Bound Ambition

Chapter Two

The following morning, a gagged and half-feminized Brett was awoken by the bright white lights of his prison reactivating. Stirring from his uncomfortable slumber, he soon discovered the plug trapped inside his mouth had disappeared, although the ring gag keeping his newly enhanced, plush lips apart remained in place.

He was still naked, with an uncomfortable pink plastic chastity cage keeping his impressive member in a confined, shriveled state. The metal chain connecting his collar to the floor had lengthened, allowing him freedom to stand. The mixture of his enhanced lips, the big blue doe-like eyes, and his newly colored platinum blond hair styled in ridiculous pigtails contrasted with the masculine physique of the rest of his body. The corset constricted his toned waist into a feminine silhouette, and the enormous fake bare breasts on his chest were impossible to hide.

He had been drugged a couple of days earlier and forced to compete in a horrific game show being broadcast on the dark web. He was coerced into competing in a series of challenges, with the ‘prize’ resulting in a part of his body being either feminized or entangled in bondage.

The results of his day one challenge had left his face looking far more like a vapid bimbo than he ever would have dreamed of. The ring gag forced into his mouth and the aforementioned corset around his waist were the lasting results of bondage on his body.

“Perverted ladies and gentlemen, welcome back to day two of the season finale of our favorite game show, Bound Ambition!” Brett glanced up as the self-assured voice of the presenter boomed around the sterile white room. The host revealed himself to Brett last night after the cameras went down and demonstrated his very real ability to manipulate items around him using real magic. That encounter terrified Brett more than anything; it wasn’t all happening inside his pretty blond head.

“Are you ready for Round Six?” The host asked the invisible audience. Brett’s alluring blue eyes widened when a chorus of cheers filtered around him, giving him no time to fully waken and study his surroundings.

“Arghh Anggg!” Brett garbled through his ring gag in protest as the room completely altered around him. The helpless man immediately found himself inside a black and red-themed BDSM dungeon, with all kinds of pain-inducing tools hung up on the wall.

Even more alarmingly, Brett had changed position himself. The naked man was now fully bent over a leather-clad horizontal bar connected to two posts protruding from the floor. Metal cuffs wrapped around his ankles and fastened them to the ground. His wrists were decorated in the same style of cuffs, also stapled to the ground, making it impossible for the poor man to lift himself from the bench.

As Brett tugged on the sturdy cuffs, the host continued to explain. “The Spanker Challenge is a firm fan favorite. I’m sure our lovely contestant will enjoy competing as much as we enjoy watching.” He said, eliciting a roar of laughter from the audience. Brett didn’t like where this was going. “Our lovely assistant, Mistress Domina, will visit our contestant and deliver ten progressively more severe spanks on his backside. A big red button is within reach of our blond beauty’s right hand. If the contestant can’t take any further pain at any time, he may press the button. If he presses the button, the round will be over, and he will have lost the challenge.”

Brett pulled on his wrist and ankle restraints more firmly. He had an extremely low pain threshold and hated where this challenge was headed. He gasped through his ring gag when he looked up and saw a gorgeous, busty redhead wearing a glossy black catsuit enter the room. He groaned as his cock uncomfortably twitched inside the bright pink chastity cage when he saw the beautiful woman approach him.

He witnessed the unknown redhead grin when she noticed the trapped contestant struggling against his bonds. Mistress Domina casually strutted out of sight, running her gloved hand along the prisoner’s backside in a teasing manner. Brett shuddered at her touch and helplessly groaned as his shriveled penis had no room to grow inside its confining cage.

“Aghhh!” He cried out as her hand harshly made contact with Brett’s exposed ass without any warning. The helpless blond saw a digital display on a TV ahead of him, showing the words ‘1/10’. He cried out again as the hand made contact a second time with a more ferocious impact. His eyes almost bulged out of his head when he was spanked painfully a third time. He still had seven spankings to go, and his ass already felt incredibly tender.

There was a pause, allowing Brett a brief moment of mercy. He stared at the TV displaying the words ‘3/10’. Brett bit down on the ring gag, forcing his lips apart and sensing the redheaded Domme’s presence behind him. “Aghhhh!” he cried out painfully. She had spanked him with a leather paddle, far more painfully than the three spanks he received earlier. Another excruciating sting to his ass came next, followed by another in quick succession.

Brett came close to reaching out for the large red button ahead of him, but with three challenges lost already, he was determined to have some agency over his transformations. There was a second pause, but Brett didn’t feel as content to be left alone this time; he knew what she was doing.

“Agh ungghhh!” A tear fell from the blond prisoner’s eye as he felt the contact of multiple thin cords strike against his tender backside. The Domme had moved on to a cat-o-nine tails to administer the punishment. The Domme softly caressed his bright red tender asscheeks with her gloved hand, giving the man a brief moment of respite.

The moment didn’t last long, however, as the whip struck against his ass a second time, and a third. With only one spank to go, Brett willed himself not to press the mercy button with all his might. He was almost done.

Brett was nervous about how long the beautiful latex-clad woman had left him waiting. His big fake tits hung loosely on his chest. Despite his bent-over position, his tits defied gravity and kept themselves held high and firm on his chest. “Aggghhhhhhh!” the transformed man screamed. The sadistic Domme had struck him with a riding whip, delivering a sharp, concentrated sting across his asscheeks. That final sting left a mark across his reddened backside.

With his entire body shuddering, the prisoner witnessed the display thankfully ticking up to ‘10/10’. The Dominant assistant stepped back in front of the cuffed man and ruffled his blond, pigtailed hair before grinning and stepping back through the door she entered from.

