Robert had spent years slogging away at a corporate job that left him feeling stuck. His daily routine was monotonous, and despite a few promotions, he felt unfulfilled. He didn’t have many close friends, his hobbies were non-existent, and his dating life was practically nonexistent—people often described him as dull. Robert knew he needed a change.

He dreamed of a place where the sun was always shining, life moved at a slower, more affordable pace, and there was a chance for something new and exciting. Thailand seemed like the perfect escape. One day, on impulse, Robert quit his job, sold his house, and packed up his belongings into a few suitcases. Without looking back, he boarded a one-way flight to Thailand, eager to leave his old life behind and embrace something different.

As Robert stepped off the plane, the warmth of the sun felt like a welcome embrace, and a smile spread across his face. The tropical heat and the friendly glances from the locals made him feel instantly at home. It was clear that this was going to be a new chapter in his life, far removed from the routine he left behind.

Back home, Robert was always the nice guy, the one who seemed to blend into the background and never quite caught a woman’s eye. But Thailand was a different story. Here, everything had changed. Eager to embrace his newfound freedom, Robert splurged on a luxurious villa just outside Bangkok. For the first few days, he revelled in the sun, lounging by the pool and letting the warm rays soothe his body and spirit.

With a mix of curiosity and excitement, Robert dove into local dating apps, quickly finding himself caught up in a whirlwind of passion. He soon met a stunning Thai woman who seemed to embody every fantasy he’d ever had. He knew how to play the game—telling her he was interested in a serious relationship to win her trust and get her into bed. Her touch, her kiss, and the way she moved drove him wild, sparking a night of intense pleasure that left both of them breathless.

This became Robert’s nightly routine. Each evening, he indulged in the company of beautiful Thai women, making them believe he was looking for something meaningful, only to enjoy the thrill of their encounters. If he couldn’t connect with someone online, he’d simply pay for a night of steamy, exotic pleasure. Sometimes, he’d bed several women in a single day, feeling like he was finally making up for lost time and living the vibrant, exciting life he had always dreamed of.

He woke up one morning and decided he would go to the beach. He was eager to catch some waves and work on his tan, ready for whatever new adventures awaited him.

Emerging from the waves he pushed his long sandy hair behind his ears before he spotted an incredible Thai woman sunbathing in a red swimsuit. She had flawless bronze skin and large firm breasts. Her beauty was captivating—long, silky black hair cascading down her back and a figure that seemed to defy gravity. There was something about her that he couldn’t put his finger on..

Having gained some confidence over the past few weeks from his encounters with various Thai women, Robert approached her. He felt a jolt of excitement and a noticeable bulge in his pants as he approached her. He had to know her name.

“Hi there,” Robert began, his voice slightly shaky but laced with hopeful anticipation. “What’s your name?”

She barely glanced his way, her eyes rolling as if he were just another annoying tourist. Undeterred, Robert tried a few more lines, clumsily attempting to charm her, but she continued to brush him off with dismissive glances.

Finally, with a sigh of impatience, she turned her head slightly, peering at him through her dark sunglasses. “Thida,” she said curtly, before adding, “But you’re not my type.”

Robert’s heart sank at her words, but something about Thida intrigued him—something he couldn’t quite pinpoint. She radiated a confident, alluring presence that set his pulse racing and made his desire intensify. She was different from any other Thai woman he’d met, with an air of mystery and command that was impossible to ignore.

Determined not to let this chance slip away, he pressed on, his voice filled with earnestness. “Maybe we could still go on a date? I’d like to get to know you better.”

Thida adjusted her sunglasses, clearly ready to end the conversation as she prepared to put in her earbuds. Just as she was about to tune him out, Robert blurted out, “Is there anything I could do to earn a date with you?”

She paused, sitting up in her sun lounger and giving him her full attention. Her eyes locked onto his, and a wicked smirk played on her lips. “Massage my feet,” she commanded, her tone brooking no argument. “And then put my shoes on for me. If you do a good job, I might consider going on a date with you.”

Robert was momentarily stunned by her boldness. He hesitated, unsure if she was serious, but the challenge in her raised eyebrow was clear. Feeling a surge of both embarrassment and undeniable arousal, he dropped to his knees beside her lounger. His hands trembled slightly as he began to massage her delicate feet, his fingers working to knead the soft flesh.

