Bound Ambition

Chapter One

There was a flurry of excited chatter in the office as the sales department congregated on the lobby floor for an important gathering. The CEO of Kink Couture rarely made his way down to the sales & marketing level of his company, but since the retirement of his former Director of Sales, he had an announcement to make.

Kink Couture was the leading adult toy and entertainment company in the world. Starting with a handful of small sex shops on the liberal West Coast, Ronald Hannity branched out across the country, eventually expanding into films and nightlife entertainment. There was barely a city in the country that didn’t have a Kink Couture store located somewhere in its largest strip mall. While adult entertainment and kink culture had not made it to the mainstream yet, Kink Couture was making inroads in that regard, with the brand being shown in several Hollywood movies. There was inevitable backlash from conservative activists, but sales had been booming.

Sales had boomed so much that the company had recently relocated its headquarters to a 12-floor building in Downtown San Francisco. Part of their success was their ruthless acquisition of the top salespeople in the State. You may believe it would be difficult to sell a vibrator and a butt plug to an eight-year-old lady, but these people made it look easy.

The chatter died down as Mr Hannity took to the stage. He thanked everyone for their tireless contribution to making Kink Couture a resounding success, and promised even greater things would be coming in the near future. He then moved on to the reason he called the meeting. He explained that despite everyone’s hard work, there was one man who shone above all else. “I would like you all to give a resounding applause to our new Salesman of the Year, Brett Norris!” He announced, accompanied by huge hollers and cheers from the thirty people in the room.

Brett made his way up to the makeshift stage and shook his CEO’s hand. Although Brett was a sleight man, measuring just 5’6”, his sharp tongue and charming personality made up for his lack of height. Filled with confidence, he posed for the audience, eliciting laughs from the boisterous salesmen on the floor.

“And that’s not all,” Ronald Hannity interrupted the celebrations. “As you all know, Mr Fritz, our longstanding Director of Sales, retired just a few weeks ago. I am responsible for installing a new director to ensure this department continues to move in the right direction.” There was a pause as Mr Hannity took a breath. “I don’t see any better candidate for the role as Mr Salesman of the Year himself, Brett Norris.”

The announcement bore another round of applause, emphasizing Brett’s popularity around the company. “Brett has already accepted my offer. He has been awarded a one-week vacation to Tahiti as a reward for his efforts this year, but when he returns, I have no doubt he will lead you all to great things!”

Mr Hannity vacated the stage, and Brett mingled with the crowd to accept their congratulations. There was one man standing on the fringes of the audience who didn’t share everyone else’s elation for the appointment. Chris Freeman was the motor that kept the entire department running under the hood. Whereas Brett was exuberant, outspoken, and happy to take credit even if it wasn’t due, Chris was reserved, studious, and glad to allow others to run on his ideas. Everyone except Brett, that was.

He and the new Director of Sales were hired the same week and went through new hire orientation together. They immediately shared a dislike for each other. Where Brett thought Chris had the wrong personality to fit in with the sales department, Chris hated his counterpart’s arrogance and brash views.

Brett looked up and noticed Chris scowling at him from a distance. With a beaming smile, the black-haired sales champion sauntered over to his old rival, taking in the evident animosity shared by his colleague. “Aren’t you going to congratulate me?” Brett taunted the tall brunette.

Where Brett’s height was below average, Chris towered over him at 6’4”. While their colleagues were afraid of teasing Brett over his height in fear of retaliation, they had no issues commenting on Chris’s lanky frame. “I know you stole my sales concepts, Brett.”

Brett feigned astonishment at the comment, placing his hand over his mouth. “I don’t know what you’re talking about, but that sounds like a blatant accusation. I hope you have proof of this.”

His act angered Chris even further, “proof? You used the exact same package pitch in those concepts to pick up the Anderson deal. You don’t deserve to be Salesman of the Year, and you sure as hell don’t deserve a promotion.” The venom coming from Chris’s baritone voice was unmistakable. “I’ll make sure you pay, one way or another.”

Chris simply laughed, “Was that a threat, Chris?” He mocked the tall man. “One more peep from you, and I’ll have you in my office discussing a role that best fits your limited talents.” Brett was enjoying having so much power over a man he despised. “Now, how about you apologize by making me a nice cup of coffee and bringing it to my brand-new office?”

Brett grinned and strolled over towards his large corner office before Chris could find a retort. The tall man watched his arrogant new boss walk away triumphantly before slowly forming a grin on his own face.

❖

Brett opened the door to his new office and smirked at the upgrade. He was never the smartest or most well-studied student, but he had a mouth that could elevate him in any situation. Women loved him; until he inevitably ghosted them, and men admired him. He never thought he would end up working for a sex toy company; he believed that anyone who needed help getting off was just lazy and lacked imagination. Still, he needed a job at the time, and he found he was a natural salesman. Brett figured he would stay in his new role for six months before jumping over to a more respectable industry.

The short man sat in his comfortable new desk chair and loaded his PC. After entering his password, he was alarmed to find his screen going black, before automatically loading a VPN and accessing a strange website. “What the hell, is this a prank?” he said to himself, wondering if someone was playing a practical joke on him or if the former Director of Sales had left a virus on the PC before he retired.

