Creative non-fiction: Amorous errors, ages 17 to 22

Hello gentle reader,

Almost immediately following the demise of my second serious relationship I embarked upon the manic creation of what I termed as my “Oprah book” — tentatively titled: A Million Little Sequins. (I know, right?)

Although I got eggplant-emoji-deep in the creation of this memoir at the time, my interest in finishing the work at this time has waned to nil. Nevertheless, I am still proud of some of the comedic writing therein (I was a funny 20-something, once upon a time), and I might start sharing bits from time to time.

This chapter served as an introduction to the many frogs I had kissed before I met my temporary prince.

Please enjoy <3,

Amorous errors, ages 17 to 22

It would be impossible and indeed undesirable to catalog all of my romantic misdeeds in this book. Because a lot of it would be off-topic, and also this book would probably be several thousand pages long.

I’ve said meeting Ibrahim felt like my comeuppance for all the frogs I had kissed (*cough*) in days gone by, but I feel I may not have introduced you to enough of the frogs to understand why I felt this way. And so now, in as few words as I can, the tragicomic story of my amorous errors, ages 17 to 22.

At the age of 17 I lost my virginity to a dashing former drag queen who, to this day, is the last person to truly understand how much I like ear play. On my 18th birthday I met his friend Ellery at a Hanukkah party. Ellery asked me if I liked white zinfandel, I lied and said yes, and we were together for the next three and a half years, until he drunkenly seduced my best friend and I got in a terrifying car accident after driving her home.

(See, I really am trying to keep this brief!)

Ellery is the only person I ever really cheated on, and I really cheated on him. As you can imagine, I have mixed feelings about that. It started with an only slightly less than anonymous blowjob at a bonfire (about which I lied through my teeth) and was followed by that guy’s boyfriend (after which they got full-on old-timey committed to each other), my friend Luther with the bubble butt and gently sloping helmeted cock, a guy in the coat room (on the coats) at my first hipster party, and culminating in an ongoing romantic and vaguely sexual affair with my friend Jarvis which terminated abruptly when he never came back from winter break.

(I just got from 17 to 21 in less than a page. Can we just have a round of applause of my aplomb in keeping it brief?)

Actually, if you can believe it, Ellery and I did not break up immediately after, ahem, the incident. No, in fact, we bravely (read: idiotically) attempted to trudge forward, opening up our relationship in a good old-fashioned Hail Mary to see if we could get the spark back. Spoiler: fucking other people is rarely if ever helpful in reviving a moribund relationship.

The year previous at the New Year’s party in my old gayborhood, I had met a friend of a friend of a friend named, let’s say, Alejandro. He was portly and bald and his smile shone like a thousand suns, and he wrapped his hand around the tent in my pants when I got one of those persistent, throbbing vertical erections 20 year olds get because interest is base and oh, so easy. I pointed to Ellery and Alejandro courteously stood down. Unlike my penis.

But when we got snowed in at the same party a year later and Ellery and I were “in an open relationship, it’s totally chill, you guys!”, Alejandro and I spent days on end together. Mostly watching movies. He braided my hair. And then one night I fucked him, but he had panicky guilty feelings because Ellery was downstairs, and so instead he gave me the one and only hands-free blowjob from which I have ever cum. Alejandro told me to get ahold of him if Ellery and I ever broke up. And I thought about that until the time that Ellery and I did break up. When I called Alejandro a few scant months later to report that Ellery and I had broken up, he…kind of remembered me and told me that he had, in the meantime, moved to San Francisco and was dating his chef or grocery captain or something.

True love waits, but I just needed to fuck the pain away.

So I fucked the ringleted half-Ukrainian half-Italian kid from Russian class I used to have a crush on. I also picked things back up with my friend Luther for a very hot summer. He chipped a tooth and we kept going, I’m just saying.

I had an 8 Ball date with a very popular local DJ who always needed to catch a cab before anything interesting could happen. I went on three serene but unconsummated dates with a stoner who had smoked his libido away. I blew a terminally boring businessman who had the temerity to send me a message about how I wasn’t his type, the jerk. Though to be fair, I had worn khakis on our date to a vegetarian restaurant, so I might not have been putting my best me self forward.

