The Boss Lady

By Coquette
Another day at the office, and the girls were arriving for work. But this office was a little different because all the ‘girls’ were sissies.

Miss Strop arrived early and counted the sissies as they went in. She wore a red satin blouse, stretched tight over her magnificent bosom and nipped in at the waist by the belt of a black PVC skirt. The skirt was slit up to the top of her rounded thigh, revealing a thick black suspender clasped to her stocking top. As they passed, the sissies looked in awe at the line of her perfect panties showing through the skirt, which hugged her ample and powerful buttocks. Miss Strop wielded a cane and would use it if any sissy did not look and behave in a sufficiently lady-like manner. A tall, slim panty-boy walked nervously past, struggling to balance in his new high-heeled shoes.

"Deportment, Sandra!" cried Miss Strop, fetching her a sharp smack with the cane on her little panty-clad bottom. Gush had been set up by Miss Strop and specialised in high-class dildos for fine ladies. They had the widest range available and the business was doing extremely well. Lately, Gush had branched out into equipment for the emasculation of wayward husbands.

Their best selling line was a tiny toy zapper which looped around the darlings’ scrotums and was operated by the lady’s mobile phone. It was easy to fit while hubby was asleep. It was a little token of their love, the lady would say. Whenever the lady wished, she could dial a secret number and listen to what hubby was up to. Then, when she liked, she could press a key and hubby’s frisky little balls were given the sweetest electric shock. Nothing too dangerous, just a few hundred volts, but enough to put them out of action for a while and remind him who was boss. You could even hear hubby’s little cries of surprise, the poor darling. It was a wonderful idea and women loved it, although, as the instructions warned, wives had to exercise a little self-control and not use it too often, or hubby could easily be turned into a sissy.

I am sorry to say, this is why some ladies bought it in such numbers. The Gush ‘Womanizer’ was selling like hot cakes and the number of nasty males was rapidly dwindling.

Miss Strop had enjoyed testing the prototype on her ex-husband. She laughed aloud, remembering how she had pressed the keys just as unfaithful David was thrusting his love-bloated organ into Angela Percival for the very last time. She made sure it was the last time for him, too. The clandestine lovers thought they were out of reach in Angela’s secret retreat in the south of France, but Miss Strop had heard their every little gasp, every little smack of David’s besotted balls against Angela’s elegant labia. So, just as the happy pair climaxed -it was such a shame, Angela did so love it doggy fashion- Miss Strop’s finger gently squeezed the appropriate key.

His wife left him and, not long afterwards, poor David began to take a very healthy interest in feminine undergarments. Something deep inside him made him desire the touch, the scent of ladies under-things. Perhaps it was his frustration at no longer having a woman to sleep with, although Maxine had never permitted him to touch her more than once a month. Perhaps it was something more mysterious. But, whatever the reason, his whole being now became focused on the pursuit of ladies’ panties. As his cravings increased, the women of the neighbourhood started to lose bras and panties from their washing lines. They little knew that their personal items were being ravaged and sullied with David’s sissy spunk. The thrill of wearing women’s stolen panties was enough at first, but David’s rampant dolly was insatiable and soon sought something more exotic than the local ladies’ cotton undies. He took to raiding ladieswear shops to satisfy his growing urges. But he was naïve in such things and not a natural thief. In no time at all, the foolish boy was found stealing expensive ladies’ underwear from the local department store and he lost his job in the city. He was finding it very difficult to get a new one

He knew had to set his sights a good deal lower if he was to find a job at all. Scanning the local newspaper a week later, he found an advert. ‘Panty-boys wanted. Strict regime. Nugatory pay. Submissive sissies, phone Miss Strop right away at Gush.’ It was his ex-wife’s firm. There was nothing for it. With a deep sigh, he resigned himself to the inevitable and phoned her. "Er… Maxine?" he began, nervously, "I understand you have a..."

"Don’t ever call me Maxine again. Get your girlie panties on and get over here at once, you pathetic sissy," bawled his ex-wife, "And you call me ‘Miss Strop’ from now on. Do you understand?"

