The story so far: At Watts Stitching, the women in the typing pool, led by Lettie Piper and Bet Carlyle, finally had something to fascinate them at work: the eye-smacking outfits worn by the only male member in the work-force: vice-manager Gordon Fleecely, who had started coming to work in trouser suits which just had to be women's. Katherine Watts, the owner and manager, could find out anything and discovered that Fleecely was sent to work by his wife either in her clothes or those of her mother. He was no match for the women around him, and his sufferings were engineered particularly by Miss Watts, who sent him home with a letter saying it would be acceptable if his wife sent him to work in a skirt.
Chapter 2 - Gordon is dressed for working in an all-female environment.
Lettie Piper had never got to work so early. Her heart was beating sixty-to-the-dozen after the excitement of the day before, and she wanted to be in her chair, watching the door, when Gordon Fleecely arrived at the office. After what his wife had sent him in so far, what the hell would she choose for him today? She hurried out of the elevator and past Fleecely's glass fronted office. Empty. Of course he wasn't here at 7.20 am. Miss Watts had demanded that he was to wear a skirt, the wimp. It was going to be so exciting. She pushed into the main office - to find she wasn't the first to arrive by any means.
"Hey, Lettie, you're late, where've ya been?" Bet called from her desk where she was shaking her fingernails dry. "We've all been her an hour already so's we wouldn't miss a minute of today's pageant."
"I'm sure you have. But what I'm not so sure of is whether our crossdressing husband will show up today. I see we've all been raiding the backs of our closets this morning, so as not to be outdone."
Bet wore a bright pink figure-hugging dress with a collar of pink faux fur round her shoulders and dangling hoops that kept catching in it. "He'd better be here, or Ma Watts'll fire him for sure," she declared, her large hot pink lips set in the determination the manager would show.
"He's got to wear a skirt and she said he'd better wear make-up too," said Celia, who'd come in a blouse that rivalled the neat white blouse Mister Fleecely had been wearing the day before.
"I don't think he'll be in make-up," said Amanda. "The boss told him make-up was optional. If I were in his shoes, I'd opt outta that one."
"If you were in his high heels, you mean?" said Lizzie. "He was wearing low heels yesterday, and I'm thinking they belonged to his mother-in-law too, like his trouser suit did. Remember, his wife's letter said it did."
"Hands up all who think he'll come in make-up," said Lettie, taking her place at her front desk. Four hands went up. "Okay, Caitlin, what do you think he'll be wearing?"
Caitlin Ford threw her long blond hair back and took centre stage since it had been offered. "Well, his wife'll definitely go for the still-cute 30-year-old look, with soft pinks glowing with gloss, with a little glitter on his cheeks to offset the perm she will have given him last night."
The group burst out with a laugh, at the very moment that the door opened and the object of their hilarity made his badly timed appearance. Bet was facing that way and motioned to the others to shut up and look. The result was monastic silence as a cringing Gordon Fleecely found himself faced by ten women. He had evidently planned to arrive the very first in the office so that he would be sitting at his desk half hidden. Or at least not wearing this shocking coat. He kept his eyes on the floor, while having to walk towards all the women. How else was he to reach his desk, which was right beside Lettie Piper's and in front of everyone else's? It was Lettie who broke the awkward silence.
"You look nice today, Gordon." The others were happy to let her needle him, or maybe tease private info out of him. "Shall I hang up your nice coat? Mmm, is it your wife's or your mother-in-law's?"
It was his coat which was keeping the group of women silent. Gob-smacked. It hung widely from his shoulders, in strawberry pink duchess satin; a swing coat owing its style to the 1950s, and all but reaching his knees in a wide spread, with a hint of skirt underneath in a lighter pink. Gordon Fleecely shook his coat out of Lettie's hand and undid the large pink buttons himself, opening it to reveal what lay beneath. He slid it off in a sweep of sizzles before plucking the hanger from his personal coat-stand from the day before. Moments later the coat hung in all its elegance behind where he took his seat.
Like the day before, the stark bravery of the man, in spite of his humiliating appearance, was more than the women could cope with and they sat at their various desks while trying to take in the vision in their midst. Only Lettie was sufficiently in control of her scorn to lay into his fetish.
"I think your mother-in-law has a fine eye for fashion, Gordon. It must be her coat you're wearing." Her victim kept his eyes on his computer screen as it booted up. "And is it her blouse you're wearing too?"
Everyone exchanged smothered grins and scrutinised the pretty back-buttoning blouse of white silk-satin, cuffed high at his neck, with a lavish jabot of lace under his chin and billowing sleeves gathered to tubular cuffs buttoning three times at his wrists. No-one would find out Gordon Fleecely answer to this question, for the door opened and Katherine Watts swept into the main office. The click-clack of their employer's heels saw everyone focusing at once onto their computers and finally turning them on.
