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Chained to Desire

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Jim is a closet sissy in self-chastity that desires a keyholder who will give him humiliating tasks that include feminization, giving men blowjobs and public exposure as a condition for release from chastity. He joins an online chastity app (chaster) and creates a lock with the most humiliating and feminizing tasks, including not only giving men blowjobs, but asking them to take his picture and post online. He must spin the "wheel of fortune" several times a day, which contains tasks, penalties (liking having time added or time frozen) and potential rewards (reduction in time). He finds a keyholder on the app, Sascha, a sexy, but mean-spirited woman that happily agrees to be his keyholder, for a fee. Jim agrees and pays her a daily $100/fee and embarks on a humiliating journey that ends with him finally sucking his first dick and sending the pic to her after 8 days in chastity.

Chapter 2: Building Tension

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Jim's apartment was a circus of chaos, each new task from Mistress Sascha adding another layer to the absurdity. Neon lights flickered, casting a garish glow on the anime figurines and erotic art that cluttered every surface. The air was thick with the scent of cigarette smoke and cheap cologne, a testament to Jim's nervous habit and desperate attempts to mask his shame.

He sat at his desk, the old wooden chair creaking under his weight, the laptop screen casting an eerie glow on his face.

He was supposed to be working, but his mind was elsewhere, consumed by the thought of his next task. He had sent Mistress Sascha the picture, as instructed, and now he was waiting for her response, his heart pounding in his chest.

His phone buzzed, and he jumped, his eyes darting to the screen. It was a message from Mistress Sascha. "Good morning, Jim. I see you've followed my instructions. I'm pleased. Today's task is a bit more... challenging. You'll wear a pair of crotchless panties under your work clothes.

You'll go about your day as usual, but you'll be acutely aware of your exposed vulnerability. You'll not touch yourself, even to adjust the fabric. If you feel the urge to climax, you'll hold it back. If you can't, you'll send me a message, and we'll discuss appropriate punishment.

Jim's breath hitched as he read the message. The thought of going about his day, his most intimate area exposed and vulnerable, sent a shiver down his spine. He could feel the heat rising in his cheeks, his heart pounding in his chest.

He typed out a response, his fingers trembling slightly.

He set his phone down, his mind racing. He knew he had to get ready for work, but the thought of putting on the crotchless panties and spending the day like that was daunting. He took a deep breath, steeling himself for what was to come.

He slipped into the bathroom, locking the door behind him. He looked at himself in the mirror, his reflection staring back at him with a mix of fear and excitement.

He reached into the drawer, pulling out the pair of crotchless panties Mistress Sascha had sent him. They were made of a soft, silky material, the lace trim delicate and feminine. The crotch was cut out, leaving him exposed and vulnerable.

He stepped into them, pulling them up over his hips. The fabric was cool against his skin, the sensation sending a shiver down his spine. He adjusted himself, his cock already half-hard, and straining against his chastity cage, at the thought of what was to come. He took a deep breath, reminding himself of the rules. No touching, no adjusting.

He repeated the mantra in his head as he pulled on his work clothes - a pair of khaki pants and a button-down shirt, both of which felt too tight, too constricting. He could feel the panties with every movement, the cool silk caressing his skin, the lace tickling his thighs. He could feel the breeze against his exposed flesh, the sensation both exhilarating and terrifying. Worse still was the feeling of his trapped cock straining against his cage under his khakis, he was worried the bulge would be obvious to all his coworkers.

He made his way to the kitchen, grabbing a cup of coffee before heading out the door. He took a sip, the hot liquid scalding his tongue, a fitting punishment for his transgression.

He rushed out the door, his heart pounding in his chest, his mind racing. He knew he shouldn't have touched himself, but the sensation had been too much, too overwhelming. He sent Mistress Sascha a message, his fingers trembling as he typed out the words, "I'm sorry, Mistress Sascha. I couldn't hold back."

Her response was swift and brutal. "I see. Well, Jim, you know the rule. No touching without permission. You'll have to face the consequences. Tonight, you'll spend an hour in the chastity cage, no clothes, no distractions.

You'll reflect on your disobedience and the pleasure you denied yourself. Afterward, you'll write me a 500-word essay on why you should never touch yourself without permission again.

Jim gulped, his heart sinking at the thought of spending an hour in the chastity cage, naked and alone with his thoughts. But he knew he deserved it. He had disobeyed, and now he must face the consequences.

"Yes, Mistress Sascha," he replied, his voice barely above a whisper.

He could feel the heat rising in his cheeks, embarrassment and shame washing over him. He knew he should have been able to control himself, but the sensation had been too much.

