average, everyday, flexible, lifelike, all-American dildo with testicles for a base, which left me with two choices: big and incredibly big. Not being a complete size queen (and not wanting to test my limits that quickly), I settled for merely big.

It’s too bad dildo shopping can’t be more like car shopping. How hard would it be to have a few floor models on display so you can take a little spin and see how it handles? Granted, the dressing rooms would be interesting, and some people may have hygiene concerns. But placing some condoms around would solve that problem and send a safer sex message to boot.

I finally found one that seemed suitably lifelike and within the realm of physical capacity. While gently squeezing it to test the resilience, I had a brief, yet terrifying, vision of Mr. Whipple brandishing a riding crop. I shook the thought, took the package of pleasure from its hook, and proceeded to the register.

After paying the guy behind the counter and deciding not to ask where the party might be, I walked home with my new friend tucked discreetly in a paper bag. On the way, half of me chattered that everyone on the street had X-ray vision and thought what a loser I was on a Saturday night. The other half wanted to rip the machine-made manhood free from its bag and wave it playfully in the faces of passers-by. Thoughts like these keep my therapist in business.

I finally made it home without screaming my sexual proclivities to the world (that night at least). My new friend has found a good home on the closet shelf. I’m not going into further details, as some parts of my life remain private. Besides, I need something to talk about over cocktails.

Excerpted from Boy Does World. Copyright 2010 Sean Bugg. Used with permission.

Boy Does World: Fifteen Years of Bad Behaviors, Bad Attitudes, and Happy Endings by Sean Bugg is available at select bookstore and online at

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Sean Bugg is Editor Emeritus for Metro Weekly.