Can You Last as Long as Him?
A Fictional SPH Story by Rustyleaks.
Tyler moaned a weak “yes, Mistress” as she reached her delicate hands forward and caressed his caged cock. He had been locked inside the small pink chastity cage for two weeks. Today marked the halfway point in their yearly Locktober Challenge, which meant he had a 50/50 chance of being allowed to cum tonight. Megan always had a special challenge for him to earn his mid-October release. For the last two years, he had passed the tests, and he hoped to continue his winning streak. This year had been harder than the previous years since Megan had pranced around the house every day in nothing but lace lingerie, teasing him relentlessly with soft touches and dirty talk.
“Good!” Megan exclaimed and leaned forward to kiss him. The key to his manhood danced softly on his chest from the small chain around her neck as their lips met. The coldness of the steel sent shivers down his whole body.
“I have a special challenge for my special sissy today.” She continued, taking his cage between her thumb and forefinger. She stroked his device gently a few times before reaching for her phone on the nightstand.
“You remember James, right?” She asked coyly as she scrolled through her phone.
“Remember James?” Tyler thought. “How could I possibly forget James?”
He nodded as his cock pulsed inside the pink prison.
James had been a young intern at the financial firm Megan worked at when Tyler met him at a company Christmas party years ago. He was now a junior partner at another firm, and almost immediately after he left Megan’s firm, the two started hooking up. He had an enormous cock, and Megan enjoyed telling Tyler about all the things he’d do to her when she gave him teasing handjobs. Truth be told, Tyler loved hearing about it. Their open relationship had ignited the spark between them, and their number 1 rule was that they told each other everything about the partners they hooked up with, and while Tyler wasn’t packing anything close to 9.5 inches of raw sexual power, he still managed to have his own extramarital exploits to share with Megan.
For 11 months out of every year, they each explored the pleasures of their open relationship. But October was Megan’s Femdom month, where Tyler was locked in chastity and devoted to her pleasure alone.
“I see your cock remembers James, too.” Megan purred as she noted the cage flexing away from his pelvis. “Let’s get that tiny little cage off him.” She made a pouty face as she took the key from between her tits.
A slow click, and Tyler felt the cool evening air surrounding his cock as it swelled to a full 6 inches. Megan left the pink base ring on and began rubbing her index finger slowly up the side of his hardened cock.
“So James and I made a little video for you, sissy.” She said casually as she watched his cock twitch against her finger. “He filmed me sucking his perfect cock just for you.” She positioned herself on her stomach between his legs and kissed the tip of his cock. Tyler inhaled sharply as a large drop of precum oozed out of the tip of his cock.
“Your Locktober challenge is to watch the video while I suck your cock the same way.” She paused, her eyes locked onto his. “And you have to last until the end.”
Tyler gulped. His stamina normally wouldn’t be a problem, but after two weeks of her teasing him in lace, he wasn’t so sure he’d have the self-control he was used to displaying. Luckily, he was very familiar with Megan’s oral skills on a cock, and he doubted anyone could last much longer than a few minutes in her talented mouth.
“If you last until the end.” She continued, giving his shaft a gentle lick. “You may cum in my mouth just like James does at the end of the video. A nice full orgasm in my warm wet mouth.” She licked her lips and batted her eyelashes at him seductively.
“If you don’t.” She blew softly against his frenulum. Tyler shivered at the sensation.
“If you don’t.” She repeated. “I will lock you back up inside your little pink cage, and you’ll hafta wait until November to be unlocked again.” She took the head of his cock into her mouth and sucked it once, letting it slip out of her mouth with a loud ‘pop’.
Tyler groaned loudly as his cock sprang from her mouth and slapped into his stomach, leaving a wet spot where the head touched. Megan ran her finger through the wet spot and brought it to her lips, slowly pressing it into her mouth as if it were a hard cock.
“Mmmm, your precum is always sweetest when you’re desperate, sissy.” She smiled mischievously at him and reached for her phone.
She navigated to the video and handed it to him.
“Don’t press play yet.” She instructed and sat back up on her knees.
Tyler’s cock pulsed and strained as he watched her unclip her bra and slide it off her arms, exposing his two greatest weaknesses. Her tits were large and soft and sat just right on her small frame. The sight of them alone made his mouth water. He could worship them for hours if she let him. She smiled down at him as she saw his reaction. His wide eyes, his heavy breathing, his desperate cock; she felt her pussy get wetter. Had it been any other day in any other month, she would’ve straddled his cock and rode him until he exploded inside of her, but this was October. Her pussy was off limits to him.
