u/jjds500

Desire Key West - Part 2

Hey everyone! Glad everyone likes part one. I hope to keep them coming!

If you want to subscribe to the account in my bio for faster access!

The next morning James arrived early, exhausted and aching. The tiny pink steel cage had kept him in a state of constant, painful frustration all night. His balls were swollen and sore. He carried a bag containing every single item he had ever taken home.
Mrs. Allure was waiting for him alone in the front lounge. She closed the door and pointed to the chair opposite her.
“Sit down, James.”
He sat, face burning with shame. He opened the bag and laid everything out: the leather skirt, white blouse, latex bra, plugs, cock ring, ropes, and more.
“I’m sorry, Mrs. Allure,” he said quietly. “I broke every rule. I used the playroom when I wasn’t allowed. I even took things home with me. I’m returning all of it. I have no excuse.”
Mrs. Allure studied him for a long moment, then nodded. “Good. At least you’re honest about that much.”
James swallowed hard, remembering Mia’s strict instructions. His voice came out strained and humiliated. “And… I want to keep the cage on. I’ll pay for it. Whatever it costs. Please let me keep it.”
Mrs. Allure raised an eyebrow but agreed. “Very well. You will pay for the cage. From now on you will help out in the store however the girls need you. The others don’t need to know the full details. This stays between us for now.”
The Week in the Store
James’s days became a slow torture of desperation. He helped customers test gags, modeled latex and leather outfits for photos, and demonstrated restraints. Every movement made the tight cage bite into him. By Wednesday he was leaking constantly in his pants, shifting uncomfortably while helping a client try on a corset. Drew noticed and smirked but said nothing. By Thursday he was visibly flushed and distracted, his voice cracking when he spoke. Sydney commented once, “You seem… tense lately, James,” with a knowing look. He spent every lunch break in the bathroom trying (and failing) to get relief through the bars of the cage.
Every night after closing, Mia summoned him for their private sessions.
Night 1 – Anal Play & Boot Worship
Mia had him on his knees in the center of the playroom. “Start with my boots, thief. Show me how much you love them.”
James hesitated, but Mia grabbed his hair and pressed his face to her glossy pink leather thigh-high boots. He began kissing and licking them obediently while she watched with a cruel smile. “That’s it… worship them properly. I see how you stare at our boots all day. You don’t just want to look — you want to serve them, don’t you?”
He licked every inch — the toes, the insteps, the tall shafts — while she slowly turned, making him follow on his knees. After nearly thirty minutes of devoted boot worship, Mia bent him over the padded bench, wrists cuffed behind him.
She spent the next two hours on slow, teasing anal play. She started with her fingers, then moved to progressively larger plugs while the vibrating prostate massager buzzed against his spot. “You clench so greedily every time I push deeper,” she purred. “Listen to those pathetic little moans.”
Then she did something that made his mind spin. She slipped off one pink leather boot, still warm from her foot, and pressed the sharp stiletto heel against his entrance. “You love these boots so much… let’s see how much you can take.” She worked the heel inside him slowly, fucking him with it while the other boot stayed pressed against his face for continued worship. James gasped and whimpered around the leather, leaking heavily into the cage. “That’s right… take my heel like a good locked boy.” She never let him cum.
Night 2 – Pegging
Mia wore a thick strap-on. She made him drop to his knees first. “Suck it, James. Show me how much you want it.” He resisted, but she grabbed his hair and forced the silicone cock between his lips, making him gag and drool on it while she laughed. “Good boy… get it nice and wet for your ass.” Then she pegged him hard while slapping his locked cage. He came dry, ruined, and spent the rest of the night leaking and frustrated.
Night 3 – Impact Play
She bound him over a spanking bench and used a variety of paddles, crops, and a heavy flogger on his ass and thighs until he was shaking. Every strike made the cage bounce and leak more. “You’re dripping like a faucet,” Mia laughed. “Every time I hit you harder you throb in that tiny prison. You love the pain, don’t you?”
Night 4 – Wax Play
Mia lit several candles and dripped hot wax slowly across his chest, nipples, and locked cock while he was spread-eagled. The heat and sting made him hiss and arch. “Look at you leaking all over the wax,” she said with a cruel smile. “Your body is telling me things your mouth won’t.”
Night 5 – The Confession & Naked Tease
Mia had him tied spread-eagle. She edged him mercilessly for over an hour, then suddenly unlocked the cage. His cock sprang free, aching and purple. She stroked him slowly.
“Tell me what you really want, James. Be honest and I’ll let you cum.”
He resisted for nearly forty minutes, shaking his head. Mia kept teasing him about release, promising an orgasm if he told her the truth, edging him mercilessly. Every time he hesitated she triggered the shocking plug. Finally he broke.
“I… I want to be feminized,” he gasped. “I want the clothes, the body, the softness… I want to be turned into a girl. I’ve wanted it for years.”
Mia smiled viciously. She flipped him upside down in suspension, forced a ring gag into his mouth, and stroked him until he came hard — shooting straight into his own open mouth. James choked, repulsed and humiliated.
Then she surprised him completely. For the first time she slowly stripped completely naked in front of him. James had never seen any of them naked before. His eyes widened as she sat on the bench opposite him, spread her legs, and began slowly masturbating while maintaining eye contact. “Watch me cum, locked boy. This is what you’ll never get until I decide you’ve earned it.” She made a big show of it, moaning loudly, fingers moving faster until she came hard right in front of him, her body shuddering. James was left trembling, cage dripping again, mind reeling.
The next evening Mia surprised him. She had invited Sydney and Drew without warning. James was already bound tightly — armbinder, shocking plug still in, spreader bar.
Mia explained everything to them: “I’ve been holding his key the whole time. I caught him, locked him, and I’ve been using him every single night — anal with my heel, pegging, impact, wax, teasing… all of it. He’s my secret locked boy.”
Sydney’s eyes widened with genuine shock and delight. “Mia, you absolute bitch! You kept this delicious little secret all week? I’m impressed… and a little pissed you didn’t share sooner. But damn, this is hot.”
Drew looked both surprised and excited, her switch side clearly intrigued. “Wait — you’ve been playing with him every night and we had no idea? That’s actually really hot. I’m fine with it… but next time we’re all involved.”
Mia turned to James. “Tell them exactly what you admitted to me last night. What you really want and why.”
James hesitated. Mia triggered the shocking plug hard. He cried out and finally confessed in detail: “I want to be feminized… I want the clothes, the curves, the softness. I want to look pretty and be completely controlled. I’ve fantasized about it for years but was always too ashamed to say it.”
The three women reacted strongly.
Sydney grinned wide. “Holy shit. Our quiet little web designer wants to be a girl? That explains so much about how obsessed you are with our boots. You don’t just like them — you want to wear them, don’t you?”
Drew’s eyes lit up. “Oh my god, yes. That’s why you always stare at our legs. You want to be the one clicking around in tall patent boots and latex. That’s adorable… and incredibly hot.”
Mia laughed. “Exactly. He’s been leaking every time he sees our boots because he wants to be us.”
The three women spent the rest of the night discussing plans while James hung there, locked again, leaking, and deeply ashamed

reddit.com
u/jjds500 — 10 days ago

The Key - Part 1

Hey everyone, hope you enjoy my new story. More parts to come. For early access and all my other stories use the link in my bio!

