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Originally published September 16, 2010.

I'm sorry about sending this letter to you via snail mail. I don't want to send an e-mail because I'd rather not have a record of this living forever on some server somewhere. About six months ago, after watching my girlfriend insert a tampon, I asked if I could do it for her next time. She thought it was an odd request but agreed. After "helping" a few times, the conversation turned to what it felt like to wear one. Her response was, "Want to try one yourself?" With her help—and a little lube—soon there was a string hanging out of my butt. This has now become a regular feature of our sex life. And I have started doing this when I masturbate alone. I went out and got my own box of tampons—Tampax Pearl Plastic Regular are the best (they're the easiest to insert)—which I keep hidden. I have a few questions:

1. Why do I get such a euphoric feeling when I pull the tampon out when I'm coming? Does it have something to do with my prostate?

2. Am I doing any damage to myself?

3. Just how deviant is this practice?

The Ass Man's Peculiar Anal Xccentricity

1. The tampon in your ass swells as it absorbs lube and rectal mucus and whatever else, TAMPAX, and stimulates—yes, indeed—your prostate as it swells. Yanking the tampon out when you're coming further stimulates your prostate at the exact moment it's being zapped by orgasmic contractions—contractions that involve your anal sphincter, which you're also stimulating as you yank. A butt plug would provide you with the exact same sensations—well, the exact same physical sensations. Part of the tampon-related thrill for you, I suspect, is the gender-transgression aspect of this. You're not just penetrating yourself, TAMPAX, you're penetrating yourself with an absorbent feminine talisman. Not all men who enjoy anal penetration are interested in being symbolically feminized—ahem—but clearly you are, TAMPAX.

2. My hunch: As long as you're using lube and not leaving 'em in for days at a time, you should be fine. And a medical expert I consulted—who wished to remain anonymous (he didn't want his name linked forever to anal tampon play on some server somewhere, either)—backed me up. "This would pose zero risk," says my medical expert. "Medically, there's nothing else to say about it."

3. When it comes to human sexuality, TAMPAX, deviation from imaginary and tyrannical "norms" is the norm.


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