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She flipped through the papers pinned to the clipboard in her hand. It was more for something to do than anything else, she had already memorized everything there. Her first patient of the day was someone Dr. Olsen had been looking forward to meeting ever since the appointment was scheduled. She had met the man’s wife at the local BDSM club a few months ago. They had hit it off and had been slowly getting to know each other better ever since. They were still casual acquaintances, really. She had never been introduced to the husband.

Dr. Olsen stopped at one of the many doors spread throughout the hallway. The room number matched what was on the paperwork. She pulled it open and peered inside. It was a small waiting room with a scuffed floor and light blue wallpaper. There was a small desk to the left, a couch to the right, and a locked door in the far wall.

A naked man sat on the couch. He was relatively young, clearly no older than twenty, and gave off an effeminate impression with his soft jaw and a lower body completely clear of any hair. Legs, arms, chest, it was all smooth and blemish free. The man was also short, thin, had messy brown hair, and sat with his hands awkwardly shielding his crotch. His pale blue eyes jerked up at Olsen’s entrance, embarrassment plainly written across his face.

Dr. Olsen gave him a polite smile. “Brett?” She asked. He nodded, but his eyes were locked on the hallway behind her, through the cracked open door. In response, she subtly widened the gap, making his nudity more clear to anyone that may pass by. “I’m Dr. Olsen. I’ll be taking care of you today. You may call me Lily, or mistress if you feel like being polite.”

Brett licked his lips and shifted in his seat. She saw his member accidentally peek through his fingers for a moment. It was swollen in excitement. “Yes mistress,” he said.

Lily gave him a grin, warmer than her expression before, and then stepped into the room. She let the door silently swing shut behind her, easing his discomfort. “I see the nurses have already set you up for the appointment. Did you give them any trouble?”

Brett turned his eyes to the floor. “No, mistress,” he mumbled. “I followed orders.”

She chuckled. “I should hope so. They don’t appreciate any kind of rudeness. They get cross, to put it politely. I’ve seen them physically wrestle down a man twice your size and paddle his ass red, as punishment for an embarrassing attempt at flirting. They didn’t stop until he was blubbering.”

Brett didn’t seem to know what to say. Lily’s smile remained pleasantly inviting. He settled with, “I understand, mistress.”

Lily stared at Brett for a few more seconds, just long enough for Brett to begin feeling nervous, then let her eyes wander towards her clipboard full of paperwork. “Alright,” she said breezily. “I have your file right here. I understand that this is your first time visiting our clinic? It’s always nice to see someone develop a proactive interest in their health. New faces are always welcome. And you’ve requested such a thorough examination! Extremely thorough. Not many men feel as adventurous as you, unfortunately. I find that a shame. Don’t you agree?”

Brett nodded, a little hesitantly. “Yes, mistress.”

“Well,” Lily said, her eyes still on the papers, “I suppose I shouldn’t be congratulating you on your initiative too hard. According to my notes, you signed up for the appointment on the recommendation of your wife? Or rather, your wife signed you up herself.”

“Yes,” Brett admitted, falteringly. “I, um, spilled paint on the carpet. We had just gotten it replaced. Erin was very mad. She said that I needed to be… punished.” The last word was said with a generous amount of barely hidden dread. “Punished harder than she could herself, I mean.”

“I can understand that. This clinic employs some of the most professional caretakers that you’ll ever find.” Lily gave Brett a wink. “But I think you’re not giving your wife the credit she deserves. After scheduling the appointment, she remained in contact with the clinic through the entire session planning process, and we found her input to be extremely helpful. Informative as well. Thanks to her feedback, we felt confident enough to include some rather extreme procedures in your session, the sort of activities that we would usually reserve for patients that already have a few sessions under their belt. Everything you are going to be put through today has met Erin’s full approval. You have a very exciting appointment ahead.”

Brett licked his lips. His face was flushed, and his hands were cupping his crotch a little tighter than before. “I didn’t know that, mistress. About my wife, I mean.” He struggled with words for a few seconds. “Thank you?”

“You’re welcome.” Lily paused, then arched an eyebrow and gave his covered sex an unimpressed look. “There’s no need to be nervous. You don’t have anything I haven’t seen before. I am a professional, in case you’ve forgotten.”

After a short pause, Brett reluctantly moved his hands away. His fully engorged cock, now free to move, bobbed up into the air. His dick was, to Lily’s eyes, just a little above average in length and girth. It was pointing straight up towards the ceiling, with a glistening layer of precum coating his head.

Lily covered her mouth and giggled. “You certainly seem enthusiastic. I suppose that this is your body’s natural reaction to a situation like this. Are you looking forward to what’s coming?”

A light blush flashed across Brett’s face. He sunk a little deeper into the couch. “Yes mistress,” he murmured insincerely.

Lily shook her head in light exasperation. She didn’t bother to hide her smirk. “Well, if you find this so intolerable, let’s just move on to the appointment. Stand up, Brett.”

He did so with faint reluctance. His hands went towards his crotch, but then stopped. He forced them to his sides instead. Brett’s dick continued to stand at a jaunty angle. His body’s obvious excitement was a ridiculous sight, one made even more pronounced by Brett’s badly hidden embarrassment.

Lily’s gaze lingered on his cock, long enough for Brett to turn a little more red and look a little more humiliated. Then she turned away and strode towards the locked door. “Come with me.”

As she moved, Lily pulled a key from her pocket, then slid it into the lock. She popped open the door and walked through without pausing. She heard rather than saw Brett follow, then stop at the threshold behind her.

