Part 2 (of 4): In Sissy Lingerie
The story so far: Veronica Boothroyd has delivered her stepson Jason into the hands of Alicia Presswell, the manageress of the Pretty Boy Boutique, where he will work as a sissyboy assistant during his summer recess from college. The girl assistants, Kate and Serena, take photos of him dressed in his pretty uniform and showing an unwanted erection, so that he must do as he is told to prevent the photos being distributed through the facebook accounts of his friends. As he performs his sissy duties dressed in frills, his penis displays evidence of latent femininity in his nature.
"He can come out of his uniform for the rest of the morning," announced Miss Presswell. "I want him circulating through the different departments of the boutique and I want him available."
Serena bit her glossy lower lip as she took Jason's hand and gave him a sympathetic look. He felt a quiver in his legs as they followed the pink blouse frills and silver grey pencil skirt of the manageress into the staff suite. After that humiliating start to his day at Pretty Boy, what on earth did she mean by having him 'available'?
"Oh dear, hun," murmured the young shop assistant, undoing the back of his basque, "I'm afraid this is where your sissyboy perversions are going to begin... but you will probably enjoy being sissyish and... well... a bit of a girl."
"Like hell!" retorted Jason, setting his jaw and pushing her hands away from the waist of his panties. "What do you take me for? Some kind of a mummy's boy? Well I've got news for you, girl: I - am - not - a - sissy!"
He realised out of the corner of his eye that he had raised his voice too far: Miss Presswell's crimson mouth had wrinkled between her beauty spots, and her diamante eardrops were trembling with menace beneath the base of her piled blond hair.
"How dare you speak like that to one of my girls," she said, her voice reduced to a hiss. For a moment he thought she was going to take a step and smack him across the face, but she turned to her desk, pressed a few keys on her computer and opened a folder of images on the screen.
His mouth fell open. They were all pictures of him in his sissyboy suit, a line of them showing him in his short pink skirt and dozens more catching him in unforgivable intimacy with the boy in the petticoat slip.
"You are refusing to cooperate," she declared, "so you leave me no option."
She selected one photo and filled the screen with it: a moment when he was having a baby's pacifier taken out of his mouth and his penis was in complete erection on the outside of his pink satin shorts. A sinking feeling dragged at his stomach.
"This one will do to begin with," continued Miss Presswell as Jason tensed his arms in the grip of Serena. "Now, we just need... there we are."
"Wha...! How...? That's my facebook page!" he spluttered. The next thing, his list of friends was staring back at him from the screen, in full view of this vicious woman. "How the hell did you get into that?" he cried, his voice almost a squeal.
Miss Presswell continued in complete calm, a smile twisting her carmined lips as she scrolled through screen after screen of the people who made up Jason's world. "You've got your dear mother to thank for giving me this effective means of turning you into a sissy, my boy. I can't have any half-hearted efforts at being effeminate and wimpish. But now it's just a question of exposing your prissy sexuality to everyone who knows you."
Jason may have been wearing no more than a pair of white ruffled panties but his skin was breathing sweat. "You can't. Fuckin' shit! Oh... sorry. I mean, hey, you can't show that picture to anyone, d'you hear!" "Andrea Whitehead, Geraldine Amos, Fran Pickford," said Miss Presswell to herself as she made her selections. "Georgie Jenkinson, Hayley Watts and... let me see, a couple of boys... Jack Kapranski and Brad White."
Jason stopped wrestling against Serena and stood rigid with fright. "I'll do anything you like, Miss Presswell, ma'am. Anything! Everything! I'll do everything you want me to do, without any grumbles, but please... PLEASE don't send my picture out to those guys." He sank onto the knees of his white stockings. "I'm begging you, ma'am. I want to be the Pretty Boy sissyboy. I'll kiss another sissy... in satin panties... until he cums..."
His head was bowed in supplication, or rather, in a fit of despair, his voice disappearing into promises of complete obedience. Miss Presswell looked down at him without moving from her keyboard.
"Why should I be patient with a worthless nancyboy who promises to do all kinds of things, then changes his mind when he is given his instructions? You are not worth my time, boy. You're a little maggot, like so many sissy wimps."
The prospect of Geraldine Amos and Georgie Jenkinson seeing him wearing a white ruffled blouse and pink satin shorts was making Jason's stomach retch with fear. He crawled the distance between Miss Presswell and himself and fell on her court shoe in black patent, holding his face against her stockinged foot and the shiny leather.
"Oh Miss Presswell, I promise. I promise with all my life and... and with my SOUL, ma'am! I won't mess you around. I'm going to do just what you say, and the girls... whatever they tell me to do. Just please don't send the photo. Please log out of my facebook page, I'm BEGGING you!"
The manageress exchanged a look of success with Serena standing opposite her.
