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.