Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: DaraJaney on July 07, 2020, 02:45:08 AM
-
Joe’s mother was very concerned about his granny since the coronavirus problem started. She was a fairly healthy 70 years of age but the advice was for people of that age to shield by staying at home because they were at high-risk.
But how was she to shop for vital supplies? People were reporting shortages in the shops due to stockpiling. She used to have a very supportive community around her but she’d outlived most her neighbourhood friends and others moved away. There were new families in the houses either side of her. She didn’t know them well and if you asked them to shop for you, how could you be sure they were being careful enough?
His granny didn’t seem too concerned but his mother was worried that she was just putting a brave face on it. She decided she should visit and see the situation for herself.
It was a three hour drive but his mother didn’t mind driving there and back in the same day. It was probably better if they didn’t stay over in case a stricter lockdown was imposed and they were stuck there.
So they drove there noticing little traffic on the motorways. There was definitely a growing sense of unease. They had taken every precaution – using hand sanitisers, washing for the recommended two ‘Happy Birthday’s. Everything was still open but people were starting to avoid pubs, restaurants, theatres and public transport.
Some other countries seemed to be taking it more seriously. All St Patrick’s Day parades were called off in Ireland. An international conference in Spain she was due to go to for work had been cancelled.
When they arrived his granny insisted she was ok. She had plenty of food and supplies. She could order deliveries online. But his mother, as ever, continued to worry. She had heard that the wait times for deliveries were increasing.
She made his granny go through an online order for groceries and they found that the queue was two weeks! Now his mother was really worried. She couldn’t see how his granny was going to fend for herself alone.
Joe eyed the clock anxiously as his mother fretted into the evening. She couldn’t bring herself to leave his granny, not knowing when they would be able to see each other again.
She decided that they should stay the night. Maybe they could do a big shop for her tomorrow. Joe sighed but couldn’t really complain. He hated staying over at granny’s though. He always had to sleep in his mother’s old room. His granny hadn’t touched it since his mother moved out when she went to college.
She’d always been the nostalgic sort and had kept lots of his mother’s nicest clothes long after she’d grown out of them. The bed linen was embarrassingly feminine and old fashioned for Joe. Lacey trimmings on the pillow cases, flowery duvet cover.
His mother was always amused at his unease having to stay in the room. “It’s just for one night”, she emphasised but still giggled on glancing at the bed he was going to have to sleep in.
He started to unbutton his shirt. “There are nice frilly nighties in the drawer there if you like”, she tittered as she closed the door. He glared at the closed door and stripped down to his underwear.
He always slept badly there. Everything was so soft and fluffy. He sank into the mattress. He had a really firm one at home. In the morning it always seemed a struggle to extract himself from the bed. It was like it was swallowing him up.
In the morning he had to dress in the same clothes after his shower. His mother decided to do a big shop. There was a huge queue to get into the store which only added to the sense of fore-boding.
When they got back to his granny’s house, she was watching the news. The government had announced a lockdown. Everyone was to stay at home, work from home where possible. They were not to travel any further than absolutely necessary to buy their supplies.
They unloaded the car. His mother stood with her hands firmly on her hips, thinking. “We’re going to have to stay”, she decided. “What? No!” Joe protested. “I don’t have anything here.” His mother ignored him. She had bigger concerns.
“We can’t leave mum here on her own to fend for herself. We’re staying.” “But .. we don’t have any clothes here. I don’t have my laptop or Playstation!” She frowned at him. “You and your computer games, that’s the least of our problems. No! We’re staying. We’ll figure it all out.”
-
DaraJaney, Nice start to your story. The COVID-19 pandemic has caused many inconveniences in our lives. Joe is about to find out about those hardships. The biggest one will be "not" having any clothes with him now that there has been a lockdown. That is, unless he wears what is in the wardrobe.
Can't wait for the next installment. 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8)
-
Nice story using the situation going on now as inspiration for a story, poor Joe stuck at his grandmas house without any change of clothes except his mother’s old clothes in his room which would amuse his mother greatly
-
I think some of this might be premeditated on mom's part. Joe could feel the foreboding, so why didn't she think to get him at least a few things? Very curious
-
The next morning Joe extracted himself from the soft fluffy lacey bed and went to have his shower. When he returned his clothes were all gone. His mother entered the room. He clutched his wet towel. “Where are my clothes?”
“You couldn’t wear those another day. I’ve put them in the washing machine.” He could hear the water gushing into the machine in the utility room. “So what am I going to wear?” he asked nervously.
His mother opened the wardrobe revealing a dozen or so of her best dresses from when she was a girl. “Which would you prefer?” Joe frowned. “You must be joking!” His mother remained calm. “It’s your choice. Mum never kept any trousers or shorts just my old dresses. You won’t be leaving the house anyway”, she assured him.
Joe just stood clutching the wet towel which appeared to be his only alternative to a dress. His mother pulled out a drawer. Joe watched. There was a pile of panties. His mother held a pair up. They had rows of lace across the bum. Joe felt sick but she tried the next pair. They had a floral pattern with lace trim. She worked her way down.
