WHAT HAPPENS WHEN LESLEY WEARS A DRESS?
from Prim

"What is it, Mom, you're not going to have another go at me about giving Harry James the green light, are you? I told you No last week and that's final." Lisa could pout for England if she thought it would save her from another lecture.

Clara pushed the latte she'd made for her daughter across the table and lifted her own to her lips while shaking her head in reassurance. "To be honest, darling, it's not about you. Not directly anyway."

Lisa frowned, picked up her coffee and gave her mother a guarded look from beneath her blond hair.

"You know your cousin Lesley?"

"Yeah?"

"Who always keeps himself to himself, even more so now that you've all left college?"

"What about him?"

"I've been talking to your Aunt Barbara about him. She's not exactly worried but - we had a long chat over a coffee. I think you might be interested in hearing what she was telling me."

Lisa shifted her leg from under her ass and sat more comfortably on her kitchen stool. "I like Lesley," she said. "He never does anyone any harm and he - well, he looks up to me. If I told him to jump under a bus I think he would."

Clara lifted her brows as if to say that fitted in perfectly with what she was about to say. "His mother was telling me that he's got a definite gender thing, to do with her clothes."

"Oh for God's sake, mother: all boys have. So what?"

Clara wasn't expecting her nephew's habits to be passed off as normal. "What if I told you that Lesley asks his Mom if he can spread one of her slips across his knees - while he looks through her fashion catalogues. Not once or twice, Lisa: that's every evening, until he goes to bed."

"Whoa. Right. So he's a cross-dresser. But where do I come in, indirectly?"

"I'm coming to that. She sometimes puts him into a skirt in the house, which makes him star-struck into a world of dreams, in which he will say things like: "pretty dresses" or "stockings and a c-c-corset with suspenders, getting all emotional about it."

Lisa drank her coffee. "Does he just do this in front of his Mom, no-one else?"

"Up to now, yes."

Lisa looked more interested.

"Barbara and me talked about - well, what if he came to see us, seeing how we have different clothes in our closets? We could share one or two juicy fashion magazines with him."

"Mom, you creepy witch. Are you talking about seducing the poor thing?"

"Oh for crying out, of course not! I'm thinking of giving Barbara a break." She took two or three more sips at her latte. "And also of what fun it will be watching him getting excited, in our slips and dresses."

"Hmmmmm." Lisa could have been criticising her Mom, or beginning to see the advantages of having a star-struck, or petticoat-struck cousin to play with. "So what did Aunt Barbara say? Is she going to bring him round so that he can stand in front of our open closets, and show him our drawers of lingerie?"

Her mother pursed her lips with the pleasure of having a little plan already hatched. "She's sending him round at 11 o'clock. He's going to help his Aunt sort out some clothes for the second-hand shop."

Lisa choked on her coffee, nearly down the front of her tee-shirt. "Mother dearest, you are a crafty one. I do believe you're going to enjoy today in a - well, a really sexy way." She giggled, warming quickly to her mother's plan.

"Thank you dear. But to make sure we have a reasonable chance of making it work, I want you to stay out of the way to start with, up in your room for instance. We don't want to spook our young sissy. Then you can bring your own 'crafty' brand into play when Lesley is hooked. In fact that's part of the plan: if he allows himself to be dressed in front of more women than just his Auntie Clara, we've got a better chance of keeping him in dresses and petticoats when we have more girls in the house."

Lisa laughed. "Now you're really talking, Mom. Britney and Zara can come round to see him. Oh my God!"

Mother and daughter scurried upstairs to make their preparations for the life-changing step they would take come 11 o'clock. When the innocent 18-year-old arrived at his Auntie Clara's, he had a dim idea of what lay ahead for him: "Mom says you want me to help you take some of your old clothes round to the second-hand shop," he volunteered. This would be a matter, he thought, of picking up two bags of old stuff and walking down to the shops.

"Not the second-hand shop, darling," corrected his Aunt; Lisa was nowhere to be seen as she led him up the stairs. "I'm picking some clothes for the church fair. That means they have to be smart and in very good condition." She closed the bedroom door behind them and made for the first of her wardrobes.