His eyes widened when the website loaded a video with the word ‘LIVE’ flashing in the top right corner of the screen. There was a faint hissing noise sounding in the distance when Brett stared in shock at the image on the computer screen. An extremely busty gothic slut, with piercings and tattoos all over her naked body, was wriggling furiously in a tightly roped hogtie as she was picked up by two burly men and placed inside a wooden box.

The camera panned to a man wearing a suit, with slicked-back black hair and a charming smile. “And that’s all for Bound Ambitions today. Victoria couldn’t quite win the final round, and we will check in on her in a year’s time to see how her new life pans out.” What the hell was Brett watching, he thought as he furiously tapped away at the keyboard, attempting to remove the perverse video.

He picked up the phone to call IT when he heard the man speak again. “Join us tomorrow on DarkWeb TV for the season finale, where Brett Norris will try his hand at winning the $500,000 prize money.” If hearing his name didn’t startle the champion salesman enough, the photo of himself on the screen certainly horrified him. This definitely must be some sick practical joke, he thought.

Brett coughed and felt a little light-headed, and he knew the reason when he tore his head away from his PC screen. While he was staring in horror at the screen, his office was filling with an ominous gas pumping through the air vents. He immediately rose and hurriedly headed towards the door when his legs gave way. Falling over, the new director felt his eyes get blurrier and his strength weakening. Eventually, he succumbed to the gas and passed out in the middle of his new office.

❖

When Brett awoke, he briefly thought he might be dead as a blinding white light attacked his irises. He slowly opened his eyes, adjusting to the bright lights before he noticed that he was in an empty white room. The room reminded him of the type of environment you would place a mental asylum patient to calm them down.

As he moved, he heard the rustling of a chain, which is when he discovered multiple startling revelations at once. First, a metal collar was wrapped around his neck with a chain connecting it to a bolt on the floor. The chain was long enough for Brett to stand but made walking around the sterile white room impossible. A small padlock secured the collar and ensured the unwanted item wouldn’t be removed in a hurry.

Brett rose to his feet and stared down at his body. He no longer wore the sharp navy blue suit he had donned in the office. He was now completely naked, except for a pair of plain white boxer shorts maintaining his modesty. Every other garment of clothing had been stripped from his body.

He also felt a strange sensation from underneath his boxer shorts. There was something uncomfortable wrapped around his cock. Tentatively lowering his boxers to examine the damage, he gasped when he saw the tiny pink chastity cage encased around his poor flaccid member. Brett was always proud of the size of his cock, but this cage made his cock look worthless and pathetic. Another small padlock ensured the cage was staying put, and Brett hastily lifted his shorts back up, covering the source of his humiliation; why the hell would someone do this to him?

It wasn’t long before his thoughts were interrupted by one of the sterile white walls transforming into a large TV screen with a man smiling into the camera. Brett immediately recognized the image as the same man who inexplicably appeared on his PC screen in the office. “Hello, ladies and gentlemen, pervs and pervettes. My name is Hugh Jazz, and this is the season finale of the number one game show on the Dark Web, Bound Ambition!” He excitedly announced.

“Today, we have a special contestant, Mr Brett Norris.” Brett immediately stepped forward when he witnessed a live stream of his body appear on the screen. The chain bolted to the floor forced him back, however. “Mr Norris here is the Director of Sales at our favorite sex toy provider, Kink Couture!” The short man heard a collective gasp as though the host was presenting to a live audience. What kind of sick, elaborate joke is this?

The host continued, “For our first-time viewers, let’s remind ourselves of the format.” Hugh paused momentarily, “Mr Norris will undertake ten separate challenges: five today and five tomorrow. Each round puts one of his body parts on the line, and at the end of said round, that body part will either be restricted in bondage or feminized.” The crowd applauded as the host announced the stakes. “If Brett here wins the round, he gets to choose whether he wants that body part bound or feminized. However, if he loses the challenge, our fantastic audience at home gets to vote on the decision. The audience will also be able to vote on a bonus forfeit with each lost challenge.”

Hugh Jazz waited for the audience cheer to die down before continuing. “That’s not all. There will be three random ‘double jeopardy’ rounds. He will suffer no forfeit if Mr Norris wins one of these rounds. However, if he loses the round, the body part in question will be both bound and feminized. Our lovely audience will also be allowed to choose two bonus forfeits.” Brett pinched himself numerous times; he must have been trapped inside a dream.

“This all culminates in the final round Bound Ambition obstacle course. If Mr Norris can successfully navigate the course within the time limit, his modifications will be reversed, and he will be this season’s first winner of our $500k cash prize!” The audience cheered once again. “If he fails, however, those alterations will remain, and he will suffer the ultimate forfeit.” That outcome seemed to garner an even louder applause.

“We will be back shortly with the first challenge,” The presenter closed out his introduction. “As you wait, let’s look back to our last Bound Ambition winner, who completed his challenge exactly one year ago today. Kyle Jennison was caught cheating on his wife with her best friend. While Kyle managed to win his challenge, the best friend didn’t fare so well in our sister show, Bound Ambition - Female Edition. Roll the clip.”

As the video played, the massive screen on the wall slowly disappeared, leaving Brett to his own thoughts. He tugged harshly on the chain, but it showed no signs of breaking. Whoever organized this practical joke went all out to make it convincing. Brett was preparing to sit down when he heard a loud humming noise, and his surroundings transformed—the sterile white walls, floor, and ceiling all distorted until they created a new environment.