“Oh these are plain white”, she held them up. “Just a lace trim around the legs.” She placed them on the bed. Joe looked at them in horror but he was starting to feel the chill of his wet towel. He looked again at the flowery frilly panties and had to accept she had given him the best option.
He quickly dropped the towel and stepped into the white lace-trimmed panties. They were quite tight on him but did the job. He waited for his mother to chuckle at him or tease him but she just went to the wardrobe.
She took out a royal blue dress which had white cuffs on the sleeves and a white collar. The sleeves were slightly puffed and the skirt was pleated. Joe surveyed the other dresses. He saw pink and various pastel colours he couldn’t describe, floral patterns, layers of lace, full skirts, frilly hems.
He supposed the blue dress was the least embarrassing. He couldn’t believe he was doing this but what choice did he have? There wasn’t a dressing gown in sight.
His mother threw the dress over his head and when his arms were in the sleeves, zipped him up. She tugged at his skirt until the pleats were all straight. He looked in the mirror. It came to a couple of inches above his knee. He didn’t like the way the pleated skirt stood out or the puffed sleeves but one look at the alternatives in the wardrobe was enough to convince him this was the least worst option.
His mother was already looking in the drawers for socks. She held up a series of pairs of ankle socks. “They all have frilly lace.” Then she started rummaging through the tights. Joe felt sick again. He spotted a pair of silver slippers in the bottom of the wardrobe. “I can wear these”, he suggested. His mother shrugged. “OK. You won’t be going out anyway I suppose.” Joe felt a bit reassured.
He tried not to think of the following days and didn’t look again at the range of dresses in the wardrobe. He went to the kitchen for breakfast. His granny smiled when he walked in. “Oh I did love that dress”, she sighed, tugging at the puffed sleeves. Joe tried not to look too embarrassed as he sat at the table.
He was relieved that his mum and granny didn’t make much of it. He hung around the house looking for something to do. His mother’s room was full of old girl’s comics and magazines and typical girly books like “Little Women”. His granny’s choice of movies wasn’t any better. He saw “Beaches”, “Steel Magnolias” and didn’t look any further.
He heard laughing outside. He went to look out the window into the garden but remembered he was a boy wearing a dress so stayed to one side. He could see a girl playing in the back garden next door. She looked about 8 or 9 maybe. She was skipping. He looked enviously at the trousers she was wearing.
Then he heard a football against a wall. He carefully switched sides of the window and saw a boy about his own age kicking a ball around the garden on the other side. Joe looked down at his dress. There was no way he could go out in front of that boy dressed like this.
He searched the house for something to do. Was that a board game on the top shelf? He took it down. It was a girl’s play make-up kit. He found a box of clothes in the corner of the wardrobe but when he examined them, they proved to be fancy dress costumes and wigs like for a princess or Dorothy.
He sighed and sat on the bed. He fiddled with the pleats on his dress, looked at the make-up kit momentarily and then shook his head. He wasn’t that desperate!
The next morning his mother gave him a yellow dress to wear. It was probably the next least embarrassing but had lace frills over the shoulder and was a little shorter. She had found a yellow pair of panties too. They had two lines of lace across the bottom but there wasn’t anything less embarrassing in the selection.
After breakfast his mother caught him looking longingly out the window at the children playing in the neighbouring gardens. It was bright and sunny. “You could go out, you know.” He looked down at his yellow dress and shook his head disconsolately. “Well, we could be here for a couple of weeks. Are you going to mope around the house all that time?”
“Can’t we borrow clothes from a neighbour?” he pleaded. “No. We can’t call in to other people, we are supposed to be isolating. These are new neighbours, mum doesn’t know either of them well enough. And the department stores are all closed.”
He sighed again. “I could make you look like a girl so it wouldn’t be so embarrassing”, she suggested. He thought about it. His short hair was a definite giveaway. “There are those wigs in the dress-up box.” He looked out at the children again. He was going mad with boredom but could he walk out there in front of that boy in a pretty dress? The thought turned his stomach.
-
Great scenario. And lockdown lasts a nice long time....
-
By lunchtime, he couldn’t take the boredom and looking out at the other children playing any longer. “Mum I want to go out in the garden.” He was looking down at the floor as he said it. He realised the implications. He would need to look convincingly like a girl. His stomach was churning at the idea.
His mother decided that the princess wigs were too fancy but the Dorothy one was reasonably plausible. She tied yellow ribbons to the ends of the pig tails to match his dress. He had to decide did he want to wear frilly ankle socks or white tights. He stood looking gloomily at both unable to decide which were least mortifying. In the end his mother convinced him that it was still a bit chilly in March so he should wear the tights. She also insisted that the yellow panties with the frills had to be worn over the tights. A pair of black Mary Janes were found that fit him.
His mother stood back and studied her son in the yellow dress with lacey frills over the shoulders, the wig with pigtails tied with yellow ribbons, the white tights and Mary Janes. The flared dress fell about four inches above his knees.
