My First Hookup Fuck-up

Everyone’s got at least one bad hook-up story. Even I do! Kinda sucks though that mine happened to be one of the first times that I ever hooked up with somebody else.

Let’s set the scene: it’s the summer of 2002, people haven’t figure out that Men In Black II sucks yet, The Sims is the best selling game of all time, and MJ is four months away from dangling a baby off of a balcony. Meanwhile, young, naive, closeted 16-year-old Nillin is about to embark on a series really fucking questionable safety decisions when it comes to having sex.

Generally speaking I was grappling with a ton of self-loathing and denial at this time, all of which was comfortably cushioned by a whole pile of intense internalized homophobia and transphobia. Ignorance was bliss, y’all! I really, truly was trying my absolute best to not at all acknowledge the mere possibility that I could be not entirely straight.

Here’s the problem though: I was horny. Like, horny as fuck. Oh! And also I loved cock.

No, you see, this was a problem because deeply closeted, totally not at all queer teen Nillin couldn’t possibly be into something like that, right? Nope, no way! There was no way that completely heterosexual Nillin was watching dudes frotting their dicks, jerking off together, or cumming all over each other’s erections on porn tubes… all the fucking time.

Not me! No way.

Except that I was, but rather than talk to anybody about my feelings, I did the only sensible thing a teen with secret sex urges for penises but no access to queer positive sexual health resources would do:

I hooked up with random, strange, adult men off of the Internets!

Now, we didn’t have any of these fancy hook-up phone apps or shit like that in the early 2000s. None of these Tinders or Snapchattles or Tickle Tocks. Instead, we used good ol’ fashioned forums! And at that time my go-to was gayedmonton.com (now a dead site).

I’d put up some basic details in a post, like a sort of age/sex/location thing followed by a straight up “looking to suck and get sucked”. I’d get a DM from somebody pretty quickly and me being the incredibly horny teen I was, would say yes to practically the first person that replied. I wasn’t picky. All I needed was a description of their car and a place to meet.

After my first hook-up with a skinny dude who dressed up like a cowboy and drove an expensive pick-up truck went surprisingly well (it was the first time anyone had given me a blowjob AND he swallowed!), I was pretty fucking revved up for more!

The very next night I start talking to another guy, let’s call him Justin (he looks like a “Justin” in my memory), who agrees to meet me at a nearby convenience story, he tells me to look out for a silver SUV.

I wait until everyone is asleep, quietly sneak out of the house, and jog steadily for the two blocks to our meeting place. Once the store is in sight, I see it, a silver SUV parked in idle right outside the front doors. Justin’s waiting for me! I feel myself growing harder in my pants, the anticipation of getting another blowjob exciting me so much I’m literally bounding across this parking lot with a full blown erection.

I bounce excitedly up to the passenger door, open it, get in, sit down, my cock throbbing, then look at the driver, smile and say hi, which is immediately met with an extremely firm, and terrifyingly serious “WHAT THE FUCK ARE YOU DOING IN MY CAR?”

A wave of panic flows over me.

“Uh, are you Justin?” I ask, and for the record this guy did NOT look like a “Justin”, I think he looked more like a “Rick”… or a “Bill”… or some shit like that. Point being that I asked this knowing damn fucking well that Rick, or Bill, or whatever his name was, was NOT Justin and this was clearly the wrong car.

So there I am. Frozen in sheer fucking terror. Staring wide-eyed at Rick’s, or Bill’s, or whoever-the-fuck’s now beat red face until finally he wildly screams at me “GET THE FUCK OUT OF MY CAR!”

And boy, do I! I got the fuck out of that car real fast.

On my way out I nearly barrel into another woman, who gasps and starts yelling. I believe she was likely the wonderful Mrs. Rick, or Mrs. Bill, or Mrs. Whoever-the-fuck.

Luckily, as I’m booking it away from the store the actual silver SUV I was looking for, Justin’s silver SUV, which was actually parked in the far corner of the lot with all of the lights off the whole goddamn time (fucking Justin…), pulls up beside me while waving me in.

Of course he is also fucking HOWLING with laughter and he can’t believe I got into the wrong car. We both had a good chuckle, mine was mostly a traumatized one, and I learned the extremely hard lesson of always asking for more detail before going out to meet somebody in a public parking lot.

Then I got my girl cock sucked, and like the skinny cowboy, Justin also swallowed! So, I guess it wasn’t all bad, but I’d be lying if I said my accidental run-in with Rick/Bill didn’t almost end my entire hookup career right then and there.

And yes, to address the elephant in the room here: I’m well aware of how dangerous it was for me to be sneaking out of my house as a 16-year-old to have the oral sex with older gay/bi/queer men. I definitely wouldn’t recommend this to anybody, and in retrospect I definitely wish that I felt more comfortable and confident in exploring my sexuality in safer ways. But when you’re living in fear, within closets, and there’s no affirmations or supports to be found around, sometimes you do stupid shit because it’s all you know.

Anyway, enough real talk, what fuck-ups and/or embarrassments have you had with hook-ups?