Lesley couldn't help but noticing how neatly dressed Auntie Clara was, in one of her crisp bow blouses and a red skirt. He always thought she dressed smartly and loved looking at her as she sat or watching her moving around in her clothes. Right now he felt bewitched by the silent, softly perfumed air in her bedroom, where the drapes, the bed, the dressing table and one or two dresses on hangers made this room seem like he was in the holiest, most feminine part of the village church. It made him draw his breath with reverence, and a weight of female privilege made him feel most grateful and obedient to his Aunt. She opened her wardrobe and instantly added to his helplessness.

One of her preparations was to ensure that only her smartest dresses, blouses and skirts were left hanging in her closets. She took out a cocktail dress in apricot taffeta, filled out with integrated petticoats, and passed it to her nephew on its pink satin hanger.

"Just hold that for me, pet. Let me see - " and her fingers spread its three-quarter sleeves and the voluminous spread or its Fifties skirt. "I'm not sure about that one, honey. What if you sit in the armchair and I can pass you one dress after another, to spread out over your knees."

Lesley had no idea where the armchair was or whether he sat on it or not: he just found himself sitting under Auntie Clara's cocktail dress, with a lilac sheath dress in duchess satin laid across it, then a dress with a white bodice and oceans of organza skirts bursting from the waist and filling his nostrils with the sweetest scent of perfumed femininity. His Auntie slid open a drawer in her dresser and lifted out a long, gleaming girdle in pink satin with four suspenders dangling from its bottom edge. A wail of desire somehow slipped out of his throat and sounded awkwardly loud in the quiet of her bedroom.

She heard it, and he couldn't take it back. She turned to him where he sat under his spread of dresses and skirts, with a white nylon blouse spreading its pretty ruffles right under his nose, and showed him the panelled detail of her girdle. She was not a large woman, so the girdle was really quite narrow - and so utterly feminine. "Do you like it, pet? Isn't it pretty?"

"Y-Y-Yes Auntie."

She turned it this way and that, then unzipped it from top to bottom and parted it to show him the satinized lining before holding it closed again for him to enjoy its shape. "Your Mom told me you liked her clothes," she said. "That's why she suggested you might like to help me sort through my clothes, and help me to choose which ones to give away."

The blush on her nephew's cheeks was all the more scarlet for the whiteness of the blouse frills in front of his chin. He was heaped with so many of her clothes so far that there was no escape for him from their powerful influence.

"If you want to put on one or two of my things, Lesley darling - you may." She let this shattering news sink in for a trembling moment. "I'll help you, if you like." His scarlet turned to crimson - but there was no splutter of objections from him. Instead his Auntie lifted the garments from his knees and spread them for the sake of speed on the bed. She was ready with her opened girdle as Lesley obligingly, and rather eagerly, removed all his clothing, finding himself standing in his birthday suit in front of his Auntie Clara.

How exquisite it was to be cared for, and dressed, by her elegant hands and fingers. It was almost as if she held her breath as she wrapped the glossy pink girdle round him, so that it extended from on his ribs down to within inches of his knees. It was so TIGHT as it squeezed inwards round his bottom cheeks. He watched those fingers as they fitted together the base of the zip, and slowly slid it up the front of his left leg and thigh to well above his waist. "I'm going to put you into a pair of my nylons, pet," she said, her voice a husky whisper. In no time she was unrolling one, then a second, stocking up his legs and securing them inside their suspender clips.

"There, isn't that nice?" she said, taking his hands and lifting him to his feet. She had a pair of boudoir mules to slip on over his stockings, with a pink pompom on each instep. It was as he stood at the closet mirror, admiring his wonderful feelings, that everything sank to the floor - for the bedroom door opened, and he was instantly seen by his cousin Lisa.

Lesley's hands covered his face. He thought he was safe in the private secrecy of him and his Auntie. He didn't want to look. He didn't want to hear what she would say in girls' scorn and contempt. The first he knew was the touch of her hand on his bare arm, and her words in his ear as she looked at his pink reflection over his shoulder.

