Tim was on the edge of insanity. Two months had passed since Rebecca locked him in chastity, and his torment felt endless. Every day was a living nightmare—his balls ached constantly, feeling impossibly heavy, and the constant, humiliating dribble from his caged cock reminded him of his desperate state.

There was no relief in sight, only the knowledge that the woman who held the key to his release—his best friend’s older sister, the woman he’d been in love with for years—had complete control over him.

He sat by the pool with Mark, trying to act normal, though his mind was consumed with thoughts of Rebecca. The moment she emerged from the water, glistening in the sun, her body wrapped in a tiny, tight red bikini, Tim felt his cock strain helplessly against the chastity cage. His balls felt like they were about to explode. The sight of her, so confident and unattainable, made him even more desperate.

But Rebecca barely acknowledged him, and that only fueled his frustration. He was ready to burst from the aching need that built up every second, yet she carried on as if he didn’t exist. The memory of two weeks ago still burned fresh in his mind—the way she had him cuffed to the motel bed, her panties stuffed in his mouth, leaving him powerless as she teased him mercilessly.

She had whispered promises of release, but it had been a lie. Now, here he was, ignored and locked away, still trapped in the cage she commanded him to wear.

As Mark headed back to the room to grab his power bank, Rebecca stretched out on the lounge chair, her body glistening in the sun. She turned her head toward Tim with a sly smile, her eyes sparkling with mischief. "Why don’t you be a good boy and put some suncream on my back, sissy?" she teased, her voice dripping with playful cruelty.

Tim’s face turned bright red, his heart racing as he hurried over. He picked up the bottle with shaky hands, squirting the cool cream into his palm before nervously placing it on her shoulders. As his hands began to rub the lotion into her firm, tanned skin, he felt the heat rising inside him. The feel of her beneath his fingers was intoxicating, and when Rebecca let out a soft, satisfied purr, it nearly pushed him over the edge. His cock strained painfully against the cage, throbbing uselessly, locked away.

As his hands moved lower down her back, his breath quickened, and then she spoke, her voice low and sultry. "Don’t forget my cheeks, sissy," she whispered with a wink, glancing back at him. "We wouldn’t want them to burn, would we?"

Tim's face burned with arousal and humiliation, his cock now rock-hard and throbbing in the chastity belt. There was nothing he could do about it. Trembling, he moved his hands to her ass, massaging the cream into her thick, firm cheeks. His balls felt like they were going to burst from the overwhelming need building inside him, every second more unbearable than the last.

Another purr from Rebecca nearly made him black out from frustration. As he worked his way down her thighs, his eyes caught sight of something that made his heart skip a beat. Around her left ankle, a delicate gold bracelet shimmered in the sunlight, and dangling from it was a tiny key—the key to his chastity belt.

Tim let out a soft, helpless whimper, his fingers freezing for a moment as he stared at it. Rebecca didn’t miss a beat. She smirked knowingly, feeling his reaction without even needing to look. "Careful, sissy," she purred, "I can feel how close you are."

With shaky hands, he continued down her calves, reaching her feet. He gently moved the ankle bracelet aside to rub in the sunscreen, his entire body red with arousal and shame. The nearness of the key, so close yet so impossibly out of reach, drove him wild. He wanted so badly to beg, but he knew Rebecca wouldn’t give in.

"That’s enough, sissy," Rebecca finally purred, rolling onto her back, her massive breasts nearly spilling out of the tiny bikini top. She stretched her arms above her head, the curve of her body on full display, and glanced at him, her eyes dancing with amusement. "You did well… for now."

Tim’s cock pulsed painfully in its cage, but Rebecca’s teasing gaze only left him more desperate, knowing his torment was far from over.

Tim went back to his room and took a long, cold shower, trying to ease the pain in his balls with the cold water as his entire body felt like it was on fire from how horny he was.

Tim arrived at the dinner table, trying to keep his cool. The restaurant was beautiful, perched right by the beach, with the warm glow of sunset spilling through the windows. The evening breeze carried the scent of the ocean, and the sound of waves crashing added a soft, soothing backdrop to the quiet chatter of diners. Mark and Rebecca’s parents were engaged in conversation about the day's activities, while Mark scrolled through his phone, oblivious to the tension brewing beneath the table.

Rebecca sat directly across from Tim, wearing a tight leather dress that hugged her curves perfectly, her long legs crossed underneath the table. As Tim tried to focus on the menu, he felt a sudden, gentle brush against his shin. His body tensed immediately, and he glanced up to see Rebecca smirking at him, her eyes sparkling with mischief.

He swallowed hard, trying to maintain composure as her bare foot began to slide slowly up his leg, teasing him. She pretended to focus on the conversation around her, but Tim could feel her full attention locked on him. The soft, deliberate caress of her foot traveled higher, reaching his thigh, sending a wave of heat through his body. His cock throbbed helplessly in its cage, already straining from the subtle torment.

Rebecca’s foot moved higher, pressing against his crotch, the pressure making him bite back a whimper. His pulse quickened as he squirmed in his seat, trying not to make it obvious. Every slight shift of her foot sent sparks of arousal surging through him, his body reacting instinctively even though he knew there would be no relief.

