A Sissy Soirée 1+2 (complete)

 A Sissy Soirée

The quiet stillness of Christmas Eve filled the house, but Donna and Gerald were preparing for a different kind of festive evening. Donna had spent weeks planning and purchasing Gerald's new outfit. She was eager to see the delight - and humiliation - that awaited. 

“Let’s get started, Missy,” Donna said with a sly grin, slipping into her dominant persona with ease. Gerald’s cheeks flushed, he nodded, after one glance he was desperate to wear the pink confection Donna had laid out for him.

The dress was a sissy’s dream: a short, frilly number in bright pastel pink, complete with layered petticoats that would quietly ssswsshhh and flounce with his every movement. Donna had even bought a matching corset and pink heels to complete sissies outfit. Donna had made it clear: before Missy could even think about slipping into the outfit, he needed to prepare.

“You’re not touching this dress until you’re smooth as satin,” she declared, handing him a razor and a can of shaving cream. “From face to feet, Missy. No shortcuts.”

As Gerald shuffled off, Donna leaned against the doorframe, smirking. “Honestly, it never ceases to amaze me how much effort you are willing to make sissy. A real man wouldn’t put up with all this fuss. But then again, you’re nothing like a real man, are you?”

Missy was still enjoying Donna’s humiliating comments when he returned all smooth and sheepish. Donna stood ready with the corset. The pale pink satin gleamed under the bedroom lights as she wrapped it around him and fastened the busk, her hands began lacing it inch by inch. “Hold still, Missy,” she commanded as Gerald squirmed slightly. When he let out a small gasp of discomfort, she clicked her tongue in mock disapproval. Inside Gerald smiled in anticipation of the humiliation he knew was coming.

“A little tight, is it? Let me remind you, Missy, a real man wouldn’t be seen dead inside a corset. But you’re not a real man, so you don’t get to complain. I’ll decide when it’s tight enough.”

With the corset cinched to her satisfaction, Donna slipped silicone falsies into the bra cups, giving Gerald a pronounced bust that made him blush even deeper. 

Donna admired the shape the new corset imparted, it cost more than she wanted to spend - but it was for a special occasion.

Next came stockings, she slid them sensuously up his freshly shaven legs and, having hitched all eight suspenders, had him step up into the pink heels.

Did we forget something?” Her voice was gentle but firm, her eyes filled with what Missy recognised as both mischief and wickedness. 

“Please Mistress, can I just wear the clothes tonight?” Missy whined with little expectation she might agree. “I promise not to get hard.”

“I think your little cockette is already hard.” Donna laughed as she picked up the chastity “although it is difficult to tell…” she grasped his balls a little harder than necessary.

Donna liked Missy to watch every time she put him in chastity and turned him to face the mirror. Secretly Missy also loved to watch as he submitted, there were times when the sound of the lock clicking shut would have him dripping pre-cum. 

Donna gently slid the back ring over Missy’s flaccid shaft and pulled one testicle through the ring at a time “did you have a pre chastity wank sissy?”

“No Mistress” Missy lied. 

She carefully guided his flaccid penis into cage. Making sure to align everything correctly, Donna clicked the lock closed. 

Donna smirked at his wincing as she screwed in the urethral catheter and locked it in place.

Missy’s enthusiasm waned. When in Mistress mode Donna inserting his urethral catheter signalled he would not be released any time soon. Donna told him to bend over and Missy obediently grasped his ankles. He felt the cold lube and then the slow stretching as Donna began inserting the plug. 

“Relax for Mistress sissy” Donna cooed as she moved the plug back and forth, a little deeper each time. Just when he felt like he might split in two the widest part passed his sphincter.

Donna released the butt plug and watched as his shrinking sphincter drew the plug fully inside “happy Christmas Missy” Donna giggled.

Missy had a clear view through his legs to the mirror “‘thank you Mistress, it matches my new dress perfectly.” He felt fuller than ever before, the new butt plug filled him to overcapacity and pressed on his prostate when he sat at the vanity. 

Finally, it was time for makeup. Donna leaned in, her touch swift and gentle as she applied an exaggerated combination of blush, eyeshadow, and lipstick. “There we go,” she said, leaning back to admire her work. The effect was strikingly over-the-top, a garish celebration of his sissyness. 

Missy stared at his reflection with a mixture of awe and embarrassment, “if anyone saw me now I would just feint with shame.”

“We both know that is not true” Donna teased as she applied a second coat of the pink plumping lipstick. “Your lips are super plump already!” Donna smirked as she capped the lipstick “

The second coat began to tingle, his lips began to feel rubbery. “Is he coming?” Missy knew he sounded nervous, Jim was a recent addition to the game. And, as far as Missy was concerned, an unwelcome addition.

“We will have to wait and see” Donna said as she picked up his shock collar.

“Please Mistress, not the collar.” Missy whined “I promise I will be obedient.”

“Starting when?”

Missy smiled “I’ve already started Mistress” curtesy 

“Then prove it by locking your collar on, for me.” Donna smirked as she handed him the collar.

His cock strained inside the chastity, Missy loved being manipulated. He locked the shock collar around his neck and turned his attention back to the mirror. “You’ve outdone yourself again Mistress,” he whispered, his voice trembling with both gratitude and submission.

Donna smiled, took a new, long strawberry-pink wig from the closet and situated it carefully on his head. The curls tumbled down to his shoulders, framing his face in a sugary softness of sissyness. “There, now, who’s a sissy princess?”

Missy couldn’t stop admiring himself in the mirror, spinning slightly to watch the petticoats swish around his legs. Donna noticed and tapped at her iPhone - the shock collar tingled level one “stop being so conceited, anger me again tonight and it’s level five.”

“Please Mistress, not five, I soiled my panties when you used level four.”