As he touched her, he could feel the heat rising in his cheeks, and a growing pressure in his pants that he couldn’t ignore. The public humiliation of his position drew giggles and whispers from passersby, some even snapping photos. Each soft stroke of his hands against her skin only intensified his arousal.

“Enough,” Thida said, her voice smooth and commanding. She pointed at her shoes, and Robert, still flushed with desire, picked them up. He carefully placed the first shoe on her left foot, fumbling with the laces as he tried to ignore the laughter and comments around him. The dominance she exerted over him was both humiliating and thrilling, making him feel both vulnerable and excited.

He quickly moved on to the second shoe, his hands working with increasing urgency as he felt her intense gaze. Once he finished, Thida stood up with a graceful motion, adjusting her bag over her shoulder. Her unreadable expression as she looked down at him only heightened his anticipation.

“Give me your number,” she commanded.

Robert scrambled to take the pen and paper, hastily scribbling down his number. Thida took it from him without a word, then turned and walked away, leaving Robert kneeling by the lounger. His heart pounded in his chest, his mind racing with thoughts of what might come next, and his body still tingling from the encounter.

Rather than seeking out another Thai woman for the night, Robert found himself masturbating to the encounter with Thida. There was something about her—something elusive and commanding—that set her apart from anyone else he’d met. That night, he replayed their interaction over and over in his mind, his fantasies charged with the memory of her presence.

A week later, just as he was starting to think he’d never hear from her again, his phone buzzed with a message from a private number. His heart raced as her name appeared on the screen.

“Be at the Bamboo Bliss bar at 8 p.m. tonight if you want to talk to me. – Thida”

Robert could hardly contain his excitement. He dressed in his sharpest outfit, determined to make the best impression. Arriving at the bar fifteen minutes early, he was anxious not to miss his chance.

When Thida walked in, she took his breath away. She was a vision in a tight leather outfit that clung to her curves in all the right ways. Her breasts pressed provocatively against the fabric, and her pants accentuated the firm, tight ass that had been haunting his thoughts for days. Robert couldn’t tear his eyes away from her as she approached, her ruby-red lips glistening with a promise of seduction. Her commanding presence made his pulse quicken.

She brushed past him, her heels clicking seductively on the polished floor, turning heads as she made her way through the bar. Every man in the room seemed captivated by the way her hips swayed with each step. Robert followed her, completely entranced by her every movement.

Thida took her seat with effortless grace and fixed him with an expectant gaze. “Get me a SangSom Rum,” she ordered, her tone cool and authoritative, as though he were nothing more than a personal waiter.

For a split second, Robert hesitated, but then he rushed to the bar, his heart pounding. He returned with two drinks, his hands slightly trembling as he handed her the glass. Sitting down across from her, he was spellbound by her confidence and allure. Every detail of her—her breasts, her lips, her flawless skin—captivated him. Robert was lost in her presence, barely able to think straight as he soaked in the intoxicating allure of the woman who had turned his world upside down.

"Tell me about yourself, Robert," Thida purred, her English flawless as she smoothly took control of the conversation, her tone dripping with confidence.

Robert blushed, trying to compose himself under her piercing gaze. He thanked her for meeting him, struggling to sound interesting. But each time he tried to steer the conversation towards her, to unravel the mystery of the woman who had him utterly captivated, she would deftly turn it back on him. It was as if she knew exactly what she was doing, keeping him off-balance, making him reveal more of himself while she remained an enigma.

She had him fetch her drinks, food, anything she desired, testing his willingness to serve her. And Robert—entranced by her dominance, by the way she effortlessly commanded the room—was eager to comply. Every task she set, he fulfilled without question, desperate to prove himself worthy of her attention. The power she held over him was intoxicating, and with each order, his desire for her only grew.

As the hours passed, Robert became more and more intoxicated, the alcohol loosening his tongue, while Thida remained composed and in control, unaffected by the drinks. Finally, she leaned in, her eyes locking onto his with a knowing look. "Why did you want to go on a date with me, Robert? I’m not looking for a one-night stand or a fling with someone."

