Olivia's Game Ch. 05

"What took you so long Mikey?" Olivia asked with a scowl as she let Mike in. It was clear he was on very thin ice here, even though he hadn't done anything wrong. She was just a high maintenance diva. But that fact did little to help his case - it was going to take a lot of supplication to placate her.
"I'm sorry, I-," Mike began to explain, shaking from both nervousness and the physical discomfort of the chastity cage.
"Oh you're going to be fucking sorry if you don't have a good reason." Olivia interrupted, crossing her arms.
"I was just doing what you told me to do." Mike pled desperately.
"It took you that long to get her number?" She laughed harshly. "God you're hopeless Mikey."
For the first time, her degradation didn't really stick or cut deep- he had successful gotten Christina's number and the interest was clearly mutual. In fact, he felt more annoyed by her empty words than humiliated. But talking back was out of the question. Especially with the pictures and video she had.
"Well, I guess any progress is progress." She said in a patronizing tone. "Did that little dick of yours try to get hard in the cage when you were with her?"
"Yes." Mike said, again her insults not cutting quite as deep now. But even though he was more secure and confident, he knew he had to be careful.
"If only she fucking knew," Olivia laughed. "Do you think she'd still be interested in you if she knew about that little pink cage?"
"Probably not," Mike answered, honestly this time, humiliation and self-consciously truly welling inside him for the first time since arriving at Olivia's. He knew the cage would probably ruin things, if it became known. It would probably scare off most potential romantic partners. Mike's heart sank at the prospect of his chances with Christina being ruined, which he knew was very possible.
"Of course not!" Olivia laughed. "It's fucking pathetic Mikey!"
Mike looked down. Even with his newfound confidence and romantic success, he knew it was pathetic that he had allowed himself to be locked up like this.
"And even if she doesn't find about that pathetic little cage," Olivia continued her degradation with even more vitriol than usual (as if she sensed he had been emboldened and needed to knock him back down quickly), "she'd definitely lose interest and be so fucking disappointed the moment she saw that pathetic little thing you call a dick."
Once again, Mike found himself relatively unfazed by Olivia's insults. Sure, he didn't measure up to the likes of Anthony or Olivia's other friends with benefits, but he was probably no smaller than average.
"Maybe it would be enough for her," Mike found himself objecting before be could stop himself. He immediately froze, realizing the danger of contradicting her.
"Did you just fucking talk back to me Mikey?" She demanded. "I think you need a little reminder about just how pathetic your little dick is. Take off your pants."
Resisting wasn't an option. With shaking hands, he quickly complied.
Olivia walked over and grabbed his cage and tugged on it as she spoke forcefully.
"Let's get something straight Mikey. Your pathetic little clit will never satisfy any woman. Not me. Not Christina. Fucking say it."
"It will never satisfy anyone, including Christina." Mike swallowed his pride, not truly believing what he said. And perhaps bursa escort bayan Olivia picked up on that, as she ramped up her verbal abuse.
"Trust me, Mikey. Christina will never be satisfied with this, thing." She sneered as she let go of his cage. "Let me spell out how it would go down. She's probably not as direct as me. She'd probably try not to laugh, and give it a chance anyway out of pity."
It's not true, Mike said silently. But his newfound security could only weather so much. And Olivia continued her verbal assault.
"Of course, your sad excuse for a cock wouldn't even come close to giving her an orgasm. She'd probably fake having an orgasm to be nice to you, and then finger herself to one afterwards, all the while thinking about how her fucking finger is more effective than her lover's sad little dick." Olivia's voice had more venom than ever as she took the degradation even further. "Eventually, she wouldn't be able to take it anymore. Eventually she'd dump your sorry ass. Or," Olivia grinned cruelly, "she'd cheat on you and start fucking guys with real dicks. She'd feel bad about it at first, until she realized just how good real cock felt compared to your tiny little dick." She held her index finger about an inch from her thumb to mock him as she laughed harshly.