❖

Brett looked on in awe as the entire room around him transformed before his very eyes. Where he once stood inside a featureless bright white room, it now appeared like he was standing on an outdoor basketball court. Was he inside some kind of virtual reality simulation? Is this how this bastard was pulling off the prank?

Somehow, the idea that none of this was real eased his panicked mind. Perhaps Brett just needed to let his asshole colleagues play their game, and he could fire them all when he returned to the office.

“Welcome to round one of the latest edition of Bound Ambition!” Brett heard the host announce to applause, although he couldn’t find a TV screen anywhere. The audio of Hugh’s voice seemed to be coming from every direction. “For this challenge, Brett finds himself on a city basketball court. The task is simple: He must successfully complete 15 free throws before the one-minute timer expires.”

Brett found himself grinning. He played basketball in college and could hit 15 free throws in half that time. If these were the kinds of challenges they would throw at him, they might as well crown him the victor now. “Now, before we begin, let’s spin the wheel and find out which body part is being played for.”

The short, half-naked man couldn’t find any video screen or wheel, but the audio surrounding him told him that something was going on. After a brief moment, the audience gasped before the host announced, “And the first body category is eyes!” Suddenly, Brett felt the padlock securing the chain to his collar disintegrate. Quickly, he unhooked the clasp and found himself able to move freely around the freaky room.

Brett almost decided to make a run for it, but a part of him wanted to prove that he still had the same basketball skills he had in his college days. Instead, he confidently stepped up to the free-throw line with a series of standard-sized basketballs ready for him.

A timer appeared on the basketball hoop’s backboard, and a series of beeps were heard. Brett picked up the first ball in preparation for his first shot, and as soon as the time started ticking down from 60 seconds, he threw the ball.

His first shot landed perfectly, and a number one appeared next to the timer on the hoop. He landed his second and third shots. He had 12 shots left to make, and there were still 51 seconds left.

He landed his fourth shot, but his fifth hit the rim and bounced away. As he picked up the next ball to take his sixth shot, he cried out in pain, keeling over at the waist. The pink cage encasing his cock suddenly emitted an electric shock. “What the fuck!” He screamed out. He was in agony and felt pure anger, but as he watched the seconds tick down, he knew he needed to finish the challenge.

He regained his composure and landed the next couple of shots. He had 25 seconds left with 5 shots remaining when he missed his second attempt and felt the agonizing jolt run through his crotch. “You fucking assholes!” Brett screamed, taking another shot and missing again. The following shock was more potent than the last and caused the short man to drop to one knee. He suddenly only had eight seconds remaining with 5 shots to go.

Resolving himself to finish the task, Brett stood back up and threw his remaining shots, landing the first and second. He had one shot left with two seconds remaining. He launched the ball into the air and gasped when it hit the rim, but it circled the hoop and somehow managed to sink with one second left on the clock.

Brett celebrated, momentarily forgetting the pain in his crotch or his embarrassing state of dress. He had won the challenge. “Congratulations, Brett. We have a real competitor on our hands here,” Hugh Jazz announced over the speaker. “Now it’s time to choose your own destiny. Eyes: Bondage or Feminize?”

What kind of game was this where he was still forced to receive a punishment after winning a challenge, Brett thought. He wasn’t sure what would happen if he refused to decide, but he imagined they had a failsafe for that scenario. He thought carefully about each action. If he feminized them, would they cover him in makeup? What could they really do to make his eyes look more feminine? On the other hand, if he chooses the bondage option, the realistic option would be to blindfold him. Brett knew the remaining nine challenges would be arduous if he couldn’t see what he was doing, so there was only one realistic choice. “I choose to feminize them.” He spoke with as much masculine charm as he could.

“Ladies and gentlemen, our contestant has chosen to feminize his eyes!” Hugh announced with charisma. “Start up the Transformer.” He commanded, and Brett waited for something to happen. Just as he was about to laugh, perhaps this being the final act of the elaborate practical joke, he felt a tickling around his eyes and along his eyeballs. Brett’s vision blurred as an invisible force pricked and prodded around his furious brown eyes.

When his vision cleared again, the strange intrusive sensations had disappeared. The room had also transformed again, this time into a mirrored room where he could see himself from every angle. He stared at his reflection and gasped sharply at what he saw. Stepping closer to one of the mirrors, he noticed with horror that they hadn’t just decorated his eyes with a bit of makeup; they looked completely different.

His eyes were wide and expressive, ultimately portraying the shock he was feeling. His dark, bushy eyebrows were now lighter in color and trimmed into an extremely thin, high arch. His eyes were no longer brown but a sparkling blue that didn’t appear totally natural. His eyelashes were darker and at least double in length. The entire visage changed his facial appearance far more than he could have imagined, making him furious.

“Very funny. I’ve had enough of this stupid joke now.” Brett spat out, “Change me back.” He demanded, looking up at the ceiling where a small display of the live show had appeared.

The man in the display laughed, “Usually, the contestant pleads to be let go before he completes the first challenge. I was starting to think you sponsored yourself.” Brett groaned at his comment. If this was a dream or an elaborate joke, it had gone on far enough. “Now, are you ready for round two?”

