*Disclaimer: This story is a work of fiction and in no way condones acts of sexual assault or violence. All acts of sexual intercourse and play depicted in this story are preformed by consenting adults.*
[https://imgur.com/btquDE7](https://imgur.com/btquDE7)
It was hard to believe for any of the girls that this would be their final year of college together. Rachel, Olivia and Izzy had been friends for as long as they could remember and all of them wanted to make sure their final year together before they started their new lives, would be one to remember. They saved enough money to buy tickets to Cancun for their final Spring Break, with every intention to have the best experience ever. Shots. Parties. Music. The first two days were as amazing as they could be. Then it felt as if they caught the luckiest break in the world when they met a man named Isaac while at a pool party.
He was close to their age, assuming he was a college student like them. He was handsome and had a soothing voice. His charisma almost hypnotic as he easily persuaded them to join him as he showed them around to the best spots in the city. Enjoying each other’s company as he never gave off the energy that he was trying to sleep with any of them. Genuinely just trying to be a good person. Then he told them about his parent’s yacht. How he planned to take it out soon and wouldn’t mind the company of three gorgeous women. No strings attached. So long as they didn’t mind being recorded.
While the idea of being record made the girls a bit squeamish in the back of their minds, their guard had been lowered enough with Isaac that they agreed. After all, none of them had been on a yacht before and Isaac seemed trust worthy and harmless enough. The next thing they knew they were opening champagne bottles, spraying it all over themselves, eating exquisite lobster, grinding their asses on each other, doing shots off their stomachs, and sunbathing on the front deck of the boat while they wiggled their asses. The girls were even nice enough to give Isaac a lap dance for his generosity. All while he recorded ever second of their fiascos with his camera.
Isaac seemingly and naturally brought up a private island his parents owned to the girls mid conversation as they enjoyed another fine meal together. How beautiful and secluded it was. Truly a once in a lifetime opportunity for amazing pictures. Teasing the girls with this information and that he shouldn’t take them their or it would ruin the magic. Naturally, with how intoxicated the girls were, they begged him to take them there. That it was their final year together and they’d be very grateful. The girls having no idea that their begging was making him rock hard. He eventually caved in and steered the yacht that direction as the girls cheered.
It was a true sight to behold. Much larger than expected for a family to own. It had a beautiful beach line. A lagoon large enough for the yacht to have plenty of space in and accessible through a cave tunnel. And tales of a waterfall within the island. The girls had a blast diving off the yacht and swimming in the water. Teasing Isaac by taking off their tops and giggling. Taking plenty of pictures and thanking him with plenty of intimate hugs.
**Round One**
Once the girls were tired and a little more sober, Isaac gathered them together to play a little game. Would you rather? The girls saw no harm in it. It was playful at first. Would you rather be blind or deaf? Would you rather be able to fly or turn invisible? Then it started to get a little more risque. Would you rather flash your tits or your ass? Would you rather kiss another girl or the worst guy you ever met? More and more it devolved as the sun reached the height of the day. Would you rather get fucked in the pussy or the ass? Would you rather have cum on your face or on your back? The girls giggling as some of the questions were turning Isaac on. Then it was his turn once again.
“Would you rather become a sex slave, or left on this island to die?”
His voice as smooth as ever, but unwavering. His inviting persona changing to one of aggression as his eyes fixated on the three girls gathered around the fire put on the yacht. He was dead serious as the girls stopped giggling and stared at him with concerned looks on their face. This wasn’t fun anymore and they wanted to go back to the mainland. They’d never get that wish as the girls heard the sound of another boat approaching from the distance. Getting louder until it stopped and seven large men got on the yacht. Some carrying large bags.
“Look at these fine hoes. You really know how to pick them Ike.”
The girls got up, hugging each other, trying to keep themselves safe as these men laughed and surrounded them. Some men reaching out to grab at their ass. Olivia was always the bravest of the three and slapped the man’s hand away from her friend. They simply laughed and poked fun at her fearlessness.
“This one’s got some balls.”
“I’m going to enjoy breaking her in.”
“Let us go you bastard!” Shouted Olivia, trying her best to ignore the men’s unnerving statements.
“Oh, you’re in no position to make demands.” Said Isaac in a menacing tone as the men around the girls grabbed at them, ignoring their screams and shouts. Olivia looking just in time to see one of them grab rope out of the many bags and bind their wrists behind their backs with them.
