No F-ing Way! Pt. 03

Grinding every which way with his ass planted against the box, impaling the phallus deep inside him, he started to feel a little desperate when he reached the plateau of the sensation that he could get against his prostate. He felt that maybe it was getting desensitized from the repetition and gave himself a break. He realized he was hot and covered in a sheen of sweat as he sat on the box panting. Was he . . . disappointed? He leaned forward with his hands on his knees to catch his breath, and as he did he felt his ass slide up on the dildo just a little bit and it was a whole new sensation compared to the grinding. The grinding wasn't bad. It had actually felt really, really good, but he thought that maybe he had just gotten used to it. The sliding though. Oooohh, that felt really good.

He shifted his legs back for some leverage and leaned forward onto his palms. With the shift in position, his ass lifted off of the box, and the moment that it broke contact, the entire chastity cage rumbled to life with a steady thrumming of vibration. He drew in a sharp breath, his eyes bulged and his mouth shot open. He dropped back down onto the box and gyrated lustfully into the dildo, feeling more pleasurable sensation build up in his ass and around his engorged, yet restrained, cock. Uuuggghhh, he, thought, soooo good. How had he gone this long in life without discovering how much pleasure there was to be had back there? He felt like he might be able to get enough stimulation to cum with the vibrating, but as soon as he thought it, the sensation cut out.

His cage had gone dormant. "No!!" He yelled as he looked down and clutched at himself. "No," he whimpered, a little more deflated.

He shifted and gyrated and rocked, trying to get the cage to vibrate again. In a final, frustrated, desperate act he lifted his ass off the box and thrust back down on the cock again, and as soon as his ass had reestablished contact with the metal on the box, the cage sprang back to life with waves of pleasurable vibration. "Oh, thank god," he muttered to himself, having forgotten that the camera was there. The vibration got his hips going and he felt his balls start to stir. "Yes," he said under his breath, "yes, yes, yes, yes," and then, after a few more seconds, the cage went dark on his once again. "No!!"

Almost on instinct this time, he lifted his ass of the box, not even noticing the absence of any shock when he did so. He slid back down on the shaft, hardly daring to hope, "please, please, please," he repeated under his breath. As soon as he was seated fully back down on the cock, the vibrating started up, and he threw his head back in exalted relief. "Oh, fuck yeah . . . yeah, yeah," and without missing a beat he was rocking and grinding, reveling in the building pleasure. When the cage went dormant again, he didn't even think about it when he rode himself up and down the cock one more time, rewarded by more vibrating once he made contact with the box. He collected all of his focus into keeping the wonderful sensation going. He felt like he had a rhythm now, cage stops, ride the shaft, cage vibrates, feel gooooood. Cage stops, ride the shaft, cage . . . cage . . . nothing.

"No! Come on! Unnhhhh, I'm soooo close!" He felt the orgasm that he was sure had been just around the corner start to slip away. "Dammit!! Hey!" He called out. "Hey! Please!!. It stopped working again. Come on! Please?!! Can't I just have a little more of the vibrating? It's not . . ." he fell silent. Working. He finished in his head as he looked over to the next box, and the next, larger, cock that was waiting ominously for him. He hung his head and slowly lifted himself of box number two.

He realized that he had completely lost track of time. He stretched out a bit, and didn't even notice that he wasn't getting shocked. He stepped over to box three with the lube in hand, and as he started to step over the side of the box, he saw a bottle of water behind it. Hmmm, thoughtful, he told himself. He unscrewed the top and took a few deep gulps.

Hydrated, he refreshed the lube on his ass and slid some over the phallus on box three, absentmindedly stroking it for at least a bit longer than was truly necessary to make it slick. He was excited with anticipation as he positioned the new, slightly fatter tip against his ass, and he relaxed himself like a natural, almost enjoying the stretch as he worked the head inside of him. He sighed as he felt himself slide down, and knew to anticipate the resistance when this third, longer dildo plunged to new depths inside him.

He adjusted and smoothly pushed himself down further, "please, please, please, please" he found himself repeating. He felt renewed pressure on his prostate as the thicker cock slid into him. A thankful "Yesssss!" was out of his mouth before he could stop it when the cage sprang into its vibrations once again the instant his ass was seated on the metal pads on the box. "Oh, thank god." He looked at the camera, "thank you thank you thank you," he mouthed as he ground away. He was fuller, but it was starting to feel soooooo gooooddd.

