A Sissy Soirée

 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.

***

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