"Miss Presswell," piped up the 20-year-old, "Jason has tried very hard to be a good sissy boy so far. I think I can promise you that he won't try to be a normal boy again while he's working with us at Pretty Boy."
Alicia Presswell took a deep breath. "Well I suppose my next step in sending out your photos will depend entirely on you, Jason," she said; "on your perfect behaviour."
"Oh thank you, ma'am, thank you," and his kisses slid from her shoe onto her stocking, as if it was to her foot that he owed a debt of deepest gratitude.
She rolled her eyes in patient forbearance. "Get up!" she said. "You need to be got ready. And let me remind you that any signs of boyish behaviour, or complaint... the first hint of rebellion, and that's it, you're fired. With a boom of photographic exposure. Do you understand?"
Jason had never been so clear in his life. He would give her no excuse whatsoever.
"And to make sure you're behaving yourself, my little fellow," she went on, "I shall take you with me to the Pretty Boy display room until lunchtime."
A fit of sobs overcame him. How close he had come to utter destruction. He clenched his hands into fists and resolved to do what he had to do, and be a model of stillness and grace. His feet lifted obediently for his panties to be slipped off, followed by his stockings, and Miss Presswell reached into her closet to take out the costume he was to wear as her sissyboy-in-residence.
Jason looked at himself in the dressing room mirror and wiped away his tears before they left his watery eyes. He was making a resolution not to let himself down with any of the sissy softness he had shown already this morning. But it was difficult. He was wearing a little white bra with a cute ribbon bow between its cups and a pair of shiny panties to match, with another little bow in the middle of his waist. They were like the panties his stepmother wore, covering his bottom and cupping his genitals in white satin. Instead of stockings he had white ankle socks, with a puff of lace decorated with white flower shapes. He even had little bows of white ribbon on the lace frilling of each sock, and over them, a pair of pale blue Mary Jane shoes with two thin straps across each foot.
Serena held a petticoat over his head and it dropped onto his bra cups in a silky bodice, spreading outwards in paper nylon stiffness from his lower ribs. He tightened his fists to prevent a shiver of embarrassment: the skirt of his petticoat flared from well above his waist but was only 12 or 14 inches deep. What kind of childish little skirt was he going to be put into?
His blouse came next, in cream satin, with puffball sleeves at each shoulder which Serena fastened at the outside of the cuff halfway down his upper arm. Then she arranged his blouse, fastening the pearly buttons down to where it lay on his petticoat skirt. There was a frill of corrugated satin two inches wide down either side of his buttons, as well as round the edge of the rounded collar so that the frill just touched the puff of each sleeve. A similar frill decorated the cuffs on his arms, so that his blouse seemed to be all ruffles. "A girls' blouse," he thought as Serena fussed at the back; "a girl of five or six would wear this to a party." And the worst thing about it was how it stuck out widely and showed the deep, lacey hem of his petticoat, and didn't cover his panties at all.
His misery was interrupted by Serena, who turned him towards her and wrapped a skirt of ice-blue taffeta round him. Oh no-o-ooo! The material had 'Kiss Me' scattered here and there in glittering silver! It buttoned together down the back, but an ache of shame seized him as he realised how she was fitting it to his blouse: there was a line of cream buttons across the front of his blouse, beneath the level of his little breast cups, and they buttoned though buttonholes on the waistband of his skirt. She fastened another button under each arm, and four more across the back. He was wearing a childish, button-on skirt with his blouse and he broke into a flurry of humiliated sobs.
"Hurry up, Serena," said Miss Presswell, using a tissue to shape her crimsoned lips. "His place is in the boutique, not hidden out of sight. Give him two Paradise Bows in his hair, and once his gloves are on, put his hands into thigh ribbons."
"It's nothing to cry about when you look so pretty, sweetheart," murmured Serena as she clipped a butterfly bow of pale blue silk into each side of his soft blonde hair. "The sissies who come into the boutique will want to hold onto you and feel your little peeny in their fingers."
This didn't help his nerves as she fastened matching ribbons onto his bare thighs a few inches below the lace edging of his panties. She took his hand and threaded a glove of powder blue satin onto his fingers. It buttoned round his wrist with glass buttons, which carried on up his arm: ohhhh! how long it was! The ribbon fastening wrapped over above his elbow, finishing with a press fastening under his blouse sleeve in the shape of a bow with a large blue button in the middle. His other hand was gloved too, and buttoned up to his elbow in the same way.
Miss Presswell stood a few inches higher than Jason in her very high heels. She held his hand beside his thigh as Serena wrapped the leg ribbon round his wrist and did it into a bow. He was bowed at the other wrist too, so that his hands were now secured to his thighs, making his skirt billow out all the wider at front and back.
"Put this Fairy-Tail harness on him so that I can keep him with me," she said, passing an armful of rose pink frills to her assistant.