“Then, as you will not be wearing panties tonight, you best be obedient.” Donna had chosen a dress short enough to give her glimpses of chastity and butt plug as he walked, 'It would be a shame to conceal the devices that prove my sissies total submission inside panties.'"

Missy felt a new level of shame at her words, “Mistress, aren’t you going to change into your costume?”

Donna, still comfortably dressed in jeans and a tee, raised an eyebrow and smiled enigmatically. “Oh, Missy,” she said, her tone dripping with sarcasm. “I’m perfectly dressed for tonight. I wouldn’t want to look overdressed next to you, now would I?”

Her words hung in the air, both a tease and a promise, as she led the way downstairs, leaving Missy to totter behind, the pink heels clicking on the hardwood floor.

***

Donna glanced at the clock and smiled. It was nearly time. In the living room, Missy fussed around making sure festive Christmas decorations were just so before they settled in front of the television. The soft glow of fairy lights twinkled from the tree in the corner

.

“Are you sure you’re ready, Missy?” Donna asked, stepping closer to adjust the lace trim on his dress. 

“Yes Mistress,” curtsey. At the beginning of role-play Missy’s heart always raced, his nerves always tingled with excitement. 

“Then we will begin”

***

The doorbell rang, and Missy’s breath caught, “who is it Mistress?”

“Remember level FIVE” Donna tapped at her neck. 

“I will not forget Mistress” curtsey. Missy nodded 

 

“Relax sissy,” Donna swept to the door, confident Mistressness radiating from her every move. “Remember, smile, serve, and let me handle the talking. This is going to be fun.”

Donna opened it to greet Angelina and Molly, her best friends since schooldays, both wore cozy, night in, sloppy sweaters and carried bottles of wine.

“Donna, you’ve been acting mysterious all month!” Molly teased as she stepped inside. “What’s this big surprise?”

Angelina followed, her eyebrow quirked. “Yeah, you’ve got us dying of curiosity. What’s going on?”

“Ladies,” Donna began, ushering them into the living room, “I’d like you to meet someone very special to me.” She turned to the hallway. “This is Missy the Sissy, darling, come say hello!”

Missy was frozen to the spot, Angelina and Molly stepped into the room, his cheeks pinker than his dress. Balancing the tray carefully, he curtsied. “Good evening, Miss Angelina, Miss Molly,” he said, his voice soft and demure. 

Angelina and Molly were the epicentre of their social group, that moment sissy play became public knowledge. 

The room fell silent for a moment as Donna’s friends stared. Angelina’s mouth opened slightly, while Molly blinked as if trying to process what she was seeing.

Donna beamed. “Missy is my devoted sissy and companion. Isn’t she just adorable?”

“Wait - what?” Molly finally said, her laughter bubbling to the surface. “Donna, this is priceless.”

Donna settled into the armchair with a theatrical flourish. “Missy, darling, serve the ladies some refreshments.”

Missy hurried to the coffee table, settled the tray of glasses down and poured wine with trembling hands. Angelina leaned back, crossing her arms. “Okay, Donna, you’re going to have to explain this. What exactly is a ‘sissy,’ and why is Gerald - sorry, Missy - dressed like this?”

Donna’s eyes sparkled as she leaned forward. “A sissy, my dear Angelina, is a man who embraces femininity and submission. Missy here is a perfect example. She loves to serve, to look pretty, and to obey. Isn’t that right, Missy?”

“Yes, Mistress,” curtsey, Missy murmured, his  head bowed as he handed Molly her glass of wine.

“This is… an elaborate prank, even for you” Molly said, her tone skeptical but amused. 

“Oh, this is no prank.” Donna smirked.

“Give it up Donna, even my boyfriend would dress up like that if I told him he could have a months free pass.” Angelina said mockingly

“Exactly,” Molly added. “This is your best prank in an age. If it is not a prank, as you claim, then convince us this is real.”

Donna’s smile didn’t waver. “Oh, I’ll prove it. You’ll see soon enough.” Donna’s fingers danced across her iPhone.

***

“I’m getting flashes of something metallic!” Angelina exclaimed. “What is that Missy?”

Missy blushed, stayed still until Donna told him to lift his dress. 

“It is a chastity belt, a sissy is not properly dressed until he is in chastity and plugged.” Donna said.

Missy moved closer to display his chastity to their guests. “Go ahead, have a good look.”

Molly went first, had a tug at the chastity. 

Angelina looked with the intensity of an entomologist discovering a new species of beetle on a sunny day “what is that screwed in the end?”

“It is called a Urethral Catheter.” Donna explained it locked in place, provided an extra layer of  control. “Control and humiliation have one thing in common - a sissy can never have enough of either.” Donna circled a finger in the air and, as if there were invisible pulleys and drive belts involved, Missy turned 180 and leant forward to obediently display his butt plug.

“It has a pink jewel that matches his dress” Angelina enthused as if no one else would have noticed.

“Every little detail…” Molly chuckled “I’ll give you guys ten out of ten.”

***

Fifteen minutes later, the sound of a car pulling into the driveway signalled Jim’s arrival. The friends exchanged glances, their curiosity now piqued. The door opened, and Jim stepped inside - a tall, confident man with an easy air of authority. Without hesitation, he leant over Donna and kissed her deeply.

“Oh my God,” Molly whispered, wide-eyed.

“My boyfriend would not let me go that far on a prank.” Angelina sounded shocked but amused.

Donna gave Jim a warm smile, her eyes shining with a mixture of affection and pride. "Ladies, allow me to introduce Jim, the man who has become a key part of our life," she said, her voice laced with excitement. "Jim, this is Angelina and Molly, my best friends."

Jim smiled at the two women, offering a polite nod. "Nice to meet you," he  said, but his gaze quickly shifted to Missy, still standing in her frilly pink dress before the coffee table. “I’ll take some whisky Missy.”