She repositioned herself onto her stomach and pressed her tits against his erection, causing him to bite his lip and squeeze his eyes shut.
“You are so fucked, little one.” She thought to herself.
“Ok, sissy. Are you sure you’re ready?”
Tyler wanted to beg for a few minutes to gain his senses and let his cock settle down, but he knew that wish would never be granted. He nodded and looked at her phone screen.
The “play” icon was directly over James’ enormous cock. The thick veins bulged out of it like vines wrapped around a thick tree trunk. James was easily over twice his own girth. He had never seen James’ cock before, only heard about it graphically from Megan’s teasing stories, yet even her detailed accounts did it no justice. It was a magnificent cock that would put the proudest porn star to shame. Tyler swallowed hard as he realized that a 3.5in difference was so much greater on a cock than a ruler.
“Play,” Megan commanded.
Tyler pressed play. Megan immediately began licking the tip of his cock, mirroring the video perfectly. He felt his breath catch at the sensation and his head pressed back into the pillow.
“Eyes on the video, sissy.” Megan’s soft command jerked his attention back to the video. His eyes locked onto her lips wrapping around James’ cock, barely taking in the full head before pulling off of it, leaving a saliva string between her tongue and his tip. The sensation was hypnotic. He was watching Megan suck James while feeling Megan sucking him the same way. Another loud groan escaped his lips.
Megan was softly sucking James’ tip while working both hands along his shaft in a twisting motion.
“Mmmm.” He heard Megan from between his legs. “I needed two hands for James, but I barely need one for yours, sissy.”
“Oh fuck!” Tyler whimpered. He felt a tremble building in his glutes and vibrating through his thighs as he struggled to maintain control. Whenever Megan compared his size to her lovers’ sizes, it would drive him mad with lust, and he almost tipped over the edge.
“P-Please!!” He whispered through gritted teeth.
“What’s the matter, sissy? Is this too much for you?” Megan’s mocking innocent tone was just icing on the cake for his ears.
Tyler curled his toes and squeezed his pelvic muscles as hard as he could to fight off the orgasm. His body resisted, but his willpower eventually won after the longest 5 seconds of his life.
He looked at the bottom of the video, and his eyes nearly bulged out of his head.
“Twenty-Two minutes long!?” He wailed.
He felt Megan chuckle as she sucked his tip.
“Oh no.” She cooed. “Can my little sissy not control his little cock for 20 minutes? It’s no wonder your mistress locks you away.”
“Fuuuuuuuck,” Tyler growled as he watched Megan gag on James’ length as she forced it down her throat. He felt Megan easily take his whole length simultaneously without a sound. The humiliation crashed over him like a wave, yet he felt his cock grow harder.
Finally, Megan pulled off James and began running her lips up and down the side of his shaft. When he felt the same on his cock he knew he was a goner.
“I’m gonna cum! I’m gonna cum! Ooooh fuck fuck! Oh fuck mistress!” He was nearly screaming as he felt his orgasm climbing up his shaft.
Megan immediately removed her lips and squeezed the base of his cock hard with one hand. With the other hand, she pressed her flat palm down on the tip of his cock. Tyler squirmed and yelped as his body tried to release its orgasm, but her grip was unwavering. He felt his cum rebound back into his body, almost the equivalent of a gut punch. He collapsed back into the mattress, a panting, wheezing mess. The video still played softly from the phone in his hand. It had been 4 minutes.
Megan giggled as she released her grip. She gently squeezed his shaft in one long stroke. The tiniest drop of cum emerged from his withering cock. She collected it with her finger and pressed it into Tyler’s mouth.
“See? I told you it’s sweeter when you’re desperate.” Her voice was like velvet and sharp knives at the same time.
Tyler whimpered as his legs spasmed uncontrollably.
“Awwww, don’t cry, sissy,” Megan said with her pouty innocent tone. “I didn’t expect you to last the whole time. Smaller cocks always cum faster than the big ones. Now let’s get this little sissy cock back in its pink cage.”
Tyler watched defeatedly as Megan slipped the chastity device back on his cock and clicked the lock shut. She smiled with satisfaction and gave the tip a quick kiss.
“All locked up until November.” She gave it a quick wiggle. “Now come here and lick my pussy while I watch the video of James fucking me. If you do really well, mistress might even let you watch it later.”