“I know you are sixteen but it might be better to say that you’re ….”, she thought about it. A sixteen year old girl wouldn’t be seen dead dressed like that these days, she knew. What was the youngest age he could get away with? “… thirteen?” Joe looked wounded but a glance in the mirror was enough to convince him she was right.
“Come along then.” He really had a sick feeling in his stomach now. He was about to walk out into the back garden in a sissy dress, tights and pigtails! He could hear the football against the wall and the girl chanting a skipping rhyme. But he couldn’t stay indoors any longer with nothing boyish to do anyway.
His mother opened the back door and stood back for him to walk out. He swallowed hard and went out the door to the top of the steps down to the garden. The wind fluttered his short dress. He clutched the skirt nervously. “If you look panicked like that, they will be suspicious”, his mother warned him. “Try to look more confident and happy.” She was right. He gave a wan smile and went down the steps.
The boy next door saw him. “Hey!” Joe forced a smile. “Hey!” He could see the boy looking him up and down unimpressed, no doubt thinking what a sissy girl. If he knew! “I’m Barry.” “Joe … sephine.” Joe nearly choked on the name.
“There’s a ball of mine went over the wall earlier. Could you kick it back please?” Joe saw it at the foot of the fence on the other side. “Sure.” He walked over trying to look as convincing as possible, bent over and picked it up. He turned to see a wide smirk on the boy’s face. “No kicking a ball in that pretty dress and tights!” his mother warned from the door. Joe cringed. He went to throw the ball over the fence but in his awkwardness in the short dress made a pathetic throw which bounced off the fence and back behind him. Barry threw his eyes up. What a typically pathetic girl! Can’t even throw a ball properly.
Joe bent over and picked up the ball again. Barry’s unimpressed look had been replaced by a grin again. This time Joe managed to throw the ball over. His mother walked behind him. “You need to be more careful about bending over in that dress”, she whispered. Joe stood there mortified. Those frilly panties!
“Hello!” his mother called to the girl on the other side. “What’s your name?” “Hi I’m Jenny.” Barry had gone back to kicking his ball against the wall, clearly having decided that this sissy girl was going to be no fun.
“This is Josephine”, his mother introduced him. “Hi.” The girl waved. “Do you like skipping?” she asked. Joe shook his head. The girl was disappointed. His mother went back into the house. “How old are you?” the girl asked, looking pointedly at his frilly dress, tights and pigtails. “Thirteen.” That seemed to satisfy her though she undoubtedly still thought the clothes looked childish for that age. “I’m staying with my granny”, Joe added for something to fill the silence. “Oh”, the girl nodded. She reckoned that probably explained the sissy clothes. Joe couldn’t help eyeing her jeans enviously.
His mother came out again carrying two boxes, one on top of the other. She placed them on the patio. One was filled with dolls and the other with dolls’ clothes. “Why don’t you show Jenny your dolls?” Joe’s jaw dropped. His mother gave him an insistent look. “Maybe she can choose outfits for you to dress them in?” Joe was speechless.
“OK” Jenny responded, not particularly enthusiastically. It was clear that she thought dolls were silly but it was something to do if this girl wanted to. His mother handed him the largest doll which was in a pink gingham dress. “What’s her name?” Jenny asked. Joe wanted to die but had to think of something. “Jill.” “I think she’d look nice in that green dress”, Jenny suggested but it sounded like she was just humouring him.
Joe tried to smile and glare at his mother at the same time while starting to undress his doll. She smirked and went back to the house leaving them with the large selection of dolls and outfits which she reckoned would probably keep them amused for hours.
He bent over and picked up the green dress from the box. There was a snigger behind him. He froze and winced. He really was going to have to remember not to bend over!
-
Looks like this Jenny girl is a tomboy and wants nothing to do with his dolls and is probably wondering if this Josephine girl really is thirteen or just saying she is based on the way his dressed along with his lack of modesty given he flashed his panties a couple times and him still playing with dolls what thirteen year old girl plays with dolls still his mommy didn’t help his cause with that
-
DaraJaney, Poor Joe/Josephine, Nothing to wear but girl's clothes and being totally bored. Then he decides to go outside in his yellow dress with the frilly panties and tights. Joe/Josephine has no idea how to act like a girl and he gives the boy and Jenny a look at his panties instead of bending his knees to do things. I'm sure he will learn and he will gain confidence in his girlhood.
:P :P :P :P :P :P :P :P :P :P :P :P :P :P
-
I enjoy how every DaraJaney story hits the same points, but they're still able to feel fresh and new every time
-
As Joe struggled with the little buttons on his doll’s green dress, Jenny wandered off reckoning it would take him a few minutes to dress the doll. Barry next door was climbing one of the trees in his garden. Jenny proceeded to climb the tallest tree in her garden.