One night at Arbor Vitae – the Ann Arbor apartment to end all Ann Arbor apartments – I met a patchily bearded emaciated hipster who spilled his Muscle Milk on me because he wanted to lick it off me. Muscle Milk, in the likely event that you’re unfamiliar, is a terrifying bodybuilding diet aid that smells uncannily like human breast milk. Which everyone knows is the best smell in the world! We kissed so intensely and so relentlessly that it took maybe a half-hour to walk the three or four blocks to my sublet. The sex was so good, I boasted to my friends the next day, that I had lain in bed that morning and masturbated just thinking about it.

I spent the next six months fucking myself raw. I glossed over it for the sake of brevity – and honestly, to not have to plumb it too deeply – but having your partner and best friend fuck each other will actually totally fuck with your life. When something terrible happens, you’d immediately think to turn to your partner and your best friend, but that’s a non-starter when they are the terrible thing that happened.

Dick joke!


The fall of my senior year in college I moved into what would become but was not yet an uninhabitable, terrifying crack house whose major benefits included being five minutes from campus and three minutes from Beer Depot. This, in case you’re wondering, is an excellent base from which to launch your descent into madness. Sex madness. Also drug madness. Have you guys heard of using other people’s ADHD medication recreationally? Because I hadn’t, but I was about to!

My straight crack-housemates were absolutely fascinated with the idea of Craigslist hookups. This was in the days before Tinder, i.e., when straight people who wanted to hook up would just take advantage of the fact that available horny straight people are literally everywhere and just flag down available ass on the street. Once they found out what I was doing, they forced me to introduce them to my next hookup – who turned out to be an awkwardly built ginger with fluffy sideburns who didn’t smell particularly good. Have you ever introduced an online hookup to people who have never had anonymous sex? They acted like we were going to prom, whereas really we were going to the backseat after-party. Some gays, especially gays my age, might be uncomfortable exposing the furry underbelly of gay life to the straights, but I have never believed in tricking straight people into liking us. Besides which, just like everything else, they were about to steal anonymous hookups from us.

RIP, disco and brunch.

I fucked a nervous boy with a pencil dick. I fucked a grad student with whom I accidentally discussed the Orange Revolution in bed. I fucked an older journalist who was splitting town because the local paper was going under. Two virgins the month I turned 22. Diaper guy and socks with sandals guy. Cuddles with barrel-dicked friends and more come-ons from straight men than you could shake a dick at.

And then there was Alistair. Alistair Buckinghamshire. Or something equally British. By the middle of the New Year’s Eve party at which we met, people were mistaking him for my boyfriend. He motioned me to follow him into the bathroom, where I held his tree-trunk penis while he pissed. We rounded out the night fucking in a back basement room, trying not to skin our knees on the bare cement.

I saw Alistair every once in a while for the next couple of months. He’d bring a bottle of sweet tea vodka (which totally wasn’t cool yet) and he’d wear his fluorescent track pants. He’d share a drink with me and Frankie or whoever was around – he really liked being around my friends, which seemed like an excellent sign. And when we’d had our drinks we’d go up to my very small room on the third floor of the crack house and feel each other into sensory oblivion.

The first time Alistair and I made love in the crack house, I saw him to the door and then collapsed on my friend Gina’s floor, exhausted and reeking of sex. I didn’t want to wash him off me; I wanted to be nestled in our sex like a hammock or a womb.

It was so grown-up and tawdry. Alistair was seeing another man in Toledo, and he’d say things like, “I can easily imagine a future with one of you.” He’d tell me about blood play and things he’d do with other lovers. Having a penis that couldn’t fit in any human orifice made Alistair a creative and dynamic lover.

And I thought I was going to be really good at this. I mean, I was majoring in Russian! And Russian literature is basically French literature with more exclamation points. I knew about fucking around. I knew about people having feelings for more than one person at a time.

The fact that those characters usually die of consumption or throw themselves under trains was apparently lost on me.

I didn’t have the emotional vocabulary for it yet. Alistair lived in Down River and would withdraw, sometimes for weeks. I didn’t understand why he didn’t want to keep up, keep in touch. Maybe I thought he was picking Toledo guy over me. I was scared that I had blown it.

And so, one drunken night, I posted not one but two Craigslist ads trying to get his attention. I used only his first name and the detail about sweet tea vodka, but that was enough to start getting messages from other guys from whose lives Alistair had disappeared. I woke up the next morning to a stream of angry, hurt texts from Alistair. All along he had had regard for me, at least in part because I was cool with his detached way of life.