“We’ve still got a game to finish. Only now, the rules are going to change. It’s going to be more of a competition now. I’m going to ask a ‘Would You Rather?’ You’ll have ten minutes to give me an answer. If you don’t, a third option will be given to you. And trust me. It’s going to be so much worse than the other two. After that, the girl who does the best in each scenario will be given an advantage the next round. Second place will get nothing. Third gets a strike against them. Three strikes and…well…you’ll figure that out soon enough.” He said with a devious smile as he circled the girls. Looking up and down their bodies.
“First round. Would you rather make all of us cum as much as possible using your hands, or allow us to cum in our own fun…degrading way? Time starts now.”
Isaac places his phone and the timer where the girls can see it as he and the rest of the men whipped out their cocks. It came as a surprise to all the girls how well endowed they all were and they weren’t even hard yet. Stroking their cocks right in front of the girls as they simply waited for the next move.
Five minutes go by and the girls huddle together in solidarity. Every cock is intimidating to them. Looking as big as the pornos they’ve seen. Bigger than any cock they’ve ever had to please. Second by second the timer gets smaller and smaller. Until two minutes are left and Rachel finally breaks her silence.
“I’ll use my hands…” Saying it loud enough for the men to all hear, but still ashamed that she said it. Slowly walking up to the men.
“Rachel! What are you doing? Whispered Olivia in shocked surprise.
“I’m sorry Liv. I don’t want to know what happens if we don’t pick one.” Tears in her eyes as she gets on her knees in front of two men and begins to stroke their cocks with her hands.
“That’s right baby. Stoke daddy’s cock like a good slut.”
“Ever felt a monster like this in your hand before?” The men spoke as Rachel had to forcefully stop herself from crying.
Olivia looked up to see the biggest and most satisfying smile on Isaac’s face. Staring down at each other as Isaac saw right through her raged filled gaze. The timer continued and their was only ten seconds left before Izzy panicked. Her breathing sporadic.
“You guys pick!” She burst out as she made her way towards the men.
“Izzy?” Olivia felt as if she didn’t even know her friends anymore as they’d rather do these brutes’ bidding than stick together.
“I’m sorry Liv…” As one of the men made her lay on her back and began to fuck her large tits with his cock. Her humiliating unending as another man used her feet. Making her feel less and less like a human being and more like a sex object used for pleasure.
Then the timer was over for Olivia. Isaac whistled and two men grabbed at Olivia’s head. Forcing a ratchet gag that they pulled from one of the many bags into her mouth and securing it tightly around her head. She was unfamiliar with the device as she fought back the best she could. Feeling the rubber enter her mouth. The man pressed down on a lever and Olivia could do nothing as she heard the clicks of the metal and felt the sharp pain of her jaw being forced open.
“Looks like Cunt here gets to use her mouth for this challenge. Have fun boys.” Isaac said. His voice extra potent as if to pierce through Olivia’s soul with a knife.
And so the first round had truly began as each girl endured their own form of humiliation. Rachel experiencing the fruits of her labor as the first two men who’s cocks were in her hand cam hard and all over her face and into her hair. She leaned back as she’d never allowed any of her partners to degrade her like that, but there was no time to cry as two more men took their place and felt her hands wrap around their cocks.
“God damn, this Bitch has got some soft hands.”
“Look at her go. She’s a god damn professional. Look at me Bitch when I’m talking to you.”
Rachel looked up with puppy dog eyes as if these men would stop their wrong doing and set them all free. But it was all useless as she continued to stroke at the cocks in front of her. Overwhelmed by more surrounding her. The men stroking their behemoths while each tip looked like an eye staring right at Rachel. Meanwhile, Izzy laid on the ground. Her well endowed breasts easily making her first man cum all over her face as he ripped her pink bikini top open to reveal her nipples. At the same time, another man thrusting his cock between her feet, making sure to get his cum between her toes. A sensation that made Izzy sick to her stomach as she felt the warm semen drip down her soles.
“Whore here’s got a killer body. She could be a fucking model.”
“Too bad we can’t fuck her holes yet.”
“Patience men.” Isaac said to calm the masses. His tone letting everyone know that this was all part of the game.
