Jason's Day At The Pretty Boy Boutique (Part 4 Of 4) free porn video

Jason's Day in the Pretty Boy Boutique (Part 4 of 4) As soon as he finishes college, Jason Boothroyd finds himself having to work in panties and dresses in a sissy boutique. He meets with sympathy from the girl assistants, but lives under the threat of internet exposure from the strict manageress, Miss Presswell. In this chapter Jason must entertain ladies who have long understood sissies and delight in using them. He does his best, but perhaps wasn't expecting the very effective games they want to play with him as their captive. Chapter 4 - Jason Is Used By Women Clients Serena put the finishing touches to his makeup, softening and blending his cheeks so that they were warm with emotion and girlish attractiveness. In any other circumstances, he would have loved being fussed over by two such pretty girls a couple of years older than himself: Kate with her hair bobbed, and Serena with her blond hair flicked up so deliciously at the ends. He had to have more photos taken, although he was less neurotic about it now than he had been that morning. He told himself it didn't matter now, because he wasn't going to protest over his sissy duties, and that meant that Miss Presswell would not be sending his shocking photos to anyone he knew. He had grown to find his sissy self more acceptable and looked sideways into the mirror to ensure his light brown hair was neatly bobbed and his fringe was even above his pencilled brows. He especially liked feeling aroused by the feminine clothes that surrounded him and... well... everyone was being so nice to him. He gathered his courage as he stood being photographed in his new dress, and made a suggestion to the manageress. "Miss Presswell... I'm not going to refuse any sissy duties and... I'm going to be a very good sissy for the Sissy Boy Boutique." She angled her high blond hair and well powdered face to one side with its black beauty spots on either side of her mouth and looked suspicious. "Oh?" she said. "So I was thinking you don't need to keep my photos on hold... ready to send to my friends at a moment's notice." The air was frosty, not least because Serena stopped taking pictures and pursed her lips to take a deep breath through her nose and let Miss Presswell answer. "I'm glad you've decided to be submissive and obedient, Jason, but those photos are a matter for me to decide, not you. They will stay available for some time yet, and after a week I'll consider your behaviour. Don't forget, it's instant and willing obedience that I want." She turned to Serena. "Put him half a dozen pairs of panties in a bag. He's going to need them." Jason turned back to the mirror. Would she ever be satisfied, or was he always to live under a threat? At least he could find pleasure in seeing himself in soft, delicate girls' clothes, like this beautiful pink dress with widely puffed sleeves and a broad collar edged with pink lace. The dress separated so shamefully in the front and had integrated petticoats filling it out so widely to halfway down his thighs. His legs felt so tightly encased, in white floral patterned stockings pulling against such pretty, pink garter straps, and with high heeled shoes in pink kid, matching his wrist-flaring gloves and his dainty handbag. But it was his hair which made him feel deliciously girlish. Did he really think those thoughts that morning? Feeling welcome desires and sexual thrills about looking and feeling like a girl. His hair had been trimmed so that he had a dark, very straight fringe across his forehead, and it was shaped into a girls' bob, with a white flower pinned into each temple bringing out his lipstick, his eye lines and shadow and the soft glow of his cheeks. His collar made a smooth spread of pink satin over his shoulders, giving him the face of a made-up little girl, and he swelled with sexual arousel. "Wake up!" ordered Miss Presswell. "You're coming with me. You are expected by some ladies, who have been waiting to meet you for fifteen minutes and you'll have to apologise." She took the bag of panties from Serena and opened the door to the boutique. "Good luck, Jason," said the girl softly, "and enjoy," and her hand caught his bare arm with a pinch of support. Miss Presswell must have thought she no longer had need of reins to keep her sissy in check, for she marched Jason alongside her, hand in hand, through the departments of the boutique and under the arch that said School and Discipline Department. The mannequins wore school uniforms: mostly white blouses worn with pleated skirts of green, grey or plaid. There were Japanese sailor-girl uniforms too with woolly knee socks and dresses for little girls school games, in green, blue and yellow gingham. As they rounded the corner, a notice on the wall said: "Sissy milking room" and "Jason will be here from 2-4pm". As