Captions XXXVI

 

One Night Stand Leads To Permanent Chastity

Matt was a 20-year-old virgin, his days consumed by an insatiable need for release. He masturbated four to five times daily, each session leaving him more frustrated and desperate than the last. His fantasies grew wilder, his desire to lose his virginity becoming an all-consuming obsession.

Late one night, as he browsed through an online chat room, he stumbled upon a profile that made his heart race. Her name was Ruby. She was an incredible blonde with big tits and intricate tattoos that wound their way over her stunning body. Her pictures were enough to make Matt's breath hitch, and when she messaged him, he couldn't believe his luck.

Their conversation quickly turned steamy. Ruby was confident, and experienced, and she seemed genuinely interested in Matt's predicament. She teased him mercilessly, drawing out his fantasies and pushing all the right buttons.

"How would you like to lose your virginity to me?" she finally asked her words a promise of everything he'd ever dreamed of.

Matt's hands trembled as he typed his eager response. "I'd love that. I need it so bad."

She responded almost instantly. "There's a catch, though. I want to indulge in some role-play. If you're game, we can meet at a motel."

The idea of role-playing excited Matt even more. He didn't care what she had in mind; he was ready to do anything for this chance. "I'm in," he replied, his anticipation growing with every second.

"Perfect," Ruby replied. "Let's set a date for this Friday. I'll send you the details. Be ready for the night of your life."

Matt could hardly contain his excitement. He spent the rest of the night masturbating over and over. His mind racing with thoughts of what was to come. He knew that Friday night would change everything.

As Matt stood nervously in the dimly lit motel room, his heart pounded in his chest. He couldn't believe he was finally meeting Ruby, the woman who had promised to take his virginity.

She entered the room with a confident stride, her blonde hair cascading over her shoulders, her tattoos peeking out from under a tantalizingly sheer blouse.

"You must be Matt," Ruby purred, her voice sending shivers down his spine. She closed the distance between them, her eyes tracing his body as if undressing him with her gaze. "You're even cuter in person."

She lay down on the bed facing Matt, her alluring, perky breasts straining against the fabric of her red top, teasing him with every breath she took.

Matt's cheeks flushed as he struggled to maintain composure. His pants felt uncomfortably tight, his arousal evident despite his attempts to hide it.

Ruby smiled knowingly, her lips curling into a mischievous grin. "I can see you're excited," she teased, reaching out to lightly brush her fingers against the bulge in his pants. "But first, let's get into character."

Matt's breath caught in his throat as Ruby led him to a suitcase on the bed. She pulled out an array of clothing—lingerie, stockings, a blonde wig and makeup.

"Put these on," she instructed, her tone firm yet playful. "It's part of our little game."

Nervously, Matt complied, slipping into the silky lingerie and stockings under Ruby's watchful gaze. Each brush of her fingers against his skin sent jolts of desire through him, intensifying his arousal. As she adjusted the outfit, her hands lingering on his body, he felt a surge of excitement. Her touch was electric, and the sight of her teasing smile only heightened his anticipation, making his heart race with lust.

Ruby stepped back, her eyes sparkling with mischief as she held up a delicate makeup brush. "Now, let's make you even prettier," she purred, leaning in close. The scent of her perfume filled his senses, making him dizzy with desire. She gently applied blush to his cheeks, her fingers grazing his skin, sending shivers down his spine.

Her voice dropped to a seductive whisper as she worked. "You look so hot like this, Matt. I can hardly keep my hands off you." She traced a finger along his jawline before applying lipstick to his trembling lips. The sensation of the makeup and her soft touch made his breath hitch, his body responding eagerly to her every move.

Ruby's eyes locked onto his, a sly smile playing on her lips. "You have no idea how turned on I am right now," she teased, running a hand through his hair and adjusting a stray lock. "Seeing you like this, so vulnerable and sexy, drives me wild."

She stepped back to admire her handiwork, her gaze smouldering. "You're perfect," she murmured, her fingers trailing down his arm. "I can’t wait to see what else we can explore together." Her words, laced with promise and temptation, made his pulse quicken, the anticipation of what was to come leaving him breathless.

"Now," Ruby said, her voice low and commanding, "lie down on the bed."

