Stiletto Sisters’ Sissy Training Part 2

By Suzanne High-Heels

Copyright © 2006 Suzanne High-Heels.

Sissy husband Lee was sitting in his playpen playing with his dolls, he was dressed in a gingham dress, white socks, black Mary Jane shoes and a blonde wig with pigtails, blissfully unaware of what his wife was planning for him. His wife Elizabeth, a high-powered executive businesswoman, was talking on the phone to her friend Victoria Stiletto, who with her sister Gemma, specialise in turning men into submissive sissies for the pleasure of other ladies.

“I love the job you ladies did on him last month, he’s such a sweetie.” said Elizabeth.

“Not giving you any problems is he Elizabeth dear?” asked Victoria.

“He’s an angel,” replied Elizabeth, “but I would like his training taken to a higher level.”

“Say no more darling,” said Victoria. “I think I know what you mean, maid training, pleasing you, that sort of thing.”

“Oh yes, I mean he’s cute but he’s useless for anything practical, could you help?”

“Of course dear, we’ll put him on the advanced sissy training regime, it will take a couple of weeks however, but it will be worth it.”

“Would it be possible to have him done before Christmas? I need someone to serve drinks at the office party.”

“Ohh, tricky, but I think we can just make that, bring him over today at about five, we’ve got an adult little girl kindergarten in today, but there’s no reason why he can’t join in near the end.” “Yes, I think I can hear one screaming in the background” said Elizabeth.

“What’s Gemma doing to him?”

“Oh she’s spanking one of them, I think for spurting his cream in his knickers.”

“I see,” laughed Elizabeth “We really can’t have that, all right, I’ll bring him to your house at about 5.”

“OK dear and bring some of your own clothes that turns him on, panties, stockings, that sort of thing.”

“All right, I have the very thing. You know, he’ll be really pleased to see you both again.” The two ladies laughed and said goodbye. Elizabeth immediately headed into the living room. Hearing the approaching tapping sound of Elizabeth’s high heels on the wooden hallway floor Lee began to hug his teddy bear, the tapping sound was then muffled by the living room carpet until it stopped. He turned around to see Elizabeth’s exquisite shoes and stockings, looking up he saw his wife looking down at him. “Hello Leanne dear, having fun?” she asked.

“Yes…mistress Elizabeth.” he replied nervously in a girlish voice.

“Good, you’re a lucky girl aren’t you? Do you know why you’re so lucky?” she asked patting him on the head.

“No mistress.” he replied shaking his head.

“Because you get to have even more fun staying with Gemma and Victoria for two weeks.” As soon as he heard the names Gemma and Victoria he remembered the embarrassment and the humiliations he was made to endure the last time he was there. He felt terrified, his jaw hung open and he hugged his puffy white teddy bear even harder. “It’s not that bad dear.” she said while walking out of the room “They’ll take good care of you like they did last time.” said Elizabeth. He shuddered again.

Later on, he was ordered out of his playpen and to the front door. Elizabeth helped him into his fluffy pink coat before dragging him out of the house to the car. Two bemused passers by looked on at what appeared to be a heavily feminised man dressed as a little girl being reluctantly buckled into the back seat of a car by a well dressed lady. A short drive through the tranquil suburbs followed. At the house, Gemma answered the door.

“Hello Dear.” She smiled at Elizabeth,

“Hello Gemma” replied Elizabeth

“Hello Leanne sweetie.” she said to Lee while pinching his left cheek. His heart pounded as he felt both fear and excitement.

“I’m sorry I can’t stay Gemma, I have some paperwork to finish at the office.”