"Y-yes, M - Miss Strop," muttered David, downcast. He prepared to go out. He had lots of ladies’ panties and suspenders, but he had never worn a dress. He went to his ex-wife’s wardrobe. She had left some clothes, and he found a black silk dress and black high heeled sling-back shoes. He had let his hair grow and thought it could now pass as a woman’s, if he styled it right. He put on some of his wife’s make-up and made a reasonable job of it. Picking up a handbag, he trotted off to town.

Nervously, David knocked on the door of Gush and told the sissy receptionist he had come to see Miss Strop.

"Wait there," she said, with a smile, indicating a chair. David looked around him. Pictures of dildos of all shapes, sizes and colours adorned the walls. An array of the naughty things themselves stood proudly along the desk. They looked so perfectly designed by ladies, for ladies, and he could see that no lady would be able to resist them.

There was a familiar footfall outside the door and Maxine Strop burst in.
"Well, well!" she laughed, looking him up and down, "Your wearing my little black dress, you panty-wanker. So, not content with shoplifting ladies’ panties, you’re stealing my clothes, too."

David blushed and looked at his feet.

"Stand up, girl!" bellowed Miss Strop. David was surprised at the unexpected power in his ex-wife’s voice. He was scared and stood up right away. Miss Strop looked him in the eye, took hold of the thin black dress in her fist and tore it off him. He stood before his formidable ex-wife dressed in a sweet little bra and panties, quaking with fear.

"Where are your stockings?" frowned Miss Strop.

"I - I - don’t know," mumbled David, confused. Miss Strop took a pair of seamed black hold-up stockings from a drawer and threw them in his face.
"Get those on!" she spat. As David hurriedly complied, struggling with the unfamiliar feminine garments, Miss Strop threw a little dress at his feet. It was a tiny pink satin dress with puff sleeves. Its little skirt was lifted by lots of frilly white petticoats, edged with lace. David stepped into it and pulled it up to his waist. The tight satin bodice hugged his tummy and squeezed out his tiny breasts so they almost filled the small bra he was wearing.

His ex-wife smirked at the bulge in David’s panties, clearly displayed beneath the stiff skirts. The sissy-boy likes his new outfit, she chuckled.

"From now on you will be known as Davina," she said with finality, "Follow me." She open the door to the office.

"We have a new girl today," said Miss Strop loudly to the other sissies, as she strode between the desks. David followed in his high-heels, stumbling as he went. Miss Strop glanced back at her ex-husband. He was really quite pretty, she thought, with a giggle.

Miss Strop had always preferred women for her sexual gratification. Her current lover was Miss Horton, a temp who sometimes worked in her office. Miss Strop adored her shapely body and decided she had the perfect vulva for testing dildos. The previous evening, she had been trying out prototypes of her latest creation, the Gush ‘Fat Lady’ on her unsuspecting partner. It was the largest dildo the firm had yet produced and Miss Strop was very enthusiastic about this exciting new product for the larger woman. It proved to be a winner. Poor Miss Horton was made to come sixteen times before Miss Strop decided which was the best and was satisfied with the quality.

Miss Strop liked to carry out random checks on the contents of the sissies’ handbags. It was for security, she said. Last week, she had spotted one of the newer sissies stealing from Miss Horton’s desk. The appalling audacity of the panty-boy! He would pay dearly for it. All the sissies knew that Miss Horton kept a supply of spare panties in her top drawer in case Miss Strop should make any impulsive demands on her in the back office. But Sandra, who had developed a girlie crush on Miss Horton, had found the nearness of her panties irresistible.

"You, girl!" snapped Miss Strop, fiercely, "Come here!" A frightened slip of a sissy stood bolt upright at her desk in fright, shaking all over. She was quite tall and her short blue satin skirt stood out, raised by lots of frilly petticoats and revealing a sheer white thong, finished with a little blue bow at the waist.
"M-m-me, Madam?" she queried, timidly, knees knocking in their white stockings. Her stomach clenched with fear. She was an excitable sissy and still very awkward in her new girlie role.