Matt obeyed, his heart racing with anticipation and a touch of apprehension. Ruby secured his wrists to the top of the bed, her touch both firm and teasing. She then pushed his legs up over his head, exposing him completely, before securing them to the metal post at the top of the bed. Matt's ass was on full display, his vulnerability heightening his arousal.

"Be back in a second," she purred, her voice dripping with seduction as she disappeared into the bathroom.

Matt couldn't believe what was happening. He liked kinky stuff, but this was on a whole new level. She had crossdressed him and now had him cuffed to the bed, completely at her mercy. The mixture of excitement and nervousness coursed through him, making him harder with each passing second.

Ruby exited the bathroom, a mischievous smile on her lips and an eight-inch strapon dangling provocatively between her legs.

"Tonight you're going to lose your anal virginity, Matt," she teased, climbing onto the bed with a predatory grace.

Matt's eyes widened as he suddenly realized why she had pushed his legs over his shoulders before cuffing them. His breath quickened, a mix of fear and arousal pulsing through him.

With practised ease, Ruby positioned herself between Matt's legs. She took her time, teasing him with gentle touches and kisses, driving him to the brink of madness. Ruby spat on the strapon, lubricating it with deliberate, slow movements.

She positioned herself, the tip of the strapon pressing against his entrance. With a slow, deliberate push, she began to enter him, eliciting gasps and moans from Matt. The sensation was intense, a blend of pleasure and pain that left him gasping for more.

She picked up the pace, thrusting deeper and harder as Matt's gasps grew louder and more desperate. The room filled with the sounds of their bodies moving together, the raw, primal rhythm driving him wild. Ruby paused only to reach for a rubber ball gag, pushing it gently but firmly into his mouth, muffling his cries of pleasure.

With the gag in place, she resumed her rhythm, each thrust sending waves of ecstasy through Matt's body. He could only surrender to the overwhelming sensations, his mind consumed by the intense, erotic experience that Ruby was orchestrating with skilful dominance.

As she reached the peak of her climax, her passionate moans and the relentless rhythm of her thrusts drove Matt over the edge, causing him to explode in ecstasy, his hot cum splattering all over his own face.

Panting, Ruby slowly withdrew her strapon from Matt, savouring the sight of his trembling body. With a wicked smile, she replaced it with a vibrating butt plug, pushing it in gently but firmly, eliciting another moan of pleasure from Matt as the intense vibrations sent waves of ecstasy through his entire being.

She uncuffed his ankles from the top of the bed and cuffed them to the bottom of the bed so he was tied spread-eagle to the bedposts. He was completely at her mercy, his body thrumming with excitement and a hint of fear.

Matt couldn't believe his luck. This stunning blonde had crossdressed him, bound him, and fucked him with a strapon, pushing him to the brink of ecstasy. Now, with the anticipation building, all that was left was for him to lose his virginity completely, making the night unforgettable.

He felt his hot cum dripping down his face, the sensation both humiliating and arousing, but the ball gag in his mouth silenced his moans and left him powerless to speak.

Ruby walked over and picked up a small brown package.

Matt lay on the bed, his body still tingling from the intense experience he had just undergone with Ruby. His heart raced as she approached him again with the brown package. She began to slowly open it before removing a steel metal chastity belt in her hands.

His eyes widened with a mix of fear and arousal as she knelt beside him, as he muffled through the gag in his mouth.

She slowly began to place it on his cock and balls. It was so tight, that Matt was convinced it wouldn’t fit. Matt didn’t know what kinky game she had in store for him, but he wasn’t going to lose his virginity with this thing locked on.

She expertly adjusted the parts, each click sending shivers of anticipation through Matt, until the whole contraption was perfectly in place. With a lustful gaze and a shudder of pure ecstasy, she let out a massive orgasm, her body trembling as she reveled in the intensity of the moment, clearly finding this to be the hottest and most thrilling thing she had ever experienced.

She then began to stroke Matt’s head as he muffled through the gag and pulled on the restraints.

"Listen carefully, Matt," Ruby said softly, her voice a soothing contrast to the tumultuous emotions swirling inside him. "This chastity belt is unbreakable. It's designed to keep you in a constant state of arousal, but you'll never be able to orgasm."