“That’s all right Elizabeth, we’ll have Leanne nicely trained in two weeks time.” With that, Elizabeth handed something in a bag to Gemma, then left, he was left entirely at Gemma’s mercy. “Now then, shall we get started?” she said, taking his arm and dragging him to the bathroom. She gave him a quick feminine scented bath, then he was taken along the landing completely naked to the dressing room. There he was told to put back on his pink panties and the blonde wig. Mistress Gemma applied some make up to his face, then came his outfit for the adult little girl kindergarten. The theme this week was Minnie mouse, so he was dressed in a pair of black tights, a red polka dot dress, yellow high heeled shoes with a red bow on the front, white feminine gloves and a headband with a pink bow and mouse ears. “There, don’t you look cute sweetie?” teased Gemma. He gazed at his new appearance in the mirror, he was stunned, he looked like a little girl in her Halloween costume going out trick or treating. Gemma laughed at his expression. “Don’t worry dear, all the other girls are dressed the same way.” She guided him downstairs to the living room, Victoria was sat on the sofa in front of six heavily feminised men. Gemma sat him down on the carpet with the other six ‘girls’ who were also dressed as Minnie mouse. Victoria was reading a story to the girls called ‘The Forbidden Panty draw’. The story was about a young teenage boy who was caught sniffing his auntie’s panties from her draw. As punishment, she magically turned him into a pair of lacy pink panties, wore him for two days straight then sold him to a panties fetishist. When the story came to an end the girls were told to all line up on one side of the settee, Victoria and Gemma both sat at different ends. Victoria asked for the first girl to come over and sit on her knee, as she did Victoria immediately began to feverishly kiss her. After about two minutes she asked for the next girl while the first was passed onto Gemma, she laid the girl across her knee, moved the polka dot dress up, pulled her knickers to her ankles and began to spank her. When it came to Lee’s turn Victoria gently took his hand and sat him down on her lap, wrapped her arms around him and began to snog him. Her hot wet tongue slipped through his lips exploring every inch of his mouth. Her lips pressed harder as her tongue lapped even harder against his own tongue. When his time was up, he was gently pushed off Victoria’s lap and fiercely pulled over to Gemma. After laying him over her knee and slipping his panties down she began to roughly spank him. Hit after hit followed as Gemma’s hand hit his bottom until it was throbbing. After she had finished she pushed him off into the corner with the other sissies who had been seen to. When the last girl had been done to they where taken upstairs by Gemma to undress, remove their make up and get back into their own clothes.

“You wait in here with me Leanne.” said Victoria, sitting him down on the floor. “While we’re waiting you can lick my shoes, I know you like that.” She thrust her foot in his face, he steadily started to lick the smooth patent black surface of Victoria’s shoe. Victoria smiled in appreciation as he diligently worshipped her shoes. A little while later he heard voices coming down the stairs, the men were all back in their own clothes.

“Remember girls.” called Gemma from the top of the stairs. “I will charge all your credit cards tomorrow, next week it will be an Alice in Wonderland theme.” A small gasp came from the men at the thought of being dressed as Alice. They all left and Gemma entered the room, by now Lee had both of Victoria’s high heels in his mouth, she playfully pushed them in and out of his mouth as he knelt down squirming. “No time for fun and games now dear.” said Gemma. “We have to get Leanne ready.”

“Oh yes, your going to enjoy this Leanne.” said Victoria as she pulled the heels of her shoes from his mouth. They led him out of the living room and down the stairs to the basement.

Gemma led the way down the stairs and guided him to the middle of the room. Victoria switched the light on, around him was a room furnished with many devices and objects used for weird and erotic feminisation. Many cupboards and storage draws laid up against the walls. A furry pink table stood in the centre of the room. It had restraints made from pink leather at each end of the table to tie its victims to it. In one corner of the room was the smothering chair. The sissy would be forced inside the chair and their face would be presented to their mistress through a hole either in the seat of the chair or in the footstool. So the sissy would be smothered by either the mistress’s bottom or her feet. The walls were painted in dark pink, the carpet was a pastel pink and very thick and fluffy.

“Your treatment is over here Leanne.” said Gemma pointing out a large pink object in a corner. It came up to about waist height and made of a thick pink rubber. This was what Gemma and Victoria described as the sissy womb, and Leanne was to be put inside it. At the front, it was made to closely resemble the female genitals and was used as an entrance for the victim. A small tube was placed at the back of the womb to allow the sissy inside to breath, a much larger tube, about the width of a vacuum cleaner attachment, emerged from the centre on top of the womb which ran over to a table standing only a short distance away, the tube was connected to an air tight bag. Another tube connected the bag to a gas cylinder. The cylinder had a large pink bow around it and was marked ’Oxygen’. The two sisters got busy, first he was completely stripped, then shown what was inside the airtight bag on the table. Inside was a pair of glossy black high-heeled shoes with a pair of stockings. They asked him I he recognised them. Confused he answered ‘no’.

