They used to be happily married but their relationship had become boring for her in recent years. So she decided to spice things up a bit. A perfectly reasonable solution to a stale marriage. Don't you agree?
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@sissyasmin
They used to be happily married but their relationship had become boring for her in recent years. So she decided to spice things up a bit. A perfectly reasonable solution to a stale marriage. Don't you agree?
Sissy Captions #27
Spending time in my rightful place 🤍🔐
On his third day as office maid, after he got changed into his uniform in front of Victoria, she revealed the ball gag he was to wear. Due to his frequent complaints to the women in the office and petulant reactions to being bossed around they had decided to silence him for the time being. Of course his reaction to being forced to be a maid were completely justified, but women wanted to foster a mentally in him that he was the one being unreasonable.
Carla and Simon's parents passed on when they were younger, so Carla had raised Simon for the last ten years. Now she was a very successful 32-year-old business woman and very driven. Simon on the other hand was completely the opposite. 10 years younger than Carla he still lived her but he hadn't found a stable job. And spent long periods unemployed. Thinking this was unacceptable she decided to put him to use around her large house. Together with her housekeeper, Audrey, they gradually tested the waters in how much they could boss him around. To the surprise he was quite submissive and a very diligent with his chores. It even seemed therapeutic for him. Over time Audrey was doing less and less housework and now acted as his matron/supervisor. She even start having him dress as a maid. Just simple outfits, a white blouse, knee length black skirt and comfortable smart trainers. Carla loved it and to their surprise, Simon, although slightly reluctant, wore the clothes without argument. He now did all the household chores with great efficiency so Carla and Audrey now decided to go all out and turn him into a full on sissy French maid, and him serve them and other women drinks and afternoon tea, on top of his chores. In the scene above Carla has taken him dress shopping for his sissy uniforms. Although he was deeply embarrassed at his first public outing, he obeyed his sister without question and tried an array of delightful sissy attire.
The store lights hummed, but all I saw was her, holding the stack of diapers like a trophy. My new life, all wrapped up in plastic and promises of permanent change. Each package represents a step further into my feminization, a constant reminder that my old life is gone. She chose those pastel colors, just for me.
I tugged at my pink pajamas, the floral pattern a pathetic attempt to retain some shred of masculinity. It didn't help. The diaper beneath felt thick and undeniable, a permanent fixture. My body is hers now. My money, my time, my very existence, all feeding into her Findom desires.
"Do you like your new diapers, sissy?" Her voice was soft, but edged with command, her eyes never leaving me. "They’re a good fit for my little girl, don’t you think? You should thank me. You look so pathetic.”
I swallowed, a lump of shame rising in my throat. I knew I should be grateful, for every single purchase, every single decision, because every single dollar went to her, to further my transformation. She is my goddess, the architect of my permanent future. This isn’t just a phase, this is a new me. A permanent me.
"You know, baby, these new diapers are just the beginning,” she continued, her lips curving into a smile. "We're going to make you so very pretty. Isn’t that right, princess?”
I nodded, my gaze dropping to the floor. My new permanent reality was a blend of embarrassment and anticipation. I knew, deep down, that she'd always have me right where she wanted me. My heart is now hers. And my money is too. This was permanent.
Is this what heaven looks like? Me kneeling before my omnipotent Goddess for all eternity? Forever in service to her?
I want a goddess to worship!!!!