Tyler obeyed.
—
Tyler knelt between Megan’s spread thighs, the pink cage a familiar, humiliating weight against his balls. The base ring still hugged the root of his cock, a constant reminder of what he’d lost. Defeat tasted like his own ruined precum, still faintly sweet on his tongue.
Megan propped herself against the pillows, phone in one hand, the other drifting down to part her glistening pussy lips. She was already wet—soaking, actually—her arousal smeared across her inner thighs. The sight made Tyler’s caged cock ache with a dull, useless throb.
“Eyes up here, sissy,” she said, not looking at him. She tapped the video, and James’s voice filled the room, low and confident. “There’s my good girl. Take it deeper.”
Tyler leaned in, pressing his mouth to her heat. She tasted tangy and warm, her clit swollen against his tongue. He started slow, tracing circles the way she liked, but Megan’s free hand tangled in his hair and shoved his face harder against her cunt.
“Don’t get shy now. Lick me like you mean it.”
The video played on. James’s grunts mixed with Megan’s recorded moans—wet, sloppy sounds of James’s thick cock sliding in and out of her. Tyler could hear every inch of it, every squelch, every slap of skin. His cage flexed uselessly against his trapped erection.
“That’s it,” Megan breathed, tilting her hips up. “Right there. Fuck, his cock is so much bigger than yours, Tyler. I can’t even feel you anymore when he’s inside me for real.”
Tyler whimpered against her pussy, tongue working her clit as she ground against his face. The video shifted—James was fucking her now, her legs over his shoulders, her back arching off the mattress. The recorded Megan’s screams filled the room.
“You hear that?” the real Megan panted, looking down at him. “That’s what a real cock does to me. You’ve never made me sound like that. Not once in six years.”
His tongue moved faster, desperate to please, desperate to earn even a moment of her approval. The cage bit into his flesh as his cock strained uselessly.
Megan’s thighs began to tremble. “Don’t stop. Make me cum, sissy. Earn your chance to watch.”
Tyler buried his face deeper, lapping at her folds, sucking her clit between his lips. The video reached its crescendo—James roaring as he emptied himself inside filmed-Megan, her moans breaking into breathless laughter.
The real Megan’s back arched, her grip on his hair painful. “Fuck—yes—right there—”
She came with a sharp cry, her juices flooding his chin, her thighs clamping around his head. Tyler kept licking, gentle now, drawing out every aftershock until she pushed him away.
Megan lay panting, a satisfied smile curving her lips. She turned the phone toward him, pausing the video on a frame of James’s glistening cock buried inside her.
“Good boy,” she murmured. “Maybe tomorrow night I’ll let you watch it while I cage-train your tongue.” She stretched lazily, letting the key around her neck catch the light. “For now, go sleep on the floor beside the bed. Mistress is tired.”
The floor was cold against Tyler’s back, the thin throw blanket Megan had tossed him doing little to ward off the chill. Above him, he could hear her breathing slow into sleep, the soft rustle of sheets as she settled in. His caged cock still throbbed, a dull persistent ache that matched the sting of her juices drying on his chin.
He lay awake, staring at the ceiling, replaying the evening. The taste of her lingered on his tongue. The sounds of James fucking her echoed in his skull. His own failure was a weight pressing on his chest, heavier than the cage around his balls.
After what felt like hours, sleep finally dragged him under—a fitful, restless thing filled with fractured images of James’s cock, Megan’s twisted smile, and the key swinging just out of reach.
—
Morning light cut through the blinds, and Tyler woke to the click of Megan’s heels on the hardwood. She was already dressed—black pencil skirt, silk blouse unbuttoned enough to show the key resting in her cleavage.
“Up, sissy,” she said, nudging him with the toe of her pump. “We have a busy day.”
Tyler scrambled to his knees, wincing as the cage shifted. “Yes, Mistress.”
Megan circled him slowly, appraising. “Did you sleep well on the floor?”
“Yes, Mistress,” he lied.
She crouched, lifting his chin with one finger. “Liar. I heard you whimpering in your sleep. Dreaming of James, were you? Or of my cunt on your tongue?”
His face flushed hot. “You, Mistress. Always you.”
Megan smiled, slow and dangerous. “Good answer.” She stood, smoothing her skirt. “Now, I have errands to run. But first, I want you to make my breakfast. And you’ll eat yours from the bowl on the floor. No hands.”
