Day 4: Kennedy (Arriving in Portugal)

You land in Lisbon around four in the afternoon, local time. The air is clean and warm, the sun angled low enough to throw long shadows across the tile floors of the terminal. You feel like you’ve been folded into a suitcase yourself—dry-eyed, exhausted, and already a half-step behind your own thoughts.

As you move with the crowd toward passport control, your brain keeps circling back to the same question: what the hell are you doing here? Not as a moral panic—just logistical disbelief. A few weeks ago you would never have considered anything like this. Now? You wonder if you've found a new adventurous aspect of yourself you hadn't experienced before or if you're already becoming a totally different person. Well, you think, they say college changes you.

The customs officer flips through your passport without looking up. His voice is neutral, practiced.

“Purpose of visit?”

You answer automatically. “Tourism. The monastery.”

He raises an eyebrow. “You came alone?”

You nod. “Yes.”

His eyes narrow slightly as he looks at the return date on your paperwork. “You fly from America for just two days?”

The words sound even more ridiculous when he says them aloud. “Yeah. I have class Monday.”

His gaze lingers on your face. “Two days is barely enough to recover from the flight. What do you plan to see?”

“I’m a philosophy major,” you reply, forcing a tone that sounds like enthusiasm. “We were studying Jerónimos. It came up in class. I thought it’d be worth seeing in person.”

The officer stares at you skeptically, then he stamps your entry with a kind of tired resignation. “Don’t miss your return flight,” he says, sliding your passport back across the desk.

You murmur thanks and move on, not quite sure whether you just passed a test or simply bored him into compliance.

The hotel is modest, clean, and blessedly quiet. You take a narrow lift to a third-floor room that overlooks a small internal courtyard filled with ferns and cracked paving stones. The window lets in a soft golden light, and the bed looks far too comfortable for what this trip is about.

You don’t bother unpacking. Your bag goes on the chair, your tablet and charger onto the desk. For a while, you sit on the edge of the bed with your elbows on your knees, letting your shoulders sag under the weight of too much travel and too little clarity.

Eventually, you remember the instruction: Message me when you land.

You tap out a quick note to Kennedy, nothing elaborate.

You: Landed and checked in.

Her reply arrives two minutes later, as if she were expecting you to be punctual.

Kennedy Brooks: You actually came? Ok, change of plan. There’s a place nearby. Clean, discreet. Private booth with a glory hole. Here's the address.

You reread it, then blink a few times just to make sure you didn’t hallucinate it somewhere between jet lag and disbelief. It's an adult store in the center of the city, enough of a trip from the monastery that Kennedy probably won't run into someone from her retreat. You're kind of amazed she even found it.

You: Wait—you came to Portugal for a religious retreat and still found a glory hole?

Kennedy Brooks: I’ve been coming here for years and never noticed it. I could’ve been having SO much more fun.

You stare at the screen for a second longer, letting that sink in. Of course she found one. Of course she would rather use a literal wall than risk eye contact. This isn’t a workaround for her—it’s an upgrade.

You: I have to record it, or it doesn’t count.

Kennedy Brooks: Film your side. I’ll message Rhett myself. He’ll confirm it's me. You’ll get your challenge. And I’ll get what I want.

You set the tablet down and lean back against the wall, unsure if you’re impressed or just stunned. It’s the most Kennedy solution imaginable: cleaner than contact, colder than conversation, and efficient in ways that almost terrify you.

With nothing else to do and nowhere to go, you flick open your contacts to call Kailani. That's something else that hits you as a major change. Until you started this game, the concept of a sadomasochistic dominatrix cam girl would never have occurred to you. Now you can't think of anyone you'd rather call. In such a short time she's become your friend, your rock and, potentially, a source of occasional income.

She picks up on the second ring, lounging on her couch with one leg draped over the armrest and a mug balanced on her stomach. When she sees your face, she squints.

“Okay, hold up. That is not your dorm room.”

“Lisbon,” you say. “Hotel. I got here this afternoon.”

She blinks. “Wait—Lisbon Lisbon? Portugal Lisbon?”

“Yeah. It was the only way to complete this week’s challenge.”

She stares for a long moment, then lets out a slow whistle. “Damn. I zap your dick once and suddenly you’re booking international flights. I really did break you.”

“You helped. I had the money. You gave me momentum.”

“So I’m a kinky catalyst. I can live with that.”

You pause, then add, “Seriously. Thank you. If you hadn’t thrown me headfirst into a live show, I’d probably still be sitting on campus wondering what to do.”

"So who's the girl?"

You pause, not really wanting to hide anything from Kailani but... "I'd rather not say, if that's ok. She's into anonymous sex. It feels like I should keep her anonymous."

Kailani nods. "Cool, I can appreciate that. Like I said, you're a decent guy... for a perve!"

"Pot meet kettle," you laugh. "Anyhow, my anonymous sex lover was on a religious retreat for a week over here so I had to come or lose the challenge."

She makes a face and waggles her fingers. “Blessings upon your confused little soul.”

You hesitate a moment, then drop the bomb. “She found a glory hole.”

Kailani stops breathing for a full second. “She what?”

“She messaged me. Said there’s a booth nearby. Clean, discreet. Challenge will happen there.”

Kailani’s eyes widen as she tries and fails to speak. Finally, she just cackles and nearly spills her drink.

“Oh my god. She found a glory hole during a religious retreat. I—okay, I respect that. That’s actually amazing. Terrifying, but amazing.”

“That's what I said!" you tell her. "She’s efficient."

“She’s a Bond villain,” she replies. “With hymns.”

The laughter fades to a grin. “Good luck, Day Stripper. Make it weird.”

“You know I will.”

After the call ends, you shower, plug in your tablet, and stretch out on the bed with the alarm already set. You don’t close the curtains. You don’t even pull the blanket over yourself. You just lie there, letting the silence settle in around you like thick wool.

Tomorrow, at eleven in the morning, you’ll meet someone who already made her boundaries clear: no contact, no conversation, no names. Just a stranger, a wall, and the unblinking eye of a camera.