Part 1: Jason learns to cooperate with customers.
"Alicia, lovely to see you, darling. I've brought him along as we arranged."
Alicia Presswell turned from the display of frilly girly panties she'd been doing in the glass-fronted counter and stood up with a crimson smile between beauty spots. "Veronica my dear, the pleasure's all mine," she said. "My oh my, your hair is adorable, sweetheart; and your coat... it must be velvet and satin."
Veronica Boothroyd wafted a kiss on both of the woman's cheeks, at arms' length so as not to knock the wide brim of her hat, and said: "Jacquard silk, dearest. I paid a year of my late husband's salary for it." She gave a full turn: all violet and black with gold collar and cuffs. As to her coiffeur she never allowed anyone to outdo her hair creations, and her generous lips smiled all the more over her friend's blond beehive which was only half as overdone.
"Well, well, well," said the manageress, putting down a dozen pairs of panties on the glass top of the counter, "this must be Jason... your darling stepson."
The youth in question stood behind Veronica and ignored such comments. He had a game to be getting on with on his phone. There was a moment of hush as the two women looked at him with disgust. To make sure they did, he spread his denim jacket and stuck a thumb in his jeans pocket, so that they could read his tee-shirt: Fu*k off or I'll call the P*gs. The manageress spoke again.
"I'm pleased to meet you, Jason. When your stepmother spoke to me last night about how difficult it was for you to find a job during your college holidays, I was over the moon. You'll make the ideal assistant here at Pretty Boy."
The youth looked round him without lifting his head and snorted. "You - are - unreal," he said. "This place sucks. Look at that!" and he pointed to this mannequin of a boy, dressed in a satin suit of wide, calf-length culottes and a jacket in pale blue over a blouse. "It makes me sick. Another stupid idea of yours, stepmother. We're going."
He spun on his heel and... Whoa! What the fuck! He found himself looking into two separate pairs of tits. Blondes, both of them. 'Fuckin' dreamy' he thought.
"Yow-wee!" said the one with her hair in a pageboy bowl, perfectly round. She had the sort of lips he just had to kiss: glossy pink and cheeky.
"Phooorrrrr!" said the other, looking down at him. Her hair shone and bounced in flicks around her neck as she looked him up and down. "I'm Kate," she said.
Alicia Presswell sniffed and fluffed out the pink ruffles on the front of her blouse. "I'm afraid not, girls. Master Jason doesn't want to join us."
"A-Ah!" said the college student, wagging his finger as he took in the cute faces in front of him. "I didn't say that, did I?" and he pulled his jacket shut. "Working with such talented colleagues is just my thing." He gave the girls a wink. "I guess you've got yourself an employee, ma'am." He could do with getting away from his pain of a stepmother for the next five or six weeks.
"I'm glad you've changed your mind," said Miss Presswell. "You can start right away. Girls, you know how to prepare a new male assistant. Help Jason into his Pretty Boy uniform."
Jason couldn't believe his luck. He was definitely going to get off with one of these chicks. They were taller than him in their high heels, both wearing a uniform themselves: starched white blouses plunging low, with puffed sleeves at the shoulders and white elbow length gloves; then little pleated skirts in pink with straps over their shoulders making them little-girlish, and so short you could see all their stockings and suspenders on gorgeous thighs. They linked their arms through his and trooped him through the shop and into the back.
Serena with the short hair helped him off with his jacket while Kate pulled his tee-shirt over his head. She was the one he liked most. He could have fucked her right there and then: her big brown eyes were smiling at him the whole time. He nearly fainted as she unfastened his belt, unzipped him, went down in a crouch and pulled his jeans down his legs. He helped her all he could by lifting one foot, then the other.
"I'm awfully sorry Jason," she said, her lips pouting and asking for a deep smooch, "I have to take off your briefs too, hon."
The youth lost the power of speech as she undressed his cock. Holy fuck, he was erecting in front of these girls and he was totally nude. He had to keep his hand over it to hide what was happening.
"Arms up, out of the way," said Serena from behind.
"Hey, what ya doing?" he said. "What're you putting that round me for?" and he pulled at it with one hand and covered his cock with the other.
"We have to put you into your uniform, Jason sweetheart," said Kate, and she got her cell phone in her hand and pointed it at him.
"My uniform, yeah, but not this..." and he tried to pull it upwards, then downwards, but Serena had already fastened it down the back so that it squeezed his middle.
"But this is your uniform, hon." said Kate.