Izzy’s entire body was up for grabs and humiliation. Men would use her armpits. Tits. Feet. Stoking their cocks with her hair. Make her stand and thrust their cocks between her thick thighs. Or lay down and thrust between her ass cheeks. While Rachel took the brunt of cum on her face, Izzy’s entire body was beginning to get covered in jizz.
A would you rather that would have been the worse one to pick, had Olivia not abstained from playing. A line of men formed in front of her as they all waiting with anticipation to face fuck the defiant little Cunt. The first man wasting no time grabbed at Olivia’s head and pushing his cock down her throat. Try as she might, she stood no chance trying to shake the man’s cock away from her mouth as his hand held her in place. The tip of his cock easily pushing passed the back of her mouth and down her throat. She couldn’t hold herself back from puking.
Olivia thought for a split second that now they’d leave her alone. How wrong she was when they sprayed her down with a hose connected to the sea around them. Feeling high pressured salt water blow into her mouth and causing her to gag. Feeling as if she was drowning. When she was all cleaned up. The man resumed face fucking her until he cam deep down her throat. A feeling that disgusted Olivia as she felt this stranger’s cum slide down her esophagus and into her stomach. Then the next man was up. Olivia gagged and drooled all over herself as cock after cock thrusted in and out of her mouth. Any time she puked she was sprayed down. She felt the weight of the cum inside her stomach making her sicker and sicker. Before long, she was puking a white mass. Getting hosed so many times her black bikini top had been ripped off her body.
All the girls could do was watch in horror as they saw each other getting used by all these men. Rachel and Izzy with the most sympathy to Olivia. They all wondered when this would end as cock after cock entered their vicinity. Then a timer went off and the men groaned and complained.
“Damn, I really wanted to face fuck Cunt over there.”
“Sorry gentlemen. Rules are rules. Who did the best?”
“Well Bitch here got tired and barely got twelve of us to cum.”
Rachel silently sobbed as she sat there between the men. Her face dripping with cum that made her feel like a common whore. Her arms exhausted from jerking off so many cocks for so long. Still, she didn’t look nearly as bad as Izzy. Who’s entire body, hair and face had spots of trickling cum from men using whatever they could to get off.
“Twenty-two. Whore here did amazing! Not too hard considering her rocking body.”
Izzy felt shame as one of the men praised her for being used like nothing less than a cum rag. Wanting to badly to shake her shoulder away from the man who placed his hand there. Her and Rachel’s horror nothing compared to when they looked over to Olivia. Still coughing from the non stop face fucking. Drool and cum pouring out of her forcefully gaping mouth.
“Pretty sure we forced thirty loads down Cunt’s throat. If not more.”
“Our first winner! Congratulations Cunt. Rachel here gets the first strike.” Isaac said as he sarcastically applauded and Rachel began to weep some more. “Shall we move on.”
**Round Two**
“Next round is all about making sure you three will be well behaved. Good girls don’t cum. The one who cums the least will be the winner. This round is going to be a little different. Bitch…” Isaac’s voice became more sinister when he turned his attention towards Rachel who was still sobbing, her head jolting up as Isaac addressed her degradingly.
“Would you rather sit on this sybian for an hour? Or be fucked in that pretty little cunt of yours for an hour? Whore. Would you rather sit on this sybian for an hour? Or let these boys fuck you in either hole they want? And Cunt. Would you rather sit on this sybian for an hour? Or be fucked in the ass? You have five minutes to decide. Starting now.”
The girls knew what Isaac was doing. He was using the knowledge he gained from them playing this game before it took its dark turn. Rachel admitting she only liked to get fucked in the pussy. Izzy not being able to choose which since she liked both so much. And Olivia, who was intoxicated and relaxed enough at the time, unafraid to admit she loved anal.
Rachel and Izzy couldn’t figure out what to do. They’d use vibrators before, but never used a sybian before as the men set them up. They were thinking in their minds what would be the best option. What would make them the winner. Playing against their best friend behind their back. Until finally they spoke.
“I’ll let them fuck me….” Rachel reluctantly said.
“I don’t want to sit on that thing….” Izzy followed up.
Once again. Olivia stood her ground. Unwilling to play this sadistic game even if her friends were willing to. Isaac approached her, kneeling down to her level to remove the ratchet gag from her mouth and finally give her jaw the rest it needed. He cupped Olivia’s chin in his hand, looking her directly in the eye.