Joe eyed the excellent trees for climbing in his own garden but knew there was no chance he’d be allowed to climb in his yellow dress. Those frills over the shoulder would catch on everything and as for his snow-white tights … He rather grumpily sized up his doll in the green dress.
“How about that baby doll?” Jenny called from her tree. Joe looked in the box. There was indeed a doll in a fluffy pink dress. “What’s her name?” Joe sighed. “Penny”, he mumbled. He was about to bend over and pick it up when he remembered. He bent both his knees carefully, initially relieved that he was getting used to wearing a dress but then wincing at the thought of how long he was going to have to wear that range of sissy dresses in his wardrobe.
This continued for what seemed like a couple of hours. Joe dutifully named and dressed each doll in the box while the other children swung upside down from their trees or Barry kicked the ball about or Jenny skipped. They were only marginally less bored than we was. This new girl with the dolls being their only new diversion.
“Anything else in the box?” Jenny asked hopefully when he was down to the last doll. Joe picked up the skipping rope that was in the bottom of the box. “Oh great! I can teach you to skip!” Joe squirmed inwardly at the idea of skipping but then looked at the pile of dolls and dresses and decided anything must be better than that.
He held the rope in both hands while Jenny fetched hers. “It’s easy. It’s just a matter of practice.” She flipped the rope over herself a few times, stepping over it at the appropriate time with ease. Joe watched dubiously. He tried to swing the rope but with little confidence and it clipped the back of his head and tangled in his pigtails.
Jenny giggled. “You need to swing it harder.” She demonstrated again. Joe wasn’t sure he wanted to do this but she was insistent. The next time the rope went over his head but he mistimed his step and it flopped against his ankle.
He was concerned that the old rope had left a slight mark on his white tights and bent over to rub it. As he flicked a little dirt off, he realised that he was flashing his frilly panties to Barry again. He stood up quickly.
Eventually he was able to do a few swings of the rope as slowly as was possible and step over the rope. “Now you are getting it!” Jenny encouraged him. “You just need to speed up. That comes with practice.”
She went back to climbing as Joe practiced and was gradually able to keep going longer as longer and more quickly. He kept throwing a nervous eye at Barry concerned that his dress was flipping up as he jumped and flashing his panties. Barry was watching keenly alright and frequently had a smirk on his face but he had little else to look at and may well have just been amused at this teenage girl skipping in a frilly dress and pigtails. Either way Joe was mortified but what else was there to do? Go back to playing with the dolls?
By the end of the afternoon Joe was relieved to have gotten out of the house but the question was sinking in with him – how long was he going to have to dress and act like a girl in front of the neighbours?
The next day his mother selected a red check dress for him. The hem and sleeves had a thin lace trim but he was relieved that it came within an inch or two of his knees. She tied matching ribbons to the end of his pigtailed wig.
After breakfast his mother told him “there is actually a clothes section to the grocery store on main street which is accessible because the grocery shop has to stay open. I need you to get a couple of things there.” She held an envelope.
Joe looked distraught at the idea of going out in public in a dress and pigtails. “I thought you’d like the chance to get out”, his mother teased, looking down at his pretty dress and white tights. “We may have to stay here for weeks – possibly months.” Joe sighed heavily and took the envelope. “Give that to Mrs. Henderson behind the counter in the clothes section. The correct money is in their too.”
Then he had a thought. “Can’t I buy some trousers there?” His mother smiled patiently at him. “I’m not buying you a whole new wardrobe. And besides the neighbours think you are a girl now anyway. Are you going to let them know you are a boy who went out there in a pretty dress and pigtails and played with dolls and a skipping rope?” Joe winced.
He walked highly self-consciously to the main street. There were not many people around thanks to the lockdown but the grocery store was busy enough. He kept catching sideways glances from people who he reckoned were amused by his childish clothes. The breeze kept fluttering his dress but he tried not to clutch the skirt too anxiously and make it obvious that he was highly uncomfortable and unfamiliar with his female attire.
He found the clothes section. Mrs Henderson smiled down at his dress as she took the envelope. She read the note. “Ah yes. We have those over here.” She reached into the shelves behind her. “Six pack of rumba panties.” She took down a see-through pack with six pairs of panties in different pastel shades, each with four rows of frills across the bottom.
Joe felt sick. He thought she might not think they were for him. “Girls Large size”, she confirmed from the note and smiled at him. Joe cringed. “Aren’t they pretty?”, she commented. Joe forced a smile but couldn’t bring himself to utter anything. “Which colour will you wear first do you think?” Joe wanted to die.
Mrs Henderson consulted the note again. “And three pairs of lace patterned white tights.” Joe wanted to die. “There’s a large selection over here. Why don’t you pick your three favourites?” Joe looked at the dozen different designs of patterns on lacey white tights. “Again, the Large size should fit you”, she added helpfully. Joe pictured himself walking out in front of Barry and Jenny in lacey white tights with any of these floral patterns. He wanted to throw up.
He had no choice though but to quickly choose three pairs. The shop assistant handed him the pack of rumba panties and he clutched them along with his three packs of tights. “The self-service checkout is over there”, she added helpfully.