Once the door slammed shut, Brett suddenly fell to the ground as the spanking post vanished in thin air. His cuff restraints also disappeared, leaving the blond contestant in a writhing mess on the floor. The host gave Brett a moment to compose himself before continuing the game.

“Congratulations, Brett. I think it was touch and go for a moment there, but you survived the ten lashes and have been awarded the opportunity to choose your own transformation. Your selected body part is….” There was a tense pause as a spinning wheel was heard around the dungeon. “…ears!” The presenter declared, eliciting a smattering of applause from the audience. The transformation of the ears was clearly not a fan favorite.

“So what is it going to be?” Hugh Jazz asked, “Will your ears be feminized, or will you choose bondage?” Brett struggled to rise back to his knees, staring at the two options on display in front of him. He didn’t want any further feminization, but if he chose bondage, he would likely be deaf as he tried to fight his way through the remaining challenges. He knew there was only one sensible option. “Enghhinghiff,” he called out, his gag stifling his speech.

“I’m sorry, Mr. Norris, but I didn’t quite understand your answer,” Brett narrowed his eyes as the host mocked him, and the audience laughed at his plight. Groaning through the ring in his mouth, he pointed at the feminization option on the screen.

Immediately after he made his choice, Brett felt the room morph around him into the now familiar mirrored transformation room. He couldn’t hide his ridiculous new look from his eyes as the mirrors on each wall and the ceiling demonstrated just how transformed he indeed was. He felt his ears heat up and tingle, staring as they shrank into cute little ears. His lobes warmed up, and the unwilling contestant felt a sudden sting. He witnessed the trashy bright pink plastic hoop earrings materialize and decorate his new pretty ears. He gently raised his hand, tugged on one of the cheap-looking hoops, and gasped. “Those pretty earrings are designed with a specially designed indestructible material, and there is no free clasp. You will have plenty of trouble tugging those things off if you still want to keep your ears.

“I’m sure you would like to spend all day ogling yourself, but we have a game show to get back to,” Hugh teased his helpless contestant. Suddenly, the room transformed once again to signal the start of Round Seven.

❖

Once the room had fully transformed, Brett found himself positioned in a high-back armchair. His legs were bound to the chair’s leg, and straps kept his wrists firmly secured to the arms. Two straps were wrapped above and below the contestant’s impressive bare tits. Alarmingly, Brett felt an object wedged between his spread legs and propped up against his plastic cage.

The room itself was colorful, with pinks and yellows decorating the walls. It looked like the set of an old game show from the 1980s. “Welcome to my personal favorite round, the Trivia Round!” Brett tested out his bondage as the cheer of the audience was deafening. “The rules are simple. Brett gets to show off that big brain that won his recent promotion by answering a series of questions. He needs to correctly answer 7 of the 10 questions to successfully complete the challenge. If he answers four questions incorrectly, the round ends and the audience will choose his fate.”

The crowd applauded again at the prospect of furthering Brett’s humiliation. Still, their cheers were drowned out by a loud siren engulfing the room. “Whoa, whoa, whoa…” Hugh interjected. “You all know what that means. This round has been randomly selected as a double jeopardy round.” The crowd cheered again. “The stakes have never been higher. If Brett wins this challenge, he will move on to the next round unscathed. However, if he loses, one part of his body will endure both feminization and bondage.”

Brett shuddered. He was intelligent and confident his trivia skills would carry him through, but the double jeopardy added an extra layer of risk. “Are we ready to begin?” Hugh asked before a chime signaled the start of the round.

“What is the name of the ancient Hindu text that explores sexual pleasure and techniques, including BDSM practices?” Hugh Jazz asked, with the question appearing on a screen before him. Brett grinned inside. He hoped that every question was as easy as the first.

“De Kaw-mah Soo-tawww!” He exclaimed. The gag inside his mouth made enunciating his answers incredibly difficult, and he soon discovered how detrimental that fact would be.

“Aughh, so close.” Brett declared. “You answered De Korma Sootor. However, the correct answer is The Karma Sutra.” Brett’s eyes widened, and the crowd cheered and laughed. How was this fair? He knew the correct answer, but the gag made it impossible for him to speak correctly.

Before he could mumble his complaint, he heard an ominous buzz and screamed in agony. The device between his legs was a cattle prod which sent shocks through his cage and stunned his poor cock and balls. Hugh Jazz acted as though nothing had happened and began asking the bound blond his second question, “What was the term used to refer to male prostitutes in 17th century England, who often catered to wealthy aristocrats and were known for engaging in BDSM activities?”

Brett knew this answer as well. A timer began ticking down from twenty seconds, and the gagged man took his time. He just needed to be slow and steady in his answers. “Mhhhrrry Hhhhoussses,” he said through his gag.

“Ohh, another close answer,” Brett’s heart sank. They had rigged this round against him. “You answered Murry Houses. However, the correct answer was Molly Houses.” The bound man started tugging at his bonds wildly. He knew what was coming and cried out in agony as the cattle prod struck his cage again, subjecting his sexual organs to another round of pain.

The crowd appeared to enjoy his torment, but Hugh Jazz simply continued the round. “Question Three: What is the name of the Japanese rope bondage technique that originated in the 1600s?”

Despite their sexual tone, Brett found these questions incredibly easy, but he knew the game was rigged against him. Nonetheless, he tried to break his answer down. “Shhhhiiiii Bahhh Eeeee!”

He was convinced he had beaten the system this time, but his pretty eyes widened when he heard the announcer’s voice. “Incorrect again. You answered Shii Bah Eee, but the correct answer was Shibari. It is all one word.”

