🌴 Tropical Permission 📖 Chapter Nine: The Roommate
An untold secret from James' past reveals the psychology of his present desire
This post will be available to EVERYONE at 6 pm ET, 7/23/25. Future chapters of Tropical Permission will be exclusively available to subscribers for the first 24 hours after they post. Thank you for reading! - L.H.
James stood at the railing outside the restaurant, Diane beside him, the surf pulsing below. He still hadn’t said it—not the whole truth, not his secret. But Diane’s hand found his, patient and warm.
Back in the villa, he poured them each a nightcap. She didn’t press him. She just waited. She knew her husband. Once he had resolved to say something, he would. Sometimes he needed time to gather his words.
They took their drinks in bed, with the lights out and the doors open, sounds of the breeze and the ocean provided a calming sonic ambiance. As they laid side by side in the darkness, James finally began to speak. His voice was barely above a whisper, but once he started, he didn’t stop.
—
I’m sure I’ve mentioned this before, but my roommate freshman year of college was an absolute nightmare. And I’ve only ever told half the story of why he was such a nightmare.
His name was Zack. Six feet tall, shaved head, maybe three shirts to his name. A complete animal. He was there on a wrestling scholarship and you took one look at the guy and just knew he was a savage on the mat.
His side of the room looked - and smelled - like an ecological disaster from within a week of us moving in together. I never saw him do laundry, or shower.
I was the opposite, obviously. My mother had drilled discipline into me: make your bed, fold your clothes, be decent to people. Zack had probably never made a bed in his life. Definitely not in the two semesters we bunked together.
It was clear from day one that this was not going to be the start of a new friendship. We were barely civil.
The first week of classes, he told me — dead serious — that he’d be bringing a lot of girls back to our dorm, and I had two options: play dead or disappear. “Don’t fuck it up for me, man,” he said. “This is what college is for.”
I didn’t believe him, but he meant it. Girls started showing up the second weekend. He’d slam the door open, lights on, music up, not a care in the world. Sometimes I was out—studying, or pretending to have a social life. I’d come back late and hear him loudly banging some girl and end up passing out in the hallway outside our room.
But a lot of the time, I was there. Lying in bed. Sleeping or pretending to be asleep. I could almost always hear them coming well before our room - Zack’s voice loud and cocksure, the girl’s laughter. So if I wasn’t sleeping I’d have time to get in bed and pretend.
And if I was actually sleeping, I’d almost certainly be woken up on his arrival. He didn’t care that I was there. He’d never whisper. He wanted me to hear.
I tried to ignore it at first. Closed my eyes, willed myself to sleep. But it was impossible. The sounds were too much. The wet smack of skin, the dirty things Zack would say, the girls gasping and moaning. They way they all, every single one of them, seemed amazed and enamored with how big his dick was. I tried turning away, but I’d find myself getting hard, biting my lip, hating myself, wanting more, wanting to see for myself how big he was.
Eventually, I started watching. Just a little, at first. Peeking from under the covers, heart in my throat. The room would be half-lit, Zack on top of some girl, or bent over her, or her riding him with her hair wild in the lamplight. I’d watch until I couldn’t take it, then jerk off quietly, desperate not to be noticed. But I knew — eventually I knew — he was doing it for me.
He’d lock eyes with me sometimes, just for a second, just long enough for me to know he knew I was awake. Sometimes he’d talk about me to the girl he was with. “You like getting fucked while my roommate’s sleeping a few feet away?” was a common one. Almost always followed by an enthusiastic, “yes! Keep going.” Or something like that.
We never spoke about it. Not once. I pretended every day that nothing was happening, and so did he. It went on for months. Sometimes I’d come home and he’d be alone, and I’d almost want to ask if he’d be having someone over that night. But I never did.
By spring, I’d met someone—a girl named Samantha. We started dating and I spent more nights at her place than in my own bed. By the time finals came around, I barely saw Zack. We both packed up on the same day. Didn’t even say goodbye.
I’ve never told anyone about it. Not my friends. Not Samantha. Not you. Until now.
—
James let the silence hang between them. The room felt heavier, smaller.
Diane reached over and took his hand, her grip steady, her thumb tracing slow circles along his palm. She could tell, recalling that experience hadn’t been easy. He still carried shame from those decades ago.
He had a look on his face that was braced for judgment, or worse, for pity.
But Diane’s voice was gentle, almost awed. “You’ve been carrying that for a long time.”
He nodded, his throat thick. “I don’t know what it means. I just… I think about it, sometimes. How much I liked it. How much it fucked with my head. I never felt more alive and ashamed at the same time.”
Diane squeezed his hand, then turned into him, pressing her body close. “I think you told me because you know it doesn’t scare me,” she said softly. “And because maybe it turns you on that it doesn’t scare me.”
He let out a shaky breath, relief and arousal tangled together. “Yeah. Maybe it does.”
Diane’s hand drifted lower, sliding under the sheet, her touch familiar but newly charged. “Maybe it turns me on too,” she whispered, mouth close enough to his ear that he could feel her hot breath. “Tell me what you’re thinking about right now.”
Her hands found what they were searching for, fully erect. James closed his eyes and sighed at her gentle touch.
His voice was hoarse. “You know.”
She freed him from his boxer briefs and wrapped her palm around him. “Tell me.” She started stroking.
“You. Bent over. Getting fucked by Zack.”
She sat up. Pulled her shirt over her head and straddled him in silence, facing away, the way she knew he liked. She reached between her legs and guided him in, sinking down slowly, deliberately.
“Watch my ass move,” she said, her voice velvet, in command.
He groaned, hands gripping her hips.
“Hands off. Just lay back and watch,” another velvety command.
“Just watch and imagine it’s not your cock I’m riding,” she whispered. “Imagine it’s his. Bigger. Thicker. He wants to ruin me. And he wants you to watch.”
James cursed under his breath. His hips bucked.
“Imagine how I’d moan,” she said, grinding down harder. “How I’d beg him for more. How wet I’d be. For someone who isn’t you.”
He couldn’t speak.
Diane kept moving, head tilted back, palms on his thighs.
“Can you see it?” she whispered. “Can you see him fucking your wife?”
Lower, “Can you see that big dick using my pussy?”
James came with a strangled sound, hips jerking beneath her.
She kept riding him. She was thinking about what another man would feel like inside her. Thinking about James watching her in the ecstasy of a stranger.
When she finally came—slow and shuddering—she collapsed backwards onto his chest, and rolled onto the pillow next to him, breathless and grinning.
Neither of them said a word for a long time.
But something had shifted again.
The momentum, she realized, felt unstoppable now.
Like the slow burn of Tropical Permission but sometimes need a quicker hit of erotica? Check out my first three hotwife-themed short stories:
Hi Lydia. I’ve been enjoying the series through chapter 9 thus far. I am not yet a paid subscriber, and I would absolutely consider paying, but just want to confirm that that’s necessary to continue this series. I cannot access chapters 10 or 11 right now without becoming a paid subscriber. Chapter 10 says it will be posted for free as of yesterday (7/25) at 4 PM, however, it is not yet available. Perhaps I’m doing something wrong. Many thanks.