Ethan sat alone at the far end of the sleek hotel lounge bar, slowly swirling the last of his scotch. At thirty, he looked every inch the polished traveling businessman — crisp white button-down with sleeves rolled to his elbows, navy trousers, loosened silver tie. He was in town for one night only.
Then she walked in.
Victoria commanded attention in her six-inch stiletto heels. Long raven-black hair, black leather corset cinching her waist dramatically, leather pencil skirt, and shiny black leather thigh-high boots that gleamed with every step. A small steel key dangled on a thin silver chain between her breasts.
Ethan’s eyes locked on that key immediately.
After building courage, he approached and bought her a drink. Their conversation flowed for nearly an hour, growing increasingly personal. Victoria noticed every glance at her boots and the key. Eventually she invited him up to room 312.
In her impeccably organized room, they shared wine, kissed, and clothes came off. She blindfolded him with his tie and locked thick padded leather cuffs behind his back.
Then she dropped the truth: “I’m a professional dominatrix.”
Before he could fully process it, she left to change, still in her commanding thigh-high boots. When she returned, she wore a stunning black leather corset, garter belt with sheer seamed stockings, long leather opera gloves, and those same glossy thigh-high stiletto boots.
Ethan’s cock stood painfully hard.
Victoria smiled. “Look at you… so eager. But we can’t get to the fun too quickly.”
She picked up two ice cubes from the wine bucket and dragged them slowly up and down his throbbing shaft. Ethan gasped sharply at the intense cold.
“Victoria… fuck, that’s freezing—”
“Shhh,” she whispered, circling the head of his cock with the melting ice. “Watch how fast your body obeys me.”
His erection shrank rapidly under the cold assault until he was completely soft and shrunken.
“Perfect,” she murmured.
From the nightstand she produced a small, heavy stainless-steel chastity cage. She carefully slipped the base ring behind his balls, stretching the sensitive skin.
“Victoria, wait — what are you doing?” he protested, voice rising.
She leaned over him, leather creaking, the small steel key swaying between her breasts. “This is exactly what you wanted, Ethan. You’ve been staring at my boots and this key all night long. You told me downstairs how you’ve never surrendered control… how the idea excites you. Look how hard you got just from the blindfold and cuffs. Your body already knows. This cage is going to keep you focused, desperate, and completely mine tonight. You’ll be so much more sensitive. When I finally unlock you, it’s going to feel incredible. This is what you came upstairs for.”
She worked the cold tube over his softened cock, pressing firmly until it clicked into place. With a final, decisive click of the lock, he was trapped. The key that had intrigued him all evening now hung around her neck, resting against her leather corset.
“No — wait, what the hell?” Ethan tugged hard at the cuffs, breathing fast. “This is too much. I didn’t agree to this.”
Victoria stroked the steel cage gently with one gloved finger. “You did, baby. The moment you bought me that drink and couldn’t stop staring. Deep down you’ve always wanted someone to take the decisions away. This is what you wanted. And you’re going to thank me for it very soon. I promise.”
Now the real teasing began.
Victoria took her time, savoring his helplessness. She started with a soft ostrich feather, trailing it slowly up and down his inner thighs, circling the base of the cage, then lightly brushing the exposed skin between the bars. Ethan twitched and gasped, the light touch driving him crazy.
“Feel that?” she purred. “So sensitive already. That’s what the cage does — it makes every single nerve ending desperate for attention.”
She set the feather aside and gave the cage a few firm, playful slaps with her gloved hand. The sharp smacks made the steel ring loudly against his body. Ethan groaned, hips bucking uselessly.
“Victoria… please…”
“Please what?” she teased, tugging gently on the key around her neck. “Please unlock you? Not a chance. Not yet. You look far too pretty like this.”
She leaned down and ran her warm tongue slowly along the steel bars of the cage, licking up the pre-cum that was already leaking steadily. The contrast between her hot mouth and the cold metal made Ethan moan loudly.
“Mmm, you taste so good when you’re denied,” she whispered, flicking her tongue against the tip. “Look at you leaking like a faucet. Does it hurt yet?”
“Yes… fuck, it aches,” he admitted, voice strained.
“Good,” she said sweetly. “That’s exactly how I want you.”
For the next fifteen minutes she tormented him relentlessly — alternating between gentle kisses and licks on the cage, sharp little pinches on his nipples, slow drags of her gloved fingernails down his thighs, and occasional firm tugs on the key hanging between her breasts. Every time he got close to the edge of frustration, she would pull back and laugh softly.
“You’re doing so well,” she cooed, stroking the locked cage with two fingers. “Straining so hard in that tiny prison. I can see how badly you want to get hard for me… but you can’t. Not until I say so.”
Ethan was breathing heavily, sweating, hips twitching desperately. “Victoria… I need… please…”
She finally removed the blindfold.
Ethan stared up at her in awe — the black leather corset, garter belt, stockings, long gloves, and those commanding thigh-high boots making her look like an untouchable goddess. The key still hung temptingly between her breasts.
“This isn’t so bad, is it?” she asked, smiling down at him.
Ethan swallowed hard. “It’s… intense. But yeah… not bad.”
Victoria sat on the edge of the bed, running a gloved hand along his thigh. “Good boy. So tell me, Ethan… what would you do for me right now?”
He hesitated, then answered honestly, voice shaky with arousal.
Victoria’s eyes sparkled. She reached into one of the neatly organized suitcases and laid several items on the bed beside him.
His eyes went wide.
A thick black strap-on harness.
A large steel butt plug.
A mean-looking braided leather whip.
“Well…” Ethan said uncertainly. “I don’t know about all that…”
Victoria leaned down, her leather creaking softly, and kissed his forehead.
“Well, let’s give it a try,” she whispered. “I think you’ll like it.”
To be continued

reddit.com
u/jjds500 — 10 days ago

The Key - Part 1

Hey everyone, hope you enjoy my new story! More parts to come. For quicker access use the link in my bio!

Ethan sat alone at the far end of the sleek hotel lounge bar, slowly swirling the last of his scotch. At thirty, he looked every inch the polished traveling businessman — crisp white button-down with sleeves rolled to his elbows, navy trousers, loosened silver tie. He was in town for one night only.
Then she walked in.
Victoria commanded attention in her six-inch stiletto heels. Long raven-black hair, black leather corset cinching her waist dramatically, leather pencil skirt, and shiny black leather thigh-high boots that gleamed with every step. A small steel key dangled on a thin silver chain between her breasts.
Ethan’s eyes locked on that key immediately.
After building courage, he approached and bought her a drink. Their conversation flowed for nearly an hour, growing increasingly personal. Victoria noticed every glance at her boots and the key. Eventually she invited him up to room 312.
In her impeccably organized room, they shared wine, kissed, and clothes came off. She blindfolded him with his tie and locked thick padded leather cuffs behind his back.
Then she dropped the truth: “I’m a professional dominatrix.”
Before he could fully process it, she left to change, still in her commanding thigh-high boots. When she returned, she wore a stunning black leather corset, garter belt with sheer seamed stockings, long leather opera gloves, and those same glossy thigh-high stiletto boots.
Ethan’s cock stood painfully hard.
Victoria smiled. “Look at you… so eager. But we can’t get to the fun too quickly.”
She picked up two ice cubes from the wine bucket and dragged them slowly up and down his throbbing shaft. Ethan gasped sharply at the intense cold.
“Victoria… fuck, that’s freezing—”
“Shhh,” she whispered, circling the head of his cock with the melting ice. “Watch how fast your body obeys me.”
His erection shrank rapidly under the cold assault until he was completely soft and shrunken.
“Perfect,” she murmured.
From the nightstand she produced a small, heavy stainless-steel chastity cage. She carefully slipped the base ring behind his balls, stretching the sensitive skin.
“Victoria, wait — what are you doing?” he protested, voice rising.
She leaned over him, leather creaking, the small steel key swaying between her breasts. “This is exactly what you wanted, Ethan. You’ve been staring at my boots and this key all night long. You told me downstairs how you’ve never surrendered control… how the idea excites you. Look how hard you got just from the blindfold and cuffs. Your body already knows. This cage is going to keep you focused, desperate, and completely mine tonight. You’ll be so much more sensitive. When I finally unlock you, it’s going to feel incredible. This is what you came upstairs for.”
She worked the cold tube over his softened cock, pressing firmly until it clicked into place. With a final, decisive click of the lock, he was trapped. The key that had intrigued him all evening now hung around her neck, resting against her leather corset.
“No — wait, what the hell?” Ethan tugged hard at the cuffs, breathing fast. “This is too much. I didn’t agree to this.”
Victoria stroked the steel cage gently with one gloved finger. “You did, baby. The moment you bought me that drink and couldn’t stop staring. Deep down you’ve always wanted someone to take the decisions away. This is what you wanted. And you’re going to thank me for it very soon. I promise.”
Now the real teasing began.
Victoria took her time, savoring his helplessness. She started with a soft ostrich feather, trailing it slowly up and down his inner thighs, circling the base of the cage, then lightly brushing the exposed skin between the bars. Ethan twitched and gasped, the light touch driving him crazy.
“Feel that?” she purred. “So sensitive already. That’s what the cage does — it makes every single nerve ending desperate for attention.”
She set the feather aside and gave the cage a few firm, playful slaps with her gloved hand. The sharp smacks made the steel ring loudly against his body. Ethan groaned, hips bucking uselessly.
“Victoria… please…”
“Please what?” she teased, tugging gently on the key around her neck. “Please unlock you? Not a chance. Not yet. You look far too pretty like this.”
She leaned down and ran her warm tongue slowly along the steel bars of the cage, licking up the pre-cum that was already leaking steadily. The contrast between her hot mouth and the cold metal made Ethan moan loudly.
“Mmm, you taste so good when you’re denied,” she whispered, flicking her tongue against the tip. “Look at you leaking like a faucet. Does it hurt yet?”
“Yes… fuck, it aches,” he admitted, voice strained.
“Good,” she said sweetly. “That’s exactly how I want you.”
For the next fifteen minutes she tormented him relentlessly — alternating between gentle kisses and licks on the cage, sharp little pinches on his nipples, slow drags of her gloved fingernails down his thighs, and occasional firm tugs on the key hanging between her breasts. Every time he got close to the edge of frustration, she would pull back and laugh softly.
“You’re doing so well,” she cooed, stroking the locked cage with two fingers. “Straining so hard in that tiny prison. I can see how badly you want to get hard for me… but you can’t. Not until I say so.”
Ethan was breathing heavily, sweating, hips twitching desperately. “Victoria… I need… please…”
She finally removed the blindfold.
Ethan stared up at her in awe — the black leather corset, garter belt, stockings, long gloves, and those commanding thigh-high boots making her look like an untouchable goddess. The key still hung temptingly between her breasts.
“This isn’t so bad, is it?” she asked, smiling down at him.
Ethan swallowed hard. “It’s… intense. But yeah… not bad.”
Victoria sat on the edge of the bed, running a gloved hand along his thigh. “Good boy. So tell me, Ethan… what would you do for me right now?”
He hesitated, then answered honestly, voice shaky with arousal.
Victoria’s eyes sparkled. She reached into one of the neatly organized suitcases and laid several items on the bed beside him.
His eyes went wide.
A thick black strap-on harness.
A large steel butt plug.
A mean-looking braided leather whip.
“Well…” Ethan said uncertainly. “I don’t know about all that…”
Victoria leaned down, her leather creaking softly, and kissed his forehead.
“Well, let’s give it a try,” she whispered. “I think you’ll like it.”
To be continued

reddit.com
u/jjds500 — 10 days ago

Desire Key West - Part 2

Hey everyone! Glad everyone likes part one. I hope to keep them coming!

