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Chapter 39 by Meaniehead
Portugal...
Day 3: Kennedy (Leaving On A Jet Plane)
You book the flight at 7:14am. Round trip to Lisbon, wheels down Thursday afternoon local time. It’s just under $2,100 — a coach seat with a brutal overnight layover in JFK. The screen flashes confirmation, and suddenly the money you made from being publicly tormented on a BDSM cam show becomes a ticket to anonymous sex in a foreign country.
There’s something absurdly right about that.
You pack light. Everything fits into one small backpack: a clean shirt, a few changes of underwear, the tablet, your passport, charger, breath mints, deodorant, and not much else. You polish the tablet camera lens with the hem of your shirt. You’re not sure why. It’s just something to do. A ritual of preparation for something that doesn’t feel entirely real yet.
Before heading out, you message Kennedy to confirm.
You: Ticket booked. I land Thursday afternoon. Let me know where to be.
Her reply comes a few minutes later, as concise and clinical as you expected.
Kennedy Brooks: Friday. 11am. North bench outside the Jerónimos Monastery. Don’t speak to me unless I speak first. Be clean. Be on time. And don’t give me your real name.
You stare at it for a moment, feeling a mix of tension and something close to admiration. She doesn’t waver. She doesn’t soften. She lays the terms out as plainly as the architecture you’ll be walking past on the way to her. This is a woman who knows exactly what she wants in all aspects of her life from the confessional to the bedroom and doesn't let other people's opinions interfere with it.
On impulse, you open the College Spread group chat. You know exactly how this is going to land, but that’s part of why you post it.
Fresher: FYI — I’m flying to Portugal.
The flood begins instantly.
Tank Marshall: BRO. BROOOOOO.
Cassie Li: You are not. You are actually crossing international lines for a challenge?
Milo Gutierrez: absolute lunatic energy! I approve... also I’m calling it now: Jet-Shagged. yes, it’s British. no, I don’t care. it’s perfect
Professor Rourke: I confess, I hadn’t anticipated international travel as a viable strategy.
Graham West: Just make sure you know what to say at customs. “Academic tourism. Special interest in contemplative architecture.”
Cassie Li: Honestly? If you pull this off, I’m buying you a coffee and a therapist.
Tank Marshall: Real talk though, that’s crazy respect.
Just don’t miss the Monday update. You miss the score lock-in, you get nothing but legend status.
Fresher: I’m not doing this to be a legend. I’m doing it because I drew the card. And I don’t fold.
Milo Gutierrez: either this is the hottest play of the game or the most expensive jerk-off in college history, either way, I’m lighting a candle for you
Fresher: Appreciate it.
You scroll for a moment longer, half expecting Rhett to chime in, but the host says nothing. You’re not sure if that means he’s quietly impressed or curled up laughing at the absurdity of it all.
The airport is ordinary. Your layover is long. You don’t sleep much.
But by the time you're sitting at the gate, backpack under your legs and the tablet powered down beside you, the nerves have mostly faded. Not because you’re at peace — just because you’ve committed. The decision is made, the wheels are turning, and all you have to do now is show up where she told you to be.
You’re flying across the Atlantic for a woman who doesn’t want your name, your history, or your voice.
And the strangest part is, it doesn’t feel strange anymore.
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College Spread: Sex Poker
Gambling With The Student Body
A freshman at college is invited to take part in a mysterious game. Not knowing what it is, he decides to give it a go, only to find he's volunteered for a poker-related gambling game where the more students (and faculty) you fuck, the better your odds of winning!
Updated on Jun 21, 2026
by Meaniehead
Created on May 18, 2025
by Meaniehead
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