“Just so you know. Bitch will still get the handicap this round for losing the last one. You might as well pick. You’ll stand a better chance. What do you say Cunt?”
Olivia looked at Isaac with hate in her eyes and spat in his face. Her only answer as time ran out and Isaac snap his fingers. His face filled with disappointment as he rose above the defiant girl. Olivia stood no chance as the men surrounded her and carried her off to the front of the yacht where she’d be subject to her worst humiliation of the night. Izzy and Rachel only got glimpses of what the men were doing to her as they themselves were bound to a table, but they heard her screams. The men’s laughing and heckling.
As the round started, Izzy and Rachel were tied next to each other on opposite sides of the table. Their arms crossed tightly bound behind their backs as the rope around their chest made their breasts pop out. Their ankles wrapped in rope that stretched their legs in a painfully forced split while their mouths were stuffed with a shiny red ball gag. While Rachel was still given her handicap for losing the last round. A nice little vibe right on top of her clit. They looked over and saw the horror that had befallen Olivia.
She became a living figurehead hanging off the yacht’s metal bowsprit. A dildo machine with a piston long enough to reach her body and shove the silicone cock up her ass as it relentlessly went in and out of her tight hole, barely looking like it was going to slip out before shoving itself all the way back in. A vibrator strapped to her thighs that mercilessly vibrated on her clit, along with two additional vibrating eggs taped to her nipples. And a dildo gag to keep her mouth stuff and continuously drooling into the ocean below her. She couldn’t even try to hold back the moans at the vibrations and anal fucking were too overwhelming for her mind to handle. She felt utterly humiliated as the men laughed at her. Took photos and videos and sprayed champagne on her from the deck.
Olivia was off to a horrible start as she cam within the first five minutes. Meanwhile, Rachel and Izzy were dealing with their own struggles as the men gathered around them eager to shove their cocks into their holes. Rachel moaning just as loud as Olivia and right into Izzy’s ear as cock after cock slid inside her pussy and the vibrator did it’s job on her clit. She always loved the feeling of cock inside her pussy and the sensation of her body tightening around whatever slipped inside her was too much for her to bear. She cam for the first time shortly after Olivia. Izzy fared better than the other two. While both holes still gave her pleasure, she still preferred getting fucked in the pussy over the ass. Any time one of the men pressed their cock into her ass, she was mentally relieved.
It was as if the men were never satisfied from the last round as they cam over and over again into the two girls. Their holes filling up to the brim with cum until they were overflowing and streaming down their ass cracks, making the puddle of cum underneath them larger and large with each passing cock. Olivia faring no better as the constant fucking from the dildo machine into her ass and the vibrators on her body were too much for her. She was caught in a mental corner. Resist the urge to cum and not play their twisted game. Making the pain too much to bear. Or cum as much as she wanted and be humiliated regardless. In the end, she allowed her body to posses her mind and cum when it felt like it. Her orgasms getting so intense, she squirted for the first time. The men laughing as it sprayed down into the ocean below her.
By the end of the round, Olivia orgasmed an impressive eighteen times. Easily losing the round. Rachel was second. Having cum eleven times. With Izzy in a close third place, securing her spot as the top contestant. Having only cum nine times. Even after the men figured out she like to get her tits fondled while fucked. Reluctantly admitted to herself how good it felt to have her breasts fondled, sucked and pulled on. Making her cum at least two times from anal as her ass was stretched to its limit.
“Looks like Cunt is our loser for the round. Whore impressively keeping her lead, but let’s see how you do this next round. It’s going to be fun, so let’s make it a surprise.” Isaac taunting as he stood over the exhausted girls, breathing hard and hoping that none of them get pregnant as the cum dripped out of their pussies.
Part Two: [https://www.reddit.com/r/Erotica/comments/128kfjr/22_would_you_rather_an_institution_story_group/?utm_source=share&utm_medium=web2x&context=3](https://www.reddit.com/r/Erotica/comments/128kfjr/22_would_you_rather_an_institution_story_group/?utm_source=share&utm_medium=web2x&context=3)
Source: reddit.com/r/Erotica/comments/128kewv/12_would_you_rather_an_institution_story_group