Author's Note: I've edited it for content thanks to some of the feedback that I have received. I really appreciate any and all comments!
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It didn't take long for him to go from drinking afternoon coffee with her to desperately gulping down her golden stream, as she tormented his cock. She was rather detached in her approach and when she showed any kindness, it was only to double the pain. Today was the fourth month of their agreement and it had gotten progressively more intense; her creativity and ruthlessness usually culminated in tears and cum. She liked it when he broke down and begged to cum, even when she promised it would only bring more pain and humiliation.
Today was special. He had endured so much to please her, and today was the day when he would prove just how fully he was committed to her pleasure and enjoyment. It was also the make or break moment for them to go forward on a more full time basis. If he survived.
When he arrived at her home, he let himself in without knocking. He immediately went upstairs to the bathroom and took a long hot shower, scrubbing himself thoroughly, gingerly washing around the spiked cock cage. The lead ball stretcher was loose enough for him to slide a soapy finger through and he briefly enjoyed the feeling of massaging his ball sack, lightly pulling and fondling before jerking upright and glancing around surreptitiously, as though he had been discovered.
The mistress was not home. She had instructed him to make himself ready for her before she returned, and he would comply, or she might simply turn away and ask him to leave. That way lie madness and he shuddered at the thought. Returning to the task at hand, he finished the shower and took the enema bag hanging nearby, and filled it with warm water. He hated this part, and knew that she liked the deep embarrassment that it brought him. He inserted the dildo-shaped nozzle into his ass and opened the valve to allow the water to enter his rectum. He endured the cramping bloated feeling and grabbed his phone in order to take a dutiful photo, and sent it to her-- proof that he would be completely clean, as she demanded. His cock twitched and strained at the delicious degradation of preserving his abject state. He prayed that she would be pleased.
After twenty minutes, enough time had gone by that he felt he could void his bowels. He had been instructed not to gain any relief from the sensation, and so pressed the spikes of the cock cage into his shaft. Perversely, the combined feeling of the water forcefully leaving him and the bite of the spikes made his cock stiffen despite the confines of its prison. It left him light-headed and he was reduced to bending over and letting his head hang between his knees, as he straddled the toiled bowl.
He had been daydreaming. Jumping up from the toilet, he panicked for a moment, thinking that he had been there so long that she might have returned before he had made himself ready. He looked at the clock and saw that he still had time, but it would be close. Quickly, he cleaned up the area and himself...realizing that pre-cum had oozed out while he had been lost in his fantasies. He hoped she would not be displeased and debated wiping himself off, which was forbidden. He was only allowed to do so in her presence and then required to lick his hands clean. The spikes bit painfully into his straining flesh, as his cock pulses at the thought. He shook his head to clear it and ignored his traitorous appendage.
He went back downstairs into the back bedroom which was spacious enough to hold a number of contraptions and had a walk-in closet, where the mistress kept her toys and implements. He saw some packages sitting on the floor and wondered if she had purchased something new for his special day. It made him giddy to think that he might be worthy of that. Grabbing the cuffs stored in his personal cubby, he fastidiously inspected them before putting them on his ankles, wrists, and throat. He then pulled on the sensory deprivation hood, adjusting the ear pieces so that they completely muffled any noise. Slowly he felt his way along the wall, until he was stopped by something. Reaching out, he moved until he could sit on the surface. He was proud of the fact that he could do this without requiring her directions. It had taken a lot of whipping and practice to get to this point. She had high expectations of him, and he aimed to please. Fumbling a bit, he snapped the chains to the cuffs at his feet, then to his neck. He was able to get his left hand restrained but the short chain did not allow for him to complete the task. He tucked his hand under his butt and waited for her arrival.
Sometime later, he was awakened by a stir in the air. His nipples crinkled, reacting to his anticipation. He adjusted his position, suddenly crying out as he dragged his dead hand and arm out from under his ass. Whimpering, he flailed his hand as the pins and needles brought sensation back to it. How long had he been sleeping? Was the mistress still gone? Had he done something wrong?
Crack! His body arched upward, a scream tearing from his throat as the white hot fire of the whip brought him completely awake. His free hand was yanked upward and restrained swiftly, then a quick pat on the side of the cheek let him know that his special day was about to begin.
He knew the mistress was speaking to him, but he also knew that she required no response from him. If she wanted his opinion, she would give it to him. His nipples crinkled in fear at the thought. He liked to imagine what her thoughts and expressions might be as she did her work. What would she do first? Would he be allowed to pleasure her? His cock came to attention and drooled in response to the mental image of her draped over his face, his tongue busy at work deep in her cunt.
Crack! He moaned and begged for forgiveness at his lack of attention. She preferred him attentive, especially when he could see nothing and could barely hear. Her hand trailed down his abdomen, bringing goosebumps, until she took hold of his cock. Suddenly, he felt the warm rain of her tongue through the steel confinement. He moaned and lifted his pelvis in gratitude. The tongue was withdrawn and the cage was removed. The freedom from the cage, allowed his cock to bloom and wag as though it relished being liberated. He felt hands on his head, removing the ear pieces, so that he could now hear.
"Today, I want you to listen and respond to me, since we will be doing some new activities. Please nod your head to show understanding."