You and your girlfriend are fiercely competitive. While watching a Poker game on television. Both of you are drinking and carrying on. Both of you declare. They are the superior poker player. So your girlfriend suggests a poker game. You agree. Not knowing how competitive she is. She says best two out of three. You play the first game you win. You play the next game. She wins. Now the pressure is on. As the cards are being dealt. She says, “ Let’s make a bet?” You say, “Why not? What should we bet?” She suggests a Winner Takes All. You agree not knowing exactly what she meant. She starts the deal. You sweat the moment. Time to show your hand. You lay your cards down. She lays her’s down. In absolute astonishment you lose. How did this happen you think? Before you say anything. She says, “Time to pay up!” She leads you to another room. You see a bed. On it is a total sissy outfit. She reminds you that you lost the game and you gotta pay. So you agree. She helps you dress. As you put on each piece of clothing. You feel a tingling sensation in your penis. You are dressed minus panties. She does your hair and make up. You’re getting hard now. You fight it, but you’re loving it. Now she hands you the matching panties. She tells you to wait. Just two more things are needed. A cock cage and plug. She cages you and plugs you. Then you put on the panties. You are in total bliss. When you accidentally tell her you love dressing like this and that you never want to be anything more than her sissy. She strokes your face and tells you she always knew and the game was fixed. Now this is your new life. It’s not a dream.
Now is not the time to be fussy sissy girl, mommy has a date and hes taking me out of town for the week. If everything goes as planned you'll be getting a Daddy when I get back. He's been asking about you more and more and he even said he would love to change a sissy diapy soon. Now all that being said mommy can't leave you here alone for a week with no one to take care of you can she? No no no, you know sissies can't change their diapys or get there own foods, and most importantly a sissy can never ever have any access to her sissy cage. That belongs to mommy and soon daddy will get the only keys to that cage by the way and he said he's going to glue both the cage and lock so it cannot come off until he cuts the cage. Also daddy told me that your wearing no less than 3 diapers at a time. Mommy will cut them so they leak into each other. Daddy said he likes the idea of you not getting a diapy chabge for as long as possible.
Ok now that we got you diapered and dressed up mommy has some advice for you if your going to get along with your sissy baby sitter. I have been talking with her for a few months about you and everything you had on your tumblr that landed you in this mess. Shes 19 and she is a total fucking brat. Now she has a kink of her own and that is pushing and breaking men's or in your case sissies limits. She knows all your kinks and fears and she has already told me a few of the ways you'll be spending your time with her and all mommy has to say is . . . When your crying and blathering like a real baby remember this is everything you had ever wanted and even not wanted to have happen. She works as an intern in a fertility bank. She has access to all the samples real men deposit as well as all the funky jizz that doesn't meet the cut. She said she has more cum saved up for you than 2 whole sperm banks have ready to sell.
Ok she's here little girl im going to greet her. Mommy loves her little sissy girl. Now fill those diapys and mommy will be getting updates from your sitter. Hi sissy girl my name is hah like id tell you. If you are allowed to speak you'll address me as Goddess. I own you as of right now. I've got your sissy dick cage keys in my purse and a tazer on the table. You'll be wearing a shock dog collar as well to ensure you don't get any silly ideas you little bitch. I'm not your mommy I don't have to be sweet, or kind, or even acknowledge your alive at all. Now I'm going to get some dinner and your going to watch me eat it all and then your going to sniff my feet and my ass while I watch some of my TV shows I'm way behind. Ok good chat.
Back after a short break, and straight back to posting again.
Here Sissy Jamie has been instructed by his Mistress to keep his hands in a new position whilst walking from now on. The ribbons tied to his wrist connect to his collar, preventing him from dropping his arms. Ensuring a delightful sissy pose.
Sissy slut
Randy’s Reward
The little silver bell on the nightstand chimed twice. Soft, almost musical. Randy froze mid-wipe in the kitchen, the damp cloth dripping onto the tile. His pulse jumped. The bell usually meant one of two things: Lauren needed something fetched right now, or he was in trouble.
He set the cloth down carefully, smoothed his onesie over the heavy, sagging bulk between his legs, and started the slow waddle down the hallway. Each step made the cold, swollen mess inside shift and squish audibly. He’d been marinating in it since late afternoon. Five, maybe six hours. The smell of stale piss was starting to creep up under the baby powder scent. He didn’t dare ask for a change. Not after last week’s reminder that “good boys wait until Mommy says so.”
When he reached the bedroom doorway, he paused, eyes on the floor. Lauren sat propped against the headboard in her silk robe, hair still slightly mussed from Marcus’s earlier visit. She wasn’t scowling. She wasn’t holding the wooden spoon or the hairbrush. She was…smiling. Soft, almost fond.