If you want subscribe to the link in my bio for all the parts faster!

The next morning James arrived early, exhausted and aching. The tiny pink steel cage had kept him in a state of constant, painful frustration all night. His balls were swollen and sore. He carried a bag containing every single item he had ever taken home.
Mrs. Allure was waiting for him alone in the front lounge. She closed the door and pointed to the chair opposite her.
“Sit down, James.”
He sat, face burning with shame. He opened the bag and laid everything out: the leather skirt, white blouse, latex bra, plugs, cock ring, ropes, and more.
“I’m sorry, Mrs. Allure,” he said quietly. “I broke every rule. I used the playroom when I wasn’t allowed. I even took things home with me. I’m returning all of it. I have no excuse.”
Mrs. Allure studied him for a long moment, then nodded. “Good. At least you’re honest about that much.”
James swallowed hard, remembering Mia’s strict instructions. His voice came out strained and humiliated. “And… I want to keep the cage on. I’ll pay for it. Whatever it costs. Please let me keep it.”
Mrs. Allure raised an eyebrow but agreed. “Very well. You will pay for the cage. From now on you will help out in the store however the girls need you. The others don’t need to know the full details. This stays between us for now.”
The Week in the Store
James’s days became a slow torture of desperation. He helped customers test gags, modeled latex and leather outfits for photos, and demonstrated restraints. Every movement made the tight cage bite into him. By Wednesday he was leaking constantly in his pants, shifting uncomfortably while helping a client try on a corset. Drew noticed and smirked but said nothing. By Thursday he was visibly flushed and distracted, his voice cracking when he spoke. Sydney commented once, “You seem… tense lately, James,” with a knowing look. He spent every lunch break in the bathroom trying (and failing) to get relief through the bars of the cage.
Every night after closing, Mia summoned him for their private sessions.
Night 1 – Anal Play & Boot Worship
Mia had him on his knees in the center of the playroom. “Start with my boots, thief. Show me how much you love them.”
James hesitated, but Mia grabbed his hair and pressed his face to her glossy pink leather thigh-high boots. He began kissing and licking them obediently while she watched with a cruel smile. “That’s it… worship them properly. I see how you stare at our boots all day. You don’t just want to look — you want to serve them, don’t you?”
He licked every inch — the toes, the insteps, the tall shafts — while she slowly turned, making him follow on his knees. After nearly thirty minutes of devoted boot worship, Mia bent him over the padded bench, wrists cuffed behind him.
She spent the next two hours on slow, teasing anal play. She started with her fingers, then moved to progressively larger plugs while the vibrating prostate massager buzzed against his spot. “You clench so greedily every time I push deeper,” she purred. “Listen to those pathetic little moans.”
Then she did something that made his mind spin. She slipped off one pink leather boot, still warm from her foot, and pressed the sharp stiletto heel against his entrance. “You love these boots so much… let’s see how much you can take.” She worked the heel inside him slowly, fucking him with it while the other boot stayed pressed against his face for continued worship. James gasped and whimpered around the leather, leaking heavily into the cage. “That’s right… take my heel like a good locked boy.” She never let him cum.
Night 2 – Pegging
Mia wore a thick strap-on. She made him drop to his knees first. “Suck it, James. Show me how much you want it.” He resisted, but she grabbed his hair and forced the silicone cock between his lips, making him gag and drool on it while she laughed. “Good boy… get it nice and wet for your ass.” Then she pegged him hard while slapping his locked cage. He came dry, ruined, and spent the rest of the night leaking and frustrated.
Night 3 – Impact Play
She bound him over a spanking bench and used a variety of paddles, crops, and a heavy flogger on his ass and thighs until he was shaking. Every strike made the cage bounce and leak more. “You’re dripping like a faucet,” Mia laughed. “Every time I hit you harder you throb in that tiny prison. You love the pain, don’t you?”
Night 4 – Wax Play
Mia lit several candles and dripped hot wax slowly across his chest, nipples, and locked cock while he was spread-eagled. The heat and sting made him hiss and arch. “Look at you leaking all over the wax,” she said with a cruel smile. “Your body is telling me things your mouth won’t.”
Night 5 – The Confession & Naked Tease
Mia had him tied spread-eagle. She edged him mercilessly for over an hour, then suddenly unlocked the cage. His cock sprang free, aching and purple. She stroked him slowly.
“Tell me what you really want, James. Be honest and I’ll let you cum.”
He resisted for nearly forty minutes, shaking his head. Mia kept teasing him about release, promising an orgasm if he told her the truth, edging him mercilessly. Every time he hesitated she triggered the shocking plug. Finally he broke.
“I… I want to be feminized,” he gasped. “I want the clothes, the body, the softness… I want to be turned into a girl. I’ve wanted it for years.”
Mia smiled viciously. She flipped him upside down in suspension, forced a ring gag into his mouth, and stroked him until he came hard — shooting straight into his own open mouth. James choked, repulsed and humiliated.
Then she surprised him completely. For the first time she slowly stripped completely naked in front of him. James had never seen any of them naked before. His eyes widened as she sat on the bench opposite him, spread her legs, and began slowly masturbating while maintaining eye contact. “Watch me cum, locked boy. This is what you’ll never get until I decide you’ve earned it.” She made a big show of it, moaning loudly, fingers moving faster until she came hard right in front of him, her body shuddering. James was left trembling, cage dripping again, mind reeling.
The next evening Mia surprised him. She had invited Sydney and Drew without warning. James was already bound tightly — armbinder, shocking plug still in, spreader bar.
Mia explained everything to them: “I’ve been holding his key the whole time. I caught him, locked him, and I’ve been using him every single night — anal with my heel, pegging, impact, wax, teasing… all of it. He’s my secret locked boy.”
Sydney’s eyes widened with genuine shock and delight. “Mia, you absolute bitch! You kept this delicious little secret all week? I’m impressed… and a little pissed you didn’t share sooner. But damn, this is hot.”
Drew looked both surprised and excited, her switch side clearly intrigued. “Wait — you’ve been playing with him every night and we had no idea? That’s actually really hot. I’m fine with it… but next time we’re all involved.”
Mia turned to James. “Tell them exactly what you admitted to me last night. What you really want and why.”
James hesitated. Mia triggered the shocking plug hard. He cried out and finally confessed in detail: “I want to be feminized… I want the clothes, the curves, the softness. I want to look pretty and be completely controlled. I’ve fantasized about it for years but was always too ashamed to say it.”
The three women reacted strongly.
Sydney grinned wide. “Holy shit. Our quiet little web designer wants to be a girl? That explains so much about how obsessed you are with our boots. You don’t just like them — you want to wear them, don’t you?”
Drew’s eyes lit up. “Oh my god, yes. That’s why you always stare at our legs. You want to be the one clicking around in tall patent boots and latex. That’s adorable… and incredibly hot.”
Mia laughed. “Exactly. He’s been leaking every time he sees our boots because he wants to be us.”
The three women spent the rest of the night discussing plans while James hung there, locked again, leaking, and deeply ashamed

reddit.com
u/jjds500 — 11 days ago

Sofia’s Eventful Night - Part 1

Hey everyone! Please bear with me! For more stories use the link in my bio for more! Enjoy! ALL CHARACTERS ARE FICTIONAL AND CONSENTING TO THE SCENE.

Sophia had been planning this for weeks. Tonight was supposed to be her ultimate self-bondage session — risky, intense, and completely private. She stood in front of her full-length mirror, admiring how incredible she looked.
She wore a scandalously sexy black lace babydoll that was nearly see-through, the cups barely containing her full, heavy breasts. A matching garter belt cinched her waist, clipping onto sheer black thigh-high stockings. On her feet were glossy patent leather thigh-high boots with six-inch stiletto heels that made her legs look endless and her ass impossibly perky. Crotchless panties left her shaved pussy and tight ass completely exposed.
She had lubed and slowly worked two thick vibrating dildos into herself. The larger one stretched her pussy deliciously, its ridged surface pressing perfectly against her G-spot. The slightly smaller but equally powerful one filled her ass, already buzzing on a low, teasing setting. Both were remote-controlled, though she had hidden the remote under the edge of the mattress.
Next came the restraints. She buckled thick leather cuffs around her wrists and ankles. A heavy ball gag — bright red, two inches wide — was strapped tightly into her mouth, forcing her jaw open and causing drool to already trickle down her chin. The padded leather blindfold plunged her into total darkness.
For the finale, she had set up an intricate hogtie. She connected her ankle cuffs to a rope that ran to the headboard, then used ice locks on her wrist cuffs behind her back. The ice was supposed to melt in about 25–30 minutes, releasing the quick-release knots and freeing her. A final rope pulled her wrists and ankles closer together, arching her back and forcing her ass high in the air.
She had tested everything… except the ice locks in this exact position.
The moment she clicked the last lock shut and rolled onto the bed, disaster struck. The rope tension was far tighter than she anticipated. One of the ice locks jammed against the bedframe, refusing to drop. The knots she had counted on became impossible to reach. Now she was helplessly hogtied in the center of her bed — ass up, thighs spread wide, boots gleaming, two powerful vibrators buzzing relentlessly inside her dripping holes.
“Mmmph…!” she moaned desperately into the gag. The vibrations quickly built. Within minutes she was shuddering through her first orgasm, pussy clenching hard around the thick toy while drool poured from her gagged mouth. Another wave hit soon after. Time blurred. Her body trembled uncontrollably as the toys continued their merciless assault, pushing her from one helpless climax to the next. She had no idea how long she’d been stuck like this — twenty minutes? Forty? Her mind was hazy with overstimulation.

