He debated whether or not to leave, but decided that doing so would probably displease her. He needed to stay on her good side, given the mounting ammunition she had for blackmail and that last night had been a bit rocky between them at times. He decided to go over the top in staying on her good side, starting when she woke up. It would make him feel like a simp, but he knew he couldn't let pride guide him at this time.
Biding his time, Mike sat up on floor, willing his dick to become soft. He had finally succeeded when he heard Olivia stirring in bed.
"Morning Mikey," she grinned as she sat up in bed.
"Morning," Mike answered back. Already, he could feel the cage begin to tighten again. Dammit.
"How'd you do on those tests?" She asked, still not entirely awake.
"A's on both." He was telling the truth. They hadn't been that hard. He wasn't sure if she would actually have a reward for him, but decided it wasn't wise to ask.
"Good boy," she purred, stretching her arms and yawning. She was in a good mood, and happy with him. Now was the time to take advantage of that momentum.
"Do you want me to get you breakfast or something?" He volunteered as he stood up. He had time to kill anyway, and figured he may as well use it to earn some good boy points with the mercurial hand that held his key.
"That cage has really turned you into a good boy Mikey!" She beamed. "Of course you can. For being such a good boy, I'll buy and you can get yourself something too. Aren't I just so nice?"
Mike replied affirmatively and voiced his thanks. He hated eschewing all dignity like this, but he hoped it would pay off.
"I'm going to take a shower while you go do that. Wouldn't you just love to see that?" Olivia stood up and cocked her head to the side.
"Yes." Mike groaned truthfully, straining in the cage. She may have been a vapid and superficial bitch, but there was no denying she was gorgeous.
"Oh I know you would," she giggled at his obvious arousal and discomfort, "but you definitely haven't earned the privilege of seeing me naked. I don't think a guy in a pink cock cage ever will. No offense." She laughed again.
"None taken," Mike lied as he got his wallet and keys.
"Oh, by the way, don't use the drive-thru. I want you to walk into the lobby all locked up." Olivia giggled at his expense again.
"I will." Mike replied, the cage continuing to tighten. God he hated that any of this had him hard.
"Good boy. And just think," Olivia said seductively as she approached him, "while you're out and about in the cold morning, I'll be naked in the shower, hot water running down my body and through my hair. That should keep things nice and tight down there, if they aren't already." She smirked and ran a hand over his groin, causing Mike to groan in frustration.
"Oh yeah," she laughed, "nice and tight. And pink." She giggled as she handed him a twenty. "Now be a good boy and fetch breakfast. I want a McMuffin."
Mike was largely able to concentrate and stay at peace as he conducted this morning errand - even going into the lobby wasn't that bad. It wasn't like he hadn't previously entered a store while locked, although the click of the lock was always a terrifying sound to him, and he was still dreading class and work, which he knew couldn't be avoided forever. In fact, he had class tomorrow. And Olivia, Anthony, and Christina were all in that class. God, what would Christina think if she saw him in this pathetic state? He swallowed as he thought about it.
To Mike's chagrin, he once again felt himself trying to get hard as he returned with the food. Why was he so aroused by this?!
"I'll be down in a minute," he heard Olivia call from upstairs, "I want your pants off when I come down."
Mike quickly replied that he would comply, and quickly did so with shaking hands. He had hoped she wouldn't humiliate him just this once, but it had been stupid to expect anything else when she so clearly relished in his humiliation.
It had only been a couple of minutes when she came down, dressed in a pink sweater and a pair of yoga pants that accentuated her stunning ass.
"Like what you see?" She smiled and raised an eyebrow.
"Yes. Very much." Mike stammered. Again, he was telling the truth. As conflicted as he was about all this, he knew she was incredibly hot.
"I'm wearing pink too," she giggled as walked to the couch and sat down. "The only difference is I can take mine off whenever I want."
Mike shuddered and involuntarily grabbed his cage, as if that could soften his caged cock.
"Isn't that right Mikey?" She teased as she unwrapped her sandwich.
"What's that?" She asked coyly. She never made this easy. She always had to emphasize his predicament in the most humiliating fashion. Once again, he found himself feeling a strange mixture of hate, angst, and guilty pleasure.
"You can take off the pink sweater whenever you want. I can't take off the pink cage." Mike swallowed his pride. Again.
"That's right, you can't." Olivia shook her head and grinned. "Because I hold the key. And I decide when it comes off. And that's not going to be for a while."
"As long as you want." Mike said with resignation.
"You're being such a good sport today Mikey!" Olivia praised him in an almost patronizing tone. "For that, you get to eat breakfast with me." She patted the couch next to her. He really was just a pet to her. How was he going to salvage his self-esteem now? This mean Queen Bee was going to do emotional damage to him at this rate. He hoped the comfort food would take his mind off of it.