Jason was led towards a collection of armchairs and settees, three ladies rose to their feet in sizzles of dress material and greeted the manageress. "What a dear boy," they exclaimed almost as one. "Isn't he a darling. Is this the sissy we can play with?" "This is Jason Boothroyd," declared Miss Presswell, her hand gripping him more tightly. "He lives at 25 Wiltshire Crescent, if you would like to get in touch with his stepmother. I'll give you her number later." "Ohhhh!" gasped Jason. Why on earth was she telling these women his address? "Miss Presswell!" he cried. She had suddenly widened his ordeal, from boutique sissy to... well, to being a sissy outside Pretty Boy as well. Miss Presswell and his stepmother must have worked this out over the phone. His right leg slid across his left in a spasm of defeat and his free hand covered his lips with shock as he just stopped himself from burying his face in the collared bust of Miss Presswell. He was caught. Her control of his facebook page meant that he couldn't object, and from feeling quite good about his new sissy sweetness, everything returned to being a threat. He was weak and defenceless again. "Oh I did like that little flurry of emotion," declared one of the women as she came up to him, her black taffeta skirt surrounding his legs. "He must be so girlish and ready to cry." Jason panicked. He tried to spin away from her but Miss Presswell was behind him. "No, I... I'm not going to cry," he bleated, and in spite of himself, his hand found itself on the ample bosom of her blouses in an effort to fend her off. "Oh dear, a little bit of a struggle," declared the woman, seizing Jason's hand and stepping forward to crush him between her blouse and skirt and those of Miss Presswell behind him. "Don't worry, Hilda," cried Miss Presswell, pulling Jason's arm into the small of his back so that she could secure it into a bondage sleeve, "the little sissy needs to be cuffed into submission." His other arm was pulled behind him to join the first, filling him with fright. He felt his arms being pulled together and fastened with hooks from wrists to shoulders, holding them helplessly together. "What are you doing to me?" he blurted, feeling as if his dress was being pushed out ahead of him, but Miss Presswell was not satisfied, and as the women surrounded the youth and sat down with him, pulling him onto their laps, he found his knees equally gripped together in a cuff of white silk, made for the purpose and fastened behind his legs with hooks and eyes as if it was a bra. "That sissy-cuffing set is delightful," said one of the women as the manageress stood him on his feet to face the women. "I could do with one of those for my Benjamin. I'll be marrying the poor little sucker in two weeks." The other two women laughed as Miss Presswell explained. "This is a the Busty-Bonder set," she said, forcing Jason to drop onto his silk-fastened knees. It has a gag to go with it, which I'll put on him for the punishment he has just earned. You can imagine how its real value becomes clear when the sissy has had his bust fully developed. Now, Jason," she said, "you will apologise to Miss Von Slip for the gross rudeness you have just shown in laying your hand on her bosom." Jason looked up at the smiling Miss Von Slip over her very ample bosom in a silvery satin blouse, over which she wore a loose green blouse unbuttoned like a tunic. She had her hands, at the end of very full sleeves, together in the lap of a fully petticoated skirt that sizzled as she sat. "Repeat after me," he heard behind him. "My respected Miss Von Slip..." Jason wondered if this was dream or reality, but his mouth responded like a parrot. "my place is at your feet..." Jason echoed her words. "and I humbly beg you... to punish my naughty male behaviour... with a good spanking." Tears filled his eyes as he said it, finishing with: "I promise to be an obedient and effeminate sissy for you to play with." "I should think so too," declared Miss Von Slip. "My own boy is at sissy school this afternoon - Clive is his name, although it will be Colette soon - but if he were to raise a hand to me, he would expect to receive a good thrashing with the leather tawse, so that is precisely what I will do to that naughty sissy bottom of yours... if Miss Presswell will oblige me by fastening you into a whipping frame." A shock passed through Jason's body. A whipping frame! He turned, hoping to hear Miss Presswell deflect the woman's threat, but her black lined brows were lifted in agreement. "What a good idea, Hilda," she said, leading Jason backwards in short, high-heeled steps to a cushioned stand in black leather. "My first response to his behaviour would have been a most humiliating public revelation for the sissy, but he will be grateful to you for giving him the choice." He found himself bending face-forward, with his dress