Robert, already flustered and drunk, stammered out a response, insisting he was looking for a girlfriend, something exclusive. But Thida’s sceptical smile told him she wasn’t buying it.

"I’ve seen men like you come to Thailand for decades," she said, her voice smooth and unwavering. "You sleep around, buy sex, and move on. How do I know you’re not just another one of them?"

Her words struck a nerve. She saw right through him, effortlessly dissecting the life he’d been living since arriving in Thailand. Robert, now feeling the full effects of the alcohol, found himself confessing everything. He admitted to sleeping with several Thai women, even paying for sex, trying to be as honest as possible. But with each slurred word, he knew he was only confirming her suspicions.

Thida leaned back, her gaze never leaving his as she laid down her terms. "If you want to be with. me, you’ll have to be exclusive—committed to me, and only me. You need to prove it, right now, if you ever want to see me again."

Robert, his head spinning and heart pounding, agreed to anything she asked, desperate not to lose her. The night became a blur, and the last thing he remembered was promising to do whatever it took to prove his loyalty and his desire to be committed to her.

When Robert finally awoke, his head was pounding and his mouth felt parched. He stumbled out of bed, gulping down several gulps of water before shuffling into the bathroom. As he sat on the toilet, trying to piece together the events of the night before, he heard a metallic clunk against the porcelain. His eyes widened in shock when he looked down and saw his cock and balls encased in a tight metal contraption—he was locked in a chastity belt.

Panic surged through him as he fumbled with the steel belt, realizing that it was made of unyielding, durable steel. The more he tried to remember, the blurrier his thoughts became. The last thing he clearly remembered was promising Thida that he would do anything to prove he wouldn't cheat on her.

His cock twitched involuntarily, desperate to harden, but the sharp pins inside the metal tube pressed painfully against him, sending waves of intense discomfort through his body. His usual morning routine of masturbation was now impossible, leaving him achingly frustrated.

Just then, his phone buzzed. Robert scrambled to grab it, his heart racing as he saw a message from a private number.

"I hope you enjoyed last night as much as I did. We’ll meet again after you’ve spent a few weeks locked in chastity 😉 - Thida"

The realization hit him like a ton of bricks—Thida had the keys to his chastity belt. He was entirely at her mercy, with no way to contact her or find out when he might be released. The thought of spending weeks like this, his throbbing need trapped inside the unforgiving metal, only heightened his frustration.

Robert's days became a blur of frustration and unfulfilled desire. The tight, relentless metal of the chastity belt was a constant reminder of Thida’s control over him, her power wrapping around him like a vice. Each morning, he woke up with a throbbing cock that went unsatisfied, the sharp pins digging into his flesh whenever he even thought of becoming aroused.

Desperate, Robert returned to the beach where they first met, hoping to catch another glimpse of her. He would sit on the same sun lounger where she had commanded him to kneel, staring out at the water, but she was never there. He wandered the crowded streets, peering into every bar, his heart racing whenever he saw a woman with her commanding presence, but it was never Thida.

Each night, he lay in bed, staring at the ceiling, his cock straining against the metal cage, knowing that only Thida could grant him the release he so desperately craved. And each morning, he woke up with the same hopeless longing, the chastity belt cutting into him as a constant reminder that she was still out there, still in control, and that he was hers—whether he liked it or not.

After two weeks of being locked in chastity, Robert finally received a message from a private number:

“Meet me at the top of Jasmine Blossom Road in an hour if you ever want to experience the sweet release again, cuck boy. 😉”

The message was unmistakably from Thida, and it sent an immediate surge of arousal through Robert. He could feel his cock straining against the confines of the chastity belt as he quickly dressed and rushed out the door, determined not to miss this chance. He was set on demanding the keys from her.

Arriving at the top of Jasmine Blossom Road, Robert paced anxiously. He was there several minutes early, but Thida was nowhere to be seen. Each passing minute seemed to stretch into an eternity. His anticipation turned into agony as he waited, his cock throbbing painfully against the metal cage. Tears of frustration began to swell in his eyes, the unbearable pressure of his unfulfilled desire making him feel as if he might explode.

