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The Dare

The Dare

by Samstone496
19 min read
3.58 (12400 views)
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The Dare

Annie had finally made time to meet up with her old friend Calvin. He brought his longtime friend along, Damon, who had a notorious reputation for being rambunctious on a night out. Noticeably absent was Rod, her husband. He had come out with her on these nights before, tonight was just not one of those nights.

"Where's Big Rod tonight? Hot Rod!" The guys shouted while they asked.

Annie's husband was a big, burley and handsome man. Annie offered no more than just saying he didn't feel up to coming out.

"He just doesn't like you hanging out with me because I have a bigger cock than him." Calvin blurted out.

This was the precise brand of crassness she was used to. This particularly special brand, usually only comes out after a few beers. She pointed that out to him. At that time, it also seemed appropriate to reveal the real reason for her husband's absence.

"Roddy thinks you're an asshole, and besides, you don't know that you're bigger, and I highly doubt it!...full of yourself much?!"

Damon chimed in;

"Jeez dude, no one wants to talk about whatever you got going on down there, get over yourself."

They laughed off the usual buffoonery of "buzzed" Calvin. Annie took a long swig from her pint to wash that thought away. But Calvin wasn't done.

"No, you're right, I wouldn't know who is bigger, but you would."

She gasped and sprayed beer across the table. Damon leaned in, suddenly realizing he had a front row seat for a great show. The two stared at each other, a menacing grin creeping across Calvins face. Annie, eyes rolling at Calvins constant ribbing, stared back, contemplating her response carefully. Calvin was relentless, which as a younger woman, she believed was part of his charm.

She had to admit he was actually correct, although she wished he hadnt revealed that detail in front of anyone. That was a secret she would have taken to the grave, apparently he didn't feel the same. Calvin was referring to the one and only night, years ago, before she was engaged to Rod, when him and Annie let themselves be more than just friends. It never happened again after that, and they never speak of it. At least never until now.

She was a little shocked and momentarily left a bit dumbfounded. Seeing Annie at a lost for words, and Calvin's beaming smile, Damon broke the silence.

"Annie is actually thinking about C's dick right now!" He basked in his discovery. It was a fact, that given the situation was also technically correct, but certainly wouldn't have been if Calvin hadn't brought that image out in the open.

*

Smack

* she landed one across his face.

Just for good measure she delivered one to Calvin too.

*Smack*

After a long silent moment, the three of them burst into laughter, almost uncontrollably for a moment. Damon was right. She was actually thinking about it, not on purpose, but C had somehow tricked her into it. Trying hard not to think of something almost assures that you will be thinking of whatever it is.

"Well is it?!" Damon blurted out. Comically interested in this surprise size contest and not willing to let the moment just pass and be forgotten. In other words, he was not going to let Annie save face.

Again, she couldn't muster a quick response, the question flustered her. Again, she would pay the price. Now playing in her mind; that night from long ago, what he looked like as he took off his clothes, while he took off her clothes. She remembered being almost shocked at his size at the time. She remembered being nervous, but that particular night, she wanted it.

Throughout the next round of beers, Damon did it again, he had made Annie inadvertently think about "the white elephant" as he now jokingly referred to it. They were all quite amused at this simple mind control experiment. It became a game. Her refusal to answer became a source of laughs as well. Calvin and Damon agreed that her silence must mean only one thing, which was of course an admission that C was in fact, the "bigger man."

She knew that the guys were relishing the idea, but they had bested her on this one. She couldn't think of a way out of it. She thought it was funny too, the three of them had a strange sense of humor when they were together. She took some joy in not admitting to anything.

Calvin had a dare for Annie. Another throwback to the type of games they used to play that would always get at least one of them, if not all of them into trouble.

The dare?

"Tell 'ol Hot Roddie that your ex was bigger."

"I couldn't!! " she reacted but laughed at the idea, they were having fun, a few drinks laughs and at the time, the thought of it was quite amusing.

"You can tell him that its ok, and that you don't really care about that." Another hilarious addition that none of them believed, but thought that would ease inevitable tension the statement would bring. She had no intention of going through with it.