Missy swallowed, he glanced at Donna who had her iPhone in her hand. Missy poured his drink, handed it to Jim. Missy’s hand trembled, the surface of the whisky shimmied as if there was a tiny, whisky glass sized earthquake in progress. Donna smiled “what do you say now Missy?” 

“Your drink, Master” curtsey. Missy said. Submitting to Jim in private had been humiliating enough. The humiliation of submitting to Jim in front of Angelina and Molly would last a lifetime.

Angelina and Molly exchanged smiles, both still certain Donna and Gerald were pranking them. Molly said what they both thought “I can’t imagine how much planning all this must have taken Donna."

“Honestly, Molly, I promise this is not a prank.” Donna giggled, pleased with the hint of uncertainty on her friends face. “I even make Missy submit to a real man.” 

Angelina’s eyes widened, and she exchanged a look with Molly. "So, NOW, you’re claiming that... he -“ Angelina gestured to Missy, "submits to a ‘real’ man, what exactly do you think a real man is?”

Donna’s smile never faltered. She leaned back in her chair, a hint of satisfaction in her posture. “Not my sissy, Angelina, no real man would subjugate himself like this. You see, Missy here has chosen to submit, to be ruled by me and my boyfriend, a man who knows how to take control. Jim is a real man - someone who commands respect and isn’t afraid to take what he wants."

Molly, still looking skeptical laughed “you sound so convincing. I just cannot believe you took the prank this far. And you Gerald, I mean how could you let them make out like that?”

Angelina laughed as Molly spoke “Even when Jim came in Gerald stayed in character! They certainly had me going. QUALITY or what?"

Inside Donna seethed with anger but kept her voice soft and calm. The evening was turning into a farce, her friends treating it like a joke instead of the carefully planned event she envisioned. Determined to regain control, she resolved to show them just how much power she held over both men. 

Donna smiled toward Missy “Jim, have you got Missy’s present with you?”

“Of course.” Jim smirked. 

Missy looked at Donna, her repeatedly warning Missy of level five now made more sense. He could see the obedience app open on her iPhone, he glanced at Angelina and Molly. 

Jim stood, smiling as he noticed Angelina and Molly watching in the way a cat stares at a moth “Come closer Missy” Jim pointed at his feet, he looked briefly at Donna who was now discreetly videoing the scene from knee level.

“Master?” curtsey. Missy said as he stood before Jim.

Angelina discreetly nudged Molly with her elbow, smiled, whispered “what now?”

Molly shrugged.

“Kneel” Jim said softly. Missy knelt, Jim said “go ahead, open your present.”

Missy saw the shocked look on Angelina and Molly when he unzipped Jim and took out his cock. Jim had taught Missy the best blow jobs are the wettest blow jobs. Missy slathered Jim’s impressive cock from base to tip while concentrating on Jim’s head and frenulum.

Like her friends, Donna could barely believe her eyes. She’d had Missy on his knees before Jim plenty. Never with an audience. Never with below-zero resistance. Donna admired Missy’s enthusiasm for public performance.

Missy bobbed back and forth like he just don’t care. 

Donna checked Angelina and Molly were focussed on Jim and Missy. She quietly lowered her zipper and slipped her fingers inside her sopping wet cunt. 

Missy took half breath, opened his mouth a little wider. Missy sucked on Jim’s cock letting it slide past his tongue and deep into throat. The first time he had deep throated Jim had been scary. Missy now trusted him, Jim was not the sort of guy to hold his head. When Missy moved back to tonguing he was just able to see Angelina and Molly. The remnants of Missy’s shame evaporated when he saw Angelina had a hand inside her skirt and Molly’s eyes flicked from blowjob to Angelina to blowjob and so on. 

Missy focused his tongue on Jim’s frenulum just enough to edge him. 

Molly and Angelina left embarrassment in the rearview and settled in to enjoying the live show. Molly, let out a soft nervous laugh as she lowered the zipper on her jeans. The last time Donna, Angelina and Molly had masturbated as a team they had been teenagers. 

A soft moan escaped Molly as her third finger slid in, ”I have to admit, I never imagined I’d see a show like this tonight. Your sissy is really is into it."

Donna smiled, “next time we’ll make it a girls night, Missy also has a way with rosebuds.”

Missy greedily swallowed down his Christmas present.

PART 2

Let’s get started, just relax Gerald,” Donna said with a sly grin, slipping into Mistress persona with ease. “I know so much changed recently, there is no need to feel anxious.”

Gerald’s cheeks burned as he stood before her, as hairless and naked as the day he was born, waiting. No matter how many times they indulged their weekend fantasies, Donna always found ways to push him further, tonight, her tone carried an edge that made him feel particularly nervous.

“Jim’s gone now,” Donna continued, as if she could read his thoughts. Now,  without Jim, there was a void Donna was determined to fill with something even more intense. Her words were casual, but her smile was sharp. “You should be happy now it’s just the two of us again. But that doesn’t mean I’ll go easy on you, Missy.”

Jim - he name still haunted Gerald’s waiting-for-sleep mind, as did memories of Donna flaunting her control. Some nights, when Gerald dreamed, he woke in a sweat with the taste of Jim’s cum in his dry mouth and sounds of Donna’s humiliating words ringing in his ears.

Donna picked up Missy’s pink corset from the bed. It was new, designed to cinch Gerald’s waist down to an exaggerated hourglass. She held it up, inspecting it with mock seriousness. “Straight from Japan,” she said. “You’re going to look so adorable. Now, arms up, Missy.” 

Gerald obeyed, Donna wrapped the corset around his torso. The thick, new fabric was stiff, the laces impossibly tight as Donna worked to secure it. Each tug stole a little more of his breath, the constriction forcing him into a posture that felt both unnatural and intoxicating.