He nodded, "Good." Something was placed around his fingers. "This is a buzzer that you will press, if you wish me to stop. Please test it out." He clasped his fingers to his palm and heard a beeping noise.
"I'm certain you noticed the packages in the closet. I have long had my eye on them and wanted to try them out on you. I'm very pleased that you have made it to this day." He felt himself blush under the hood.
"I will start out with one and add on until I have achieved my goal with you. If it is too much, we can stop anytime, but once we stop--." He shook his head vehemently, knowing what her unfinished sentence meant for him and his future. No more mistress. He heard her heels as she returned to his head and felt her kiss his lips. Tears sprang to his eyes as her tongued lightly prodded him to open his mouth, allowing her access. Feeling emboldened, he thrust his tongue forward, entangling it with hers and tasting her mouth. Her hand crept down to stroke his nipples and then his raging hard-on. He could have died happily at that very moment. She pulled her mouth away and withdrew. It left him feeling empty and a tiny bit petulant. The sound of movement and the opening of boxes ended his self-pity as he listened to her activity and wondered what she had purchased.
Returning to him, she smacked his cock, jerked it a few times and then smacked it again. The coolness of lubricant made him suck in his breath, before a slowly building pressure developed as his cock was impaled. He moaned as the steel rod sunk into his shaft. It felt huge, it felt as though it was impaling his entire body and straight into his brain. Twisting and pumping the rod, she fucked his little man-pussy. His hips started mimicking her actions and he moaned again. She stroked his cock as she pumped the rod, forcing him to bite his lips as a high pitched squeal threatened to escape him.
"I'm glad to see you enjoying that." She said with a smile in her voice. It frightened him. The lead shackle was removed from his balls and the cool air brought more goose-bumps as it played along his damp scrotum. The relief was short lived as he felt a scratchy pricking from the hemp rope that was being wound tightly around the base of his cock and balls, in a figure eight. She stood up and cranked on a pulley system that lifted and spread his legs at a right angle, exposing his asshole. He heard the snap of latex gloves.
"Life your ass up." A cold finger teased his anus with lube, circling and penetrating. He forced himself to relax, as he knew what was next.
"This one is a bit bigger than we've tried before, but I think you'll like it." There was not a trace of sarcasm in her voice, despite the fact that she knew it made his stomach knot up. His cock twitched, belying his mortification. The next moments were a frozen blur, followed by scalding eons as his ass was slowly stretched to take the butt plug. He felt like he was starting to choke on it and begged her not to continue.
"We can stop any time you like." It shut him up, but didn't stop the beads of sweat from popping out all over his body from the continued violation. A popping sensation brought a bit of relief as she stood up to view her handy work.
"Now we can get started."
The rope tied to his penis and balls was brought down over the top of the butt plug, up between his ass cheeks, and back around to the front of his thighs. His balls were dragged painfully downward as his cock jutted straight up into the air. Securing each side, she began to wrap it around his cock until only the head was showing. She then knotted the ends and tucked them away.
Grabbing his balls, she polished the sack with her palm before commencing to smack them vigorously. He howled and bucked at the pain, his cock bobbling to and fro.
"Quiet!" He settled on whimpering each time her palm connected with his balls. When they were cherry red from the smacking, she grabbed his cock and began beating the head. His hips began dancing in time with the beating, he bit his tongue to control the screams. Tears of pain sprang from his eyes and he gagged as his throat clenched and began coughing.
Suddenly the beating stopped and the top of the sound was pumped in and out of the swollen purple mushroom. He felt a movement as she reached around and tapped the butt plug. It began to vibrate deep in his ass, making him moan uncontrollably.
The feeling of the sound fucking his cock and the deep vibrations against his prostrate were incredible, as the pain from his tormented cock and balls slowly radiated and diffused through the rest of his body. Then it stopped.
"Are you thirsty?" He nodded his head and opened his mouth. He heard her move towards his head and felt her straddle his face.
"Do not spill any." She said as she let loose a stream into his waiting lips. He gulped greedily, the hot liquid alternately stinging and soothing his throat. Gratitude welled up in him.
"Thank you mistress."
"You are welcome."
She returned to the other end and moved the rope holding the plug, slowly she began withdrawing the massive thing and then pushing it back into him.
"Do you like your new toy?"
"Yes, mistress. I can barely stand it." She grinned at that and continued to fuck his ass with the toy, knowing that the vibrations were tantalizing his prostrate. Pre-cum dribbled from his cock and she dipped her finger into it and held her hand out.
"Lean up and open your mouth." He did so as best he could, and she pushed her finger forward so that he could clean it off.
She stood up and brought down a thin chain with hooks at the end, connecting it to the rope knot at the head of his cock. She pulled on it until it was dragging his cock up and into the air, followed by his pelvis as he attempted to ease the pain. She did not correct him, as she knew that eventually fatigue would force him to choose between a stretched cock and muscle failure. Grabbing a small leather flogger, she began to whip his cock, abdomen, and chest. At first, it didn't feel like much due to the rope acting as a protective barrier, but after a short time his sensitivity increased exponentially with each moment, and he felt every lick of the flogger, shrieking when it touched the head of his cock. She walked around, flogging the backs of his thighs and ass, while he moaned and pleaded for mercy.