"You can fuck off 'cos I'm going," he said and he lunged across Kate and grabbed his denims. "I'm not wearing a fuckin' waspie for any job."
He stopped halfway through pulling on his tee shirt and saw her looking at her phone, with Serena looking over her shoulder. He shivered, like he'd had a bucket of water thrown over him. "What pictures. Let me see".
She let him look at her phone. It was him, in his basque. She scrolled... and again. She'd got loads of shots.
She lifted it out of reach. "They've already gone, Jason. They're on Miss Prentiss's phone now, hon. They'll be on her computer by now, all hidden away in case they're needed."
The two girls looked at him, all coy and sympathetic. "I think you'd better sit down, hon," said Kate, "and we'll explain. Come on, sweetheart, on this chair."
His heart was thumping. They had him scared. His face was a picture of fright as he took off his jeans.
"Good boy. Now listen," said Kate when he was sitting in his white basque. They were both half sitting in front of him with their panties against the edge of the dressing table. "Do you remember Simon Waterfield?"
Simon Waterfield? The creep in Upper Sixth who everybody laughed at and... Oh no, he thought. Merciful heaven. There were pictures of him on everyone's facebook...
The girls looked down at him. "Poor Simon became a laughing stock remember. He'll never get a girlfriend now," said Kate. "His photos had him in panties and little girl's socks... and a bra... and he had a stiffie, like yours."
Jason let out a wail.
For some crazy reason Jason's cock was fully erect now. "What do you want me to do?" he said. "For God's sake, don't let anyone get a photo of me like this."
Kate gave a little shake of the head. "You don't have any choice really, do you hon. You're going to work for Miss Presswell. We're going to dress you in your Pretty Boy uniform and if you don't do exactly what you're told, the internet'll be streaming with photos of you as a pervert."
He bit his lips together to stop them trembling.
"And we're in a hurry, sunshine... it's nearly opening time," said Serena. "Sit there while I roll these stockings up your legs."
Stockings! Ohhhhh! They were white, with patterns all over them. Both girls fastened the first stocking to his suspender clips, with white ribbon bows on each clip. Then they did the same on his other leg, and for some reason his prick got even more rigid.
"Smile sweetly," he heard, and Serena took another photo, or a few, of Kate fastening his legs into stockings with his penis up in front of his basque.
He was put into shoes; high heels in silver satin. They made him stand up and he managed to balance. They stuffed silky lingerie into the cups of his basque so that he had a bust. Then he nearly collapsed: the manageress came in. Oh how he wanted to disappear through the floor.
Miss Presswell looked him up and down, smiling. "He needs a pair of Frilly-Frill panties, Serena. Then a Snow Blossom blouse," she said, "and a Pansy-Pink suit. That will reveal his panty ruffles above his stockings. But for heaven's sake, hurry up. Has he been giving you trouble? Shall I send some photos to some of the girls?"
Jason felt a rising panic attack.
A scowl came over Miss Presswell's face. He got the feeling that she hated him and wanted to put those photos out no matter what. Her voice was a growl. "If he so much as hesitates from now on, tell me girls," and she disappeared.
He couldn't believe the panties he had to wear: white silk ruffles all round, especially on the back of the legs, every ruffle with an embroidered edge.
"Bye bye 'til later sweety," said Serena, talking to his penis. She kissed her fingers and patted her kiss onto its helmet before pulling his panties up and over.
"It was at this stage that Simon Waterfield decided he'd leave, Jason," said Kate. "And that wasn't a good idea, was it."
He had to stand and hold onto Serena's shoulder, to lift one high heel, and then the other, for a pink pair of satin shorts. There was pink silk inside them. They slid up his stockings, cold and slippery, and the girls laughed at the whimper of shame and excitement in his throat.
"Jason, sweetheart, you're really liking this," laughed Kate.
He had to hold his breath. He was doing his best to stop the softness from getting to him, but those little shorts... ohhhh, they were so light and... girlish. The girls eased them up over his panties, Kate in front and Serena behind, frilled out the ruffles all round, and fastened the pearly white buttons at the hips. There was a heart shaped pattern on the front in lacy frills, pushed out by his hard cock, and the shorts were so short they left lots of panty ruffles showing round his legs, with stocking tops just below.
Then they held his coat. A bolero. He had to put his arms in and it slid straight up to his neck and under his blouse collar, leaving his blouse sleeves and bow uncovered, with just one button at the front to fasten it across his bust. He felt so stupid. So helpless. He was close to crying... and they knew it was because it made him feel so lovely. So feminine.
