When I was sixteen my mom confessed to me that she had a vibrator, which a friend had given to her, but which she never used. She just liked to keep it around "for laughs."
     Within a day I found the vibrator and immediately plunged it into my own ass while in a fit of vigorous masturbation. I could spend the rest of my life in analysis and never get to the bottom of that one. In fact, I don't even know why I felt the need to stimulate my prostate (I wasn't even aware I had one), unless on some level my ass knew that such an act of appropriating your mother's sex toys is the modern equivalent of killing your father.
     Eventually, though, the vibrator vanished. I don't know if my mom pressed her ear to the bathroom door one night only to hear a familiar whir, or if my constant treatments of bleach (hey, sanitation first) to the vibe's surface irritated her in some fashion that she couldn't fathom and she tossed it. Either way, such a loss lead me to desperate measures, involving cucumbers, a broom handle, a fire poker (just the handle) and, in an incident I refer to simply as "The Chiquita Affair," a banana that broke off inside me. I nearly killed myself straining to get that out as quickly as possible, and let me tell you: there's nothing more fucked up than shitting a banana.
     However, this was just my ass. I couldn't get over the fact that I was potentially a freak, and possibly violating some serious biblical code. I mean, Jews can't eat pork — surely anal delights are way higher up on the list. When I walked by people in my small town, I tried to imagine them pillaging their rectums with a variety of implements (usually garden tools), and I just couldn't do it. And somehow, when they looked back at me, I felt they knew an ice cream scooper had once protruded from my posterior. (Oh, and sickness of sicknesses, that same ice cream scooper is still nestled in one of the drawers in my parents' kitchen! I know it's been many years and numerous rinse cycles, but on those hot August afternoons when my dad suggests a chocolate sundae, I politely decline.)
     This pleasure center I discovered in myself only fueled my obsession in wondering about the way other people's asses operated. I mean, for years I never came across a woman who admitted to liking (let alone having) anal sex. I read interviews with porn stars who said they reserved anal sex for their off-camera sex life, leading me to believe that fucking a girl in the ass was the Rosetta Stone of sex, performed only by women who had conditioned their sphincters in a Kegeling exercise that allowed them to siphon the jizz out of man in such a tantric fashion that would regress the lucky fellow to a womb-like state.
     Because the frequency with which I got laid between sixteen and twenty-five could be measured by the appearance of comets, and because those women I did manage to bed with any regularity just seemed so loaded with vitamin D and other wholesome goodness, I never found myself in a situation where I felt comfortable saying to a girl, "So, would you mind if I fucked you in the ass tonight?"
     And that lasted until I met Whitney.
     Whitney was the roommate of one of my ex-girlfriends, which was a disaster waiting to happen anyway. We were lying in bed in post-coital bliss, when I mustered the courage to ask her if she wanted to try anal sex.
     "Sure."
     The speed with which I was able to achieve another erection was dizzying. I grabbed a bottle of lotion from beside her bed and started "lubing her up." I was generous with the lotion; I wanted things to go as smoothly as possible.
     She moaned softly as I slid my finger in her ass, then two, and I thought that things had been loosened up enough. She slid a pillow under her belly and spread her legs as I got in between them, rubbing the head of my cock up and down the crack of her ass and then sliding it in. I felt more pure joy than when I graduated high school.
     Then the head of my dick hit something. In my experiments with driving a dildo up my own orifice, this didn't seem right. I mean, maybe my ass was special, but I could sink my mother's vibrator pretty far in there.
     I pulled out a little, then pushed in again. Whitney was moaning like a real champion. Things couldn't be going better.
     Except that my dick hit something again. The gravity of the situation dawned on me: the tip of my dick was in direct contact with — something. (I have since come to know this unfortunate circumstance as "running over a turtle.")
     I immediately withdrew and leapt off the bed.
     "I have to go to the bathroom," I said, and blazed a trail to the shower, haunted by thoughts of hepatitis, bacterial infections, gangrene. I didn't even wait for the water to get warm. I jumped in the shower and held my dick (which had shrunk considerably) under one of the streams of water, and then held the peehole open so it could be thoroughly rinsed.
     I jumped back out of the shower, found some Q-Tips, got back in and lathered one of the Q-Tips with soap and jammed it into my dick. For three days I couldn't pee without tears welling in my eyes.
     Mid–urethra swab, Whitney pulled back the shower curtain.
     "What kind of a fucking freak are you?"
     Had it not been for the fact that a Q-Tip was dangling from the end of my dick, I might have had an answer for that. Instead, I said, "What are you doing in here?"
     "I've got to take a shit."
     I closed the shower curtain and put my head under the water, trying desperately hard not to listen as she shamelessly used the facilities a mere three feet away.
     While I stood there, praying that my fecal encounter wouldn't lead to a hospital visit, I could swear I heard something like a grunt. I had lived my whole life in denial of the fact that women even had the capability of farting; reality as I understood it was crumbling.
     It occurred to me that Whitney and I probably weren't going to work out.