Ryan pushed open the apartment door, loosening his tie after another brutal twelve-hour shift. “Sophia? You still up?”
Silence… except for faint, rhythmic, muffled moans coming from down the hall.
His curiosity turned to shock the second he cracked open her bedroom door.
There she was — his gorgeous roommate, dressed like every wet dream he’d ever had. Shiny thigh-high boots, lace lingerie, perfect ass raised high, two buzzing toys visibly stretching her holes. Ball gag, blindfold, leather cuffs, helpless hogtie. She looked like pure, filthy perfection.
“Jesus Christ, Sophia…” Ryan whispered, his cock surging to full hardness instantly. “You did all this… for me?”
He stepped inside, closing the door behind him. Sophia jerked at the sound of his voice, letting out a surprised, gagged cry. Ryan took it as excitement.
“You’ve been fantasizing about me finding you like this, haven’t you?” he murmured, voice thick with lust. He ran his hands slowly up the backs of her thigh-high boots, feeling the smooth, warm leather. “All tied up and waiting for your roommate to come home and fuck you senseless. Such a naughty little slut.”
Sophia tried to shake her head frantically and protest through the gag, but it only came out as a desperate, drooling “Mmmphhh!” that sounded exactly like a moan of need.
Ryan climbed onto the bed behind her. He gripped the base of the vibrating dildo in her pussy and slowly pulled it out with a wet pop, watching her hole clench and drip. He replaced it with two thick fingers, curling them against her G-spot.
“Fuck, you’re soaked,” he groaned. “This is the best surprise ever.”
He freed his rock-hard cock and rubbed the swollen head up and down her dripping slit before thrusting deep inside her in one smooth motion. Sophia screamed into the gag as he filled her completely, the anal vibrator still buzzing strongly against his cock.
Ryan started fucking her with long, deep strokes, hands gripping her bound hips. The sound of his hips slapping against her ass mixed with the wet squelching of the toys and her constant muffled moans. He reached under her and pinched her swinging breasts, twisting her nipples while he pounded her harder.
“You feel so fucking good,” he growled, spanking her ass sharply. “I’ve jerked off thinking about you so many times. Now here you are — gift-wrapped for me.”
Sophia’s body betrayed her again and again. Another shattering orgasm ripped through her, making her clench violently around his cock as she thrashed in the ropes. Ryan kept thrusting through it, lost in pure lust.
But as he slowed down for a moment to savor the feeling, he finally noticed the details he’d missed in his haze of arousal: the ice lock that hadn’t melted, the jammed rope, the remote control lying just out of reach, the way her struggles looked genuinely desperate rather than playful.
His blood ran cold.
“Oh… shit.” He froze mid-thrust. “Sophia… this wasn’t for me, was it? You’re actually stuck. This was self-bondage and something went wrong.”
Sophia nodded frantically, tears of humiliation and exhaustion soaking the blindfold.
“Fuck. I’m so sorry,” Ryan whispered, voice full of genuine panic. He quickly pulled out of her and started working on the ropes. “I thought… God, I’m such an idiot. Hold on, I’ll get you out right now.”
He carefully removed the ice lock, untied the hogtie ropes, and freed her wrists and ankles. Sophia collapsed onto the bed, trembling, the two vibrators still buzzing inside her exhausted body.
Ryan gently removed the blindfold. Her eyes were red, mascara streaked. He reached behind her head and unbuckled the ball gag.
The moment the gag slipped from her mouth, Sophia took a deep, shaky breath. She slowly pushed herself up on her elbows, still wearing the soaked lingerie and thigh-high boots, toys still buried inside her.
She turned her head and glared at him with pure, murderous daggers in her eyes.

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u/jjds500 — 11 days ago

Jenny’s Happy Accident

Jenny’s bedroom was a chaotic little sanctuary in the four-bedroom apartment she shared with her three guy roommates. Posters of indie bands and travel destinations covered the pale blue walls. String lights hung lazily across the ceiling, casting a soft pink glow over the unmade queen bed piled with rumpled sheets and a few stray socks. Her desk was buried under textbooks she’d sworn she’d never open again, now mixed with empty coffee cups and a half-eaten bag of chips. A full-length mirror leaned against the closet door, reflecting the scene back at her.
At twenty-three, fresh out of college with a degree in marketing and zero idea what to do next, Jenny was the definition of “skinny blonde bombshell.” Five-foot-four, barely a hundred and ten pounds, with long, straight platinum-blonde hair that fell down her back like silk. Her skin was smooth and pale, her small perky breasts tipped with soft pink nipples that were currently rock-hard. A tiny waist flared into slim hips and a tight, heart-shaped ass. She was completely naked except for the thick black leather collar buckled snugly around her throat.
She loved the way it felt.
Lying on her back in the middle of the bed, legs spread wide, Jenny pressed the thick, buzzing vibrator harder against her swollen clit. The collar’s firm, unyielding embrace hugged her neck with every breath, a constant reminder of submission that made her pussy throb. God, I love how tight it is, she thought, eyes half-closed. Like someone’s hand wrapped around my throat, owning me. She imagined strong fingers tightening it just a little more as she moaned softly.
The vibrator hummed on high. She slid two fingers inside herself, curling them against her G-spot while the toy buzzed relentlessly against her clit. Her hips rocked upward, chasing the building pressure.
Fuck… I want them. All three of them. At the same time.
The thought hit her like lightning. Alex, Ben, and Chris — her ridiculously hot roommates.
Alex was the tall one, six-foot-two, broad-shouldered with dark messy hair and a jaw you could cut glass on. He worked out constantly and always walked around shirtless, showing off the deep V-lines that disappeared into his sweatpants.
Ben was the blond surfer type — lean, athletic swimmer’s build, golden skin, easy smile, and bright blue eyes that made her knees weak.
Chris was the rugged one: heavily tattooed across his chest and arms, broad shoulders, thick muscular thighs, and a deep voice that rumbled when he laughed.
Jenny’s mind spiraled. I want them to walk in and find me like this — collared, dripping, desperate. I want Alex to grab my hair and shove his thick cock down my throat while Ben rails my pussy and Chris takes my ass. I want to be passed around like their little fucktoy, used, filled, covered in their cum…
Her breathing quickened. She was right on the edge.
The front door of the apartment banged open.
“Hey, we’re home!” Alex’s deep voice called out.
“Anyone want pizza?” Ben added, kicking off his shoes.
Chris laughed. “I’m starving. Long-ass day at the site.”
Jenny’s eyes flew open. They were early — way early. She was right on the brink, vibrator still pressed hard against her clit, fingers buried inside her soaked pussy. The orgasm crashed over her like a tidal wave.
“Oh fuck—!” she whimpered, biting her lip to stay quiet as her whole body convulsed. Her pussy clenched rhythmically around her fingers, juices soaking the sheets. The collar felt even tighter as she arched her back, thighs shaking violently. It was the most intense orgasm of her life. She kept the vibrator going through every pulsing wave, riding it out while the guys chatted casually in the living room just twenty feet away.
They have no idea I’m in here cumming my brains out thinking about them destroying me.
She finally switched the toy off, chest heaving, body limp and glowing. Her mind was still spinning with filthy fantasies.
Then her phone buzzed on the nightstand.
She grabbed it with shaky fingers and opened the group chat with the guys. Without thinking, she snapped a quick mirror selfie — completely naked, collar on, legs still spread, pussy visibly glistening, a blissed-out look on her flushed face. She typed fast:
Jenny: God, my roommates are all so hot. I wish I could sleep with them.
She hit send.
The apartment went dead silent.
Jenny’s eyes widened in horror as she realized what she’d done.
“Oh my god… wrong chat… wrong chat…” she whispered.
The guys’ voices dropped to low murmurs in the living room. She could just barely hear them.
Alex: “Holy shit… did you guys see that?”
Ben: “She’s… collared? And naked? Jesus.”
Chris: “She wants us? All of us?”
Jenny’s heart hammered. She quickly typed:
Jenny: Oh my god. Wrong chat. You guys weren’t supposed to see that.
She threw on an oversized t-shirt and tiny sleep shorts, no bra, no panties, and stepped out of her room on shaky legs.
The three guys were standing in the living room, all of them clearly trying (and failing) to hide their erections.
Alex — tall, dark-haired, wearing a tight black t-shirt that stretched across his muscular chest and gray sweatpants that did nothing to hide the thick bulge running down his thigh — stared at her with dark, hungry eyes.
Ben — blond, toned, in a fitted white tank top and basketball shorts — had a visible tent and flushed cheeks.
Chris — broad, tattooed, in a black compression shirt and gym shorts — adjusted himself openly, a smirk playing on his lips.
Jenny’s face burned bright red. “Oh my god, I’m so sorry. I’m so sorry. That was an accident. I didn’t mean—”
Alex cut her off, voice low. “You sure about that, Jen?”
Jenny’s gaze dropped involuntarily to the three very obvious hard cocks straining against their clothes. A fresh wave of heat flooded between her legs.
She swallowed hard, then smiled shyly.
“Well… you know, we always could.”
The silence lasted half a second.
Then all three guys moved at once.
Jenny led them back to her room, heart pounding with excitement. Clothes hit the floor in seconds. Alex was huge — thick, veined, at least eight inches, already leaking pre-cum. Ben was long and perfectly straight, smooth and pretty. Chris was girthy, heavy, with a slight upward curve and a fat head that made her mouth water.
They didn’t waste time.
Alex pulled her in first, kissing her hard while his hands roamed her naked body, fingers tugging on the collar. “Fuck, this collar looks good on you,” he growled. Ben dropped to his knees behind her, spreading her ass cheeks and licking her pussy from behind in long, hungry strokes. Chris stood beside them, stroking his thick cock.
Jenny moaned into Alex’s mouth as Ben’s tongue worked her clit. “Yes… fuck, I’ve wanted this so bad…”
They moved her to the bed. Alex lay back and pulled her on top, sliding his thick cock into her soaked pussy in one smooth thrust. Jenny cried out loudly, the stretch delicious and overwhelming. Ben knelt in front of her face and fed her his long cock, pushing deep until she gagged. Chris moved behind her, lubing his thick shaft before pressing it against her tight ass.
“Oh god… yes… fill me up,” Jenny gasped around Ben’s cock, voice already rising.
Chris pushed in slowly, the double penetration making her eyes roll back. They found a rhythm — Alex thrusting up into her pussy, Chris pounding her ass, Ben fucking her mouth. The sounds were obscene: wet slapping skin, muffled moans, the creak of the bed.
But Jenny was loud. Very loud.
“Fuck— harder— yes—!” she screamed between thrusts.
Alex grabbed her hair and pulled her off Ben’s cock for a second. “You’re gonna wake the whole building, baby. Open wide.”
Chris reached into her nightstand (he’d clearly noticed the collar earlier) and pulled out a bright red ball gag. He buckled it tightly behind her head, forcing her jaw open. “There. Now you can scream all you want, slut.”
The gag turned her moans into wet, desperate gurgles. They resumed with renewed intensity, passing her around like their personal toy.
Alex flipped her onto all fours so Chris could take her pussy while Ben fucked her throat. Chris spanked her ass hard with every thrust, leaving red handprints. “Look at this tight little cunt swallowing my cock,” he groaned. “She’s dripping everywhere.”
Ben held her head down, fucking her face. “Good girl. Take it all. That collar looks even better when your eyes are watering.”
They rotated again. Ben lay on his back and pulled Jenny on top in reverse cowgirl, sliding into her pussy while Alex straddled his legs and pushed into her ass. The double penetration stretched her to the limit. Chris stood in front of her, feeding his thick cock past the ball gag, using the straps to control her head.
Jenny’s mind was pure bliss. I’m being used by all three of them at once. Filled in every hole. This is everything I fantasized about. Her body shook with another orgasm, pussy clenching hard around Ben while the gag muffled her screams.
They kept going for what felt like forever — switching positions, spanking her, tugging the collar, whispering filthy praise.
“Such a perfect little collared whore,” Alex grunted, pounding her from behind while Ben and Chris took turns in her mouth.
“She loves being passed around,” Chris laughed, slapping her tits lightly. “Look how wet she is.”
Ben pulled out of her mouth just long enough to say, “Our little fucktoy now. Every night.”
Finally, they lined up in front of her on the bed. Jenny was on her knees, gag still in, collar tight around her throat, body covered in sweat and marks. They stroked themselves furiously.
One by one they came — thick ropes of cum painting her face, tits, and tongue. Alex finished first, groaning as he shot across her cheeks. Ben followed, covering her perky breasts. Chris last, pushing deep past the gag and filling her mouth until it overflowed.
Jenny swallowed what she could, eyes glassy with satisfaction, the ball gag still muffling her happy whimpers.
The guys collapsed around her, breathing hard.
Alex reached over and gently unbuckled the gag. “You okay, Jen?”
Jenny smiled dreamily, licking her lips. “Best accident ever