Later that evening Rod was less than amused when she came staggering through the door and knocked over a glass when she got home from her night out. She offered to make it up to him and stripped off her clothes. It was less than coordinated and she lost her balance several times during her drunken strip tease. He smiled. She stripped him too. His cock grew, she kneeled before him and took him in her mouth.

"You like that giant cock in your mouth" he said. A little dirty talk. She gagged on it momentarily as it was a bit funny considering her earlier conversation with her drinking buddies.

"Too big for you?" He reacted.

Then without warning, without thought, she mindlessly executed her buddy's dare. She laughed it off as it was good natured fun, but she felt it. She felt what was once hard in her mouth slowly turned soft. She back peddled.

"I'm kidding baby!"

"A strange thing to say" as he looked perplexed.

She tried vigorously to bring life back to him with her mouth and tounge. She offered up her pussy. He made an attempt, but by then he had gone completely limp.

The next day, she woke certain things were back to normal, her hangover completely gone. The haze of the previous night grew a bit hazier. She was a bit hornier thanks to the night before, having not gotten satisfaction she needed. She rolled over and climbed on top of her fiancé. They kissed and carried on as they usually do. He slipped her out of her nightie, she pulled down his shorts, arched her back, knowing he loves her body presented to him.

Things heated up, they reached the moment where the foreplay would end and he would enter her. The moment didn't come. He only momentarily thickened slightly. Not nearly enough for a successful romp, but even that didn't last but a moment. He deflated quickly.

"I guess I'm just not in the mood." He rolled back over and went to sleep. Annie was shook and left precariously wanting.

Next day, the same thing. This time it caused a bit of an argument. Things got unpleasant and he ended up sleeping on the couch.

Alone in their room, very sexually frustrated she fired off a text to Calvin.

"The dare did not go well, thanks a lot jerk!"

She let her own hand wander about her body, she really needed release. She felt herself begin to swell, moisten. As she began to feel aroused, her phone buzzed, it was a response from Calvin. He couldn't believe she actually did it. She finally convinced him that she unfortunately did even though she should have kept her drunken mouth shut that night. He wrote back an attempt diffuse the situation.

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"A dare is a dare."

She started to explain to him the fallout from the dare. It felt a little wrong, dirty to be telling him these intimate details from her relationship. But they were "friends," they do go way back, so she let herself continue. Without really thinking, she admitted to her fiancé's impotence, she revealed her sexual frustration, she revealed how she had resorted to touching herself as her fiancé snores out on the couch in the living room.

It felt good to vent a little and she was glad to have someone to talk to, even though it was his fault. He reminded her that she wasn't actually forced to play the dare. They were laughing together about her situation. Then after a bit of a pause, she received another message.

"Well... as your "friend" I could help you out with your "frustration."

Her immediate reaction was that eye roll that became a commen response to something Calvin would say.

"Of course you would," she snarked sarcastically at his ridiculous offer.

"Well yeah, of course I would" Somehow his retort sounded less smarmy, and more sincere, even supportive. Was he just being empathetic? She wondered. Her compromised thoughts clouded her judgement.

Her mind was dim, as it gets when she is deprived of sex. In a rare moment of clarity she put an end to this silly and wildly innapropriate conversation. She put the phone down, let her hands try and soothe the agony. She could hear her fiancée snoring, a haunting racket from the other room. She tried tuning it out, tried to focus, tried to get herself off, but she could not quite get there. She was desperate. Her fiancé was not up for the task, leaving her needy. The menacing buzzsaw vibrations from the snoring, coming from the living room filled the air. She reluctantly grabbed her phone.

"Just as friends...since it is your fault after all, ok?"

"Ha, I'll leave the door unlocked" he answered, suppressing a victorious boast. Somehow, a potential "booty call of the year" had fallen into his lap.

A few minutes later she popped a gummy and was sneaking past the croaking heap that was her fiancé in the living room and heading back to a place from her past.

As she made the familiar short drive over to the house she had been to several times she couldn't get over the sexual frustration she was feeling. Feeling that she was going to get some release excited her.

