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MyJockStrap

A Backfiring Bet


It was a cold winter night. A few friends had gathered at my place to watch a ball game. We had drunk a couple of beers each and we were looking for something to do. The game was due to start in an hour or so. Suddenly, an idea came to my mind.

"Let's play truth or dare," I said triumphantly.

"Good idea!" Chris said and the other two guys, Pete and Paul, agreed.

Chris was a tall, athletic guy and a great gambler as well. After a few rounds it was his turn to play.

"Truth or dare?" Paul asked.

"I dare!" Chris said really sure of himself.

"Well, I dare you to take off your clothes and stand in front of the window showing off your butt to the neighbors," Paul said.

"Brilliant idea!" Pete exclaimed.

"I bet you won't dare to!" I said smiling.

"Want a bet?" Chris asked really excited.

"You're on!" I answered. "I bet my ass you're not gonna make it!' I said decisively.

"It's a deal!" Chris said and he seemed to be really determined.

Right away, he took off his shirt and his pants.

"Go all the way!" Pete shouted.

"I sure am!" Chris answered.

Instantly, he pulled down his briefs revealing a long, thick cock with two large balls. He moved to the window, drew the curtain and stuck his butt on the windowpane where everyone could see it. He was really turned on by his voyeurism; his dick grew a few inches more. It was now a real monster made of flesh threatening every asshole in the room. While the neighbors were enjoying the view from our window, I realized that it wasn't such a good idea to put my ass on the line.

Five minutes later, Chris withdrew from the window. He had won the bet and I had to pay him.

"It's time to pay your debts, Frank," Pete said.

I couldn't refuse, I had to keep my word; however, I had a plan that could save me from an ugly situation.

"Well, a bet's a bet, guys," I said. "Let's go to the bedroom, Chris," I urged him.

Chris followed me to the bedroom without even getting dressed.

"Look, Chris, this whole thing was just a joke. But I think I've found a way to keep my end of the bargain. I'll give you a blowjob and we'll call it even. It will be our little secret!" I said.

"All right!" he said.

I thought that he wasn't interested in my ass after all but I was mistaken. Chris had a plan of his own. I took off my shirt and my pants and kneeled down.

"Go on, suck my cock, Frank!" Chris said lustfully.

I grabbed his rod and jerked it off licking his balls. Then I sucked each one of them. My mouth was full and he was rubbing his tool all over my face.

"Take it in your mouth, Frank!" Chris urged me.

I obeyed taking his cockhead in my mouth and sucking as hard as I could. But Chris wanted more than that. He grabbed my head and forced it on his shaft, making me swallow the whole thing. I almost choked as his dick hit the back of my throat. He started fucking my mouth really hard. My lips touched his pubic hair and his large balls slapped against my chin. His rod came in and out several times. Chris would pull out rubbing his thick tool on my lips and I would place it on my tongue licking his peehole. Then, he would slap my tongue with his cock driving it back inside my mouth deeper than before. I sucked his red cockhead looking at him and making loud slurping sounds.

"You like it, don't you, you little cocksusker!" he said smiling.

"Mmm...I love your big, hard shaft, Chris!" I muttered.

"Don't speak with your mouth full!" Chris said laughing and shoving his phallus in the utter depths of my mouth.

Suddenly, he pulled out. It seemed to me a bit strange that he didn't cum but I didn't care. I thought that it was all over and I tried to get up but Chris pushed me back on the floor.

"Where do you think you're going, cumslut?" he asked infuriated.

"I thought we had a deal!" I yelled angrily.

"You should have thought of that before putting your ass on the line!" he said decisively. "Now, turn around and lie on all fours!" he ordered me.

I knew what was going to happen but I couldn't resist. Chris was no match for me physically speaking. He could rape me whenever he wanted and now seemed to be the perfect time for him.

I obeyed to his orders. I turned around and standing on my hands and knees I begged him not to rape my ass.

"Please, Chris! It was just a stupid bet. I didn't mean what I said. Don't fuck me, please!" I said urging him to stop.

But Chris shoved my head to the floor, making my butt rise at the height of his fully erected cock. Then, with one violent move he ripped off my briefs. As his cock-head touched my asshole I made my final plea.

"I'm begging you, Chris! Don't do it. I'm a virgin!" I said whining but that was a big turn on for Chris. He was determined to take me and knowing that I was a virgin he became eager as hell to fuck my ass.

"Well, I'll make this a night to remember, bitch! You can kiss your virgin hole goodbye!" he said laughing and groping my defenseless ass.

"No, don't..." I screamed but before I finished my phrase Chris pushed his cockhead in my asshole.

"How does it feel, you little whore?" Chris yelled really excited.

"It hurts, Chris!" I said. The pain was tremendous as his unlubed cockhead penetrated my virgin hole.

"Shut up and take it like a real man!" Chris moaned and with one mighty thrust he shoved the full length of his dick in my tight ass.

"Yeah, it's as tight as I thought!" he uttered triumphantly and he started fucking me really hard. He pounded my hole again and again, tearing me apart.

"You're hurting me, Chris! Stop! I'll do anything!" I screamed.

But there was nothing else that he wanted me to do. All he needed was my tight butt and my screams were just another aphrodisiac for him. Chris was so horny that each thrust was now accompanied by a hard spank on my ass. His thick shaft was stretching my hole to the limit. My cheeks had turned red from the spanking but he was unstoppable. He was sodomizing me and he was enjoying every single minute of it.

He had developed a powerful rhythm. Each thrust was harder than the previous one. As time went by his anal attacks became faster. What is more, his tool would go deeper each time. Just as I thought that I could take it, he would give me a more vigorous thrust ruining my once-tight asshole.

"Shake your ass, bitch!" Chris ordered me, squeezing my cheeks and pounding my butt mercilessly.

I obeyed pushing backwards and feeling his balls punching against my ass. I couldn't believe that another man had pierced my virgin asshole with his monstrous rod. The least I could do now was to beg him not to cum inside me. I hoped that he would save me from this last humiliation but I was mistaken once more.

"Please don't cum inside me, Chris!" I begged him.

"I'm going to fill your hole with cum, bitch! You can count on it, cumbucket!"

Chris grabbed my waist with both hands and started fucking me more intensely than before. His hard cock ravaged my butt again and again...

"I'm gonna cum, bitch!" Chris screamed pounding my ass as his cock exploded spurting several blasts of white cream inside my tight hole. I collapsed on the floor. Chris kept fucking me with his still-hard rod. A few moments later, he pulled out and kneeled in front of me; my nightmare was not over yet. He lifted my head up and rubbed his cockhead on my face smearing it with cum. Then, he forced me to open my mouth for a brief oral service. I sucked the last drops of cum from his cock.

"Suck me off, cumslut!" he said grinning. Finally, he slapped me a couple of times with his long shaft and said:

"Next time you want to bet your ass on something, call me! I'm always looking for a tight asshole to fuck!"

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