Stiletto Sisters' Sissy Training

by Suzanne High-Heels

© 2005 Suzanne High-Heels

Part 1

  

"Please Elizabeth, I don't want to go." said a young man to his wife.

"Nonsense Lee." came the very firm reply from the dominant lady. "Gemma and Victoria will take good care of you so there's no need to worry. Well get in the car Lee, I'll drop you off on my way to work." Lee got into the passenger seat while his wife walked around to the other side of the car, her stiletto heels clacking on the ground made him tremble. She got in and drove off down the street through the leafy suburb.

A couple of streets later, they stopped outside a house. A sign on the gate simply read 'Stiletto Sisters' in pink feminine writing. This was the home of Victoria and Gemma Stiletto, two notorious sissy trainers.

"All right, this is it darling," said Elizabeth. She got out of the car and stood still on the pavement noticing a lady at the window waving at her, she waved back. Lee slowly and sheepishly got out of the car. "Come on Lee, hurry up" she snapped. She took him by the arm and led him up the driveway to the house, through a well-kept and very nice looking garden. A lady opened the door as soon as they reached it.

"Elizabeth darling, how are you," said the lady,

"Hello Gemma I'm fine thank you." replied Elizabeth, and the two ladies then kissed each other on the cheek.

"This must be Lee, isn't he adorable, come in." said Gemma.

Gemma led them through into the living room, with Elizabeth almost dragging Lee along. Elizabeth sat on the sofa and told Lee to sit on the carpet. Gemma called upstairs

"Victoria darling, Elizabeth is here."

"Be right there" came the reply. Moments later Victoria walked into the room carrying a photograph album. The ladies sat talking between themselves for a few minutes until Elizabeth left for work.

"Well I have to be leaving for the board meeting ladies, I hope my husband will be very pretty when I get back." she said, patting him on the head.

"Oh he will be" said Victoria, grinning at Lee. "Just leave it to us, we'll have him turned into your little girlie toy by the time you get back." replied Gemma. As the ladies left the room to see Elizabeth off, Lee stayed sat on the carpet too nervous to move. Elizabeth headed off in her car, and then he heard Gemma and Victoria giggling as they walked back into the house. This was it, he thought, those evil women were going to have their wicked way.

Gemma and Victoria walked back into the room, sat at opposite ends of the couch and invited Lee to sit in between them.

"Surely you're not afraid of us Lee! We only want to make you look nice and pretty," teased Victoria. "I have a little something here that you'll like." Victoria picked up the photograph album from the coffee table.

"See dear, these are all the men we have feminized." Gemma began to point to some pictures. "Here's our dentist dressed up like a teenage tart, the local vicar dressed as Minnie Mouse." Turning the page Victoria carried on:

"That's the manager of the shopping mall dressed as a schoolgirl. Doesn't he look cute in that gymslip?"

"Here's our triumph though, Lee" interrupted Gemma "It's our awful mayor dressed as Alice in wonderland."

"You see Lee, a lot of men come here to look pretty and feel girlie, and you're very lucky to have a wife like Elizabeth who understands your need to be frilly."

"But I don't wa…"

"Ah, ah, don't say anything." said Gemma stopping Lee from talking. "Just wait Lee, soon you'll be all girlie in a skirt and blouse and a nice pair of high heeled shoes.

"But first we need to get you milked so that you can be properly feminine." Gemma then left the room and came back with a large white box that said 'sissy milker' on the side in small pink letters. "Now remove ALL of your clothes Lee dear. Let's get rid of all that nasty male cream." With some persuasion from Gemma, he reluctantly did as he was told. There he was, standing in the ladies living room without any clothes on. "Now we are getting excited aren't we" said Gemma, pointing to his hardening penis. Meanwhile Victoria started unpacking the box. First out was a large pink PVC bag. She laid it out on the floor and undid the zip down the middle. She told Lee to climb inside.

"Well we don't want you staining the carpet darling." He got inside without complaining.

Next out of the box was a diaper with a bunny motif.

"Let me put this on you" barked Gemma. Gemma put the diaper on him making certain it was properly in place. Victoria then did up the bag's zip with Lee lying inside and tightened it up with the string at the top. Victoria then brought out the last item, it appeared to be a large pink rabbits head, made of PVC. It had eyes, bunny ears, a full rabbits face, and was, Gemma told him, to wear over his head. It was stuffed and very well padded. The mouth could be opened by undoing a few poppers, leaving some room inside above the wearer's mouth and nose. "Why that's so you can breathe sweetie." Gemma said wryly. "Sit up while I put it over your head." She held it above his head then slowly lowered it onto him; it was so big it nearly came down to his shoulders. The smell of PVC surrounded him and was actually quite pleasurable. She then told him to lie back down. The two ladies then left the room. He must have presented the most bizarre sight, he thought, a pink bag with a rabbit's head laying in the middle of the carpet.

A few minutes later they returned.