“Come here, baby,” she said gently. “Mommy has something for you.”
Randy’s stomach churned in confusion and cautious hope. He shuffled forward, head bowed, until he stood at the edge of the bed. The diaper forced his thighs apart, the onesie pulled tight across the front.
“Kneel.” Lauren commanded.
He obeyed, lowering himself carefully so the sodden padding didn’t squish too loudly. She reached out, cupped his cheek, and tilted his face up.
“You’ve been such a good boy lately,” she began, voice low and warm. “No fussing at mealtimes. You ate every bite of your num-nums without a single pout…even the mashed peas which I know you hate. You didn’t whine about having to take your pounding from my strap. And yesterday…” She traced a finger down his chest to the first snap of his onesie. “You didn’t even ask for a change when you got all messy after lunch. You just sat there in your poopy diapee, waiting so patiently until I decided it was time.”
Pop. The first snap of the onesie gave way.
Randy’s breath caught. She was undressing him. Slowly. Deliberately.
Pop. Second snap.
“And when Marcus came over…” she continued, eyes locked on his, voice dropping into that sweet, condescending purr, “you were perfect. You fluffed Marcus’ cock so nicely for me with that little mouth of yours, sucking and licking until he was rock hard and throbbing, ready to fuck Mommy. You knelt there the whole time and watched every deep thrust and every moan like a good little cuck while he took what was his, didn’t you? You held nice and still while he jizzed all over your face, painting your cheeks and lips, and you didn’t sulk even once while it slowly dripped down your chin and onto your bib during round two. And after he filled me up again, you licked all his thick cum out of my pussy, sucking it out like the eager little cleaner you are. All without a single complaint. I’ve never been more proud of my good little cuck boy!!”
Pop. Pop. Pop. The onesie burst open, exposing the cartoon teddy bears stretched taut over the massively swollen, yellowed front of his diaper. The plastic backing glistened faintly under the lamplight.
Lauren hooked two fingers into the waistband and gave a playful tug. The padding sagged heavily, straining at the tapes.
“Look at this...” she murmured. “So full. So heavy. You’ve been carrying all that for hours, haven’t you, sweetie? Just letting it get colder and squishier against your poor little bottom!”
Randy nodded, cheeks flaming. A tiny whimper escaped.
She smiled wider. “You’ve earned something nice tonight, sweetie. A real reward!”
His heart hammered so hard he thought she could hear it.
Lauren reached into the nightstand drawer and pulled out the small silver key. She dangled it in front of his face, letting it swing like a pendulum. “Tonight...you actually get to fuck your girlfriend.”
Randy’s stomach flipped with dizzying hope. After months of nothing but watching and cleaning up after Marcus, she was finally going to let him inside her again. He couldn’t even remember what her warm, soft pussy felt like anymore. Just faded, desperate dreams that left him aching every night. His caged cock twitched violently, leaking even more as fresh, trembling excitement flooded through him.
She cupped the front of his diaper, giving the sodden bulk a gentle squeeze. He whimpered at the pressure against his swollen balls.
“Let’s get this off you first,” she whispered.
She peeled the first tape open with a long, deliberate rip. Cool air kissed the exposed skin of his hip. Second tape. The front panel sagged forward, heavy and clinging. Third tape. Fourth. The entire diaper finally gave way and dropped between his knees to the floor with a wet, crinkly thud.
His cock cage gleamed under the light, the tiny steel bars barely containing the straining, purple-headed shaft. His balls hung low and dark, bloated from weeks of unrelenting denial. Thick strands of pre-cum stretched from the tip of the cage toward the floor.
Lauren tsked sympathetically. “Awww! Poor thing!! Look how desperate you are...” She traced one fingernail along the bars, making him jerk. “All locked up and leaking for Mommy!!"
She produced the key again, sliding it into the little mechanism as his breath caught. The click of the lock rang like a tiny symphony in the quiet room. The moment the cage released, his cock surged upward. Painfully hard, veins pulsing, tip glistening and slick.