reddit.com
u/jjds500 — 11 days ago

Caught in Shiny Submission

To see more stories and the next parts see the link on my other posts!

Part 1.

James’s heart pounded wildly as he made one final check of every restraint. He stood trembling in front of the full-length mirror, completely transformed into the perfect latex slut. The glossy black latex catsuit hugged every curve of his body like a second skin, shiny and tight, squeezing his chest and ass into exaggerated feminine proportions. Shiny black patent-leather thigh-high boots with six-inch stilettos encased his legs, forcing him onto his toes and making his calves burn with that delicious, helpless ache.
A feminine latex hood with plump red cock-sucking lips and a high ponytail was zipped tightly over his head, leaving only his wide, nervous eyes visible. A thick red ball gag was strapped deep behind those molded lips, filling his mouth and turning every breath into a wet, pathetic whimper. Beneath the latex, his cock was locked in a cruel pink steel chastity cage — tiny, curved, and merciless. The key dangled from a small timer lock he had set for forty-five minutes.
He had gone all out. His wrists were locked behind his back in a heavy leather armbinder, elbows crushed painfully together. A spreader bar forced his booted legs wide apart. A thick rope ran from the D-ring on the armbinder to a ceiling hook, holding him bent forward at a strict ninety-degree angle, ass pushed out and perfectly presented. The timer was supposed to drop the key into reach… but the ice had jammed. He was truly stuck. Helpless. Dripping.
“Mmmphhh…” James moaned into the gag, the sound high and feminine. The chastity cage kept him throbbing in denial, pre-cum leaking steadily through the tiny slit.
The front door of the apartment clicked open.
“James? You home already?” called Lila, his roommate. She had finished her shift early.
Footsteps came down the hallway. The bedroom door swung open.
Lila stopped dead in the doorway, eyes going wide at the sight: her roommate bent over in full shiny latex, thigh-high boots spread obscenely wide, hooded and gagged, caged cock hanging and dripping. A slow, predatory smile spread across her face.
“Oh… fuck,” she whispered, stepping inside and locking the door behind her. “James… or should I say Jamie? Look at you, all dressed up like the sluttiest little latex whore I’ve ever seen. Stuck in your own self-bondage trap. I always suspected you were a secret sissy, but this is beyond my wildest dreams.”
She circled him slowly, her fingers trailing over the squeaking latex covering his ass and down the shiny thigh-high boots. James whimpered and tried to shake his head, but the rope and armbinder held him perfectly immobile.
Lila crouched in front of his hooded face, lifting his chin with one finger. “Aww, poor trapped little girl. That tiny pink cage looks so tight and painful. How long have you been locked up, leaking like a desperate bitch in heat?” She flicked the cage sharply with her fingernail, making him jerk and moan. “You want release, don’t you? Want me to tease that key and maybe… just maybe… let you cum?”
She stood up, retrieved the timer key from the floor where it had fallen just out of reach, and dangled it teasingly in front of his eyes. “Look at this. So close, yet so far. Beg for it with those pretty eyes, sissy.” She slipped the key into her pocket and unzipped the back of his catsuit all the way down, fully exposing his ass. “But first, I think you need to earn it.”
Lila disappeared for a moment, then returned wearing a thick, veined eight-inch strap-on dildo buckled tightly around her hips. She lubed it generously while staring at him.
“You’re going to take every inch like a good girl,” she purred, pressing the fat head against his tight hole. “And if you’re lucky, I might unlock that pathetic little clit afterward.”
James whimpered frantically as she pushed forward, slowly stretching him open. The thigh-high boots made his legs tremble, the armbinder kept his shoulders aching, and the hood and gag turned all his protests into muffled, slutty moans. Lila sank the strap-on deep inside him in one long thrust, then started fucking him with steady, powerful strokes.
“That’s it, Jamie. Take my cock,” she moaned, spanking his latex-covered ass hard. “Look at you — fully feminized, locked in chastity, bent over and pegged like the whore you were born to be. I’m never letting you live this down.”
She reached around and teasingly stroked the outside of the chastity cage while pounding him faster. “So much pre-cum. You’re loving this, aren’t you? My helpless little latex fucktoy.”
James’s mind was a whirlwind of humiliation and overwhelming pleasure. The strap-on hammered his prostate relentlessly. His caged cock leaked uncontrollably. Lila fucked him harder, moaning with her own pleasure as the base of the dildo ground against her clit.
“You’re going to cum in that tiny cage while I fuck you,” she growled. “Right now.”
She slammed deep and rubbed the cage firmly. James screamed into the gag as a shattering, ruined orgasm ripped through him — cum spurting weakly through the slit of the pink cage onto the floor while Lila came hard behind him, moaning loudly.
She stayed buried inside him for a long moment, catching her breath, then slowly pulled out. James hung limply in the ropes, trembling, utterly spent and humiliated.
Lila patted his hooded cheek and smiled sweetly. “Good girl. Now… about that key. We’re going to have a lot more fun before I even think about unlocking you.”