"Sorry to keep you waiting Lee. We have all we need now," said Gemma. Victoria opened up the compartment at the mouth and began stuffing her panties in there, pushing them down onto his face. When she'd finished Gemma did the same with her own panties. With Gemma and Victoria's panties lying on his face, Victoria did the poppers back up to seal in their feminine smell.

"That's it darling, breathe deeply." instructed Victoria "breathe in the smell of our lovely panties." The two ladies laughed at him making small wriggling movements in the bag as he tried to resist. But the more he moved, the deeper he breathed and the more feminized panty air he breathed in. He shook around in the bag for a few more seconds but soon settled down. Every breathe he made under the panties, inside the mask could be heard.

Victoria and Gemma both listened intently for his breathing to grow deeper. After just a few minutes he began to moan.

"Oh Victoria, I think our pink bunny is about to cream herself." laughed Gemma. MMMM, MMMMM, MMMMNNNNN. He moaned as his milk poured into his diaper. Victoria waited a few moments before opening up the poppers of the mask. Removing all of the panties from his face she asked him if he'd had a 'girlie little thrill'.

"Yes…. Mistress" came the rather weak reply.

"We'll let you have a rest for a few minutes darling while we busy ourselves upstairs. Don't you dare try to get away." said Gemma. The ladies went away for about ten minutes leaving him lying on the floor inside the weird costume.

Eventually they came back. Victoria knelt down to talk to him.

"Elizabeth tells us you like stockings, is that true?" she asked with a wicked look. But before he could answer she pushed in through the mouth several pairs of her own stockings. Fixing the poppers back up she told him they wanted his diaper to receive a second helping.

"This will give him a jump start," said Gemma rubbing his penis through the diaper and bag with her shoe. Again he started to shake as he breathed in the 'girls foot smell' of the stockings. As a stockings fetishist he couldn't help himself. He breathed deeply which quickly led to him squirting his cream again. "I think we're done Victoria dear," said Gemma as Lee stopped moaning. Removing all the stockings and the overhead mask, Lee was finally freed from his girlie confinement. Still in the pink bag they both helped carry him upstairs to the bathroom.

They removed him from the pink bag and made him take off the diaper

"Leave the diaper in the bag" said Gemma. Victoria zipped it up and took it down to the kitchen. Gemma gave him a special lotion to remove all of his body hair. She told him to rub it onto himself from the neck down, wait a couple of minutes, then get into the bath. They had filled it up earlier while getting the stockings. After the bath, Gemma rubbed in a body lotion that made his skin silky smooth. He was then handed a pair of silky pink panties and a pink dressing gown with a pair of white fluffy slippers, which had four-inch heels. He rocked uneasily in the slippers. "First time wearing high heels?" asked Gemma. He nodded. "Don't worry," replied Gemma, "soon you'll have lots of experience wearing heels".

She then led him by the hand out of the bathroom, across the landing, and into one of the bedrooms. This was the dressing up room. The room was decorated like a feminine girl's room in bright pink with cuddly toys and pretty dolls everywhere. They sat him down at the vanity mirror and began to apply make up. Foundation, blusher, eyeliner, eye shadow and red lipstick. When they had finished, he certainly looked very feminine.

"Now we're at what I know will be your favourite bit." taunted Gemma. He shivered at the thought of what they would dress him in, as Gemma and Victoria busied themselves in one of the wardrobes. Giggling all the time, they were like two little girls forcibly putting their younger brother in a dress and girl's shoes.

"Look at all the lovely clothes Lee," said Victoria. "You could be a ballerina, a French maid, schoolgirl, a bunny girl, even a baby girl." Gemma continued in the other wardrobe

"Or how about these Lee, a bridesmaid dress, a cheerleader's uniform. But for you, how about we start you off in a nice satin blouse?" Lee just sat there quietly.

"Take that dressing gown and those slippers off. You can keep those panties on. Now for a bra." said Gemma reaching into a draw. "Here you are, Lee, a nice lacy bra!" She passed the bra to Victoria who in turn put it on Lee.

"Now for some breast forms. These should fit that bra nicely." Victoria said as she slipped one into each cup.

"Here. He can wear this garter belt," said Gemma. Next came the stockings. Gemma showed him a pair of sheer black stockings.

"Do you like them darling? Put your foot on my lap and I'll put them on you." said Victoria. He quickly did as he was told and Gemma sheathed his feet and legs in the stockings. The feelings they made as she slid them up his smooth legs were sensational.

"You liked that didn't you?" laughed Gemma as she fixed his stockings in place. "Now stand up and let's get you dressed."

Victoria brought out of the wardrobe a pink satin blouse, which they proceeded to encase him in. Next came a pink skirt. They wrapped it around his waist then began to give him comments about how pretty he looked. Next came the choice of shoes. They had just about every type of female shoe imaginable from sexy stiletto heels to innocent Mary Janes.