The walls were a shade of black that bordered on purple, the wood floor was a rich dark brown, and the dim fluorescent lights above draped shadows along the room’s edges. There was three huge bookshelves filled with vibrators, dildos, glass jars full of bundled rope and strips of tanned leather, clamps and clips, fat red candles, and much more. Riding crops, paddles, floggers and whips hung from the walls like hunting trophies. One corner held a busty female mannequin that was modeling a latex dominatrix outfit with a sizable strapon. The left side of the room held two cabinets, all locked shut, along with a sleek metal catering cart that carried a pump dispenser with ‘lubricant’ stenciled across the side. On the right side there was a grey tiled shower area, as well as a large steel sink, a coiled hose, an IV stand with a half dozen empty enema bags, and thick metal chains that hung down from the ceiling in front of the showerhead. In the center of the room, in front of Brett, there was something that appeared passingly similar to a massage table.

It was large, made of solid steel, and had thick red and black upholstery. Straps and buckles hung down from the sides like an untucked bedsheet. The nearest end of the table was split apart into two adjustable padded lengths, both set lower to the ground than the rest of the table. It was clearly where the legs were meant to go. The table had a semicircular headrest at the far end. There was a hole cut through the middle, surrounded by cushioning and restraints.

Lily chuckled, almost quiet enough to not be heard. “It’s impressive, isn’t it? Usually this room is only for premium members. Your appointment calls for some rather specialized tools, however. So this room was needed.”

“Um,” Brett said faintly.

“Don’t worry,” Lily chided. “Most of this has nothing to do with you. It will remain decoration. Most of it.” There was a jangle of shifting metal. Brett turned to see Lily take a head harness from a shelf. It was a mess of leather straps, small steel rings, and a ‘O’ shaped gag. She walked towards Brett, slow and unhurried, with a confident grin on her face. “This comes first.”

Brett licked his lips. “Alright.”

He let himself be pulled all the way into the room, and Lily closed the door behind him with a bump of her hip. Brett kept himself still while Lily loosened the leather straps and slid the harness onto his head. The straps were straightened and tightened, positioned so that that they were wrapped around his forehead, across his cheeks, underneath his jaw, and around the back of his head. Then Lily pressed the gag into his mouth. The ring of metal was large enough to force Brett’s mouth open, though not so wide that he felt uncomfortable. Lily tightened the straps even further, only stopping when the harness was snug against his skin, and then took a step back. She studied him for a short moment. “Yes. That will do.”

“What now?” Brett asked. The gag slightly slurred his voice.

Lily pursed her lips. “Now? We make sure you don’t speak unless given permission.”

Brett blinked, then looked down, ashamed. “Sorry, mistress.”

Lily shook her head. “Oh, I don’t mind myself. It was something your wife asked for. Her recommendations will have us deviating from a number of our usual procedures. She has also asked me to tell you what changes were made, once we get to them. This is the first.”

Lily went back to the shelf and grabbed a black rubber plug. It was perfectly shaped to slid into the ring gag, so much so that Brett’s mouth was soon trapped under an airtight seal. There was a tiny lock built into the plug, and with the twist of a small key Lily had the gag locked in place. The key was quickly threaded onto a small silver chain and hung from Lily’s neck.

Lily led a nervous Brett to the message table. She helped him crawl on top, guiding his body so that everything was properly lined up. Brett put his head facedown into the headrest, the hole a surprisingly snug fit for his face, and found himself staring at the floor below. The leg rests, relatively low to the ground and spread apart, had him kneeling with his upper body laid across the table and his feet dangling off the padded edge of the two padded lengths. Lily made sure he was in place, then took a step back and studied him. Brett was laying facedown across the massage table with his back to the air, his arms against his sides, and his ass held out.

Then it was time to strap Brett in. First came the thick leather belts, a firm foundation that ensured his limbs and torso were pinned to the cushioning. Then there were the straps, thinner and much more numerous than the belts, coming from all angles. These made it impossible for Brett to wiggle off in any direction. His legs, back, and arms were all covered in enough layers to keep him utterly immobile. Only his ass was left free and accessible.

The last thing to be tied down was his head. The straps around the headrest were set low, which meant the spiderweb of restraints all pressed against the back of his head. His face was stuck inside the circle of cushioning, just as trapped as the rest of his body. Brett experimentally fidgeted, but it did nothing more than flex his muscles. He couldn’t move at all.

Lily rubbed the back of Brett’s head, running her fingers through the patches of hair that the straps weren’t covering. She hummed a short tuneless noise that practically oozed satisfaction. “There, isn’t this wonderful? Now you’re completely trapped. You can’t get out even if you actually try.” She planted a kiss on the back of his head. “Now we can really get started.”

Lily turned away. Her short heels clicked against the wood floor as she walked over to the catering cart and gently pushed it to the bookshelves. Lily knew that Brett could hear her, and that he would have no idea what she was doing. All he had to work with was soft rustling and the clank of metal against metal, as Lily loaded the catering cart full of sex toys, equipment, and other similar things. All of it had been set aside for the appointment, left in plain view. Then there was squeaking wheels and the scratch of a key against metal as Lily unlocked one of the cabinets. She pulled out everything she planned to use that she had not wanted Brett to see, even hidden among everything else. Once she was finished, her steps ambled over to Brett’s immobile body. The cart was put near his side.

Lily snapped on a disposable latex glove with an unnecessarily loud flourish. Lube from the pump dispenser spurted out with a series of squeaks and squirts that were very noticeable in the otherwise dead silent room. At this point, Brett must have had an inkling as to what Lily intended to do. That was why she didn’t find it surprising when her finger, slick and cold, slipped into his ass without any trouble. Brett was ready and actively relaxing his asshole.

She played around in his ass for a few seconds, sliding herself in to the bottom knuckle and then back out again, before she pulled back and pushed in two fingers. It was not difficult at all. She only spent a few moments wiggling inside his channel before she went for three, and this time there was a small amount of pushback. Lily had to power her way through his resistance with a fair amount of force. His ass had soon swallowed all three fingers, though. Lily reached towards his prostrate and gave it a few short rubs, making Brett fidget, before she pulled out.