Matt's eyes widened further as he listened, the reality of his situation sinking in. His cock strained against the confines of the belt, desperate for release that would never come.

"Several times a day," Ruby continued, her tone matter-of-fact yet tinged with a hint of sadistic pleasure, "a built-in massager will turn on and edge you, bringing you right to the brink. But just when you think you can't take any more, it will stop, denying you release."

Matt squirmed against his restraints, his breath coming in shallow gasps. He was both terrified and inexplicably aroused by Ruby's words.

"There's a combination lock," Ruby went on, her fingers tracing the contours of the chastity belt teasingly. "You can try to unlock it, but I must warn you, Matt—it will hurt. The more you try, the more intense the pain will become."

Tears welled up in Matt's eyes as he realized the full extent of his predicament. He was trapped, completely at Ruby's mercy, his desires and fears laid bare before her.

"Are you starting to understand, Matt?" Ruby asked softly, her gaze penetrating. "This belt is a reminder of tonight. I told you I would take your virginity and I did."

The vibration around his cock and balls kicked in. The relentless vibrations on his balls and shaft teased him mercilessly, bringing him agonizingly close to the edge before abruptly stopping. His cock strained within the confines of the cage, leaking precum, the sensation unbearable.

It has been a pleasure, but it is time for me to go she said. Matt let out a muffled scream into the gag.

"Don’t worry, room service will find you in the morning," she winked before sauntering out of the room and closing the door behind her.

Matt tried to yell after her, but the gag rendered him helpless. He groaned inwardly, feeling exposed and vulnerable. "Great… here I am crossdressed, cuffed to a bed, gagged with a face full of my own cum..."

The next day, room service burst into laughter at Matt’s predicament. They couldn’t resist taking a few pictures before finally calling the local fire brigade to cut the cuffs off him and the bed. It was a deeply humiliating experience for Matt, one that would linger in his mind for a long time.

Several days later in his room, Matt sat on his bed with tears flooding down his face.

"How am I supposed to live like this?" he wondered, anxiety gripping him as he fondled the unbreakable chastity belt attached to his cock and balls.

Just as he sat there, the vibrations suddenly came to life, teasing and caressing his sensitive balls and shaft with tantalizing precision. They brought him to the brink of ecstasy, his breath hitching as pleasure surged through his body, only to abruptly stop. Matt couldn't help but let out a desperate cry of frustration, longing for more of the intense pleasure that had been so abruptly denied.

Desperate, he opened the combination section, but the moment he did, the ball crusher activated in the cage, mercilessly squeezing his balls. The pain was excruciating, a blinding agony that made him gasp.

Frantically, he entered a combination into the lock: 00000000000001. Instantly, a massive zap surged through his balls, causing him to yelp in pain. "That must have been the wrong combination…"

He tried again: 00000000000002. Another massive zap. He cried out, the pain searing through him, and the combination section snapped shut. "Wrong again…"

Sweat poured down his face as he panted, his mind consumed by the throbbing ache and desperate need for release. "I have to get this off!"

With trembling hands, he entered another combination: 00000000000003. A fierce shock surged through his balls, the pain nearly unbearable. "Wrong again…" he gasped, his body convulsing with each wave of agony, his fear mounting that he would never escape this torment.

"I just wanted to lose my virginity. Instead, I'm left here, teased and denied, with no hope of ever feeling that release again," Matt lamented, his voice thick with frustration and longing.

Driving down the highway in her convertible, Ruby couldn’t help but laugh.

She had now locked 376 men in these chastity devices, and none of them had figured out her cruellest secret.

No combination was ever going to open the chastity belt. She had left that hope dangling just out of reach, ensuring their balls would be crushed and zapped for the rest of their lives as they futilely tried to move on from that unforgettable night with her.

Her pants became moist as she imagined someone eventually entering every single combination, thinking they must have missed one or made a mistake along the way.

Or maybe, finally, the realization would dawn on them that the chastity belt was never coming off. The thought of their eternal frustration and hopelessness sent shivers of pleasure through her.

She looked down at her phone, a wicked grin spreading across her lips as she saw dozens of messages from eager young virgins, each begging to lose their virginity to her in a motel. The anticipation and desire radiated from their words, fueling her arousal. She was going to lock every one of them up...