"Yes, you, Sandra! Get your fanny over here, you little slag!" Sandra quickly trotted in terror over to Miss Strop’s desk at the front of the office. She was not yet used to her high heels and wobbled precariously as she stood in front of her boss, eyes downcast, her hands clasped behind her back, as she had been taught.
"Open your handbag," said Miss Strop. Sandra gulped. She didn’t want Miss Strop to see what was inside. With nervous fingers she placed her little pink handbag on the desk and opened it a crack. Inside, Miss Strop could see a riot of pure white silk. She snatched the bag from the terrified sissy and pulled out a pair of expensive ladies’ panties. She displayed the classy white silk undergarment to the quaking sissy.

"Whose are these?" she barked. But she knew the answer.

"I d-d-don’t know, Mith," squeaked Sandra, ogling the wondrous lacy things.

"Yes, you do, girl. They’re Miss Horton’s. Her best panties."
"Y-yeth, Mith," muttered Sandra.

"And what on earth is this?" asked Miss Strop, pointing to a large white stain which disfigured the perfection of the beautiful silk and stiffened the pretty crotch.

"I d-d-don’t know, Mith," trembled Sandra.

"Oh, yes you do. It’s girlie spunk. Your girlie spunk."

"Yeth, Mith," admitted Sandra, blushing with shame.

"You do not masturbate in Miss Horton’s panties," snapped Miss Strop. Tears welled in Sandra’s eyes. But something was welling up inside her own panties, too. The horror of being singled out for humiliation by Miss Strop always had this effect on her. She bit her lip.

"If I find you stealing Miss Horton’s panties again, I shall personally nip off what’s left of your tiny plums."

"Y-yeth, Mith," said Sandra, but her dolly’s excitement was now lifting her petticoats.

"Oh, my goodness!" cried Miss Strop. A prominent bulge in Sandra’s sheer nylon thong poked out over her desk.

"I - I - c - can’t help it," cried Sandra, as her long, slender dolly pushed itself over the waist of the inadequate little panties and wagged rudely at the Boss Lady.
You disgraceful hussy!" cried Miss Strop, "Put that away at once!" Sandra flinched in shock. The nervous sissy lost all self-control. Suddenly her long dolly bobbed and puked violently. Strings of white cream flew across the desk.

"Ugh! Oh, my God!" spluttered Miss Strop, as the bust of her designer blouse was splashed with a heavy spurt of sissy juice.

"Oh, gosh! I’m sorry, Mith, I’m sorry. I couldn’t stop it," cried Sandra, weeping in despair.

"Sharon and Fiona," called Miss Strop, severely.

The two sissies held Sandra in front of the whole office and pulled down her little thong. Her dolly poked out stiffly at the admiring group of sissies crowding around.
"Davina!" called Miss Strop. David came forward, apprehensively. The others looked on jealously, knowing what was about to happen. "Kneel down and kiss Sandra’s dolly," said Miss Strop.

"No, please, Miss Strop," pleaded David, "I don’t like sissy-boys." But somehow found he couldn’t resist as Miss Strop lowered him to his knees.

"You’re a sissy now, Davina, and sissies love sissy cream." She pushed David towards Sandra’s excited dolly. Almost without realising it, he opened his mouth and took the bulb of sissy-flesh on his tongue. Miss Strop shoved his head forward and the warm, slender thing slipped between his lips.

"Oh!" squealed Sandra in pleasure, as her dolly rode along David’s rough, wet tongue. David felt Sandra’s sissy flesh expand in his mouth and the skin of her little scrotum rumple against his lower lip. It wasn’t as nasty as he had imagined. It wasn’t nasty at all. Sandra was sweetly scented and her skin was so very soft.

"Wicked girl," growled Miss Strop, and flicked her cane against Sandra’s tight buttocks. She squeaked and her nervous dolly ejaculated. David choked as the semen flew to the back of his throat. He pulled away, but Sandra had lots more to do and pumped several slicks of hot juice across his face before she stopped.

"There!" laughed Miss Strop, as David gulped down the sissy-cream, "You do like sissy-boys! I can see you two girls are going to be very good friends!"

She put Davina at the back of the office with Sandra to deal with the incoming orders. They sat together, furtively admiring each other’s panties and blushing shyly if the other one noticed they were looking. Later that morning, the mail arrived. David recognised the handwriting on one of the envelopes and opened it with trepidation. It was from Angela Percival.