“There we go,” Donna said, giving the laces one final long pull before tying off. “Perfect. Now who needs a pair of nice big titties?.” She said before sliding the D-cup forms into the cups of the corset. “Oh, Missy, look at you. You’re practically bursting out of it. Such a shame - not a real man, not even a real woman. Just a pathetic little sissy.”

Gerald, now Missy, lowered his eyes, his cheeks flaming at her words. He felt a delightful mix of shame and exhilaration coursing through him. Donna loved to wield her power like this as much as Missy loved to surrender to her.

“You’re going to look so pretty tonight,” Donna said, her tone shifting to one of faux sweetness. “But don’t get too comfortable. This isn’t for you. Oh no, Missy. It’s for whoever I decide to show my sissy husband off to.”

Missy’s breath caught. “Who is coming Mistress?” Donna had put in so much effort that it just had to be someone new. The thought was scary and thrilling in equal measure. 

Donna basked in his delightful neediness and smirked. “Oh, don’t worry, Missy Sissy. This keeps you on your best behaviour.” Missy squirmed when Donna lowered his panties and tugged his chastity. The chastity had been a constant reminder of submission for over a month. “Oh, Missy, look your cockette is only part dressed” Donna smirked at his wincing when she screwed in the urethral catheter and locked it in place. She added a sanitary pad to his panties with a flourish, a mocking smile playing on her lips. “I do not want you leaking  if you see a real man.”

Adding the urethral catheter after starting his chastity made it crystal clear  Gerald would not be getting any wank-time in the foreseeable. She told him to bend over and Missy obediently grasped his ankles. He felt the cold lube and then the slow stretching as Donna began inserting the plug. “Relax for Mistress Missy” Donna cooed as she gently moved the plug back and forth, a little deeper each time until the widest part passed his sphincter. Savouring the moment she delayed releasing the butt plug, a quiet squeal of delight escaped her as she watched as his sphincter draw the plug fully inside “there, back door closed” Donna giggled.

The new corset was so long, so tight, so heavily boned, that Donna needed to slide his white stockings up his legs, she stepped back to watch Missy hitch the eight suspenders. “I was telling June next door what nimble fingers you have” Donna teased as she held up her iPhone “I could invite her round to see for herself.”

“June is coming here… tonight?” Missy swallowed “please Mistress, June is such a gossip, if she sees me everyone for miles around will know.”

Surely this can not get any better Donna said to herself - then she had an idea and giggled, “do you worry Angelina and Molly might have told people…”  She slowed the scene by saying it was time for makeup. Donna leaned in, her touch swift and gentle, soon layers of blush, eyeshadow, and lipstick gave an over-the-top, garish look she always created for her sissy. As she worked Missy became serious, almost slipping out of character. “What? You didn’t tell them what happened in the house stays in the house Donna?”

“Me? Did you ask them for secrecy? No! So, there is a chance mutual friends might know about Missy. Has anyone mentioned anything to you?” Donna kept her iPhone running, Angelina and Molly would love this! 

“No Mistress, perhaps Angelina and Molly did not tell anyone” Missy slipped back into character. He was enjoying her new humiliation technique - in fact  Missy LOVED it! 

 

“Well…” Donna gave a little smile as she guided him into the pink high heels waiting nearby, the added weight of the bigger breast forms forcing him to adjust his balance. By the time she unveiled the dress, Missy would be trembling with anticipation. “perhaps… one of them might’ve.” 

Almost more than anything in the world Missy wanted to see the dress - so much that he almost missed ‘perhaps… one of them might’ve’ 

“Mistress, why perhaps?”

His frightened look was to-die-for. Donna said “at the coffee shop Joan mentioned Christmas, asked several times if I had any pictures of our decorations. I showed her the tree and…” Donna paused, watched Missy’s adams apple bobbing up and down “she showed Mai the tree picture.”

“The tree, nothing else?” Missy asked

“Well, you know Mai and June. They went scroll, scroll, scroll before I could stop them.” She chuckled “both said how cute my sissy looks.”

“Mai? Mai knows? Oh my god, that means Tom at work knows… fuck!”

Donna thought how Missy looked to be on the verge of pissing his panties, she smiled inside, thought thank goodness the sanitary towel is a maxi. When she did the big dress reveal, he gasped, all worries over who knew what and when no longer mattered. The dress was everything he had dreamed of and so much more:  

Soft pink with delicate white lace, the hemline scandalously short, ending mid-thigh. Missy’s gasp was involuntary, and Donna’s grin widened at his reaction.

“Oh, you love it, don’t you?” she teased. “Go on, sissy say it. Tell me how much you want to wear this sissy dress.”

“I… I want to wear the dress more than anything,” Missy mumbled, barely above a whisper.

“Tell me you will do anything if I let you wear it.”

“Please Mistress, I want to wear it!” he begged, guessing Donna had some humiliating plan. The dress would multiply the humiliation by a factor of ten - or perhaps twenty Missy hoped.  “if you let me wear it I will do anything you say.”

“Even let Joan and Mai see a picture of it being worn?”

“They know about this?” Missy waved at the dress

“I was so excited when they discovered Missy, I just had to tell them!”

Missy wanted to prove himself, whatever the cost. “They could… I mean if you want… come see the dress for themselves.”

“Good girl,” Donna purred, slipping the dress over his head and smoothing it into place. The fabric hugged his corseted body perfectly, the skirts flaring out with every slight movement. Donna added the finishing touch: a pageboy-style brown wig that framed his face. When she stepped back, her eyes gleamed with satisfaction.

“Look at you,” she said, spinning him toward the mirror. “There’s no mistaking it now. You’re a card carrying, one-hundred-ten percent sissy.”

“110% - that is the absolute minimum Mistress” Missy stared at his reflection, the image mesmerising. 

Thoughts of Joan and Mai swirled around in his head. 