He gasped, hips twitching forward involuntarily, already imagining sinking into Mommy’s welcoming heat after so long.
Lauren caught his throbbing shaft in her palm and gave one slow, torturous stroke. Then she pulled her hand back and let just one fingertip trace lazily up and down his sensitive length, feather-light, maddeningly careful, barely making contact.
“Ohhh, it’s been sooo long since you’ve been inside of a pussy, hasn’t it, honey??” she cooed, her voice dripping with mock sympathy. “Do you miss sliding your widdle nubby inside of something warm and wet? Something other than a diapy? Do you miss making your widdle humpies? Hmm?”
Her fingertip circled the head once, then glided slowly back down to the base and up again, never giving him enough pressure.
“You want Mommy to let you try a pussy again? After watching Daddy fuck me so many times… do you think you can do better now? Hmm? You gonna show me what a big boi you are?”
Randy was trembling, his whole body quaking with desperate need. The light, teasing touches were driving him insane. Every word made his cock twitch and leak in her hand. The fantasy of finally being allowed back inside her consumed him.
“Yes, Mommy!” he blurted out, voice cracking with raw desperation. “Please let me fuck your pussy! Please!”
Lauren blinked, then broke into a wide, amused smile. She let out a soft, condescending scoff.
“My pussy?” She tilted her head, still lightly tracing her fingertip along his throbbing shaft. “You thought you were getting to fuck my pussy? Oh sweetie… that’s adorable!!”
She gave his cock one last gentle tap before pulling her hand away completely.
“No no no, you don’t get to go inside Mommy. That ship has sailed long ago. I said you get to go inside your girlfriend.” Her smile turned sweetly cruel. “But I’m not your girlfriend anymore, am I? No. I’m your Mommy now. I change your dirty diapers, I feed you your num-nums, and I decide when your little cage comes off. But don’t worry… I got you someone else that can satisfy your needs...”
Only then did she slide off the bed with graceful slowness and kneel down. She reached underneath it and dragged out...a blow-up doll.
The cheap vinyl thing emerged with a pathetic creak, glossy plastic skin, vacant blue eyes, permanently parted pink lips. She had inflated it just enough earlier that afternoon to keep it firm but still slightly yielding. She lifted it onto the bed and positioned it carefully against the pillows, legs splayed obscenely, the material squeaking softly as it settled.
Lauren glanced back at him with a bright, innocent smile, patting the doll’s shiny thigh. “Say hello to your new girlfriend, sweetie! Her name is Patty!”
Randy’s hopeful expression shattered in an instant. His shoulders slumped hard, the spark in his eyes dying as crushing disappointment slammed into him like a physical blow. That wasn’t Mommy. It was just cold, lifeless plastic.
Lauren returned to him, reaching into the nightstand drawer and pulling out a small tube of numbing cream. Randy stared past her at the lifeless doll propped on the bed, his freshly freed cock still throbbing uselessly in the air while waves of despondency crashed over him.
She squirted a thick dollop onto her fingers and began spreading the cool cream over his straining shaft, methodical and clinical, working it in with slow, deliberate strokes from base to tip. The numbing sensation spread quickly, turning everything into a frustrating, distant buzz.
Randy’s face twisted into a deep pout. A soft, miserable whimper escaped his throat as he stared at the shiny vinyl doll blankly staring up at the ceiling with its mouth open in an "O". This was what he had been so desperately excited for? This pathetic toy?
“Aww, what’s the matter, baby?” Lauren cooed, still coating him thoroughly, her voice sweet but laced with amusement. “Are you pouting now? After all that begging? Would you rather go straight back in your cage instead?”
Randy’s eyes widened in panic. He shook his head frantically. “N-no, Mommy!! Please…”
She raised an eyebrow, still slowly working the cream along his length. “Then tell me. Tell me you want to fuck your girlfriend. Tell me you want to fuck your little dolly.”