Jason cringed with shame as he watched a set of reins in doubled satin being buttoned round his waist, beneath his arms. The frills went over his shoulders from front to back and were buttoned into place. His blouse sleeves almost disappeared beneath the copious ruffles that spread over his shoulders, and his penis stiffened firmly in the gusset of his panties.
"Remember, boy," rasped the manageress as she held him from behind by his satin reins, "perfect sissyboy behaviour!. If I am not delighted with your performance in the boutique, you will become a dainty sissy friend to all the names in your facebook. Forward sissyboy."
Serena opened the door, and Jason found himself tip-tapping out into the store. Oh horrors; from being as peaceful as a library half an hour before, the boutique had sprung to life. Jason saw Kate behind a counter, spreading a little party dress for an elderly lady to look at. Her hand gave a little wave but her smile changed into a giggle.
Miss Presswell, held Jason by short ribbons so that the ruffles of her bust pressed into the ruffle at his shoulder. "You will help ladies to select pretty lingerie for their sissies and of course you will show suitable feminine sweetness towards any sissies we meet," she said. "A sissyboy always shows the same affection for all sissies, regardless of their age, since they are all sweet little girls by nature."
Jason was trying to control his panicking heartbeats. "W-Will I have to kiss another boy?" he asked anxiously.
Jason nearly fainted. His eyes fluttered and the next thing, a shock filled his nostrils knocking his head back. He blinked, and realised that Miss Presswell had applied smelling salts to his nose. He sneezed and sneezed again.
"Wake up, child," she said, her forehead wrinkling above him. "We haven't got time for fairy antics like feeling faint and collapsing on the job. You're going to feel a lot more feeble and delicate than that as the day wears on." She took a silk hankie from the sleeve of her blouse and wiped Jason round the mouth, filling his nose with her perfume. His head was feeling mightily cleared and he repeated her sissy kissing instructions, as well as learning a few more.
When he was repeating things correctly, she made him walk ahead of her between brightly coloured dresses from floor to ceiling, oozing with chiffon and ribbon bows. He found himself reading the direction boards: Sunday Best Babywear, Petticoats, Party Frocks, Playpens, Rubberwear, Restraints. A large board above an archway read Lingerie and Corsets, and beneath it: This Way to Schoolwear and Discipline. A moment later they were in the lingerie department, where two women were sitting watching a middle aged woman in a crisp blouse and long skirt attend to what must have been a sissy. Only the sissy was a grown man, at least ten years older than Jason. He was wearing no more than a white full corselet and under it a pair of pink panties. The tops of his tan stockings were gathered down onto his knees.
"Good morning, Janet; good morning ladies," said Miss Presswell, moving Jason up to within arm's reach of the sissy. "Who have we here?"
"This is Sissy Satinette," said the boutique assistant, finishing the last few hooks at the back of his corset. "She has come to Pretty Boy with her Mistress and Mummy-in-Law to be corseted for her birthday party. This is Brenda, and her daughter Cerys." She finished by pulling a strong zipper up the back of the corset, lifting Sissy Satinette onto his toes with a little whimper.
Jason felt his cheeks blush and his penis tug firmly on his panty silk as it grew in front of the watching women. Or was it because of their pretty sissy husband and son-in-law? The wretched male was wearing wide legged French panties prettied round both legs with three inches of pink lace, and they were tented in front of him from the bottom edge of his corselet, so that the double dome of his penis helmet was beautifully shaped in gleaming satin. His corset was in lacy panels that alternated pink and white, with six suspender garters of ruched white satin that hung loosely halfway down his panties. His bra cups were shallow, perhaps an A cup, but judging from the smooth flesh of his chest they must have been filled with his own breasts and nipples.
"Is this one of the Pretty Boy sissies?" asked Brenda. She was clearly over sixty, with perfectly dark hair in a perm and a wide collared coat in avocado wool.
"This is our only sissy-in-residence over the summer," replied the manageress.
"How sweet he's wearing a lovely girls' blouse," said her daughter, grinning as she got up to feel the ruffles down the front. "Look, mother: his skirt buttons onto his blouse. I love that."
"We'll have to get that outfit for the fairy," replied her mother. "I must say, his blouse and very short skirt add a charmingly childish touch to his appearance. And I like the way his hands are fastened helplessly to his legs."
"He will greet Sissy Satinette with a kiss, ladies," said Miss Presswell, and she undid the ribbons at Jason's thighs to release his buttoned gloves.
Both the women gasped with delight and watched open mouthed as Miss Presswell stood Jason in front of the corseted sissy.
"You know what to say, boy," she said, her face twisted as if she had a slice of lemon in her mouth, and she took the older sissy's hand to wrap Jason's fingers round it, then the other. Their faces were six inches apart, both blushing a deep red.