“They’re Elizabeth’s cutie, she brought them over with you earlier. You get excited every time you smell them don’t you. Next, the sisters moved him onto a PVC mat. Victoria kissed him sweetly on the lips to make his penis hard, then Gemma put a masturbatory device onto his erection . It was soft, round in shape and about the size of a small melon. It had a furry interior that felt good against his penis. Victoria fixed it into place by securely tying the device with two large bows behind his back.

“There you are, you’re almost ready to be reborn as a girl.” The two mistresses each put on a red rubber apron. Gemma then brought a couple of bottles of baby oil from one of the draws and passed one bottle to Victoria.

“Hold still now Leanne.” said Gemma. “We need to make your body nice and slippery.” They began to quickly cover his body in the oil from the neck downwards to his feet. They each cleaned the excess oil from their hands then took him over to the sissy womb. Victoria bent down, undid the zip at the entrance, and parted the soft rubber lips.

“Bend down dear and climb inside.” Reluctantly he bent down and pushed his way into the opening headfirst. The rubber lips of the pussy created thrilling sensations as he slipped through. There wasn’t much room so he had to squeeze inside. The inside was quite warm with a strong smell of rubber but was quite sensual against his skin. “Now if you’re a good girl and quiet I’ll give you creamy milk in your feeding bottle tomorrow.” said Victoria. Gemma laughed

“Oh Victoria, your much too nice to him.” she said as Victoria slowly and tantalisingly zipped him inside. The mistresses busied themselves tidying up for a couple of minutes, Gemma set a timer on a small control panel for the ‘process’ to begin. Victoria placed a heart shaped padlock on the zip to prevent any chance of escape. With that, they had finished for the night. “Fancy a glass of wine dear?” Victoria asked Gemma as she switched the basement light off, he listened to the tapping of their shoes heading up the stairs and then silence, he was completely alone in his slippery rubber dungeon.

About an hour had passed when something began to happen, the inlet from on top of the womb began to feed in oxygen accompanied by an erotic scent. He recognised it immediately as his wife’s stockings and shoes, just as Gemma and Victoria had promised. The smell of shoe leather mixed with Elizabeth’s sexy foot smell immediately made him aroused. The sissy womb began to vibrate making his body move against the pink rubber. The masturbator on his penis also then began to work. Now he was very aroused as his entire body slipped and slid against the womb’s rubber walls. He breathed in the leather mixed with feet smell of his wife’s shoes. He felt tortured as the womb allowed him to smell them but not lick or kiss them. This heightened his arousal. The masturbator began to speed up, he couldn’t hold back any longer. He breathed in deeper and the furry inside delicately massaged his penis to a fantastic climax. A short while after climax the whole thing stopped. Sealed into the confined space he fell asleep. He was awoken the next morning by Gemma shouting

“Wake up baby Leanne.” Victoria undid the entrance zip. “Come on, its time.” He weakly began to make his way to the entrance, it wasn’t far at all but he was exhausted. He slowly dropped out from the pussy and collapsed on the PVC sheet.

“It’s a girl!” the mistresses shouted. “Come on, no time for a rest, stand up.” demanded Gemma. He struggled to his feet. Victoria undid the bows attached to the masturbator and pulled it off his penis.

“Had a fun night I see.” Victoria said looking at all of his cream in the masturbator.

“Get inside this bag.” demanded Gemma. “We don’t want you ruining the carpets with baby oil on your way upstairs.”

In the bathroom, they showered him down, got rid of all the baby oil and bathed him in a sweet smelling lotion. After being dried he was led to a room marked ’Nursery’. A changing table was all laid out ready covered in a white rubber sheet. “Lay down on the table.” ordered Gemma. He was talcum powdered by Victoria then Gemma put him in a diaper, followed by a plastic diaper cover. He could not believe he was being treated like a baby girl, he felt ashamed. Next came a frilly pink baby dress, a bonnet and a pair of pink satin bootees with large white pom-poms on the end of them. As the charming bootees were slipped onto his feet, he went red with embarrassment. How could they do this to him, he thought. They led him down to the kitchen and placed him in a high chair. Mistress Victoria gently pushed a baby’s feeding bottle into his mouth. It was filled with creamy milk just like she had promised him for being quiet during the night. He started sucking from the bottle, it had a very calming effect on him. He began to look at Victoria in the same way a real baby girl would to her mother. His gentle sucking continued until all the milk had gone. She removed the empty bottle from his lips, still gazing into each others eyes as if they were mother and baby daughter, Victoria suddenly felt very affectionate towards him and covered him with kisses. Mistress Gemma smiled and shook her head, then went back to eating her breakfast.

