“I have to admit, you did a pretty good job slut.” Amy said nonchalantly as she propped her feet on Mike’s back, having ordered him to be her footstool. The praise made his nearly leaking and bulging cock twitch against its confines, especially with the sexual connotation of the insult she had just used. “Sure I had to smack and squeeze those balls of yours in the beginning,” she chuckled, her voice having a slight smile in it, “but you got the hang of it pretty quickly. I had you pegged for a fast learner. You nerds usually are.” Her voice was a mixture of contentment and post-orgasm bliss, and it sounded to Mike as if she was stretched out.

Contentment that eluded Mike, who felt burning and pent up energy and arousal, his fierce and suppressed erection driving him crazy, like an itch he couldn’t scratch. This was too much, being caged and teased by this goddess who, unlike Olivia, had allowed him access to her pussy. There was no denying he had enjoyed licking Amy to multiple orgasms immensely, even considering everything she had done to him and planned to do. Her moans as she had quivered on his face, squeezing her legs around his head, grabbing and squeezing his nipples to steady herself as she had climaxed. It had been pain and pleasure horribly intertwined – the cage painfully tight, her grip on his nipples painful, and not to mention his balls had still hurt from her abuse. But he had also felt cresting pleasure that had radiated throughout, which had led to a desire to make her happy. It had simply been an exquisite nightmare.

“You loved eating my pussy didn’t you?” Amy asked teasingly, interrupting Mike’s thoughts.

“Y-yes.” Mike had stammered, trembling as Amy began teasing Mike’s cage with her foot, giggling lightly.

“I bet you wish Olivia would let you lick her like that, hmmm?”

“Yes. I do.” Mike had said with some effort, struggling to control his voice.

“Awww,” Amy said with mock pity, lightly pressing her foot up into Mike’s balls, “maybe I could try to convince her of the benefits. Would you like that?”

Mike grunted from the teasing pressure before answering in the affirmative. Even though he desperately wanted out of this situation, and as much as he had come to despise Olivia, there was no denying that he would enjoy eating her out.

“Oh I just know you would. And maybe I will.” Amy said as she removed her foot from Mike’s cage, something that left him both relieved and disappointed. He welcomed the relief, yet missed the sublime teasing. She knew how to make him vacillate. “I think you should beg me by massaging me. Get before me on your knees.”

Mike struggled to shift to his knees, wincing at the tightness of the device as he did. It took all of his self-control, with that raging locked boner of his, to not lunge forward and start caressing Amy without permission. But he knew better. It was back, that pleasure radiating outwardly from his chest as he prostrated himself.

“Start with my calves. Don’t go above my knees.” Amy said evenly. “Understood?”

Mike said yes, and began rubbing and massaging her calves, gently, up and down. Her calves were so toned and pretty, and her skin so smooth. It took so much self-control not to rub his caged cock against her legs, so much discipline to stay upright as the cage somehow became even tighter. Maybe she would let him hump her legs while caged, but he wasn’t holding his breath. He couldn’t even start to imagine the consequences for doing so unprompted.

It felt so nice to touch her calves, alternating between left and right, rubbing and kneading. So torturously arousing, and Amy’s gentle sighs and moans of pleasure and relaxation weren’t helping, especially when she occasionally prodded his cage with her foot, cackling at Mike’s squirming and gasping.

He simply fought to stay upright, a knot in his stomach, a paradoxical desire to please the cruel woman in front of him burning strong, and above all straining and leaking.

“God I wish your ass wasn’t off limits,” Amy said with lust as Mike switched to her right leg, her left foot immediately finding his balls. “I would bend you over the couch and pound you senseless with your little dick squished in the pink plastic. I would fuck you until you fucking squealed and came in your cage like a locked up little slut.” She laughed before continuing. “I can tell you like the idea of being pegged. And don’t worry, I get to peg you after Olivia pops your cherry. She’s already promised me that. In fact, we’re both going to wear strap ons and spitroast you eventually.”

Mike moaned, a loud and raw moan despite his best efforts, causing Amy to burst out laughing.

“See? Deep down you know this is your place. You love being caged, and you crave being fucked up the ass.” There was real delight and amusement in her voice.

Mike merely squirmed as Amy continued talking.

“You’re basically a joint project now, you know that right?” She smiled. “Olivia’s nominally in charge, which is why I didn’t take you to the adult store when she said not to – even though I really wanted to. I have a sort of friend/mentor who works there, Emily. She’s older – probably around forty – but still oh so gorgeous. She was definitely a bombshell like me and Olivia when she was younger. Do you like the sound of that bitch boy? A hot and dominant cougar relishing in your pink little predicament?” She laughed wickedly, Mike barely able to concentrate on the massage.

“I didn’t catch that.” Amy said, tapping her foot against his cage to emphasize each word. There was only one correct answer, and he said it.

