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Cleveland Cassidy's Massive Dick

If ever there was a cautionary tale to be careful what you wished for...

Oh who am I kidding? Like I expect you to understand my burden.

Cleveland Cassidy’s Massive Dick by Nathaniel Tower



His dick was the size of a racehorse. Not the size of a racehorse’s dick. The size of an actual full-grown racehorse.

When Cleveland Cassidy was born, the first thing the doctor said was, “Congratulations, Mr. and Mrs. Cassidy. You have a son with a very large dick.”

The nurses in the room swooned. One even had a mini-orgasm.

Mrs. Cassidy, covered in sweat, tears, placenta and feces, passed out when she saw the appendage.

Mr. Cassidy, a bit jealous, asked, “Is it normal for a baby to have a bigger dick than his dad?” His own dick, the size of a dog’s, shrunk in the presence of the baby’s massive dick.

“No, I assure you, this is far from normal,” the doctor said with admiration.

“Is there anything we should do?”

“Keep him away from porn.”

It had been a blessing at first. A great conversational piece, a way to show up all the guys, a way to drive all the ladies wild. It grew at the same rate as his body for the first few years, but once he hit puberty, it seemed to expand exponentially.

By the time it stopped growing, at the age of eighteen, Cleveland Cassidy’s dick was the size of Man O War. There was literally nothing he could do with it.

“Mr. Cassidy,” the doctor told him before he came of age, “you must never get an erection. You will die instantly.”

Prior to this warning, he had never even thought to get an erection. Nothing had quite been grand enough to warrant such a flow of blood.

“Is it even possible?” he asked the doctor.

The doctor pondered the question long after Cleveland left the office. 

In school they watched a video on Elephantiasis. Cleveland began to feel like a freak. He went back to the doctor.

“Do I have Elephantiasis?”

“No, you just have a massive dick.”

“But there must be something wrong with me,” Cleveland insisted, his large genitalia staring at the doctor.

“Nope. You just have what all men wish for.”

“Do you wish you had a dick like this?” Cleveland tried to lift it as he spoke, but his arms were tired from carrying the member up the stairs to the doctor’s office.

“No, of course not. It looks quite inconvenient actually. I simply meant that you possess what all men dream of having, but they don’t really understand what they are dreaming about. There isn’t even the remote possibility that you could ever have sex. Even the largest vagina in the world couldn’t accommodate a tenth of your dick. You’ll never even have an orgasm.”

As Cleveland drove home from the doctor, his dick riding shotgun, he vowed he would have sex one day just to spite the doctor. Surely there was a vagina that could handle his racehorse dick. If he could have such a dick, someone could have such a vagina.

Cleveland spent hours staring at naked pictures of women on the computer. When the pictures did nothing to stir his dick, he tried some videos. He began with solo girls, then moved to girl-on-girl before finally graduating to videos of hardcore sex. He tried to imagine himself having sex with the girls, but all he could do was laugh at how small all of the dicks were. Staring at the tiny dicks that penetrated the women’s tiny vaginas, he imagined how something equal to the size of his entire body would have a chance of fitting inside someone.

Years went by. Cleveland spent a little time each day watching porn hoping for even the slightest hint of an erection. Still nothing moved. When he had exhausted every possible outlet for sexual fantasies, he gave up. The good doctor was right. Cleveland decided to go about living a normal life as best he could, graduating from school and getting a job at an office. He was supplied with an extra large cubicle to accommodate his disability. 

Many years later, at the ripe old age of sixty-seven, Cleveland Cassidy, a permanent bachelor, contemplated retirement. Everyone had waited for this day with bated breath, hoping they could swoop in and get the large cubicle. “Aren’t you ever going to retire?” they would constantly hound him. He didn’t see any point. There was nothing waiting for him at home except for the empty promises of unsatisfying pornography.

As he approached his boss’s office, the new secretary smiled and said, “Hi Cleveland.” Then she placed a jumbo Sharpie in her mouth. Cleveland felt a twinge and tried to waddle quickly past her.

“Howdy, ma’m,” he responded with a nod of his head. 

“How are you today?” she managed to ask with the entire Sharpie in her mouth.

“Well, I’m just fine. I’m on my way to re…” He hesitated before finishing the sentence. Watching this woman devour a massive marker gave him a feeling he had never quite had before. So long ago he had given up the dream of even achieving an erection, but here he was, a sixty-seven year old man long overdue for retirement, his massive dick held firmly in his hands. Perhaps retirement was a mistake. Perhaps he had wound up at this office for thirty-nine years for some profound purpose, and that purpose was about to be fulfilled by this marker-swallowing nymphomaniac.

“Would you like me to help you with that?” she said, pointing to the retirement letter he held sandwiched between his hand and his dick.

He nodded and she reached for the letter, her hand slipping and grabbing a tiny piece of his dick. The moment was brief, but it brought him more joy than he had experienced in his sixty-seven years on Earth.

The life insurance check barely covered the cost of the two plots required for his burial.


Nathaniel Tower lives in the Twin Cities area with his wife and daughters. His fiction has appeared in over two hundred online and print journals. Nathaniel is the founding and managing editor of Bartleby Snopes Literary Magazine and Press. When he’s not doing writerly things, he likes to joggle (juggle and run simultaneously). He is the former world record holder for running a mile backwards while juggling. He is working on getting his record back. Find out more at nathanieltower.com.