Darling Gush,

Please send me another Variety Pack of ladies’ dildos post haste. I have had great
fun with the previous set, but have now worn them out with constant use. A friend has suggested changing the battery, or some such, but that’s far too technical for me. I enclose a check for £200 which, considering the pleasure they give, is the bargain of a lifetime.

Yours faithfully,

Angela Percival.


A tear ran down Davina’s cheek. He had not seen Angela since that day on the Côte d’Azur when the little ‘eternity ring’ Maxine had fitted round his balls in token of their love had ended their fun. He still had the horrid thing on. He showed it to Sandra, who told him what it was and that it was a good thing, really, because it had made him a sissy. Sandra had no sooner wiped away his tears with the frilly silk handkerchief she kept in her panties than there was the sound of high heels clattering impatiently along the corridor and a well-dressed lady ran into the office.

"Oh, my God, what a climb. Is this Gush?" asked Angela Percival, breathless from her rush up the stairs. Sandra curtseyed.

"Yeth, madam," she said. Angela looked with disdain at the slender figure of Sandra.

"Where’s the manageress?" she said. Miss Strop strode towards her between the rows of desks. Angela’s blue eyes stared at the familiar shape of the woman approaching her.

"Angela!" said Miss Strop, smiling sweetly, "How nice to see you. Can I help?"
"Maxine! Oh, my goodness," breathed Angela, suppressing a rush of feelings, "I - I’ve come for a set of…"

"Dildos?" queried Miss Strop, "Are you using our lovely products? How charming."

"Actually, I think I’ll go…" began Angela. This was too embarrassing.

"I won’t hear of it, darling," said Miss Strop, taking her by the arm, "Come with me and I’ll soon fix you up." She escorted the uncooperative Angela through the office and into her private office.

"Please take a seat. I’ll get one of the sissies to bring you one. Davina!"
Davina flounced into the room in her little pink dress.

"Yeth, Miss Strop?" she said.

"Fetch a queen size Variety Pack for this lady. Immediately, girl!" said Miss Strop. Davina suddenly realised who the lady customer was. She ran out of the room in horror.

"Do I know that strange girl?" said Angela.

"Yes, she is new. Soon knock her into shape." A few minutes later, Davina came back and stood at the door, eyes downcast, holding a large box in front of her.

"Don’t stand there looking stupid, girl, hand it to me." Miss Strop took the box and opened it.

"I’m so pleased you use our dildos. You’ll love this new addition to the set!" she took out the Fat Lady, "I think it’s going to be very popular." Angela looked at the convoluted balloon of pink latex with widening eyes. The moulded tip bore the head of a plump woman with her fat tongue pushed rudely out.

"You might find it rather advanced at first," said Miss Strop, "Would you like me to show you how to use it?" Angela stared open-mouthed at the dildo without answering.

"It’s really quite simple. Davina, touch your toes, girl," commanded Miss Strop.

"B-but, please, Madam…" complained David. But Miss Strop had already whipped his little panties down to the knees and was tying his wrists and ankles together with a wide ribbon.

"Goodness!" exclaimed Angela.

"Is anything the matter, madam?" asked Miss Strop.

"It’s… David!" gasped Angela, scanning the pretty shaven scrotum with growing recognition. A little pink loop of plastic pinched the top of the bag and held fast a Womanizer.

"Yes, Angela, but she’s called Davina now."

"Oh, Lord! To think I…" Miss Strop ignored her and coolly continued with the demonstration. "It’s quite easy to use. You simply touch this to your lips, like this, and press the switch, here." Angela watched in awe as the formidable device began to tremble and thrust itself roughly into Davina’s unexplored bottom.

"Golly!" she cried, watching David’s little balls vibrate between his hairless thighs as the Fat Lady plunged itself deeper and deeper into the whining sissy. The familiar shape of David’s erection popped out of the panties.

"Goodness!" said Angela, staring at the bumps and veins she knew so well.

"You will notice that her little dolly is getting very excited, " said Miss Strop, "And in about ten seconds, the lovesick little thing will succumb to the Fat Lady’s irresistible charms…" Moments later, there was a scream from Davina and what seemed like a good half pint of sissy cream gushed on to the floor in one long fat stream.