Thoughts of Mistress ushering Joan and Mai, and even Tom, into the lounge room, saying ‘ladies I’d like you to meet someone very special to me. this is Missy the Sissy, darling, come say hello! - just like Mistress said that night Angelina and Molly visited.

“Now, make yourself useful,” Donna said, snapping him out of his daze. “Go into the kitchen and make some tea. Spill anything on that dress you’ll regret it.”

He almost reached the doorway “aren’t we forgetting something?”

Missy looked at the shock collar on the vanity. It was new, Donna called it a ‘dress collar’ - on the vanity the confection of pink and lace looked as innocent as a sleeping Coral Snake. Around his neck the shock collar was just as terrifying as a wide awake Coral Snake.

Now wearing his new sissy dress he did not want to delay the swishy swish of walking to the kitchen, Missy obediently locked the ‘dress collar’ around his neck.  

Skyscraper heels clicked in time with the sssshywussness of petticoats as he carefully made his way to the kitchen. As he busied himself making the tea, he heard Donna moving around in the bedroom. When she finally appeared, the sight of her made him freeze.

She was stunning, dressed in the sleek little black dress that buttoned down the front and hugged her curves. Her makeup was flawless, her heels adding an air of sophistication. She looked every bit the powerful mistress. “Mistress” Missy just could not let the moment pass without a deep curtsy and his petticoats rewarded the curtsy with a sssshywussness.

“Well, just look at us,” she said, leaning against the doorway with a smirk. “Mistress and sissy - all dressed up with nowhere to go.”

***

Missy’s heart raced, but before he could respond, Donna’s phone buzzed on the counter. She picked it up, a sly smile spreading across her face. “Oh, perfect timing,” she said, her eyes sparkling with mischief. “Our taxi is outside.”

“Taxi?” Missy’s voice wavered, panic creeping into his tone.

“That’s right,” Donna said, grabbing her purse. “We’re going out, Hotel Excelsior in Ashminster, Missy. It’s time I showed you off properly.”

Missy’s legs felt like lead as the reality sank in. He’d never stepped foot outside in his sissy dresses before, and the thought of doing so now made his stomach churn. “Mistress, please…” he started, but she cut him off with a sharp look.

“What did you promise?” she asked, her voice cold and commanding. “I will do  anything Mistress - that is what! You’ll do as you’re told or it is obedience collar time, Missy. Now, let’s go.”

The ride through Ashminster passed in a blur. Missy sat stiffly in the backseat, his cheeks burning as the taxi driver’s eyes flicked to the rearview mirror. Donna, on the other hand, was the picture of confidence, chatting lightly about their destination as if nothing were out of the ordinary.

When they destinated at Hotel Excelsior, Missy hesitated, his hand frozen on the door handle. 

“Sorry driver, this is my husbands first time in public.” Donna leaned over, her voice low and teasing. “Don’t keep the driver waiting, Missy. Be a good sissy and step out.”

With a deep breath, Missy obeyed, heels clicking against the pavement, a new experience, had a calming effect. The hotel’s grand facade loomed above them, and Donna’s hand on his arm guided him forward. Inside, the opulent lobby heightened his sense of exposure.

At the bar, they took seats at the sleek, modern stools. The bartender approached, his eyes lingering on Missy’s outfit. “Evening, ladies,” he said with a grin. “Going to a fancy dress party?”

Donna’s smile was as smooth as silk. “Oh no, nothing like that,” she said, her tone light but dripping with amusement. “Missy just likes to dress this way. Isn’t it adorable?”

The bartender’s eyebrows lifted slightly, but he nodded. “Well, you certainly make an impression,” he said, turning to mix their drinks.

Missy’s face burned, but Donna’s hand on his knee steadied him. Her grip was firm, a silent reminder of who was in control. As the bartender  returned with their drinks, Donna raised her glass in a toast.

“To new adventures,” she said, her eyes locking with Missy’s. “And to being exactly who you are, no matter what anyone thinks.”

Missy’s lips trembled as he raised his glass. “To new adventures,” he echoed, his voice barely audible. The humiliation was overwhelming, but beneath it all was a thrill that he would live off for weeks. Donna always knew how to push his limits - and he loved her for it.

“From the two guys at the end of the bar,” the waiter said, placing another round of drinks down on the bar. Donna smiled at Missy, amused. The men looked around their age, early thirties, business men away from home. Missy and Donna exchanged glances, and Donna couldn’t help but tease a little.

“What do you think, shall we invite them over,” 

Missy’s lips trembled slightly as he forced his voice into a feminine register, a quiet protest hidden beneath his nerves. “I don’t think that’s a good idea.”

“Oh, come on,” Donna laughed softly, brushing a strand of hair away from Missy’s face. “I think it will be fun.” She turned her attention back to the men for a moment, smiled, her flirtation casual but deliberate. Missy, focused on keeping his voice soft and feminine when the men joined them.

The evening wore on and the men grew ever more friendly. At the end of the night, the men bid them farewell, casually mentioning that they often stayed at the Excelsior.

Donna could see Missy’s look of relief, but she was determined to push the boundaries further. “We’ll walk you to your elevator,” she said to John and Alan with a playful smile, her hand resting lightly on Missy’s arm.

As they made their way toward the elevator Alan suggested, his voice smooth and confident, “How about a nightcap in my room?”

Before Missy could decline, Donna nodded in agreement. “That sounds like a great idea,” she said, and as the elevator doors slid shut, she turned to Alan and he was on her like a polar bear on a seal. Donna out a hand on his neck and they locked into a deep kiss. Missy felt his cock straining at his chastity while he John watched.

.

The elevator ride up to Alan’s room was thick with tension, the air charged with an unspoken understanding. John ducked out saying he was tired, had an early start. Donna, still smirking slightly, settled onto the sofa next to Alan, casually chatting with him. Missy, though uncomfortable tried to keep his composure by sitting stiffly across from them.