“Tim, are you feeling okay?” Rebecca asked sweetly, her voice dripping with false innocence. She rubbed her foot harder against his crotch as she spoke, making his heart pound in his chest. “You seem… tense.”

Tim nearly choked on his drink, his face flushing as he tried to respond. “I-I’m fine,” he stammered, avoiding eye contact. Mark and Rebecca’s parents didn’t notice a thing, too caught up in their own conversation.

Rebecca leaned forward slightly, her eyes never leaving Tim as she took a sip of her wine. “Good,” she purred, her voice barely loud enough for him to hear. “I’d hate for you to be uncomfortable… especially with everything you’re carrying around.”

Her words were laced with hidden meaning, and Tim’s cheeks burned. The pressure from her foot continued, the friction unbearable, and his cock strained against the cage, throbbing painfully as her teasing foot worked him up. He was so close to losing control, but Rebecca knew exactly how far to push him.

“I can’t imagine how hard it must be for you,” she added, her tone smooth and casual, while her foot slid slowly back down his leg. “It’s been so long, hasn’t it?” Her eyes gleamed with cruel amusement as she took another sip of wine, savouring his reaction.

Tim could only nod, feeling trapped between the teasing pressure of her foot and the helpless frustration of his cage. He wanted so badly to beg for relief, but he knew Rebecca wouldn’t give it to him. Not here, not now. She was toying with him, dangling the possibility of release just out of reach, and there was nothing he could do but endure it.

Rebecca’s foot retreated at last, but the smirk never left her face. “Good boy,” she murmured under her breath, her gaze flicking down to his lap before returning to her meal, as if nothing had happened.

Tim sat there, painfully hard and fully aware of how much control Rebecca held over him. The casual, quiet torment she inflicted on him was maddening, but he couldn’t deny the thrill that came with her power. As dinner continued, Tim did his best to participate in the conversation, but his mind remained on the woman across from him—the woman who held his key, his torment, and his deepest desires in the palm of her hand.

Tim barely made it up to his room before he received a message from Rebecca telling him to be outside the building at 1 am or the photographs of him dressed as a sissy will be shared with everyone they know.

Tim’s heart raced as he checked the time: 12:58 AM. The place was silent, everyone asleep, just as Rebecca had instructed. His pulse quickened as he quietly slipped out of bed and made his way outside, careful not to wake anyone. The night air was cool, the only sound the soft rustle of leaves in the breeze. His mind buzzed with anticipation and fear—Rebecca had been more cryptic than usual when she told him to meet her outside.

As he reached the driveway, Rebecca’s sleek rental car pulled up, her headlights briefly illuminating his anxious face. The car door opened, and she beckoned him inside with a smirk. She wore a long black coat , her dark eyes gleaming with mischief. "Get in, sissy," she said, her voice smooth and commanding.

Tim slid into the passenger seat without a word, the air between them thick with unspoken tension. His chastity cage pressed uncomfortably against his skin, a constant reminder of the control Rebecca held over him. She didn’t say anything as they drove, the hum of the engine filling the silence. But every now and then, Rebecca would glance over at him, her lips curling into a sly smile as if she knew exactly what was running through his mind.

After what felt like an eternity, they pulled up to an unmarked building on the outskirts of town. The area was deserted, the only light coming from a dim bulb above a steel door. Rebecca parked and turned off the engine, her gaze locking onto Tim’s. "We’re here," she said, her tone dripping with anticipation.

Tim’s throat was dry as he followed her inside, his heart pounding. The interior of the building was dark and quiet, save for the soft click of Rebecca’s heels on the floor as she led him through a narrow hallway. They entered a large room, dimly lit by red-tinted lights. Tim’s eyes widened as he took in the sight before him—a fully equipped BDSM dungeon.

The walls were lined with shelves of floggers, whips, and restraints, and in the center of the room stood a St. Andrew’s cross, gleaming under the low light. A large bed with leather straps at each corner sat to the side, along with a bench and a rack of toys, from dildos to paddles.

Rebecca turned to face him, her eyes alight with amusement and power. “Strip,” she commanded, her voice firm.

Tim’s hands shook as he obeyed, quickly undressing until he stood naked before her in only his chastity cage, the cold air brushing against his skin. The chastity cage gleamed under the red light, a constant reminder of his submission. Rebecca watched him with a predatory gaze, her lips curling into a smile as she approached him, her fingers grazing the cold metal of the cage. “Still locked up, I see,” she whispered, her tone mocking. “Good. You don’t deserve to be free.”

She then removed her coat revealing a tight black latex outfir that cling to her curvy body like a second skin. Her firm breasts were on full display for Tim to admire as he squirmed in the cage.

She walked to the rack of toys, taking her time as she selected a flogger, the leather strands swaying in her hand. “Come here,” she said, her eyes locking onto his, daring him to disobey. Tim swallowed hard, his legs trembling as he stepped toward her. Rebecca grabbed his wrist and pulled him roughly toward the St. Andrew’s cross, fastening his wrists and ankles to the restraints. His chest pressed against the cold wood, his heart hammering in his chest.