Later on, he was in the living room sitting in his baby chair, Victoria was reading magazines. He suddenly needed the toilet.

“Victoria, I need the toi…”

“NO” interrupted Victoria. “You can only use baby talk…let me hear you again.” He thought for a second how a baby would say it.

“Victowia, I need the toiwet.”

“But you can go whenever you like dear…in your diaper.” In the DIAPER? The thought of wetting himself made him very uncomfortable. He made one last attempt to plead with Victoria but she threatened him with the sissy spanker if he didn‘t keep quiet. An hour must have gone by and he was still holding it back. Eventually in was no use and a warm jet of baby wetties soaked his diaper. Embarrassed and helpless he quietly moaned to himself about what he had just done, Victoria briefly looked up, smiled and went back to reading her magazine. A while later, when she’d finished she took him upstairs to the nursery for a diaper change. His wet diaper was removed and disposed of. With his legs in the air, he was carefully wiped down and talcum powdered. Victoria was clearly enjoying every minute of it. When finished Victoria looked out of the window.

“It’s a lovely day today, why don’t we go out.” Lee was horrified by this suggestion, he did not want to be seen like this by anyone.

“Pwease Victowia n…” his protest failed as she gently thrust a pink dummy into his mouth. He was bundled into a giant pram outside, Victoria raised the hood and off they went down the street. The trip around the posh suburbs was interrupted while passing a small group of shops. Three ladies were standing outside chatting when one of them noticed Victoria coming.

“Ladies look, Victoria has the pram.” Excited they all rushed over to her. She greeted them and asked if they’d like to see the little baby.

“Yes please.” came the answer. Looking under the hood the ladies all began to squeal with delight at how cute this baby was.

“What’s her name?” asked one of the ladies.

“Leanne” replied Victoria.

“Who was she before?”

“Elizabeth’s husband.” answered Victoria.

“Really? The lucky lady.” Victoria lowered the pram hood so the ladies could kiss the baby. He was showered by kisses and more cutie remarks. As the day went on they arrived back home, Victoria sat him on her knee and gently fed him. At his bedtime, she took him upstairs to the nursery and put him in the crib to sleep. She gave him a pink stuffed toy to sleep with, and kissed him goodnight.

He was woken up early the next morning by Victoria who had ’good’ news for him.

“You’re finished being a baby, now its time to become a little girl.” said Victoria. She gently dressed him in a pink dressing gown and a pair of fuzzy pink slippers and took him to the kitchen were he was quickly force fed his breakfast, then up the stairs to the bathroom. There Gemma was waiting with a hot soapy bath. She took the dressing gown and slippers off him and put him in the bath.

“This’ll give you a nice little girl smell dear.” she said as they washed him down. He was dried with some white fluffy towels and taken to a room marked ’Little Girl’s Room’. A little make up was applied first to give his face a soft little girl complexion, a blonde Shirley Temple wig was placed on his head, then came the underwear. A pair of pink knickers with a my little pony on them. “Leg up, dear.” said Victoria. She pulled the knickers up over his erect penis; Gemma dropped a petticoat over his head which she then arranged into place. Victoria put a pair of white tights onto his smooth legs.

“Now for my favourite bit.” said Gemma. She walked over to the wardrobe, took out a dress, and held it up so he could see. “Do you like it?” she asked. His mouth opened and his erection bulged even bigger. The dress was a very pretty pink party dress with puffy sleeves, ribbons and gleaming sparkles. The empire waist had a large white sash that tied into a darling bow at the back. The skirt had rows of pink bows descending down the dress, which ended with a band of white frothy lace.

“Answer Gemma.” said Victoria nudging him.

“Yes, mistress, it’s very pretty.”

Gemma grinned at him “I’m sure everyone will think you look pretty wearing it dear.” Before he knew what was happening Gemma had brought the outrageously feminine garment over his head and pulled his arms through the sleeves. As she zipped up the back of the dress Gemma smiled.