reddit.com
u/jjds500 — 11 days ago

Desire Key West

Part 1: The Slow Seduction
James had fled New York’s gray grind six weeks earlier, drawn to Key West by sun, salt, and the promise of something freer. Cash was tight, so when the ad appeared — “Web designer for upscale fetish boutique. Immediate start. High pay. Absolute discretion required.” — he jumped at it.
Mrs. Allure replied personally. The interview at Desire left him breathless.
The boutique was a restored pink conch house off Duval — elegant, discreet, with frosted windows and a small gold plaque. Mrs. Allure greeted him in a white linen blouse open low over a black latex corset, a supple black leather pencil skirt, and gleaming thigh-high patent leather boots with six-inch chrome heels.
Inside was pure high-fashion fetish: racks of latex and leather, steel toys displayed like art, and a discreet soundproofed playroom at the back with padded leather benches, mirrors, hooks, and shelves of ropes and toys. “Clients test items here,” Mrs. Allure explained coolly. “You are not to use it. Ever. The merchandise is strictly off-limits after hours. Understood?”
James nodded. He understood.
The saleswomen were intoxicating.
Sydney — tall raven-haired in blood-red latex with structured leather corsetry and laced thigh-high leather boots.
Drew — curvy blonde in a white leather blouse unbuttoned low over a black latex bra, tight black leather pencil skirt, and glossy black patent mid-thigh boots.
Mia — petite brunette in a short pink latex dress with delicate leather straps and matching pink leather thigh-high boots. She was the most dangerous — a true sadist with a sweet smile and wicked eyes.
From his very first week, Mia began flirting. Sly little comments when no one else could hear.
“Careful around the leather, James… it has a way of making people want to misbehave.”
“You look like you’d fill out one of Drew’s skirts nicely.”
“Night shift must get lonely… if you ever need someone to test a blindfold on you, I’m very gentle.”
On the evening of his second week, after the last customer left, Mrs. Allure insisted they all stay for drinks in the front lounge. Rum cocktails were poured. The conversation turned playful and probing.
The girls pestered James about his sex life. “So, James,” Drew asked with a smirk, “what’s a cute guy like you into down here? Any wild stories yet?”
Sydney leaned in. “Yeah, spill.”
Mia tilted her head sweetly. “Come on… don’t be shy.”
James shifted uncomfortably. “Honestly? Not much. I haven’t really met many people yet. Work and settling in have kept me busy. My last relationship was pretty vanilla… nothing exciting.”
The girls shared freely, their lives wildly different.
Sydney laughed. “I’m a switch. I love threesomes and meeting people out, switching roles for each scene. Keeps things exciting.”
Drew grinned. “I’m a loving dom. I only pick guys up to peg them and make them realize that true joy is from being used properly by a girl. Most fight it at first… then thank me later.”
Mia’s eyes sparkled with dark delight. She reached into her purse and pulled out a small keyring heavy with at least a dozen tiny keys, dangling it in front of everyone. “I’m a sadist. I love picking guys up at bars, bringing them back here or to my place, and locking them in chastity. They leave completely denied and desperate, then have to beg me to release them when they have to fly home. I make them pay extra or do something truly humiliating before I unlock them. Watching them break is my favorite part.”
James felt a strong wave of repulsion twist in his stomach. Being locked up and forced to beg? That sounds like a nightmare, he thought. No way I’d ever let anyone do that to me. The idea disgusted him deeply.
Later in the conversation James admitted, “I did get tied up once with a belt by my ex. It was okay, I guess. She wanted to stick a finger in my butt but I said no.”
The girls reacted immediately.
Sydney smirked. “A belt? Cute. You should have let her. Anal can be amazing if done right.”
Drew smiled warmly. “A lot of guys discover they love it once they try it properly. I would have made it feel good for you.”
Mia’s sadistic grin widened. “You said no? How adorable. I would have made you beg for it… and then done it anyway while you were locked and helpless.”
James felt even more uneasy but kept his face neutral.
He finished his drink and left early.
As soon as the door closed behind him, the girls gossiped.
Sydney smirked. “He’s definitely curious.”
Drew laughed. “Poor thing has no idea what he’s walking into.”
Mia just smiled darkly. “Leave him to me… I’m going to enjoy this one.”
For the next several nights the temptation grew. James started sneaking clothing and toys home. One night he tried on a black leather pencil skirt and patent boots while watching kinky porn. Another night he wore the white leather blouse and latex bra, stroking himself to videos of sadistic women. The fantasies consumed him.
By night nineteen the ache was unbearable.
The breaking point came on the twentieth night — a raging tropical storm.
Mrs. Allure and the girls left early for a private party. James locked the front door, heart hammering. He slipped into the playroom, dimmed the red lights, and stripped.
He chose Drew’s style: crisp white leather blouse unbuttoned low, glossy black latex bra, tight black leather pencil skirt, glossy black patent mid-thigh boots. He added the locking leather collar and wrist cuffs.
He lubed the thick vibrating plug with rotating head and worked it deep inside himself, turning it on low. He snapped the tight black cock ring on. Then he gagged himself with a thick penis gag, buckling it tightly. Finally he rigged the standing self-bondage — wrists clipped high, ankles locked to floor rings. The last carabiner clicked… and he realized the safety release was out of reach. He was helplessly stuck, blindfolded, gagged, plugged, ringed, and dressed in stolen merchandise.
Mia returned first — she had forgotten her phone. She stepped in and let out a low, delighted laugh.
“Ohhh, James…” she purred, circling him. “Look at you. All dressed up in Drew’s favorite leather like a little thief. Blindfolded. Gagged with a cock in your mouth. Plugged and ringed and completely stuck. Did you really think no one would find you?”
James made a muffled, angry sound.
Mia’s voice stayed sweet for now. “Mmm, that plug is buzzing so nicely inside you. You’re going to look so good locked up just like the others I play with. You’ll be joining my little collection of denied boys.”
James shook his head frantically, trying to protest around the gag.
Mia stroked the leather skirt over his straining cock. “Oh yes you will. Beg for it, James. Beg me to let you cum. I want to hear you moan like the desperate little rule-breaker you are.”
James resisted, but the plug kept swirling and vibrating. Mia edged him mercilessly for long minutes.
“Beg,” she whispered, voice turning darker. “Beg like you mean it or I leave you here all night.”
Finally James broke and moaned desperately around the gag, nodding frantically.
Mia laughed. “Good boy. Cum for me.”
She sucked him hard while the plug buzzed on high. James came explosively, shaking in the ropes.
The second he finished, Mia’s sweet mask dropped. Her tone turned cold, cruel, and viciously sadistic.
“You pathetic little shit,” she hissed. “You actually begged me to make you cum while breaking every rule. Disgusting.”
She pulled the penis gag from his mouth, coated it thickly in the cum still on her fingers and lips, and forced it back between his teeth, buckling it even tighter. “There. Now you can taste yourself, thief.”
James tried to protest, but the cum-coated gag muffled him.
Mia grabbed the tiny pink steel cage. James immediately started thrashing, twisting his hips away. “No— fuck you— get that thing off me!”
Mia laughed meanly, squeezed his balls until he yelped, and forced the brutally small, tight cage down over his softening cock while he fought her every inch. The steel crushed him painfully. She locked it with a loud click.
“You’re staying locked for me now, James. Our dirty little secret. The others will think you did this yourself. Tell them the key is at home. If you tell them the truth, these pictures go everywhere and you lose your job.”
Mia called the others. “Come back — James locked himself up in the playroom. You have to see this.”
When Mrs. Allure, Sydney, and Drew arrived, Mia presented him proudly. “Look what our web designer did. Dressed up, plugged himself, gagged himself, and locked himself in a tiny cage. Naughty boy.”
Mrs. Allure’s face darkened. She questioned James, pulling the cum-coated gag out briefly. He admitted he had been bringing clothing and toys home for days. She didn’t notice the cum as she shoved the gag back in.
She directed the girls coldly: “If he likes playing damsel in distress so much, then let’s make him one for tonight.”
They released him from the standing ropes only long enough to remove the anal plug first, then retied him more cruelly: a strict armbinder pulling his arms behind his back, a cold steel anal hook slid in and chained to his collar, forcing him to stay arched, and a wide spreader bar locked between his ankles.
The punishment dragged out for nearly an hour.
Sydney and Drew handled breath play — pressing gloved hands and boots over his mouth and nose while he thrashed. They pinched and twisted his nipples through the latex bra and slapped the tiny steel cage mercilessly. Mrs. Allure and Mia continued the whipping and torment — crop strokes, fingers probing, cruel taunts about his rule-breaking.
James resisted the entire time — cursing into the gag, twisting against the ropes, furious that Mia secretly held his key and disgusted by how the very thing he found repulsive had now happened to him.
Finally they released him. Mrs. Allure sent him home still locked in the tiny cage, still wearing the leather outfit under his street clothes… but she made him keep the glossy black patent mid-thigh boots on. She tossed him a long raincoat to cover everything.
“Go home. We’ll deal with you tomorrow.”
James walked through the rainy streets, the tall patent boots clicking loudly under the raincoat. He got several weird, lingering looks from passersby.
He finally reached his small rented room. He took the boots off before climbing into bed. His phone buzzed repeatedly with texts and pictures from Mia, plus voice notes of her cold, sadistic laughter. “My secret locked boy… how does that tiny cage feel? Sweet dreams tonight.”
James crawled into bed still caged, angry, humiliated, and aching. He stared at the pictures until exhaustion finally pulled him under

If you want to read more see the link in my bio!

