The Hackathon Sub

Petra here. Twenty-eight years old, corporate lawyer, owner of exactly one sensible trench coat. Let me tell you about the worst and best weekend of my adult life.

It started on a Friday in October when I lugged my overnight bag up to my friend Teddy's penthouse in downtown Austin. He was off to Vancouver for two weeks and I had volunteered to house-sit, mostly because his couch is better than my couch and his espresso machine is a religious experience.

I dropped my bag in the guest room, did a little lap of the apartment, watered the one sad fern, and then decided to snoop. Come on, you would too.

That's when I found it. On his nightstand, right out in the open like a paperback, sat a silicone plug kit. Three sizes, graduated, in a nice little zip pouch like it was a travel dental set. Teddy, you absolute dog.

I stood there holding the medium one like it was radioactive. And because I have the impulse control of a golden retriever, I took a photo and texted it to him.

Me: house sitting status report. Found your little zip pouch. Very discreet. Very classy!!

He replied in about ninety seconds.

Teddy: not mine lol. That's Gregg's, he crashed here last weekend. Left it behind

Wait. Gregg. There was only one Gregg in my history, and I had ghosted that man three years ago after one dinner date and an unholy amount of sexting. I was twenty-five and panicking and he was thirty-one and patient and I just... bailed. Classic Petra move.

Me: gregg like hackathon gregg? like GHOSTED GREGG gregg??

Teddy: yes lol. He's hosting the hackathon in my building's lobby space this weekend, come say hi, he owes me $40 anyway

So obviously I went down. Obviously. Do I look like someone with self-restraint?

The startup office on the second floor had been converted into a weekend hackathon hub, which apparently meant forty laptops, a coffee machine working harder than any human alive, and sleeping bags stuffed into the meeting rooms like it was a very nerdy sleepover. And there, in the lobby, holding two cups of coffee like he'd been expecting me, was Gregg.

"Petra!" he said, and he sounded genuinely delighted, which was unfair. "Teddy said you were house-sitting. You look great."

"You look old," I said, because he does now have a tiny bit of gray at his temples and it was either that or combust.

"Thirty-four suits you, though. Unfortunately."

"Smooth as ever. Coffee?"

"Yes please, oh my god, I've already had three but who's counting."

We sat on a beanbag chair, because apparently that's what founders offer lawyers, and caught up for twenty minutes. He asked about the firm, I asked about his startup, he did the humble-brag thing where he says "we're small" while waving at a floor full of engineers. It was nice. It was annoyingly nice.

And then, because I apparently hate myself, I told him about the pouch.

"Teddy left your little travel kit on the nightstand, by the way," I said, going for breezy and landing somewhere around strangled. "The silicone one. Very tasteful."

Gregg did not even blink. That's the thing about him, he never blinks at the stuff that would flatten normal men.

"Huh," he said, sipping his coffee. "That's not mine, actually. Must be Teddy's."

"Wait, WHAT."

"Kidding. It's mine. I left it last weekend." He grinned at me over the cup. "Why, did it interest you?"

"No! I mean. I noticed it. Noticing is not interest."

"Sure." He set the cup down. "You know, three years ago you talked a very big game over text and then vanished after one dinner. I always wondered if you got scared or bored."

Ouch! Direct hit! "I got... busy," I said, in the voice every lawyer uses when they mean coward.

"Uh huh. Well." He leaned back like we were discussing quarterly projections. "Here's a thought. Hackathon runs through Sunday. I've got a second kit in my bag, same three sizes, and I'm a very good teacher. Want to try anal for real this time, before the weekend ends? Actually follow through instead of ghosting?"

I made a noise. Not a dignified noise. Somewhere between a laugh and a kettle.

"Gregg! We are in a LOBBY."

"Nobody's listening, they're all debugging." He waited. That was the worst part, he just waited, calm as a lake, while my face did things I couldn't control.

And here is the embarrassing truth about me. Everyone at the firm thinks I'm prissy. Predictable Petra, cardigan collection, goes home at seven. I have spent three years being exactly that person and I was so tired of her. So when I heard myself say "fine, yes, challenge accepted," I honestly don't know which of us was more surprised.

"Okay," Gregg said, and something in his face went warm, like I'd passed a test I didn't know I was taking. "Baby steps. Wait here."

He pulled the small plug from his own bag, washed and dried, with a little bottle of lube. The small one was, no lie, tiny. Cute, almost. Purple.

"This is the starter," he said, pressing both into my hand and closing my fingers around them. "Small, plenty of lube, go slow. Wear it for the afternoon session. That's it. No pressure, and if it hurts, you stop, full stop. Agreed?"

"Agreed. Wow, you're really calm about this."

"I've been thinking about this for three years, Petra. I've had time to plan." He smiled. "Restroom's down the hall. I'll save you a seat next to me at the table."

I walked to the restroom like a woman in a dream. A slightly panicked, extremely aware-of-her-own-body dream.

Okay so, the restroom was one of those single-occupancy ones, which was lucky, because I stood in front of the mirror for a solid two minutes talking myself into it.

"You agreed to this out of spite," I told my reflection. "Spite is a valid legal basis. Proceed."

I did what he said, I really did. Lube, plenty of it, plenty. I leaned against the sink and took my time, one finger first, breathing like I was in a yoga class, which I have been to exactly twice. And then the plug, slow, steady, a lot of weird pressure and then, pop, in, and I gripped the sink and made a sound like a startled owl.

Oh my god. Oh my GOD. It didn't hurt, that was the wild part, it was just this full, insistent pressure, this constant awareness that something was there that should not be there, and every step I took afterward I felt it. Every single step.

I washed my hands about four times because my brain needed to do something normal, fixed my hair, looked at my cheeks in the mirror, which were the color of a fire truck, and walked back out to the hackathon floor.

Gregg had saved me a seat. Of course he had. He glanced at me as I sat down, and I swear he could tell. He probably