"Well, this is a lovely treat for you, Sissykins," said Cerys to her husband with a giggle as Janet stood behind him and held his waist in case he tried to pull back.
Jason's pulse was throbbing as he forced himself to look his partner in the eye. "I... feel so precious in front of you, darling," he said, pausing and pressing his lips together to control their tremble, "I simply have to plant a loving kiss on your sweet lips."
The sissy husband dropped his eyes as Jason's lips approached, and at the moment of touching, a quiver ran through the sissies, bringing a bleat of emotion to the lips of both of them at the same time.
Jason's penis was achingly hard now, suffering the embarrassment of another rush of effeminate feelings. Why was this happening to him? In front of Miss Presswell and these grinning women? He wished he had never woken up this morning and been brought to this dreadful place... but... he had to admit...the kiss gave him a feeling of sheer loveliness. It was pleasurable to him. Kissing this sweet sissified male in his corselet and... and whispering little feminine affections to him. He wondered what the man's real name was. Michael, maybe, or David?
"Kiss me," he said softly, barely lifting his lips from Sissy Satinette's, and his penis jerked with a frisson of pleasure as he felt a soft push of lips against his own and a dainty vibration as a whimper rose from the sissy's throat, and for a few delicious moments their lips pressed softly together.
"Oh isn't that sweet," he heard as their faces parted. "Don't they look lovely together, exchanging delicate kisses?"
Jason was ready to faint again and barely knew what was happening to him as Miss Presswell tightened his pink reins and held her smelling salts to his nostril again. He sneezed and stumbled about as she held onto him, then pointed him towards the opposite side of the lingerie department.
The shock of feeling so sexually aroused while he was kissing another sissy had Jason close to panic. His body was telling him something new... something he was afraid of. What if he was really a sissy himself? No, that couldn't be. He was eighteen. He would have known all about it by now, after chasing girls all his life. It made him feel pretty feeble, though, and ready to crumple into a little ball on the floor and hide.
He soon woke up when he saw where Miss Presswell was bringing him: to the other lingerie counter, where Kate was serving a woman and her sissy boy. He knew at once Kate had been watching him because she spoke to him as they drew near.
"That was lovely, Jason darling," she said, flicking out her blond hair all round the collar of her uniform blouse. "I could see how happy you were, kissing that darling sissy... and he loved it too." She grinned to the manageress. "I think he's going to make a perfect sissy assistant for Pretty Boy, Miss Presswell."
"Maybe so," replied the manageress; "it's practice he needs. So who have we here? Introduce us to each other."
"Mrs Marchison is having her son fitted for his school uniform. This is Miss Presswell, the manageress, ma'am."
The client was tall and in her forties, in a long purple coat which she wore open, revealing a floral summer dress. Her hat, shoes and bag were apple green. "This is Andrew," she said. "The idiot got himself thrown out of college for being too girlish... the male students couldn't concentrate on their studies. So there's nothing for it, I'm sending him back to school. Girls' school."
Her son hid his face in his hands and rocked on the toe of one of his sandals with one bare knee pressing hard into the other.
Miss Presswell laughed and played with the blond ringlets at Andrew's temple. "Yes, you look more like a girl than a boy, Andrew. This is Jason and he has something he wants to ask you."
Jason tried to swallow a lump in his throat. The boy was his own age, in a white blouse and a tartan skirt, mainly red and navy. Kate slipped the matching tartan waistcoat over his blouse, and was watching over the boy's shoulder.
"I feel wonderful, standing so close to you... sweetheart," muttered Jason. "Please may I kiss your soft, girlish lips?"
Miss Presswell turned to look at her sissy. He had changed his words, but she could see from the flush on his cheeks that they had sprung from the heart, and waited to see how he performed. She pulled the sissy's hands away from his face and held them for Jason to take in his satin gloved fingers.
"Mother, no, don't let this happen," pleaded the boy, trying to lift his hands again, but Jason clasped them into the front of his blouse as he'd been told. He wasn't going to let Miss Presswell have any excuse for sending out that photo.
He moved his Mary Jane toes forward until they were touching Andrew's school sandals, then he planted a soft peck, very briefly, on Andrew's lips. They looked into each other's eyes for a long moment, then seemed to sink into a second lingering kiss, in which their lips knew when to press, or slide, or pucker. Jason held his breath and opened his lips to clasp the whole of Andrew's mouth, while at the same time his satin gloves found themselves moving round his school blouse, sliding deeper underneath Andrew's waistcoat and hugging the sissy in his embrace. His tented panties pushed into the tartan skirt, and it was only when the point of his firmly stiffened penis felt the equal hardness of the penis behind the pleats that he realised what he was doing and sprang back with a gasp.