Pastel shades are relatively subtle but for Joe they might as well have been dayglo and he stood in the queue for the scanners. Ladies in the queue were glancing at the panties and tights and smiling, looking him up and down in his check dress and plain tights. They found that amusing enough.
He was relieved when he got to a machine. He held the pack of rumba panties to the scanner. “It gave a clunky beep.” They had failed to scan. An assistant came over immediately. Joe smiled apologetically as she took the pack of panties from him. It clunked again. She looked at the bar code, straightened the packaging and tried again. Joe looked nervously at the ladies waiting in the queue impatiently and watching everything that was going on.
The assistant sighed. “Mrs Henderson!” she called out. Joe’s jaw dropped. “How much is the six pack of rumba panties?” His cheeks must have been burning. “Girls Large!” Now everyone in the vicinity of the check-out was watching.
Mrs Henderson called out the price and the assistant punched it into the machine. Joe breathed a little more easily. “Do the three pairs of lacey white tights scan alright?” Mrs Henderson called back. Joe just looked at the floor.
The total was precisely ten pounds and he put the note into the machine. “If you need a plastic bag, they’re 5p”, the assistant added as she walked away. Joe instinctively felt for pockets but there were none in his dress. He looked nervously at the ladies watching from the queue. Had they noticed his faux pas? He didn’t even have the 5p. He cursed the plastic bag tax!
He had to walk home clutching the multi-coloured pack of frilly rumba panties and the three packs of lacey tights in his hands. He couldn’t make up his mind which to use to hide the others. He just tried to walk as quickly as he could as his dress fluttered disconcertingly in the rising breeze.
-
I love your stories, DaraJaney! No money for a pair of jeans and maybe a tee shirt or two but £10 for just rumba panties and lacy tights. Even plain white tights were not sissy enough. ;D They'll be there for weeks or even months and Joe's mother will spend the money to enhance his lingerie wardrobe but not a dime for boy's clothes. Me thinks earlier reviews were correct. Joe's mother set this up! Wonder when the baby clothes come out?
Perfect scenario for this "new normalcy". Thanks again for sharing your work.
-
DaraJaney, poor Joe is getting the full load of embarrassment. I'm sure he looks pretty on his dresses and tights and pigtails. How I wish that could be me dressed like that. ;) ;) ;) ;) ;) ;) ;) ;) ;) ;) ;)
-
Joe had been out in the garden in his red check dress all afternoon. Jenny had been teaching him skipping tricks. It was better than playing with dolls but he knew that Barry on the other side was watching closely hoping for flashes of Joe’s panties as he skipped. Joe knew that’s what he would be doing in the same circ-umstances. How he envied Jenny her jeans.
When he went back into the house his mother commented that he needed to do some share of the housework while they were staying in his granny’s. His mother was always on at him to do housework at home but it was so boring.
She looked at his expensive dress and said “can’t really get you to do dirty work in that nice dress though, can we?” For the first time Joe could see an upside to the pretty dresses that were all he had available to wear. He smirked at the dilemma his mother had identified.
She went to the broom closet and took out an apron. Joe frowned. She hooked the bib of the apron over his neck and tied the strings behind his back. It was quite a full apron and covered the front of his dress very well. “Now you can do some dusting”, she told him, fetching a feather duster from the closet. “You can start on the sitting room.” Joe frowned but did as he was told. His mother smiled. He was now well able to help with the housework.
The next morning his mother gave him the blue dress to wear again. His granny came into the room. “That apron reminded me …” She opened a drawer and took out a white pinafore. Joe looked on despondently as she put the pinafore over his dress. There were ruffles standing over the shoulders and around the apron. She tied the ribbons behind him in a bow. “There! That will help protect your dresses.”
Joe was highly conscious of his new pinafore when he went out in the garden to play though he tried to stop clutching it nervously which would betray how humiliated he felt. Jenny sniggered at his latest sissy accessory. It didn’t make skipping any easier as his shoulder ruffles and apron fluttered all the time. The ribbons on his pigtails snagged annoyingly on the shoulder ruffles too.
At lunchtime he discovered that his school had been in touch and had emailed a link to a new website for remote teaching. Fortunately, they didn’t propose online video calls but just sent exercises and reading materials. Joe was almost glad of the distraction but it wasn’t long before he got tired of schoolwork and he dawdled whenever his mother or granny weren’t looking.
Sunday came around. “We should still recognise the Lord’s day even though we are in lockdown”, his mother told him as she decided which of his floral dresses he should wear. Joe winced as she selected a pink and blue dress which he could see had lace peeking from below the hem.
When she made him put it on it transpired that the lace trim was on a petticoat which made the dress stand out even more than his other embarrassing dresses. The first pair of lace patterned tights came out as well as the pink rumba panties.
Joe was just relieved that they couldn’t go out to church as he tried to smooth his dress and petticoat under him as he sat at the kitchen table. He would still have to face Jenny and Barry in the garden but to be honest he was becoming accustomed to being embarrassed by the clothes he had to wear in front of them.