“Now you look the picture of pre-school femininity.” Victoria tied the sash at the back of the dress into a large butterfly bow.

“Now we have a present we‘ve been saving for a special little girl like you.” Victoria brought out a box from the bottom of the wardrobe and opened it in front of him. Inside was a new pair of Mary Jane shoes. They were bright pink with sparkly bits around the front and across the strap. Gemma took one of the shoes out of the box, placed her right hand inside and smoothed the sole of the shoe down his face.

“Do you like them Leanne? “Asked Gemma.

“Yes mistress.“ he nodded.

“Good, well, give it a kiss.” instructed Gemma.

“Wha…”

“Don’t try to argue, just kiss it” He kissed the shoe, Victoria presented him with the other shoe.

“And the other.” said Victoria. When he had kissed the second shoe, she pushed him down onto the bed. The dress flounced around him, he felt the shoes being slipped onto his feet and buckled up. She pulled him up, placed some dainty white gloves onto his hands, and fastened them into place with the pearl like buttons. He was taken over to the mirror to see the beautiful little girl he had become, the frilly dress rustling as he walked. “Don‘t you look lovely?” said Victoria.

“This is for your lesson in humiliation dear.” said Gemma teasingly. “You’ll be spending the day inside the puffy pod.” They led him downstairs to the back garden where the two sisters had something waiting for him. It was a small round platform with wheels built onto its underside, on top was a stool covered in pink fur. Attached to the lower side of the stool were a pair of ankle restraints also covered in pink fur, and two wrist restraints attached to the side of the stool. They sat him down on the stool, attached all the restraints and lowered a transparent plastic dome over the top of him. The whole thing was about five feet in height and was topped off with a giant pink bow on top. To his horror, they then wheeled him to the front garden where he was in full view of any passers by. After a few minutes the postman walked up the driveway, he stopped at the sight which greeted him. Victoria reassured him that HE was ok.

“HE???” asked the postman.

“Yes, have you got any post for us?”

“Uh…yeah, here Miss Stiletto.” He handed Victoria the mail, took one last look and hurried off. Victoria laughed at what had just happened. A group of schoolgirls later passed by. First, they seemed shocked then they just laughed. One of them even commented that she wouldn’t have worn a dress THAT girlie even at the age of four. Gemma pointed out to them that he was wearing my little pony knickers. They all laughed. The humiliation became too much and he became teary eyed, then they all laughed at him again. At late afternoon, they finally let him out.

That afternoon he was in his girly bedroom with Victoria.

“Now dear, its time we taught you how to be a nice cuddly sissy for when your mistress is in that mood.” She took out a pink teddy bear costume from the back of the wardrobe. This is what you’ll be wearing tonight sweetie…oh, your going to look so cute. She started by putting him in a pair of training pants. “We don’t want you messing up the costume do we dear?” Next came the costume, all bright pink that was slightly padded at the front and on the bottom to give it a teddy bear shape. Once inside Victoria put the bear glove hands on him followed by the bear feet. Finally, the plush bears head was gently pushed down onto his head. Victoria’s final touch was a shiny glittering pink skirt. “There now, you look lovely.” She led him by the hand to the living room. On passing the large mirror in the hall, she told him to have a look. Looking back at him was a large pink plush bear wearing a little sparkly pink skirt. He realised he looked cute and began to feel dainty. On walking into the living room, Gemma looked up from her magazine and laughed.

“That costume’s always a sight whoever wears it.”

“Leanne.” said Victoria. “Curtsey for Gemma” The bear curtseyed and Gemma laughed again before leaving the room. He felt upset by Gemma‘s reaction. “Don‘t worry about her, sit down here.” said Victoria, pointing to her lap. He did so and Victoria put her arms around him. “Now you have to be very cuddly so put your arms around me.” He did as he was told and began to hug her. Next, she extended her hand down to his groin and undid a concealed zip in the costume, reaching inside, she touched his penis through the training pants. He gasped as she slowly and gently began to massage his penis. “Isn’t this lovely sweetie?” “Yes mistress.” came the muffled answer. “I do like cuddly sissies.” she said as she speeded up her playful hand. “Did you enjoy being humiliated in the puffy pod today Leanne?“ asked Victoria.

“No mistress.“ he shyly replied.

“Why ever not Leanne?“ Victoria’s hand began to slow down.

