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Dare Day

by Christophorus Volkov

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 27 Dec 2017

I bet I can cum before you!

There’s no way!

Carter had just laid down the gauntlet to Blaine. The two friends were close, nearly inseparable, and it had been that way since they were just boys. As they went through their teens, the hormones took over, and, even though they were straight, it became natural for them to mess around with each other.

Now, they never really gone too far with one another, but they would often make bets and dares of a sexual nature. The loser would have to pay with some sort of punishment. They called it Dare Day and it was usually after they got paid from working at the local pizza joint.

Carter had just turned 19, and he was a picture of young masculinity. Tall with a smooth, muscular body, he had been blessed with a long, thick, uncut cock that squirted cum violently. He had a few girls who were interested in him, but he remained a virgin.

Blaine was a bit more experienced even though he was about six weeks from his 19th birthday. He was shorter than Carter by a few centimeters, but he was firmly built and actually weighed a bit more than his taller friend. Like his body, Blaine’s cock was a fireplug. It was shorter than Carter’s, but it was a challenge for any of Blaine’s sex partners to take for very long because of its girth. When Blaine shot a load, the first few squirts would usually get airborne, but his cum mostly oozed out of his urethra.

Dare Day was usually at Carter’s. His parents both worked long hours, and even when they were home, they never bothered their only son. The boys would often go to the bank, get out some cash, grab a pizza from work and then hang out at Carter’s.

Carter’s room’s walls were covered with posters of football players and sports stars. Carter had once dreamed of a career in the NBA, but, with his size, he would have had to have been a guard. He just wasn’t that good of a ball handler. Blaine was a wrestler. He had done well at state his junior year, but his senior year slump cost him a scholarship offer. Now, he was just trying to save up some money to go to college in January. Carter had no plans at the moment.

The boys sat back to back on Carter’s floor as they usually did on a cum dare or bet. Carter would hit play on the old porn DVD he had. It was some old 1980’s era video that had been converted to DVD. He had bought it on sale at the town’s only adult movie store when he turned 18. He didn’t like the way the models looked in the video, but a pussy was a pussy he thought.

Carter’s parents were out at a dinner, so he turned up the volume loud. The girl in the video was almost squealing as the big-dicked top pounded her from behind. Carter loved the scene.

Blaine, on the other hand, would just close his eyes and think of the hottest girl he had fucked last summer in Florida. She had the biggest tits he’d ever seen, and her ass was big, sweet and round. Like the porn star in Carter’s video, he had made her take his thick cock from behind. He imagined the pleasure sounds emanating from the speakers were the sounds of the girl he fucked in Florida.

Carter lowered his shorts to his knees while glancing over his shoulder. He was looking to see if Blaine had cheated by starting first. Blaine still had his shorts up, but he was rubbing his cock through his clothes.

No touching until I say go, said Carter. He was always concerned about the rules.

Blaine was rubbing his already-hard cock, but he stopped when Carter caught him.

Man, I’m sorry. There’s just no way you’re going to beat me at beating off today. I’m so horny.

The talk excited Carter.

Why are you so horny? You been bangin’ that chick from the university again?

No, man. She’s old news. I’m not fucking anyone right now. You know that!

Yeah, I guess, answered Carter. I just forget things sometimes.

I know. You forgot the last time we did something like this, said Blaine, taking his shorts completely off. He was now naked. I smoked you.

That’s not happening today, said Carter. I’m going to shoot my load and make you lick it.


The boys liked to talk trash. The consequences of the dare or bet were never discussed ahead of time. The rules were always made clear before starting.

Ok, here are the rules, said Carter. No holds barred. First to cum wins, but you must complete your cum load before the other guy. Winner gets to name the consequences for the loser. If the loser refuses, he pays $500.

Blaine nodded.

You need lotion? asked Carter.

Yeah man. What do you have?