He spent the day at work in a daze, his mind consumed by thoughts of his punishment. He could feel the crotchless panties with every movement, the cool silk caressing his skin, the lace tickling his thighs. He had to constantly remind himself not to adjust himself, not to draw attention to the bulge in his pants.

He could feel the eyes of his coworkers on him, could feel their curiosity, their judgment. He knew they could see it, the outline of his cock straining against the cage, the panties doing little to hide it. He could feel the heat rising in his cheeks, his heart pounding in his chest as he tried to focus on his work.

As the day wore on, Jim found it increasingly difficult to concentrate. The sensation of the cool silk against his skin, the constant reminder of his vulnerability, was driving him to distraction.

He could feel the familiar pressure building in his groin, the urge to climax growing stronger with each passing moment. He clenched his fists, his nails digging into his palms, forcing himself to hold back.

At lunch, he locked himself in the bathroom stall, his breathing ragged, his heart pounding in his chest. He sent Mistress Sascha a message, his fingers trembling as he typed out the words, "I can't hold back, Mistress Sascha. I need to come."

Her response was immediate, her tone stern. Well, Jim, you know the rules.

You're not to climax without my permission. Given your disobedience, I think it's time for a little punishment. I want you to go out to the store and buy a pair of those cheap, bright pink, thong panties. The kind that leave nothing to the imagination. You'll wear them under your clothes for the rest of the day. I want you to feel the fabric rubbing against you, a constant reminder of your transgression. And Jim, no underwear over them. I want you to feel the breeze against your skin, your vulnerability.

I want you to be acutely aware of your body, of your desire, and of your inability to act on it. You will not touch yourself, Jim. Not until I say so. Her words sent a shiver down Jim's spine, a mix of fear and excitement coursing through him. He knew he was in for a day of torment, but the thought of pleasing Mistress Sascha, of earning her approval, was enough to make him comply. He hung up the phone, his heart pounding in his chest.

He knew he had to go through with it, had to buy those ridiculous panties and wear them all day.

He made his way to the department store, his eyes scanning the shelves for the most obscene pair of panties he could find. He wanted to make sure Mistress Sascha was pleased, wanted to make sure he was properly punished.

He found them, tucked away in the back of the rack - a pair of bright pink, thong panties, the fabric thin and shiny, the cut high and revealing.

He felt a wave of embarrassment wash over him as he picked them up, the cool material slipping through his fingers. He could only imagine what the cashier would think, what they would say if they knew what he was planning to do with them.

He made his way to the checkout, his heart pounding in his chest, his cheeks flushed with embarrassment. The cashier, a young woman with a bored expression, barely glanced at him as she rang up his purchase. But Jim could feel her eyes on him, could feel her judgment as he handed over the panties and his credit card.

He could feel the heat rising in his cheeks, his heart pounding in his chest as he waited for her to say something, anything.

But she didn't. She simply handed him his receipt and bag, her expression unchanged. "Have a nice day," she said, her voice flat and disinterested.

Jim mumbled a thank you, grabbing the bag and rushing out of the store as fast as he could. He could feel the weight of the panties in the bag, could feel the judgment of every person he passed on the street.

He knew they couldn't see what was inside, but he felt like they could, like they could see right through the bag and into his deepest, darkest desires.

He quickened his pace, his heart pounding in his chest, his mind racing. He knew he had to get back to work, had to face the rest of the day with these ridiculous panties on. He knew it was going to be torture, knew that every movement, every shift of his body, was going to remind him of his transgression, of his vulnerability.

He could feel the lace of the thong already rubbing against him, the sensation both irritating and arousing. He could feel the cool breeze against his exposed skin, the sensation sending shivers down his spine.

He made his way back to the office, his heart pounding in his chest, his mind racing. He knew they couldn't see the panties, but he felt like they could, like they could see right through his clothes and into his deepest, darkest desires.

He could feel the stares of his coworkers, their eyes lingering on him a little too long, and he knew they could see it - the outline of his cock straining against the cage, the panties doing little to hide it.

He took his seat at his desk, trying to focus on his work, but it was impossible.

Every rustle of fabric, every shift in his chair, reminded him of his predicament. He could feel the thong riding up, the lace tickling his ass, the cool breeze against his exposed skin. He tried to distract himself, to lose himself in his work, but it was no use. His mind was consumed by the sensation, by the constant reminder of his vulnerability.

He found himself daydreaming, imagining Mistress Sascha's response, her voice stern and commanding. "You're not to touch yourself, Jim.

Not until I say so." Mistress Sascha's words echoed in his mind, a constant reminder of his predicament. He tried to focus on his work, but it was proving to be an impossible task. Every rustle of fabric, every shift in his chair, reminded him of his exposed state, of the constant friction against his skin. He could feel the heat building between his legs, the pressure growing with each passing moment.

