Butthole pleasures are somewhat en vogue right now, and I think a lot of readers are interested in hearing about them. For those of you who find the idea a bit distasteful, you can just sit by and giggle at phrases like “slippery, stinky slope” and “rim job.”

Anal sex has been a huge sexual taboo for a long time. There are laws against it dating from the Old Testament to modern legal books. The word sodomy — shiver — makes anal play sound so wrong.

But, naturally, there’s nothing wrong with anal sex. The anus happens to be extremely proximate to both the male and female genitalia, and, what do you know? It’s a hole capable of taking in and moving out large objects. And let me say once and for all: Enjoying anal penetration does not make you gay.

A man’s prostate can easily be reached through the ass. To stimulate the prostate, a partner can insert a finger into the anus, search for a walnut-sized mass on the stomach-side of the cavity, and then massage gently in a downward motion. This method has been proven to be extremely effective at producing an orgasm. It is even used therapeutically by some doctors to alleviate prostate problems. Don’t get too excited; the Student Health Center does not provide this service. A prostate stimulation-induced orgasm is different from a typical one in that the semen flows from the tip of the penis rather than squirting.

For a woman, anal play can be exciting for a number of reasons. The pressure exerted by an object in her butt can push pleasurably against her vagina. Additionally, since the anus is further away from the clitoris than the vagina, anal sex can provide ample opportunity for digital clitoral stimulation. It can also open the way to the pleasures of double penetration.

Nevertheless, anal sex is still a difficult topic to bring up comfortably. If you are dealing with a casual hook-up, one-night stand or drunken monkey love session, your only option is to be outright and quick about requesting it. You probably won’t have a chance to have a nuanced conversation about the potential positives of going in through the out door.

Remember that anal sex is an extremely intimate act. We have been conditioned by society our whole lives to see our anuses as private parts, even led to believe that what happens there is a shameful process that should never be shared with another human being.

In the confines of a relationship, the idea of anal sex may be easier to bring up. When is the right time to pop the question? I can’t tell you. The answer is whenever you feel comfortable having an open conversation about a delicate topic. Be honest about your desires but don’t expect your partner to share them. Guilting your partner into anal is a bad idea.

I feel it necessary to bring up a small point here, but the very necessity of its mention makes me a bit disheartened with humanity: Do not spring this on your partner in the middle of sex. You’re in her vagina, in and out, in and out, and you more-or-less accidentally slip inside her ass. Ooops. Not okay. Never okay.

If you’ve discussed the issue and you’re both game, it’s time to get down to it. The most important thing to keep in mind when having anal sex is that lube is your best friend. Unlike the mouth and the vagina, there is no natural wetness in the anal cavity. Trying to insert anything — even something small — into the anus without lubrication can create an incredible amount of uncomfortable friction.

Start by making sure your partner is comfortable. Reassure each other that you don’t consider anal sex gross. Move slowly and respect your partner’s wishes; if one of you finds it too painful the first few times, do something else and try again later. If you are okay with the idea, analingus — also known as salad tossing, rimming or partaking of the pu pu platter — may be helpful. In addition to drawing a connection between the pleasures of cunnilingus and fellatio to analingus, it will increase the amount of lubrication in the area.

When slipping inside of your partner, whether it is with anal beads, butt plugs, fingers or the good, old-fashioned hot beef injection, proceed with caution. Move in and out without fully removing the object. Once you establish a level of comfort, you can work up to standard patterns of rapid thrusting, full removal before reinsertion and deep penetration.

Before you’re free to frolic in the anal pasture, you may be wondering whether all of this can get rather dirty. The answer is yes, but really no. We are all aware that the anus’s main purpose in life is to excrete feces. Unless you are into fringe play involving excrement, the thought of dealing with your own — let alone someone else’s — fecal matter probably doesn’t excite you.

The only thing to worry about is there being feces in your partner’s rectum. The rest is all stored farther up and won’t bother you unless you have a huge penis. To ensure that you do not get the dreaded shit dick, have your partner clean up before you perform the act. An enema would work, but probably isn’t necessary.
Condoms can act as a shield against poop as well. A condom is a good idea anyway. Sure, no one can get pregnant from ejaculate in the rectum, but the risk of sexually transmitted infections is higher with anal sex because of possible tears and insufficient lubrication.

Another health risk is hole-jumping. The vagina and anus have delicate balances. Introducing new bacteria and fluids can lead to infection. Therefore, if you plan to hop from puddle to puddle, make sure to switch condoms or, if you’re reckless and not using a condom, wipe down before entering.

And of course, don’t lose anything down the rabbit hole. Make sure whatever you’re inserting isn’t going to have a piece break off, never to be seen again.

That concludes today’s lesson. Of course, there is a great deal of other information out there to help prepare you for crossing this sexual threshold. I’m a little afraid that I’ve made some of you nervous. But don’t be. There’s a good reason that anal sex has been around since biblical times: Playing in the mud can be great fun.

Maya Horowitz is the Flat Hat sex columnist. She hopes you reconsider the tossed salad at the Caf.