Miss Presswell's face was a mixture of intentions. "Hm," she said, clutching his arm, "I'm beginning to think you have real sissy instincts boy. You will now help Kate to fit dear Andrew with his school panties."
It could have been Kate's birthday, she was so quick to pull open drawers of panties and spread a dazzling variety of dainties across the glass of the counter. "Mrs Marchison," she cried, "would you like to select some lovely schoolgirl panties for your son?"
The boy's mother was in a high spirits after witnessing the sweet sissy kiss. "I want him in white satin," she declared, "with lacy prettiness at each leg. There's no point sending him to girls' school if he isn't as girlish as can be." She pointed to a pair of full cut panties in slipper satin with two inches of white lace at each leg. "There, sissy boy," she said to Jason, "put him into these."
Miss Presswell clicked her fingers and pointed across the counter. "A matching slip for him, Kate," she said, and the girl got one out, let it drop from the waist into a sweet satin flare, and passed it over. Jason steadied his fingers as he took the slip waist elastic from her, and crouched in front of the wretched boy's white knee socks. The sissy client stepped meekly into it with a moan of embarrassment, which somehow Jason shared as if they were suffering the same shame together. The satin slipped beneath the hem of his skirt, and Jason slid it higher, around his bare buttocks and hips. Then the boy's mother passed him the panties.
He found them so pretty as he drew them over Andrew's knees, up his smooth thighs and under his glossy slip. Another moan of hopelessness came from the boy as Jason made sure the waist elastic of both undergarments was evenly arranged all round his waist, but Andrew was in such arousal that Jason's hand inevitably brushed across the stiffened penis in its panties and slip.
The sissy schoolgirl's hand went to his cheek and he closed his eyes as if to prevent himself starting to cry. It acted like a signal to Miss Presswell, and she pulled Jason back against the ruffles of her blouse.
"I'd like to see the two of them admiring each other's panties," she said. "Mrs Marchison, would you mind showing your son's pretty panties for my sissy boy to admire?"
Jason shook with shivers as Miss Presswell held her arms round him, preventing his interference, and turned up the front of his paper-taffeta skirt and crisp petticoat. His panties had hardly been covered at all, but now it was obvious to the three women that his penis was tightly stiffened into the satin gusset, so that the double dome of his knoblet was pointing upwards in an eager erection.
"Oh look, they're both as excited as each other," declared Andrew's mother, holding her son's petti-slip and skirt against the front of his blouse, and she stepped forward, forcing him to inch towards Jason, so that the points of their panties approached to within three inches of each other. "Isn't that sweet, Andrew darling... having your girlie panties exposed in front of another sissy's panties? You can see how lovely he is feeling about your excitement inside your pretty satin panty gusset. Tell Mummy and Miss Presswell how you are feeling in your panties, dear."
Jason glance up at the boy's face, only inches in front of his own, and saw the wrinkling anguish in his face, fighting back tears.
"I-I'm feeling so feminine, Mummy," he blubbered.
"Feel the front of his panties, boy. It's what you're wearing soft, smooth satin gloves for. Fondle the shape of his penis to bring him sissy pleasure."
Jason released his gloves from Miss Presswell's arms and allowed them to reach in front of him, his hands cupped round the little shapes in the sissy's satin gusset but not quite touching them. There was a warble of desire from the boy as Jason cupped one hand under the satin-clad purse, and his eyes closed as Jason's other hand clasped the penis in his satin fingers, holding, squeezing, then fondling its length. Mrs Marchison tightened her grip on her son as his wriggles grew, until he gasped with sighs and his pantied gussetquickly surrendered to Jason, with a sudden dampening of his pantied point, followed by a spurting flood of sticky wetness.
Oh no, what would Miss Presswell do? What if he squirted into his panties too. Jason stood on tip-toe, rising above his urge to ejaculate, and he managed to hold it with a superhuman effort.
"Why, that's a lovely response, darling," said the boy's mother, grinning as she turned to Kate. "I'll take half a dozen of those panties, dear, if you please. Three in white and three in primrose."
"The secret of school panties for sissy-boys," explained Miss Presswell as she supervised Jason drawing Andrew's wet panties down his legs, "is to show him how feminine they make him feel... in his sissy bits and pieces. If he experiences real girlishness inside them, he will grow more girly each time he wears them. Jason..." and she turned her attention to her sissy boy who was threading the wet panties over the client's sandals, "you need to attend to Andrew's penis."
As he knelt up, his face was a couple of inches from the wet penis, now half flaccid and glistening with its recent ejaculation.
"Wash Andrew's penis, boy. With your mouth."
