Olivia’s Game

By randomer555.

Mike stood in the corner, staring down at his drink, wishing he had the guts to mingle with the crowd. He was at a crowded house party, teeming with plenty of the hottest girls on campus, yet he hadn’t even had so much as a conversation, much less gotten any action or numbers.

He shouldn’t have been surprised or even disappointed – he knew deep down that this had been the inevitable outcome, that his pre-party pep would fade, and that his resolve would fold like a house of cards. Hell, he should even be proud, one could argue. He was finally attending his first college party, and it had taken until senior year for this step forward.

Yes, senior year. Numerous factors could be inculpated for the fact that he truly had not taken advantage of the college experience: the fact that he had been immersed in his studies (and in dogged pursuit of maintaining his stellar GPA), the fact that he was a commuter rather than a campus resident, the fact that he worked a part-time job in addition to studying full time, or even the fact that he was not a big fan of drinking (indeed, he was still nursing his first beer).

But deep down, Mike knew that these were all little more than excuses. Deep down, he knew he was on the shy side when it came to romance. No matter how many times he mentally prepared himself, he folded and caved at the crucial moment. Academics, not girls, were his province.

He had vainly hoped tonight would be different, but the same trajectory had played out. It was nearly midnight, a couple of hours after he had arrived, and he had yet again voluntarily relegated himself to wallflower status.

He hadn’t approached a single chick. Hadn’t played a single drinking game or even finished a single beer, for that matter.

He sighed. This had been a stupid waste of time, and he had to study for an upcoming exam anyway. It was time to throw in the towel and go home. He was debating whether or not to at least force down his now lukewarm beer when a familiar voice called out to him.

“Hey, Mike, right?”

He looked up, startled, and found himself looking up at Olivia, a girl from his economics class. From what little interaction he had had with her, he had inferred that she had little interest in her studies but an abundance of interest in partying. She was the stereotypical college party girl, achingly pretty, rather preppy, and, loathe as he was to admit it, vastly out of his league. What interest could she possibly have in him?

Mike regarded her warily as she approached, smiling widely, drink in hand.

If she’s plastered, turn her down outright, Mike said silently to himself.

“Hey. Olivia, right?” He managed, cursing himself for bumbling so badly.

“Yeah!” She said vivaciously. “I guess you do pay attention to more than just your books!” She teased.

Mike found himself just nodding, he hated it, but he had once again seized up under pressure.

“Why don’t you join the party?” She asked, still smiling. “Come on, follow me.”

Mike desperately tried to suppress the stirring in his crotch as he followed her, practically enthralled. He silently admonished himself that, as of now, they were just talking. He didn’t dare hope it would progress beyond that preliminary stage.

He followed Olivia towards the center of the party, sitting on a couch. He downed the rest of his beer, trying his best to seem cool and casual as the two of them exchanged banter for the next few minutes until Olivia needed a new drink.

“Yeah, sure.” He agreed to get her another drink far too quickly. Almost reflexively. He could have sworn he had seen Olivia’s lips curl into a brief smile of amusement. Or worse, that he had confirmed some hunch of hers. He decided to get another drink for himself, as well. Hopefully, he could salvage his image at least a little bit.

A million doubts and contingencies were swarming through his head as he brought the drink back to her, painfully aware of the bulge in his pants.

“Mmm, thanks,” she gracefully extended her arm to accept the drink, and Mike couldn’t help but notice how pretty her red nail polish looked.

Mike sat back down awkwardly, careful to conceal his growing erection. He took a sip of his drink, but his efforts to appear casual fell apart when Olivia leaned against him on the couch.

He shook and shuddered, prompting a quiet giggle from her. He couldn’t help but appreciate how pretty her hair was and how nice she felt against him. Mike decided to take the plunge and put his arm around her. To his relief, she didn’t object.

But Mike still couldn’t find much of his voice, and so an awkward silence ensued. A silence that was broken by a third party.

“Hey, bro, you made it.” Mike saw Anthony, a classmate of his, the one who had told him about this party, and a typical party animal, walking by. He flashed Mike a quick thumbs-up as if to say ‘nice.’ Mike nodded quickly and murmured a greeting.

“Hey Anthony,” Olivia gave a much louder greeting. Mike felt a pit in his stomach. He hoped Anthony wouldn’t ruin whatever chances he had, but it seemed possible.

“You know him too?” It was the best conversation starter Mike could buster.