Jenny’s mum was sitting out in the garden and his mother did the introductions. The neighbour smiled at Joe’s floral dress and lacey tights. “It’s so nice to see a teenage girl who appreciates pretty dresses. I can’t even get her to wear a skirt on Sunday!” she added, frowning at Jenny who was quite pleased with herself.
“Why don’t you show us how your skipping in coming along Josephine?” his mother prompted him. He wanted to glare at her but had to maintain his forced smile as she fetched his skipping rope. The unfamiliar petticoat put him off as well as the fear of everyone seeing that he was wearing pink rumba panties.
His half-hearted attempts were not impressive. The rope kept catching in his flared dress and he was terrified it would pull his skirt up and show his panties. “You clearly need more practice”, his mother teased.
Later his granny realised that they were almost out of milk and he was despatched to the grocery store. He looked up and down the street nervously as his petticoat fluttered in the breeze. Fortunately the lockdown meant that there were few people around. Anyone he did meet smiled not so discretely at the teenage girl in rather juvenile clothes.
In the shop he turned a corner to be suddenly confronted with the lady who sold him the lacey tights and rumba panties. “Well hello!” Joe froze as she looked him up and down. She smiled seeing that he was wearing his new lace patterned tights. “Very pretty.” He instinctively smoothed down his dress and petticoat suddenly hyper-conscious of his rumba panties. She grinned knowingly recognising his discomfort which confirmed what she was wondering. “Do those rumba panties fit alright?”, she asked. Joe squirmed and tried to maintain his smile. He just nodded and scuttled on to the milk section.
-
DaraJaney, Another GREAT chapter. Poor Josephine is having a devil of a time with all of the juvenile dresses and his skipping. Jenny is having fun teaching Josephine to skip better and Barry just loves the panty shots he keeps getting when Josephine skips. The neighbors that came to visit probably embarrassed Josephine. That embarrassment was nothing compared with his trek to the store and meeting the sales lady that sold him the tights and rhumba panties.
Can't wait for the next chapter.
-
I think it'd be a lot of fun if Jenny whispered to Joe that she's known he's a boy from the get-go, perhaps because his awkwardness in a dress reminds her of the time she made Barry wear one of hers. I assume the author has much better plans forming though. :)
-
Before bed on Sunday night Joe’s mother complained that he wasn’t working hard enough on his schoolwork. “I read a suggestion somewhere that in order to ensure that a child focuses better on their home schooling they should be required to wear their school uniform”, his mother commented. “I can see the thinking behind that”, his granny agreed.
“Ha!” Joe responded instinctively. “Pity my school uniform is 80 miles away!” Although, looking down at his pretty Sunday dress and lacey tights, his grey uniform trousers seemed to go up a lot in his estimation all of a sudden.
“I think we still have your old convent uniform in the attic”, his granny recalled and she got up from the table. Joe winced. As he went to bed that night the green gymslip hung on the back of the door over its accompanying cream school blouse ready for him in the morning. A pair of bottle green tights were draped over the chair along with a belt, green ribbons and the green and cream striped tie.
He appeared for breakfast looking sheepish in his gymslip which was pleated from just below breast level with the cloth belt tied in a bow above his right hip. He ran his finger uncomfortably under the prettily curved collar of his cream blouse to try to loosen the tie a little. “Smooth your tights out dear. They’re sagging above your ankles”, his mother told him. Joe sighed and tugged his tights out more evenly above the knees before tugging the hem of his gymslip down reaching a few inches above his knees.
“Come here!” His mother insisted on retying the untidy green ribbons on his pigtails while he stood there grumpily. “You need more practice at this”, she giggled as she made the stiff bows.
His mother and granny actually supervised his school work much more closely so he had no choice but to focus on it. Then they proclaimed at the end of the school day that the uniform was clearly working.
“But now you can change into one of your pretty dresses for playing in the garden!” his mother announced happily as if he should be pleased with that. He looked down at his green pleated gymslip and thought he would actually prefer it to those stupid dresses.
But he went out into the garden in his yellow dress, white tights and yellow ribbons on his pigtails. Jenny and Barry noticed him clutching the skirt of his dress self-consciously. He was reluctant to practice his skipping but his mother was insistent that he needed the exercise.
He winced as he started to skip and despite his attempts to skip less energetically they were soon treated to glimpses of his yellow rumba panties. He grimaced as he thought that there must be a pair of rumba panties to go with every dress in his wardrobe.
On Saturday he was looking forward to some free time having been closely supervised with his school work all week. But after breakfast his mother insisted he had to help with housework and tied the apron over his dress. She handed him a feather duster and told him to dust in all the rooms.
Joe went around the rooms fluttering the ostrich feather duster. It seemed like a pointless exercise to him. The dust was just flicked up into the air but where was it going to go? It was obvious it was just going to settle again.