Tyler nodded quickly, already scrambling toward the kitchen on all fours before she could correct his posture. He could feel her eyes on him, could hear the soft clink of the key as she moved.
In the kitchen, he prepared her breakfast with trembling hands—poached eggs, avocado toast, coffee the way she liked it. His own portion went into a stainless steel bowl: cold oatmeal, no sugar. He set the bowl on the floor by the table and served her on the good china.
Megan sat, scrolling through her phone as she ate. Tyler knelt by her feet, bending to lap at the oatmeal, the cold mush coating his tongue. The humiliation was thick, but his cock strained against the cage anyway.
“James texted,” Megan said, not looking up from her phone. “He says he had a wonderful time last month. He asked if you’ve been keeping me satisfied.”
Tyler paused, oatmeal dripping from his chin. He wanted to disappear.
“Eat,” Megan said, her voice sharp.
He obeyed.
After breakfast, Megan set her plate aside and leaned back in her chair, spreading her legs slightly. “Since you were so good last night—licking me until I came—I’ve decided to give you a little reward today.”
Tyler’s head shot up, hope flaring in his chest.
She laughed at his expression. “Oh, don’t get too excited. You’re not coming out of that cage. But I’m feeling generous.” She reached into her purse and pulled out a small velvet pouch. “Stand up and lift your chin.”
He did as told, and Megan drew something from the pouch—soft pink satin with white lace trim. A collar. She fastened it around his neck, the small heart-shaped tag resting against his throat: Princess.
“There,” she cooed, adjusting it. “Doesn’t that feel pretty?”
The satin was soft as a whisper. The tag was cool against his skin. His caged cock pulsed.
“Thank you, Mistress,” he whispered.
Megan stood, straightening his hair. “Tonight, James is coming over for dinner. You’ll serve us. And then… you’ll watch.”
Tyler’s stomach dropped. His whole body went hot and cold at once. James—in their house. James, whose cock had filled his wife’s throat on video. James, who would sit at their table and eat food Tyler prepared while Tyler waited on him like a servant.
“Please, Mistress—”
Her hand cracked across his cheek, sharp and sudden. “Did I ask for your opinion?”
Tyler’s eyes watered. “No, Mistress. I’m sorry.”
She cupped his stinging cheek, thumb stroking the red mark. “Tonight is about showing James what a good little sissy you’ve become. You will be polite. You will be quiet. And you will do exactly as I say.” She kissed his forehead, gentle now. “Now go pick out something nice to wear. Something soft and pretty. Something James will laugh at.”
Tyler nodded, his throat tight.
Megan turned to go, then paused at the door. “And Tyler? After last night’s little fail, I think it’s time we try a new challenge. Maybe tonight I’ll let James pick the punishment if you can’t control yourself.”
His caged cock gave a hard, helpless pulse.
“Something to look forward to,” she said brightly, and disappeared down the hall.
Tyler stood alone in the kitchen, oatmeal still crusted on his lips, the collar snug around his throat. His wife was going to fuck James in their bed. And he was going to serve them while it happened.
He didn’t know if he wanted to cry or beg.
Both. Definitely both.
—
The credits rolled. The screen went dark, and for a long moment, the only sounds in the room were Megan’s slow, satisfied breathing and the faint, pathetic whimper that escaped Tyler’s throat.
He was still on his knees, the pink cage locked tight around his softened cock, the base ring a cold reminder of his failure. His chin was wet with her, his tongue aching from the effort of pleasing her while James’s recorded grunts filled his ears. The taste of her was everywhere—on his lips, his chin, his fingers. And still, he wanted more.
Megan stretched on the bed, her body languid, her skin flushed from the two orgasms he’d given her. She propped herself up on one elbow and looked down at him, her lips curving into that smile that made his stomach flip.
“Not bad, sissy,” she said, reaching down to stroke his hair. “Not bad at all.”
Tyler leaned into her touch, desperate for any crumb of approval. “Thank you, Mistress.”
She held up her phone, the screen now black. “James says he wants to make another video. Maybe next time, you’ll be in it.”
His caged cock gave a useless twitch. Just the thought of being filmed—of being seen like this, collared and caged and kneeling at the foot of the bed while his wife’s bull used her properly—sent a fresh wave of humiliation and heat through him.