Kate held his hand and turned him towards Serena, who took more photos... dozens of photos. It was no use trying to run away now.
They brought him in his uniform to Miss Presswell in the store and she looked him critically up and down. She smiled to see him fighting back the tears.
"He'll have to wear a uniform skirt if he's to work in my boutique," she said. "Here, put him in this."
She gave the girls a little pink skirt, like theirs but smaller, in the same satin as his shorts. They put it over his head and threaded it down over his bow and bust. It had pink shoulder straps buttoned onto the front of the waist. They threaded the straps under his bolero and over his shoulders so that the straps came together at the back and buttoned side by side onto the back of the skirt. They watched him cringe with anguish. The little girl straps were so short. The pleats of the skirt were no deeper than seven or eight inches and the skirt barely covered the top two inches of his shorts, so all his panty frills were on view.
"Turn," ordered Miss Presswell.
He couldn't stop. The girls had their hands to their mouths, astonished. Or were they laughing? Miss Presswell had one hand on her hip and "Humphed" as if he'd got nothing to cry about, and all the time his penis was as stiff as a pole in the gusset of his frilly panties.
The next thing he knew, she was telling him to lift his face and open his mouth. She had a big babies' pacifier in front of his chin.
He wailed and turned his face away with a hand over his mouth, but then thought this might not be the best thing and turned back to her. She had a look of thunder, as if she was about to go straight to her computer. He opened his mouth wide before she could.
The bulb was big and he found himself chewing on it, with a saucer of plastic in front of his nose and a ring dangling at his chin. It didn't stop him crying; he cried ten times more and pulled it out, but he could see from Kate's face that this was asking for trouble. He stopped himself from throwing it away and stood in front of the manageress, whimpering and looking pitiful.
She snatched the pacifier from him and threw it on the counter, then opened a drawer below the counter.
"Oh no, please," he blubbered. She had another pacifier, twice the size, in hot pink plastic with thick ribbons hanging off it. He knew he had to open his mouth, weeping out loud, and closed it again over a huge plastic teat that filled his mouth back to his throat. The ribbons wrapped round his head and the girls helped the manageress to put him into them, pulling them tightly round the back of his neck, finishing with the snap of a lock. The other ribbons went up onto his hair as he cried pitifully: Miss Presswell was tying them into a hot pink bow on top. The result was that he couldn't cry out loud. She had muted him. Smiling at the girls, she held him by the chin and turning his bowed head this way and that for more photographs. He was helpless.
His first job was to dress the mannequins with Serena. She was trying not to laugh but not trying very hard. The unhappy youth discovered that if he sucked hard on his pacifier, it stopped him from crying, even though the tears continued to stream down his cheeks.
They were putting white dresses on the boy mannequins. He found that it hurt in his penis, holding a satin dress: they were so feminine and they weighed a lot with all the net petticoats inside and wide satin sashes, with pearls and embroidery all over the tops. And they smelt sweet, which must have been the satin. His penis was aching in his panties.
Then they moved on to prom dresses... for boys! They had tiny buttons all the way down the back from neck to waist or further. Serena made him do the buttons up while she spread the full skirts to display them at their prettiest. They did one in aqua, one in primrose, one in burgundy and one in peach, all the while his penis felt close to blowing its load. He was just finishing the last dress when he heard a girl's voice saying "Jason! Hel-lo!"
He nearly collapsed, and when he turned round he did collapse, falling over in his heels. It was only Shania Colthorpe, the most popular girl in his economics class. He saw his world coming to an end; she would spill the lot. He was finished.
She took hold of his hand and helped Serena get him onto his feet again. "Why Jason, what are you doing dressed like this?" she said.
"Jason is working as a Pretty Boy Sissy during his holidays," said a grinning Serena. The boy wilted into bottomless misery.
His worst fear happened: Shania took out her phone. Jason shook his head and gave her the most pleading look, begging her for mercy. She took pity on him and lowered her phone.
"Oh Jason, you poor thing. You must be trembling with fear in case someone takes your picture. Oh isn't he a brave boy," she said to Serena. "But doesn't he look divine. I know, I'll just take the one shot, if you wouldn't mind standing with him, and maybe holding his hands back out of the way. That's good, so's I can get his pretty pants... his peeny sticking out like that. Oh ye-e-es... just one more... ohhhhhh, and another couple of shots. Hold him, that's right..."
She took twenty photos of him sucking on his pacifier, with white satin bows at the tops of his stockings.