"My word, we must see that Mister Fleecely wears a skirt more often. What time is it? 7.40, and everyone is at their station! Good morning Lettie."
"Good morning, Miss Watts. You look very nice today."
"Thank you." The manageress was wearing a blouse in aqua satin, pleated down the front and with a hich neck cuff. Not dissimilar to Mister Fleecely's but without the frills. She was wearing her white skirt with bold buttons on each hip suggesting pockets, and her hair, as always, was neatly pulled off her face into a smartly waved perm. "Good morning," she said to him, standing with the hip of her narrow skirt against his desk. "I see you have followed my instructions. Stand up and let me take a look."
Like the day before, Gordon almost refused but didn't dare. He got to his feet, the beetroot red of his face exaggerated by the white lace that cupped his chin, and revealed his skirt in its full circle glory.
"Turn," ordered the boss. His head hung low as he did as he was told. His cerise pink skirt to below the knee revealed itself with box pleats and the dull glossy sheen of a wool and polyester mix. "Faster, please, Mister Fleecely. Give us a twirl." He had to do as he was told, and his pleats opened a little, revealing a row of buttons hidden in his front pleat. Miss Watts studied him from head to toe, noting that he had indeed had his hair done, and that he wore dark stockings with black patent court shoes. "Enough, stand still. I presume Tabitha has given you a note to give to me?" she said.
The unfortunate male stooped to the floor and came up with a hand purse in black patent to match his heels. "Very nice, Mister Fleecely," remarked his employer; "your wife has you well coordinated today. Thank you."
She opened the envelope and unfolded the paper inside. She took a quick glance down the page, then cast her eyes round the watching, female company. "Would you mind reading out your wife's message, Mister Fleecely," and she handed it back to his shaking fingers.
Some of the women present may never have seen a man tremble in public, but they saw it now in all its pleasing range of emotions. The lace round his face fluttered humiliatingly as his chin dithered on the verge of tears, his head tried to angle his face down and away in a picture of beetroot blushes, and the pink letter paper the manager handed to him just wouldn't stay still between his two hands, no matter how he tried to steady it.
"D-Dear Katherine - I appreciate speaking on first name t-t-t-terms, while we - " and he paused, swallowed, and summoned courage to continue - "while we..." and his tears spilled over, out loud, his face crumpling lower into his lacey jabot so that every inch of lace on his white blouse was shaking from his broken emotions.
"I don't mind you crying," declared Miss Watts, "as long as you are reading. I told you to read out your letter to me. Would you mind doing as I say?"
His throat tried desperately to control his voice, with the result that it gave a couple of barking sounds while he grappled with his breathing in front of the silent, watching women. An awkward swallow enabled him to get his voice under control.
"On f-f-first name terms, w-while we humiliate my husband b-b-between us." He gathered himself with a deep breath.
"Don't stop, Mister Fleecely. Read on."
"Y-You asked me to explain why I am dressing him like this and s-s-sending him to work amongst your women computer operators, ohhh-boo-hoo-hoo! It's b-because I found the l-l-limp-wristed wimp - masturbating at his computer - when he thought I was out of the house." He stopped, weeping, and stood with his eyes closed.
"Who said you could stop? Don't keep me waiting." The group saw him visibly control his sobs and carry on.
"Boo-hoo-hoo... looking at some porn site of men who wear women's clothes - and in a-a-a fully flagrant erection." He paused again but a fierce tut from Miss Watts made him focus. "In fact I saw him ejaculate his sperm into a pair of my - my, ohhhhh, into my mother's panties which he had stolen for the very purpose, and not only that -"
Gordon Fleecely stopped. His eyes rose to meet Miss Watts and begged to be released from carrying on. He shouldn't have.
"Read the damn letter!" she roared. She set her jaw and blood red lipstick to pre-empt any further interruptions.
"And n-not only that but - he was wearing one of my m-m-mother's silk blouses - with - with one of her brassieres underneath and her suspender belt and s-s-stockings. The stupid man is - oh sob-sob - in love with my mother or - or at least with her clothes."
Kath Watts ground her teeth together in a closed mouth. Her eyes flashed. "Is that all?" she demanded.
"N-No, Miss Watts. My wife writes more."
She softened her voice almost into a whisper of irritation. "Well don't you think you had better carry on?"
"Yes, yes, Miss Watts." He tried to steady his paper. "Today I have sent him to work for you, fully dressed in my mother's clothes. I hope he meets with your approval and - and I ask you to make any further requests you please, as long as they add to his - to his - to his humiliation in front of your female colleagues."