“Thought so.” Amy said with satisfaction. “One of these days when Olivia loans you to me properly you’re going to meet her. I’m taking you to that store and the two of us are going to pick out all kinds of goodies for you. And then, after the store closes, you’re going to pamper both of us. Emily is a very demanding domme. You think Olivia and I are mean? Just wait.”

Mike felt yet another gut punch at that, not wanting to believe it. An attractive older woman teasing him certainly sounded hot – he had all the time fantasized about MILFs after all – but he didn’t think he could handle much worse than Olivia or Amy. If she’d been sensual maybe it’d be alright, if his current tormenters had been more sensual and respectful, he might not have too many objections, much as he hated this conclusion.

“Olivia doesn’t think involving someone so much older is the best idea, but she’ll come around.” Amy winked. “After all, she wasn’t sold on the whole chastity thing at first either. Or pegging, for that matter. If I’m the master, as Olivia said earlier, then Emily is the grandmaster. And there’s still so much to learn.”

Mike gulped at that, preparing to switch legs again when Amy stopped him, telling him to stand up and rub her shoulders. Mike welcomed the change in pace – both because it offered his knees some rest and for the prurient reason that her shoulders and hair were sexy.

“And your hands better not wander,” Amy said sternly as Mike got up. “I don’t want your hands creeping near my tits. If they do I’ll make you sorry. Are we clear bitch boy?”

Mike meekly replied yes as he placed his hands on her shoulders, Amy again moaning quietly in the blissful comfort. He gingerly rubbed and kneaded, Amy rolling her head around on the back of the couch. It sounded as if she had her eyes closed. Mike found himself rubbing and grinding his cage against the back of the couch, grimacing and desperate for any sort of outlet.

Her hair was so pretty, just inches away from his hands, the fresh scent wafting over to him. Combined with her contented vocalizations and the feeling of her lithe shoulders and neck muscles, it was intoxicating. Mike pressed his cage completely into the couch, receiving some minor relief from the aches.

“Keep up the good work,” Amy said seductively, “and I might unlock that cage and let you cum. Olivia gave me the key before she left.”

Mike moaned involuntarily, inadvertently tightening his grip on Amy’s shoulders, prompting her to tell him to loosen his grip. Mike did so, quickly apologizing.

“I bet you wish Olivia would let you massage her too,” Amy said, ignoring the apology. “All her enthusiasm for chastity and she still hasn’t fully learned how to take advantage of having her own personal bitch boy. Getting your pussy eaten whenever you want, massages whenever, anything. When I had my loser locked up he was giving me full back rubs every time he visited me. I even had him towel me off after I showered and brush my hair. It was great, and it gave me the added amusement of driving him crazy.” She chuckled fondly at the memory. “I even let him put his hands on my tits at one point. I just know you’d love that, and who knows, maybe one day I’ll let you. But you’ll never get to fuck me. You know that right?” There was amusement in her voice.

Mike found himself whimpering as he said yes, making small circles with his thumbs as he continued to massage her, that strange desire to please her getting stronger.

“Poor boy,” she laughed as Mike continued rubbing. “But you will get to be fucked by me.” She laughed hard at the distinction. Mike simply twitched, beyond words. There was something about standing behind his tormenter, having his hands on her shoulders and near her hair, as she talked so nonchalantly about her planned future humiliation of him.

“Tell me, have you thought about what color strap on you’re going to be fucked with?” There was a smile in her voice now.

“Purple?” Mike offered, knowing she wouldn’t accept a lack of an answer.

“Maybe from me. But not from Olivia. She plans to get a black one,” she laughed. “She thinks it will be more humiliating. But I plan to use something bright and neon. Maybe purple. Or maybe pink, so it’ll match your cage. Maybe I’ll even hold that pink cock next to the cage, and compare them.” It was clear that she was getting incredibly aroused by the wondered of it all. Mike, too, found himself no longer able to relieve any pressure by grinding against the couch.

“But as humiliating as all that might be, it won’t be as bad as your first time with a guy.” Shit. There it was again, and it sounded as if there was a definite plan that Amy was privy to. Mike felt a pit form in his stomach, and tried to simply focus on rubbing her shoulders.

“Oh yeah, we’ve got it all planned out.” Amy said as if she’d read Mike’s mind. “I’ve got a friend who’s bi. You’re going to watch as he fucks me. Then, while he recovers, you’re going to clean me up, and lick up that creampie while Olivia watches. And then you’re going to slurp all of my pussy juices off for his thick cock while Olivia grabs your hair and makes sure you bob your head back and forth like a good slut. God, I can’t fucking wait.”

Mike felt his hopes wilting. It seemed as if he was indeed doomed to lose what few vestigial shreds of dignity he had left if he didn’t escape from his predicament soon. But how to escape without being exposed?

“I can tell you’re getting hot and bothered by all this bitch boy,” Amy snapped him out of his thoughts. “You’ve been fucking humping the couch ever since I let you touch my shoulders.” Her laughter made it clear she wasn’t angry about it.

