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Sex & Love 125 men later, I’m done

Jul. 30, 2021
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After breaking off a serious but very sexually liberating relationship when I moved to another city, I threw caution (and my bussy) to the wind.

I know how to navigate every hotel lobby in Toronto; I’ve learned a lot about my sleeping habits from concerned hookups who encouraged me to buy a mouthguard (note: game changer); I know which dark corners of public spaces to avoid; I’ve had too many text conversations with unknown numbers that ended with “that was fun”). Though I’ve had the time of my life, I’m thoroughly and utterly exhausted.

While sleeping with 125 men may seem like just an impressive number to some, it’s also given me the interpersonal skills I need to become a sort of cooperative project manager. Navigating the feelings of ego-driven men to get to the top (or should I say, a top), interviewing unqualified and unenthusiastic candidates in an attempt to fill the right position, scheduling multiple dicks at once amidst my busy social life, coordinating locations and proper time intervals in between hookups. It’s such a shame I can’t add “town hole” to the professional experience section of my resume. 

Something I can put on every cover letter is that I’m self-motivating, driven, and thrive under the pressure of coordinating multiple tasks at once. It’s why I enjoy bathhouses. So, keeping this schedule going worked for me for a couple years. Treating my sexual relationships with the same mentality as a TV sweepstakes contest—many will enter, few will win—was a good time for a long time.

A lot of people in my life have cast aspersions that this fervent behavior of rampant sexual proclivities would lead me to the eventual hoisting of my own petard, but I always thought that those people were just big-word-using prudes. I was having sex and they weren’t. They just needed to get over themselves. Sex is the most important part of any relationship. Passion is power, and who doesn’t want power?! But as a wise uncle once said to a boy who could shoot white stuff out his wrists, “With great power comes great responsibility.” 

The inevitable petard-hoisting came from an on-again, off-again casual relationship with a man I shall call Dan (not his real name, but a dickhead name nonetheless, so it’s fitting). Our relationship was raucous and dirty and all the filthy little qualities you look for in a person who you only have contact with a couple times in bi- or tri-annual chunks. It was great for a couple years, until I unknowingly started a semi-serious relationship with his long-time ex and found out that he (Dan, the dickhead) was an erratic maniac and liar who was rampantly cheating on his ex with the worst of Grindr (and that...includes me). The nail in the coffin was that I was hooking up with both volatile Dan and his really-great-did-nothing-wrong ex at the same time. Not my finest moment, but I persisted.

The week after this nice ex broke up with me and I left Dan on read, I scheduled an impromptu hookup with a man that had been blasting my Grindr messages as hard as he wanted to blast me. He wasn’t my type, but I wanted to start my healing process. My eat, pray, love, if you will—eat ass, pray his dick is big, love getting fucked. The minute I walked in, though, I wasn’t into it and wanted to get it done quickly. I didn’t even fully undress before furiously sucking this man’s dick to try to get him to completion. I followed his moans, put my all into it, and just as he was about to cum, he stopped me. 

“What?” I curtly remarked. “Nothing,” he huffed, confused and out of breath. “I just wanted to cum at the same time.” I rolled my eyes, “Ugh, fine.”

I went to remove my belt and he put his hand on my wrist. “You okay?” He asked. But of course I wasn’t. I had just blown my chance at a guy I really liked and now I was trying to blow my feelings away, too. But this guy didn’t want to hear that—he was nice and offered me the mutual satisfaction many men don’t. So I just told him I wasn’t really feeling it and left.

This wasn’t the first time I’d left a hookup midway through. My general rule for leaving a sexy time is to get out if it’s less fun than jerking off. Not a high bar, but there are surprisingly few men who’ve hit that, and therefore, haven’t hit this. But after that hookup I had a string of sexual encounters that I abandoned midway through for the same reason. I started to schedule fewer and fewer men, until I eventually put my apps to rest to mull over whether I was truly avoiding something...which lasted all of one month.

The apps were then put to work when I went on a string of extended work trips. Every time I would land in a new city, I would hook up with one man the entire time I was there. I basically set myself up with a harem of travel boyfriends all throughout Canada and the U.S. that fizzled out the minute I left. I spent so much time with the last travel boyfriend that I canceled my Airbnb to stay at his place. But as I left for the airport alluding to maybe keeping up with him long distance, he turned to me with confusion and asked why. When I looked shocked, he reassured me it wasn’t because he didn’t like me, he just didn’t see why I would want to keep seeing a man who lived on a different coast. Now, this makes sense, but at the time it hurt!

To heal from this utter rejection, I took a weekend trip to Montreal to visit one of my best friends, Greg (not his real name, but a no-nonsense name nonetheless, so it’s fitting). I spent the entire first day ranting about how unreasonable it was for this man whom I’d spent so much time with finding the idea of long-distance absurd. We could’ve been like Tom Hanks and Meg Ryan in You’ve Got Mail, or Tom Hanks and Meg Ryan in Sleepless in Seattle! Didn’t he have romance? Didn’t he want me to style my hair into a blond bob?!

Greg laughed at this, which made me even more indignant. But then he explained that he knew this man didn’t want me to spend time and energy on a long-distance relationship when I had plenty of options where I lived. To me, though, it felt like I had fucked every man I could back home, and fucked up the last relationship I’d even tried to get into. Greg then gave me the sage advice I keep him around for, which was: “Do you like this man because it was a good relationship? Or did you like him because you let your guard down while traveling and opened up to a relationship?” Fuck him… But he had a point.

I went home thinking about what he said, and decided to start actually dating guys without sleeping with them. It worked itself out. I’m with the man I now call my boyfriend of two years after an eight-hour first date of just talking and walking around in the cold (and Canada is cold). I mean, we eventually had sex, and it was great—thank God—but it wasn’t my biggest priority. Which is a good thing; sex is still a priority, but it’s not the priority.

As I’ve gotten older, sex in general seems less appealing. Occasionally, I let myself wander into thinking about what my life would be like if I added to the 125 men I’ve let scrabble my guts. Then I shudder as I think about all the shitty men I’ve let diddle their dangles at me. And that wistfulness disappears faster than a “straight” man after a Craigslist M4M encounter in a local park bathroom. (RIP Craigslist Personals, gone but never forgotten.)

I still get a random text every now and again from old tricks looking for a fun time, which I choose to take as a compliment, even if it might not be the most complimentary—though they’re a reminder of a chapter in my life I’m happy I went through. The prospect of returning to my whorish ways is definitely enticing, and might be something I return to one day (I’m still young and fun). For now, though, I’m gonna stick with satisfying myself in ways that don’t require me to sift through bots looking for my credit card information.