“They all thought I looked silly.” he said sadly.

“Is that all Princess?” He nodded. “But wasn’t it fun being put into a frilly dress, sat on a fluffy stool and presented to the community? I bet your penis was hard when you went into the pod”

“Yes mistress.”

“And did it get harder when those girls laughed at you?”

“Yes mistress.”

“There you see you did enjoy it, I thought you did from the wet patch in your knickers.” She speeded up her hand again. He moaned out loud and she hugged him tighter. Finally, he splashed the training pants with his cream and as he did, he hugged her even tighter. “Now you know why I made you wear training pants dear.”

The next morning he was dressed in a pair of navy blue knickers, a white blouse, a grey gymslip, white socks and a pair of black dolly shoes that had a pointed toe and small heel. “Now then young lady.” said Gemma. “We’ll start in my bedroom.“ First thing tomorrow after you dress, you will bring my breakfast to my bedroom, and when I am ready, you will help me choose what to wear for the day and help me dress. Is that clear?”

“Yes mistress.”

“Good. Victoria will help you since it will be your first attempt. After that, if you fail I will spank you. Next Gemma moved onto the kitchen and showed him where everything was and what his duties were. Next was the housework, duties included vacuuming, tidying up the house and serving meals. Later on that day Gemma took him for what she called ’How to please the mistress’. It started with him being instructed to kiss and lick her shoes. Soon afterwards, he was told to remove her shoes and stockings and massage her feet. Finally, he had to kiss their feet and suck her toes. Moving on from her feet stood up and slid her panties down. “Now I want you to give my pussy and clit a good licking. He was shocked at this but did as he was told. He let his tongue glide in between Gemma’s pussy lips and explore her inside. “Mmmm, not bad Leanne, a little more speed with your tongue please…..yes, that’s it.” she moaned as his tongue lapped quicker. After ‘school’ he was taken back to his brightly coloured pink bedroom. He couldn’t keep his eyes off Victoria’s white knee boots. Victoria held up two dresses and asked him to choose. One was a light blue dress with pictures on the hem of bunnies, the other was yellow adorned with teddy bears. He chose the blue dress.

“You look very nice in that dress…what are you looking at?”

“Sorry mistress.”

“You were looking at my boots weren’t you?”

“Yes mistress.” He said shamefully.

“Would little Leanne like to try on her Aunty Victoria’s boots?”

“Could I mistress?” He asked excitedly.

“Of course you can dear.” she said as she unzipped her boots. “Put your feet up on my lap darling.” He did as he was told, Victoria then slid the white leather boots onto him and zipped his legs inside. “Stand up Leanne, how do they feel?”

“Lovely.” he replied.

“Good, let’s get you to walk in them shall we.” She led him by the hand downstairs. He paraded up and down the hallway for a few minutes, the boots heels clacking on the wooden floor. “All right I think that’s enough, those boots don’t really go with the dress so let’s find you some nice Mary Janes.

The next day he was to learn how to be a maid, so he was dressed in a French maid’s uniform, black fish net stockings and high heels and was instructed on how to properly do the housework. After being dressed as a maid and having a few minutes to acclimatise himself to the high heels, he was told how to prepare Gemma’s breakfast. He took it up to her. He knocked on her door, a voice told him to come in.

“Your late you silly girl, put the tray by the window and go prepare my bath.” yes mistress. A short while later Gemma returned to her room where Lee was waiting to serve his mistress again. “I’ll put my make up on myself today, I don’t want you attempting with those shaky hands.” “Now, hand me a nice pair of black silky panties and bra from the draw. He opened the draw, took out a sexy lacy bra and matching panties, and handed them daintily to Gemma. “Thank you darling, now avert your eyes you filthy bitch, my body is not for little girls’ eyes.” He turned around. “Good, now a garter belt and black sheer stockings Leanne, second draw down, and be quick about it this time. He scrambled to the draw and took out the requirements. Gemma took the garter belt from him, put it on, sat on the bed. “Now put the stockings onto my legs Leanne, Carefully.” With her stockings on straight Gemma began to think about her outfit. “Something in black I think dear.” He searched around for some black outfits, eventually he came up with a black mini-dress, or a clingy black top with a black pvc mini-skirt. “Well that’s not a bad selection Leanne for a first timer such as yourself. Hold them up higher, I want to be able to choose properly.” she snapped. He held them up as best he could. “Hmm…I think I’ll wear the top and mini-skirt today.”