"I'll bet you're feeling wonderful, in Mom's girdle and stockings." There was a pregnant pause where everyone felt their feelings: the women knowing what a flood of feelings were churning underneath that satin girdle; Lesley as it were nakedly exposed to them in his longing to wear the contents of his Auntie's corsetry drawer. Lisa's hands slipped down from his arms to the glossy flanks of his girdle, and then to the zipper, which she drew down, down, and off as the girdle parted.

"I've got an idea, Lesley sweetheart - which I think you might really like." As the girdle opened, still clipped to its stockings, his cock was stiffened, pointing at itself in the mirror glass. "D'you know what I found the other day when I was going through the spare closet in the junk room?"

The boy's heartbeats knew it was probably something he would really like.

"An old party dress I wore, years ago, before going to college - and it's in pink satin with its own petticoats to fill it out into a girlish spread around you. Do you want me to get it for you?"

Lesley was overwhelmed. "Oh yes please!" Because this was Lisa being so nice to him, joining her mother in making him welcome to wear feminine things in their house. "I-I'd like that."

"Of course you would," declared his Auntie as Lisa disappeared and she undid his suspenders to take everything off him again. His poor heart was thumping almost visibly on the walls of his chest as his cousin returned, a wide pink dress spreading beneath its hanger and a selection of lingerie in her other arm, with a pair of pink girly shoes in her hand. His cock may have been stiff before, but now, as his Auntie and cousin stood on either side of him and dressed him in a pair of panties and frilly little socks, it moved to standing fully upright, so firm and so STIFF. He had to lift his arms over his head to meet the armholes of Lisa's dress in their puffed sleeves of pink satin, and the white petticoat floated down and around his naked body, wrapping him coldly in his lovely cousin's lovely petticoat dress. He let out an uncontrollable moan, which led to Clara pulling him into her blouse in a warm maternal hug. He knew she understood him, and so did Lisa! He was blessed with perfect happiness as they took him by a hand each and led him from the bedroom, down the stairs and into the sitting room.

"Sit here, Lesley," cooed Clara, as she drew the back of his dress and petticoats clear of his ass to prevent it getting crushed underneath him. "I think it might be best, while you're sitting in your dress for us, if I just slip this ribbon round your hands at the back; then you can feel more like we're looking after you, and taking care of you."

This was alarming to the boy, but he was safe in Auntie's hands as he felt her fingers folding the length of ribbon round and round his wrists and doing it into a bow. He was helpless now, completely in their hands, and it felt so lovely. Blinded by his delicious feelings, her nephew didn't get as far as wondering why his cousin's 'old' dress was uncreased, and how in fact it was freshly ironed, and so crisp and pink and girlish. His cousin had changed into a rustling plum coloured skirt and scoop necked white blouse.

"Let me spread your dress nicely over your legs, Lesley," she said to him, her voice as soft and encouraging as her mother's. "And look what else I found in the spare wardrobe: I wore it at a school pageant when I was being a Lolita girl."

From behind her she brought out a stiffened Easter bonnet, filled with starched and polished white linen so that it's pink bowl spread in a wide shape to frame the wearer's face. That wearer was soon her cousin as she held it by the front edges and drew it round the back of his hair, so that she could gather the ribbons into a neat bow under his chin. He held his face forward to help her put it on for him, and as the two females fluffed and plucked and arranged his dress all round him, he sank into a semi-awake, girlish mode so that he only half heard what they were saying.

"This is much better than looking at Mom's shopping catalogues, honey." "What cute socks and shoes, Lesley. You are such a girl." "We can put some make-up on in Lisa's bedroom for you if you like." "And I could spread one of my girls' Sweetie-Kiss sani-pads inside your panty to help you feel more like me."

Lesley sank back in the settee, looking oh so gratefully from one of his divine female helpers to the other, then drinking in the beautiful girlishness of his dress. His Auntie held his hand and stroked the back of it in her fingers, all smiles, all soft words, as Lisa disappeared for a minute before returning with a large pink appliance which she set on its wheels on the carpet.