❖

Hugh Jazz didn’t allow Brett to respond, and the room altered its environment again. This time, Brett felt the sand between his toes and smelt the fresh sea breeze, the room modifying itself into the facade of a sunny sandy beach.

To the short man’s horror, he felt two metal poles extend from the collar around his neck and connect to two poles rising from the sand, trapping him on the spot. Strangely, a pair of swimming goggles wrapped themselves around his head and over his feminized eyes. ‘This was some crazy advanced VR technology,’ Brett thought as he tried to escape his padlocked collar.

“Round Two is our beach endurance round.” The host announced to his audience. “Above Mr Norris, you will see a large tank of water. When the timer starts, the tank will lower, and his head will slide through the watertight gap underneath, submerging himself underwater. Mr Norris must hold his breath for two minutes to successfully complete the challenge.” Brett didn’t like the sound of that; he was never the greatest at holding his breath underwater. “There is an automatic release button on the side of the tank. If Mr Norris presses that, the water will drain away, but he will lose the task.”

“Let’s see what Brett will be risking in this challenge.” Brett heard the sound of the spinning wheel once more and waited impatiently for it to stop. He listened to the rapturous applause of the audience before Hugh spoke again. “It looks like his chest will be up for grabs this time, always a crowd pleaser.” Brett cringed as Hugh laughed at his own joke.

“Now, Mr Norris. Are you ready for round two to begin?” The host asked but laughed when Brett urgently told him to wait. “It was more of a rhetorical question, Mr. Norris.” Without warning, the tank descended over Brett’s head, slipping his entire skull into the pool of water.

Brett held his breath intently and watched a small clock in the upper corner of his goggles start to tick down. This was probably going to be the longest two minutes of his life.

Thirty seconds into the challenge, Brett felt pretty good. The longer that clock ticked down, the more confident the sales director was that he would complete the task. Everything changed when the time dropped to sixty seconds, however. Suddenly, his goggles went pitch black until an image of his old college dorm room appeared as if he was watching it on TV. Why would they show him his old dorm room?

The camera panned over to the bed, where he heard the same familiar ecstatic cry he had heard a hundred times before. His ex-girlfriend Kayleigh Carter was lying on the mattress, being fucked senseless. Kayleigh was the one who got away for Brett. He had planned their entire life together, but she broke up with him soon after graduation; it had taken him a year to recover. That rejection was part of the reason Brett had such a low opinion of women now, and he swore to himself that he’d never put himself in that vulnerable position again.

Brett’s expressive eyes widened when he saw the man fucking his fictional ex-girlfriend. It was not an image of himself, but of his work rival, Chris Freeman. That son of a bitch was fucking the only woman he truly loved. “No!” he screamed out, knowing immediately how much he fucked up, choking on the water rushing down his throat. Brett attempted to close his mouth again, but too much H2O had flowed inside him, and he coughed, making it ten times worse when the cough opened up his throat. Finding no other alternative if he didn’t want to choke to death, Brett hammered the emergency release button, and the bottom of the tank opened, releasing the water and allowing the sleight-statured man to breathe.

Brett was still gasping for air when the host wasted no time addressing the audience: “Unfortunately, Mr Norris has failed his task. That means it’s up to all of you to decide his punishment. Breasts; Bondage or Feminize!”

Groaning, Brett hated the idea of someone else choosing his fate. He had already resolved to select the bondage option if he had won. He figured it would be much more difficult and less humiliating to bind his chest than the alternative would be. His heart sank when he heard the results. “This one was pretty much a foregone conclusion. With 96% of the vote, the audience chooses Feminization!” Brett shook his head, but the host wasn’t done. “While the Transformer does its thing, it’s time to vote on that bonus punishment.”

“Wait,” Brett demanded, immediately feeling a tingling pinprick sensation around his chest. His surroundings transformed back into the mirrored room, but the short man was solely focused on the unusual feeling covering his upper torso.

His chest started to expand, gently budding into feminine A-cup breasts before stopping. Brett looked down, horrified at his transformed chest, when he heard that infuriating host speak again. “You didn’t believe we’d stop there, did you?” Brett clenched his fists when he heard the audience rumble into laughter, the expansion on his chest resuming up to a B-cup and then a C-cup and further.

While the horrified black-haired man’s chest continued to explode in size, Brett’s environment reverted to the previous mirrored space, forcing him to stare at his helpless predicament from every angle. The mounds on his chest appeared huge from his point of view as they passed DD-cups, still growing large.

Eventually, the uncomfortable tingling stopped, and his breasts settled at their unbelievable F-cup size. It wasn’t just the size that caught Brett’s eye. These perfectly round basketballs sat high on his chest, protruding outwards proudly. He had only ever seen tits this perfectly shaped on porn stars before, with the obvious help of surgery.

“What have you done?!” Brett shouted, unable to resist the urge to cup them. His cock attempted to strain in its confined cage at the size of such perfect bimbo tits, which caused him to gasp in pain. His gasp grew louder when he felt something sharp pinch his newly extended nipples. Staring in the mirror, Brett found two gold hooped rings pierced in his transformed teats. Touching them, he immediately pulled his hands away as he shuddered with an unusual pleasure. They were extremely sensitive.

