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My First Hookup Fuck-up

Posted on December 20, 2019December 16, 2019 by MxNillin

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?

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  • 5 thoughts on “My First Hookup Fuck-up”

    1. Mixter Promiscuous says:
      December 22, 2019 at 7:21 am

      OMG I can entirely see how 16-18 year old me would Totally have thought that plan was the beest. I’m glad you didn’t have anything bad happen but holy crap was that hilarious! Also, Ticky Tocks is what I’m gonna call them now. 🙂

      I’m not sure if it counts, but the first time I hooked up with someone (that I later went on to date) was underneath some stairs in the storage area of one of the dorms in my college. See, the thing was that she was apparently banned from my dorm for some things that happened the year prior (Red Flag), but I was 19 and REALLY horny so when she said. “We can just do it under there” I did NOT think about the fact that it would be dusty as hell and I spent the whole time trying not to sneeze from it while she went down on me.

      Reply
    2. J. Lynn says:
      December 20, 2019 at 8:25 am

      Ohmagawd! I’m totally fangirling over you and your story right now lol. I did some very similar and dumb things as well. I kept hearing the AOL dial-up sound as I read. I was in chat rooms around the same time frame, just a few years older than you as I lived alone. I always met them in a public place and once we went through the hi, how are you I would go with them to their place and fuck. The worst was this guy who was cute and well dressed but once he was naked he was covered, I mean fully covered in body hair. It would have been fine if he maintained it but he pushed my head down to blow him and it was like I was deep in the jungle. To make matters worse he wanted missionary afterwards and had a mirror on his ceiling, so I had a full view of how hairy he was. Maybe I’m a bit vain for telling you this but a little maintenance goes a long way! 😉

      I know this wasn’t safe either but I was young and horny. I did always tell a friend where I was though, you know in case I came up missing.

      Reply
      1. MxNillin says:
        December 20, 2019 at 3:21 pm

        Thank you so much for sharing your experiences too! I’m strangely really glad to hear from somebody else who had a similar phase haha. Omg the AOL sound, I thought I had forgotten about it but then as soon as I read your comment once I saw those letters it just sounded off in my head again!

        I REALLY sympathize with your experiences of hooking up with that extremely un-groomed guy though. And like, I’m a super body positive person myself… however… I would have struggled SO much with that too lol. You’re so right that maintenance goes a long way!

        Reply
    3. Kate says:
      December 20, 2019 at 1:02 am

      This one time I hooked up with this couple, and one of them yelled “it’s happening!!!” as they came and we all laughed and laughed and laughed. It wasn’t embarrassing for me, but they felt rather silly. 😂

      Reply
      1. MxNillin says:
        December 20, 2019 at 4:39 am

        I dunno that sounds like a pretty sexy thing to exclaim during a threesome to me! 😂🤣

        Reply

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