pressed over the curved top and falling forward so that his head disappeared from view inside upturned petticoats. A thick ribbon was threaded from the front of the stand, through loops in his single-arm sleeve, to its receiving hook on the other side, so that his upper torso hung upside down inside his skirts. A yank at his panties pulled them down to his stockings. "Well, sissy-boy," Hilda cried as she selected a long-handled, leather paddle from a rack on the wall, "what's it to be: a severe paddling for a naughty sissy? Or Facebook?" "A severe paddling!" came the instant cry from his petticoats... "please." And to make sure he was getting it right, he tightened his courage and added: "... for a naughty sissy boy". The ladies applauded and watched as Jason felt the touch of a flat, cold paddle taking aim, then WHACKKK! it descended on him with a sting like he had never dreamed possible. His cry filled the room and his buttocks caught fire, or that's what it felt like. He also felt his petticoats being parted, and his lips being forced apart by Miss Presswell's fingers for a ball to be pushed inside, followed by the tight wrapping of more silk as he was gagged over his mouth. "That's a very effective paddle, Alicia," he heard. "How much would that one cost?" "The Rump Thumper is very popular with nannies," he heard. "Three hundred pounds, give or take. And worth every penny in its effective correction of sissy behaviour." Without warning, a swish through the air brought a second THWACK! onto Jason's bottom. His instinct was to roll off the leather frame, but he couldn't move. Another THWACK blistered his painful globes. He screamed, in a muffled groan, then another bit into his tightened, searing flesh. If only he had begged Miss Presswell to send out his photos! He couldn't take any more of this. But mercifully he found his ribbon being unhooked, and moments later, with painful buttocks, he was stepping his way back towards the women, his panties at his knees and his dress recovering its shape as Miss Presswell straightened and fluffed it all round him. "It doesn't pay to be a naughty sissy," she scolded, motioning the ladies to take their places in the narrow horseshoe couch with their skirts forming a silk and taffeta bed and their stockings all together in the middle. Eager bloused arms helped to draw him down into their laps and it was a blessing to feel the cold taffeta and silk beneath his buttocks as he was pulled and sizzled into a sitting position with his bound knees and white Mary Janes out in front of him. He was introduced to the ladies, and his gag and ball were removed so that he could reply politely. "Say hello to Miss Girth," he was told as he sat sheepishly with his panties at his knees and his dress flaring in front of him with no hands to protect himself. "Ask her what game she would like to play with you?" "H-Hello, Miss Girth." Jason was sitting in the laps of Miss Presswell and Miss Von Slip, so that Miss Girth and the other woman were more in front of him. She was a big woman, with blond hair cascading to her shoulders, and everything about her face was rounded and full. She wore a dress that was green with a black pattern and seemed to spread everywhere, with a black belt, big white collar, white flaring cuffs and white flaps to her pockets. "Can I p-play a game with you, ma'am?" "Why honey, of course you can," she said, reaching her fingers to Jason's face and smoothing his cheek. "Do you like ladies who want you in their panties, sweetheart?" Jason felt Miss Presswell's fingers tighten on his arm sleeve behind him. "Yes ma'am. I... love ladies' panties." "Ah," she chuckled, "but do you like pressing big lovey kisses into a ladies' panties, and welcoming her when she puts you in your place?" Jason wasn't clear what she meant but he knew the right answer. "Yes, ma'am," at which Miss Girth struggled to get to her feet and so did everyone else. Jason found himself being laid on his back on the settee, with his head at one end where there was no arm rest. His legs were lifted in the air as someone sat beneath him for his bottom to be rested back on her skirt and once again he was surrounded with women, only this time with his head facing up from the seat, while Miss Girth stood beside him with armfuls of her very wide dress held up to reveal her large, silky white panties. "Let's play sissy panty face squashing," she laughed as she sidled closer until her high heels were on either side of Jason and the gusset of her huge panties loomed above him. "Do you want to kiss Auntie Marilyn's panties, sissy boy? You can kiss them with your whole face." A shock fizzed through Jason from an unexpected quarter: his penis felt the soft slither of delicate lingerie as someone wrapped it in a pair of silk panties. He was already feeling strangely roused in the punishment chamber: it could have been