Brett shook his pigtailed head in disbelief and cried out when the cattle prod delivered his latest round of punishments. Brett had no idea how, but he knew he would destroy that announcer if he ever got the chance.

The announcer continued, “With three incorrect answers, you must answer every question correctly to win the round.” Hugh was mocking him. “Question four: What was the name of the famous courtesan who was the mistress of King Louis XV of France?”

The timer ticked, and Brett had to delve deep into his knowledge bank to retrieve the answer. His heart sank when it became clear he could not coherently enunciate the correct answer. Nonetheless, he tried, “Adamm De Poopador.”

“Ohhh, you were so close there,” Hugh teased even further. “You answered Adam De Poopador. The answer was Madame de Pompadour. I was really rooting for you there.”

Brett glared up at the ominous voice surrounding the room. He prepared himself for further pain, but it never arrived. Instead, his chair disappeared, leaving him unbound on the floor as the room morphed into the mirrored transformation room.

The unwilling contestant stood up. “Unfortunately, Brett lost the double jeopardy round. That means the next body part will be feminized and encased in bondage.” Brett shuddered. “His next body part is…” The helpless man closed his eyes. They were running out of body parts to tamper with, but his heart sank when his worst nightmare became a reality “….penis!”

The crowd roared with glee, and Brett heard a thud of an object hitting the floor. His penis cage had suddenly detached from his confined member. “You won’t be needing that anymore,” Hugh Jazz teased him. Brett felt a warmth in his groin and stared horrifically in the mirror as the length of his freshly freed penis began to recede. He tried to look past his giant breasts but couldn’t lean forward enough, so he stared numbingly at the mirror before him.

Brett attempted to grab his pussy and halt the shrinkage, but the magic paid no mind to him. His previously impressive member got ever smaller until his groin resembled the front of a Ken doll. His torment wasn’t over, however, as the tingling in his groin intensified and began to form a slit. His internal sexual organs readjusted until his previous manhood was replaced with a fully functioning pussy.

The feminized man didn’t dare touch his new feminine body parts, and he suddenly found himself unable to. He yelped out in his high-pitched bimbo squeal, feeling a phallic-shaped metal object slide into his newly formed pussy. It pushed itself ever further until a metal belt wrapped itself around his hips and connected to a face plate covering the shaft inside of him. Two sturdy silver padlocks attached themselves to his belt, ensuring the new chastity belt was secure.

“What an excellent turn of events,” Brett stared in dumbfounded shock while his teasing host explained to the audience. “Our delightful contestant has found himself with a brand new vagina. As much as he would love to play with it, the second part of the forfeit ensured his pussy is locked away as effectively as his cock used to be.” The audience cheered. “Of course, there is plenty of fun he could still have with his new sexual organ.” Brett cried out and collapsed to his knees. The metal dildo inside his newly formed pussy began vibrating ever briefly. He had never felt such an intense, sudden sensation before, and the pulsing dildo brought him to his knees.

“However, as Mr Norris lost his challenge, the audience will select a bonus forfeit.” Brett’s eyes widened. Hadn’t they done enough to him already? They removed his damn manhood, for heaven’s sake. There was a pause before Hugh declared the results. “This one is always an audience favorite. Our lovely contestant will find himself decorated with some lovely new tattoos.”

“Aghhhh oohhh!” Brett screamed. He had always believed tattoos and piercings were unbecoming of anyone who wanted to be taken seriously. He worked in a professional environment and never thought to hire a man or woman who subjected themselves to becoming somebody else’s canvas.

His skin pricked and tickled all over his body. He stepped closer to the mirrored wall, helplessly watching various pieces of lewd and feminine artwork appear on his body. A pink and yellow butterfly appeared on his upper right arm, a small Playboy bunny tattoo displayed on his left ankle, and a pair of plump red lips appeared on his collarbone, with red-inked words ‘Kiss Me’ displayed underneath them. However, the artwork wasn’t complete, with more pieces covering his body with each passing moment. A black tribal tattoo appeared on his lower back just below his corset, with the word ‘BIMBO’ written in cursive pink font underneath. A silhouette of a woman straddling a stripper pole adorned the length of his right leg, and a winged heart tattoo was positioned directly above his brand-new pussy. Finally, the back of his shoulder displayed the text ‘Treat Me Like A Princess, Treat Me Like A Whore’ in cursive font, with the word princess crossed out and replaced with ‘Bimbo’ directly above it. He looked like some whore desperate for attention.

He stared at his former temple in humiliation. How had they managed to reduce his body to this embarrassing state? He wasn’t given much time to process his new discoveries before the room transformed again.

❖

“We’ve just got three rounds remaining before the ultimate assault course finale. So far, our contestant has won three challenges and lost four.” Hugh Jazz recapped the events to the invisible audience while Brett took in his new predicament.

The room had reformed into a large, empty, airy gym. Brett stood on a treadmill in the center of the room, with his wrists again cuffed. This time, he found his arms bound behind his back and connected to a chair dangling from the ceiling, ensuring he couldn’t escape whatever challenge awaited him.

“We are now moving on to the fitness challenge!” the host declared excitedly. The rules are straightforward. Mr Norris is standing on a manual treadmill. As soon as he starts running, the track will move beneath him. He has thirty minutes to run three miles. If he fails to reach the three-mile mark within the allotted time, he will fail the challenge.”