"My God!" cried Angela.

"It’s really designed for the larger lady, but of course will suit any woman who likes to be stretched."

"You bitch!" cried Angela, and struck out at Miss Strop, who caught hold of her arm. The two ladies looked at each other in anger for a long moment. Then Miss Strop’s grip relaxed. Slowly, Angela’s pupils were dilating. She stood away and began to unbutton her blouse.

David was kneeling on the floor and caught the quickly-discarded garment in the face. Impulsively, he pressed the beautiful silk to his nose. Angela’s familiar scent entranced him and the fine silk tickled his cheek.

"Do you like the lady’s lovely blouse, Davina?" asked Miss Strop. David grunted. Angela’s slip dropped gently in front of him and he fell forward and nuzzled it. Beautiful, beautiful ladies clothes, he thought. His dolly stiffened anew. "One day, if you’re very good, you might grow to be a fine lady like Angela," teased Miss Strop, standing with her back to the door and watching Angela intently as she stripped. She could see why David had liked her.

"Look at the lovely bra and panties set Angela’s wearing, Davina," said Miss Strop. Angela smiled and slipped off her pretty little white silk panties, decorated with tiny red hearts and edged with fine lace. She threw them to David, who grasped them greedily. He inhaled the piquant sweetness that he knew only came from panties a blonde lady has worn. But it was only the feel of the panties he desired now.

"P-panties, panties…" he smooched, caressing and sucking the soft crotch, while his little dolly strained in Angela’s silk blouse.

"Yes, David. Panties," said Angela, laughing.

"You can play with those, while we ladies get on with the grown-up stuff," said Miss Strop. Poor David kissed the panties again and again and ran the heavenly silk through his fingers. He wanted so much to come in the blouse, but his poor dolly gaped, perplexed.

Angela climbed on to Miss Strop’s wide desk on her hands and knees, facing away from Miss Strop, who still held The Fat Lady in her hand. Miss Strop looked at the bobbed blonde hair strewn on the desk top and the pretty breasts hanging lightly in the neat bra cups, patterned with hearts. She really is quite a delightful girl, she thought, stepping up to the desk. And I’ve always had a penchant for blondes. She unzipped her PVC skirt and dropped it to her feet, then quickly threw off her blouse.

"As I was saying," Miss Strop continued, "It’s very versatile and comes with this leather harness, which turns it into a rather superior strap-on. Like this." Angela turned her head and looked in awe at the buxom female figure in a sturdy black bra and maxi-knickers who stood behind her, rubbing the huge dildo with Gush lubricant.

"Fuck me, Maxine," she cried, almost screaming in desperation, "Please!"

"Tut-tut," scolded Miss Strop, wagging her finger, "You need to learn patience, young lady. Doesn’t she, Davina?"

Holding her panties to his nose, David glanced up at the rose-pink petals of flesh which adorned Angela’s pretty bottom. He had no time to admire the shapely buttocks and perfect thighs, spread wide. With a sudden rough swipe of her fat palm, Miss Strop spanked the immaculate genitalia and he heard Angela’s familiar squeal of surprise.

"Isn’t she sweet, Davina?" teased Miss Strop, "I do believe this is her first time." David watched his ex-wife run the tip of the Fat Lady up the pretty folds and gently coax its head between Angela’s coral lips. She planted her arms either side of the lovely back, leaned forward and smelled Angela’s beautifully-styled blonde hair. "Bitch," she whispered, close to her ear, placing a finger to the switch. She clenched her powerful buttocks and squeezed the quivering, pulsing dildo as deep as she could into the lissome Angela.

"Oh, Maxine!" cried Angela, as her exquisite breasts trembled on the desk and her pampered body surrendered its precious juices to the Fat Lady, "I love you!"
While Angela’s love spilled on to her desk-top in profusion, Miss Strop looked down at the sissy-boy sprawling on the carpet, his bloated dolly trying to make love to Angela’s panties and blouse. She picked up her mobile and pressed a few keys. Davina screamed.

"It’s not over ‘til the Fat Lady sings!" she laughed.


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Thank you, Prissy.
Posted here with respect and admiration.