Lily was fairly sure that Brett expected her to go for four fingers, or maybe pull out some sort of toy. The tip of the speculum against his anal ring must have come as a complete surprise. She was able to push the dull metal blades into his ass with little trouble, deep enough to fully bury the speculum into his ass and press the metal rim against his asshole. The blades, a pair of curved steel bars, were only a few inches long and not very wide at all. Brett probably did not see the danger until Lily began to lightly squeeze the handle. The harder she squeezed, the farther the blades spread apart and the farther Brett’s rosebud was forced to open. Brett began to grunt and groan once Lily sped past a width of four fingers, but his struggles did nothing against the speculum’s merciless pressure. She couldn’t tell if the noises he made were from pain or pleasure, but it didn’t matter either way. Lily didn’t plan on stopping, or even slowing down.

Brett’s ass was gaping by the time the speculum was finally set to what she wanted. It was wide enough that she could easily slide her whole hand inside, and maybe even a fist if she was willing to force it. About half his anal ring and part of his inner wall was hidden underneath the speculum. Everything else was left open to her view.

Lily leaned closer. She could see a fair distance into his inner channel, and she was happy to find that the nurses had done an exemplary job administering their cleansing enema. There was no hint of filth anywhere. “There we go,” Lily said, praise clear in her voice. “You’re nice and spread open now. You’re doing very well.”

Lily stepped back and tore off the latex glove, throwing it into the trash. She reached over to the cart and pulled out a violet wand, a simple plastic handle connected to a glass tube shaped like a very long pencil. She turned the wand on and was rewarded with a purple glow and an electric hum.

Brett tensed. Lily simply flicked the wand off, slid it deep into his ass, then pressed the tip down, letting it lightly rest against the inside of his channel. She turned the wand back on.

Brett’s reaction was immediate. His body twitched and jerked in an unconscious attempt at escape, and his heavily muffled shouts of pain were made indiscriminate behind the thick plug forced into his mouth. Lily heard the sharp electrical crackles, saw how the electricity bite and snapped as the steady stream of low voltage current was unloaded into Brett’s bowels. Lily slowly moved the tip of the wand around in a circle, never letting the end lose contact with his body, tilting the glass tube as she went so it brushed up against the walls close to his sensitive anal ring. She could see his innards twitch and dance, thanks to the speculum. Lily always enjoyed the surprisingly energetic reactions that she could draw out from some simple shocks.

Lily turned off the wand. “Well? How would you rate the pain, from a one to a ten?”

The gag turned Brett’s words incomprehensible. Lily hummed knowingly. “Ah, yes. I completely understand.” She paused, then dragged the wand to an untouched part of his ass and turned it back on. Brett cried out and spasmed as the electricity mercilessly attacked him. Lily flicked the wand around, lightly tapping different sections with quick bumps. If she held the wand right above his flesh, with just the smallest amount of space between him and the glass, she could get electrical arcs to spark between the two. It was all very interesting, and judging by Brett’s reaction it was also quite painful. She played around for a little while longer, then let the wand die. “Again, please rate the pain from a one to ten.”

Brett made a serious attempt to say something Lily could understand. She could tell he was really trying. It was still garbled gibberish. Lily chuckled. “Ah, thank you. This is a very important part of the test, so I will do my best to ensure the most accurate results. I will continue applying shocks until I feel satisfied with the level of feedback reached. Don’t be afraid to tell me how you feel!”

For a good fifteen minutes, Lily amused herself by torturing Brett, zapping him at unexpected angles with bubbly enthusiasm. Sometimes she paused and let him lay there, tense with sick anticipation at what was coming, before flicking the current on and bringing fresh pain. She played him like an instrument and drew out his cries of pain with the professional skill of a virtuoso. Every so often, Lily would tease Brett with another line of questions. “Can you tell me how much this hurts? How about this?”

Eventually, Lily grew bored. It was fun to watch him squirm, but she couldn’t do this forever. There was still the rest of the session to go. She gave him one last parting shot, a lovingly slow zap applied to his prostrate, before she put the violet wand away. Lily rubbed Brett’s ass with slow, smooth strokes, kneading him like a masseuse. “There we go. We’re finished with that. You did a good job.”

She heard Brett breath through his nose in relief. She could feel the muscles underneath her hands slightly soften, easing as some of the tension left his body. Lily gave his ass one last parting rub before she snapped on another latex glove, then pulled out and screwed opened a small glass jar. She dipped her glove covered hand inside and scooped out a glob of green paste.

“This is one of our clinic’s special attractions. It’s an herbal remedy, made to strengthen the bowels and provide long term health benefits to the muscles within your rectal area.” She smeared a thin layer of the creamy substance across the stretch of outer anal rim not hidden underneath the speculum. Then she dabbed a slightly thicker coat on his anal ring inside his channel, paying close attention to the sensitive nerves.

Brett’s asshole suddenly clenched. The muscles fruitlessly clamped down on the speculum with what was probably as much force as he could muster. “Now, you might feel a little burn,” Lily belatedly added. “The recipe for our herbal paste calls for a long list of natural ingredients, like large amounts of finely diced ginger and tabasco sauce. It should be fine! A little heat never hurt anyone, you know.”

Lily paused. “Of course, the burning will grow stronger as time goes on, especially since I’m using a much more intense version of the paste. You can thank Erin for that. She told me to remind you that cleaning up the paint you spilled was, and I quote, ‘a huge pain in the ass.’ I hope you appreciate the irony.”

Brett was thrashing against the straps covering his body. His tossing and turning was not accomplishing anything. Lily smiled. The paste was definitely starting to take effect. “Don’t worry,” she said soothingly. “I’m sure it hurts, but that’s just how it is. There’s nothing you can do about it. Just bear with it as best you can, alright? I still have a whole jar of paste to go through.”