“Mr. Norris here now sports a pair of fantastic F-cup silicone-enhanced boobies, and I notice he has already discovered the audience’s extra gift; a pair of decorative hooped nipple piercings.” The crowd erupted in more applause.

“Fuck you all,” Brett spat in reaction to the clapping. “I am done with this. This is over!” He demanded, pushing against one of the mirrors, hoping to find a secret door.

Hugh Jazz laughed over the sound system. “Ohh, Mr Norris, we still have eight rounds to go. But don’t worry, you look great.” The charismatic host teased. “Now, let’s move on to round three.”

❖

Brett wasn’t prepared to stand idly by as these sick, twisted perverts transformed his body with advanced, alien technology. He was still convinced that this was inside his head, but the sensations and the humiliation felt all too real.

He started banging his fists against the mirror, expecting the glass to smash into pieces, but his busty reflection remained intact. After attempting to destroy his reflection a third time, the entrapped man felt a sharp, painful jolting shock from his chastity cage brought him to his knees.

“Please don’t damage the costly set, Mr Norris.” The host asked him nonchalantly. Brett retaliated by screaming obscenities at the display on the ceiling. “It’s time to move on,” Hugh announced, and Brett felt his surroundings distort once more. More worryingly, as the new environment settled, the busty man found his hands had been handcuffed behind his back.

“What is the meaning of this?!” Brett growled. He appeared to be in some changing room. Looking at the logo above the mirror, he discovered that he was in the fitting room of one of his very own Kink Couture stores. More alarmingly were the multiple objects protruding from the wall opposite him.

“Usually, we take things up a level after round four, but as you seem intent on destroying our beautiful set, we believe you are ready for the challenge right now.” Brett swallowed; the words sounded highly ominous. “You will find five phallic objects pinned to the wall, each increasing in size. You have ten minutes to perform fellatio on each penis until the green light above it turns on. If you satisfy all five cocks before the timer runs out, you win.”

Brett stood in the tiny fitting room, horrified. “Wait, there is no way I’m-”

The impatient host cut him off. “We don’t have time for tantrums, Mr. Norris. Now, let’s see what you are risking this time.” Brett grunted at his objection being cut short. The wheel span again, and while the black-haired sales champion couldn’t witness the wheel itself, he soon heard the outcome. “Ohh, and this time, you will be competing for your hair.”

Brett was happy with his hair. His jet-black tussle oozed confidence and authority, and his barber worked wonders, keeping it sharp and healthy. He certainly didn’t want anyone messing with his hair. A series of beeps disturbed Brett from his own thoughts, and he saw the ten-minute timer start to count down.

Did they honestly expect him to place his lips around a plastic cock? He wasn’t gay, nor was he some prancing sissy. Whoever had set this up had done it purely to humiliate their new boss. He folded his arms and gasped when he was reminded of the sensitive mounds of flesh he now sported on his chest. There was no way he was going to succumb to sucking a cock for anybody.

The busty man anxiously stared at the time; it had already ticked down to seven minutes. He shook his head stubbornly, but as it sank to the five-minute mark, Brett started wondering how severe his punishment would be if the audience chose it. The last challenge he lost left him with gigantic basketballs on his chest.

Reluctantly, he dropped to his knees and wrapped his lips around the rubber shaft. He gagged as he tried to push the cock in deeper, but his throat resisted him at every attempt. The cock wasn’t even particularly large, perhaps the average size for a man, and definitely smaller than the one trapped inside the pink cage. After several more attempts, Brett felt a strange sense of relief when his throat opened up and allowed the cock to enter.

Brett picked up the pace, deepthroating the 6” pink rubber shaft, feeling the plastic phallus warm up inside his mouth until he felt something warm and salty shoot down his unprepared throat, almost choking in the process. The light above the dildo turned green, and Brett immediately withdrew his mouth, only to be greeted by a shot of manufactured cum in his face.

Brett didn’t have time to dwell on the disgusting taste in his mouth, and he shuffled over to the 7” purple member beside the more petite cock. Once his lips wrapped around the plastic shaft, he shuddered when he heard a sudden buzzer. Somehow, his time had expired already.

“Well, well, well, that was a pitiful attempt, Mr Norris.” He heard the smug host announce. “In fact, it was perhaps the worst performance I have ever seen.” How had it been ten minutes already? Most of his ex-girlfriends could get him off in about 3 minutes with their skillful tongue. “It’s time for the audience to decide. Hair: Bondage or Feminize!”

He rose to his feet in despair, the environment around him reconfiguring into the mirrored room he had become accustomed to. The cum on his face and inside his mouth had gratefully disappeared as the scenery changed. He didn’t have to wait long until Hugh returned with the results. “With 74% of the vote, the winner is Feminize!” He announced to another round of applause. Brett clenched his fists. While he figured the less he was bound, the easier it would be to complete the final obstacle course, what would they have done to bind her short black hair? Bondage would have been the more favorable choice for him.

His now uncuffed hands absently jolted to his head as every hair follicle began to vibrate and tickle. As if by magic, the hair on his scalp began to grow, lengthening further down his neck, towards his midback. As his hair lengthened, it also began to lighten, first into a mousy brown and then a golden blond, until it lightened into a bright platinum blond shade. “You sonofabitch!” Brett screamed out, horrified at the sight in front of him.