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u/jjds500 — 11 days ago

Zara’s filthy Night

Zara lounged like a wicked goddess on the oversized armchair, her silky black robe open, one leg draped over the armrest. Her fingers lazily stroked her swollen, dripping pussy as she watched her collared, cuffed boyfriend James on all fours in front of her. Thick leather cuffs locked his wrists behind his back, a heavy steel chastity cage trapped his aching cock, and a thick leather collar with a dangling tag that read “Zara’s Bi Slut” circled his throat.
Alex, the dominant, hung bull they’d invited, knelt behind James. His massive, veined cock—easily twice the size of James’s caged dick—was slick with lube and already half-buried in James’s stretched hole.
“Deeper,” Zara commanded, her voice husky and dripping with lust. “I want to see my little bitch boyfriend get properly ruined.”
Alex slammed forward, burying every thick inch in one brutal thrust. James cried out, the sound muffled as his face was shoved toward the floor. The chastity cage swung uselessly beneath him, a steady drip of pre-cum leaking from the tiny hole at the tip.
Zara’s eyes lit up with wicked delight. “Fuck yes… Look at you, baby. Taking a real man’s cock like a desperate whore while I watch. Your tiny locked clit is dripping everywhere. So fucking pathetic and hot.”
She stood up, letting the robe fall completely, and walked over. Grabbing James by the hair, she yanked his head up and spat directly onto his face. “Open your mouth, slut.”
James obeyed instantly. Zara shoved two fingers into his mouth, letting him suck them clean before she returned to her chair and spread her legs wide, exposing her glistening, shaved pussy.
“Bring that hungry tongue over here while Alex destroys your ass.”
Alex didn’t slow down. He gripped the chain attached to James’s collar and used it like reins, yanking him forward while pounding his hole mercilessly. The wet, filthy sounds of deep anal fucking filled the room—skin slapping, lube squelching, James’s muffled moans vibrating against Zara’s cunt as his face was forced between her thighs.
Zara moaned loudly, grinding her soaked pussy against James’s eager tongue. “That’s it, eat your goddess’s cunt while you get fucked like a bitch. I can feel every thrust pushing your tongue deeper inside me. God, this is perfect.”
She reached down and twisted one of James’s nipples hard, then slapped his face lightly. “Deeper with that tongue, slut. Suck my clit like you mean it.”
Alex started spanking James’s ass hard between thrusts, leaving bright red handprints. “Your hole is gripping me so tight. Such a greedy little fucktoy.”
Zara’s breathing grew ragged as she watched her boyfriend get used. She pulled James’s face harder against her, smothering him in her wetness while Alex railed him without mercy.
“I’m going to cum all over your face while he breeds you,” she growled. “And you’re going to thank him afterward by cleaning his cock with your mouth.”
James whimpered desperately, tongue working frantically on her clit and folds. The relentless pounding from behind, the burn in his stretched ass, the painful tightness of the chastity cage, and Zara’s dominant moans pushed him into total submissive bliss.
Zara’s thighs began to shake. She cried out in ecstasy, flooding James’s mouth and face with her powerful orgasm, grinding and riding his tongue through wave after wave of pleasure.
When she finally came down, she smiled down at her wrecked boyfriend, stroking his sweat-soaked hair.
“Good boy. Now keep licking gently while Alex fills your guts with cum. Then you’re cleaning both of us… with your tongue.”
Alex grinned, slamming harder, chasing his own release deep inside James while Zara watched with pure, satisfied lust.

reddit.com
u/jjds500 — 13 days ago
▲ 71 r/ChastityStories+1 crossposts

Desire Key West Part 2

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The next morning James arrived early, exhausted and aching. The tiny pink steel cage had kept him in a state of constant, painful frustration all night. His balls were swollen and sore. He carried a bag containing every single item he had ever taken home.
Mrs. Allure was waiting for him alone in the front lounge. She closed the door and pointed to the chair opposite her.
“Sit down, James.”
He sat, face burning with shame. He opened the bag and laid everything out: the leather skirt, white blouse, latex bra, plugs, cock ring, ropes, and more.
“I’m sorry, Mrs. Allure,” he said quietly. “I broke every rule. I used the playroom when I wasn’t allowed. I even took things home with me. I’m returning all of it. I have no excuse.”
Mrs. Allure studied him for a long moment, then nodded. “Good. At least you’re honest about that much.”
James swallowed hard, remembering Mia’s strict instructions. His voice came out strained and humiliated. “And… I want to keep the cage on. I’ll pay for it. Whatever it costs. Please let me keep it.”
Mrs. Allure raised an eyebrow but agreed. “Very well. You will pay for the cage. From now on you will help out in the store however the girls need you. The others don’t need to know the full details. This stays between us for now.”
The Week in the Store
James’s days became a slow torture of desperation. He helped customers test gags, modeled latex and leather outfits for photos, and demonstrated restraints. Every movement made the tight cage bite into him. By Wednesday he was leaking constantly in his pants, shifting uncomfortably while helping a client try on a corset. Drew noticed and smirked but said nothing. By Thursday he was visibly flushed and distracted, his voice cracking when he spoke. Sydney commented once, “You seem… tense lately, James,” with a knowing look. He spent every lunch break in the bathroom trying (and failing) to get relief through the bars of the cage.
Every night after closing, Mia summoned him for their private sessions.
Night 1 – Anal Play & Boot Worship
Mia had him on his knees in the center of the playroom. “Start with my boots, thief. Show me how much you love them.”
James hesitated, but Mia grabbed his hair and pressed his face to her glossy pink leather thigh-high boots. He began kissing and licking them obediently while she watched with a cruel smile. “That’s it… worship them properly. I see how you stare at our boots all day. You don’t just want to look — you want to serve them, don’t you?”
He licked every inch — the toes, the insteps, the tall shafts — while she slowly turned, making him follow on his knees. After nearly thirty minutes of devoted boot worship, Mia bent him over the padded bench, wrists cuffed behind him.
She spent the next two hours on slow, teasing anal play. She started with her fingers, then moved to progressively larger plugs while the vibrating prostate massager buzzed against his spot. “You clench so greedily every time I push deeper,” she purred. “Listen to those pathetic little moans.”
Then she did something that made his mind spin. She slipped off one pink leather boot, still warm from her foot, and pressed the sharp stiletto heel against his entrance. “You love these boots so much… let’s see how much you can take.” She worked the heel inside him slowly, fucking him with it while the other boot stayed pressed against his face for continued worship. James gasped and whimpered around the leather, leaking heavily into the cage. “That’s right… take my heel like a good locked boy.” She never let him cum.
Night 2 – Pegging
Mia wore a thick strap-on. She made him drop to his knees first. “Suck it, James. Show me how much you want it.” He resisted, but she grabbed his hair and forced the silicone cock between his lips, making him gag and drool on it while she laughed. “Good boy… get it nice and wet for your ass.” Then she pegged him hard while slapping his locked cage. He came dry, ruined, and spent the rest of the night leaking and frustrated.
Night 3 – Impact Play
She bound him over a spanking bench and used a variety of paddles, crops, and a heavy flogger on his ass and thighs until he was shaking. Every strike made the cage bounce and leak more. “You’re dripping like a faucet,” Mia laughed. “Every time I hit you harder you throb in that tiny prison. You love the pain, don’t you?”
Night 4 – Wax Play
Mia lit several candles and dripped hot wax slowly across his chest, nipples, and locked cock while he was spread-eagled. The heat and sting made him hiss and arch. “Look at you leaking all over the wax,” she said with a cruel smile. “Your body is telling me things your mouth won’t.”
Night 5 – The Confession & Naked Tease
Mia had him tied spread-eagle. She edged him mercilessly for over an hour, then suddenly unlocked the cage. His cock sprang free, aching and purple. She stroked him slowly.
“Tell me what you really want, James. Be honest and I’ll let you cum.”
He resisted for nearly forty minutes, shaking his head. Mia kept teasing him about release, promising an orgasm if he told her the truth, edging him mercilessly. Every time he hesitated she triggered the shocking plug. Finally he broke.
“I… I want to be feminized,” he gasped. “I want the clothes, the body, the softness… I want to be turned into a girl. I’ve wanted it for years.”
Mia smiled viciously. She flipped him upside down in suspension, forced a ring gag into his mouth, and stroked him until he came hard — shooting straight into his own open mouth. James choked, repulsed and humiliated.
Then she surprised him completely. For the first time she slowly stripped completely naked in front of him. James had never seen any of them naked before. His eyes widened as she sat on the bench opposite him, spread her legs, and began slowly masturbating while maintaining eye contact. “Watch me cum, locked boy. This is what you’ll never get until I decide you’ve earned it.” She made a big show of it, moaning loudly, fingers moving faster until she came hard right in front of him, her body shuddering. James was left trembling, cage dripping again, mind reeling.
The next evening Mia surprised him. She had invited Sydney and Drew without warning. James was already bound tightly — armbinder, shocking plug still in, spreader bar.
Mia explained everything to them: “I’ve been holding his key the whole time. I caught him, locked him, and I’ve been using him every single night — anal with my heel, pegging, impact, wax, teasing… all of it. He’s my secret locked boy.”
Sydney’s eyes widened with genuine shock and delight. “Mia, you absolute bitch! You kept this delicious little secret all week? I’m impressed… and a little pissed you didn’t share sooner. But damn, this is hot.”
Drew looked both surprised and excited, her switch side clearly intrigued. “Wait — you’ve been playing with him every night and we had no idea? That’s actually really hot. I’m fine with it… but next time we’re all involved.”
Mia turned to James. “Tell them exactly what you admitted to me last night. What you really want and why.”
James hesitated. Mia triggered the shocking plug hard. He cried out and finally confessed in detail: “I want to be feminized… I want the clothes, the curves, the softness. I want to look pretty and be completely controlled. I’ve fantasized about it for years but was always too ashamed to say it.”
The three women reacted strongly.
Sydney grinned wide. “Holy shit. Our quiet little web designer wants to be a girl? That explains so much about how obsessed you are with our boots. You don’t just like them — you want to wear them, don’t you?”
Drew’s eyes lit up. “Oh my god, yes. That’s why you always stare at our legs. You want to be the one clicking around in tall patent boots and latex. That’s adorable… and incredibly hot.”
Mia laughed. “Exactly. He’s been leaking every time he sees our boots because he wants to be us.”
The three women spent the rest of the night discussing plans while James hung there, locked again, leaking, and deeply ashamed