Muffled shouts met her words. Lily ignored him. She took another palmful of paste and went to work coating his inner channel. With slow, even strokes, Lily smeared the thick paste across the walls within his ass, making sure to cover it all evenly. She went back for another scoop, continued on, and then went for another. Her hand was eventually wrist deep in his ass, digging away at the far depths with fingers tipped with dollops of paste. Everything inside his ass, as deep as she could reach, was smothered underneath the green paste. Brett’s reaction to the burn had long since gone past panicked thrashing and was now firmly locked on mindless bucking and yowling. His bondage was so thorough that even this did not get him to budge.

Lily tore off the latex glove and threw it away. For a while, she just stood there and listened, letting Brett exhaust himself. He slowly began to settle down, his protests softening into relatively quiet whimpers and guttural groans. The change was more from fatigue than any decrease in pain. Lily spent another minute or two just watching Brett, eyes locked on his twitching innards and his exposed ass. Eventually, she spoke. “I’m not entirely heartless, you know. I know how much that must hurt. Do you want me to give you something to ease the pain?”

She couldn’t help but laugh at the tearful begging that immediately followed. She didn’t understand a word, but his tone of voice was clear enough. Humming a jaunty tune, Lily leaned down and reached towards the lowest shelf on the catering cart. A huge stainless steel pot took up a good chunk of shelf space. She popped open the lid, letting a wave of chilled air pour out from the opening. The pot was filled to the brim with gallons of ice cubes. She dug a hand into the ice and carefully pulled out what she was looking for.

It was a remarkably long strand of anal beads. Each bead was tiny, almost inconsequential but was also covered in an intimidatingly thick shell of ice. It was enough to make each bead a lot larger than anything Lily would ever want up her own ass. She held it from the top string, letting it hang down and sway in the air. The ice was too cold to touch comfortably without gloves.

“Here you go!” Lily chirped. She fed the first bead into Brett’s spread open asshole. His quivering inner channel became a little more lively once the painfully cold ice touched him. His sudden moan of pain was not enough to slow Lily down, nor was the increasingly loud noises he made as she kept pushing more and more through. A steady stream of ice coated anal beads were pushed into his ass, where they could slide and brush against the paste. That had Brett calm down a notch. But only a little. His body was still clenched in pain.

Lily kept forcing more and more beads into his body, shoving them in as deep as she could. It was farther inside than what he must have been expecting, judging by his reaction. The sound he made as the final piece of ice passed his anal ring was enough to have Lily snicker. She made sure her amusement was loud enough for him to hear. His reaction to her sadistic delight was half the fun.

All throughout his ass, including the depths where her fingers could not reach, he had to suffer under the touch of the agonizingly cold ice. In many ways it was just as bad as the burning. From Lily’s experience with prior patients, she knew that the worst part of it all was that the ice would not entirely banish the fiery inflammation; the burning would return if the ice no longer pressed against the paste, and the anal beads were purposely shaped to leave gaps between each ball. They would never touch everything at once. He had to endure the heat and the cold in equal measure. To top it all off, the beads would eventually melt down to nothing, leaving him to deal with the tail end of the burn. It really was a no-win situation.

“You did wonderful,” Lily told Brett. She ran a hand across his back, as if she was soothing an animal, then loosened the speculum. It only took a few seconds before the whole thing was out. Now the anal beads were kept in place by his asshole. He was desperately clenching down as hard as he could, so Lily did not think they were going to slip out any time soon. “We’re just going to move on, alright? There’s some other fun stuff I want to show you. Please try to relax while I adjust the table.”

Lily went to the complicated mess of metal that made up the massage table’s control system. She forced various bars and levers into different positions with copious amounts of tugging and pushing. Once she was finished, Lily took a firm grip on the table.

Brett’s eyes widened as his body suddenly flipped. The table rotated so that his back faced the floor and his squinting eyes suddenly pointed towards the fluorescent lighting. His legs, still bent as if he was kneeling, were now up in the air, spread apart in a way that vaguely brought gynecologist stirrups to mind. The leather belts and tight straps were more than thorough enough to keep him from sagging downward with the sudden change in gravity. His body remained pressed against the cushions.

Lily kicked a lever and locked the table in place. She met Brett’s eyes with a smile that widened at his anguished expression. “Good, I see you’ve been enjoying the appointment so far. Well, don’t worry, there’s much more to come.”

Lily turned away and rustled through the cart. She returned with a thin white cloth and a handful of plastic pegs. Lily laid the cloth over Brett’s face, made sure his nostrils were covered, and then pulled the cloth down against his skin. There were small holes scattered across the ring of flat metal that surrounded Brett’s face. She held the edge of the cloth over the nearest hole, lined up a peg, then pressed down and filled the hole, pinning the cloth in place. She repeated this over a dozen times, until the cloth was tightly drawn over Brett’s eyes, nose, and forehead. It was pressing down on his face so hard that his expression underneath was clearly visible. A bubble of cloth below his nostrils expanded and compressed with each inhale and exhale. The material was too thin to hamper his breathing.

Lily picked up a spray bottle. “I’ll admit, I’m usually not very interested in breath play. In this case, I choose to defer to Erin, who seemed to have her own very firm opinion. With that in mind, I should mention that your wife was kind enough to drop by yesterday and provide a urine sample.” She shook the spray bottle, letting him hear the liquid inside splash.

Then she squeezed the trigger, and the spray bottle shot out a thickly condensed puff of mist. One spray had Brett flinch in surprise. A second was enough to visibly moisten the cloth and turn the bright white coloring a little darker. Lily kept it up, letting out more and more bursts of piss, wetting the cloth further and further, until the small bottle was empty and there was no more to squeeze out. The cloth covering Brett’s face was soaked, almost dripping with piss, especially the small hollow that rose and fall with his every breath. Brett now had to fight to pierce the urine drenched rag.