"This will make your dressing so much nicer for you, Lesley," she told him, not exactly smiling, more like taking him under her loving wing. "You'll feel awesomely girlish like you've never imagined. It's our feminization hormone machine. I use it when I'm going out to party, like when I want to be more attractive to the guys by being more of a girl than the girls around me." She had the tube in one hand and the pursed ending in the other.

Auntie Clara in the meantime had the front of his dress opened up almost to his throat, and spread apart to give Lisa full access to his panties.

"This is its suction sleeve," said his cousin, showing him the end away from the tube: a glimpse of padded cushions of white satin disappeared into its interior. "It fits over your stiff popsy, honey, even though it's still dressed inside the gusset of your panty - like this - " and the sheath pushed down onto his stiffened erection, pressing down, sliding inch by tight inch, until it slid the final distance and his knob nestled into its innermost cup. He was connected to the machine, the pink tube joining its vulva onto his own reaching cock.

Lisa held the controller, dotting her finger from key to key and icon to icon. His cock was already thrilled to be held by this female machine, then it seized his member with the shock of a buzz.

He jolted upright on the settee, into his Auntie's arms for support and safety. The hum of feminizing settled down into barely a tickle in the silence that followed, but he knew the woman shaped appliance was doing things to him because he was feeling the pleasure of his panties around his cock, of his socks and his Mary Jayne shoes, and his petticoat and dress. He was fully dressed as a girl - all that he wanted - all that he could handle as the sheath held him to the machine and controlled his whole sex.

"Mmm," hummed Auntie Clara, "isn't it nice, being femmed: are you happy with that, sweetie, hmm? We thought so."

They sat beside him again, each of them holding and stroking one of his hands, until Auntie Clara picked up her phone and tapped a number.

"Hi Barbara. Well, you were right. Lesley is loving helping us with sorting through some clothes. He's wearing one of Lisa's nice dresses for us." Lesley panted with worry. What would his Mom say? But the next thing, Auntie Clara was turning the phone to him. "Here's your Mom, pet," she said. "She wants a word with you."

He could feel his heartbeats banging in his chest as she held her phone at his cheek and he heard what his Mom had to say. "Hello darling. Tell me more about what you're wearing."

His mind tried to process whether she was mad at him. He put a brave face on it. "Lisa chose a dress for me, Mom. It's lovely and pink - and it spreads out round me, making me like a girl. I'm wearing puffed sleeves, Mom."

"Does it feel nice being a girl for Lisa?"

"Oh yes, I want to be a girl for Lisa."

"Is she going to put you into some of her panties, and maybe a bra and slip?"

Even as his Mom was talking to him he saw Lisa keying variations into her controller and a new tinge of sweetness swelled through his sheath and filled his cock with the most girlish pinkness he had ever felt. Before he got to answer, his Auntie squeezed his arm and said:

"Darling, ask your mother if you can stay over till Sunday."

The boy's Mom had heard. "Yes darling," she laughed, "of course you can. It's a very good thing that you share your happy love of our dresses and clothes with Auntie Clara and Lisa."

His Auntie took the phone from his limp fingers as pulses of pleasure filled his cock and the pink feminzing machine seemed to fill him with more and more pleasure.

"He's being such a good girl for us, Barbara, so we'll make sure he can wear some other lovely clothes of ours all evening, and feel very sweet and girlish between us."

It didn't escape his notice, partly because she was taking photos of him, that Lisa too was on her phone to her friends. "This is my cousin: come on over. Mom says we can have a ball." It was when she set her phone aside and took up the pink controller again that Lesley turned to her, his face appealing to her to fulfil his wish, and said:

"Please Lisa, put me into your panties for when the girls are here - with a sweetie-kiss sani-pad to help my clitoris feel just as girly as yours."

His cousin dabbed another icon, and Lesley had never felt so deeply girly into the very roots of his cock.
***
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