the way these women watched him, as if they were birds of prey and he was a little kitten they could eat... after they had had some fun with him. The pleasure in his cock helped him to submit more easily to Miss Girth. Her panties were deeply feminine, in finely corrugated silk with dainty embroidery outside each leg, and... she was inviting him into them. "Y-Yes please, Miss Girth," he bleated. "That's right, my darling sissy boy," she said, descending closer as she looked down and the bunches of her petticoats darkened his face. "You can kiss and kiss and kiss Auntie Marilyn's panties for her, under her dress." The silk of her crotch met his nose as he realised he might need a long, deep breath. From his nose, the panty flowed out over his cheeks and spread round his whole head as the soft flesh of her backside pinned him to the couch. She was talking to him, he knew, but all sound had gone as he lay motionless under dark female pressure. A second pair of panties - or was it a slip of a nightdress? - played with his cock, and suddenly Miss Girth's whole panty-taut bottom slid up his face a few inches and then slid back again. "Oooooh!" she moaned as her crotch lifted for a second, giving Jason a fleeting view of her green bust and above it her puckered red lips, trembling with lust. His cock swelled as she descended again, this time with wet silk that smelt of salt or even fish. Hands played with his stockings and his sore buttocks, he struggled to find his breath and wanted desparately to be released. Then suddenly he was, only to see the light of the discipline chamber and to hear Miss Girth gasping and saying: "I'll get him this time." Her panties were pulled down onto her stockings, and there above Jason were the naked, gleaming lips of her vulva, panting for his mouth, aiming to plant themselves onto his nose and tongue. A growl of desire went through her as she landed her wet vulva on his lips, sliding over his nose and mouth, and sinking until his face was pinned down in folds of female flesh. She rocked a little, moving her labia, working deeper onto Jason's nose and tongue, drawing his emotions into her genitals as he knew he was paying her respect and providing her with pleasure. He found that his sissy nature liked that. He wanted to make her feel powerful and maddened with lust, and he felt the pleasure mounting in his cock towards a climax of sweetness. Then he felt her reaction: a shuddering in her haunches on top of him. She weighed more heavily and held him captive... rubbing her labia as hard as she could into his face as she felt the rise of her delight. It seeped out of her so that she slipped and slid with slucks of juicing, to and fro. Her wetness thrilled Jason, all over his lower face, and his pleasure mounted, higher, until he was loving it. He came explosively into the panties on his cock, as hot juice soaked his face and Marilyn Girth raised her weight a little so that she could wash her juices to and fro, up and down her sissy's face, and hold him there as shudders of pleasure ran through her body and her legs. "We-e-ell," she declared, sitting on his chest and looking down to where his chin peeped from her wet labia, "you've got a clever little sissy boy here, Alicia. I think I sensed it as soon as I held him in my panties: there's a deep girlish need in his face and his body." "And in his little clittie," said one of the other women. "That was a more girlish ejaculation than I get from my Clive. Miss Girth hauled herself off Jason, letting him draw a deep breath, and her oceans of petticoats wafted coldly on the juicy wetness of his face until Miss Presswell wiped him with the panties she was holding. "Up," she ordered. "Well done, Jason," and she held him by his single sleeve as his dress was straightened for him, "but you haven't finished. I didn't hear you thanking Miss Girth for the nice time she gave you under her dress." Jason apologised to a giggling Miss Girth as the women organised themselves in rustling dresses and blouses, then pulled him back into the same position as before, with the four of them around him and his legs fastened together across their skirts. He was astonished by the sweet after-glow of his orgasm, which brought him a calm feeling, knowing that he had done what Miss Presswell wanted him to. But at the same time, he felt a kind of pleasure that was new to him: a wish to be submissive to Miss Girth, a forceful woman in her forties. And it weasn't just her; he found himself at the mercy of four older women, Miss Presswell included, who all seemed intent on using his weakened body for their pleasure. Their hands were all over him, fingering his cock and testies, slipping under his suspenders, smoothing the soft flesh of his thighs and exploring deep underneath his petticoats. "It's my turn to bring another gush of pleasure to our sissy boy," said the third