Keep Your Friends Close & Your Enemas Closer

The thing you need to keep in mind about anal sex is that, yes, exactly as you might expect, the act heavily revolves around that most unpredictable and untamed of regions: the butthole. And if, like me, just a whiff of coffee seems to trigger explosive bodily functions the magnitude of which could be compared to small earthquakes, sticking something up your butt is going to require some careful forethought.

I'll address the wildly gay elephant in the room (I'm seeing her as a washed up circus performer in lingerie smoking a cigarillo and getting peanut crumbs all over her bustier), but before I go on: I want this column to be the next Sex and the City as much as any self-respecting queer would; but while Ms. Bradshaw and I share some key similarities, in that we both have wild curly hair, self-destructive shopping habits and jobs writing about things that are often more self-indulgent than helpful or informative, we share one key difference: Carrie talks to boys a lot, and while I change my Grindr picture several times a week, in documenting my sex and dating history I anticipate I'll mostly be delivering a mixture of a body fluid diary, a review of various sausage egg and cheeses and references to the episode where Miranda wears a blue polyester tracksuit with a bucket hat placed over her hood.

But I digress. Anal sex. I'd gone on a few dates with this nice guy named Nate (to reiterate, I'm not the type of person who casually drops 'I'd gone on a few dates with' into stories. This is an isolated incident in an otherwise chilling sea of loneliness and party-sized bags of Fritos). Nate is 30, a grad student at Columbia with a one bedroom apartment in the West Village just steps from the F train--the New York City equivalent of having one of those houses in Big Little Lies. He's smart, nice and didn't flinch when I showed up for our second date in a leather mini-skirt with long lines of eyeliner spindling down from my lids making me look like a sad, dead clown considering a career in purgatory's thriving prostitution scene. Nate seemed like a no brainer. And after breathing through the pain, I'd use a word to describe the sex (him penetrating me) that I really never have before in describing my encounters with men: good.

I'd been sitting at my desk at work staring idly into the void when I decided I'd earned a much-needed break and proceeded to give my co-workers a lengthy, winding recount of Nate and I's story up to that point. I was startled when they asked if I'd "used an enema before bottoming" with him. Apparently it's protocol to flush oneself out entirely before being entered--a practice that, at least in my colleagues' circles, is understood to be both mandatory and obvious. I, however, had never even considered squirting liquids up my rectum, and I hadn't heard of any of my anally inclined sisters doing so either.

Now, my bravery seemed naive and foolish. Though I've yet to poop on a sexual partner, I've removed a dildo from my system before and been disappointed to find that while the penis may have been faux, the fecal matter astride it was very real.

Anyone who knows me will tell you I poop a lot. And anyone who knows me and likes to use medical terms in regular conversation will likely decide to diagnose me with Irritable Bowel Syndrome. It's part of what makes me, me. (Sidenote: If you're not comfortable with poop talk, I hope you got the idea to bail on this article a while back). I do my best to keep my butthole clean, but sometimes no matter how many wiping attempts one makes, there's still a certain element of uncertainty and resignation one has as they pull up their jeans and accept that sometimes, we try our best, and our best isn't good enough.

I decided an enema could be a great way to take out any fear of unpleasant excrement, so I might truly let myself relax and Nate could pound me good. After work I stopped by Rite Aid, and was delighted to note that enemas are sold next to laxatives, stool softeners and vitamins for the elderly. With my eyes glued to the album art of Dido's Life for Rent beaming up at me from my phone, I bought the enema and left, coughing weirdly at my cashier as I was overcome with unwarranted, childish embarrassment. Why should I have been ashamed? There are more incriminating things than enemas available at Rite Aid: hemorrhoid cream, for one. Flip flops, for another.

A quick update on what I'd eaten that day: two helpings of tuna casserole, which I'd made in an effort to save money and cook at home, but in reality had cost me a fortune since I'd tried to make it dairy-free to see if that would help out with my aforementioned shitting problem. Sadly, vegan mayonnaise costs an exorbitant amount, and I accidentally bought vanilla-flavored almond milk so my final product, which contained canned tuna, sharp cheddar, and crumbled potato chips, tasted like a really weird Frappuccino. But the ingredients all cost so much, I forced myself to eat it.

I entered the bathroom carrying the enema and the emotional baggage of two servings of tuna casserole, and, thinking I was above following the instructions on the box, proceeded to insert the pipette into my anus while seated upright and squeeze some saline solution into my cavities. It felt weird: like when you open your mouth to say something and a high-pitched rumbling sound happens in your throat that can only be described as an "interior burp" and your boss gives you a disappointed look and walks away.

Within minutes, liquid was cascading out of me like a waterfall into my toilet. I was also sweating profusely because my roommate had the shower running, but I'd asked to sneak in before she showered--I was running late for my date and needed to empty myself of all shit if I was going to feel confident having sex that night. Not a lot of poop came out, but I shrugged and decided to hope for the best.

Nate and I went and saw a movie together, and then ended up eating burgers--I was a fool! The enema had been for naught! There was no way in hell anything could go inside me after a "Hangover" burger (that means there's a fried egg on it, baby) and some cheese fries had made themselves a home in my stomach. We ended up cuddling after and I came way too quickly when he went to give me a blowjob, which is an issue for another time.

Two weeks had gone by since that fateful night, which I'd thought to be quite pleasant and tender--we talked about his relationship with his parents, cuddled naked in the morning and he even let me eat all of the salami fanned out like a meaty pinkish-brown flower on a leftover party platter he had in his fridge. I felt like he appreciated my offbeat sense of humor and decidedly uncategorizable choice in clothing and eye makeup. He was a little serious for my taste, but he bought me gin and tonics and really delivered when it came to rimjobs and real estate.

In an effort to rekindle our lust (and recreate the episode where Carrie meets the saxophonist with ADD), I asked him if he wanted to see some live jazz, and even researched locations. He enthusiastically responded, saying that sounded "amazing." I was excited--elated, even. Maybe this was more than just an opportunity to wake up in the West Village and imagine I was Sarah Jessica Parker, wondering why I agreed to sign on to Valentine's Day while sipping my morning coffee.

Despite our plans being locked in, Nate texted me later that afternoon: "I'm uncomfortable ever seeing you again because I don't want a relationship." I was immediately reminded of the age-old adage that I shall have carved onto my tombstone in Curlz MT: "Men are mysterious monsters that cannot ever be trusted or predicted."

Lately, with Nate gone and my pattern of crawling in bed to watch the Sex in the City episode where Miranda climbs aboard a mechanical bull in LA and rips off her shirt with a facial expression that can only be described as "orgasming while monstrously terrified," I've been thinking about enemas and the concept of flushing oneself clean. Even with my innards as empty as modern Rite-Aid products can achieve, I hadn't been able to sustain a casual relationship where both sides were satisfied. What I need now is a different kind of laxative: an emotional one. An enema for the spirit, so to say, so I might release into the proverbial toilet all the memories I have of eating "Hangover" burgers and nuzzling on Bleecker in order to make room for the insertion of a new phallus--one who just might, this time, not turn out to be a disappointment disguised as a 30-year-old student of American literature with Justin Bieber's Calvin Klein ad taped above his desk.

Sex and the Shitty is Associate Editor Hilton Dresden's column on sex, bowels and navigating the exhausting complexities of early adulthood in New York City. Dresden's regular reflections also serve as a shrine and humble servant to the iconic '90s show helmed by Our Lord and Savior Sarah Jessica Parker.