“You’re mine tonight,” Rebecca purred, trailing the flogger lightly across his back, teasing him with the sensation. “And you’ll take everything I give you.”

With that, she brought the flogger down hard on his back, the sharp sting making him gasp. She struck him again, and again, each blow sending waves of heat and pain through his body. Tim’s breath came in ragged gasps as she alternated between soft, teasing strokes and harsh, stinging blows, her control over him absolute.

After several minutes, she tossed the flogger aside and reached for a whip, the thin leather snapping in the air as she tested it. “Let’s see how much you can take, sissy,” she said, her voice low and dangerous. The first crack of the whip against his ass made Tim cry out, his body jerking against the restraints. But Rebecca didn’t slow down. She whipped him mercilessly, each lash more intense than the last, until his back was on fire, and he was panting with pain and arousal.

When she finally stopped, Tim’s body was trembling, his mind swimming in a haze of pain and submission. Rebecca unstrapped him from the cross, guiding him over to the bed, where she quickly cuffed his wrists and ankles to the leather straps. He lay there, completely vulnerable, his body aching but his cock throbbing in its cage, desperate for release.

Rebecca smirked as she reached for a ten-inch black strap-on from the rack, securing it around her waist with practiced ease. The dildo was thick and intimidating, gleaming in the low light. “I’ve been waiting for this,” she murmured, running her hand over his trembling thighs.

Without warning, she flipped him over onto his stomach, positioning herself behind him. Tim’s breath caught in his throat as he felt the tip of the strap-on press against his ass, his heart racing in a mixture of fear and excitement. “Beg for it,” Rebecca demanded, her voice dripping with authority.

“P-please,” Tim whimpered, his voice barely audible. “Please, Rebecca…”

“Good boy,” she purred, and with that, she pushed forward, the thick dildo stretching him as she thrust into him, slow and deliberate at first. Tim gasped, his body tensing, but there was no escaping it. Rebecca set a steady, punishing rhythm, her hips driving into him relentlessly. Each thrust pushed him further into submission, his mind consumed by the overwhelming sensation of being used, controlled, dominated.

As she took him harder and deeper, Rebecca’s hand snaked around his body, gripping the chastity cage firmly. “Still locked up,” she teased, her breath hot against his ear as she continued to thrust into him. “Maybe… if you’re a good boy… I’ll think about letting you out. But not tonight.”

Tim’s entire body trembled, caught between pain, pleasure, and the unbearable frustration of knowing he was still trapped. He whimpered beneath her, completely at her mercy, as Rebecca drove him deeper into submission with every stroke, every whisper of her power.

Tim’s body trembled as he finally broke, his voice hoarse from pleading. "Please… Mistress, I can’t take anymore. Please stop."

Rebecca paused, the relentless rhythm of the rubber cock driving into him halting for just a moment. Her lips curled into a wicked smile, her eyes gleaming with satisfaction. She leaned in closer, her breath hot against his ear. "Oh, is that so?" she teased, her voice dripping with amusement. "And what would you be willing to do for me to stop?"

"Anything," Tim panted, moaning as the thick, ten-inch rubber cock continued to stretch and fill him with each thrust. His body ached, but his desperation to please her overpowered the pain.

Rebecca’s sly grin widened. She pulled out the dildo with a slow, deliberate motion, savoring the sight of him quivering beneath her. Without a word, she uncuffed him, watching as he collapsed onto the bed in a heap of exhaustion and need.

"Get dressed," she commanded, her voice now cool and commanding. "We need to visit the salon next door before it closes."

Tim blinked, struggling to focus through the haze of arousal and relief. "A salon… at 3 AM?" he muttered to himself, confused.

Rebecca didn’t bother to answer, her eyes glinting with something far more sinister. Whatever she had planned, Tim knew it wouldn’t be just a simple trip to the salon. There was always more—always another layer of her twisted, teasing control.

When Tim arrived home, he collapsed onto his bed, the soreness in his body a constant reminder of the night with Rebecca. His ass was covered in bruises and welts from the relentless whipping she’d given him, each mark a testament to her control. His balls ached, swollen and bruised, throbbing in sync with the cage that still tightly confined him.

Slowly, he slid off his underwear, exposing the area just above his caged cock. The inked words that Rebecca had ordered tattooed there glistened across his waved pubic region, bold and permanent: "Property of Mistress Rebecca." The black lettering, stark against his skin, made his cock twitch helplessly in its prison, unable to respond as his arousal surged.

Just then, his phone buzzed. His heart skipped a beat as he saw Rebecca's name flash on the screen.

"Keep next Saturday free, sissy. It’s time for me to introduce you to my friends..." 

Tim’s stomach fluttered with a mix of dread and excitement. He knew this would be far more than a casual coffee outing. No, when it came to Rebecca, there was always something more intense, more thrilling—and kinkier—hidden behind her words. The possibilities raced through his mind as he imagined what she had planned, his body already responding to the thought of being paraded in front of her friends, subjected to her whims and their amusement.

With trembling fingers, he typed the only response he knew she expected, the one that would confirm his submission.

"Yes, Mistress."