You Bet Your Ass

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I won a bet with my roommate the hard way.
1.2k words
3.99
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There's nothing worse than two divorced guys sitting around watching television on a Saturday night. Lamar lost everything when his wife took everything he owned. All he had left after he got home from work that day was the car and the clothes he had on his back. I wasn't much better off. The only difference seemed to be in the bills that were left behind. In this department, I was the ultimate loser. Still I managed to get a tiny apartment behind an old house on the outskirts of town. When I found out Lamar's troubles, we decided to chip in together.

On this particular night, I didn't find much on television that excited me. In fact, I ready to head to bed. The window air conditioner was barely spitting out any cool air and I was drenched with sweat. Since we were both in jeans, it just became a matter of time before someone asked the awkward question.

"Dude," said Lamar, "What is wrong with that stupid air conditioner?"

"I don't think it worked since we the day we moved in," I said.

"I hate to say it," said Lamar, "But I got to lose the jeans."

"Okay," I said, tentatively.

Lamar chuckled.

"What's wrong?" asked Lamar, "Are you afraid of a black man's dick?"

With one raised eyebrow, I nodded. I found it strange that Lamar would ask such a thing. I knew Lamar exaggerated his sexual exploits to the guys at work. In fact, I didn't know many men who didn't stretch the truth somewhat when it came to sex. Since I wasn't much of a ladies man, I kept my mouth shut when the boys at worked talked about sex.

In fact, the last year or so was a disappointment. I had a feeling my wife had someone on the side, but I could never prove it. In fact, my wife made the past year a living hell. Her language had changed and I became of object of her anger and scorn. After a while, I actually looked forward to going to work. I did a great job of hiding the truth from everyone, but all the sleepless nights on the couch created bags under my eyes. Since there was never any money or food in the house, I started to lose weight at a dangerous rate. People were actually worried about me and how sickly I looked. When the truth came out about my wife leaving me, many people had already guessed at what had been happening all along.

"For all I know," I said, "You might have some twelve inch dick."

Lamar frowned.

"How did you know?" asked Lamar.

I put my hands up in protest.

"Hey," I said, "It was just a joke."

"What?" asked Lamar, "Are you looking in my pants while I sleep?"

Suddenly, I realized that Lamar was serious.

"Really?" I asked, "Is it really that big?"

Lamar nodded his head.

"Damn right," said Lamar, "That's why my wife left me."

"I didn't know that," I said.

My friend didn't look to happy about disclosing this to me.

"She couldn't handle it," said Lamar, "I don't know many women who can."

At that moment, the beer loosened my lips. Usually, I kept my mouth shut, but I was curious. I had never seen a penis that big. Sure, you could see penises in adult movies, but I never knew if they were real or just some fake prosthetic.

"Come on," I said, "You tell everyone at work that you get laid all the time."

"So?" asked Lamar.

"Maybe our wives left us because we were cheating on them?" I asked.

Lamar frowned.

"Maybe because you were sucking your boyfriend's dick," said Lamar.

By this time, I felt tipsy. The alcohol was making me braver by the minute. In a moment of stupidity, I stood up and dropped my trousers. Before Lamar could protest, I dropped my white briefs. My tiny penis became exposed to the flickering light of the television screen. I looked at Lamar and pointed to my penis.

"Do you really think a gay man would want anything to do with me?" I asked Lamar.

At first, Lamar stared at me. He was absolutely stunned at my exhibitionist behavior. In an act of defiance, I picked up my clothes and threw them into my bedroom. I tossed my shoes in the room for good measure. Speechless, Lamar watched me sit back down on the couch. It felt good to strip down to just a t-shirt. The heat of the night was oppressive.

"Dude," said Lamar, "You're almost naked."

I shrugged my shoulders.

"Relax," I said, "No one's come to visit us."

"You don't know that," said Lamar.

"You know what I think," I said, "I think you're bragging to everyone at work."

"What's that supposed to mean?" asked Lamar.

"If you really are a ladies man," I asked, "Where are all of your ladies?"

"Are you for real?" asked Lamar.

"You know what I think," I said, "I think your penis is no bigger than mine."

"Are you serious?" asked Lamar.

"Twenty bucks says you're gay and you've been waiting to fuck me up the ass," I said.

By this time, I didn't care. I had been so sick and tired of people lying to me. I had seen how Lamar looked at me when I was in the shower. There was a rumor at work that Lamar's wife was not happy with her husband's nocturnal activities. In a bold move, I decided to put Lamar to the test.

I turned around on the couch and presented my virgin ass to Lamar. I took my hands and spread my ass cheeks in front of Lamar's face. I wanted Lamar to know that I knew his secret. At first Lamar seemed embarrassed, so I laughed.

"I thought so," I said.

What happened next was a complete surprise. Without warning, I felt Lamar's lips on my exposed sphincter. My tiny penis sprang to life. The sensation was electric. To my surprise, Lamar's tongue was licked me between my ass cheeks. I froze. I could feel my penis swell.

"Oh crap," I said, "I was just kidding."

Before I could run, Lamar's big hands were around my waist. I didn't know it but he was already naked. How did he get his clothes off so fast? Before I could protest, Lamar's large penis was sliding into my ass. One of his hands covered my mouth so I could not scream.

To my surprise, the head of his penis was already inside. My fingers and toes started to tingle as his penis filled my anal cavity and touched all the right places. Breathlessly, I moved my ass towards him. I wanted to feel more and more of his engorged penis inside me.

"Is that what you want, white boy?" hissed Lamar.

I nodded as I moaned with excitement. I had never felt so out of control in my life. I could not believe that I was enjoying another man's penis in my rectum. I was shaking uncontrollably. My own penis was even erect from the excruciating pleasure.

After an eternity, Lamar slid out of my ass and turned me around. I came face to face with his large penis.

When it was all over, my face was covered with Lamar's sperm. My sphincter was raw and bleeding. My penis was pointing straight up in the air. I had ejaculated at least twice.

Lamar fished a twenty dollar bill out of his wallet threw it at me.

"Here's your twenty bucks," said Lamar.

"You really are gay," I said.

"You bet your ass," said Lamar.

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6 Comments
AnonymousAnonymousalmost 5 years ago
not even...

...that much of a start, as far as I'm concerned. Negative all the way, diminishing to absolute nothingness.

AnonymousAnonymousabout 7 years ago

there was good build up and a good start, but either you've never had anal sex, or you've only had not-good experiences, because the end is short, way too skimpy on the details, and totally unbelievable.

Go do your research (physical or digital) and have another go. You've potential.

63lsmith63lsmithalmost 8 years ago
NICE START

Not a lot of lead in and a real fast ending. Than being said I would like to see an other chapter.

Bambi_DoeBambi_Doealmost 8 years ago

Great start then you dropped the ball no details & the quick ending

animal7486animal7486almost 8 years ago
disappointing

this was a good story, all the way until it wasn't. Such a good start, but then there were no details. Not a bad story, just a disappointing one

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