His mother passed the sitting room door as he was doing the bookshelves. “Right up into the corner of the room”, she instructed him. He could see a cobweb up in the corner so reached right up with the duster. His mother smiled at his lilac rumba panties before leaving him to it.
It was a sunny morning and his mother and granny decided to sit on the deckchairs in the garden. Around 11 am they could see Joe dusting around the window of the study. “Would you be a darling and bring us tea?” his mother asked.
Joe was actually relieved to get a break from the dusting. He went to the kitchen and put the kettle on. A few minutes later he appeared in the garden.
The ladies smiled from their reclined positions in the deckchairs as Joe approached in his pretty floral dress, protected by his full apron, clutching a tray with two cups and a tea pot. He placed it carefully on the garden table. His granny saw that he still needed lessons in decorum as he leaned forward without bending his knees. Still, that pack of rumba panties was a great buy, she was reminded.
“No biscuits dear?” Joe sighed and turned frustratedly to go back to the kitchen. His dress and apron twirled beautifully as he did so. A few moments later he appeared with a plate of biscuits.
“Thanks dear. You can go back to your dusting now. Almost done?” Joe frowned. “Still to do upstairs.” He turned and went back to the house. When he went back in the door, his mother and granny looked at each other in their deckchairs. “Cheers!” they tittered as they raised their cups.
-
Poor Joe! A seemingly endless supply of little girl party dresses and matching rumba panties. This is too coincidental to not be planned by his mother. Wonder if Barry's mother will meet Joe's mother and be filled in on the benefits of Joe's petticoating and the positive effects on his home school work. One could only hope. ;D
-
DaraJaney, Joe is learning that his school work will be better in a school uniform. He hates the uniform; but, he hates the little girl dresses and rhumba panties more. He is learning that a girl's life is no bed of roses. His mom and his granny have this all planned out and he sees no way out of his predicament.
Great Chapter, DaraJaney. Can't wait for more. :P :P :P :P :P :P :P :P :P
-
He's becoming so well-trained so fast! Delightful
-
Andlat, you're right, Joe or Josephine has become well trained, although, he hates the dresses, rhumba panties and his school uniform. His mom and granny just love seeing him in his juvenile dresses. Jenny and Barry love seeing the big kid in those little girl outfits.
-
It became clear that the lockdown could last months. Joe’s mother stoutly refused to buy any boy’s clothes for him saying that there were perfectly good clothes available for him to wear and in any case, she kept reminding him, if he went out and about in boy’s clothes then Barry, Jenny and everyone else in the neighbourhood would know that he had been a boy wearing dresses, tights and rumba panties for the last few weeks. Did he really want that? That usually shut him up and left him fiddling with his apron disconsolately.
Easter came around. His mother tried to cheer him up, reminding him that he would receive his usual Easter gift of a dozen chocolate ‘crème’ eggs which he preferred to the traditional large Easter egg.
On Easter Sunday morning his granny selected the pink and blue floral dress with the petticoat for him to wear. “This was your Easter dress one year wasn’t it?”, she reminded his mum. “Oh yes! Well, not just the dress though.”
She reached up to the top shelf of the wardrobe and took down a white bag closed with a drawstring. Joe watched as he pulled on his lacey white tights. She untied the knot and reached into the bag. He pulled his pink rumba panties up under his dress. She took out a multi-layered petticoat. “I wore this under my dress each Easter Sunday!” She fluffed out the petticoats and brought them over to Joe.
Joe winced but she held the petticoats down for him to step into. Then she pulled them up under his dress and tied them around his waist. His granny smoothed his full skirt over the petticoats. “Gorgeous!”
Joe moved over to the mirror feeling the weight of the layers of petticoats rocking around him as he walked. He had thought that the single petticoat attached to his dress had made it stand out quite enough but the effect of the multi-layered petticoats was dramatic. For one thing it meant that the dress revealed much more of his legs in his lacey tights. The hem only came half way to his knees. He tried to push the petticoats down but the organza layers just sprang back up into their insistent poufiness.
Getting all his petticoats under his bottom as he sat at the breakfast table was his first problem. He found that he had to be very conscious of the wide breadth of his dress. He could easily knock a precious vase over if he wasn’t careful.
He was removing his apron after washing the dishes when his mother announced “we’ve arranged a little game with Jenny”. She turned to his granny. “Do you remember we used to have Easter egg hunts?” “Oh yes!” His mother turned to him again. “So your 12 crème eggs are hidden around the garden.” She handed him a wicker basket. Joe sighed heavily. “Jenny’s mum has hidden the same in her garden so you can have a race.”
He was ushered out into the garden with his basket in the crook of his arm and he tried to steady his petticoats in the breeze. Jenny and her mum were already in their garden. He winced to see that Jenny was in trousers even on Easter Sunday. She and her mother smiled at Joe’s petticoats but it was clear they were trying not to laugh. “Oh how pretty!” His mother looked on proudly. “Give us a twirl love!” Joe tried to smile through it. He gave a twirl which he immediately thought had been too energetic and wondered if he had flashed his rumba panties as his petticoats whirled up.
