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Hey Woody,

How’s it going? I read your column all the time and I get such a kick out of your responses. I want you to know that I always defend you. I always tell my friends “He’s not a heartless bitch, he’s a cranky bastard. There’s a difference.” Anyway, I have a question. Can you explain the safe/proper way to use butt plugs (other than sticking it up your butt?). Do you use it just before sex or are you supposed to leave it in you for a few hours? If so, is that safe and does your butt become loosey goosey afterwards?

– Anal Retentive

Hey Woody,

How’s it going? I read your column all the time and I get such a kick out of your responses. I want you to know that I always defend you. I always tell my friends “He’s not a heartless bitch, he’s a cranky bastard. There’s a difference.” Anyway, I have a question. Can you explain the safe/proper way to use butt plugs (other than sticking it up your butt?). Do you use it just before sex or are you supposed to leave it in you for a few hours? If so, is that safe and does your butt become loosey goosey afterwards?

– Anal Retentive

Dear Anal,

You call me a bastard and then ask for mercy? Christ, you sound like my dad right before I shot him.

And what was that crap about “other than sticking it up your butt?” Where else would you stick a butt plug—in your ears?

Butt plugs are toys so there aren’t any “rules.” What feels right for you may not feel right for someone else. There’s two reasons to use them: Because they stimulate the anal opening (science for “it feels good!”) or as a sort of training device to get your sphincter muscles ready to take on larger cargo.

Remember, the sphincter has two muscle rings. The first is voluntary (you can squeeze them at will—it’s what stops you from taking a dump when you read this column). The second is involuntary (you can’t consciously control it—it’s why you can’t stop from taking a dump when you read this column).

It’s that second ring, the involuntary muscle (less than a quarter inch from the outer voluntary one) that causes most of the pain in anal sex. If you can relax it you’re in for a great ride. If you can’t, you’ll punch your partner into the next room.

The idea of anal sex is to scream for more not yell for help, so “training” the inner sphincter muscle to relax is critical. That’s where butt plugs come in. If you keep them in long enough, the inner sphincter muscle relaxes on its own (muscles can’t stay contracted forever—at some point they have to release).

You’re going to have to use more than a butt plug to stretch the inner muscle if you want painless anal sex. So gradually introduce bigger and bigger dildos until you can insert one the size of your partner’s penis without pain.

Let me say that again, WITHOUT PAIN. Remember, pain is a signal that something’s wrong. You know that burning sensation you feel when you’re taking in your partner? It means you’re stretching the sphincter too much and causing micro-tears. God help you if you’re not using a condom because you just created a transmission route and put yourself at major risk for HIV. If you do it right (lots of elasticity training of the sphincter) you shouldn’t have any pain during anal sex. Discomfort maybe, but not pain.

Hey Woody,

I want to use condoms, but I’m allergic to latex. What other choices do I have?

– Scared Bottom

Dear Scared,

Your best bets are the polyurethane condoms like “Avanti” and “Trojan Supra.” They’re at least twice as thin and strong as latex condoms. They’re nonporous and non-permeable to all viruses, including HIV. You can even use it with oil-based lubricants (oil destroys latex condoms). The Supra is practically invisible on an erect penis, but here’s the problem: It’s only available with spermicide, which increases the rate of HIV infection. Hopefully Trojan will soon make one without it.

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Sweating Too Much

Hey Woody,

I read your answer to “smelly” (how to tell your new boyfriend his crotch smells like a grease-encrusted vomit bucket). Loved your answer but wanted to add a different dimension to the problem. I’m one of those guys who smell down there because I sweat so much. It’s very embarrassing. It doesn’t take much to soak my shirt. I could be in a mildly warm bar and sweat like I’m a whore in church. Any advice for people like me?

– Spikot

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