"But Jason," she said, putting her phone away, "what a wonderful surprise finding you in Pretty Boy today. D'you wanna know why?"
Jason looked at her and sucked in panic.
"Brill idea," said Serena, and she hauled Jason across the boutique to where Anthony Daniels was standing with his mother, his hair all parted and combed, in a smart shirt and tie with tweed jacket and flannel trousers.
The boy's face drooped when he saw what they had done to Jason. Maybe this was a picture of things to come for himself. Shania was on Cloud Nine as she introduced the boutique sissy to her mum and explained his duties.
"He will help to undress Anthony?" said her mother in a squeak of delight, "and put him in his dresses? Oh wonderful! A sissy boy to dress him as a girl! Anthony, come here now, and stand in front of lovely sissy Jason while he undresses you."
Serena put her lips to Jason's ear and held his hand and wrist in two tight clutches. "You'd better be careful, Jason. Total cooperation with customers is essential, d'you hear? Do exactly as they say."
Jason nodded meekly, his blousey elbows resting in the sides of his pleated skirt and with white rhumba frills round his butt and his penis. He began to undo Anthony Daniels' jacket and take it off him while the boy stood there like a petrified statue. Then his tie. His hands were shaking as he undid his pants and slid them down his legs. He saw to his shoes and socks while he was down there, and saw with a fright that he had no hair on his legs. He'd been waxed. He could hardly get his fingers to work on the buttons of his shirt. What must Anthony have been thinking, being undressed by a guy in satin with a big pacifier in his mouth and a ribbon bow on his head?
"And his briefs," declared Serena, watching like a vulture.
A cold shiver went down Jason's back, but he couldn't avoid his fate. He slid his thumbs inside the waist elastic and pulled them down. They caught on his cock because he was fully erected. Jason had to lift his briefs over the knob of his customer's penis and leave it standing there as he slid his pants down his legs and off his feet.
"Not bad, Jason. Well done," said Serena, with sarcasm oozing through her voice. "Now let's see how well you can dress Anthony in his white lingerie."
"Oh mother, please reconsider," said the boy. "Do I have to go through with this? I mean, having to wear a dress like Shania?"
"We've been through this," declared his mother, taking a seat with her daughter alongside her. "Learn to look on the bright side and think how lovely you will look together as twins. Your sister Roxie will be delighted with both of you."
Jason sensed how awful the boy must have been feeling, standing there naked in the store, as Serena passed him a little white bridesmaid bra for the boy. He held it for him to put an arm in, then the other, drew his bra together at his shoulder blades so that it met, and fastened it. He had to have a garter belt, in dainty satin with lace edging. Jason hooked that at the back too. Then Serena put her hand into a sheer white stocking and rolled it up for him, so that he could thread it onto Anthony's foot and feed it up his smooth legs until he could pull each strap to the stocking top and fasten its clip. Three garters on each leg.
By the time both the boy's stockings were clipped, Jason was showing definite signs of sexual desire. He felt humiliated in his costume but was strongly aroused as well. He gathered a white slip in his hands and dropped it over Anthony's head and shoulders, so that it slid down his body and gave him a female shape, with four inches of lace round his calves.
His mother and sister must have been choosing dresses, because Miss Presswell arrived with a selection in her arms and spread them on the counter.
"He'll definitely want gloves," she announced. "If the bride is wearing satin opera gloves, her bridesmaids will have to wear them too." She opened a drawer and put long pairs of gloves on the counter. White, silver, pale pink, and pale blue, all in satin.
"Watch me, boy," she said to her new sissy assistant, and she stood beside Anthony Daniels' shoulder and put a white glove over his hand, drawing it up his forearm, then feeding in each of his fingers and finishing by pulling it tight. The boy, with a feminine, satin glove to above his elbow, buttoned at the wrist, heaved a deep sob of shame.
Miss Presswell watched Jason as he did the same with the other glove, having to hold the boy's hand in both of his, drawing the glove up until it was tight, then fastening three buttons on the inside of his wrist. She pulled it tighter up his arm and was satisfied.
"Your assistant is very good," said the boy's mother with a smile. "He looks really caring... almost affectionate."
"That's very likely," said Miss Presswell. "When wearing sissy clothes, the smooth material has a feminising effect on young men. Satin in particular. Would you like him to be really affectionate? My assistant will do everything he can to meet your wishes."
Mrs Daniels giggled something to her daughter.