Just as he felt the first tears escape, he saw her. Thida emerged from the shadows, her presence commanding and irresistible. She walked with a powerful grace, clad in tight leather that clung to her curves, her ample breasts pushed up by the fitted material. Her thigh-high leather boots squeezed her firm thighs provocatively with each step. Every movement she made exuded dominance and control, making Robert's heart race.

As Thida approached, Robert felt a rush of pre-cum leak from his trapped cock. Her smirk was knowing and tantalizing, intensifying the desperate need coursing through him.

"I see you've been waiting for me, cucky," Thida purred, her voice a mix of amusement and cruel pleasure. Her presence only heightened Robert's desperate need.

"Give me the keys now," Robert demanded, trying to sound confident but his voice quivering with urgency.

Thida laughed softly, her sultry, mocking tone sending shivers down his spine. She pressed a button on her phone, and instantly, the spikes inside the chastity belt expanded, pressing painfully into the flesh of his cock. At the same time, a tight band constricted around his balls, and a sharp electric shock jolted through him, making him collapse to his knees.

Bending down to his level, Thida's eyes glinted with dark delight as she leaned close, her breath hot against his ear. "There's an elastrator built into your chastity belt," she whispered, her voice dripping with menace. "I can castrate you whenever I choose. Those sharp pins will pierce straight through your cock if you disobey. If you ever want to cum again, you will do exactly as I say, cuck boy. Do I make myself clear?"

Robert gasped, struggling to catch his breath as he croaked out a weak, "Yes."

Without hesitation, Thida spat in his face and slapped him hard. The sound echoed through the alley, causing nearby onlookers to pause, their eyes widening in shock and fascination at the scene.

"You will address me as Mistress Slave," Thida demanded, her tone leaving no room for argument. "Do you understand?"

"Yes, Mistress," Robert replied between gasps, his voice barely audible but filled with desperate submission.

A satisfied smirk spread across Thida’s face as she pressed another button on her phone, immediately halting the intense pain. She stood up, her posture radiating dominance and control.

Without giving Robert a chance to react, Thida spun on her heel and started walking down the street with a confident, commanding sway. "Follow me if you want to experience a blowjob and anal sex," she ordered, her voice firm and authoritative, making it clear there was no room for disobedience.

Robert was momentarily stunned, his mind racing to process her sudden shift and the promise of intense pleasure. He scrambled after her, his eyes fixated on the way her tight leather-clad ass moved with each step. Her commanding presence only fueled his growing frustration and desire, making his cock strain painfully against the chastity belt.

Thida led him down a dimly lit alley, away from the bustling street and into a more secluded, intimate space. With each step, Robert's anticipation mounted. The alley ended at an old iron door, which Thida unlocked with a key before swinging it open.

She guided Robert inside and down several flights of stairs, leading him to a sex dungeon. The walls of the dungeon were adorned with whips, cuffs, floggers, gags, and a myriad of other sex toys, many of which Robert didn’t even recognize.

Turning to him, Thida's tone was uncompromising. "Strip," she commanded, her voice leaving no room for negotiation.

Robert stood naked and exposed, his only covering the steel chastity belt that cruelly mocked his desperate arousal. Thida’s eyes sparkled with sadistic delight as she methodically cuffed his hands behind his back and secured his ankles. She fastened a collar around his neck and attached a leash, gripping it with an air of utter dominance. With a commanding tug, she led him into the dimly lit sex dungeon, his discarded clothes left outside the door like a discarded memory.

The dungeon was thick with the scent of leather and an electric anticipation. Thida led him to a St. Andrew’s cross, and with deliberate care, she strapped him in, stretching his body into a vulnerable, open position. The steel chastity belt pressed painfully into his cock, amplifying every touch and movement into a cruel form of tantalizing torture.

Thida picked up a leather flogger, the straps whispering softly as she prepared to torment him. She took her time, her eyes never leaving his as she drew the flogger back. With deliberate precision, she began to whip his exposed ass. Each strike was sharp and precise, sending waves of intense pain mixed with a raw, primal thrill coursing through Robert. The sting of the leather was relentless, each crack accompanied by his yelps of pain.

“Count each strike and thank your Mistress,” Thida purred, her voice smooth and commanding, dripping with authority.

Snap!

“One, thank you, Mistress,” Robert cried out, his voice trembling with a blend of agony and forbidden pleasure.