Brett knew the challenge wouldn’t be as easy as Hugh explained, but he was extremely fit and knew he could run three miles in under twenty minutes. He felt strangely confident with his chances. A beep signaled the start of the round, and a display appeared on the treadmill, showing him how far he had traveled and how long he had left.

He started jogging and immediately discovered how much more difficult this challenge would be with his newly transformed body. His heaving, huge chest pulled him forward, bouncing gently with each step forward. The metal dildo inside his new, sensitive pussy writhed around, unintentionally stimulating him as he traveled.

He completed a mile in just over seven minutes, but everything changed once he reached that mile mark. The metal object trapped inside his pussy began lightly vibrating, causing a constant arousal to build inside his transformed body. Brett knew there would be tricks, but he wasn’t prepared for the alien sensations running through his body as his bare vagina was pleasured.

He tried to ignore the weight of his new chest, the pleasure building inside his body, and his new hoop earrings crashing against the side of his neck. He managed to reach the two-mile mark after 19 minutes. “Anghhh!” his gagged mouth cried out. The dildo inside him intensified, buzzing uncontrollably inside his pussy. His knees almost gave way due to the shocking pleasure he was forced to endure.

Sweat dripped from his face, and his mouth was visibly panting. He tried to ignore the distractions and soldier on, but the further he neared the finish line, the more weightless his legs felt beneath him. With only one minute remaining, Brett thought he had wasted his opportunity. Still, he closed his eyes and pushed past the pain and pleasure.

“Wow, what a round that was!” The announcer confirmed. The feminized contestant was terrified of the outcome but slowly peeled his eyes open to reveal his fate. His eyes widened in surprise when he found he had reached the three-mile mark with just two seconds remaining. He gasped a sigh of relief. His wrists unshackled, and the gym disappeared around him, placing him back inside the mirrored room.

“Congratulations, Brett, you have won challenge eight. The body part you have agency over is…” Brett groaned beneath his gag. Even after winning a challenge, he still had to subject himself to one form of humiliation or another. How was this fair? “…arms & legs!”

Brett groaned in bemusement. He spent hours at the gym and was proud of his well-built muscles. The idea of feminizing himself and losing everything he worked so hard to accomplish terrified him. However, the alternative solution of subjecting them to bondage was out of the question. If he allowed his limbs to be bound, his chances of completing the assault course were next to impossible. Reluctantly, he pointed at the large feminization display before him.

Brett felt a familiar tingling sensation surround his limbs. As his arms and legs shifted and changed, the once bulky muscles that filled them began to soften and shrink. Once defined and dominating, his biceps and triceps became slender and delicate, the veins and contours disappearing beneath smooth skin that seemed to glow with gentle femininity. The muscles he was previously so proud of had dissipated and been replaced by the slim feminine figure he now horrifically saw in the mirror.

The tattoos on his arms and legs appeared to adjust, conforming to their smaller canvas. However, according to the man who wore them, they still looked as tacky and tasteless as ever. “Unghh!” He whimpered in defeat, his high-pitched voice matching the feminine bimbo appearance he sported.

However, his torment wasn’t complete. His fingers began to numb. He brought his hands to his face just in time to watch his fingernails lengthen before his very eyes, protruding 2 inches from the edge of his fingertips. They pointed off into a stiletto shape before each finger was painted a bright and undeniably bimbo-like candy pink. A similar sensation on his toes informed the busty contestant that his toenails now sported the same feminine shade.

His nails looked extremely feminine and dangerous. Before he could utter any further incoherent protests, his surroundings morphed again.

❖

Brett became disoriented as carnival music blared around him. When the room completed its transfiguration, the feminized man suddenly felt incredibly self-conscious. The magical room had placed him outside on a field surrounded by various carnival games. There was no one around, but the idea of being outside in a public place looking like this horrified him.

Most games were blurry recreations of typical carnival games, but one stood out clearly. The pigtailed blond tentatively approached the stand and gasped at what he saw. “Welcome to Round Nine, the infamous ring gag cock toss!” He shuddered when his pretty blue eyes rested on the realistic plastic dildos surrounding the carnival game. “The game is simple. Ten of these tasty rubber cocks will be launched in the air, and our contestant must attempt to catch them in his pretty gagged mouth.” Brett’s shuddered; they couldn’t be serious, could they?

“All Brett needs to do is catch five out of the ten dildos to win the challenge and decide his own fate.” All he needed to do? Brett narrowed his eyes in fury. “Are you ready?” As usual, no one waited for his confirmation before a beep signaled the start of the contest.

Brett wasn’t sure exactly what he needed to do until he witnessed a mini cannon hurl a 6” flesh-colored dildo into the air. On instinct, Brett immediately positioned himself under the flying cock and caught the sex toy between his gagged teeth. His eyes widened, and his throat gagged when the cock slid into his throat without warning.

The dildo magically disappeared, and the scoreboard above the carnival display ticked up by one. Without any time to recover, a second, slightly larger cock flew into the air. He raced underneath the toy and caught the second in the same fashion. He was prepared this time and suppressed the gag when the dildo slid further down his waiting throat.

He continued attempting to catch the horrific rubber toys in his mouth, and after eight attempts, he grabbed his fourth dildo. “This is impressive from our determined contestant. He only needs one more successful catch to win the ninth round.” Hugh Jazz encourages him over the sound system. Another dildo shot from the cannon and flew in the air toward Brett’s gagged mouth. As it hurled closer, Brett’s eyes widened. The dildo looked huge. Nonetheless, he placed his head perfectly underneath the approaching toy until the dildo bounced off the rim of his ring gag and fell away.

