9 min read

My precious little hole has a tear in it and I'm too embarrassed to tell my friends

This was originally published on August 25, 2022 back when this newsletter was on Tinyletter. It's quick, rough, and perhaps in need of an edit. I hope you enjoy it in its full, messy glory.

The sun is setting at an absurdly early time, like 4pm or something and I hate to give in to my animalistic instincts but it’s like I’m immediately going into hibernation mode. I have barely written a word lately. When I was on Sister Spit, I felt inspired by the devotion to writing that everyone around me had. They were like, serious artists in a way that I hadn’t seen up close since I burned out of the art school industrial complex. I missed being around intense, fun, weirdos. The rhythm of tour was conducive to making art – there’s a lot of down time and a lot of inspiration and fun places to sit and write at. I make promises like this to myself all the time, but this time I promised myself to be dedicated to writing in a real way. Get up and spend an hour at least everyday writing. I mean Jesus I call myself a writer, out of pride or so that I could have some sort of anchor weighing me down in this life, the least I could do is actually…write.

Tonight is one of those nights where I could write for hours. No one’s really around. It’s the beginning of what seems to be the eternal Chicagoan winter everyone dreads and it’s pitch black outside at 4pm. Drinking alone wore itself out as a novelty pretty early on in moving here. So, not a lot of options for fun...(or maybe I'm just boring.)

I opened my laptop to write. I'm immediately googlign to see if Steamworks was open. Steamworks, if oyu don't know, is a gay men's sauna. It's where gay men go to walk around and cruise and hot tub and also there's a gym at the top. So masculine! I find that they’ve recently gone back to a 24 hour schedule – as recently as a week ago. Lucky me. It’s a 45 minute trek: a bus to a train in 34 degree weather. That sounds miserable… Although, the cold weather is making sitting in a hot tub with naked dudes all the more appealing. There’s no guarantee they’d be sexy men, but it’s still a fun idea.

Quickly I text my roommates and my boyfriend where I’m going to spend the evening. bye-bye writing night.

The commute is really not that difficult. Once the train is in Boystown, it’s like a 5-minute walk to the bathhouse or something. Anxiety doesn't kick in until about 30 seconds before it’s going to happen. As I approach the building, my breathing shortens a bit. I wonder if my old passport – under my old name listed under a picture of an acne ridden, undercut-touting, beard-having boy – is a valid ID. It hasn’t expired yet, but I look completely different. Steamworks lets trans women in every Third Thursday of the month or something and trans dudes can come in any day, but it’s like, the second Wednesday of the month tonight. My boy-mode look doesn’t really sell anymore. I kind of just look like an androgynous eunuch of indeterminate gender even without a mini skirt or make up on.

The attendant sees my bag and tells me I can’t get in – not because they’re excluding a tranny or anything, they just don’t let you in with a bag larger than a fanny pack anymore. They tell me to check the bars down the street for coat check – as if any bar’s going to be doing coat check for all five of their customers tonight.

I decide I can’t just go home after trudging through 45 minutes in the cold. I want to hot tub tonight god damn it.

In the end, I’m marching around the dead strip of gay bars sadly asking if they’re doing coat check. It’s so early, some of the bars seem to be doing pre-shift meetings of some kind and they look at me through the window looking back at them with slightly disgusted looks on their faces. I wonder if my desperation is showing. And no, no one is doing coat check.

When my besties came to visit recently I discovered this service that would hold your luggage for a few hours or a few days – I imagine it’d be useful if you had a layover and didn’t want to drag your rolly suit case around while you did touristy things in the city. Miraculously, there was a service spot available here, in the space between Boystown and Wrigleyville, the grey area between gays and straights. I relate to this grey area and feel grateful for the existence of this cash-grabby tech start up service.

The suitcase-holder-attendant was also running a smoke shop. After making a reservation through the website, my credit card gets charged and I receive the address. I march the two blocks to SmokeZone and drop my bag off with him. I probably should have felt more unsafe giving my beloved Telfie to some dude selling hookah and puff bars to hold , but I had already used this semi-suspicious service before and it worked out that time… Plus his door automatically locks and he seems nice enough. It's like, secure.

After that sad little parade, I finally got into Steamworks and hot tubbed away. There wasn’t many sexy men, which I was expecting but it’s always liberating to walk around a place naked. Plus, gay bath houses are built like casinos – labyrinthine and dreamy and pumped with shadows and house music and vibey LED lights. It’s comforting to my Las Vegan sensibilities.

I spent a few hours walking around the foggy three-story maze, hot tubbing, showering, laying in my rented room watching very basic gay porn. I wish the hot tub was hotter and the men skulking around were hotter, and the porn on the weird TV was hotter, but it ultimately wasn’t a bad way to spend a Wednesday night.