“Tell you what,” she continued, “I’m going to give you a chance to cum. Here’s what we’re going to do. First, get back on your knees in front of me.”

Mike actually found himself slightly disappointing as he abandoned the massage and close proximity to her, once again subjecting his knees to discomfort – although he was definitely happy to have a chance to orgasm. Operative word being chance.

He got on his knees, painfully aware of how exposed he was as he spread his legs as ordered.

“So,” Amy said happily as she produced the key, “here’s how this game is going to work. You’re going to balance this key on your nose.” She stopped to gain control over her laughter. “And if you can balance it for two minutes, I’ll unlock you and jerk you off until you orgasm. Sound good?”

It wasn’t as bad as Mike had expected, although it would be embarrassing to essentially balance something on his nose like a circus seal. But compared to other humiliations, that would be very mild.

“Head up,” Amy commanded. “Before we begin, how about you clap like a seal for me, since you’re balancing it on your nose.”

Mike did his best to ignore her delighted laughter as he complied. Finally she reached forward and placed the key on his nose.

“And begin!” She exclaimed. Mike was determined to remain still. To not let this opportunity pass him by, even as Amy tried to distract him by moaning.

“Halfway there,” she said teasingly.

He could do this. It occurred to him that she might make him cum in a degrading manner, or perhaps even ruin his orgasm. But it was a chance he would have to take.

“Thirty seconds.”

It would really suck to come so far just to come up empty.

“Ten seconds.”

“Nine.”

“Eight.”

“Seven.”

“Six.”

“Five.”

SMACK.

Mike felt an explosion of pain in his balls as Amy’s foot connected hard. He lurched and fell forward automatically as he groaned from the pain, the key falling and tumbling to the floor.

“Oops!” Amy squealed with laughter. “I never said I wouldn’t interfere!”

Mike writhed on the floor, this blow far worse than any of the previous blows, forcing himself up reluctantly as Amy directed him up through her laughter. The blow had had the merciful effect of temporarily alleviating his craving for pleasure, but at the cost of a far more unpleasant sensation.

“Aww,” Amy said mockingly, “looks like it’s no orgasm for you. For what it’s worth, it was going to be a very humiliating orgasm. I was going to have you lay down with your legs up, and jerk you off until you came all over your face. But maybe even that would have been better than more denial. Guess it depends on how you feel about it. Now hand me that key.”

Mike reached down to pick it up. That key, that tiny object that could give him his freedom. He could just unlock himself and run, he wondered. Sure Olivia would ruin him in return, unless he threatened to take her down with him by exposing her academic dishonesty, which he was complicit in. The best he could do was threaten an internecine struggle, mutually assured destruction. But who would be harmed more? Assuming they were both expelled over the cheating, Mike’s reputation would also be utterly destroyed. He’d probably lose his family and friends, maybe even get kicked out of the house. Olivia, meanwhile, would probably just become a trophy wife and land on her feet. Sure Mike could argue that he had helped Olivia cheat only under duress, and it probably would have worked. But it was ultimately a game of chicken, and Mike didn’t have the stones for that. And so he was fully prepared to simply hand the key back to Amy.

It would be so psychologically torturous to literally hold his freedom in his hand, only to return it to his captor. He was about to pick it up when Amy stopped him.

“Actually,” she said with an amused smile, “use your mouth to pick it up.”

She giggled as Mike pressed himself flat again the floor, once again managing to feel more lowly somehow, getting his teeth on the key as Amy laughed derisively.

“Don’t swallow it!” She taunted through her laughs. To his chagrin, he was still hard in the cage as he offered the key to Amy, who took it from his lips after several seconds of mockery, ordering him to be her footstool again.

It was mostly quiet now, Amy on her phone, her foot occasionally teasing his cage.

“I can tell you’re all worked up from rubbing my legs and shoulders. I just know you’ll be equally bothered at Cancun when I have you apply my sunscreen. Just imagine, I’m in a bikini, laying on my stomach on the towel. You’re still cramped in that little cage as you get next to me and rub your hands all over my beautiful back. Some people might think you’re lucky. If only they knew what was really happening. Your dick is in something pink alright, but not my pussy.” She laughed at that, Mike indeed aroused at the wondered of applying sunscreen to her back. He was no longer sure who was worse – Olivia or Amy.

Amy’s phone chimed. A few seconds later she laughed excitedly and knowingly.

“Oooh,” she laughed. “Olivia’s bringing some company here after her class finishes up. Get ready.”

Mike felt his heart skip a beat, a pit of dread forming in his stomach. Please don’t be anyone I know, he said to himself. Please don’t be Christina, even though he knew his chances with her were fading fast.

Mike simply remained in a state of supreme anxiety as the minutes crawled by, his heartbeat quickening as he heard the door open. Seconds later he heard a startled gasp, followed by nervous laughter.

“Oh. My. God.” Came the incredulous gasp from a woman’s voice that he did not recognize.

“I told you I wasn’t lying,” Olivia said with smug satisfaction. “Which means I win the bet.”