Carter stood up, and his shorts fell to the ground. His long hairless legs started from his narrow ankles and worked up to his thick calves and defined quads. He didn’t often miss leg day. Squats had built him a big, round, creamy ass with a deep crack in between. Blaine admired his buddy’s body.

Carter opened a drawer on his dresser and tossed the lotion to Blaine. He sat back down on the floor.

Blaine squirted out a generous amount of lotion onto his right hand and began to spread it on his hardening cock. This was considered preparation and was completely legal by the rules of the competition. When he was done, he handed the lotion to Carter. He knew Carter liked to start dry and then put lotion directly on the head of his cock before he came.

You ready, Blaine?

Yeah. Let’s go!


Carter started to stroke his cock. It was beginning to respond and was half hard when the green flag fell on the competition. Blaine, excited by the application of the lotion, had used the advantage of preparation to get his dick nearly fully erect.

He leaned back into Carter’s back. He loved to feel the warmth of his friend’s bare skin against his as he stroked. Blaine used a corkscrewing type motion on his thick member. He liked to run his entire hand up and down his thick shaft while twisting it. He closed his eyes and thought back to that evening in Florida.

Carter leaned back into Blaine as well. He glanced back and forth from the video action to the action behind him with his friend. He could barely see Blaine’s thick cock out of the corner of his eye. Carter stroked his cock using his left hand gripping with his little finger on his head and the thumb around the base. Usually, he stroked the shaft but, as he got closer, he would stroke the head of his long member with his right hand.

Blaine was hard to beat. He had tremendous control. He could cum fast or slow, and he could do it multiple times in a row. He and Carter had once done a bet to see who could cum the most times in a row without stopping. Blaine had prevailed with five-straight cums to Carter’s two.

As he corkscrewed his cock, Blaine also liked to tickle his hole. As this was a no holds barred match, he was free to reach down and rub his finger across his tight back door. He reached down, raised his thick balls, and placed his finger up his ass to the first knuckle. A wave of pleasure built from his loins through the rest of his body.

Carter felt him shaking, and he wondered if he was ok. He licked his lips as he watched the model get banged. He stroked harder and harder on his dry cock. Precum began to pour from his cock slit. He pulled his legs up, kicked off his shorts, and his felt his balls touch the wooden floor.

Blaine spread open his legs wide as he stroked and fondled his hole. The back of his neck was resting against the middle of Carter’s back. He could feel he was getting close.

Carter was also getting close. His gaze turned from the grainy video over his shoulder where he could see Blaine leaned up against him. He could see his big pecs and lightly haired chest. From the arm motion, he knew his friend was near cumming. It was time to get serious. Carter began to rub his chest and tickle his nipples.

The precum now was becoming its own lubricant for Blaine as he continued to corkscrew stroke his massively thick member. He knew he had reached the point of no return. Cum was imminent.

At the same time, Carter squirted out a bit of lotion and rubbed it on the head of his cock. He knew he was close too. His balls were moving upward in his scrotum, and that was usually his signal. The model continued to squeal on the porn as the big-dicked male porn star pulled his cock from her shaved pussy and slammed it up her ass. She cried, Fuck my ass! Fuck me!

Blaine’s balls nearly disappeared as they took their shooting position around the bottom of his shaft. With everything he had, he shoved his finger a little deeper in his hole.

Carter began to bite his lip. It wouldn’t be long now. He squeezed his right nipple...then his left while stroking only the head of his cock. He could feel his muscles inside his pelvis starting to spasm.

Blaine started to cum first. I’m...I...I’m CUMMING!

The first shot squirted out across his bare chest. The second one hit him between his powerful pecs. The third squirt covered his belly. The remainder of the shot oozed out of his cock and down his massive shaft. As he withdrew his finger, the massive member bobbed up and down still contracting from the intense cumload. The orgasm took over, and Blaine, now completely on the floor relaxed and let the wave fill his body.

Carter was even more turned on. He wanted to finish, and he did. Millieconds later, his cock roared to life.

UHHHH! Carter grunted as he began to shoot.