woman, who had supported the other two clients but hadn't said a word to Jason until now. "I've got to learn how to make my new husband spurt and spurt as much as I want him to, and this little sweetie is so like him." "This is Miss Mellsworth, Jason," said Miss Presswell into his ear, unhooking the back of his knee cuff and separating his legs across the skirts he was sitting on. "She will be marrying a sissy in a couple of weeks time and he is only two years older than you. So she can practise on you to get ready for training him." Jason looked at Miss Mellsworth and felt his maleness draining out of him. He wanted her to treat him with womanly contempt. Her blouse was so shiny and frilly and her smooth skirt swelled all around her over what must have been five or six petticoats. Her crimson lips smiled at him but pursed in a thinly veiled sneer and her dark hair was in a full perm that surrounded large silver globes at her ears. "Your blouse will make him crawl at your feet, Sheila," chuckled Hilda Von Slip. "You should take off your skirt and give him a taste of your pantied crotch." Her skirt was in grained peach taffeta, evidently stiffened but as glossy as her cream blouse. It buttoned down the front in large, taffeta covered buttons which rose over her knees and disappeared under Jason's thighs. His stockinged legs were spread apart across her skirts as he sat facing her obediently, having his penis fondled and his legs stroked, hopeing madly that Miss Sheila Mellsworth would lift her skirts and present his face with her panties... or her blousey breasts... or just smother him in kisses and lustful hugs. "His little clittie is such a cutie, I've simply got to cuddle it closely in my skirt," she said, her satin breast heaving with roused passions, and her hands dug deep round her skirts and pulled her whole skirt into view. Miss Presswell and Miss Von Slip separated Jason's legs wide. "I want to make him fall in love with it," she said, and she spread out as much of her skirt as she could, slid one hand underneath so that she could lift it from its lining and gathered the taffeta skirt buttons round his erected penis. "There we are, sissy boy," she smiled, and a little warble of emotion passed his lips as she grasped him through the skirt material. "Let Auntie Sheila make little Jason fall in love with her luverly slippery skirt. It's what you want isn't it pet?" Jason slid lower in the women's skirts as the cold taffeta kissed every inch of his cock and convinced him pretty quickly that he was going to rise to a peak of pleasure thanks to its pure femininity. "I think you're right, Sheila," said Miss Presswell as she wrapped her blouse sleeves round his neck and actually pressed a kiss onto the top of his hair which was just in front of her lips. She held his face between the two long buttoned cuffs of her creamy pink sleeves. "My Pretty Boy sissy looks very pleased indeed to be pushing his cock into your skirt buttons. You need to ask Miss Mellsworth to masturbate you to a peak of sissy pleasure, my boy. Ask her now." Jason's efforts were focused on trying to hold that peak of pleasure down, and he was fighting a losing battle. What would happen to him if he got his jism on a client's skirt? It wasn't something he wanted to risk. "Oh please, no," he whimpered as feminine hands fondled him beneath his dress and along his stockings. "I can't... I can't sto...Ohhhhh! Oooohhhhhh!" He tried to hold it back but... a white droplet peeped out of his helmet... and another... then little pulses of cream shot into the air between Miss Mellsworth and Miss Girth, drawing bursts of laughter from all three clients. Miss Presswell squeezed him tighter in her arms and shook him from side to side with satisfaction. "That's a good sissy, my boy, but you've only just started. The ladies want a lot more pleasure from you than that. What about you, Hilda? Would you like to fondle him off next?" "I'd love to, my dear, and I want to suck his effeminate little soldier and fold it into the front of my blouse. I think he'd like that." Jason was shaking his head. He knew he couldn't manage another spurt of jism. How long would they keep on pulling and fondling him? His cock was already starting to ache. But Miss Presswell wanted her clients to enjoy themselves. "You can kneel between the couches and get close to him," she said. "I think he needs to learn about the attractiveness of a blouse like that." The women giggled with delight as they changed places and held his legs wide apart. His eyes couldn't leave Miss Von Slip's blouse as it unavoidably smoothed against his stockings and caught the light in flashes of satin brightness. It was a classic blouse in lilac satin, with a big collar which she wore open at the neck, with full, billowing sleeves and a waterfall frill on either side of the front buttons, and suddenly there it