Donna laughed softly. “Don’t let Missy watching bother you Alan, we talked it over before we came to your room. Missy prefers watching.”

Alan hesitated briefly, then nodded. “If you’re sure.” Donna and Alan resumed making out, their kisses growing deeper and more passionate.

Missy’s heart raced as he watched Alan’s hand slide over Donna’s body, exploring her curves. When Alan began caressing Donna’s breasts through her dress, she glanced at Missy, a teasing smile on her lips. “You enjoying the show, Missy?” she purred. “Want to join in?”

Missy shook his head quickly, his voice faltering. “I’m fine watching.”

Donna smiled when Alan started unbuttoning her dress down to the waist revealing her bra. With a flick of her shoulders she let her dress fall about her waist and removed her bra. Alan didn’t hesitate, he leant in to kiss and suckle her breasts. Missy’s breath deepened, a warmth soaked his sanitary towel. 

When Alan’s hand slid up Donna’s thigh beneath her dress, Missy felt a pang of jealousy mixed with something else he couldn’t quite name. The warmth spreading in his sanitary towel named that feeling as cum. Donna pushed Alan’s hand away gently. The second time he tried, she slapped his hand away and moved away along the sofa, laughing lightly.

“Kissing is fine, Alan” Donna said, holding up her left hand to show her wedding band. “But I’m a married woman.”

John pulled back, his expression apologetic. “I’m sorry,” he said, his voice sheepish. “I got a little overexcited.”

Donna’s gaze dropped pointedly to the obvious bulge in John’s pants. She smirked. “I can see that,” she teased.

Alan grinned, leaning forward slightly. “Maybe you could help release the tension?”

Donna feigned shock, placing a hand over her chest, purposely displaying her wedding band. “I can’t touch another man’s cock - I’m a married woman and Gerald would not like it.” She turned toward Missy. “Did you notice Missy isn’t wearing a wedding band Alan?”

Alan’s eyes lit up, his grin widening. “I’d be okay with that,” he said eagerly as he undid his belt.

Donna held up a hand. “We’re not talking sex here, just a hand job.”

Alan tilted his head, considering. “Meet in the middle?” he suggested, a playful smile on his lips.

Donna chuckled. “Blowjob it is.”

Missy’s pulse quickened as Donna pulled him aside, out of John’s hearing.

Missy’s voice wavered. “I don’t want to…”

Donna cut him off, her tone firm. “Fine, I’ll tell Alan my husband is not in the mood”

Missy froze, the weight of her threat sinking in. After a moment, he nodded reluctantly. When they returned to Alan on the sofa, Donna’s expression was all confidence. “Kneel down, Missy,” she commanded, her voice leaving no room for argument.

Missy hesitated briefly before obeying, sinking to his knees in front of Alan. Donna leaned back on the sofa, pulling out her phone. “Let’s document this, Missy,” she said, aiming the camera at Missy.

As Missy began, Donna’s voice was a steady stream of teasing encouragement. “That’s it, Missy. Show Alan your moves.”

Alan groaned in pleasure. Donna’s soft laughter filled the room, she captured the moment with the confidence of a woman documenting a cup of coffee for her social page. 

When it was over, Donna set down her phone, her smile triumphant. “Good job, Missy,” she said, patting Missy’s shoulder. Missy avoided her gaze, a storm of emotions swirling within him.

Alan leaned back, exhaling contentedly. “You two are something else,” he said with a grin.

Donna merely smirked, her eyes gleaming with satisfaction. “Oh, Alan, you literally have no idea.”

***

Sunday morning, the aroma of fresh coffee wafted through the kitchen as Donna stood at the counter, humming softly. “Morning, Missy,” 

“Look, no dress, it’s Gerald, that is what we agreed. I can’t believe what you made me do last night,” he said, his voice low but tense.

“Made you?” Donna repeated with a giggle, setting down her mug. “Come on, you were all in.” She grabbed her iPhone, tapping a few buttons, and suddenly the widescreen on the wall lit up.

Gerald’s stomach dropped. There he was, in full resolution, kneeling before Alan, his movements unmistakable. Donna laughed as the video played, her eyes sparkling with amusement.

“Look at you,” she said, pointing at the screen. “So eager! I am literally dying to show Angelina and Molly. ”

Gerald’s face burned “stop the video, I’m in Gerald mode” he swept his arms over his bathrobe.

“Then open your bathrobe, prove you are in ‘Gerald’ mode” Donna raised an eyebrow, smirking. She grabbed at the bathrobe “does my husband Gerald always wear a pink corset beneath his bathrobe?”  

“Look Donna, I was tired. I only sucked Alan’s cock to get it over with, so we could come home.”

“Oh, come off it, Missy. You swallowed Alan’s cum like it was your favourite flavour ice cream. And that bit where you tongued his frenulum? That was a move even I don’t have in my playbook.”

Missy’s jaw tightened. “Please stop calling me Missy.”

“Then take the corset off” Donna’s smirk deepened. “Or do you want Mistress to help you put your new dress on? Is this what this is about?” The video looped, starting over again. Donna’s laughter bubbled up as she grabbed her phone, which had just chimed. She read the message, her grin widening as she tapped out a reply.

“What’s so funny?” Gerald asked.

“Oh, nothing,” Donna said, her tone light but loaded. “Just Alan letting me know they are still at the Excelsior.” She held up her phone so Missy could read the message: “Okay, 8 o’clock. Meet at the room, then we can all head down to the bar.”

Missy’s heart pounded. “I’m not going. Last night was a one-off. Alan will expect me to” He trailed off, unable to finish the sentence.

Donna tilted her head, studying him. “Are you totally refusing to please your Mistress, Missy?”

“It is Gerald” his voice cracked. “You just want to see Missy on his knees again.”