Lily smiled, then set down the spray bottle and strolled over to the other end of the table. It was telling that, even after all the abuse, his dick had not gone soft. It was standing at half mast, pointing to the ceiling at an sideways angle. His hairless crotch, flabby ballsack, and precum-stained dick were all open to the air, and her touch. Lily gathered all the materials that she needed for the next step and set them within easy reach.

First, she ran a hand down his shaft. His dick shivered at her touch, straightening out even as she lightly petted his shaft with the tips of her fingers. His erection stood straight up once she started to rub the head of his dick with the palm of her hand. Precum practically gushed out at her touch, coating her bare palm with his sticky seed. Lily grinned.

“This is supposed to be a punishment,” she murmured. “But can that be true when you’re so excited? It’s obvious that you’re really enjoying all this. Why else would your dick be hard, even after I put you through so much pain?”

She continued to tease the man, slowly pumping his shaft with two fingers that only just touched his skin, pressing down with the barest amount of force possible. Brett’s cock twitched at her touch, trying and failing to thrust upward with each pass. His bondage was too much for that. He could only lay there, still and almost silent, as Lily went to work on his dick, relentlessly building him higher and higher with her light stroking. When Brett’s groans and growls reached a fever peak, Lily moved her hand away. His cock was red and straining, just on the edge. She laughed at his frustration, then blew a hot breath onto his tip, enjoying the way his body shuddered and his cock spilled another small dollop of seed. The precum that dripped off his head signaled the orgasm that was ready to burst out at the smallest touch.

“Now, now. You haven’t been good enough to earn something like that. I just said this is supposed to be a punishment. You’re not here to have fun, you know. You’re here to suffer.”

Lily ran her hands through the cart, picking up and moving various items with enough force to audibly signal that she was no longer paying attention to Brett. She watched him try and fail to squirm around, desperate to finish himself off. His dick remained untouched, trapping him on the edge. Lily snuck on a latex glove, quietly enough that Brett could not hear her, then picked up an ice cube and held it against his balls.

Brett’s reaction what just what Lily had expected. His body shivered and tensed while his voice was kept smothered by the gag and the piss-soaked rag. The painfully cold ice forced his dick to deflate, his erection disappearing with almost visible reluctance. She kept the ice against his jewels for another ten seconds, just to make sure.

Then she picked up the chastity belt. It was a small thing, with a plastic collar at the base and a metal mesh sheath for the cock. The sheath itself was tiny, looking almost like an afterthought compared to the rest of the chastity belt. Lily fitted Brett’s dick into the sheath’s entrance, pulled his balls through the collar at the base, and then pushed the belt all the way on. It was a snug fit, even with his cock completely deflated. Brett moan and shifted, unhappy with what was happening but unable to stop it.

It only took a few moments to tighten the chastity belt. It clamped down at the root, latching on like a cock ring, while the loop his balls had been pulled through was also adjusted, made to clench down on the base of his sack like a pair of jaws. Not enough to hurt, but enough to trap him. The last step had a small padlock click shut near the base of the belt, locking everything in place, and the key was quickly threaded through the chain that hung from her neck.

Lily took a second to admire her work. Then she leaned over and swallowed Brett’s cock. The fine mesh did nothing to block his dick from the warm, wet touch of her mouth. She could feel Brett’s body tense below her, and she almost fancied herself catching the shiver in his cock as it tried and failed to expand. Lily smiled, then swirled her tongue over the tip of Brett’s dick, teasing the sensitive spot with expert skill.

She let go of Brett and took a step back. His dick was bulging out against the mesh, like a hand pushing against a chain link fence. The obvious desperation, combined with the comically small size of his member, had her laugh. “I hope you weren’t expecting anything too exciting to happen. What kind of punishment would this be if I were to just give you a blowjob? That’s just unprofessional.”

Lily gave Brett’s leg a grandmotherly pat. “Don’t think I don’t understand. It’s all very exciting, right? If I had kept touching you for just a second longer, you might have popped right there. Luckily I have something that will keep you from embarrassing yourself.”

The urethral plug was unassuming. Short, not too long, but also quite wide. She was able to push it in without much trouble. Brett certainly wasn’t expecting it, judging by his muffled shoat at the sudden penetration, but he wasn’t even capable of shifting his weight. His body offered no resistance. Lily locked the plug in place by tightening a tiny clamp built into the chastity belt.

“There you go! You won’t have to worry about any accidental ejaculations today. I’ve taken care of it for you. You can thank me later, if you want.”

Lily started to rub Brett’s sack, paying close attention to his balls. She shamelessly pleasured him with her fingers, doing her best to bring him closer to the edge just through his jewels. “One thing I should mention? These plugs don’t outright stop orgasms, they just block your ejaculations. The semen doesn’t go anywhere. Do you know what a dry orgasm is? I’m assuming you do. Erin seems like the kind of woman who would be interested in that sort of thing. Interested in giving her boyfriend a dry orgasm, I should say.” Lily chuckled, then stopped massaging Brett’s balls. “If you don’t know what I’m talking about, then let me just say you’re looking at some short lived pain, a pair of aching balls, and no satisfaction.”

Brett’s breath was beginning to grow heavier. Lily supposed that the paste in his ass was finally starting to reach full strength. She could see that the pleasure from her touch was already fading away. “It looks like your mind is starting to head towards other things. Like your ass. Don’t let me stop you! I want to give you time to really focus on that pain. It’s a very special kind of feeling.”

She walked away from the massage table with a sharp clicking of heels against wood. She spent a few minutes looking over her equipment, preparing for the next step, though mostly she was letting Brett stew. Brett’s body was shaking and twitching from the sensation of fire and ice in his ass, and it was only growing more agonizingly extreme with each passing second. He couldn’t do anything about it. He was completely helpless.

After a while, Lily wandered back over. Her next words were spoken with a teasing lilt. “This is another addition to what would otherwise be a softer session, courtesy of your wife. She also has a few messages she wants to pass along. The first is, ‘Three across the ass for making a mess.’”