His first shot cleared him and landed over his shoulder on Blaine’s abs. The second squirt hit him in the face followed by three or four more squirts across his body. His cock continued to pour out thick, creamy cum as he laid back next to his friend.

The two boys didn’t say a word for a few minutes as they enjoyed the fruits of their labor: two amazing orgasms. The video had moved on as well to the next scene, but Carter didn’t really even notice. He was feeling too amazing from the orgasm. Blaine’s ears were ringing. Blaine broke the silence.

OH MY GOD! That was fucking amazing!

Carter answered, I know, right?

Blaine had won the bet. But, you know what? I won! BITCH!

Carter’s orgasm wouldn’t allow him to move a muscle. He barely could be heard. What’s my punishment? he moaned. His rippled abs were moving up and down in time with his heavy breathing. His own cum was splattered across his chest and stomach.

Blaine thought for a moment. He thought back to his Carter’s comment before the competition started about making him lick the cum off of him if he was victorious.

Do you trust me? asked Blaine.


Do you trust me?

Of course I trust you! I’m laying here naked with you!

Stand up.

Carter rose to his feet slowly. He was still buzzing from the orgasm.

Put your arms out to your side and close your eyes.

Carter’s long and cock throbbed up and down as a drop of cum oozed through the opening of his foreskin.

Blaine stuck out his tongue and began to lick the cum off of Carter’s abs and chest. He wanted to see what his friend’s cum tasted like in comparison to his own. Carter’s brand was a little sweeter than his own. It was a definite difference in taste. His skin was so smooth, and his ass felt great in his hand as he grabbed it while he was licking.

What are you doing? asked Carter.

I’m doing what you told me to do, BITCH!

I thought this was supposed to be a punishment, and you seem to be the bitch because you’re the one on your knees.

Blaine smiled. He knew that his friend would respond with a misogynistic comment. With his left hand, he reached up and grabbed Carter’s balls.

That’s a terrible thing to say, Carter. Apologize. go!

Apologize! Blaine said with a squeeze and a turn.

Carter grabbed Blaine’s wrist and tried to pull his hand off his balls, but the grip was too vice like.

Ap...apologize? For wha...what?

That comment. Do you think girls are supposed to be on their knees to serve you?


Do you? said Blaine with another squeeze and a twist.

Carter could barely talk through the pain. Involuntarily, his long cock started to harden again from the attention. Carter could get hard in the most inappropriate moments.! Ah! You’re reading too...uh...much into th...this! I’m sorry, man! Sorry! Just fuckin’ let go!

Blaine released his grip, and Carter fell to his knees. He grabbed a towel that had been laying nearby and cleaned himself off from the cumshot earlier. Carter was now in the fetal position on the floor, the pain in his balls rendering him unable to move temporarily.

Looking around the room for something to spank Carter with, Blaine saw his friend’s phone charger cord attached to the laptop in the room charging Carter’s phone. He put back on his briefs, and he walked over to the computer. He pulled the charger out from the USB port and Carter’s phone.

He looked back at his friend who was finally starting to unfold from the fetal position, Now, your ass is going to pay. Stand up.

Knowing the rules of Dare Day, Carter knew that he was completely under the control of his friend. It was either that or pay him $500, and he couldn’t afford it. Carter once again struggled to his feet with his balls still aching and cum dripping from his now completely hard cock.

Take a finger, lick it, and stick it in your hole, Blaine ordered.

You know I’ve never had anything up there.

I guess I should start counting my $500, then. LICK IT AND STICK IT!

Reluctantly, Carter put his index finger in his mouth. Blaine stood before him with his arms folded. When it was sufficiently wet, he reached around himself and started to put his finger in his hole. no no... said Blaine. I’m going to need to see this to believe it.

Carter turned around and bent over. Blaine reached over and spread his friend’s glutes apart revealing a hairless, tight asshole. It was the first time he had ever seen Carter’s hole before. Carter placed his wet finger against his hole and pushed it inside.

OW Man! yelled out Carter as his finger barely penetrated inside.