Miss Presswell looked at her clients for a moment as if making sure that's what they wanted and got a nod from both of them.
A string of dribble dangled between the teat and his mouth and Serena wiped him dry with a hanky as he tried to bring the life back to his jaw. Then Miss Presswell put lipstick to his lips, shaping them all over with wax as Anthony Daniels watched in despair.
"Now, my boy," she said, " turn to Anthony and give him a soft kiss on his lips."
Suddenly the bridesmaid's blushing face turned to the side, and his mother and sister leapt off their chairs to surround him.
"You will do as you're told and share a tender kiss with the lovely sissyboy," said his mother, and his sister stood right behind him too, so that they could hold him by an arm each. "Now stand still and kiss Jason."
There was no escaping it, he would have to kiss him. Jason stepped closer, his blouse bow spreading over the bust of Anthony's slip. His lips started to tremble as they pushed closer and closer and he saw Anthony close his eyes with a furrow on his forehead. He had to put his fingers under his chin to lift his mouth. He held his breath... and their lips met... top lip to top lip and their lower lips touching too. Jason pressed downward just a little... and they were kissing.
He had never felt such excitement in his life, filling him with sweetness, and he knew it was because he was kissing a boy in white lingerie with satin elbow length gloves. He opened his lips a fraction and caught his upper lip between both of his which were trembling again. He felt Anthony's breath softly on his cheek and opened his lips again and repeated it, this time cupping the boy's bottom lip within his lips. He caught another breath and gently rippled his lips on Anthony's. He felt divinely feminine.
Then a terrible thing happened. Jason heard a moan of pleasure, or rather felt it through his lips, and it wasn't from him... it was from Anthony Daniels. The girlishness of his position was overcoming him and his moan made Jason want to reveal his own satin sweetness.
He searched with his hands and found Anthony's satin gloved arms. Holding him ever so softly, he turned his mouth and kissing across his lips, not pressing hard... just touching and puckering, opening his lips a little further to capture more of Anthony's between his. Ohhhh, it was so lovely, feeling their lips together, and then it happened: Jason's own feelings produced a whimper of sweetness in his throat. He felt the bridesmaid trying to release his arms, but no... his own blouse sleeves were being held and his mouth was being clasped by Anthony's lips. He slid his hands up the bridesmaid's slip until he could hold him to himself, his fingers feeling the fastening at the back of his bra, and the boy breathed out onto his cheek and hummed with ecstasy.
A slither of feminine satin filled the air of the boutique drawing the boys closer.
Jason felt a sizzling hiss behind him as the wide satin sash was done into a bow at the back of his waist... his penis was pressed closer to the stiffness in the front of Anthony's panties. He was fully erected. He pressed into it, slid off it, and pressed against it again.
More sizzling, and another sash was being fitted... around their necks. They were sashed together to keep them kissing, and Jason moaned with feelings of feminine love towards Anthony Daniels. He slid his arms closer, more intimately around him, his lips parted, and he kissed him with the inside of his lips, all over his mouth and sucking his lips. As their lips parted their tongues met, and they slid their tongues deliciously over each other... and Jason's penis was feeling so feminine as their penises pressed and caressed together.
He was aware of a light flashing. It was Anthony's sister taking more photos, but who cared. He wanted to kiss Anthony and gave him his tongue inside his mouth. The boy half choked, half moaned, and clasped the big satin bow in his gloves against the back of Jason's hair. It brought the sissy a swell of passion, which he voiced as it came, with moan after moan. The bridesmaid did too, and they moaned together in each other's embrace, sharing their spurting orgasms.
Jason's fingers rested on the hooks and eyes under the back of Anthony's slip for a moment as he caught his breath, waiting for his passion to subside. He felt the satin bow being undone behind his head and heard the slither of the other sash as it was unfastened from their waists. He straightened up and moved back, and his pink satin pants had a patch of creamy goo at the front.
Thank goodness Anthony wasn't wearing a satin gown. His panties were saturated and Jason felt the shame of what he had done. Kissing a boy. And enjoying it!
"Well, well," said Miss Presswell standing behind Anthony and pulling down his wet panties. "Two sissy sweethearts. Did you imagine that, Mrs Daniels?"
The boy's mother smiled. "Never, but it's so sweet!" she said.
Her brother buried his face in his hands and started to sob, but Jason kept a brave face. Whatever happened while he was kissing Anthony, it was definitely a one-off. He wouldn't be doing that again in a hurry.
In part 2: Jason models a sissy high chair and changes sissy customers' panties.