The rattan cane slammed against Brett’s ass. His scream was muffled underneath the gag, but not enough to hide the strength of his reaction. It didn’t surprise Lily. The cane was an intense tool of corporal punishments, easily capably of scarring flesh if used by the stupid or inexperienced. Lily was a professional, though. She had perfected her technique. She knew just how much strength she could safely put behind a blow.

Lily gave Brett seven seconds before winding back up and delivering a second strike, pounding the cane against both asscheeks. That squeezed a fresh howl of pain from his tortured body. Lily wasn’t holding back; she was caning him as hard as she could get away with. With her skills, she could easily keep herself from hitting him too hard and going over his limit. Or his body’s limit, to be more precise.

Again, Brett was given seven seconds to recover before she struck him for the third time. The cane smashed into his ass with enough force to leave Brett impotently thrashing in agony. The sharply muffled noises he was making could only be described as caterwauling. Another seven seconds passed, and once nothing happened Brett began to quiet down. Lily took a second to admire his heavy breathing and watch his tense muscles fight against the straps crossed over his body. Then Lily let out an amused sigh. “The second message, then. ‘Another three across the ass for making me clean up your mess.’”

Again came the cane. Again Brett howled. His ass was getting red now, like a tomato, with three bright lines set parallel to one another. Because she was eventually going to run out of untouched space to hit with the cane, but mostly because she wanted to, Lily let the next two swings land on already reddened flesh. The screams that brought out were half an octave higher. It wasn’t obvious the first time, but the second strike made it more apparent.

Lily lightly tapped his ass with the cane. She laughed at the sudden flinch. “Alright. The third message. ‘Three more for having to take time out of my life and schedule your appointment.’”

Brett knew what was coming. It didn’t help him gracefully weather the next half a minute. Lily hit him just as hard as before, but with his freshly tenderized ass it was a question whether he even realized that. Her blows must have felt like bolts of lightning. Each flick of her wrist had Brett writhing like a man possessed, his pain apparent through wet breaths that bordered on outright weeping. The damp cloth threatened to choke him if he blubbered too hard, though, so he kept relatively quiet.

Most of his ass was red, some strips darker than the rest, and it was all getting worse as the seconds passed and his body belatedly reacted to the damage. Lily knew that Brett wouldn’t be able to sit down without wincing for a week.

“There we go,” Lily cooed. She set the cane to the side and began to rub his ass, slow and tender. His muscled remained tense under her touch. “You did a good job. Your wife would be proud to see you now.” She paused for a second. “Well, maybe not proud. Satisfied. She wanted you punished, and it looks like you’re hurting pretty bad.”

Brett groaned in agony. Lily ignored him. She continued to rub down his ass, focusing on the most heavily tenderized flesh. “It takes some bravery to make it this far, you know. Most men would have crumpled by now. Erin has done a wonderful job training you. I’d even go as far to say that you’re one of the best little boy toys I’ve had strapped to this table in a long while. It’s been some time since I’ve gone all out.”

Lily hooked a finger through the end of the anal beads and pulled. The first bead slipped past his asshole like it wasn’t even there. Brett grunted in surprise, but Lily just kept pulling, taking another two beads out before he could really react. The beads were halfway melted down to the nub. There was still some ice, but not nearly as much as before.

Lily clicked her tongue. “I thought it was about time, but I guess I was wrong. There’s a fair amount of ice left. It seems to have warmed up a bit, though. I bet it doesn’t hurt as much now as it did when I first put it in. And just in time, too! The burn must be at its worst right about now.” Lily sighed in mock regret. “It’s a shame that I have to take it all out now.”

Brett all but shouted in surprise and anger. Lily smiled. “Sorry buddy, but I need that ass for something else. So it’s coming out. Besides, it’s not like you really get to decide what I can or can’t do. I don’t really care if you think you need it.”

The rest of the anal beads slipped out like they were greased. Brett clenched down as hard as he could, but that did not stop her at all. Lily tossed the string to the side, then ran a thumb over the top of Brett’s asshole. His body shuddered at the loss of the ice. Lily flicked his starfish, grinned at the sudden spasm, then stepped away and turned back to the cart. She pulled out a harness with an attached strapon and began to put it on, quietly so that Brett did not know what was coming.

Brett groaned, loudly and insistently. “I don’t know what you want me to do,” Lily said with practiced indifference. “I know it hurts. Deal with it. Isn’t self-reliance something that’s supposed to be manly? Well, be a bigger man. It’s not like I’m going to give you any more ice. There’s just no reason for it, you know? Something nice like that isn’t something you get to ask for. You get it for good behavior.”

Brett gurgled out some unintelligible noise. It was obviously not anything close to a compliment. For his sake, Lily chose to ignore it. “If you really want something to take your mind off the burn, I have a very special surprise right here. It’s not nearly as nice as the ice, but you’ll take what you can get, right?”

Lily slathered the strapon with lube, gave it a good rub, and then pressed the tip against Brett’s asshole. It spasmed at her touch, and Brett started to struggle with renewed desperation once he realized what was happening. “Yup! That’s right. You’re getting this thick cock, straight up the ass. It’s a nasty one too, make no mistake. Erin wouldn’t accept anything less than the meatiest strapon. To be frank, I think you’d be scared if you could see what I’m about to fuck you with. It’s very intimidating.”

Her words were a little exaggerated for effect, but there weren’t lies. The strapon was much larger than what she would usually use. Something this size would normally be for fucking a woman’s sex, or an ass that had just been stretched open. She wasn’t worried, though. Erin had explained how often she used her own strapon, usually as a punishment for misdemeanors. He was used to painfully taking it in the ass, even if this was bigger than anything Erin had ever used.