Megan laughed at his expression. “Oh, you like that idea, don’t you? Maybe I’ll let him film you licking my ass while he fucks my pussy. Or better yet, maybe he’ll film you cleaning his cock after he’s done.”
Tyler’s face burned. His mouth opened, but no words came out.
“Shh,” Megan cooed, tapping his lips. “Don’t worry, sweetheart. I’ll decide what you can handle.” She swung her legs over the side of the bed and stood, stretching in the dim light. “Now, go get cleaned up. When you come back, I have a few things to tell you.”
He scrambled up, his knees sore, and hurried to the bathroom. The cold water stung his face, but it did nothing to cool the fire in his belly. He stared at his reflection, at the pink collar around his neck, at the small divot in his lip where his teeth had pressed too hard. Princess, the tag read, and he touched it with trembling fingers.
When he returned, Megan was sitting cross-legged on the bed, wrapped in a silk robe, the key still glinting in her cleavage. She patted the floor beside the bed, and he knelt there without being told.
“Good boy,” she cooed. “You’re learning.”
She opened her phone again, scrolling lazily. “James has some very interesting ideas for the rest of the month. Since you failed the Locktober Challenge so early this year, we’ve decided to make things a bit more… educational.”
Tyler’s stomach tightened. “Educational, Mistress?”
Megan nodded, her eyes still on the screen. “Lessons in self-control. In serving. In understanding your place.” She set the phone down and looked at him, her expression softening into something almost motherly. “It’s for your own good, honey.”
He swallowed. “Yes, Mistress.”
“Good.” She cupped his cheek, her thumb brushing over the little heart-shaped tag. “Now lay down on the floor, face up.”
Tyler obeyed, the cold hardwood pressing into his back. Megan stood over him, one foot planted on either side of his hips. She let her robe fall open, revealing the glistening swell of her pussy, still pink and swollen from his earlier attention.
“You did well tonight,” she said, lowering herself until she was hovering just above his face. “But I want you to remember something.”
She sank, her wet heat pressing against his mouth. His tongue darted out automatically, lapping at her, but she pulled back just enough to make him wait.
“James is the one who makes me feel like that,” she said, her voice dropping. “James is the one who makes me moan. James is the one who made me cum before tonight even started. You? You’re just the warm-up.”
Tyler’s eyes stung, but his cock—trapped and useless—strained anyway.
“Say it,” she murmured.
“I’m just a warm-up,” he whispered against her skin.
“Louder.”
“I’m just a warm-up!” he repeated, his voice cracking.
Megan smiled and lowered herself fully onto his face. “Good sissy.”
Tyler set to work with renewed fervor, his tongue sliding through her folds, lapping at her clit with a desperation that bordered on worship. Above him, Megan sighed and rolled her hips, letting him pleasure her while she reached for her phone again.
“James just texted,” she said, breath hitching as Tyler’s tongue found her clit. “He says next time, he wants you to wear a pretty pink dress when you serve us dinner. Something with a bow. He says he wants to reach under it and feel your cage while I’m on his cock.”
Tyler moaned into her, and Megan laughed, grinding down harder.
“I think that sounds perfect,” she purred. “Don’t you?”
He couldn’t answer—his mouth was full—but his muffled moan was all the answer she needed.
Megan came with a soft, satisfied groan, her thighs tightening around his head as she rode out the last waves of pleasure. When she finally pulled away, she sat back on the bed, breathing hard, a sheen of sweat on her skin.
“Look at you,” she said after a long moment, tilting her head. “Not a single inch of you free. Caged, collared, and covered in my cum. This is who you are, Tyler.”
He lay there, still on his back, staring up at her. His face glistened with her, his lips swollen, his throat raw. And somehow—somehow—he had never felt more at home.
“Yes, Mistress,” he whispered.
Megan reached behind her neck and unclasped the key, holding it up so it caught the light. “One more week until November,” she said, her smile sharp as a blade. “Think you can last?”
Tyler nodded, not trusting his voice.
She laughed, low and wicked, and let the key dangle between them. “We’ll see,” she said. “But I wouldn’t bet on it, sissy.”
She dropped the key back into her cleavage, rose, and flicked off the light.
In the darkness, Tyler lay still, listening to her settle into bed, feeling the ache of his cage and the sting of his collar and the wet, warm proof of his place in this house.
And when sleep finally came, it brought no peace—only dreams of pink satin, of James’s shadow falling over him, and of a key that spun forever in the light.
The End.
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