His torment wasn’t done yet, as two rubber hairbands expertly wrapped themselves around his loose hair, forming two tall pigtails on top of his head. He looked ridiculous. He was undeniably a man with his masculine sculpted face and six-pack abs, but the huge plastic tits on his chest mixed with the juvenile platinum blond pigtails atop his head gave the sales director a comical look, although he couldn’t find the funny side himself. “Undo this right now, you bastards! I didn’t sign up for this shit.” His words were cut short when he felt something tickle inside her throat, as well as his rectum. His large, expressive eyes widened in shock as he contemplated what had just happened.

“Ohh, that’s your bonus punishment kicking in. Your throat and rectum have become perfect g-spots. You’ll likely never have a problem sucking a cock again.” The host teased, “That would have probably been useful during the last round.” He laughed.

The resonance of laughter enraged Brett even further. Still, there was little he could do trapped in this mysterious room with no apparent escape route. “Anyway, we can talk about your agreements after the contest. For now, we need to move on to round four.” Hugh Jazz dismissed Brett’s insults and pressed on.

❖

Brett was busy attempting to loosen the devious hairbands when his surroundings changed once more. He tried to pull out one band using both hands, but the rubber band wouldn’t budge; it was as though they were fastened to his new hair using industrial-strength glue.

When the newly blond, busty man gave up on destroying his new hairdo, he found himself inside a hotel room with a delicious sight bound to the bed. With her arms and legs outstretched with rope, a mysterious redheaded woman lay naked on the plush bed. Her eyes were blindfolded, and a red ball gag was fastened between her lips. I looked as though she was presented to Billy as a gift.

“Welcome to round four.” He heard the host announce over the hotel room speaker. “This round is called Hote-” Hugh’s monologue was interrupted by a sudden siren sounding over the speakers and another raucous applause from the audience. Brett looked around, perplexed. “Ohhhh, you know what that means. We have ourselves a double jeopardy round. Where the contestant has the chance of completing the round completely scott-free, or they could end up in more trouble than they can handle.” Brett felt his stomach drop and his body shudder. The stakes had just been raised.

“This round is called Bedroom Pleasures, and the task is simple. A beautiful woman is spread out on your bed, just waiting to receive the greatest orgasm of her life, and she needs you to give it to her.” Brett raised his thinly arched eyebrow. “All you have to do is bring this lovely lady to orgasm before the five-minute timer expires. I’m sure a man of your talents would find this super easy. Speaking of which, it’s time to lose the modesty.” The presenter declared before Brett’s white boxer shorts disappeared into thin air, exposing his tiny pink cage to the entire audience.

The anger in Brett’s large, expressive eyes was easy to see as the audience laughed at his predicament. “Ohh, that may be a problem. I like the color, though.” The announcer poked fun at the impotent contestant. “Anyway, let’s see what body part you are playing this special double jeopardy round for.”

As Brett heard the wheel spin, he attempted to tug off the cage. A small padlock kept it together, but the more he pulled, the more he felt as though his balls were about to be ripped off. The cage was well and truly secured. He heard another ovation from the audience and knew by now that usually meant bad things for him. “And the lucky wheel has chosen Lips!” What the hell? Brett had lost the last two challenges, but he knew he needed to win this one.

“Let’s see what this stud is made of,” Brett heard Hugh announce in a patronizing tone, “Ohh, and using your hands is not allowed.” Brett gasped as a pair of tight-fitted leather mittens appeared on both hands, rendering them useless. Before Brett could react to the revelation, a series of beeps indicated the start of the round; an alarm clock on the bedside table started ticking down from 5 minutes.

Unlike his last challenge, Brett wasted no time in getting started this time around. He pounced on the bed and immediately slid his hands along her thighs. The unknown woman reacted to his touch and garbled unintelligible words through her gag. The hotshot salesman attempted to rip the cage off one last time, but it was as successful as his previous attempts. In a panic, he endeavored to push the cage itself inside the woman’s pussy. He tried for a good 45 seconds, but the angle and shape of the cage made it impossible for him to use it as a tool.

He experimented with the new mittens on his hand, trying to slide them inside her at every angle, but they were too clunky and wide. Brett groaned in frustration, “You fucking assholes!” he shouted to no one in particular. Brett looked around the hotel room, but they had left nothing that would help bring this woman to orgasm.

With only two minutes remaining, Brett used the only remaining appendage he could think of: his tongue. The blond, busty man had always despised licking out a woman’s pussy. He believed it was the woman’s job to bring her partner to pleasure, and there was no point satisfying her if he would gain nothing in return.

Crouching between her legs, Brett swallowed his pride and pressed his tongue between the woman’s bare lips. Brett tried hitting numerous spots, including her tiny clit, but the redhead barely reacted to his touches. His inexperience at cunnilingus proved to be his downfall, and he cried out in desperation when the buzzer indicated he had run out of time.

Brett dropped to his knees as the hotel room and the bound woman disappeared before his very eyes. Crestfallen, he saw his ridiculous hair and breasts in the reappearing mirrors. “Looks like another failure, and we all know what that mea-”

“No! You listen here!” Brett stood up. The mittens on his hands had also vanished. “This game has been rigged against me, and I won’t stand for it anymore. If you wanted me to compete, you better damn well make sshhuu-” The blond man was unable to finish his sentence before tiny pinpricks circled his lips, causing a numbness around his kissers.