He tried to will his erection away, to no avail. It was as if his body had a mind of its own, responding to the stimulation, to the constant reminder of his vulnerability.

He could feel the blood rushing to his groin, his cock straining against the cage, the pressure growing unbearable. He clenched his fists, his nails digging into his palms, trying to distract himself, to focus on anything but the sensation.

But it was no use. He could feel the urge to climax building, the pressure in his groin growing more intense with each passing moment. He tried to hold it back, to fight it, but it was useless. He was going to come, right there in his seat, with nothing but a thin layer of fabric and a chastity cage between him and his release.

He couldn't let that happen, not here, not now. He had to find a way to relieve the pressure, to hold back until he was alone, until he could safely send Mistress Sascha a message and beg for her permission.

He stood up abruptly, his chair screeching against the floor, drawing the attention of his coworkers. He mumbled something about needing to use the restroom and hurried out of the office, his heart pounding in his chest.

He locked himself in the bathroom stall, leaning against the cold metal wall, his breath coming in ragged gasps.

He could feel the pressure in his groin, the urge to climax overwhelming. He knew he had to find a way to relieve the pressure, to hold back until he could safely send Mistress Sascha a message and beg for her permission.

He looked around the stall, his eyes landing on the roll of toilet paper. An idea began to form in his mind, a desperate, humiliating idea. He reached out, tearing off a long strip of toilet paper, the sound echoing in the small stall.

He lifted up the hem of his shirt, exposing his belly, the cool air sending a shiver down his spine.

He took a deep breath, steeling himself for what he was about to do. He couldn't believe he was actually considering this, but the pressure in his groin was too much, the urge to climax too overwhelming.

He wrapped the toilet paper around his hand, creating a makeshift barrier between his skin and the fabric of the panties. He reached down, his hand shaking as he slipped it under the waistband of the panties, the cool silk brushing against his fingers.

He could feel the heat radiating from his groin, the pressure in his balls almost unbearable. He gritted his teeth, forcing himself to hold back, to wait until he had some relief.

He wrapped his hand around his cock, the sensation of the chastity cage biting into his flesh a stark reminder of his predicament. He bit back a moan, his body tensing as he began to stroke himself, the friction of the cage and the toilet paper barrier sending jolts of pleasure through him.

He knew he shouldn't be doing this, knew that he was breaking the rules, but he couldn't help it. The pressure was too much, the urge too strong.

He pumped his fist, his breath coming in ragged gasps, his heart pounding in his chest. He could feel the orgasm building, the pressure in his groin growing more intense with each passing moment. He was so close, so fucking close.

But then, just as he was about to tip over the edge, he heard it - the sound of the bathroom door swinging open, the sound of footsteps echoing in the small room.

He froze, his heart leaping into his throat, his hand still wrapped around his cock.

"Jim?" a voice called out, the sound reverberating off the tile walls. It was Sarah, his coworker, her voice laced with concern. "Are you in here?"

Jim panicked, his mind racing as he tried to come up with a plan. He couldn't let her find him like this, couldn't let her see him with his hand down his pants, his cock straining against the chastity cage.

"Just a sec," he called out, his voice shaking as he tried to sound casual.

He quickly yanked his hand out of his pants, the sudden movement sending a jolt of pain through him as he inadvertently squeezed his trapped cock. He bit back a groan, using his other hand to quickly wipe the sweat from his brow.

"Is everything okay, Jim?" Sarah asked, her voice closer now. She must have been standing right outside the stall door.

"Yeah, yeah, I'm fine," he lied, his voice barely above a whisper. He couldn't let her find him like this, couldn't let her see him in this state of humiliation.

He quickly tucked himself back in, wincing at the discomfort, and flushed the toilet for good measure. He took a deep breath, trying to steady himself, before unlocking the stall door and stepping out.

Sarah was waiting for him, her arms crossed over her chest, a look of concern on her face. "Jim, are you sure you're okay? You've been acting strangely all day."

Jim felt the heat rise in his cheeks, his heart pounding in his chest. He knew he had to come up with a believable excuse, and fast. "Oh, uh, yeah, I'm fine, Sarah.

Just a bit of indigestion, you know how it is," Jim stammered, trying to sound casual as he washed his hands, avoiding her gaze in the mirror.

Sarah raised an eyebrow, clearly not convinced. "Indigestion, huh? You've been in here for quite a while. And you sounded... different when I came in."

Jim felt the color drain from his face, his mind racing. He had to think of something, anything to get her off his back. "Yeah, well, you know, sometimes it's... um... really bad. I had to, uh, take some medicine.

Strong stuff." Jim babbled, turning off the faucet and grabbing a handful of paper towels. He avoided Sarah's gaze, afraid she might see the truth hiding behind his eyes.