He lifted his ass off the box, almost greedy for more sensation, but the moment he did the vibrating stopped. "No!" he exclaimed and dropped back down right away, rewarded with a low hum as the cage sprang back to life. He tested it again. It seemed that if he lifted himself off too soon, the cage would stop, so he adjusted his efforts and ground and gyrated and circled his hips, lusting in the vibrations. The second they stopped, he would lift himself up and slide back down to trigger it again. The timing of the routine seemed to draw out the building of pleasure, and ever so slowly coaxed him back to the brink of orgasm. Just when he was sure that a few more thrusts, coupled with the vibrations, would get him there, it stopped again. He wanted to cry. "Please?!" he looked at the camera, "Please?! Ok. Okay. Okayokayokayokay!"

He gingerly lifted himself up. Took another swig of water and stepped over to the next box. He lubed up the dildo, and then stopped when he realized how mindlessly he had gone from one to the next. Looking back the first one had been pretty small, but it had seemed monumental to pop his cherry, so to speak. The others were each incrementally larger, but now, this fourth one. Holy shit, he thought as the stroked it, working the lube over all of its surfaces, this is getting pretty substantial. All he knew was that he wanted to cum, maybe more than anything. It was harder to get this one inside of him, but he was determined, and started to get excited once he had made entry and felt himself sliding down. He was vaguely aware that he was almost forcing himself down on it like a greedy slut. Ffuuuccck, he realized, I'm a greedy cock slut, but shrugged off the self-doubt. He just had to cum. He was waiting to greet the vibration as he was nearly fully seated on the dildo, and when his ass met the box . . . nothing. "Hey!!" He yelled at the camera. "Hey! What the fuck! Come on!!" He sat there impaled on the cock, almost ready to cry. "Please?! Let me fuck the cock, please!!"

Oh shit! He froze, realizing how dangerously close he was completely caving on the first part of the bet, begging for cock. He look over to his side. He reassured himself that he really hadn't even lost the first part yet. After all there were still two larger cocks down the line. He wasn't begging for the biggest cock yet. He sighed. He wanted enough stimulation to cum so badly. "Please?" He looked at the camera.

And the room went dark.

"Hey!!" He yelled into the blackness. "Hey! What's going on?!" Silence. Sitting in the darkness, he realized how tired he was. How long had he been at this? Hours? He started to feel a little silly sitting on the box in the dark. "So, what is this now?" He called out. "Lights out? Bedtime or something?" Silence. "Fuck" he muttered under his breath before lifting himself off of the fourth box. He leaned down, reaching to find the carpet, and carefully lay down. "Ohhhhh, fuck," he muttered. "What . . . the fuck . . . is going on here?" He curled up an arm and lay his head down on his shoulder. "Okay, time for some rest," collecting himself, "This isn't over." The throbbing soreness almost felt good. A sexual sensation that was new to him, flush and sore after getting fucked. He couldn't help but smile a little as he drifted off to a fitful sleep, laced with dreams of gyrating hips and fucking and rubbing at himself.

********************************************

He woke squinting his eyes shut at the onslaught of light in the room. "Aagghh," he knew he must have slept, because fleeting images of riding huge cocks were already drifting from his memory, becoming less vivid by the second. He recognized them as fading dreams. Dreaming of cocks? He questioned himself but shrugged it off. He forced his eyes open a crack to find himself right where he was before. Same room. Some boxes. Same cocks. He was also acutely aware of the equivalent of 'morning wood'. He wasn't sure if it was morning. He had lost all sense of time, but the effort his cock was putting into springing free from the chastity cage was painful. "Uuunnnhh," he groaned. He wanted relief. He wanted to fuck. he slowly got to his feet and stretched out a bit.

"Anyone there?" Silence. "Hello?" Nothing.