"It's so much easier this way," Olivia said as Mike took a bite out of his sandwich, "when I don't have to punish you or remind you of your place. Keep it up and I'll definitely let you cum in a couple of weeks." Mike's legs twitched involuntarily at that, causing Olivia to giggle again.
"Have you ever gone that long without cumming Mikey? What's the longest you've gone?" She wasn't going to accept anything less than a clear answer, that much was clear from her tone.
"Only a couple of days." He answered honestly. He had never had a reason to hold out.
"Oh this is going to be a tough ride. I have faith in you though!" She taunted.
Before Mike could think of anything to say, she continued.
"By the way Mikey, great job on those exams. I am VERY pleased." It was clear she truly was. "You definitely make up in brains what you're lacking between your legs." Great, more embarrassment welled within him. She couldn't just compliment him and leave it at that. Why couldn't he have been approached by literally any other girl at that party?
"And you have definitely earned that reward I had in mind." She said with a mysterious smile. Mike perked up at this, although he refused to get his hopes up. He knew they would just be brutally dashed. "Excited?"
"Yes. Thank you." He had to feign satisfaction, even if it was a lousy 'reward.' He didn't want her to make his life hell.
"I bet," she said in an amused voice as she stood up. "Doesn't my ass just look fucking amazing?"
"Y-yes." It really did.
"Get on your knees." She ordered curtly. He quickly did so, and she turned around so her ass was in his face.
"I bet you would just love to fuck it, but you know that'll never happen don't you?"
"Y-yes," Mike looked down at the floor.
"Would you like to sniff it though?" She asked with amusement.
"Yes." Mike gasped. Humiliating as it was, being this close to such a beautiful ass, even clothed, was undeniably sexy. And he knew saying yes was the only acceptable answer.
"Ok Mikey, you can put your face in my perfect ass for thirty seconds. Starting...now!"
She reached around and pressed his face into her ass. Loathe as he was to admit it, it did feel amazing having his face in such a beautiful ass.
"Oh yeah I bet you just fucking love this," she said aggressively as she pushed his face in harder. "I bet you're almost ready to explode in that little pink cage. Aren't you?"
Mike gave a muffled response.
"I'm glad you're enjoying it, because this is the closest you'll ever come to fucking my ass. But I think Tyler will be fucking it later tonight. He gets to fill my ass with his huge cock, and you get to sniff my ass while your little dick is locked away. Maybe I'll let you listen on speakerphone tonight, hmmm?"
Even as Mike's dick continued to surge to his embarrassment, his heart sank. He needed to get school work done tonight. Before Mike could even respond, though, Olivia put her foot under Mike's cage and prodded it, causing Mike to moan into her ass, to her great amusement.
"Oh I can tell you just fucking love the idea of that Mikey. Don't even try to deny it - your cock is absolutely straining in that tiny cage." She teased. "But I don't think you've earned that yet. You'll have to be a very good boy to get to listen to Tyler pounding me."
Mike felt catharsis that he would have as normal a night as he could (hopefully) but didn't let it show.
"And time's up," Olivia's voice disrupted his thoughts. She released his head as she turned around. "What do you say Mikey?"
"Thank you." It was unreal that he was thanking a spoiled diva for mocking him and treating him like shit, but here he was.
"You're welcome," She laughed. "Was that the closest you've been to being inside a woman?"
"Y-yes." Once again, humiliation welled inside him. He'd always been insecure about his virginity, but this constant shaming had catapulted his insecurity to new heights. She was making him hate himself.
She laughed and shook her head as she played with his cage. "And this is the closest you've come to having your dick inside something tight and pink."
Mike affirmed. When else could he do at this point? He was becoming nothing but a sponge for her mockery and abuse.
"Poor Mikey," she smiled as she shook her head. "You might get proper pussy one day. Maybe. But it won't be mine. Maybe that Christina would. But she would never go anywhere near your dick if she ever saw those pictures I have of you. So keep being good." She let go of his cage.
"Have I been good today?" Mike hated to keep going lower and lower, but he was desperate to avoid having those pictures leaked out, and wanted to guage where he stood.
"Oh yes, very." She giggled. "So keep it up."
"I will." Mike said. He certainly didn't want the one classmate he possibly had a chance with to become privy to his degradation.
"Good boy, now put your pants on and go home. I have other stuff to do. I'll see you in class tomorrow. I'm looking forward to it," She said with a disconcerting gleam in her eye. "And you can keep the change from breakfast. Daddy always taught me to tip the delivery boy." If only her dad had taught her other morals, or if he had, if only she followed them.
"Oh, and Mikey," She called out as he was at the door, "be sure to wear a pink shirt to class tomorrow."