But this was different. Although she had slept with Calvin once before, she wanted this to feel less like cheating and more just taking care of an issue that was causing problems in her relationship. She even rationalized; I can just get a quick fix to last me until this fallout with my fiancé blows over. She was confident they will be back to their usual lovemaking selves soon.

Since this was different, she thought of some ground rules on the way over. Definitely no kissing, there was no purpose as this was strictly business. Additionally, she just wanted to get in and get out. No stripping off each other's clothes, just getting right to business. She would lower her pj pants just enough for him to get in, get her off and she would leave just as quickly as she came. No blowjob, no playing with nipples, no forplay at all.

Despite taking "passion" out of the equation, she was so wet in anticipation of actually getting what she so craved.

She arrived and stood outside his door for a moment to compose herself. Annie reminded herself of her rules, then turned the knob and let herself in.

When she entered, he came down the stairs to meet her. He leaned in to hug her, but she put her hand up. "Not so fast C" I have a few rules.

She went over the rules she came up with on the way over. After she finished what seemed to be a lengthy list, he smirked.

"I think you put too much thought into this, don't worry so much, we've done this before"

"Once! And that was different!" She corrected him. "And you know, I barely even remember if you are bigger than my fiancé or not anyway. I was much less experienced then."

"Well did you come here to lecture me, or did you come for another reason? I just want to help, as a friend, like you said." He was still in disbelief that Annie was actually here and he was about to "score" with her.

She was a bit overwhelmed with the whole situation, and she was also very horny.

"Do you want to come up to the bedroom?"

She felt that her rules were already being tested, she stood firm "no bedroom" just right here.

She asked him to dim the lights. He did.

He moved very close to her. She turned her head away from him sensing he might try and kiss her. He gently brushed her hair back behind her ear.

"Turn around so I can take care of you."

She did as he told her, she lowered her pants slightly. She had no panties on. He grabbed firmly to her ass cheeks which made her let out a small yelp.

She felt him grab hold of the waistline of her pants. She held on to them to ensure they didn't go down any further.

"Very well" he responded. Seemingly agreeing to her boundaries.

He took a step back and removed his pants.

"I prefer mine completely off, you don't have a rule against that do you?"

She was eager for him to get started, especially now that her ass was exposed.

"Just do it already" she sighed.

She felt a little shame that her ass was out while he stood behind her, one step away, seeing her waiting for him in anticipation. She felt some consolation since the length of her shirt

mostly

covered her.

He removed his pants, and his shirt and grabbed ahold of her waist.

"Do I get a say in any of this? After all, it is you who is in need. I am offering assistance to you."

"You got me into this mess." Annie snapped.

"I think you got yourself into this," he responded with a grin. "So do I get any say at all?"

"Fine." she answered; "What is Your say?"

He didn't answer instead pulled her pants down to the floor. She reached her hands behind herself, instinctively covering her completely exposed ass now. He didn't stop there. He reached around to the front of her shirt and was able to pull it up and over her head, it remained hanging on her arms behind her back.

He didn't stop there either. He made short work using her shirt to bind her arms behind her back.

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This really caused a shocked gasp from her.

He now had her completely naked, arms tied, and bent over. The pajamas she came over wearing were loose fitting and easily removed. He let her know that, getting to see her, all of her, is what he meant by getting a say.

"Relax." He coached her. "I won't do anything you don't want." She was even more overwhelmed. She felt him press his hard cock just outside her very wet pssy. He stopped there, held it in place.

"Do you want me to stop? I broke one of your rules, what do you want to do now?"

His cock nestled into the part of her lips. Ever so lightly. Not fully delving inside of her. He was parked in her primal doorway.

She was vulnerable, much more so than she anticipates. She was supposed to be in charge, she was supposed to show up, tell him how it was going to happen, receive her orgasm and then leave.

Now she was naked and bound, her lips moistened the tip of Calvins member. He pulled slightly on the shirt that held her arms behind her back. Not enough to pull her backwards fully taking his cock, but just enough to where she had to resist a bit to hold her ground.

