Organ Grinder:
News for Pervy Little Monkeys

International Dildo month IV:

So you're a het woman who believes that sometimes it's better to give than to receive. You've bought your dildo, you've chosen a harness, you just need one more thing: A willing playmate. This week, as promised, I want to talk about boys and bums.

Once upon a time, I had a lover who was extremely bum-shy. Wouldn't let me anywhere near it. Not even close enough to see the back doorbell, never mind ring it. I wished there was a way to introduce him to the delightful ways of the Prostate Fairy, but it was not to be. Sometimes you have to know when to let the situation lie. (We didn't break up because of that. We broke up because he was a Republican.)

Thankfully, he was an exception. I have found that most men are open to anal play, but the uninitiated (of any sex) will often take a little convincing. Switching roles can be extremely intimate and satisfying for both partners. Getting over social taboos and being truthful about your desires is just plain good for both of you. The following are a few tips on how to turn your bum-curious boyfriend into a certified Friend of Uranus.

• Broach the topic in an unthreatening manner. Leaping out of your closet with a set of handcuffs, a gigantic strap-on, and a vial of poppers is, generally speaking, a no-no. Wait for your second date. You want to choose a time when he's relaxed, post coital, even. Tell him you want to penetrate him, ask him how he feels about it. Be prepared to negotiate. 'It doesn't hurt when you do it to me' is a pretty inviolable position. If he's afraid that it will "make him gay", then you have two choices: A) Refrain from blowing him, on the same grounds; or B) Find another boyfriend who isn't such a chowderhead.

• Have some information on hand. Tristan Taormino's new book Pucker up: A Hands-on Guide to Ecstatic Sex has all the information you'll need to convince a skeptic that anal play can be safe, clean and satisfying. Lend him your copy if he's bookish; memorize chapter 6 if he's not.

• Promise him something nice, like a fabulous prostate orgasm or a new pair of pants.

• Start slowly, use your fingers and lots of lube. When you think you have enough lube, add more. You really can't go wrong. The tissue of the anal cavity is extremely delicate, don't take any chances on hurting him, or he won't want to play any more reindeer games.

• Trim those nails! Taormino gives a really great tip for femmes like me: stuff some cotton balls into the ends of a latex glove. Voila! My suggestion is to prepare this in advance, or maybe keep him blindfolded. Don't want any nasty associations with his yearly checkup.

• His prostate is only a few inches inside his ass and towards his navel; there's no need to traverse the whole pass before nightfall.

• Let's be frank: All of this is bound to go over better if you've got his cock in your mouth.

• Added bonus for you! If he orgasms while you've got your fingers in his bum, you can feel his PC (pubic) muscles repeatedly clench and release, fast and firm as a conventioneers handshake. Trust me, it is a thing of beauty.

• Once he's comfortable with prostate stimulation, you might want to try a butt plug instead of a dill. Plugs have a narrow "neck" and a wide base. This will reduce the stretching of his sphincter, which some people find irritating. If he wants in-and-out stimulation, then a dildo is in order. Pick one with a flared base, something smooth and smallish to begin with. Rome wasn't reamed in a day.

• It will probably take some time for both parties to get used to using a strap-on. The easiest way to start is in the doggie-style position, or having the penetratee straddle the penetrator. That way the receiver can control the action and establish a comfortable rhythm. For God's sake, start subtly and slowly. Porn movies are fiction, people.

• Cleanup: Don't share your toys, unless you're able to sterilize them. It's better to invest in something that's just for him. If you must share, put a condom on it. This also makes for easy cleanup. Yes, yes, the mess factor. If he has had a bowel movement and a shower, chances are you're not going to encounter much, if any, feces. If you do, just wash your toys with soap and hot water; it's only poo. Remember: Your mother cleaned up your shit for years and lived to humiliate you in high school.

• And finally: Keep talking, before, during, and after. Anal intercourse is one of the most intense sexual experiences that humans share, but it takes time and lots of communication to become adept at it. Unless, like me, you're a raving ass-gasket. Hey, almost everyone's a natural at something.