But I wasn’t cool. I was becoming ever increasingly less cool, in fact. I had, in all likelihood, known exactly what was going to happen. But pressing my luck seemed like a better option than living with the gnawing uncertainty in my gut.

Valentine’s Day that year, Frankie and I went out for sushi, and she enacted a public performance art piece wherein she screamed at me about continually cheating on her. I drank to still my nerves. I got high so I would remember to eat at least once a day. I snorted Adderall because it was fun, and I smoked opium because it was there. I was in my final semester of college and working on my undergraduate thesis about futurism and fascism. I was small and we ate out of dumpsters, and my Polish teacher excused enough of my eighteen absences that term for me to graduate.

A couple of weeks before graduation, I met Albee. At, as you might imagine, a thundering co-op party in Kerrytown. Albee was a friend of Frankie’s, and I went to the party knowing there was going to be a cute, smart faggot there I could talk to.

Or fuck all night on a sketchy attic mattress.

Albee, it would seem, had also been alerted to my presence, and was just drunk enough not to bother containing his delight. There was a certain ease of charm that came off him as we glided around the party, laughing at his housemates shedding layer after layer of clothing. Beyoncé and boobs were, after all, the watchwords of our day.

In his lustful haste, Albee popped the button off my poorly constructed hipster jeans when we got upstairs. He took me in his mouth, wresting my boxers from around my waist. Albee’s slight build and artless mop of hair made his seem naive and ingenuous, but his surprised moans as I ate his ass – I later discovered this was his first time being eaten out – hinted at a hidden sybaritic nature that I longed to uncover. Our cocks were almost exactly the same size and shape, and I thrilled from my core to take them both in my hand as we rocked passionately against each other on that sketchy attic mattress.

The next morning he made me pancakes in the co-op kitchen while I clutched my pants shut and made small talk with one of his housemates. It was the longest walk of shame ever, but I felt like a fucking god.

I’ll always have fond memories of fucking Albee. He was so slight that he could straddle me in my office chair, and he did everything with the gusto of someone coming into his own. Discovery is the most wonderful part of sex, and that’s why I always prefer to have sex with someone more than once. He’d say, “I liked that thing you did the other night,” and I’d my bury my face in his trim, joyful ass until he’d turn purple and shout with relief. Once, Albee stopped me in the middle to ask for a cigarette, despite the fact that he didn’t smoke. That makes you feel about as cool as the hair on John Wayne’s balls, in case you were wondering.

In the logical part of my mind, it was a spring fling. The ideal spring fling. He was off to NELP, and I was graduating from college. After coming out of my crushing winter doldrums with Alistair, exploring my vernorexic ache with Albee was a pertinent and much needed exchange.

But you don’t explore a vernorexic ache with a purely logical mind. As a Republican senator just caught with a nude masseur might say, mistakes were made. For instance, I bought him a flower.

For another instance, I let him fuck me.

I admire bottoms who can have NSA sex. But when I bottom, shit gets real. I attach. Lo, these years later, I know myself better. But Albee was only the second person for whom I bottomed (the first being Ellery, my first long-term partner), and I keened with anxious need when he asked me if I had a condom, and if he could use it on me.

The image of Albee over me is forever emblazoned on my mind. He had discovered a new toy, and it was my ass. I grabbed him and pulled him deeper into me, looking him full in the face and pleading for him to cum in me. He stared back, bemused. Obviously that was the point.

I had sexually transmitted crazy mouth. I was human Bondo and he had just discovered a new way to detach from sex. That ridiculous orange condom on his cock punched through the flimsy layer of cool I had left, exposing me for the demonstrative, needy puppy I was.

And so it came to be that, at another hipster party at which I was only tangentially welcome, I found myself sniffing around about our future. When Albee balked – because nothing is less hot than your fuck buddy talking about the future – I quickly recalculated and told him we should just have a good time while it lasted. It was a desperation play to hold onto something, the value of which had become artificially inflated because I took it inside me.

I took him home, he fucked me one more time, pulled out, and said he wouldn’t see me anymore. He was still hard, the ridiculous orange condom still on his cock.

“I am not a hole!” I shouted, pushing him off me.