He sighed and looked back at the boxes. He was on number four, or at least he had been before the room went dark on him. It seemed as good a place as any to start. Repeating the process from before his slumber, he lubed himself up, noticing that the hole of his ass was still a little puffy, and then slicked up the fourth-largest dildo. "Here goes" he said, as he positioned himself over it and slowly lowered himself down. He winced a little bit, having tightened up while he rested, but his body adjusted quickly. After carefully raising and lowering himself a few times, reveling in the pressure on his prostate, he was able to finally seat himself down fully on the box. He was rewarded with the sweet feeling of vibration, "Thank god." He muttered. Right before the vibrating winked out on him.

"Wait! Why?" He looked at the camera. "Come on!!" He whined. "I was good! You didn't even have to shock me." Nothing. He looked at the next largest dildo. It couldn't be that yet. Her system seemed to have him on each one for a while, and he had only reached this fourth box at the very end of the night. He look back at the third box. That didn't seem right either, and the one he was on seemed to have registered when he first settled down on it. That fact that he was anxiously trying to figure out which cock to fuck went completely over his head. He looked at the camera.

"I don't get it. What am I supposed to do?" He repeated, "What am I supposed to do?" He sat there, impaled, thinking, trying to figure it out when he remembered the bet. Oh my good lord, he thought to himself, I can't believe how much she manipulated me. Wow. He shook his head from side to side once. If I'm not going to be able to get off, fuck this. He raised himself off of the phallus and stepped off of the box. He didn't want to make a big show of it. Maybe she had forgotten or was distracted. If he could just ride this out, he'd win the bet. He thought about the five thousand dollars in his pocket and the revenge he'd exact with Allison as his sex slave. He took a step behind the boxes, trying to stay out of sight from the camera and quietly laid down, wondering how much time was left.

He was almost bored when he felt it again. Tingle. He shot up to a sitting position. "No!" he yelled out. Tingle.surge. "No NO NO NO NO!!" Tingle.surge.tingle.surge. "OK! OK!" waving his arms in front of the camera, no longer hiding from it. "OK! I get it! Getting back on the box! Getting back on the box. Riding cock! Riding cock!" He tried to exert a little control by being good-natured. He expected the protocol to start up again after he was fully-lowered and impaled once, but this time . . . nothing. "Come on!!" He exclaimed, "What do I have to do?!" He sat there, frustrated for a minute before he heard a click as the door handle turned. He was hopeful. Holy crap? He hoped against hope. Did I make it? Is it over?

The door swung open a crack, and a small bit of cloth came cascading through. The door had closed almost before the projectile hit the ground, and a second later he heard the click as it locked shut again. He stared down at the ground where the fabric had landed and recognized it immediately.

Panties. He sat there and waited. No shocks. No prodding him into compliance. Nothing but an ass full of cock. He folded his arms across his chest and started stubbornly at the undergarment on the ground by the door. No fucking way, he thought. He had suffered and humiliated himself enough. Enough barriers had come down. He was ready to just wait this out. A little buzz of vibration sent feeling of pleasure straight to his core but he waited it out. After a pause, it started again and he forced himself to sit still, even though it felt good. Really good. After the next pause came the shocks. "No! Fuck!! No!! Ok! OK!" He lifted hips off of the box and thrust back down, "I'm fucking, I'm fucking! See?!!"

She shocks stopped, and after a pause, the vibrating began again. It was with a little bit of trepidation that he embraced the pleasure, because he knew what it was going to do to him. It would make him desperate for relief. Desperate to cum. But between having one's balls shocked off and getting horny, he'd take horny, and in no time, after a few cycles of heavenly vibrations, he was blissfully horny . . . and then the vibrations stopped.

Panting on the edge, feeling the orgasm slip away from him yet again, he looked back over to the panties on the floor. His chin dropped to his chest in defeat as he stood up off of the dildo and swung his leg over the box. He walked over to the door and picked up the panties. They were satiny soft, pink with some lace embroidery. He shook his head as he carefully stepped into them and pulled them up his legs. As he did so, he noticed that they almost gave the impression of a caress as they slid over his skin. After the strain and intensity of the boxes, they felt almost soothing. "Ok" he said quietly. "Here goes".

He swung his leg back over the fourth box, straddling it. He felt the fabric of panties rub against the little bits of skin poking through the openings of the cage and shuddered at the sensation, almost like a

soft kiss grazing along the bits of exposed flesh. He looked at the camera and grimaced as he reached back and slid the panties to the side of his crack, mounting the cock like a pro now. He lowered himself down with less resistance than before, and, thankfully, he was rewarded with a vibrating chastity cage once he was seated down on the box. His eyes fluttered shut in relief, and he tried to just enjoy the feeling without focusing on the panties he was wearing.