“Aghhhh!” Brett screamed out with his bimbo tone. He had been cheated. He placed himself perfectly underneath the toy, but it was too thick to fit between his locked ring gag. The final cock shot from the cannon and headed towards the frustrated sales manager. This cock was even wider than the previous toy and bounced off his plastic ring again. Brett had lost.

“Ohhh, tough luck there,” Hugh consoled the defeated contestant. When Brett started hurling angry, incoherent insults at the commentator, Hugh Jazz laughed. “We are in a carnival. No one said carnivals played fair,” he taunted before the outdoor funfair facade disappeared and morphed back into the familiar mirrored transformation room.

“You all know the score. You will choose Brett’s fate here, and his next body part is…” After an agonizingly long wait, Hugh finally revealed the wheel’s choice. “…face.” Brett’s head dropped in defeat. “Now, with those cute ears, bright blue eyes, and juicy big bimbo lips, there isn’t much work left to put into Brett’s face. Perhaps you would prefer to route for the bondage option instead.” Hugh announced cheerfully.

“Ohh, I guess you don’t like taking my advice,” The host said to the audience once they had voted. “The audience has chosen to complete the feminization of Mr Norris’ face.”

Brett closed his eyes, sensing the dreaded pinpricks assault his face. He felt the tickling sensations concentrate on his cheeks and jawline, as well as focusing around his eyes and lips. The entire process took about thirty seconds before the sensations died away. “Well, doesn’t our fantastic contestant look like a pretty picture?” Despite his reluctance, the host’s words prompted Brett to reopen his eyes, and what he saw caused a shudder down his spine.

He barely recognized himself anymore. His facial features had been softened and smoothed over. His five o’clock shadow had disappeared entirely, and his naturally well-defined jawline had rounded off. His cheeks appeared high on his face, and any natural wrinkles he previously had had disappeared. His eyes were now cartoon-like. They were still the wide, dazzling blue eyes they had been before, but they gave a vapid, permanently surprised expression no matter how much he attempted to look furious or fierce. Matched with the thinly drawn eyebrows and lengthy dark eyelashes, he looked like the definition of a bimbo. His nose had shrunk into a cute button nose, and even his lips had been given a plumper appearance.

He thought the horror had temporarily subsided until he felt the pinpricks reappear on his face. He pleaded incoherently, staring at his new-looking lips. “Ahh, our contestant is already discovering the effects of his bonus forfeit,” Hugh commented. Brett’s lips had transformed into a bright pink shade, matching the color on his fingernails. A mixture of pinks and blacks decorated his animated eyes, completing a sultry cat-eyed look. His eyelashes appeared darker, and a soft pink colored his newly high-positioned cheekbones. “Our audiences have selected the beautification perk. That new makeup of yours is completely permanent, so you can suck as many cocks as you like without worrying about running makeup, but that’s not all,” he continued to tease. Brett felt a shudder run throughout his body as every single hair below his eyebrows disintegrated before his very eyes. The result meant his entire body looked incredibly smooth and feminine. “You don’t have to worry about shaving any longer. Some people would kill to have perfect skin like yours.” Brett wanted to kill the host and was even more furious when his facial expression betrayed the anger he felt.

“Don’t worry, our pretty little bimbo; the game is almost complete.” Hugh Jazz said in a softer tone, “It’s time for the final round!”

❖

“Aghhh ughhhh!” Brett cried out in concern. The transformation room morphed in a flash, and the busty blond sales manager found himself inside an office environment that looked much like the Kink Coutures offices Brett worked in himself. More alarmingly, the gagged contestant was strapped to an office chair. His bare, naked legs were held together by leather straps around his ankles and thighs. His corseted waist was equally bound, and straps wrapped above and below his enhanced chest. As he sat on the chair, the chastity belt pushed the metal dildo further inside Brett’s brand-new pussy.

He was seated at an incredibly bare workstation, with nothing but a bright pink basic PC monitor and keyboard lying on top. “Ladies and gentlemen, we have made it to the final ro…” Suddenly, a siren filled the room, and the faceless audience cheered. “Well, well, well. Our final round has brought double jeopardy with it.” Brett’s heart sank, considering how poorly he fared in the previous two double jeopardy rounds. “However, there is a slight twist. If you succeed in the following task, not only will you move on to the final assault court unscathed, but you can choose a previous transformation to undo completely.” The crowd booed at the prospect of Brett reversing any of his feminine alterations. Still, that stipulation perked up the pigtailed contestant.

“On to the challenge,” Hugh Jazz began. “Our lovely contestant is seated in front of a word processor. The sales manager works inside an office, so his typing skills must be a joy to behold. Mr Norris has five minutes to copy 200 words. Every spelling error will result in a five-second penalty.” The host explained to the audience. “Now, if you are ready, let’s begin.”

Brett was confident in completing his task before he stared down at his hands and remembered the long, bright pink talons on his fingers. Without any time to react, a beep signaled the start of the round. He starts carefully copying the text on the screen, shuddering at the humiliating statements he was forced to repeat.

‘I am a dumb bimbo.’

‘I need a man to take care of me.’

‘I’m only happy with a cock in my mouth.’

‘I’m too dumb for a real job.’

The blond contestant was compelled to repeat the horrific statements over and over again to have any chance of passing the task. His fingernails made it incredibly difficult to type efficiently, and he had to press the keys directly with his nails to avoid making mistakes.

With forty-five seconds remaining, the feminized man still had twenty words to type. He knew he needed to pick up the pace, but two spelling mistakes in a row made meeting the challenge all the more tougher. He had just three words remaining when his heart sank, and he heard the buzzer signaling the end of the round. He had failed again. “Ohh, just three words to go. So so close,” the host consoled his contestant, although it sounded more like mockery.