His hands sank with their letter into the front of his pleated skirt, which had the unfortunate effect of framing an embarrassing point above his legs. It was a full circle skirt, closed in its pleats but clearly filled out into a feminine tent on a bed of petticoats. Miss Watts snatched his paper from him, making him jump. "Hold the sides of your mother-in-law's skirt," she said. "Out wide. Step out here in the open, so that you are showing everyone how your wife has got you dressed today."
An audible bleat escaped his throat as he did as he was told, trying to catch the sides of his pink skirt then holding it out sideways.
"Wider! Right out to the sides!"
The emasculated male stood in front of everyone, his face a deep red above his white blouse ruffles and his stockings pressed together.
"Turn, slowly, so that we can see how you are buttoned into your mother-in-law's blouse."
He rotated, all eyes devouring his effeminate appearance, seeing the eight white blouse buttons from high on his neck to the pink waistband four or five inches deep. There was a gasp of disbelief from young Caitlin, and Celia and Amanda exchanged "Oh my Gods" as they watched him cringing in embarrassment. "His mother-in-law's skirt is so deliciously feminine," said Bet, folding her arms under her large bust. "I think he's feeling very, very feminine while he's wearing it," added Lettie. Then, as they focused on the pointed front of his skirt, the growth of his cock under its lining pushed it higher, prising open the top of his central pleat, until with an audible slither, the pleats parted and his row of pink buttons burst into view, with one pink button clearly resting on top of where his feminised cock forced its way into his punishment skirt. The opened pleat and its buttons prompted Lettie to put a question to their male co-worker.
"You look simply lovely in your mother-in-law's clothes, Mister Fleecely, but - are you also wearing her unmentionables underneath?" She avoided meeting Miss Watts' eyes, directing her question to the wretched man. His weeping rose a tone or two as Miss Watts stood close to him.
"Stand with your skirt held out to the sides," she said, then she stooped to gather the front of his skirt in a handful of petticoat lace, and lifted up all the layers and held them in front of his blouse. There were several audible gasps from the girls as they beheld the pretty lilac satin, full cut panties that hung from a very stiffened cock down to lace legs above suspenders and honey-brown stocking welts. Katherine Watts herself took one or two deep and audible breaths before she released his skirt and let it flounce into its shape around his legs.
"How very feminine," said someone, he had no way of knowing who since his eyes were so tearful. "I know someone who loves his mother-in-law's panties," said someone else. "He's going to blow any minute by the look of it," said Bet Carlyle. "Sit down at your desk, Mister Fleecely," said the manageress. "That's enough hi-jinks, all of you. I can see I'll have to do something to defuse the chance of mass hilarity today, or I'll get no work out of anyone. Lettie, see to it, please, that everyone ignores our mother-in-law clothes-mannequin here, and gets on with solid working practice." She heaved a deep sigh of exaspertion and turned on her heels to click-clack her way out. The others watched the back of her blouse and skirt recede and instantly moved into a circle to pulverise the male wimp in their midst. Almost before anyone had slung a single jibe, however, the intercom bleeped on Lettie's desk.
"Yes, Miss Watts?"
"Send Mister Fleecely in to me at once, Lettie. I've got some work for him to do."
A sheet of stunned silence fell over the whole office as the girls turned on Gordon. "What does she want him for?" asked big Amanda, "to have him sitting in front of her where she can see him?"
"To have him sitting on her knee, more like," said Celia. "D'you fancy that, Mister Fleecely? Having a woman in her late thirties playing with your whoopsy?"
"Who wouldn't play with a sissy whoopsy in those pretty satin panties?" declared Lettie, pursing her lips with female assurance. "Anyway, Mister Fleecely, no matter what Miss Watts wants, you'd better get yourself in there."
Gordon Fleecely knew she was right. He staggered to his feet like a prisoner on death row who has just heard the final summons to his fate. "Don't show her your panties again, Mister Fleecely," he heard behind him as he made for the door. "Claim your human rights," cried someone else, with laughter from every girl's lips. "And definitely don't let her treat you like a girl."
He was relieved to reach the door, except that he found himself therefore all the closer to Miss Watts's office. He tried to calm his heartbeats, facing the brass plaque bearing her name, and gathered all his courage to tap a little knock.
He opened the door to find Katherine Watts on her feet, arranging a small, high desk and chair so that they faced her own desk with barely a foot between the edges of the two tables. Her movements were business-like. "Sit here," she said, holding back the chair, "and I'll give you the work I want you to do." She studied him as he walked, crestfallen, towards her. "Oh for goodness sake, Fleecely, it's not the end of the world, but it's my time you're wasting so please get a move on." Then she stopped him at his chair with an afterthought. "You don't need your mother-in-law's skirt," and she undid it at the waist and down the buttons until she could slide it down his legs. "Are these full slips or -" She discovered his petticoats to be simply underskirts and deprived him of all of them. "Hmm, that's better. Now you can sit there, in front of me."