was between his legs as they were held by the other two clients with his Mary Janes on their skirts and his knees in the air. "Sissy boys must learn to appreciate their Mistresses' nice clothes," smiled Miss Presswell, talking from above his face as she held his cheeks in her hands with his head in the lap of her skirt, in front of the buckle of her vinyl belt, "and I think your blouse will appeal very sweetly to his feminine nature." "I think so too, sissy Jason," smiled Miss Von Slip, leaning her whole body forward so that her face was only a few inches from his and her blouse smoothed its ruffles over his penis and stomach. "Feel how smooth my blouse is, darling, as I slide it on your sissy clittie like this. Mmmmm, is that nice?" Jason's eyes lidded with feelings that he didn't want: a shameful liking for her blouse and waves of sweetness in his feeble groin and legs. "Answer Miss Von Slip," prompted Miss Presswell, giving his head a shake in her hands. He did his best as satin and buttons found the most sensitive parts of his cock. "Y-Y-Ye... Ohhhhhh!" he stammered, his penis rising into the waterfall frill. "I think sissies sometimes need their pretty clitties to feel loved, don't they, Jason... with kisses and sucks that show how sweet and feminine they are," and she slid her blouse down his body, over his cock, until her crimson lips smiled at him from in front of his helmet. She planted a smiling kiss on its dome, then parted her lips enough to close them again and hold his helmet half in and half out of her mouth. He felt the tip of her tongue caress it, and suddenly the collar of her blouse sprang into view as her hands lifted it around her face... and waterfall frill as well... so that her hands held his shaft in satin blouse collar and frills, softly smoothing over its length as her sleeves billowed in front of his stockings. Jason nearly fainted as pleasure filled his whole body but especially in the caresses over his penis. She smiled as she kissed, occasionally slipping her lips that little bit further to enclose his knob before drawing back with ripples of her tongue. Then he heard words that filled him with even more of a surge of desire... from above him... from Miss Presswell. "You're a sissy, Jason," she said, looking down at him, unsmiling above her full Puritan blouse collar, in a matter of fact tone. "You are a sissy and you love women's and girls' clothes, don't you?" And with that his penis filled with desire and his cream came spurting through into Miss Von Slip's mouth... much more than he thought he could ever produce, and she gulped and swallowed, sinking her lips down the length of his cock with her collar round her hair as she rose and fell with short movements, sucking out all his cream, drawing out all his devotion for her lovely blouse and the power of these dominating women. For some reason, an enormous wish to cry overcame him and he melted into tears as Miss Von Slip withdrew her mouth and held his penis in her fingers, planting delicate kisses on his knob and watching him, with the other women, as he cried and cried in their laps. He saw their expressions of sympathy as their hands fed a fresh pair of satin panties up his stockings and straightened out his dress, and he felt the soft side of Miss Presswell as her fingers frolled his neck and his cheeks from above. "Sissies are allowed to cry," she said. "That was a lovely sissy feeling, being blouse kissed and sucked by a lovely woman while you were wearing your lovely dress and stockings, wasn't it, pet?" Jason's tears kept flowing, helplessly, but he nodded and answered "Y- Yes, Miss Presswell... thank you." He was hugged and petted by all three women as they passed him amongst them on their laps and kissed him again and again, until, when the manageress got a call on her mobile, she had to bring their session to an end. "Jason will have to say thank you and good bye, ladies," she said; "his mother is here to take him home, and he has to be changed and got ready. This wasn't the good news Jason thought it would be, but as he was led out of the Milking Room, the sound of "Good-byes" falling sweetly on his ears, he wished he could have stayed longer to be cuddled and petted by the lovely middle aged women. "So, Alicia," said his mother, watching Kate undressing her stepson while Miss Presswell brought his tee shirt, pants and jacket with his normal shoes on top, "what kind of a sissy has he been?" Jason peered round Kate to see the manageress as she replied. "Not a bad one, Veronica," she said, "but he still has much to learn... starting tomorrow." A few hours earlier, these words would have devastated Jason, but on the way home and as he lay in bed that night, his cock told him he couldn't wait, and he wondered what delightful lingerie and dresses he would be put into once he got back to the Pretty Boy Boutique. THE END