The rubber straps securing Brett to the chair vanished, and the office morphed back into the mirrored transformation room. “This could be the last time this season we see this room, unless Brett wins the final challenge and we have to undo all our hard work,” Hugh elicited a chorus of boos from the audience. “Now let’s see what final body part we are transforming.”

Brett stood nervously. He was beyond furious with how the day turned out, although as he was forced to stare at himself in the mirror, the vapid, gagged bimbo staring back at him showed no sign of anger at all. “Well, well, well. The wheel hasn’t chosen a body part at all. Looks like you’ll finally be covering up. We will be transforming your outfit.”

Brett felt a brief moment of relief at the prospect of covering up his new feminized body, but the consolation soon passed after his new outfit began forming on his curvy body.

Pink latex began encasing his torso and wrapping around his corseted body. It started forming a tight-fitted rubber dress, reaching his mid-thigh, covering his chastity belt and corset. Alarmingly, the dress didn’t cover his huge fake tits but rather wrapped themselves around them to form a keyhole window. The pressure of the latex material wrapped around the base of his breasts helped push them out even further. The dress slid around his neck and formed a halter opening, leaving his arms uncovered. A white zip formed at the bottom hem of the dress, both in the front and back, allowing someone to zip the dress up a few inches and gain access to his chastity-clad pussy and ass.

Brett felt a firm material wrap around his neck, and a white leather posture collar materialized before his very eyes. After the straps behind him tightly buckled and were fastened with tiny padlocks, the feminized man found it impossible to tilt his head down. He could only look below himself if he bent over at the waist. This must have been the bondage element of the outfit, Brett thought.

If he believed the posture collar was the only bondage element to his new outfit, it didn’t take long for him to discover how wrong he was. An invisible force pushed his feminine arms behind him, and a white leather armbinder slid over his arms, with the straps nestling between his exposed fake tits. He tried in vain to struggle against the confining arm prison, but the laces of the binder tightened with each passing moment, and he eventually found his arms completely trapped and immobile.

“Aghhhh aggggg!” Brett murmured under the gag. He was tricked. He had feminized his arms and legs because he didn’t want them hindered during his final challenge, and now he found them bound anyway. The same fate soon followed his legs as his bare pink toenailed feet were forced onto their tiptoes. White leather materialized around each foot, forming two tall knee-length ballet boots with extremely tall stiletto heels. Each boot was fastened with several straps, and a tiny padlock accompanies each buckle. To add to his misery, a short metal hobble chain connected to both shoes made it impossible for the helpless contestant to take large strides.

He hissed through his gag when he felt a sharp sting on both of his nipples. He tried to stare down but was reminded of his severe collar restricting his movement. As we watched himself in the mirror, he noticed two barbell piercings had inserted themselves in his erect nipple and connected to each other with a small silver chain. The chains merged in the middle and floated toward a D-ring at the center of his posture collar, clipping onto it. Brett could helplessly feel the tug against his newly pierced nipples as the chains pulled taut.

“Ummnggg!” He squealed out. His final humiliating addition to his new outfit materialized inside his ass. A rubber buttplug filled up inside him, expanding in length and width until it couldn’t expand any further. His latex dress covered the plug, but anyone who unzipped the hem would be greeted with a pink jeweled butt plug inside him.

“Wow, don’t you look like a precious treat,” the host mocked him. “I’d say you are almost ready for the final assault course challenge. Almost…” Brett hated the taunting laughter of the crowd. He had no idea what the perverted presenter meant by his statement, but he wasn’t made to wait long to find out. The entire room appeared to grow larger around him, but Brett’s intelligent mind told him it wasn’t the room transforming; it was him. “Of course, you have a bonus forfeit for failing your last task, and the audience has decided that your new heels give you too much height. Your impressive 6’2 stature has now transformed into a pint-sized 5’2. Don’t worry; your 9” heels make up for most of that.” Brett writhed in fury, but his struggles almost caused him to stumble on his ass.

“Now you’re ready for the final challenge,” Hugh Jazz declared before the transformation room changed around him one last time.

❖

Brett shuddered in fear as he stared around the transformed room. The space reminded him of a multicolored children’s indoor jungle gym. Bright blues, pinks, yellows, and greens assaulted his eyes, with a large soft plastic ‘play’ area in the middle. He soon discovered this play area was his final challenge, and it was definitely not designed for children.

“Congratulations, Brett Norris. You have made it to the final assault course challenge at the season finale of Bound Ambition!” A raucous cheer was heard around the edges of the room. Unlike his previous trials, he could distinguish the dark silhouettes of the audience around the perimeter of the colorful room. However, Brett didn’t feel particularly cheery for making it this far.

“Before we begin, let’s go over the simple rules.” Hugh explained, “Once the timer starts, you will have ten minutes to navigate your way through the assault course and find your way out on the other side.” Brett groaned through his gag; he would have felt far more confident completing this challenge ten minutes ago. “If you successfully complete the challenge, every single alteration made to your body will be reversed, and you will be the sole winner of a $500,000 cash prize!” The crowd cheered again, although not as fervent this time, indicating that this was not their preferred option. “However, if you fail to make it out in time, your alterations will remain, and you will be delivered to your sponsor.” The audience cheered even louder at this potential outcome. Wait, Brett thought. Who was his sponsor? The host mentioned a sponsor after his first challenge, but the feminized man never thought much about it. Someone had actually set this up on purpose.