"Just take what you came here for, you have nothing to worry about at this point. Your already here, and there is no turning back from how far you've come already."

She couldn't bare it anymore, she pressed her hips back pressing him into her. She felt him starting to run through her. She couldn't hold back a very loud moan as he slowly pressed into him taking her deeper. She only made it half way, although she didn't realize it. It was as deep as she was used to going with Rod, but it filled her more. He pressed the rest of him deep into her. She wasn't expecting more and wailed loudly.

As he moved back and forth by pulling her hips into him. She would pull forward as it seemed to much for her to take, and he would pull her back. She couldn't stay quiet. She was practically howling.

It didn't take much of this. She had been horny for days. She felt the rush of a monster orgasm building within her. She felt his hand on her head, wrapped her hair together and pulled back. With one hand he pulled her arms and with the other he pulled her hair back. Her legs began to shake, the inevitable began to take hold of her. She was going to erupt at any moment.

The door swung open. The same moment when the wave of orgasm took over her body, forcing her to pulsate and scream in pleasure, Calvins roommate came bounding in, she was fully on display. Calvins grip on her hair lifted her face so that she was looking directly into the roommates face, both of them shocked.

He was obviously delighted at the surprise. She panicked but couldn't stop the screaming uncontrollable waves that rushed over her.

"Oh yeah Annie!" Of course he remembered her from when she used to hang out with Calvin more. She remembered him too. He had always given her a bit of a creep vibe. Their friends group would go on weekend trips together, he was always trying to catch her changing, or sleeping in her panties, he's even walked in on her in the bathroom, and stared at her at the pool. She had fought to ensure this creep would never get a peek at her. She was successful too, until now.

For him, it was a fantasy come true. He whipped out his phone and took the most compromising video of her. A video of her at the height of an orgasm. Tits swinging, getting fucked hard by Calvin.

Her knees gave way and she fell down to them. She could barely see straight. She couldn't catch her breath. What she felt was amazing, but at the same time she was mortified by the appearance of his roommate. Such efforts she had gone to in the past to protect her modesty from him.

Now, he had everything he had tried for over that time, and so much more. He finally won, and he won big. He wasn't done.

She was recovering, a post-gasm fog was over her. She actually forgot for a moment the roomate as she was so wholly satisfied. She had never felt like this, it was amazing. It left her weak. She wanted to collapse on the floor but Calvin still had her propped up, like a hunter displaying his trophy kill. Displaying his "trophy" Tommy, his twisted roommate. She was spent.

"Do you remember who's bigger now Annie?"

"Yes."

"Who's bigger Annie?"

"You are."

Her responses were trance like. Her current state left her totally subservient to Calvin.

"Say it again, who's bigger?"

"You're bigger."

"How big?"

"So big."

"Tell me how much you liked it."

"I loved it"

"You really needed that didn't you?"

"I really needed that"

"You really needed a huge cock inside of you."

She responded in monotone to his every prompt, in the same hypnotized like tone.

"You wanted me to make you orgasm."

"I wanted you to...."

Like being abruptly awakened from a bizarre dream, her eyes opened and she was inches away from a now pants-less Tommy. His cock inches from her lips.

"What the fuck?!"

One of them told her to relax, she didn't make out who. It also became undeniable to her in this moment, that her gummy just kicked in.

"Calvin what the hell is going on? Get away from me Tommy!"

Tommy showed her his phone, the video of her, pracitically in heat. A video of her uncontrollable screaming in pleasure, unaware that she was staring straight into the lens.

"If you want me to delete it....." he said deviously.

She looked up at him, not able to believe he was actually engaging in bribery. Calvin had let her go.

On her knees she contemplated the reality she faced. She pleaded with Calvin not to let his roommate do this. Calvin tried for a moment but Tommy shut him down fast. One of the several character traits that made her unfomfortable around Tommy was that he was quite forceful, even to Calvin.

Looking up at Tommy, with her video still playing, there was no way she could allow that video to stay in his phone. She quickly tried to grab at it but was unsuccessful. So unsuccessful that the lunges planted her face directly into Tommy's penis.

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