u/jjds500 — 11 days ago

Desire Key West

Part 1: The Slow Seduction
James had fled New York’s gray grind six weeks earlier, drawn to Key West by sun, salt, and the promise of something freer. Cash was tight, so when the ad appeared — “Web designer for upscale fetish boutique. Immediate start. High pay. Absolute discretion required.” — he jumped at it.
Mrs. Allure replied personally. The interview at Desire left him breathless.
The boutique was a restored pink conch house off Duval — elegant, discreet, with frosted windows and a small gold plaque. Mrs. Allure greeted him in a white linen blouse open low over a black latex corset, a supple black leather pencil skirt, and gleaming thigh-high patent leather boots with six-inch chrome heels.
Inside was pure high-fashion fetish: racks of latex and leather, steel toys displayed like art, and a discreet soundproofed playroom at the back with padded leather benches, mirrors, hooks, and shelves of ropes and toys. “Clients test items here,” Mrs. Allure explained coolly. “You are not to use it. Ever. The merchandise is strictly off-limits after hours. Understood?”
James nodded. He understood.
The saleswomen were intoxicating.
Sydney — tall raven-haired in blood-red latex with structured leather corsetry and laced thigh-high leather boots.
Drew — curvy blonde in a white leather blouse unbuttoned low over a black latex bra, tight black leather pencil skirt, and glossy black patent mid-thigh boots.
Mia — petite brunette in a short pink latex dress with delicate leather straps and matching pink leather thigh-high boots. She was the most dangerous — a true sadist with a sweet smile and wicked eyes.
From his very first week, Mia began flirting. Sly little comments when no one else could hear.
“Careful around the leather, James… it has a way of making people want to misbehave.”
“You look like you’d fill out one of Drew’s skirts nicely.”
“Night shift must get lonely… if you ever need someone to test a blindfold on you, I’m very gentle.”
On the evening of his second week, after the last customer left, Mrs. Allure insisted they all stay for drinks in the front lounge. Rum cocktails were poured. The conversation turned playful and probing.
The girls pestered James about his sex life. “So, James,” Drew asked with a smirk, “what’s a cute guy like you into down here? Any wild stories yet?”
Sydney leaned in. “Yeah, spill.”
Mia tilted her head sweetly. “Come on… don’t be shy.”
James shifted uncomfortably. “Honestly? Not much. I haven’t really met many people yet. Work and settling in have kept me busy. My last relationship was pretty vanilla… nothing exciting.”
The girls shared freely, their lives wildly different.
Sydney laughed. “I’m a switch. I love threesomes and meeting people out, switching roles for each scene. Keeps things exciting.”
Drew grinned. “I’m a loving dom. I only pick guys up to peg them and make them realize that true joy is from being used properly by a girl. Most fight it at first… then thank me later.”
Mia’s eyes sparkled with dark delight. She reached into her purse and pulled out a small keyring heavy with at least a dozen tiny keys, dangling it in front of everyone. “I’m a sadist. I love picking guys up at bars, bringing them back here or to my place, and locking them in chastity. They leave completely denied and desperate, then have to beg me to release them when they have to fly home. I make them pay extra or do something truly humiliating before I unlock them. Watching them break is my favorite part.”
James felt a strong wave of repulsion twist in his stomach. Being locked up and forced to beg? That sounds like a nightmare, he thought. No way I’d ever let anyone do that to me. The idea disgusted him deeply.
Later in the conversation James admitted, “I did get tied up once with a belt by my ex. It was okay, I guess. She wanted to stick a finger in my butt but I said no.”
The girls reacted immediately.
Sydney smirked. “A belt? Cute. You should have let her. Anal can be amazing if done right.”
Drew smiled warmly. “A lot of guys discover they love it once they try it properly. I would have made it feel good for you.”
Mia’s sadistic grin widened. “You said no? How adorable. I would have made you beg for it… and then done it anyway while you were locked and helpless.”
James felt even more uneasy but kept his face neutral.
He finished his drink and left early.
As soon as the door closed behind him, the girls gossiped.
Sydney smirked. “He’s definitely curious.”
Drew laughed. “Poor thing has no idea what he’s walking into.”
Mia just smiled darkly. “Leave him to me… I’m going to enjoy this one.”
For the next several nights the temptation grew. James started sneaking clothing and toys home. One night he tried on a black leather pencil skirt and patent boots while watching kinky porn. Another night he wore the white leather blouse and latex bra, stroking himself to videos of sadistic women. The fantasies consumed him.
By night nineteen the ache was unbearable.
The breaking point came on the twentieth night — a raging tropical storm.
Mrs. Allure and the girls left early for a private party. James locked the front door, heart hammering. He slipped into the playroom, dimmed the red lights, and stripped.
He chose Drew’s style: crisp white leather blouse unbuttoned low, glossy black latex bra, tight black leather pencil skirt, glossy black patent mid-thigh boots. He added the locking leather collar and wrist cuffs.
He lubed the thick vibrating plug with rotating head and worked it deep inside himself, turning it on low. He snapped the tight black cock ring on. Then he gagged himself with a thick penis gag, buckling it tightly. Finally he rigged the standing self-bondage — wrists clipped high, ankles locked to floor rings. The last carabiner clicked… and he realized the safety release was out of reach. He was helplessly stuck, blindfolded, gagged, plugged, ringed, and dressed in stolen merchandise.
Mia returned first — she had forgotten her phone. She stepped in and let out a low, delighted laugh.
“Ohhh, James…” she purred, circling him. “Look at you. All dressed up in Drew’s favorite leather like a little thief. Blindfolded. Gagged with a cock in your mouth. Plugged and ringed and completely stuck. Did you really think no one would find you?”
James made a muffled, angry sound.
Mia’s voice stayed sweet for now. “Mmm, that plug is buzzing so nicely inside you. You’re going to look so good locked up just like the others I play with. You’ll be joining my little collection of denied boys.”
James shook his head frantically, trying to protest around the gag.
Mia stroked the leather skirt over his straining cock. “Oh yes you will. Beg for it, James. Beg me to let you cum. I want to hear you moan like the desperate little rule-breaker you are.”
James resisted, but the plug kept swirling and vibrating. Mia edged him mercilessly for long minutes.
“Beg,” she whispered, voice turning darker. “Beg like you mean it or I leave you here all night.”
Finally James broke and moaned desperately around the gag, nodding frantically.
Mia laughed. “Good boy. Cum for me.”
She sucked him hard while the plug buzzed on high. James came explosively, shaking in the ropes.
The second he finished, Mia’s sweet mask dropped. Her tone turned cold, cruel, and viciously sadistic.
“You pathetic little shit,” she hissed. “You actually begged me to make you cum while breaking every rule. Disgusting.”
She pulled the penis gag from his mouth, coated it thickly in the cum still on her fingers and lips, and forced it back between his teeth, buckling it even tighter. “There. Now you can taste yourself, thief.”
James tried to protest, but the cum-coated gag muffled him.
Mia grabbed the tiny pink steel cage. James immediately started thrashing, twisting his hips away. “No— fuck you— get that thing off me!”
Mia laughed meanly, squeezed his balls until he yelped, and forced the brutally small, tight cage down over his softening cock while he fought her every inch. The steel crushed him painfully. She locked it with a loud click.
“You’re staying locked for me now, James. Our dirty little secret. The others will think you did this yourself. Tell them the key is at home. If you tell them the truth, these pictures go everywhere and you lose your job.”
Mia called the others. “Come back — James locked himself up in the playroom. You have to see this.”
When Mrs. Allure, Sydney, and Drew arrived, Mia presented him proudly. “Look what our web designer did. Dressed up, plugged himself, gagged himself, and locked himself in a tiny cage. Naughty boy.”
Mrs. Allure’s face darkened. She questioned James, pulling the cum-coated gag out briefly. He admitted he had been bringing clothing and toys home for days. She didn’t notice the cum as she shoved the gag back in.
She directed the girls coldly: “If he likes playing damsel in distress so much, then let’s make him one for tonight.”
They released him from the standing ropes only long enough to remove the anal plug first, then retied him more cruelly: a strict armbinder pulling his arms behind his back, a cold steel anal hook slid in and chained to his collar, forcing him to stay arched, and a wide spreader bar locked between his ankles.
The punishment dragged out for nearly an hour.
Sydney and Drew handled breath play — pressing gloved hands and boots over his mouth and nose while he thrashed. They pinched and twisted his nipples through the latex bra and slapped the tiny steel cage mercilessly. Mrs. Allure and Mia continued the whipping and torment — crop strokes, fingers probing, cruel taunts about his rule-breaking.
James resisted the entire time — cursing into the gag, twisting against the ropes, furious that Mia secretly held his key and disgusted by how the very thing he found repulsive had now happened to him.
Finally they released him. Mrs. Allure sent him home still locked in the tiny cage, still wearing the leather outfit under his street clothes… but she made him keep the glossy black patent mid-thigh boots on. She tossed him a long raincoat to cover everything.
“Go home. We’ll deal with you tomorrow.”
James walked through the rainy streets, the tall patent boots clicking loudly under the raincoat. He got several weird, lingering looks from passersby.
He finally reached his small rented room. He took the boots off before climbing into bed. His phone buzzed repeatedly with texts and pictures from Mia, plus voice notes of her cold, sadistic laughter. “My secret locked boy… how does that tiny cage feel? Sweet dreams tonight.”
James crawled into bed still caged, angry, humiliated, and aching. He stared at the pictures until exhaustion finally pulled him under

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u/jjds500 — 17 days ago