“With the rules wrapped up, I know our pretty little bimbo is chomping at the bit to get started. Or, at least chomping at the ring gag,” his joke elicited laughter from the audience. Brett had no time to decipher who had set him up, and a series of beeps brought him to the present. The sales manager knew that failure was not an option and was determined to do whatever was necessary to complete the course, no matter how humiliating. One final beep indicated the start of the final round.

Brett immediately ran toward the assault course entrance, momentarily forgetting about the hobble chain connecting his boots. He stumbled forward, and with his arms pinned behind his back, he fell on his face. He immediately attempted to rise to his feet. Still, the combination of his extreme heels and the armbinder made it impossible. Instead, he traveled towards the entrance on his knees, shuffling as fast as possible. He groaned when he finally reached his target.

There was a closed barrier with a notice above it stating, ‘Suck your way to an open door.’ Three rubber dildos were attached to the wall beside the door, each increasing in length. A dimmed green light was positioned above each phallus. He focused on the smaller 6” dildo and wasted no time pushing his gagged lips around the shaft. Brett opened his throat and forced the dildo inside, pressing his cute button nose against the pressure pad, immediately lighting up the green light. He moved over to the 8” cock and slipped it between his lips. His eyes filled with water, with the feminized man desperately trying to suppress his gag reflex. Eventually, his nose hit the pad, and a second green light appeared. He kneeled over to the final 10” black rubber cock. Taking a deep breath, the pigtailed man slowly eased the cock further down his throat. He struggled to take the final inch but lunged forward and pressed his nose against the pressure pad. The third light beamed, and the barrier preventing him from entering the assault course opened up.

He shuffled his way through the open passageway and found himself at the entrance of a narrow passageway. “Unghhh!” he squealed in his bimbo-styled voice when an invisible force lifted the bound beauty and placed him back on his ballet-heeled feet.

“Aghhh,” the platinum-blond contestant squealed. As he tentatively made his way through the confined corridor, he felt a harsh smack on his already tender, plugged ass. He took several more careful, hurried steps and felt a second smack on his rear. As he worked his way through the corridor, a leather paddle slapped his ass at regular intervals, with each spank harsher than the last. Brett had nowhere to hide to avoid the impact, and he just needed to soldier on, tottering on his tiptoes until he reached the end of the passageway.

Before he could escape into the next section, there was a plastic mound approximately 3 feet high he needed to climb over. Without the use of his arms, the helpless blond attempted to jump over the rounded mound. He failed on his first attempt, and his second. He tried to run at the barrier to give himself a running start, but the hobble chain tripped him over. He leaned against the plastic mound blocking his path to prop himself up. Trying a new technique, he jumped backward and wriggled his trapped arms to create a little friction. This action allowed him to edge himself upwards until he reached the apex of the barrier, and he slid down the other side. Brett landed on his back and glared up at the audience as they laughed at the indignant manner of his fall.

He stared up at the large timer hovering above him. He had no idea how long this course was, but he had already used up almost five minutes. Looking ahead to his next challenge, he found himself in yet another narrow corridor. However, a waist-height horizontal bar ran across the length of the passageway. It was clear that Brett needed to straddle the pole if he wanted to traverse the corridor.

He tottered carefully over to the pole and positioned his crotch over the top. He needed to stretch slightly to slide into position, creating an uncomfortable situation where his tiptoes struggled to reach the floor. He soldiered on and gently slid against the pole. He gasped sharply. As he slid, the pole began to vibrate. His chastity belt pressed up against the metal post and pulsated in rhythm to the vibrations, prompting the metal dildo inside the helpless blond man to resonate inside him.

“Unghhh,” he spat out. The pleasure built up inside him as he attempted to ignore the forced pleasurable sensations and navigate toward the end of the corridor. With a little less than half of the post left to cross, the building pleasure was too much to ignore, and the feminized man fell victim to his first pussy induced orgasm. Wave after wave of overwhelming pleasure assaulted every cell in his body, and drool began flowing from his gagged lips. The orgasm lasted about 30 seconds but felt like a whole lot longer, and he attempted to continue his task.

A second orgasm approached until Brett managed to slide off the post on the other side, with his knees weakening and giving way. He took a moment to recover, but staring up at the clock and discovering he only had two minutes remaining, he used the side of the passageway to pull himself back up.

He pushed through the remaining steps of the corridor and suddenly found himself in a large space. A door on the other side of the space was labeled in large letters ‘EXIT’, and the restricted blond tottered over as quickly as he could. He used his bound arms to turn the door handle but soon discovered the exit was locked.

Staring around the room, he discovered a silver key hanging in the center. He wobbled carefully over to the key and realized the only way he could grab it was with his pried-open mouth. Attempting to trap the elusive key between his tongue and teeth, he made several attempts to tug it from the suspended string.

Finally, Brett managed to tug the key free, but his tongue slipped before he could totter back to the door, and the key to his freedom crashed to the floor. He dropped down on his knees, and the crowd around him cheered and laughed at the comical sight of the bound, latex-clad bimbo attempting to pick the key up from the floor. With his rubber-covered ass high in the air, he succeeded in picking up the key, but his heart sank when he suddenly heard an ominous buzzer sound around the room.

“Ohhh, our contestant was so close to earning his freedom,” Brett shuddered when the host returned over the PA system. “His actions were heroic, and he was just a dozen steps away from returning to his old life.” The audience cheered as Brett panted helplessly through the ring between his teeth.