“I don’t like being interrupted, but that may not be a problem anymore,” the host ridiculed his busty contestant. “Anyway, let me finish. Lips: Bondage AND Feminize!” He joyously exclaimed to yet enough boisterous cheer from the audience, perhaps their most passionate yet.

Brett approached one of the mirrored walls and watched on helplessly as his thin lips exploded in size, and his expression grew poutier with each expansion. Within moments, the highly successful sales director was left with a pair of luscious, fleshy cocksucking lips. His natural pout, merged with his wide, blue eyes and pigtailed platinum blond hair, gave the man a sultry, dumb expression. Although his face still had masculine features, most people staring at his face would mistake him for a woman, an incredibly dumb woman at that.

The moment Brett parted his lips to retaliate, he felt a rigid piece of plastic expand inside his mouth. He attempted to close his mouth again, but it was too late. The plastic ring expanded until his mouth was fully open, and two straps wrapped around his head, merging at the back of his skull before a tiny padlock secured the ring gag in place. “Agghhhh!” He cried out, lifting his hands and tugging on the firm straps.

“Now that’s much better,” the host teased. “And I wouldn’t waste your strength. Those straps are made with the most advanced compound we know of. You would burn your face off before you make a dent into those bands.

Brett ignored the host and continued attempting to pry apart his new ring gag, keeping his new slutty lips spread open. “We also have the two bonus punishments to take care of, and our audience has made their decision.” Brett cried out when he suddenly felt a harsh pinch on his tongue. His eyes widened, but not because of the pain; the gagged cry he heard was not his voice.

Hugh Jazz chuckled at the dumbfounded expression on the pigtailed man’s feminized face. “That’s a cute little soprano you have there, cutie.” He dialed up the tease even further. “While you may not be able to speak properly for the foreseeable future, you now have a cute little high-pitched voice, fitting the bimbo you now look like.”

“Aghh Unghhh!” Brett tried to speak, but his cheeks blushed red from the humiliation of his new bimbo voice.

“And why did you squeak in the first place, baby girl?” the presenter continued. “Is it because of that cute little stud on your tongue? The boys are going to love that along their cocks.” His comment elicited a round of laughter from the audience.

Brett stared at himself in the mirror and failed to believe it was him he was looking at. Everything felt so real, but none of this made sense. He had to be in the middle of some nightmare. “How about we move on to the day’s final round, and it’s a good one.”

❖

Brett’s image in the mirror disappeared, and he stared in horror at the tiny, filthy toilet cubicle he suddenly found himself in. The lighting was dim, and lewd graffiti was painted all over the walls. The most unnerving item in the scene was the 7” black dildo attached to the toilet seat in front of the gagged man.

“Welcome to round five; truck stop satisfaction.” He heard the sadistic voice of the announcer again. “This round is straightforward. In the previous round, you failed to bring your partner to orgasm. Let’s see how well you can get yourself off.” Brett didn’t like where this was going. “You have five minutes to make yourself cum using only the items in this room. Let’s see which body part you are putting on the line this time.”

Brett had to bend over to look past his over-inflated tits and stare at his helplessly caged cock. How was he going to orgasm with that damn device on his cock? He heard the wheel stop and the perverted presenter announce the new stakes. “For round five, you will be risking your waist.” The crowd applauded, though not as exuberantly as the previous round.

Without another word from the host, the hapless Brett caught the beeps indicating the start of the round, and a digital clock above the toilet started to count down. Brett immediately grabbed his caged cock and furiously attempted to stroke the semi-flaccid member.

Brett had no idea how these chastity cages worked, but surely there was enough give on them to give himself a little bit of pleasure. However, after wasting 90 seconds with his hand wrapped around the rigid plastic prison, he was no closer to orgasm.

The busty, gagged man stared at the large dildo protruding from the toilet seat. He knew what the show wanted him to do, but he couldn’t stomach the idea of having anything in his ass. Then he suddenly remembered something the host had said two rounds ago. His throat had been turned into a g-spot. With his new ability to open up his throat, he could probably bring himself to orgasm by sucking on the dildo.

Kneeling in front of the dirty toilet seat, Brett took a deep breath before wrapping his wide open mouth around the shaft. The moment the feminized man’s tongue pressed against the plastic cock, Brett felt a familiar jolt in his crotch as the chastity cage shocked him again. The jolt wouldn’t subside until the blond man lifted his head completely off the dildo. He sighed, looking up at the clock. He only had three minutes remaining.

“Aghh Ughheer!” He cried out in his new bimbo tone. Those bastards were not playing fair. With only one other option, Brett knew he needed to start winning challenges, and he stood up and gently began to lower himself on the long dildo.

“Aghh!” He moaned out, feeling his tight ass resisting the presence of the black rubber dong. The saliva from his tongue eventually helped him reluctantly slide the member further down until his bimbo eyes widened in wonder; he felt a brief jolt of pleasure.

Brett methodically slid his ass up and down the shaft, feeling an unusual sensuous bliss he had never experienced before. With only sixty seconds remaining, Brett kicked it up a gear, bouncing himself on the cock, with lustful, slutty moans escaping his wide-open bimbo lips. He cupped his new fake breasts, squeezing them together. The pleasurable sensations took the feminized salesman over the edge, and all thought vacated his mind.

