The prison bus rattled along the highway under a gray, indifferent sky, carrying three men toward the same destination and three very different versions of regret. The engine groaned with every mile, the metal benches vibrated beneath them, and the smell of diesel mixed with stale coffee and resignation. None of them spoke at first. Each man sat with his thoughts, aware that whatever life had been before this moment was now sealed off behind steel doors and razor wire.

As part of the intake process, they’d been granted one small mercy. Each prisoner was allowed to bring a single personal item—something harmless, something that could pass the time in a place where time had a way of stretching endlessly. That small allowance suddenly felt far more important than it had when the paperwork was signed.

The silence broke when the man sitting nearest the aisle shifted and glanced at the others. He was lean, sharp-eyed, the kind of person who looked like he’d always had a plan, even when things went wrong.

“So,” he said casually, as if they were strangers on a long road trip instead of inmates on their way to prison, “what did you bring?”

The man beside him, older and broader, reached down and pulled a small cardboard box onto his lap. He opened it carefully, revealing neatly arranged tubes of paint and a set of brushes worn soft with use.

“I brought paints,” he said, with surprising pride. “Figure I’ll paint anything they let me. Walls, rocks, scrap wood, whatever. Might as well come out of this with something to show for it. Who knows? Maybe I’ll be the Grandma Moses of cell block D.”

He chuckled at his own joke, then turned to the first man. “What about you?”

The first man reached into his bag and produced a deck of cards, flicking it between his fingers with practiced ease. He grinned, the kind of grin that suggested he’d won more than he’d lost in life—even when losing landed him here.

“Cards,” he said. “Poker, solitaire, gin rummy, blackjack. There are about a hundred games you can play if you’ve got time. And trust me, I’ll have time.”

They both turned to the third man.

He’d been quiet the whole ride, leaning back with his arms folded, a slow, satisfied smile stretched across his face. He looked entirely too pleased for someone heading to prison.

The painter raised an eyebrow. “Alright, what’s with you? You’ve been grinning since we left. What did you bring?”

The third man reached into his bag and pulled out a box. He held it up like a prize.

Tampons.

The other two stared at him, waiting for the punchline.

“You serious?” the card player asked. “What are you supposed to do with those?”

The third man didn’t answer right away. He just smiled wider, tapped the side of the box, and said, “According to the instructions, I can go horseback riding, swimming, roller-skating, and pretty much live my best life.”

For a moment, there was silence. Then the bus filled with laughter so loud even the driver glanced in the mirror.

By the time the gates swallowed them whole and the bus rolled back out, that laugh was the last moment of genuine freedom they felt that day.

Prison life settled in fast.

Days blurred together, stitched together by routines that never changed. Count. Meals. Work assignments. Lights out. Repeat. For the first-timers, the hardest part wasn’t the confinement—it was learning how everything worked without asking too many questions.

One man learned quickly that prison had its own strange culture, its own language, and its own brand of humor.

His first night was the worst.

The lights in the cell block snapped off all at once, plunging the long corridor into darkness broken only by thin slashes of moonlight through narrow windows. The air was thick with whispered conversations, the clink of metal bunks, and the distant echo of someone coughing two cells down.

Just as he was starting to drift, a voice rang out.

“Number twelve!”

Laughter exploded across the cell block. Men slapped bunks, wheezed, hooted, and howled like they’d just heard the funniest thing in the world.

The new guy sat up, confused.

A few minutes later, another voice shouted, “Number four!”

The laughter came again—just as loud, just as uncontrollable.

“What the hell?” the new guy muttered.

He turned to his cellmate, an older inmate with a face carved by time and experience, already settled comfortably on his bunk.

“What’s going on?” the new guy asked. “Why are they yelling numbers?”

The older man smiled faintly. “We’ve all been here a long time,” he said. “Long enough that everyone knows the same jokes. So instead of telling them over and over, we just number them. Saves time.”

The new guy frowned. “So they yell a number, and everyone just… knows the joke?”

“Exactly.”

The new guy leaned back, processing this. He listened as someone down the block chuckled quietly, like they were replaying the joke in their head.

After a moment, an idea sparked.

If it was really that simple, how hard could it be?

He waited for a pause, then stood up and stepped toward the bars. Clearing his throat, he shouted with confidence, “Number twenty-nine!”

For half a second, nothing happened.

Then the cell block erupted.

This time, it was chaos. Men fell off bunks. Someone was laughing so hard he was gasping for air. A guard down the hall shouted for quiet. Someone else laughed even harder at that.

The noise rolled through the block like a wave, louder and longer than before.

The new guy stood there, stunned, a little proud and completely confused.

When the laughter finally faded into exhausted snorts and chuckles, he turned back to his cellmate.

“I don’t get it,” he said. “Why was that one so funny?”

The older man wiped tears from his eyes and shook his head.

“We’d never heard that one before.”

And just like that, the new guy understood prison humor better than any orientation manual could explain it.

Life inside didn’t suddenly become easy. It was still loud, cramped, repetitive, and unforgiving. But humor—dark, absurd, and often ridiculous—became a kind of currency. A way to remind yourself you were still human in a place designed to strip that away.

The man with the paints eventually did become known for his work, covering scraps of wood with landscapes no one had seen in years. The card player ran games that passed long nights with the shuffle of a deck and quiet bets made of favors instead of money. And the guy with the tampons never stopped smiling, even when nothing else made sense.

Because sometimes, the only freedom left is how you choose to laugh.