"I'm gonna tell you a dirty little secret: Philly loves taking it up the ass."

I'm talking to Susan, owner of the Pleasure Chest at 20th and Walnut streets, about women charting one of the last sexual frontiers: the straight man's anus. In her 23 years running the sex boutique, Susan's never fielded so many inquiries from hetero males looking to get ass-banged by their significant ladies. She's even sold a dildo harness to a homeless couple.

Are Philly boys really that ass-tastic? I place an ad on Craigslist to find out: "Kinky Young Woman Seeks Adventurous Man for Strap-On Play." Forty minutes later, it's received 23 replies. Within 24 hours, 119.

Turns out, these anal adventurers are mostly white guys ages 19 to "old" who work desk jobs. About half are spoken for but complain of sexless marriages and uptight girlfriends. Their enthusiasm is startling. "I go to sleep each night with my ass in the air waiting for a kinky girl to take it," writes one businessman.

There's a pervasive belief that only gay men are into anal. I resolve to right this wrong—one glory hole at a time. And who better to start with than the ex-boyfriend?

I pop the question over drinks at Ludwig's Garten: "Would you ever let me fuck you in the ass?"

His face freezes. "Are you serious?"

Well … yeah.

"Get the next round and ask me again in an hour."

Two Framboise flutes and a Kolsch later, Ex and I are browsing starter sets at a 24-hour adult depot. We decide on Tantus' $64.95 Flame, which includes a velvet harness, a 6-inch detachable silicone dildo and a vibrating "love bullet." At home I change into vintage lingerie, light candles and do everything I can to take his mind off the fate of his virgin bum, but there's no delicate way around this. At some point, he's gonna have to assume the position.

I order him onto all fours and squeeze half a bottle of lube down his crack. I've seen enough pornos to know this is my cue to rim him, or at least slip a finger in there, but I can't divorce myself from the fact that this is—like it or not—a shithole. After jabbing his perineum at least 100 times, I slip the dildo in a half-inch and hope he won't notice. He howls. I try to be gentle, speaking softly and telling him we can stop at any time, but he keeps arching his back like a scared Halloween cat. The dildo pulls out of the harness, leaving me no choice but to pump it manually. Ex eventually orgasms, but only after I work his front the old-fashioned way.

When I try to stroke his forehead afterward, his body stiffens. He tells me he feels "violated" and "weirded out." As we lie in silence on opposite sides of the bed, I can't help but feel I've made a terrible mistake.

The next day, I give both Pleasure Chest and my gay boyfriends the play-by-play. "It sounds like you just bought a crappy kit," says Susan, who advises novices to start with slim, tapered dildos, a topical desensitizer and face-to-face positions for greater intimacy. "Or give him the dildo and tell him to lock himself in the bathroom until he gets comfortable with the feeling."

Assholes never lie, and the fact that Ex's was all clenched up meant it wasn't ready. "Wait until his mangina winks at you," advises one gay buddy. "You gotta coax it open before you can dive in."

Adds Susan: "Don't take total responsibility for this failure. It was you guys that made the wrong decisions."

Amazingly enough, Ex agrees. A few days later, he even admits it almost kinda felt good. After the pain stopped.

Questions? Comments? Hungry for Senor Rattler's? E-mail ashlea.halpern@citypaper.net. No phone calls.