For the first time, Olivia's insults began to cut deep again. He knew they shouldn't. He knew Christina liked him for him and wouldn't treat him like Olivia did, but old insecurities about his virginity and Olivia's cuckolding of him had reared their heads again.
"She would feel guilty about it at first," Olivia continued, clearly taking genuine delight in this deep verbal abuse. "But then she would let you fuck her again and remember just how pitiful your dick is. Just how pitiful you are. You would never make Christina cum. She'd keep faking orgasms with you, and keep getting fucked by real men on the side. You'd be Christina's cuckold." Olivia laughed at her joke.
"She wouldn't do that to me," Mike said meekly, genuinely beginning to feel insecure. What if he wasn't able to satisfy her? He wasn't sure he could handle that.
"Not right away Mikey," Olivia smiled, "but she would when she realized just how hopeless you are."
Before Mike could respond, Olivia continued.
"Maybe," Olivia said with relish in her voice, "she'd even realize that the only thing you're good for is being her bitch, like I realized immediately. Maybe she'd eventually tell you that she's fucking other guys, and that you need to accept it or leave. She'd probably start making you eat their cum out of her pussy, and maybe she'd make you listen or watch. Maybe, she'll even lock you in a tiny little cage too. That's your future Mikey. You'll be Christina's caged cream pie-sucking cuckold." She nearly doubled over from laugher as she finished her cruel hypothetical scenario.
"You'll go from being my bitchboy cuckold to Christina's bitchboy cuckold. God, you're fucking pathetic Mikey. You let me lock you in that tiny pink cage, you've done my homework and errands like a good little bitch, you've listened to me getting pounded by real men, and you've loved it. Shit, you even set that picture of you in the cage as your fucking phone wallpaper!"
Mike felt two inches tall, eviscerated almost, as Olivia finished her torrent of verbal abuse, still sporting a cruel gleam in her eye. görükle escort Would Christina really like him? Would he be enough for her or anyone else? It was pathetic, after all, everything he had let Olivia do to him. Would anyone who had done so many pathetic things ever truly be able to be an adequate lover for anyone? His sense of triumph and confidence from earlier had been shattered as his humiliation and insecurities resurfaced. He knew deep down that Christina was far too nice to do the things Olivia had done to him, and that she liked him, but that did little to assuage his humiliation and insecurities.
"I hope that little reality check reminded you of your place Mikey," Olivia's voice interrupted his thoughts as she sat down on the couch. "Now go get me a bottle of water."
When Mike returned, he stopped dead in his tracks, his heart skipping a beat. While he had been in the kitchen, Olivia had fished his phone out of the pocket of his pants, which were still on the floor. Mike remembered with a sinking heart that Olivia had his passcode because of the events of Sunday night.
"You weren't lying Mikey. You did get her number." Olivia smiled, not kindly. "And now I have it too. And why the fuck are you just standing there?! Give me my fucking water!"
Mike quickly and frantically apologized, handing it to her quickly. This was so out of control. Olivia had Christina's number. He was fucked beyond hope. He could have cried if it weren't for the fact Olivia would have a field day with that.
Olivia ordered Mike to take off his shirt and get fully naked after taking the bottle without any thanks.
"I have you wrapped all the way around my finger now Mikey," Olivia taunted. "Piss me off, or don't answer my fucking calls again, and Christina will see everything."
"Please, I'll be good." Mike begged desperately.
"Oh I know you will be my perfect little bitch now," Olivia giggled. "But just in case you aren't, I think we need a custom video. Made just for Christina's viewing pleasure."
Mike hung his head. He knew there was no arguing. He was in deep shit.
"Get on your knees Mikey," it was obvious she had started recording. Feeling more defeated than ever, he complied.
"Now crawl over here." Again he complied.
"Now show off that pretty little pink cage," Olivia taunted as she prodded it with her foot. "Wiggle it."