They cycle continued. A duration of vibrating would follow each ride up and down the shaft, and it would last long enough to start building him towards the edge. If he rose from box too quickly, it would cut out, and he'd feel the building sensation slip away. He had no choice but to be driven gradually into a higher state of lust. The first round of sitting down for the vibrations would be longer, awakening his need to cum. The vibration would always stop without giving him enough time to really let it build, forcing him to slide up and down the cock again to re-trigger the cage. The buzzing sensation would get him a little closer, but not last quite as long as the one before, forcing another thrust. He'd find himself a little closer, only to have the vibrating cut out a little sooner; another thrust.

Each sequence would gradually coax him from sliding up and down the cock and pausing, to a constant fucking, with the timing and duration of the vibrations driving him to the very edge of orgasm. Once he was at the edge though, it would stop entirely. Try as he might to shift and ride and stroke, he just couldn't get enough stimulation to cross the threshold. So, he would beg . . . and plead . . . for the next item of clothing.

He quickly figured out that each new garment would unlock a new cycle of pleasure. Time passed on box four and he found himself a desperate mess. No stimulation and no new garments something through the door. "Hello? Please?!" Silence.

"Come on! Please? Can I have something else?" Nothing. He looked down at himself. He wasn't sure what else there could be for him to wear. He was already wearing panties, thigh-high stockings with garters and a belt, stiletto heels (it was an ordeal to stumble back to and mount the box in those!), short leather skirt, bra, halter top, thick pink leather collar, wig. "What do I have to do next?! Please!!" Silence.

He had learned. It was time to move on to the next box, but he really didn't know what was left for him to do. Resigned, he lifted himself from the cock in his ass and felt regrettably empty. He sighed and stepped over to box five. He thought that maybe box four had hosted a cock that was about his size, more or less (may a tiny bit bigger, if he was being honest), but box five was truly well-endowed. He had surmised that he was probably about average, but this was definitely . . . .bigger. He grimaced and just got on with it. Lowering himself down and gasping as it slid into him. He felt almost like he had to pee as he pushed himself down, and he checked himself to see that he was indeed leaking, but it was more precum, oozing out in a long stringy stream. He scooped it up and licked it from his fingers without even thinking about the camera this time.

The amount of time to complete the transfer to cock number five had allowed the oh-so-close orgasm to slip away from him once again. Once he was fully seated on the box, he shuddered with relief once the vibrating started. When it stopped he wasn't sure what to ask for. "I don't know what to do!" He called out. "What else am I supposed to wear?" He sat patiently, helpless . . . broken.

The door cracked open and he perked up expectantly. An open box slid through along the floor before the door clicked shut again. He winced as he slid off of the large dick that had seated deep inside him and hobbled to the door. He recognized the makeup container and brush that were in the box for what they were. They were placed on top of a round mirror with a fold out stand. He picked them up and saw a pink sheet of paper folded up on the bottom of the box. He set down the make-up and mirror and unfolded the paper. Application instructions . . . . He proceeded to read carefully written out instructions on exactly how to apply the make-up. He was so far beyond protesting at this point. Looking around the room, he didn't see any place where he could really set up the mirror, and ultimately decided to set up the mirror on the first box. He knelt down in front of it to try and follow the instructions. He wasn't sure he had gotten it quite right, but did his best. Once finished, he returned to box five and mounted himself on the second-largest cock in the room.

The devious thing about this phase of the system was that the retrieval, instructions and application of each bit of make-up took longer than each item clothing that he donned when he was on box four. Each time he took the phallus back inside him, he needed more time, more riding up and down, more stimulation to get close to the edge. Hours of riding and fucking and stimulation ensued before he had applied base, blush, lipstick, mascara and eyeshadow. The last item to come through the door was a set of press-on nails. When he returned to box five and pressed himself down, the bet was the farthest thing from his mind, He had been conditioned to just try and unlock the key to get just a little more stimulation. He seated himself down on the box, making full contact with the conductive pads, and he got nothing.