“Yes mistress.” he replied as he laid the outfit on the bed and put the other away. Without Gemma giving instructions he knew what he had to do next. He gently wrapped the smooth skirt around her wondrous body and buttoned it up. Next, he helped her into the top and zipped it up at the back. “Now, shoes Leanne, I think I’ll wear the red stilettos.” He looked to the bottom of the wardrobe where the huge collection of shoes were. Several pairs fitted that description. “The strapless, four inch heeled shoes, near the back.” she shouted. “I’m sorry mistress.” he said as he walked over to her. “Honestly, you’re not going to make a very good maid for your mistress if you take this long for the simplest of tasks.” she remarked in a very condescending tone. “Now put them on my feet” she said lifting a leg up. With both shoes on, she got up and walked across to the bedroom mirror. “You don’t think I’m dressed a little too tarty do you, Leanne.”

“Err…NO mistress…of course not.” he spluttered. Gemma slowly turned to him with an almost evil smile.

“Good, because if I find you chose this outfit just to get a look at me, I’ll have you whipped. Understood?”

“Yes mistress.” he said terrified. The day went on without incident, he performed house duties such as vacuuming and tidying rooms, and with a house of that size it took a long time. By late afternoon he was just finishing, and exhausted, after having to clean several rooms more than once to meet with Gemma’s high expectations. Sitting on the living room carpet with Gemma on the sofa watching TV. She got up to adjust her hair in the mirror. His eyes accidentally wondered to the figure hugging mini-skirt. She saw him glance at her in the mirror. ’Ha, got him.’ she thought.

“You were looking at my skirt weren’t you?”

“No mistress.”

“Don’t lie slut, young girls such as yourself are supposed to be honest and innocent, not liars who have perverted thoughts about their mistresses skirts.” barked Gemma. “Take your dress off!” He meekly obeyed removing the maid’s uniform standing in only his shoes and underwear. Gemma returned with a cat o nine tails. ’Oh no, this will really hurt’ he thought to himself. “Bend over.” she barked. He bent over the arm of the sofa with his face buried into the cushion. She ripped his knickers down to his ankles, held him down with her left hand and began the punishment. The first blow came and really hurt, he screamed in pain but was muffled by the sofa. More hits followed. “Don’t …ever…look…at…your…mistress…in that…way…again. You…filthy…PERVERT.” She ceased her attack, his bottom glowed bright red. He collapsed to the floor. “I hope you’ve learnt your lesson you filthy trollop.” she said triumphantly. He nodded his head as he pulled his knickers back up. “Yes, I’ll bet you have, I think I should put you off girls in their skirts forever. Lie down on the floor.” He did as he was told, laying on his back dreading what she would do next. She positioned herself above him with one of her shapely legs either side of him, she smoothed down the skirt, lowered herself and sat on his face. The coolness of the black pvc was smothered all over his face. She started to make small circular movements with her bottom. She laughed at him as he began to gasp for air underneath her. “What’s this? Having trouble breathing?” She raised herself for a few moments to allow him to breathe, then she continued to smother him with her skirt. His arms and legs began to move furiously as he struggled to breath, so much so his shoes came flying off, to the obvious sheer delight of Gemma. After the skirt-smothering ordeal, he was sent to bed. Humiliated, he resolved never to look at his mistress in that way again.

Ten days of maid training past, full of spankings and unusual punishments from Gemma, and lots of dressing up and ritual humiliations by Victoria. At the next adult little girl kindergarten, he was forced to dress up in a white bunny costume while six men dressed as Alice in wonderland hurled Victoria and Gemma’s used panties at him. Then to add insult to injury Gemma, dressed as the Queen of hearts, demonstrated what she thought should have happened to the white rabbit for being late. She placed Lee into a toilet box and urinated onto his face.

The last day finally came,

“Come on Leanne, Elizabeth will be here soon to collect you. We have to get you ready.” said Victoria. At about six o’clock there was a knock at the door. It was his wife. “Hello Elizabeth.” said Victoria. “Come in, we have him all ready in the living room.”