Resistance was futile. Shaking with embarrassment, he complied as Olivia smiled with amusement.
"Now repeat after me Mikey. Christina, I'm sorry I have a small dick that could never please you. Say it."
Mike felt closer than ever to breaking down as he obeyed.
"Because my dick could never please you, I want you to lock mine up and fuck real men." Olivia imposed to him.
Mike repeated again, wishing the earth would swallow him whole.
"And I want to eat their superior cum out of your pussy. I want to be your cuckold."
Mike again repeated, his voice cracking and shaking.
"And cut." Olivia said triumphantly. "Such a heartwarming confession Mikey. Maybe instead of unlocking you at the end of the semester, I should just give the key to her."
Mike was past saying anything at this point. She had just about broken him. This bitch was going to ruin everything, and he was running out of options. In fact, his predicament kept worsening.
"I bursa escort bayan didn't catch that Mikey," Olivia said pointedly.
"It's your decision." Mike said with resignation.
"Good answer. I think you deserve a reward."
Great. Another 'reward.'
"You really are a skinny little bitch," Olivia began. "Women want guys who are ripped. So I'm going to let you do jumping jacks for me."
Great. More humiliation. As if he hadn't suffered enough today.
He went on doing jumping jacks for several minutes, his cage flinging all around as he did so, Olivia smirking and shaking her head with amusement every so often.
Finally, she mercifully allowed him to stop.
"I don't know, you're kind of starting to bore me Mikey." Olivia mused. "You get to be around a gorgeous woman way out of your league, and listen to me get fucked. And I'm not really getting anything from it."
Mike didn't like where this was going - he had a nasty feeling she'd send out the videos and pictures if she was bored with him.
"I'm doing your schoolwork," Mike said hesitantly.
"And so can dozens of other people." Olivia said. "You think that makes you special? You aren't special. I'm the hottest bitch on campus. Guys would line up for a chance to fuck me. Do you know how many people I can get to do my work?"
Mike was at a loss for how to respond.
"Ten second to think of a reason to keep you around Mikey, or it gets sent." She turned her phone around, revealing a video message ready to be sent to Christina. Her thumb hovered over the send button.
"Please! I'll do anything!" Mike nearly shouted as he begged harder than ever, his heart pounding.
"Five seconds Mikey."
Mike thought desperately. He couldn't believe he was about to suggest new ways to amuse Olivia and humiliate himself, and beg her to do it. He thought desperately, finally coming up with an idea. God he was pathetic.
"One second Mikey."
"Wait! I've got an idea!" Mike said desperately.
"Let's hear it Mikey," Olivia smirked.
"I'll," Mike started, stuttering briefly, unable to believe how he was about to humiliate himself, "I'll drive you around on your dates with guys." He looked down as he finished, embarrassed.
"Oh my God that's awesome!"
Mike squirmed with shame as he listened to Olivia guffaw at the idea.
"My own personal cuckold chauffeur." Olivia grinned. "Yeah, I like that. I'll get it on with real men in the backseat while you drive us around."
This was going to be so fucking humiliating, especially now that other guys would be directly involved in his humiliation. He was starting to genuinely loathe himself. Christina could never know what a pathetic bitch he was turned into by Olivia. Hell, no one would be interested in dating him if they knew his past.
"Ok Mikey," Olivia said as she deleted the message draft, "I'll keep you around a while longer. I'll let you know when your chauffeur services are needed. Now put your clothes on and get the fuck out. I have a real man coming over to fuck me in a little bit. Maybe I'll think about you. Just kidding, I won't be thinking of you or your little dick!"
Mike left feeling nothing but dread, defeat, and self-loathing. A lovely day had been completely ruined. He wanted more than anything to talk to Christina, but wouldn't even know where to begin. Telling the truth was out of the question, and he wasn't sure what other topics he could try discussing at this point. He decided to simply head home and try to concentrate on schoolwork, desperately hoping he'd get a reprieve of at least a few days from Olivia's abuse.