His face burned with fresh shame, bottom lip trembling. “I… I want to fuck my girlfriend,” he whispered hoarsely. “I want to fuck my little dolly… please.”
Lauren smiled sweetly, clearly enjoying his humiliation. “Good boy. Now...I'm going to give you have sixty seconds. One whole minute.” She finished spreading the last of the cream as she spoke. “If you can finish inside Patty before the timer runs out, you get to cum. If not…” She shrugged, her voice dripping with mock sympathy, “back in the cage you go.”
She set the tube aside and reached back into the drawer, pulling out the small egg timer. She held it up between them, twisting the dial slowly with a deliberate click-click-click until it read exactly 60. The plastic device looked almost innocent in her hand, yet it now held his entire pathetic chance at release.
Randy’s gaze flicked helplessly between the timer and the lifeless doll splayed out on the bed before him, legs spread wide, glossy plastic body waiting silently like the only “pussy” he was allowed. His numbed cock twitched in the cool air, desperate and distant at the same time. This cheap blow-up toy was truly his only shot tonight.
Lauren’s lips curved into a knowing smirk as she watched him stare. “Ready, sweetie?”
He nodded so hard his whole body shook, bottom lip trembling with a toxic mix of shame, frustration, and frantic need.
She released her hold on the dial of the timer, and it started ticking.
“Go.”
He scrambled onto the bed, knees sinking deep into the mattress. His shaking hands fumbled to line himself up. The numbing cream made his cock feel like it belonged to someone else, but the ache in his balls was excruciating. After two clumsy thrusts that slid uselessly along the cool silicone, he finally pushed inside. The cheap fake vagina difficult to work into, tight only because of the unyielding plastic.
He started humping immediately, frantic and sloppy, hips snapping forward with raw, animalistic desperation. High-pitched, broken whimpers and moans spilled from his throat without restraint. The doll squeaked and crinkled violently beneath him, the cheap vinyl louder and more humiliating than any of his own diapers had ever been. Every desperate thrust made the plastic body shift and squeal, her lifeless legs flopping bonelessly against the sheets.
Lauren laughed softly behind him, low and delighted, leaning in so he could hear every cruel word. “Oh my god! Listen to you. Humping that plastic slut like it’s the last pussy on earth!! Look at how hard you’re trying for Patty. That’s all you get now, isn’t it, baby? No warm, wet Mommy pussy for my little cuck anymore. Just this cold, fake dolly and sixty pathetic seconds.”
She glanced at the timer. “Actually...now it's forty seconds!” she called sweetly, her voice dripping with amusement as she watched his hips piston faster.
Randy sobbed openly now, the sound mixing with his frantic grunts. He humped harder, more erratically, the bedframe rattling with every desperate thrust. The doll’s glossy body squeaked and protested under his weight. His swollen, purple balls slapped uselessly against the vinyl. The numbing cream made every sensation feel maddeningly distant, yet the deep, clawing pressure in his denied balls kept building anyway. So close, so cruelly close.
“Twenty seconds.”
He was crying harder, open-mouthed sobs pouring out as he drove into the lifeless toy with everything he had. The plastic threatened to pop or collapse under the force of his frantic humping. Tears streamed down his flushed cheeks while pathetic, keening noises escaped him. This was it, his only chance.
“Ten.”
He wailed, body shaking violently, thrusting with wild, jerky desperation. The doll squealed louder than ever. He could feel the edge of release clawing up from somewhere deep inside, right there, almost within reach—
The timer dinged sharply.
Lauren’s hand shot out and yanked Patty away mid-thrust. The doll was ripped from under him, leaving his numbed, throbbing cock slapping wetly against his own stomach. Untouched, denied, still desperately leaking.
“No, no, no, please, please!” Randy’s voice cracked into raw, childish wails. He kept bucking helplessly into empty air, hips jerking in frantic, useless spasms, tears streaming down his face as the orgasm slipped away once again.