Another fainting fit came over her apprentice sissy boy. His eyes happened to catch Kate between Andrew's mother and the manageress, gritting her teeth with encouragement and making nodding signals. There was no alternative. And in any case, he liked the soft thighs and tummy that were bared in front of him as the boy's mother held up his petticoat and skirt. His heart was pattering feverishly again as he faced the glistening genital, opened his lips and took the penis head and all its shaft inside his mouth, closed on it, and softly licked it inside his mouth as if sucking on a lollipop.
Andrew moaned above him and tried to withdraw his pelvis, except that his mother braced herself to keep him still. Jason's tongue slithered and lapped, tasting the sweetness of the boy's jism, glowing with new feelings of girlish desire, sucking on the prettily shaped organ within his mouth. At last he felt a set of fingers resting on his cheek. It was Miss Presswell, almost with a smile on her face.
"That's enough sissy sucking, my boy," she said. "You can't spend too long on one customer. Put your sweetheart into a fresh pair of panties, so that he can go home."
Jason thrilled at how stiff Andrew's penis had become when he slid his lips off its helmet. How long had he been sucking it? He looked up and saw tears of shame running down the sissy schoolgirl's cheeks, while his mother was collecting two presentation carrier bags from Kate across the counter. He presented a pair of primrose panties to the boy's feet and slipped them over his sandals and up his legs. He flushed with soft emotion as he brought the gleaming panty to the top of Andrew's thighs, inched them up his hips and lifted the elastic over his newly stiffened penis, until the shape of the sissy schoolgirl's genitals filled the gusset of the panty. Jason found himself hauled to his feet by his pink ribbons.
"I've decided where I want you next, my boy," declared Miss Presswell, manoeuvring him past Mrs Marchison and back through the boutique the way they had come. "Serena," she called to the lovely blond assistant with short bobbed hair who had befriended him in his first hour in the store, "we need to change him; he's coming with me to the display lounge."
When he was safely back in the staff suite, he was glad it was Serena who was undoing his skirt and blouse and taking off his petticoat and panties. "What will I have to do in the display lounge?" he asked in a whisper as Miss Presswell got his change of clothes ready.
"Oh nothing much," said Serena with a little shake of the head. She held his panties where he could see the dampness in their gusset and gave him a big-sisterly smile.
"But Miss Presswell sounded like she had some hellish scheme in mind for me. Will I be changing sissies' panties again?"
Serena unhooked his bra and he was naked. "Probably that, yeh," she said in a hurry, and stood up as the manageress turned to them.
"Put him in these shoulder petticoats," she said, "and I want him in Snow-White knee-highs and crystal pumps to match this dress."
Jason's heart felt like it fell in his chest when he saw the pink dress hanging on the door of the closet. It filled out from the hanger as if it was a Square Dance petticoat. His mind was jerked back from it by Miss Presswell's voice.
"Miss Boothroyd? Hello, Monica. A word about your stepson."
Jason was all ears. Surely she wasn't going to tell his stepmother about the duties he had performed this morning?
"There's something you should know about him." She paused and Jason could hear his stepmother's voice as a dainty petticoat fell over his head for him to put his arms into. "Well he's just about steering on the right side of me. He nearly pushed me into exposing him as a sissy to a few of his friends, but that's just it, my dear. We have a real sissy on our hands."
A second petticoat fell over Jason as his breath turned into shivers of horror. What on earth was she going to tell her?
"His natural tendency is to touch and feel when he is faced with another sissy. I can see you didn't suspect sissiness in him, but this kind of sweet feelings when he is with another sissy is a sign of pure inner girlishness."
Jason let out a wail and his eyes filled up. What was she saying, this woman, and what was his stepmother going to think after being told such lies? He turned to Serena as she dropped his third petticoat over his head and let it slither out onto the others. He saw sympathy in her eyes and in the shape of her lips, and she put her arms round his petticoat frills to clasp him in a sisterly cuddle of pity.
"Don't let it worry you, hun," she said into his ear. "I love you when you show how delicate your feelings are, and how you love being dressed in pretty lingerie." She held him close with one hand between his shoulders and the other on the back of his hair. She was welcoming the idea of his sissiness. She loved him being a sissy.
"All right then," concluded Miss Presswell on her phone, "we'll sort some nice things for him when you pick him up at 6." As she put her phone into her bag, Jason's tears became too much, and ran down each of his cheeks onto Serena's uniform blouse.
"You need to understand the terms of your safety from public exposure, boy," said Miss Presswell as Serena disappeared to fetch the rest of Jason's clothing. She picked up a length of lavish pink ribbon. "You are about to work closely with my clients and I will not accept any form of grumbling or complaint. Such nonsense would immediately see your photographs scattered amongst your network of friends, is that clear."
Jason nodded with sobs as he stood to have the ribbon threaded into his hair and fastened into a bow that stood high above his hair.