Gordon Fleecely had no control at all over his cock. It was so conscious of being seen and scrutinised by Katherine Watts that it simply stood on end, the victim of female power and contempt. He sat on his high chair, trying to keep his legs together, his mother-in-law's blouse floatin ground him, and waited for her to give him the work she wanted him to do. He was to compare sales figures from March-April with May-June and draw up a business plan for the next six months, while she got on with her work - with his pointed panties in front of her. He tried to concentrate, but he found it impossible to avoid bursting into sobs and even outright crying as he pursued his work. He did the best he could in the circumstances, with jism leaking repeatedly into his mother-in-law's gusset, until after lunch. It was then that she had him sitting on her lap, still without his skirt, to take some dictation. This proved very difficult indeed when he was having his cock fondled in his employer's hands in the gusset of lilac satin panties. But Miss Watts had made one or two arrangements to meet with the fetishes of her transvestite male employee.
At three o'clock in the afternoon, she led him to the closet at the opposite side of her office and opened it. "If you are to be my secretary, Mister Fleecely, you will wear a suitable skirt. Stand still while I dress you." To go with his ruffled, lacy white blouse, she produced a skirt in charcoal kid dappled with dove grey, giving it a sweet and soft slipperiness that weakened him to feeble tears of impotence. His secretary skirt had a three-inch waistband and flared to a depth of twelve inches, with a crisp acetate lining of dark grey. It buttoned at the front with five large charcoal buttons, which she slotted smoothly through their buttonholes, while over his waist she slipped a black vinyl belt four inches deep with an upright oval buckle in silver. He mewled with feeble surrender as she prettied the lace ruffles of his blouse round his cheeks, and led him like an enfeebled lamb back to her desk, where he sat on her knee and knew he would have to do exactly what his employer said. She undid the buttons of his skirt to reveal the point of his panties, and was given a notebook in which to write today's letter to his wife about his workplace dress code.
"Dear Tabitha," it began, "I am pleased with your choices of clothing for your fetishist husband. He has been suitably humiliated today at the office." Gordon Fleecely wrote down every word, silently whimpering and sobbing. "I have promoted him to the position of my personal secretary, and while it will always be wonderful to have him in your mother's elegant clothes, I sometimes like my secretaries to display their pretty legs and to be, shall we say, 'available'. I recommend blouses, dresses and skirts in light fabrics such as chiffon, so that he feels utterly defenceless - and so that I can feel him. Do you agree with me? What else is a private secretary good for than a damn good chance of sex?"
Before the envelope had even been sealed, Gordon Fleecely felt a surge of sexual desire for his employer, even though her overwhelming wish was to humiliate, punish and degrade him as completely as she could. Later, when Lettie Piper knocked politely and interrupted, she walked into a fully traditional scene of employer-secretary relations. Mister Fleecely sat on Miss Watts' desk, his legs open and his hands tied so that they spread behind him with no chance of interfering with his employer's pleasures. His sexy charcoal skirt hung neatly over his high chair to one side of the desk, while his legs, in matching charcoal stockings and strained suspenders, hung limply from the knees over the edge of the desk. His unpantied cock was hidden from view inside the steadily rising and falling rubied lips of his moaning employer. As Lettie watched from the door, Miss Watts' exclamations grew in their ardour, signifying climaxing in deep female pleasure, while her blousey secretary seemed to wriggle and spasm in some kind of fit above her, until the employer slid her mouth off his organ, allowing spurts of cum to shoot over her face and into the neck of her aqua blouse, until she closed over it again to catch and drink what she was missing. The whole orgasm lasted about a minute, treating Lettie to the very climax of the whole affair. She found herself too close to turn and retrace her steps, since Miss Watts would certainly know she was there. Her judgement was proved right as the manageress slid off her secretary's cock, now that it had given the total of its load, and turned with a dripping chin and cheeks to her floor manageress.
"Miss Piper. What is the time, pray?"
Lettie looked at the watch at her wrist. "It's twenty-past four, ma'am."
Her employer wiped her chin across the sticky knob in front of her mouth but still had drools of jism hanging from her nose and left cheek. "Very good. Mister Fleecely and I worked hard for Watts Stitching for seven hours, and left our pleasure-seeking until after 4pm. That is how I have got where I am today." There was no sound from her bloused companion, since his face was wrapped in a multi-coloured silk headscarf so that he could neither see nor speak. "Please close the door after you, Miss Piper, and put up a 'Do Not Disturb' notice. I have another half-an-hour at least to enjoy myself with my personal secretary." Her mouth closed over the wet helmet, and as Lettie Piper turned to leave, it sank warmly down the length of the stiffened wet cock to its very root.