Blaine laughed. Oh, it’s not over. I’m going to have to see two knuckles.

What got into you today, man?

You pissed me off. Do it!

Carter pushed until he felt his finger moving into his body. It was only a few centimeters in diameter, but it felt like he was putting a knife up his virgin back door.

Carter pushed his finger in past the first knuckle. Finally, he reached the second knuckle.

Pull out, said Blaine.

Carter began slowly inching his finger out until his hole snapped shut as if his body said, NEVER AGAIN!

Now sniff your finger. I want you to smell your ass.

Carter put his finger up to his nose, and it smelled nothing like he thought it would. It was clean as a whistle. He figured it would be covered with last night’s dinner.

How does it smell?

It smells like my ass.

Blaine chuckled. His friend was standing with his back to him. His muscular legs, ass, and back in full view. Blaine grabbed Carter’s phone and took a picture of him.

You should see yourself! You’re fuckin’ hot! said Blaine. He handed the phone to Carter. Have you ever looked at yourself? Take a good look.

Carter grabbed the phone. He looked at his naked body.

What do you see? asked Blaine.

I see me.

Do you like what you see?

Um, that’s kind of a tough question.

Why is it so tough? I like myself.

What are you doing with all this? Carter wondered out loud. Why all this?

Just tell me what you see in the picture.

Carter paused and looked carefully, but he just saw himself. He shrugged and said, I see a tall, muscular, white dude with a banging ass and great legs.

Blaine smiled and said, I just wanted to see if you saw what I did. Now bend over.

Is this where you fuck me?

No. I don’t fuck friends. I’m gonna whip your ass though, so prepare.

Carter glumly bent over and put his palms on his bed. Blaine grabbed the phone charger cord.

Who’s your favorite soccer player? asked Blaine.

James Rodriguez, answered Carter.

He’s number 11, right?

Of course. You know that.

Eleven it is. Count ’em!

Glad you picked soccer and not the NFL, said Carter. His favorite player was J.J. Watt who wears number 99.

Blaine laughed. Here comes the first one. Count them out.















Blaine stopped for a moment and noticed that across his friend’s bare white ass that red wheals were starting to form.








The eleventh landed with an extra bit of mustard behind it. Carter’s elbows buckled, and he fell across his bed chest first with his ass pointed up.


Blaine admired his handiwork as Carter reached back with his hands to rub his ass. He’d been penetrated and had his ass whipped into submission. Carter’s ass hurt, and it hurt a lot.

We’re done...until next time, said Blaine, ominously.

You really did a number on me. You surprised me, said Carter.

Sorry if it went too far, but you pissed me off.

Well, you better hope you win the next time we do this or else your ass is going to bleed.

Blaine knew that he was probably safe, and he knew that he indeed had to win the next Dare Day or else Carter might have his revenge.

Carter slept naked on his stomach that night because it hurt too much to roll over. Blaine decided to stay over. He slept in his boxers on the floor next to Carter’s bed.

About 3:30 am, Carter woke up. Blaine was sound asleep on his stomach, and, when he slept, he slept heavily. Carter pulled down Blaine’s underwear. He lubed up his cock and stuck it between his friend’s cheeks. He had been pounding his friend for a good minute or two before Blaine woke up. Carter stopped for a moment. He really was groggy himself and didn’t really realize what he was doing fully as he thought he was pounding the girl in his dreams. When he realized it was Blaine, he was sure his friend would be mad, but, instead of being mad, Blaine started to push back against Carter’s cock by pushing his ass up off the floor.

Keep going, Carter.

Are you sure?

Yeah. You started this. Finish it.

It was just a few more minutes before Carter’s inexperienced cock blew its load deep into Blaine’s ass. With a satisfied grunt, Carter fell off his friend in a state of orgasm.

Blaine just laid there looking at his satisfied friend. He was happy to be there for him and be his first time. He loved Carter, but he couldn’t express it just yet. Maybe next Dare Day.

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