"What shoes should we put him in Gemma?" asked Victoria. Those pink high heels of mine would be perfect. I'll just go get them." replied Gemma. Gemma ran across to her own bedroom while Victoria showed Lee some of the shoes in the wardrobe.

"Look at these Lee, six inch heels. They're really hard to walk in! Or what about these?" she said showing him some very large outsized high heeled shoes.

"What are they …" he asked.

"They're for dressing up as a little girl when we want to give you the 'trying on mummy's shoes' look."

"I've found them!" shouted Gemma re-entering the room. She pushed him back on the bed and slipped her pink pumps onto his feet. She pulled him back up and sat him back in front of the vanity mirror. A long black wig was the finishing touch. He looked in the mirror stunned into silence at the beautiful woman he had become. "Do you like it Lee, or should I say Leanne?" He simply nodded and weakly said,

"yes" in a small gasp.

The two women took him back downstairs where they talked him through how to walk in high heels and how to swish his skirt and look sexy. Next, Victoria instructed him to go into the kitchen and wash the diaper he had soaked earlier. On entering the kitchen he found the pink bag on the floor with the diaper inside. He picked them up and began to wash them in the sink. He took his high heels off as they were beginning to hurt. He put the shoes together under the table. He had just finished washing the diaper when Gemma walked into the kitchen.

"Where are your shoes?" she blurted out.

"Under the table Mistress."

"You took them off, why?"

"They were hurting." he replied shyly.

"That is not good enough, put your shoes back on." He slipped his feet back into the supple leather shoes and Gemma dragged him out of the kitchen and into another room upstairs.

She tied his hands to a pair of red furry handcuffs hanging from the ceiling and his skirt and panties were removed. He was left standing with his bottom exposed and his panties around his ankles.

"Since you did something shoe related I'll start you off with the gym shoe." She whacked his behind with the gym shoe several times then produced a smacking paddle she called the 'Sissy Spanker'. The handle and the back were covered in pink fur and the back also had a red love heart. Victoria ran into the room looking excited and stood in front of him. Gemma made him kiss the paddle first, then she spanked him hard with it stopping occasionally to rub his bottom with the paddle. When Gemma finally stopped Victoria grabbed his face and snogged him, allowing her tongue to fully explore his mouth. He was then spanked and snogged three more times.

When Gemma and Victoria had finished their torment, they sat him down in the living room on the pink chair with his bottom still hurting. The two ladies sat on the sofa. They questioned him about how feminine he wanted to be and the sorts of things he would like to wear. He reluctantly gave them the answers they wanted to hear.

"Good Leanne, I'm glad to hear it.," said Gemma. "Now come over here and take my shoes off." He did as he was told and gently took off Gemma's shiny black high-heeled shoes and placed them carefully at the side of the sofa. "Lie down Leanne and I'll reward you." He did and Gemma placed her stockinged feet on his face. He squirmed underneath Gemma's feet for what seemed like hours when he heard a knock at the door.

Victoria answered it and in came Elizabeth. She glanced down at Lee underneath Gemma's feet and smiled.

"Darlings, he looks wonderful and so submissive." she said sitting down.

"Well, we enjoy the work you bring us Elizabeth," laughed Victoria. "How was the meeting today Elizabeth?"

"Very good. Just a couple of useless males. Maybe another job for you ladies some day." The three ladies laughed. Lee tried to say something but was muffled by Gemma's feet. "What was that precious?" Gemma asked removing her feet.

"Can we go home please Elizabeth?"

"No darling." Elizabeth replied. "My friends and I wish to make you a little younger yet." He saw the ladies smiling at each other and dreaded to think how he might look next.

Back upstairs in the dressing up room, Lee was once again naked. The ladies had decided this time to dress him up as a little girl. Victoria started by taking a pair of soft white panties from the drawer and instructing him to put them on. Gemma and Elizabeth watched intently while sitting on the bed. Next came a petticoat, followed by a pair of frilly white ankle socks. Gemma then went over to the wardrobe and picked out a dress. The dress was white and decorated with pink bows and pink lace and had big puffy sleeves. Gemma helped him into the dress, fastening all the buttons and tying the pink sash at the back into a pretty bow. Sitting him down and lifting his legs up, she then put a pair of shiny black Mary Jane shoes on his feet and buckled the straps. On his head she put a long blonde wig and tied a large pink bow into it. The finishing touch was a pair of lacy white gloves. She tied them into place with pink satin bows.

"My my, you really are my little princess now." said Elizabeth as she admired Gemma's handiwork. Victoria pointed Lee toward the mirror. He saw the frilly little girl he had become looking back at him. The skirt and blouse were humiliating enough, but a puffy white little girls dress was too much and he began to cry.

"There, there little Leanne. Don't cry! Here, hug your teddy bear." said Victoria placing a pink bear on his lap.

"Hug your teddy," snapped Elizabeth. He wanted to throw it away but he dare not disobey his wife. So he did as he was told while Gemma took a photograph of their latest victim for their album. His new life as their sissy plaything had only just begun.

  

  

  

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