Sarah studied him for a moment, her expression unreadable. Then, to Jim's immense relief, she shrugged. "Well, if you're sure you're okay..."

"Yeah, I'm fine," Jim insisted, tossing the used towels into the bin and making for the door.

He needed to get out of there, needed to put some distance between himself and Sarah before she saw through his flimsy excuse.

"Alright," Sarah said, though she still seemed unconvinced. "But if you need anything, just let me know, okay?"

Jim nodded, managing a weak smile before escaping the bathroom. He leaned against the wall outside, closing his eyes and taking a deep breath. That had been too close. Too fucking close.

He could still feel the pressure in his groin, the urge to climax still lingering.

He knew he had to find a way to relieve the tension, but he also knew he couldn't risk getting caught again. He hurried back to his desk, his heart still pounding in his chest, his mind racing.

Jim glanced at the clock, realizing that it was almost time for his lunch break. He knew he needed to get out of the office, needed to find a place where he could be alone, where he could safely send Mistress Sascha a message and beg for her permission.

He grabbed his jacket and headed for the door, muttering something about going to grab lunch.

He could feel the stares of his coworkers on him, their eyes lingering a little too long, and he knew they could see it - the outline of his cock straining against the cage, the panties doing little to hide it. He could feel the heat rising in his cheeks, his heart pounding in his chest as he hurried out of the office.

He made his way to the park across the street, finding a secluded spot under a large oak tree. He sat down on the bench, his hands shaking as he pulled out his phone.

He knew he was breaking the rules, knew that he was risking Mistress Sascha's wrath, but he couldn't hold back any longer.

He tapped out a message, his fingers flying over the screen as he poured out his desperation. "Mistress Sascha, I can't hold back any longer. I need to come. Please, please give me permission."

He hit send, his heart pounding in his chest as he waited for her response.

He knew he was playing with fire, knew that he was risking her wrath, but he couldn't help it. The pressure in his groin was too much, the urge to climax too overwhelming.

His phone buzzed a moment later, her response swift and brutal. "Jim, you know better than this. You're not to touch yourself without my permission. And yet, here you are, begging for release like a pathetic little slut. I should deny you just for the principle of it."

Jim's heart sank, his stomach twisting into knots.

He had pushed too far, had broken the rules, and now he would have to face the consequences. He knew Mistress Sascha well enough to know that she wouldn't let this go unpunished.

"Please, Mistress Sascha," he typed out, his fingers trembling. "I'm sorry. I couldn't hold back. I need your forgiveness."

The three little dots appeared on the screen, indicating that she was typing a response. Jim held his breath, his heart pounding in his chest as he waited for her reply.

"Aww, poor little Jim," she finally responded, her tone dripping with mock sympathy.

"You think you deserve forgiveness just like that? You think you can break the rules and there won't be consequences?"

Jim felt a shiver run down his spine, a mix of fear and excitement stirring within him. He knew he was in for it now, but he also knew that he had brought this upon himself.

"No, Mistress Sascha," he typed out, his fingers trembling. "I deserve to be punished. I'm sorry for breaking the rules."

The three little dots appeared on the screen again, and Jim held his breath, waiting for her response. When it finally came, it was swift and brutal.

"Very well, Jim. Since you can't control yourself, I'll have to take matters into my own hands. For the next week, you'll wear a smaller, tighter chastity cage. And nothing but the tiniest thong and g-string panties, size small. And to remind you of your transgression, you'll wear a pair of clover clamps on your nipples for an hour each day."

Jim gasped, his eyes widening at the thought of the cruel devices pinching his sensitive flesh.

"Yes, Mistress Sascha," he managed to squeak out, his voice barely audible.

"Good boy," she replied, her tone laced with satisfaction. "And to make sure you remember your place, you'll address me as 'Mistress' at all times, both in person and in our messages. Understood?"

Jim felt a shiver run down his spine at the command, a mix of humiliation and excitement coursing through him. "Yes, Mistress," he whispered, his heart pounding in his chest.

"Very well," she said, her voice firm.

"And Jim, you're to wear those ridiculous pink panties for the rest of the day. I want you to feel every movement, every shift of fabric against your skin. I want you to be constantly reminded of your punishment, of your transgression. Do you understand?"

Jim swallowed hard, his heart pounding in his chest. "Yes, Mistress," he whispered, his voice barely audible.

"Good," she replied, her tone satisfied. "Now, get back to work. I expect you to be fully focused and productive.

Any slip-ups, and you'll find yourself with an even tighter cage and larger clamps. Is that understood, Jim?" Her voice was stern, leaving no room for argument.

Jim nodded, his heart still pounding in his chest. I'll be checking in on you later."

Jim took a deep breath, steeling himself for the rest of the day.

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