“Oh yeah,” she answered as she leaned into his ear, “he has SUCH a big cock.”

She couldn’t but laugh as Mike blushed. He was sure he wouldn’t measure up to Anthony.

“He fucks like a bull,” she continued.

Mike couldn’t think of a response, damning himself for being silent and praying the conversation would become less carnal and that the topic wouldn’t drift to his own experience (or lack thereof). But his hopes wouldn’t last.

“How do you fuck?” She whispered. “Are you one of those brainiacs that has a secret nine incher?” She laughed.

“Well, it’s…it’s not nine inches,” Mike struggled to begin, “but it’s not small or anything.”

“Well, maybe I should be the judge of that,” she mused. “when was the last time you got laid?”

Mike’s breath caught in his throat. The truth was he hadn’t, but he wasn’t going to out himself as a virgin.

“It’s been a while,” he said vaguely, hoping in vain that would satisfy her. But it predictably didn’t.

“How long ago?” she pressed.

“A couple of years ago, at a friend’s party.” He lied.

“I’d like to hear more about it, but can you get me another drink first?” It seemed obvious she didn’t believe him.

“Sure.” He quickly answered, again way too quickly.

“Good boy,” she giggled, patting his ass as he got up. It was painfully obvious she was just using him and messing with him. Part of him screamed to leave and salvage his dignity, but the horny side won out. God, he was such a simp, he thought as he returned with the drink. His heart sank when he saw Anthony had taken his spot and that the two of them were chatting away. Even worse, she reached out and took the drink without acknowledging him. Great, he had made a fool out of himself in front of two people tonight. He was leaving.

“Wait,” she called out as he walked away. “Are you interested in a threesome?”

Mike stopped in his tracks, not daring to believe what he had heard. He whirled around incredulously.

“Really?” He asked.

“Yeah! With a fun little twist,” she answered with a gleam in her eye and a knowing smile. Was tonight really the night? Was he really going to swipe his v-card tonight? And with one of the hottest chicks on campus? Something said it was too good to be true, but he threw caution to the wind and said yes.

One hurried walk through campus later, the three had entered Olivia’s townhouse and arrived in her bedroom.

“Alright, you guys ready for a little game?” She asked cheerfully.

“Game?” Anthony raised an eyebrow.

“Yep!” She said she rummaged through her dresser and pulled something out, taking care to hide it from view.

“I’m going to jerk the two of you off,” she smiled. “And whoever cums first loses and gets to wear this while listening to the winner fuck the shit out of me.” She giggled as she revealed a small, pink plastic chastity device.

“What the fuck?” Anthony said forcefully. “I’m not wearing that fucking thing.”

“Yeah, me neither,” Mike said, not quite as forced as Anthony had.

“Oh, come on.” Olivia cooed. “Don’t you want to fuck me?”

“Well yeah, but-,” Mike started. Before he could finish, she skipped over and whispered into his ear.

“Wouldn’t it be nice if I were your first?” She whispered so quietly that only Mike could hear. “I know you were lying earlier. Isn’t this worth the risk?”

Mike felt a stir in his crotch as he merely nodded, knowing full well how stupid this wager was but being far too horny to acquiesce to common sense.

Moments after he agreed, she was in Anthony’s ear, whispering something. Anthony seemed to smile and nod confidently as Olivia beamed and stepped back, placing the pink cage on the dresser.

“Alright,” she said. “Let’s see ’em. Take those cocks out.”

Mike was more than a little apprehensive but obliged with shaking hands. His worst fears were quickly confirmed – he definitely didn’t measure up to Anthony.

“I know who I’m rooting for,” Olivia said as she looked approvingly at Anthony.

Mike felt a pang of humiliation. Olivia got down on her knees, taking each dick in her hand and giving a quick squeeze to each. Mike groaned with pleasure at this, the first time another hand had touched him there. He felt a surge of pleasure and excitement but thankfully didn’t cum.

“Don’t cum already,” Olivia laughed. “God, that would be fucking sad.”

She began stroking the two of them, looking at both of them. Mike shuddered, twitching involuntarily and arching his back almost immediately. He knew he was going to lose.

“Are you arching already?” She laughed. “I hope you can last for a minute!”

Anthony moaned once, but otherwise still looked composed. Olivia leaned over and kissed the head of his dick, telling him it’d be hilarious if he managed to lose.