As his cock suddenly pulsed inside its cage and shot its load, Brett’s tongue poked out, and his wide eyes crossed in a dumb ahegao expression. His gagged face elicited laughs from the watching audience, but Brett didn’t care at that moment; it was the most intense orgasm he ever had.

The orgasm eventually subsided, and Brett’s tongue contracted back inside his open mouth. He pulled himself from the rubber shaft, and his weakened knees caused him to stumble. The further he was brought down from the orgasm, the more humiliated he felt. Why the hell did he act like that? He wasn’t some sissy loser.

“Congratulations, Mr Norris, on winning this round.” Hugh Jazz interrupted the contestant’s humiliated stupor. “You finally get to choose your own forfeit. Waist: Bondage or Feminize!”

Brett certainly didn’t want to go further with this whorish look he had adopted, and he was mightily proud of his six-pack. He knew if he chose feminization, his well-muscled waist would be a thing of the past. There was only one other option. “Ung-ujj,” the bimbo-looking man replied.

“Uhmm, excuse me?” Hugh condescendingly responded. “I didn’t quite get that.”

“Ung-ugg, ung-ujj!” Brett screamed frustratedly in his high-pitched voice. Suddenly, a pen and paper appeared in the naked man’s hands, and he was able to write ‘Bondage’.

“Okay, bondage it is.” The host confirmed, and it didn’t take long before Brett felt a tightness around his musclebound waist. At first, he thought they went back on their word and began to feminize his midriff, but as he bent down and saw past his impossible breasts, he noticed a bright pink corset forming around his waist.

“Aghhhh!” he cried out, laces automatically cinching the steal-boned corset tighter, crushing his waist. When it had tightened as far as it possibly could, Brett still appeared to have an alluring hourglass figure despite his six-pack hiding underneath the confining attire. His breasts impossibly perked up even more as the boned lining of the undergarment propped them up further. Small decorative padlocks lined up both sides of Brett’s new corset, ensuring he would be escaping in a hurry.

The horrified blond-haired man was forced to take smaller, more frequent breaths, and he ran his hands over the constraining garment helplessly. “Ughh aghhh,” he tried to plea, but his appeals were no longer coherent.

“Well, doesn’t that look gorgeous?” the host teased. “And that’s all we have time for today, folks. Join us tomorrow for the final installment of the season finale of Bound Ambitions.” Brett heard further applause and a jingle playing in the background before the filthy toilet scene faded. Brett soon found himself back in the sterile white room from which he had initially awoken. A weight against his neck told him the chain originally connected to his collar had also returned.

❖

Brett failed several attempts at yanking the chain from its secured base. He was eventually interrupted from his effort when a door opened that Brett hadn’t noticed before. It was his first clue that there was an escape from this despicable prison.

Brett heard a slow clapping applause building in volume as the silhouette of a suited man approached ever closer. “Ooghh!” the pigtailed blond cried out when he noticed the charming and punchable face of the gameshow host, Hugh Jazz.

The busty man wasted no time running in the man’s direction, momentarily forgetting about the chain connected to his neck and almost strangling himself when the chain pulled taut and stopped Brett in his tracks.

“Congratulations,” The host said, unfazed, stopping just out of reach of the gagged man’s hands. “You may be on course for our highest-rated show ever. It will keep the advertisers happy; your company is one of them.” He taunted with a grin.

Brett tried again to reach for the sadistic gameshow host but couldn’t quite reach. The man was amused by his attempts. “Now, tell me, Brett. After today, do you believe in magic?” Hugh took one step forward as if to bait the hapless blond into acting. Brett promptly took the bait and swung a right hook toward the smug host. Before the fist could land, Hugh clicked his fingers, and Brett’s bimbo eyes widened as he found his hands suddenly cuffed behind his back.

With one more click of his fingers, the chain attached to Brett’s collar began retracting until he was forced down to his knees directly beside the base. Hugh clicked his fingers again, and a clean, thin mattress appeared by Brett’s side. The host dropped down to one knee and gave Brett’s newly pierced nipple a squeeze. “This is my show, and we play by my rules, understand?” He looked into Brett’s new bright blue eyes but didn’t wait for a response.

“Tomorrow, you have a chance to put all this right and walk out of here a free man, $500k richer.” The presenter grinned. “Now, get a good night’s rest. You need all the luck you can get.” He commanded before clicking his fingers, and an object appeared in his hand. To Brett’s bemusement, Hugh slid a phallic rubber dildo inside Brett’s mouth until the end of the device was in line with his ring gag. With one twist, the dildo secured into place as if it were built for the gag. Brett looked back at him furiously, wrestling against the cuffs behind him; the gag was long enough to completely fill his mouth but not quite long enough to trigger his new g-spot.

Hugh stood up and dusted himself off. “Goodnight, Brett. Sweet dreams.” He taunted, walking back towards the open door. He clicked his fingers one more time before exiting the room, simultaneously removing Brett’s handcuffs and switching the lights off, succumbing the gagged, feminized man into darkness. Hopefully, tomorrow will bring a more positive outcome.

End of Chapter One