“Ooh, sneaky. I like the way you third-personed Missy” Donna set her mug down and crossed her arms. “If you really do not want to wear your new sissy dress you’re welcome to stay home,” she said casually, “but I’m going to the Excelsior. You can sit here and worry about who I’m sending this video to.” She waved a hand at the wall screen, where the video continued to play. “I bet your coworker, Mai’s husband, what’s his name… Tom? He would love to see this.”

Geralds’s blood ran cold. “You wouldn’t.”

Donna’s grin was wicked. “Try me, Missy.”

***

Missy relaxed during the taxi ride to the hotel, he sat tall in the backseat, meeting the driver’s occasional glances in the rearview mirror with a practiced smile. Donna chatted about their destination as though they were on the most ordinary outing. Destinating Hotel Excelsior Missy stepped out of the taxi with the confidence of a sissy in control. Missy was not going to be dragged along, he had secretly decided to make Mistress proud - prove she did not need a punishment collar to control him. Donna’s approval of obedient Missy evidenced by the satisfied curve of her lips. He walked beside Donna toward the elevator. She had expected Missy to require threats, he had protested so long and hard before the taxi arrived she reminded Missy the promise he made - if you let me wear this dress I will do anything you say.  

She glanced at him as they neared the room. Expecting Missy to make a break for it, at any moment, she fingered the obedience app on her iPhone. Donna knocked on room 451, a sly smile playing on her lips.

The door opened, Alan’s face lit up with a wide grin. “Come in, come in,” he said warmly, stepping aside to let them enter. Alan excused his bathrobe “running a little late.”

Inside, John, also wearing a bathrobe, was pouring tea. He greeted them with a nod and handed Donna a cup. “Tea?”

“Sure, thanks,” Donna said, taking a seat. She gestured for Missy to sit beside her, Missy perched awkwardly on the edge of the sofa remaining silent.

After some small talk, Donna set her cup down. “Missy’s a little on edge,” she said with a teasing smile. “Coming straight to the room and all, we were just talking in the elevator about what you guys might be expecting.”

Alan chuckled, trying to smooth things over. “Hey, last night we were all a little drunk. I did mention we kissed , I hope that is okay Donna.” He glanced at John. 

Donna laughed. “Oh, I’m guessing John knows exactly what went on.” Her gaze flicked to John, whose bathrobe failed miserably at erection concealment. She raised an eyebrow and sipped her tea. “Well, as you’re both ready, Missy might as well get started. Like I said in the text, it is fifty each, we’ll call last night a free trial.” The guys opened their wallets.

Missy’s stomach churned as Donna turned to him. “Okay, Missy,” she said, her voice honeyed but firm. “Don’t keep John waiting.”

Missy knelt in front of John. Donna leaned back, her phone angled perfectly to capture the scene.

As Missy began to bob up and down, Donna’s voice was calm but teasing. “That’s it, Missy, show John your moves.”

The men encouraged him, their voices blending with Donna’s occasional soft chuckles. When they were done, John and Alan dressed, and the group made their way down to the bar as though nothing had happened.

***

The evening seemed to vanish in the blink of an eye, the hours slipping away faster than anyone wanted. Donna and John occasionally leaned into little whispery exchanges, their hushed words punctuated by stifled giggles. Later, John and Alan shared a similar moment, their heads bent together conspiratorially.

When Missy returned from the restroom, the trio was huddled in a lively discussion. As he neared the table, their conversation abruptly ceased, leaving an awkward silence hanging in the air as he sat down.

Around 10 p.m Alan’s face suddenly lit up with excitement. He shot a finger across the room. “Hey, John, look! There’s Reg and Donald!”

John waved them over, his grin widening. “Hey, Reg! Donald! Join us. This is Donna, and this”  - he paused with a chuckle - “is Missy.”

Donna greeted them warmly. Missy welcoming Reg and Donald with a dazzling smile momentarily threw Donna.

After a round of drinks, Donna leaned over to Missy. “Restroom?” she said softly, and they excused themselves.

Inside, Donna practically buzzed with excitement. “You know why Reg and Donald suddenly showed up, right?”

Missy nodded “Alan or John called them.” 

Donna’s grin stretched even wider. “Exactly. And, forgetting your collar for a moment, with all the videos I’ve got on my phone, you’re in no position to back out Missy.”

Missy’s cheeks flushed a deep red. “Just tonight, once only, Donna. After this, we’re never coming back here again.”

Donna tilted her head, pretending to mull it over. After a beat, she nodded. “Agreed,” she said with a sweet smile, though the glint in her eye betrayed her lack of sincerity.

Back at the table, Donna took charge, her voice firm as she laid down the ground rules. “Here’s how this is going to work,” she began, looking each person in the eye. “No making out with me, the door stays unlocked, and no one lays a hand on Missy. Agreed?”

Donald leaned back in his chair, one eyebrow arching high. “How much?” he asked bluntly.

Donna barely suppressed a triumphant smirk. “Fifty a man per blowjob.”

The guys exchanged glances, shrugged, nodded, reached for their wallets. Donna’s confidence soared. Not only had she transformed Missy into a cock-sucking sissy, but now she was pimping him out for the second time in one day - this was no longer just a game. Missy could not even see point of no return from where Donna had taken him.

***

In room 451, the atmosphere was relaxed. John, Alan, Reg, and Donald sat around the room their earlier laughter replaced with whisky sipping anticipation. Donna stood, her eyes glinting with purpose. She motioned for Missy to follow her. "Come with me," Donna commanded, her voice firm, though it contained more than a hint of amusement. Missy saw the men laughing about something as the bathroom door clicked shut behind them. 

The guys talked softly “She’s really gonna do it,” John said, his voice hushed but excited. “Donna’s got him right where she wants him. Poor bastard has no idea what’s coming.”