I could barely contain my rage. I had opened my ass to him and now he was swaggering out of my life with a new love of topping and a story about some crazy bitch. I had given him seven inches, and he had taken a mile. He’d fucked all the way through to my heart, and I was just a warm place.

It was the small hours of Saturday, April 25, 2009. I know that because I awoke to the news that Bea Arthur had died. Frankie took me to BD’s Mongolian Grill and insisted on buying me some obscene giant blue cocktail. Bea Arthur was dead, and I was dumped. If some piece of anti-gay legislation had come down that day, I probably would have turned that Mongolian BBQ into my own personal Stonewall.

“The condom was still on,” I would lament over and over in the days to come. “He was still hard!”

My friends really rallied around me after Albee dumped me in what basically everyone agreed was possibly the harshest way possible. When one of my housemates, Sterling, saw his girlfriend off on the NELP shuttle, he told Albee that was he had done to me was really fucked up. Even Albee’s friends would come up to my in bars and say they were sorry. Everyone had this sort of wide-eyed shocked expression, like they were a little upset to be friends with the kind of person who could do what Albee had done.

A few days later, I graduated from the University of Michigan – with honors, I might add. I didn’t realize my family was staying in town for lunch, and every even halfway decent restaurant had been booked for weeks, so we ended up at one of those chain places out by the mall where they have trademarked cocktail names and bacon-fried bacon. My mom got a Middle-Aged Lady Blue Raspberry BoozBowl™, and, after a couple of sips, her head started flopping around and she asked me about my sex life.

“Is that – is that a hickey on your face?”

Oh yeah. Did I not mention that Albee had left me with a FACE HICKEY?



The stage was more or less perfectly set for my sex life to collapse in on itself. Like a dying star, or a dance mom who realizes her three year old has lipstick on her teeth. In the past year I had slept with at least 50 people, most of whose names and faces are lost to me now. I didn’t feel any less dead on the inside than I had when I finally left Ellery. And, though I know this will shock you, I had even found new ways in which to feel dead on the inside.

I’m not rhapsodizing about the moral quality of sexual promiscuity, because I don’t think the quantity of sexual partners you have has a moral quality. I don’t even think that’s a question, ok? Having sex with lots of strangers didn’t hollow out my insides and pour the bad feelings in. I have a lot of fond memories of being of that time of my life because…well, because I was 21, 22 and barely had to lift a finger to get completely adequate and sometimes amazing sex.

But my sex karma was coming for me. I thought I could bury my feelings of hurt and betrayal up other men’s assholes. I was wrong. I thought I could supplant my need for love with some combination of fucking and never being sober. I was wrong.

That summer I started going over to my friend Bastian’s house deep in the Old West Side to watch movies. He had long, tightly wound curly black hair and varying degrees of scruff. He was a femme queer feminist from a small shitty rural town, and we could identify on more things than not. We’d watch Female Trouble or listen to his Dolly Parton records, all the while dancing around each other. And I don’t mean literal dancing; I mean trying to establish if this was sexual tension or just tension. Then one time, during Hedwig or something, I fingered him under his kilt and he gave me literally the worst hand job in the history of the world. It was like he was punishing me for being circumcised.

I moved out of the crackhouse early when the junkie I may or may not have been sexting threatened to kill me. That fall I went to another party at Arbor Vitae where another junkie pinned me down with his forearm and forcefully made out with me. We got most of the way back to my house by the stadium before he said he had to go back uptown to score. I walked past him on Main Street a week later and he asked me for a dollar. My mojo was gone, my cool was gone, and my days of fucktons of casual sex were distinctly over.

It’s really tempting to tell you I realized something deep and impactful about myself at this particular juncture in what was currently passing as my life. But I did not go gentle into that good night. I didn’t know the jig was up; I thought I was going to be balls deep in adult situations until my left arm went numb and I went to that big dive bar in the sky, clutching a bottle of whiskey and the cock of a significantly younger man.

I’d also like to tell you that I have some sage wisdom to offer you about being a slutty 21 year old, but, 1) 21 year olds don’t take advice, and 2) the only insight I can really offer you is to enjoy it while it lasts. You’ll hit the brick wall eventually, with time varying based on how attractive you were to begin with and how much of how many drugs you do. Being a slutty early 20-something was amazing.

Making up for it was not.

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