"When clients want to kiss you, you offer your lips," she said. "If they want to remove your panties, you make the same sort of 'Ohhh!' and 'Goodness!' sounds that a girl would make in similar circumstances. You will not resist or express the slightest reluctance, no matter how intimately my clients want to cuddle with you. I will be watching your face, your penis, your every move, boy, so be careful."
Jason was shaking like a leaf as Serena returned with an armful of things for him. It sounded like he was going to be mauled by mad dogs and thrown to the lions. The silence was interrupted only by sniffles as he sat for Serena to thread the most delicate white stockings up his legs with lacework, pretty patterns, white seams up the back of his legs and decorated tops to hold them above his knees. Onto his feet she put a pair of crystal kid pumps with narrow heels that must have stood three inches high. He held his arms wide to keep his balance, but he had to grab the table as she presented his panty to his feet. It was rose pink, arranged in a drape from one hip to the other, encrusted with roses that were embroidered into the satin. The back of his panty surrounded his buttocks in rows of ruffled satin down to his leg elastics.
"Hands in," ordered Miss Presswell, and Jason was put into a pair of white satin bridesmaid gloves, each with a white rose that looped onto a button at the back of his wrists. There was a sizzle of material, and Serena had his dress unhooked from its hanger. Somewhere at the back of his mind was the fear of being photographed in it, and hung out to dry as a sissy for everyone he knew to scream with scorn at him, but as she gathered it onto her arms, and as her hands came out at the top, it seemed that his body was waiting eagerly to be dressed in its gorgeous girlish prettiness.
The white satin lining hissed over his head, and all of a sudden he was surrounded in pink gingham, surmounted with a wide collar of white satin and with puffs of white satin at each shoulder. It was so silky, he let out a warble of emotion. He was feeling delicious in his penis; it was the way the dress spread out over his petticoats to surround him with girlish sweetness.
Serena fastened the three large pink gingham buttons down his white bib, making him gasp. He gave his hips a tiny wiggle, and the dress swayed from side to side, increasing his girlish emotion. He got a fright when he realised he was being watched by Miss Presswell, who lifted her eye-brows as if to say: "I told you so." Her ruffled pink bosom swelled with a deep breath and she reached a hand forward for her sissy-boy to take.
His dress sizzled with precious sounds as he followed through the different departments, past ladies here and sissies there, until they came out into a larger room with a larger group of ladies in it than Jason had seen in any other part of the boutique. They were gathered on one side, to watch some kind of demonstration, and then he began to get the picture from glimpses he caught between ladies' coats and skirts.
There was a cot in the middle of them, into which they were peering in hushed attention, until suddenly there was a unanimous "Aaaah!" and "There's a good sissy!" and a round of applause as they all exchanged comments with smiles and giggles. A tingle of worry swept over Jason. There must have been a sissy at the centre of all this attention, and the way Miss Presswell was using him this morning, it could be...
"Ladies," she announced as the group spread out a little, "our next demonstration will be provided by our boutique sissy, who is going to be fastened into our Sissy-Suck High-Chair. It's an item that we like to demonstrate here at Pretty Boy, especially since it provides our lady clients with such pleasure."
Jason's mouth dropped open as a dozen women turned towards him and almost ran to gather round.
"Hello, Jason," he heard, and two women parted to allow the speaker to step through. "I - didn't know you were a sissy."
Holy cow! Gareth Mitchell's mother, here in Sissy Boy!
There was a chorus of agreement from the circle of smiling faces. Jason had to protect himself, from exposure.
"M-Mrs Mitchell, I... Please don't tell Gary. Don't tell him you saw me in a dress."
"No... no I'm not!" he retorted, then remembered Miss Presswell beside him. "I mean... I mean, thank you... Mrs Mitchell. You're very... kind. But please don't tell Gary you saw me here." He had to find a reason which would put her off, because she was looking like she'd got the best bit of gossip in weeks... no, years! "C-Can we keep it a secret, Mrs Mitchell... pleeeeeeease?"
"Aaaah!" cooed all the women. "He doesn't want his friends to know." "Isn't he sweet." "He's nearly crying, look."
Jason lifted his free satin glove to prevent a tear from leaving his eye, and then the other. His glove cupped his face as his blushes overcame his cheeks, and in a moment of panic, he turned to Miss Presswell and buried his face into the satin frills of her blouse.
He was surrounded with Aaaahs and giggles and felt women's fingers stroking his hair, his arms, his dress, and the tears burst from him in a storm of emotion.
Miss Presswell lifted his chin out of her bosom and he saw the chair he was going to sit in, inching forward on its runners from drapes of white net curtains and humming to a halt. It was in pearlescent white plastic, with pink cushions on the seat, the back, the arms and the legs. He peered through the water in his eyes and shook with sobs as she positioned him with his back to it, made him sit on the rubber-textured cushion and moved his bottom to the back.