“Awww, baby…” Lauren patted his sweat-damp hair while he cried, her voice sweet and soothing but laced with unmistakable mockery. “I’m sooo sorry!" She didn’t sound sorry at all. "You were so close that time! Maybe next time you’ll be a quicker little humper..."
Randy blubbered incoherently, body trembling with overwhelming frustration and shame, still weakly humping the empty air like a broken toy.
Lauren retrieved the cage without hurry. As she looped the base ring around his swollen, aching balls, Randy broke completely. Fresh tears spilling as the familiar, unforgiving confinement returned.
“Mommy, please!” he sobbed, voice high and desperate. “Just one more chance! I was so close. Please give me ten more seconds! I can do it this time, I swear!”
She continued calmly pressing his still-rigid, leaking cock into the tiny steel prison, ignoring his frantic pleas.
“Nooo!! Mommy! Don’t lock it yet!” he wailed, tears pouring down his cheeks. “Please! I’ll do anything! I’ll fluff more than just Marcus’ cock! I’ll suck any cock you want me to! I'll dress like a little princess!! I’ll suck every dick in town!! I’ll be the best little fluffer ever! Just please don’t lock me up again!”
“Shhh, shhh, baby...” Lauren cooed softly, her tone calm and condescending as she worked his throbbing shaft deeper into the cage. “This is for your own good. Back where you belong. You know you can’t be trusted with a free little nubby."
Randy kept sobbing and bargaining through broken hiccups. “I’ll suck them every time… I’ll swallow every load… just give me one more try… please, Mommy!”
She continued to ignore him like he was nothing more than a fussy tottler. "Hush now, honey. Mommy knows best. Good boys stay locked up tight so they don't get silly ideas!"
The lock clicked shut with a final, cruel snick. "There we go!!! Nice and snug! Maybe we'll give you another date with Patty next month. But only if you're on your best behavior!"
Randy let out a devastated wail at the sound of his chance at orgasms clamping shut.
Lauren reached for the discarded diaper, the same cold, clammy, pungent one he’d been wearing all day. The inside was sticky and rank now, the scent sharp and unmistakable. As she slid the heavy, wet padding up between his trembling thighs and pulled the front over his newly caged cock, Randy continued sobbing openly. She didn't even give him the satisfaction of a fresh diaper. Just taped the old one extra tight and snug, so every movement would remind him of his failure.
The cold, wet padding pressed against his overheated skin. Randy cringed visibly, shuddering at the clammy, squishy sensation that immediately soaked through to his cage. The familiar stench of his own stale piss filled his nose as the heavy, mushy bulk settled between his legs.
She had to hold the weight of the soggy bulge upward so it could be contained as she snapped the onesie buttons around it. Even with the fabric holding it, the heavy diaper still sagged noticeably under its own weight. She patted the mushy bulk fondly. “There we go!! All snug again. My perfect, denied little cuck boy!! Still marinating in the same wet mess.”
She gently pushed his pacifier between his trembling, sobbing lips.
“Here, baby. Suck on your paci. That’ll make everything better, won't it?” she cooed, pulling him into her lap and rocking him gently. “Shhh… no more big tears now. This is what you wanted, remember? You were the one that begged me to diaper and deny you. Mommy's just giving her widdle baybee what he always dreamed of!"
Randy sucked weakly on the pacifier, still hiccupping and whimpering softly around it, face buried in her neck as fresh tears rolled down his cheeks. His caged cock throbbing uselessly against the unforgiving, cold, piss-soaked diaper that now felt more humiliating than ever.
Lauren hummed a soft lullaby, smiling into the dim room, already looking forward to how sweet and obedient her little cuck would be with another full month of perfect service...all in hopes of getting another chance at fucking a plastic pussy.
I am so obsessed by Megan Louise, singer of the ultra sexy band Desire.
“Good keep embracing him while it happens. This is an important step for him. He needs to feel your overwhelming maternal energy while he fills the diaper. Don’t let go until he’s all done. Hold him tight and feel free to reach down to his bottom to comfort him and feel his progress. He’s pushing out years of pent up negative pressure and emotions, so it may take some time”