“Walked it the bathroom like a lamb going to slaughter.” Alan chuckled, taking a sip from his whiskey. “Uh-huh, but Donna knows exactly what she’s doing, said she’s been itching to put her little pet in his place for weeks.”

Across the room, Donald raised an eyebrow “I don’t know,” he said, shaking his head. “Exposing her own husband? That’s a hell of a step. I’ll bet fifty she loses her nerve.”

“Fifty? You’re on,” Alan shot back with a confident grin.

Reg, watched the exchange with a small smile, swirling his drink. “This’ll be a night to remember,” he murmured. “If Donna pulls this off, it’ll be the ultimate display of dominance.”

***

Donna’s eyes gleamed with a predatory satisfaction as she stepped closer, a makeup removal pad in hand. “The guys want to see the real Missy, and so do I” her voice as smooth as silk but laced with steel. She cupped Missy’s chin, her touch firm yet unhurried, she began wiping away his carefully applied makeup with slow, deliberate strokes.

“Is this what you and Alan were whispering about at the bar Mistress” he asked, his caged cock hardened under the weight of humiliation. When hot cum began leaking from his chastity he was thankful for the sanitary towel.

Donna’s lips curved into a wicked smirk as her eyes locked onto his. “Why, yes, darling. That’s exactly what we were discussing,” she said, her tone dripping with mockery. “You said you’d do anything if I let you wear that cute little sissy dress.”

Missy caught the all-too-familiar edge in Donna’s voice - the cold, commanding tone she always used just before activating his shock collar. A shiver ran down his spine, but a spark of defiance flickered. He couldn’t resist testing her limits one last time. With a hesitant, almost pitiful whimper, he murmured, “Mistress… we could just give them their money back.” His words were soft, his tone laced with just enough sincerity to mask the deliberate tease. It wasn’t just resistance any more - it was a subtle, dangerous, sissy game - a push to see how far she’d go.

Donna paused, her eyes narrowing as she leaned closer, her voice dropping to a menacing whisper. “Refund? Oh, sweetie, they’re not interested in a refund.” She cupped his face more tightly, forcing him to meet her gaze. “This is the show we all came to see: my sissy husband, Gerald, kneeling before four real men and proving exactly what he’s good for.”

Missy moved his thighs to test his sanitary towel for leaks. Confident he had gotten all the humiliation the bathroom situation offered he opened the bathroom door and walked confidently across the room. If Mistress wanted a show then, by fuck, Missy was going to deliver the performance of a lifetime.

“you guys got numbers like at the deli counter or shall I just start at the left?”

***

Donna was turning the scene into one of those arthouse style fly-on-the-wall documentaries. Her lens captured every humiliating detail, every hint of enthusiasm on Geralds’s face, and every pleased smirk on the men’s. Donna’s recording never wavered, her voice occasionally chiming in with mocking encouragement or sharp instructions. The earlier videos were already potent tools, footage of a sissy who looked strikingly like her husband was powerful enough.

But this? This was something else entirely. Footage of Gerald, unmistakably her husband, dressed in a garish sissy outfit and servicing four men in turn, elevated Donna’s leverage to an entirely different level. It wasn’t just control anymore - it was absolute domination.

With Reg and Donald in the bag Gerald started to approach his task with ever increasing confidence, settling onto his knees before Alan he teased Donna by smiling directly into camera and licking his lips “Mmm, cock.” His lips parted hesitantly before closing around Alan’s thick cock, his mouth sliding down until he gagged slightly. “That’s it Gerald, balls on chin. You getting all this Donna?”

Donna zoomed in as he found a rhythm, his tongue working diligently. 

He moved to John next, who encouraged him “go deep, deeper Gerald." He  pulled back, paused over John’s cock and smiled into camera. He worked methodically, his tongue darting frenulum to head he soon edged John. He lingered long for John to demand “don’t stop. That’s it, yes, yes.” Seconds later Gerald was noisily swallowing John’s cum down.

John collapsed back into his chair with a satisfied grunt, but there was no reprieve for Missy. Donald was ready for another round, already stroking himself to hardness.

“Can’t leave us wanting more,” Donald said with a grin as he tossed another 50 onto the table. Not wanting to be lightweights the other three followed suit, their laughter and taunts blending into the background as Donna’s camera stayed fixed on her husband. 

“Round two sissy. Keep it up.” Donna said. While still recording she pocketed the cash with a satisfied smirk.

Gerald, face burning with shame, stomach gurglingly full of cum, gave a weak nod and returned to his work. To everyones delight his movements grew less hurried, he leisurely engulfed Donald’s cock for the second time…

“If none of you guys want thirds we’ll be heading home” Donna said, try as she might she just could not stop smiling “Good job, Gerald, you’ve made your wife proud” she said as she sent Angelina and Molly a link.

***

Donna replaced his wig as they waited for the elevator. “Fuck Missy, that breath could make a girl pregnant.”

 

The ride down was silent until the elevator doors opened to reveal the hotel manager waiting in the lobby.

“Excuse me,” the manager said, his voice low and measured. “A word, please.”

Donna stepped forward, feigning innocence. “Yes?”

The manager’s gaze flicked between Donna and Missy. “We’ve received some information about your friends inappropriate activities. We don’t tolerate sex work on these premises. I’m going to have to ask you not to return.”

Donna’s lips twitched as she struggled to contain her laughter. “Sure, message received.”

As they walked out into the night, Donna couldn’t hold it in any longer. “Did you hear that, Missy? He thinks you’re a sex worker!” 

Missy’s face burnt with humiliation. 

Clutching the wad of cash tightly in her hand Donna said “do you realise you earned 500 in one day Missy, that is more than Gerald makes in a week!” She had pushed Missy across a line. A line she would never allow her sissy to uncross. 

“I just cannot wait until next weekend” Donna burst into laughter. “Wife, Mistress, Pimp… what next?”

***

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