“No trouble I hope Victoria?” asked Elizabeth. “Oh no trouble at all dear.” answered Victoria. On entering the living room everything looked normal to Elizabeth’s eyes…except for a darkish pink round bag in the middle of the room.

“Is he in there?” The two sisters nodded. She opened up the bag and inside was Leanne in his gingham dress and Mary janes, along with a blonde wig with pigtails. “There you are darling, I hope you’ve been good.”

“Lets get her to the party shall we?” said Elizabeth.

“His make up is all done Elizabeth. We just need to dress him when we get their.” They bundled him into the car. Victoria sat with him in the back. He couldn’t help noticing the pink bag Gemma was carrying. Soon enough they arrived outside a tall building in a nearby city. It was the office block where he had once been an executive in his life as a male, where he had met Elizabeth who was now chairwoman of the board. In the lift he began to sob uncontrollably. He remembered this was the very place he had met Elizabeth. Back then she was an office worker, Lee was an executive who seemed to have an unhealthy interest in her clothes. She was intrigued by this perverted executive and accepted his offer to ‘Come back to his place.’ After an affair that lasted for eight months, she received a promotion onto the board. When she was an executive like him, his usefulness in the office to her had past. So she set a silky trap to be rid of him from the office. One night he had a little drink, he was sitting relaxed when Elizabeth set her plan in motion.

“Lee, how about we try something really sexy tonight?”

“What like?” he asked boldly.

“Do you dress up in women’s clothing?” she asked. He laughed

“Why would I want to do that?”

“Some men find wearing women’s clothes sexy.” said Elizabeth.

“Would you like to try on mine?”

“What…seriously?” he asked slightly tipsy.

“Yes why not? Everything from my necklace down to my shoes.”

“Ok, I’ll give it a try.” They both stripped off. Totally naked she handed him her knickers, he pulled hem up. ‘This doesn‘t feel too bad‘ he thought to himself. On went her lacy bra, she helped him pad out the cups with large amounts of tissue paper. She smoothed the stockings up his legs and fixed them into place. Next came the black evening dress, she pulled it over him and zipped up the back, she slipped her patent black high heels onto his feet and put the gold necklace onto him. He felt strange but did not dislike it.

“Allow me to put some make up on.” said Elizabeth. He agreed, she reached for her handbag, took out some make up and began to apply plenty of foundation, mascara and red lipstick. She took out a long blonde wig from her handbag and carefully placed it on his head. “All finished, go look in the mirror.” she said as she gave him the handbag. He wobbled in high heels, looking into the mirror he was stunned into silence his erection grew even bigger. He frolicked around in his girlfriend‘s attire for a while longer before making love to her on the floor, still dressed in women’s’ underwear. Two months later, they married and only a month after that she suggested he quit his job and become a full time sissy. He agreed and his life became full of skirts and dresses. If he had thought things through he may not have agreed, but female clothing just felt so good.

“There, there.” said Elizabeth. “Your sad about coming back here aren’t you.” He nodded. “Tell you what dear, if you are a good little girl tonight and don’t cry, I’ll let you have a session with my shoes when we get home.” A wave of naughty girlish excitement came over him, he stopped crying. They all went into Elizabeth’s office, the party could be heard just down the corridor.

“Now to get him ready.” He was completely stripped and touch ups were made to his already well made up face. Gemma applied a little perfume while Victoria put a long black wig into place. Next came his costume, a Bunny girl costume. Elizabeth sat behind her desk, watching her husband and former boss being dressed up in the humiliating outfit. First came a shiny black outfit. Gemma put some ample sized breast forms inside. A couple of black fish net stockings followed, his bunny tail was fixed to the dress and a pair of bunny ears were put on his head. The finishing touch was a pair of five inch white high heeled shoes. He slipped his feet inside and he was ready to go.

“Now you refer to me as Aunty Elizabeth here, understood Leanne?“

“Yes Ma’am.“ he replied. They walked into the party, Elizabeth holding Leanne’s hand and she shouted for attention. The people were unaware of the bunny girls true gender and who it really was.

“As you all know my husband can’t be here tonight because of his new job in Canada.” announced Elizabeth. “So instead here is my niece who will be serving the champagne tonight.” He went out into the party and started serving the drinks. One of the men gave him a playful pat on the bum as he walked away.

“Are you mad?” asked his co-worker. “That’s the boss’s niece.”