Three newly convicted men sat quietly on a prison transport bus, staring out the windows as the reality of their sentences slowly sank in. The ride was long, uncomfortable, and filled with nervous silence—the kind that makes every minute feel like an hour.
To distract themselves from the looming boredom of prison life, the men began chatting about how they planned to pass the endless hours behind bars. Luckily, each of them had been allowed to bring one personal item to help keep themselves occupied during incarceration.
After a while, one man leaned forward and broke the silence.
“So,” he asked casually, “what did you bring with you?”
The second man smiled proudly and opened his bag, revealing a neatly organized box filled with paints, brushes, and small canvases.
“I’m going to paint,” he said with excitement. “Landscapes, portraits, abstract art—anything I can think of. By the time I’m done, I’ll be the Picasso of prison… or maybe the Grandma Moses of cell block C.”
The first man chuckled. “That’s impressive,” he said, before pulling out his own item—a worn but well-loved deck of cards.
“Cards are all I need,” he explained. “Poker, solitaire, blackjack, gin rummy. I’ll never be bored.”
The two men then noticed something odd.
The third prisoner hadn’t said a word the entire time. He just sat there with a smug little grin on his face.
“What’s with the smile?” they asked. “What did you bring?”
Without saying a word, the third man reached into his bag and pulled out a box of tampons, holding it up proudly.
The other two stared at him in disbelief.
“Tampons?” one finally asked. “What on earth are you going to do with those in prison?”
The man turned the box around, pointed at the printed instructions, and grinned even wider.
“Well,” he said, “according to this, I can go horseback riding, swimming, hiking, roller-skating… and pretty much anything I want.”
A Second Prison Joke That Makes It Even Better
In another prison, a man was locked up for the very first time. That night, as the lights went out, an eerie silence settled over the cell block.
Suddenly, someone shouted, “Number twelve!”
The entire cell block erupted in laughter. Prisoners banged on walls, howled, and laughed uncontrollably.
A few moments later, another voice yelled, “Number four!”
Once again, the laughter thundered through the prison.
Completely confused, the new inmate leaned over to his cellmate and whispered,
“What’s going on?”
The older prisoner chuckled. “We’ve all been here so long, we know the jokes by heart. So instead of telling them, we just shout the number.”
Wanting to fit in, the new guy stepped up confidently, cleared his throat, and shouted,
“Number twenty-nine!”
The prison exploded with laughter like never before. Men doubled over, tears streamed down faces, and some even collapsed onto the floor.
When the laughter finally died down, the new prisoner asked, stunned,
“Why was that one so funny?”
The old inmate wiped his eyes and said,
“Oh… we’d never heard that one before.”