Crack!

“Two, thank you, Mistress,” he gasped, each word punctuated by the biting sting of the flogger.

The rhythm of the flogger continued, each strike intensifying the fire on his ass. By the time she reached fifty, Robert’s face was streaked with tears, his skin a canvas of red welts and throbbing pain. Each mark was a reminder of his helplessness, each cry a testament to his surrender.

Thida moved on to Robert’s nipples with calculated cruelty, her touch both precise and punishing. She applied clamps and clothespins, twisting and adjusting them with deliberate intent. Each tug and pinch sent searing jolts of sensation through his already tortured body. Robert’s pleas and whimpers were ignored which only heightened Thida’s sadistic pleasure.

Ignoring his desperate cries, Thida gagged him with a red rubber ball, shoving it firmly into his mouth and securing it behind his head. The gag muffled his protests but did nothing to silence the waves of humiliation and helplessness that crashed over him. His face flushed with a mixture of pain and shame as he struggled futilely against the restraints.

Thida’s attention then turned to an array of tools laid out before her. She began with ball crushers and weights, tormenting his sensitive balls with calculated precision. Each squeeze and shift was a fresh wave of agony, causing him to writhe and squirm. His muffled cries of distress were swallowed by the oppressive atmosphere of the dungeon, his discomfort a symphony to her control.

She wasn’t finished yet. Thida selected several candles, their wax promising a different kind of torment. With a slow, deliberate hand, she began to drip hot wax across Robert’s back. The warmth of the wax was a stark contrast to the cool dungeon air, and as it hardened on his skin, it left him feeling exposed and vulnerable. Each painful drip drained his energy, adding to the relentless degradation.

Throughout this torment, Robert's body responded involuntarily to Thida’s dominance. He leaked profusely from the chastity belt, the cruel device only amplifying his state of helpless arousal. The scent of Thida’s leather, her intoxicating perfume, and her commanding presence combined to push him further into a state of tortured desire. His body, despite the chastity belt, betrayed his intense need for her.

After hours of relentless torture, Thida unceremoniously cuffed him to a bench. Robert’s entire body trembled uncontrollably, his ass covered in angry red stripes and welts from the flogging. His back was slick with hardened candle wax, his balls bruised and swollen from the relentless ball crushers, and his nipples raw and sore from the clamps.

Thida stood over him, a satisfied smirk curling on her lips. She had pushed him to his absolute limits, her control over him unwavering and complete.

Finally, Thida approached Robert with deliberate, sensual strides. Her hips swayed seductively, accentuating the dominance she wielded over him. As she drew near, her waist level with his mouth, she leaned in, her voice dripping with wicked intent. “I promised you’d experience a blowjob and anal sex today,” she whispered, her words sending a shiver of anticipation and dread down Robert's spine.

Thida's touch was both merciless and intoxicating, and Robert could do nothing but wait, his mind a whirlwind of desperate desire and humiliation as he lay at her mercy.

Slowly and deliberately, Thida unbuckled the front of her leather outfit, revealing her secret—a massive nine-inch cock, thick and throbbing with desire. Robert’s eyes widened in shock and arousal as the truth sank in. Thida was trans, and everything about her—the strength, the confidence—suddenly made perfect sense.

With a satisfied smirk, Thida reached for her phone and pressed a button. Immediately, sharp spikes within Robert's chastity belt pierced his cock, sending electric shocks racing through his balls. The pain was excruciating, sharp and relentless, drawing tears from his eyes as he struggled helplessly against the cuffs that bound him to the bench.

"The pain stops when my balls are empty," Thida said, her voice cold and commanding.

Desperate for relief, Robert eagerly took her cock into his mouth, savouring its warmth and hardness as he enveloped it with his lips. He sucked hungrily, his tongue swirling around every inch, licking and teasing with fervent dedication. Thida's moans of pleasure filled the air, her cock growing even harder as he worked to make her come, her precum starting to spill into his mouth.

Feeling her climax approaching, Thida pulled away with a predatory grace and positioned herself behind Robert. She collected the precum dripping from his chastity cage, using it to slick up her throbbing cock. The anticipation was almost unbearable as she pressed the thick head of her cock against his tight, eager hole.