“That’s the end of the show and the end of the series,” Hugh Jazz’s announcement prompted a chorus of boos from the audience who wanted to see more. “However, be sure to join us next season when we drop in on Brett and see how he has adjusted to his new life.” New life? He surely can’t be serious, Brett thought helplessly. “Thank you for watching Bound Ambition. We will see you again next season.” Brett heard a strange music number start to play until the environment around him dissipated, and he found himself in the sterile white room he woke up in when his journey began.

A door opened, and Hugh Jazz approached the helplessly feminized and bound man. Brett narrowed his dopey, dazzling blue eyes and lunged towards the sadistic host. Not for the first time, Brett forgot about the hobble chain and crashed forward onto his exposed, chained fake breasts. As the defeated man looked up, Hugh was grinning down at him. “You were a true sport. I owed your sponsor a favor, and I think you will make the payment nicely.” Brett pleaded unintelligibly, but the suited man simply chuckled. “Don’t worry, you’ll get used to your new life eventually.” He crouched down and cupped the bound bimbo’s soft chin, “Are you ready?” He asked. Without waiting for a response, the magical man clicked his fingers, and Brett witnessed the environment turn to darkness around him before he lost consciousness.

❖

Three Months Later

The sales floor of the Kink Couture head office building was buzzing with excitement as Chris Freeman was recently announced as the new Director of Sales. Rumors had circulated that the previous sales director took a vacation to Tahiti and never returned. Chris perhaps was the better choice all along, and despite the former Director’s popularity, the announcement was well received.

Chris accepted handshakes from his new subordinates, and the lanky brunette slowly made his way back towards his new corner office. As he placed a hand on the door, the CEO, Ronald Hannity, rested a hand on the man’s shoulder. “Congratulations, Chris. You earned this.”

“Thank you very much, Mr Hannity,” Chris beamed back. “I wasn’t sure if I was ready for the extra responsibility, but after taking some time, I am excited to get started.” He opened his new office door, and the Chief Executive followed him inside.

The overweight boss had been in this office a thousand times before, which largely remained how he remembered it. However, one freshly unique feature caught his eye. Nestled between the sizeable overarching bookcase, a glass display case was presented as a life-sized Barbie doll box. The front exterior of the case displayed the words ‘Bondage Bimbo’ in Barbie font, and the contents of the box certainly lived up to that moniker.

A doll was presented on a slowly spinning turntable, displaying every inch of her exaggerated body. Her long platinum blond hair was tied up in tall schoolgirl-esque pigtails. Her dazzling blue eyes widened further than any human would ordinarily be capable of, displaying a cartoonish, surprised expression. She has a cute button nose and soft, high cheekbones. Her huge lips dominated her face. They were bright pink and protruded out from her bimbo face. They formed an O shape, enforced by the wide plastic ring gag wedged between her teeth.

The CEO admired her ridiculously huge H-cup breasts. They were held high on her chest by the keyholes inside the confining latex dress she wore. Her nipples were tattooed bright pink, and barbell piercings connected a chain to a strict white posture collar around her neck. The latex dress showed off the bimbo’s impossibly slim waist and enhanced her perfect hourglass figure. The doll was unable to cover her body with her arms as they were forced behind her back, imprisoned by a white leather armbinder, forcing her shoulders back and thrusting her huge tits out even further.

Ronald enjoyed spying on the tattoos that decorated her body. The cursive font ‘Treat me like a bimbo, fuck me like a whore’ proudly displayed on her exposed shoulder was a particularly nice touch. The heavily made-up bimbo stood on her extreme tiptoes, enforced by the white ballet boots locked on her feet.

She was the perfect example of an extreme bound bimbo, and the very sight of her stirred something in his pants. The CEO marveled at how lifelike the doll appeared despite her cartoonishly large eyes and her impossibly enhanced breasts.

“That’s an interesting display you have here,” He finally spoke up as Chris stepped next to him, admiring the view himself.

“Ohh, yes,” the new Sales Director grinned. “This display reminds me to never take anything for granted.”

The Chief Executive raised an eyebrow. He wondered how such a caricature of sexuality would remind Chris of that. He chuckled before patting the tall man on the shoulder. “Well, it’s impressive nonetheless.” Ronald surmised. “Congratulations on your promotion, and keep up the good work.” Chris smiled and nodded, and the wideset CEO left the Director alone in his new office. Well, not entirely alone.

Chris flicked a switch attached to the side of the glass display, and the soundproofing disappeared. “Unghh ummpphh aghhh!” He heard the constant high-pitched whinings of the bound bimbo displayed before him. Brett desperately tried to get the CEO’s attention. Still, the soundproofed display muted his complaints, and any movement from him prompted an excruciating shock inside his new pussy.

Chris folded his arms and admired his prize, displaying herself inside the glass case. “I don’t understand what you’re saying,” he taunted his former rival. “Are you hungry?” He asked. “I would love to feed you again, but I need a little time to recover.” He chuckled, patting his pants. Brett shuddered; his diet consisted solely of Chris’ cum from now on.

“I would love to chat, but I have some important meetings to schedule and can’t have your bimbo moans interrupting me.” He flicked the switch again, and the gagged moans disappeared in an instant. “I’m sure you can find a way to entertain yourself, however.” The new Sales manager grinned before pressing a green button on the display case.

He witnessed his bound former rival’s big, wide eyes expand further. The metal dildo and rubber plug inside his orifices began vibrating in unison. As they delivered pleasure to the helpless bimbo, Brett tried desperately to stay frozen in place. Any movement would turn those vibrations of pleasure into unbearable pain. Chris bit his lower lip and smiled contently. He headed to his large oak desk and left the busty bimbo to experience her new fate.