Mike hated how poorly he was doing. That it was a foregone conclusion, he would lose. There was no denying he wouldn’t be able to fight off the rising pleasure from her grasp that felt so good. He tried to think neutral thoughts and stave it off, but soon pleasure engulfed him, and he shot rope after rope of cum onto the floor.

Olivia laughed loudly and let go of Anthony, stroking Mike several more times. “Look at that fucking load! I knew you and your little dicklette wouldn’t last long!”

Mike felt shame welling within him. It was bad enough to last such little time, and it was the cherry on top to be embarrassed like this around another guy.

“Don’t look so sad.” She said teasingly. “You still get to stick your dick in something nice, tight, and pink!” She laughed at her quip as she grabbed the device.

“Do I have to wear it?” Mike asked, almost pleadingly.

“Yes!” She responded adamantly. “You lost fair and square.”

“Didn’t you like that hand job?” She pressed. “You might get that again from me if you let me put it on you.”

Mike wasn’t sure if it was worth it and said so.

“Well, if you don’t wear it,” Olivia said more forcefully, “I’m telling everybody you’re a minuteman with a tiny cock. What is that thing hard? Four inches?”

Mike did not doubt that Olivia would be capable of spreading unsavory rumors about him like wildfire. He was dealing with a spoiled rich girl who used to getting her way, after all. Even if he didn’t live on campus, she still could make the remainder of senior year hell for him. But would it be worse than wearing that thing? This couldn’t happen to him. Some providential miracle had to save him. It had to.

“Come on, Olivia, don’t make him wear that,” Anthony interjected.

Thank God someone was on his side. Thank you, Anthony. Help a fellow guy out, Mike thought gratefully.

“Do you want to fuck me, Anthony?” Olivia raised an eyebrow as she looked at him.

“Of course,” Anthony responded.

“Then you won’t interfere,” she responded sharply. “I’m not fucking you until Mikey here is in this cage.”

“Don’t call me that.” Mike objected.

“I’ll call you whatever the fuck I want.” Olivia snapped. “Now put this fucking cage on your little dick. If you don’t put it on,” she said as she walked toward him, “I’ll just tell everyone you let me put it on you anyway. You can either be secretly locked or be the campus laughing stock. Your choice.”

“Anthony,” he looked to Anthony for more support, but he looked away apologetically.

“He doesn’t care about your babydick,” Olivia laughed. “He cares about his prize, which is getting to fuck me senseless. He gets to fill my pretty pink pussy, and you get to fill this pretty pink cage.”

“Maybe,” Olivia continued her threats, “I’ll even tell that girl you sit next to about the cage and your performance. What’s her name? Christina? I know you have a crush on her. And she has a thing for nerds.”

Mike was mortified. He couldn’t handle such humiliation. Not with the one pretty girl he possibly had a legitimate chance with. If anyone was prettier than Olivia, it was Christina. And unlike Olivia, Christina had a brain as well. He couldn’t handle being humiliated by her. Just let Olivia have her fun for a little bit, and it’ll be over, Mike told himself. Although deep down, he knew a monster was being created. And that it would only get worse once that thing was locked on him. But he folded.

“Ok, you win,” Mike said with resignation.

“What was that? I can’t hear you.” She asked coyly.

“You win,” Mike said, louder this time.

“So you’ll let me lock you up?” Olivia laughed.

“Yes.” Mike looked down.

“Yes, what?” She wasn’t going to make this easy.

“Yes, I’ll let you lock me up.” Mike swallowed all pride, wishing the earth would swallow him at this moment. He had never felt so degraded.

“Yay!” She said as she began putting the cage on. She worked quickly, getting the ring on before quickly slipping the cage itself on. “All mine. All locked up.” She laughed as she clicked the lock. She grabbed his cage and played with it. “Chastity is going to be so difficult for you,” she was laughing loudly as she hefted his balls in her hand, “and sooo fun for me. You’ll never forget the color pink.” To his chagrin, Mike was already getting hard in the cage, resulting in an uncomfortable sensation and more laughter from Olivia.

“Now get the fuck out and in the hallway. This room is for real dicks only.” She snapped as she beckoned Anthony to the bed.

Mike felt two inches tall as he slinked by Anthony, who avoided eye contact with him.

“And you better stay right outside this door and listen to him fuck me if you ever want out of that little device.” She said firmly as she closed the door.

Mike sighed, struggling not to cry from embarrassment as he heard the beginning of moaning and grunting on the other side of the door.

The End.


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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