Tender Buttons, Tender Butts

Note: This week’s sex column contains more explicit material than columns printed in the past. We encourage you to assess your own comfort level with sexually graphic content before reading.

Dear Tender Buttons,

I’m comfortable with the vaginal sex I’ve been having with my boyfriend… comfortable being the operative word. We’re looking to try something new and surprising! He wants to try anal. I’m okay with it, but we really don’t know what we’re doing and I’ve heard some horror stories. Since asking our friends is out of the question, do you have any advice?


Dear Anonymous,

What’s with your sex-negative friends? Can’t handle an innocent query from a budding fudge-packer? Time to get a new posse, if you ask me. But you’re not asking me, so I’ll stow it and broach the topic nearest and dearest to my prostate: anal!

Yes, tender readers, it is time we pull apart our trembling inhibitions and plunge straight into the deep crevasse that is our collective cesspit of shame. Though the brave writer of this letter is a female in a heterosexual relationship, the content of this advice could apply across the spectrums of gender, sex, and sexuality. If you have a working anus and a safe (for the love of Sir Ian McKellen, please let it be safe) foreign object, pucker up and read on!

Anal sex is not for everyone. Like the soul from the first column who—for reasons best left to himself—cannot enjoy performing oral sex, some may find anal uninteresting, unpleasurable, or plain uncomfortable. You may dislike it, Anonymous, and that is just fine. However, do shake off any prejudices you may have before partaking. Anal is not degrading; it’s not even that far from vanilla sex. When added to a nightly repertoire, the act can stimulate a great deal of pleasure, regardless of the presence of a prostate. Find out if anal is right for you, preferably before skipping to it in the bedroom. Always use protection!

FiberOne bars are your friends. Clif Bars? Your new BFFs! The produce and salad bar at Collins? I eat there a lot. Catch my drift? No? Eat fiber so you stay regular. I don’t want to hear this nonsensical hogwash about anal: “I don’t want to do it! Doody comes out of there!” Yeah? Well, vomit “comes out of” your mouth, but doesn’t stop you from sucking face. Would you kiss someone with puke on their lips? I should hope not, and you definitely shouldn’t have anal before you drop the kids off at the pool! It’s common sense, people. Stay regular to prevent the “horror stories” from coming true.

Practice makes perfect… sort of. It definitely makes a more relaxed anus, and that’s what we’re shooting for, tender readers. Get to know your pucker. You don’t need to buy it flowers and take it to Bua Thai and a movie at the Laemmle, but don’t walk in blind! Explore the ins and outs with your lubed-up fingers. Gently. Very, very gently. Add fingers when your sphincters relax, and you feel comfortable enough to do so. Pleasure your genitals with your free hand. Make a night of it! Always prepare your anal cavity with lube before initiating anal sex.

GTL in Jersey denotes something horrifying. In anal-land, it means “Give direction, screw on a Towel, and use plenty of Lube.” Let’s break it down: communication is vital to the success of anal. Bottoms must speak up! Tell the top to stay or hit it. The initial penetration will be a bit painful—adjust to the sensation before proceeding (this may take a few minutes). Most bottoms agree that the Cowgirl position (receiving partner on top) is the easiest way to start things off. This way, the bottom may ease onto the phallus (or phallus substitute) on the bottom’s own terms. If Cowgirl isn’t cutting it, experiment with different positions to gain better angles and depths (Doggy will destroy you, in an awesome way). Keep applying lube as necessary, and let the washable towel catch any messes.

That covers ANAL101! For lube suggestions, I defer to the legendary Barbara Walters, who offered this sagacious advice to Kathy Griffin: “I pweefur Astwo-Glide.”

Don’t do anything I wouldn’t do—which isn’t a lot, but still,

Tender Buttons

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