The Odalisque, by François Boucher. Photo: Corbis

The Great Butt Stuff Normalization of 2014 was a bright spot in an otherwise grim year of conflict and turmoil. Articles flooded the internet emphasizing the pleasures of anal engagement and theorizing about the appeal of this highly sensitive pleasure center (that is also an actual sewage valve!). Some shook their heads and wept at the decline of old-fashioned sexual repression made evident in this sodomy-soaked generation, while others were excited for opportunities to dive deep into an exciting new hole. But with the normalization of straight anal play came expectations that it came standard. And because few of the articles championing butt play came with an instruction manual for first-time adventurers, the results were sometimes disastrous. If 2014 was the year anal went mainstream, 2015 was the year it too often went terribly wrong. But since 2016 is the year that we learned that perhaps even Kanye West enjoys a little anal stimulation, it is high time to talk about the basics of doing it properly.

This is not to say we made a grave mistake in destigmatizing anal, but people need to realize that shit is way more complicated than just sex in a tighter hole — and, if performed without proper precautions, comes with way more awkwardness, shit stains, and the potential to contract STIs. PornHub released data in November that showed a 120 percent increase in anal-related searches in the United States over the past six years. It seems likely that many people witness anal for the first time in porn and don’t quite register that porn performers are professionals. “The thing we don’t see in porn is the behind-the-scenes magic. These are professionals who have probably had anal sex before and know how to prepare, they are stretching their anus, and they are using plenty of lube,” says Megan Stubbs, Ed.D., a sexologist and sex educator.

Rearranging the letters in my name spells “Easy Anal Sam,” so it might seem like I’m a natural anal enthusiast, but I’m actually quite reserved about butt stuff. Yet 2015 was the year in which not one but two men went from going down on me in the way of the pilgrims to eating my ass without declaring their intentions. Another guy couldn’t stop himself from interrupting perfectly high-quality sexts with lines like “Then I stick it in your ass,” forcing me to be like, “LOL, no you don’t.” Several friends confirm that unscrupulous men are now requesting anal sex as early as the first date.

One friend reported that when she declined anal, the sentient pile of diarrhea of a man she was dating tried to make a case that she should do it because of feminism. Another was badgered for anal on a first date and eventually capitulated to the requests even though she wasn’t sufficiently relaxed or lubricated, then “got shit all over his dick and my ass” and “gagged from the smell for 15 minutes while his roommate was in the shower” before being able to clean up. She later got a urinary tract infection from what she suspects was the spread of rogue poop flecks to her vagina. It turns out Khia’s anthem “My Neck, My Back” is a lousy sex-education instructional tool. The lines “First you gotta put your neck into it / Don’t stop, just do, do it / Then you roll your tongue, from the crack back to the front” contradict advice that we’ve been given since preschool: Never go back to front. There is a scorching UTI waiting on the other side of that cavalier switcheroo.

Another friend, Anna, recalls a man she and her husband brought home for a threesome as “some young dumb full of jizzum, 24-year-old with a streetwear clothing line he was trying to launch, that I found on OKCupid” who was relentless in his pursuit of anal. Anna had a hemorrhoid at the time so was in no mood for anything except a cool slathering of Preparation H near her ass, but Jizzum kept trying to stick his dick in, then claiming he was “just joking.” Fast-forward a few days and her hemorrhoids feel like the worst case she’s ever had and she goes to a specialist to have them looked at. “They were like, ‘You have anal herpes,’” she told me, but the doctor wanted to be certain. “I had to walk down the hall crying with my gown open in the back and they put me on this chair and press a button to lift up just the end so my ass is in the air and stick this giant rod in my ass, which is like the worst pain I’ve ever felt.” The test confirmed anal herpes only from minimal contact on broken skin.

It also turns out my friend’s case wasn’t just unprecedented bad luck. “STIs can be easily spread — and indeed, the rectal mucosa (the cells lining the rectum) isn’t as tough as the cells lining the vagina (which is sort of made to withstand some ‘visitors’) — so STIs can be even more easily spread,” says sex therapist Mary Jo Rapini. Anal players should always use condoms for this reason, despite the lack of pregnancy potential. Again, this doesn’t make anal sex an inherently bad idea, and is not meant to make anyone live in fear of contracting an STI. People just need to be careful and prepared in order to maximize safety and pleasure.

“It’s unreasonable to expect to go from 0 to 60, by which I mean no anal sex to being able to have sex with a partner. So I always recommend people use a dildo first to see what it feels like and what works for them and what feels good,” says Zil Goldstein, a family nurse practitioner in New York. Goldstein and Stubbs both emphasized that the object used should have a flared base, because the muscle’s natural suction mechanism is activated when objects go in there. Butts eating toys is such a common problem that Deadspin publishes an annual list of items that were reportedly found in rectums.

It often seems that the purpose of these cautionary tales is to ridicule anal and create stigma around STIs, but the goal should be to demystify anal by discussing the logistics of doing it safely. Sure, I’m still angry at Jizzum and that Anal-Is-Feminist ghoul, but we should be committed to letting men (and women!) express their desires for anal sex. So I close with a story of butt stuff going just great. My friend Leanne loves anal and loves when men suggest it. She emailed, “The older I get, the more I learn how to like it. Some of my most intense orgasms have come from me lying on my back, a guy fucking my ass while his body is pressed against my pussy and clit. Holistic, if you will.”

LOL, “hole.”