Close to the end of my stay, I get lucky cruising and get a few men to follow me to my room. We negotiate and awkwardly get ourselves into the act of fornication – something that’s easier once you’re in the thick of things and everyone more or less has assigned themselves a role. The thing about cruising is everyone’s always trying to communicate silently, trying to figure out who’s topping, who’s bottoming, who’s sucking, who’s hard, who likes to watch. It’s hard to signal that sort of thing but we all try to do it almost entirely with eye contact. Once you’re talking out loud it feels almost like cave men are attempting to invent language for the first time. But being a tall femmey person, people are always a little confused about what role I’d like to play, so we have to get verbal before we get physical. I'm unsurprised that I'm clearly still femme-of-center here. Everyone calls me baby girl when they fuck me despite the fact that this is a men's spa. I get the urge to shush them - secretly wondering if they'll kick me out if they realize I'm a giiiirl.

I leave before my time is up because I have to pick up my purse from the smoke shop before it closes. It was a decent time spent all in all, but what I hadn’t realized yet was that one of these dudes has torn my asshole asunder.

Sometime in 2014 or 2015

I snuck away from the house around 9 or 10 pm, I think. It’s not too late, but my dad goes to sleep like a brick after a couple of shifts in a row. I can tell it’s a sleepy night for him. I put an ad on Craigslist offering myself up as an inexperienced twink looking to learn how to bottom. Inexperienced is an understatement – I’m a total virgin. I’ve sexted people, watched porn, had strange psychosexual sapphic frenemy sleepovers — but I’ve never even kissed someone. That’s all to say, in terms of physical intimacy I’m a total noob at this point.

Someone replies to the ad. I mean, a few people do, but this guy actually seems normal – plus he sent a pic. He’s a self-described mixed guy, a jock. He offers to help teach me. I reply in kind with a relatively chaste selfie I’ve taken in my underwear on Photobooth. Surprisingly, nothing spicier is exchanged before we make plans to meet.

I drove 25 minutes out to a dark housing development at the edge of the city. It’s a bunch of tract houses, freshly built. This how Las Vegas expands, with these tiny, abandoned neighborhoods built before there’s anything else nearby. He’s parked near the entrance of the little village of homes and signals me to follow him once he sees my car.

The two of us trail around the subtle zig zag of the streets. The whole neighborhood is completely dark. Maybe two or three houses near the front have been bought, a parked Beamer out front indicating someone’s home. The rest are empty.

We park near the entrance of the cul de sac. He finds a key in the gravel outside of one of the houses and lets us in – he reveals that he’s got a deal with his friend to use this spot. I put together that it’s not his house, this is probably on the market right now or something and they both use it as a place for hook ups.

I don’t know this guy’s name, but I’ve always called him Gym in my recollection of this story because he looked like a gym teacher. He wore athletic clothes and practical looking runners. We stop right in the front door way, closing and locking the door just 5 feet behind us and he sits in a wicker chair he’s pulled up. He prompts me to get on my knees and blow.

In the end we’re both on the floor. His dick is bigger than I thought it’d be. Years later, it’s probably the biggest dick I’ve ever taken into me and now I know I was not ready for that kind of hook up. It’s painful the entire time, uncomfortable. But I wanted to get on with it and just not be a virgin anymore – I mean, I was about to graduate high school! It was time!

And in the end, I did indeed leave the unnamed, dark neighborhood, a newly non-virgin. I didn’t know when we were doing it, but I’d also discover the next morning that I’d left that housing development with another new character trait: a torn asshole.

NOV 17, 2022

It wasn’t enough that someone slid it in at the wrong angle or got a little too crazy with the pumping and ripped my hole in twain. it’s that a couple of days later, I started getting sick – I was out for two days straight sleeping through a fever. That’s kind of my body’s response to being sick in general, even back when the common cold was just a common cold. It shuts down and I sleep and radiate heat, cooking off all the germs while I lay motionless for 48-72 hours. In the mean time, I’ve got the worst cold sore the Earth has ever seen – it’s like three huge ulcers are eating up my bottom lip, and newly formed acne dots my nose and chin. I feel like a teenager. I say it’s acne, but lets get real. It’s herpes. Ugly. I’m embarrassed. It feels like God is punishing me for being a slut. But like, I used protection! That’s more than we can say about God up there, getting people pregnant from sitting in precum (Mary), but I guess herpes can flare up when you catch a regular-degular-not-from-having-sex virus. The opportunistic little freak breaks through while you’re already down and out. So I guess I don’t even know if this is related to any sex romp, even if it feels like it. Some jerk could have coughed on me on the train and took me out, allowing some strain of herpes I contracted as a CapriSun-sharing-Fifth-Grader to jump back out and terrorize me. But regardless, it sure is preventing me from going on anymore sex romps.

The worst part isn’t even that it hurts when I wipe because my precious little hole has a fissure tearing through it or that my sex-haver-fever stole two days from me. It’s that it feels like I’m marked. I can’t seem to get anyone to want to hang out with me after we fuck, or I can get along with people on dates only for them to ghost me before we fuck, so the whole searching for a fun polyamorous non-monogamy new partner thing is a bust right now. Even these little trysts with strangers are off limits until I heal from being an ugly hag and my hole becomes usable again.

It’s times like these when you all you can do is look at your little herpes-ridden face in the mirror and think, “Wow, I’m such a loser,” and get on with your day.