Funny stories in under 500 words.

Jerry's Plan



The view of the weathered, jagged mountains across the way always put Jerry in a contemplative mood. He sat at his desk—taking in the wonders of nature—like he did every night, reflecting on how everything had turned out. He was also waiting for the unmistakable sound of her voice, the signal to free his mind and hop eagerly into bed. For now, however, it all continued to play through his head, as if he was watching some tattered, old videotape.

He had planned it all for weeks, to the finest detail. He had to; nothing else had worked. He had been fed up with his dire financial situation and, as a result, embarked on a journey of desperation. This particular journey had him in the bowels of raunchy psychic shops, offering what pathetic pocket change he could muster for the day’s winning lottery numbers. His efforts there left him with a heavy heart, and an even heavier hand, as the small printed numbers on his tickets failed to achieve.

Then there was the three-day period he stood in front of the zoo’s main entrance, an open suitcase propped up beside him, as he attempted to caress the ears of the unassuming pedestrian with his opera singing. His gig was up when a woman walking past reached into the shrubs behind him and yanked out an old cassette player, the resounding voice of Mario Lanza ending abruptly as she whacked him in the head with it.

He didn’t quit there, though. Jerry, man of many trades, decided to go all out on the next one. He grabbed an old sport coat and a pair of slacks from the closet, sloshed them around in mud and beer, put them on, and proceeded to stand on the freeway ramp. He was even equipped with the unoriginal cardboard sign, holding it up for the hundreds of stone-faced drivers that passed him daily.

Four days of that endeavor left him with a bad sunburn, a bag full of cigarettes he wasn’t going to smoke, and a foot that had been driven over at least twice. No thank you.

Then there was the big one; the plan he had pulled off so nicely. He finally had the cash in his hands. No more student loans, no more stress about bills, no mor—

A woman’s voice decorated the air gently behind him.

“Ready for bed?”

Oh yes, he was quite ready for bed. There was her voice, right on time.

He rose from his desk, clicking off the small lamp in the process. He was certainly going to enjoy this. He unbuttoned his shirt and swiftly threw himself under the covers.

“Goodnight, warden.”

“Goodnight, Jerry. See you again tomorrow for lights out.”

Jerry listened to the warden’s footsteps growing more distant as he shut his eyes and thought of his eventual escape.

He had a plan…

This story was written by Louis Sisto, who was born and raised in Chicago, IL. He has been writing short stories and flash fiction for years as a personal hobby. He is hoping to one day begin working on his first novel. His previous publications include flash fiction and short story pieces on the Funny In Five Hundred website, Slattery’s Art of Horror magazine and www.winamop.com.




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