A sea of powdered, lip-sticked and mascara-ed faces surrounded him as Miss Presswell secured him into the chair and his breathing was thick with a confection of sweet perfumes. A belt three inches deep passed under his dress and fastened into a buckle at one hip to keep his waist immovable. "Your sissy is secured with a series of straps," she said, fastening a narrower belt over his left thigh, followed by another over his right. "Here at Pretty Boy, we believe that the femininity of the sissy increases in proportion to how helpless he feels, and a good indication of that is to have the dear thing held perfectly still so that you can do what you want with him. There: he is held at waist, thighs, legs, arms and chin."
There were "Oooohs!" from the women and gloved applause. "Isn't that a bit dangerous for the sissy's life?" asked the woman next to Mrs Mitchell, wearing a lilac coat and wide brimmed matching hat. "I would have thought his breathing might be stopped with his head held between those satin blocks strapped together under his chin."
"Well you can see that Jason isn't suffering at all, Eileen," returned Mrs Mitchell. "He's not very happy, but he can breathe all right. I like the way his warm, soft flesh is so... unprotected. Can we touch him?" she asked.
"Of course," replied Miss Presswell with a gracious turn of the head. "Be my guest. Please treat our sissy as if he were your own."
Jason listened in horror as the ladies gathered closer on every side of him, so that their smooth coats and silky dresses brushed and slithered all over his legs and arms. There was a clunk beneath him and then a hum, and he found his legs rising and his chest and head sinking back, until he was half way between sitting up and lying down. It meant that the bust of Mrs Mitchell's salmon pink dress was almost touching his cheek, and her shiny dress buttons danced in front of his eyes as she spoke to Miss Presswell and the rest of the women.
"Let me tell you about Jason," she said in an excited voice. "Jason Boothroyd, to be exact. He can sometimes be quite rude and... pig-ignorant, in my opinion, but seeing Jason wearing a little summer dress with those dreamy white puffed sleeves and a lovely girls' white collar changes all that, don't you agree?"
Everyone agreed with grins and giggles. "And look at his petticoats," she went on, lifting the light gingham material and frothing her pink gloves through one layer of net after another. "No wonder his legs look as good as any girl's."
Jason whimpered with emotion as frissons went through his thighs and legs from the frolling of silky gloves and blouse sleeves.
"And such dainty, deeply sissyish panties," gushed Mrs Mitchell. "Take them down for him, Eileen. Is it all right if we slip Jason's panties further down, Ma'am?"
"Oh... oh pleeeease," gasped Jason, bursting to stop them but knowing he mustn't annoy Miss Presswell.
"I can see that the little dear is becoming quite overcome by his feminine surroundings, judging by that little point above the front of his panty," said Mrs Mitchell, curling her lips with ironic delight. "With Jason looking so sweet and girlish in his dress and hair ribbon, I'd love to see his little pee-pee."
"Ooooh, my goodness! Ohhhh!" he blubbered, barely holding onto his tears.
There was a squall of laughter, which quickly subsided as Eileen and a woman on the other side made a delightfully long process of easing his panty waist over his hips, slipping the lace trimmed legs down a little towards the straps that anchored his thighs, and lifting the satin gusset over the point to reveal the helmet of his stiffly erected penis.
An "Aaaahhhhhhhhh!" of admiration mingled with delight escaped every woman in the circle as every pair of crimson lips seemed to be close enough to reach down and kiss his exposed helmet. "Isn't it dainty?" "A little sweetie!" "I've never seen such a girlish penis, have you?" "No, it's a girl's penis, I'm sure." And four or five pairs of fingers, some of them gloved, held his stiffened organ by the shaft, the helmet, his testacles and the most sensitive parts of his legs and groin.
"What a sweet little sissy you are, Jason pet," gushed the largest lady of the group, and she lowered her fully made up face to his, her eyes locked onto his defenceless lips, and spread her full lips onto his in a slavering kiss that rippled and slithered all over his mouth... without leaving him... kissing and sucking... sucking and spluttering, making his penis reach higher, to welcome the women's hands, almost thrusting into them... and then surrendering, as his jism came, and squirted and shot into the air and shot again, to a squeal of delight from all the women present.
"Well done, ladies," chuckled Miss Presswell as she looked down on Jason from above his head. "You have convinced me of something that was only a hunch until now, and that is that Jason Boothroyd is most definitely a sissy like the rest of them."
There was another round of applause, this time with sticky hands and wet gloves, and Jason found himself kissed by every one of the women in turn, ending with Mrs Mitchell, who pushed her tongue inside his mouth and then stood beside his chair in such a position as she could lift her skirt and grasp his hand, to pull it between her legs and make him finger the gusset of her panties.
In part 3 poor Jason is fastened into a creaming chair for the pleasure of ladies, gentlemen and sissies.