Robert gasped as she began to push, the sensation a sharp mix of pain and pleasure that stretched him to his limits. Inch by inch, she worked her way inside him, filling him completely until she was buried to the hilt. Robert’s body trembled and his breath came in ragged gasps as she began to move, her thrusts quickening and intensifying with each powerful stroke.

“Who owns this ass?” Thida growled, her hand landing a stinging smack on the tender welts of his ass, the sharp crack echoing through the room.

“Mistress does!” Robert gasped, his voice quivering with a mix of pain and helpless desire.

“Who owns these balls?” she demanded, her fingers gripping his balls with a crushing intensity, drawing out a cry of agony from him.

“Mistress does!” he shouted, his voice breaking under the excruciating pressure.

“And who is my bitch?” Thida snarled, her thrusts growing more relentless and merciless, pounding into him with unyielding force.

“I am! I am your bitch!” Robert sobbed, his voice raw and breaking as he gave in completely to her commanding dominance.

With a primal groan, Thida seized a fistful of Robert’s hair, yanking his head back as she drove deeper into him. The sensation was overwhelming—her massive cock stretched him completely, sending shivers through his body with each powerful thrust. As she reached her peak, she erupted inside him, her hot cum flooding his tight hole, spilling over and pooling on the floor. Her body convulsed with each forceful thrust, and her loud moans filled the room, her pleasure intense and unrestrained.

Once she was satisfied, Thida’s moans softened to a satisfied purr as she pressed a button on her phone, halting the agonizing shocks to Robert’s cock and balls. She then uncuffed him from the bench, and he collapsed to the floor, his body quaking from the relentless punishment.

“Clean up this mess,” Thida commanded, nudging the cum-soaked floor with her boot.

Broken and utterly submissive, Robert crawled over to the mess, his tongue scraping eagerly against the cold floor as he licked up every drop of her cum. When he finished, Thida instructed him to kneel, his head bowed to the ground, his hands bound behind his back.

There was no fight left in him. Robert followed her commands with absolute obedience, his spirit completely shattered. For the next hour, Thida trained him rigorously, drilling into him the various positions he would assume at her command. Each order was met with immediate compliance as she reshaped him into her sissy, her plaything, her submissive bitch, revelling in her absolute control over him.

With a teasing smile, Thida handed Robert a delicate pair of pink panties and a matching bra, along with a sheer white skirt and a flimsy top. The fabric was so thin that it promised to reveal every intimate detail of the lingerie beneath.

“It’s time to go, cucky,” she purred, her voice dripping with authority.

Robert slipped into the clothes, the silky fabric heightening his sense of vulnerability. As they stepped outside, Thida moved several paces ahead, leaving him to follow in her wake. He couldn’t help but focus on the hypnotic sway of her hips, as she had instructed.

Each step through the bustling streets of Bangkok deepened his humiliation. The tight pink panties clung to him, and the sheer white skirt and top left little to the imagination. The bra straps were clearly visible through the flimsy fabric, and the outline of his chastity belt was faintly noticeable beneath it. Passersby giggled and whispered, some even capturing the moment with their phones, turning his shame into a public spectacle.

What tormented Robert the most was the relentless ache of his trapped erection, confined by the unyielding chastity belt. Just moments before, he had been on his knees, Thida's cock still lingering on his lips. The realization that Thida was trans had only heightened his arousal and confusion, especially after she had filled him completely.

As they walked, Thida suddenly stopped and turned to face him. Robert quickly lowered his eyes, staring submissively at her leather boots, his heart pounding with a mix of fear and excitement. He knew he was not allowed to meet her gaze unless she granted him permission.

“Good girl,” she mocked, a cruel smirk curling her lips as she noticed his obedience.

“I’ll see you next Tuesday for our next lesson, sissy,” she added with a wicked glint in her eye before turning on her heel and strutting away.

“Yes, Mistress,” Robert managed to reply, his voice trembling with shame and desire as he watched her disappear into the crowd.

Left standing there, dazed and humiliated, Robert felt the weight of his new reality pressing down on him. In just two meetings, Thida had not only locked him in chastity but had also begun reshaping his very identity. Dressed in women’s lingerie and a chastity belt, the full weight of his submission became painfully clear. There was no turning back now.