She pressed the strapon down, just a little. The tip dug into his channel, just barely breaching his anal ring. Brett’s futile attempts at escape intensified. Lily hummed, her voice airy in anticipation, and then began to push harder.

“Like I was saying a while back, I’m very proud of you,” Lily said. “You’ve been doing a wonderful job. I just need you to keep it up just a little longer. Okay? It would be very impressive if you could take this gracefully.”

Lily pushed harder. Brett groaned as his ass was forced to swallow more rubber. He still hadn’t taken the whole tip, though. “This is happening because of your wife, by the way. She wouldn’t let me accept this session if I didn’t get my own orgasm. Couldn’t imagine why I would bother with punishing you if I didn’t take some pleasure of my own. So I’m going to fuck you in the ass until I come. It’s not going to be easy, since this strapon isn’t doubled headed or anything like that. There’s no vibrators, either. I’ll have to grind the base against my clit.”

Suddenly, without warning, Lily thrusted forward. About an inch and a half of rubber cock was forced into Brett. His reaction was very satisfying. Lily was always happy to see that she was having an effect on her clients. “What I’m trying to say is that this is going to be a long, thorough fucking. I’m not here for you. This is for me. You’re just the human fleshlight I happen to be rubbing myself off with. I’m not going to bother slowing down or stopping if I hear any whining.”

Lily felt a sadistic thrill run through her as another inch went forward. He could feel how thick her strapon was, and was reacting with the appropriate panic, but he still had no idea how long it was. Since she liked to think of herself as a considerate woman, Lily decided to spare him the drama and go down to the hilt as fast as she could. She increased the pressure, and Brett took another inch.

“Right now, it’s your job to lay back and get fucked. Literally the easiest job in the world, you can’t mess it up. This is happening no matter what. You can’t stop this. Just try to relax as best you can. Alright?”

She pushed another inch in. Than another. Lily pushed. Slowly, inexorably, more and more of the strapon penetrated Brett. He seemed to have abandoned his earlier thrashing and was stock still, probably trying to take the dildo as gracefully as he could. His resolve was visibly diminishing as more and more of the strapon was shoved up his ass, with no end in sight.

Finally, eventually, it was finished. Lily was all the way in. Brett had taken everything. That was impressive, because Lily’s strapon was quite long. She was proud of what she had done. Brett seemed to have fallen back on his older plan, the one where he desperately but ineffectually fought against the straps holding him in place.

Lily bit her lip in anticipation. “Alright then,” she muttered. And then she began to fuck him.

It was, as she said, slow and thorough. She unhurriedly pulled out, leaving just the tip still inside, before she pushed forward and buried herself in his ass. She couldn’t say she was being gentle, but neither could she say that she was purposefully trying to hurt him. She was testing herself, finding the pace that felt the most enjoyable.

It was definitely worth experimenting with. Brett seemed to alternate between fighting against the intruder as much as he could and attempting to passively accept the fucking. The former tactic gave a wonderful sense of resistance to her thrusting, and with the right angle she could outright push the strapon against her clit. He didn’t keep that up for long, though. Lily imagined that his inner walls, already horribly irritated by the paste, were screaming bloody murder at the rough treatment. Staying still went against every instinct, but it probably was the best chance he had at getting through this ordeal with the minimum amount of torture.

But that didn’t feel as good as when he actively struggled. So Lily sped up her thrusts. Then, while he was caught off guard, she slapped his ass as hard as she could. Lily could feel his reaction through her strapon. That, along with his sudden shout of pain, had her snickering. When next Lily pulled out, she slapped both cheeks while she pushed, timing herself so she speared him just as she hit him across his ass. Lily liked the way that felt. So she did it again, and then again.

That set the pace for the next ten minutes. Lily slapped his ass with every thrust, or sometimes once every few thrusts, holding herself back so the next strike could surprise him. The fucking wasn’t too intense, because Lily like the relatively slow pace. That felt the best. She was entirely focused on how the base of the strapon rubbed against her body. Everything she did, from her angle of attack to the speed of her fucking, was done to best increase that delicious friction. She certainly didn’t bother listening to anything Brett said, though his cries of pain certainly got louder as time went on. Lily was relentless. She fucked him like she was ready to fuck him for the rest of the day.

“I really like the way your body twitches when I do that,” Lily said after a particularly nasty two-handed slap. After he was done howling, of course. “Maybe I should stop and grab a hairbrush. I have one over there. How do you like that idea? I can give you a much nastier spanking with that than with my hands. That could feel really good.”

Brett desperately babbled. Lily tuned him out. “Maybe not. I don’t want to stop fucking you. I’m really getting into the groove.” Lily expertly plunged in with a tiny twirl of her hips, making it so the round tip of the strapon scraped against the edges of his inner channel. Brett’s pathetic attempt at begging fell apart. “Yeah. You still feel the burn, huh? That’s a rough deal. Too bad, I guess.”

Brett didn’t respond. His breath was heavier. More wet as well. Lily continued to fuck him, hard enough to really put pressure against her sex. She was soaking wet now. The fucking was starting to feel amazing, enough to leave her panting. It took a few moments to realize that Brett was panting as well. It took another moment or two to realize what that meant.

“Hah! It looks like I’m not the only one having fun. You’re close to coming, aren’t you? You’re getting off on this. God, what a pain slut! I mean, here I was going on about how this was just for me and that you’re just a means to an end. You’re making me feel silly, to be honest.”

Lily slapped him again. She grinned at his shout of pain, and at the telling way his insides quivered. She had fucked enough men to know when they were close to an orgasm. “What does that say about you, though? Even after all this, you’re still feeling randy? Can you really complain if you’re enjoying this enough to come? Oh, you’re close! I can feel it.”

Lily thought about slowing down, but decided against it. “Ah, I’ll let you have this. Cheers!” And then she sped up, fucking his ass with twice the fury as before.

She could feel the moment that Brett’s orgasm hit him. His asshole somehow managed to clamp down even harder, almost enough to put up a fight and slow down the fucking. His feet curled into themselves, his butt cheeks twitched and jiggled like crazy. His whole body seemed to be spasming from the sheer power of his orgasm. The overwhelming sensation of pleasure and pain must have been devastating. Lily laughed.

“Not the same with that cock plug, huh? There’s no mess!” Lily continued to plow into Brett’s ass, not slowing down at all. She didn’t care how he felt about that. She was starting to get close to her own peak. “I bet you understand what I was talking about now. ‘Some short lived pain, a pair of aching balls, and no satisfaction.’ That’s what I said. Well, your balls have to be feeling pretty tender right about now, and I’m sure you’re already hurting plenty.”

Lily blinked. “Oh, wow. I can’t believe I hadn’t thought of that.” She slowed her next thrust so that she could lean over and slap his balls with the back of her hand. Brett shouted and thrashed. “Nice! That’s a much better response than what I got from the spanking. It feels good. Let’s do it again.”

Her other hand slapped him right on time with the thwap of her waist against his ass. It was wonderful. Lily’s core was getting deliciously hot. She was close. Brett was crying out in agony, desperately trying to handle the punishing blows raining down on his sensitive jewels. Lily kept going. She was getting near the edge.

“Fuck, fuck,” Lily groaned. She bit her lip and shuddered, even as she plowed into him faster. Her jackhammer pace mercilessly pounded his ass. She stopped slapping his balls so that she could dig her nails into his asscheeks. “God yes, fuck, I’m coming!”

Lily’s orgasm hit her like a truck. There was no other way to describe how it utterly blindsided her. Her whole body was drowning in it, burning hot and wet and amazingly good. Her breath was coming out fast and aggressive, like a boxer throwing punches. For a second, her mind just blanked, temporarily senseless from the overwhelming intensity of it all. She continued to thrust through the whole thing, almost animalistic in her need to keep rubbing her clit. She didn’t know how much time passed before she began to gradually wind down to a stop.

A small amount of time passed. Lily just stood there, breathing heavy, now covered in a thin sheen of sweat. She pulled herself out of Brett with a satisfied groan. Brett moaned back. Lily barely noticed. She was riding the wave, and it felt wonderful.

She gave an appreciate glance toward his twitching asshole. His starfish was still biting down on the air, as if his body wasn’t aware that the fucking was finished. Brett was still, exhausted and sore, quietly suffering from the brutality of it all.

“I really fucked you senseless, huh?” Lily giggled, then unsteadily unstrapped the harness from her body. The sex toys and other pieces of equipment lying around were put back in the cart. She also pulled the piss-soaked rag off Brett’s face. His bleary, unfocused eyes fluttered open while Lily pushed the cart back to the other side of the room. She checked herself out in a small mirror, then straightened her clothes and combed back her hair. She also dabbed the sweat away. Her face was still flushed, but other than that she looked like the model of cool professionalism. Lily picked up her clipboard, along with a small pile of clothing, and walked to Brett’s face.

“Well! I’d call that a successful appointment.” She aimlessly flipped through the clipboard for a few seconds. “Yes, we went through everything that had been scheduled. Wonderful! These things sometimes drag on for too long, you know. I’m glad we were able to finish this on time.”

She patted the top of his forehead, like he was a dog. “The nurses will be here soon to release you and help get you ready to go. That being said, Erin had one final message that she wanted to pass on.”

Lily lifted her hand so that Brett could see the clothes. His tearful eyes blinked and slowly focused on the pair of lacy silk panties, white booty shorts, the thin pink t-shirt with "JUICY" written across the back, and the pair of red stripper heels.

“I have it written down right here. ’You act like a bitch, you walk home like a bitch. Don’t bother asking about your old clothes.’ I should also mention you’re not getting your car keys back. Erin will come by later and pick the car up herself.”

Brett’s stared at the clothes with wild-eyed intensity. Lily shrugged. “It’s only a ten, fifteen block walk. That’s a good workout. Plenty of time to show off your fun little outfit, too. And don’t even think about taking a bus or something like that. Erin will find out, and you’ll earn yourself a one-way trip back to my table.”

The look of shame on Brett’s face was enough to make Lily grin. She leaned forward, conspiratorially. “If it helps, most people would never guess that you’re a man. You have a body and a face feminine enough to pass for a girl. A very slutty girl who dresses like a whore, of course. Knowing Erin, I’m sure this isn’t the first time she’s had you wear something like this. Crossdressing is embarrassing enough to be a punishment in itself, right?”

“Of course, I’m sure you’ve never been forced to do anything nearly as humiliating as this,” Lily added, almost absentmindedly. “Those are a lot of blocks. A lot of people. Still, the only alternative is walking out naked. I assume you’d rather crossdress, no matter how emasculating that is. It’s still your choice. I’m not forcing you to do anything.”

Lily set the pile of clothes on top of his chest, then shot Brett a bright sunny smile. “It was wonderful meeting you, Brett! I enjoyed our time together. I hope to see you again sometime soon.”

Brett’s response was completely hidden behind his gag. Lily soaked in his anguished expression, then blew him a coquettish kiss and left the room. She walked through the outer waiting room and into the hallway, then pulled the key chain from her neck and hung it on the door handle. That would signal any passing nurse that the patient inside was ready to be let free and be taken care of. They had a copy of her schedule anyways, so they knew when they were supposed to come. Brett would be let out in five, maybe ten minutes.

Dr. Olsen strolled down the hallway, humming while she went. The first patient of the day was a rousing success! Everything had gone well. It would be wonderful to talk with Erin after Brett had trudged home. She was sure that Erin would feel satisfied with appointment’s outcome, and hopefully convince her to send Brett over when he inevitably earned himself another punishment.

Now it was time to drop off the paperwork and move on to the next patient.

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