“Now go find your eggs! You can’t eat any until you have found all twelve.” Jenny ran immediately towards a couple of eggs that were clearly visible in the grass. Joe could see a few in his garden but had to walk more carefully in his petticoats. His mother held up a camera and started recording.
When Joe reached the first few eggs he carefully bent his knees, lowered himself slowly so as not to cause his petticoats to parachute out too much. He was quite pleased with his decorum. But now he had to find the eggs that had been better concealed.
He saw one up in the branches of a tree. He approached it. He could see that Barry was now watching from his garden. Joe reached up carefully hoping that his dress wouldn’t ride up enough to expose any of his rumba panties. But he was still a few inches short. He could see that Jenny was quickly rushing around the garden collecting her eggs with no difficulty.
He had to collect all twelve so he had to jump to try to reach it. His first attempt was half hearted but even so he could feel the wind resistance as his petticoats parachuted on descent. He quickly smoothed his skirt down. There was an obvious smirk on Barry’s face. Joe cringed. He had to get that damn egg and quickly. He jumped higher and grabbed the egg. He had felt his petticoats puff up around his chest as he descended and there was really no doubt what everyone had seen.
He found the next five eggs easily enough and eventually spotted three in a row behind a low box hedge. As he approached, he wondered how he was going to reach them without further humiliation. There was no way to get them other than to bend over the hedge. Jenny ran up to her mother “Twelve!” she shouted.
All eyes were now on Joe. He sighed heavily. He had to get it over with. He bent over the hedge to reach the first egg. The front of his petticoats tipped downwards towards his ankles. He could only imagine how far the back tipped up.
He had to repeat it twice to get the last eggs. He could feel his cheeks burning as he turned around to face everyone. His mother still had the camera on him.
Barry’s mother emerged into their garden. “Barry what were you doing?” Barry turned towards her in shock. His cheeks were now burning. “Were you spying on that girl?” she demanded to know. Barry just stuttered. He knew he’d been found out spying on the girl next door and her frilly undies.
His mother saw the others. She introduced herself. “Sorry we haven’t met, I’ve been really busy at the hospital”, she explained. Then she turned to Barry again. “Apologise to the girl for spying on her.” Joe started to smirk a little, relishing Barry’s embarrassment at having been caught spying on him to see his rumba panties.
“No really it’s not Barry’s fault”, his mother interjected. “Josephine here is very inexperienced in wearing dresses and really must stop exposing her panties so often!” Joe’s jaw dropped as all eyes were now on him.
“Josephine. You must apologise to Barry for exposing your rumba panties to full view.” Joe felt sick. He could see his mother was determined. She crossed her arms firmly.
“I …. I’m sorry for … showing my rumba panties”, he managed to utter while staring at the ground. Barry had the biggest smirk ever. Everyone seemed to be satisfied though.
“Why don’t you show us all your skipping”, his granny suggested. Joe pushed his petticoats down instinctively. Really? In these short petticoats? After what’s just been said?
But there was no disappointing people. His mother handed him the rope and Joe obediently skipped in front of everyone and there was no doubt from his fluttering petticoats and from where everyone was looking that he was putting on a good show again. His mother’s camera was rolling again.
In the end, the rope got caught on his petticoats. He tugged at it frustratedly. “You really aren’t used at all to wearing petticoats are you?” his mother observed. “Well it’s the school holidays now so you can wear petticoats under your dresses every day instead of your uniform so you can get more used to them.” Joe tried not to look too despondent as he resumed his skipping.
“Mother, are the other five pairs of rumba panties freshly laundered?” she asked his granny. “Oh yes, they’re all in her drawer.” Joe cringed.
-
Well a twist that Joe’s mother could suggest to Barry’s mother could be if Barry likes looking at rumba panties and frilly dresses so much maybe she should get him some for himself since Joes mom has observed Barry looking since the beginning
-
Like SissyBraelyn, my big takeaway is the potential developments in regards to Barry. I'm a bit conflicted though. While misery loves company, I also enjoy the idea that Barry is looking at another boy's frilly underthings without even knowing it's another boy. As always, I put my trust in the author.
-
DaraJaney, that was a fantastic chapter. Josephine had to wear that flowery dress with those poufy petticoats and he hates it. The Easter Egg race was priceless as Josephine had to bend, reach and jump in order to find all of his chocolate eggs.
Barry got an eyeful of Josephine's rhumba panties and he also got caught looking. Maybe his mom will, with Josephine's mom and granny's help, put Barry in petticoats, dresses and rhumba panties. One can only guess.
:-X
-
Joe was even more mortified having to wear the multi-layered petticoats under his dresses all week. He knew it would make skipping – his main form of exercise – even more embarrassing. And his neighbour Barry was in his garden nearly all the time just waiting for a cheap thrill.
Joe’s mother came out. “Why aren’t you skipping dear? You need the exercise.” Joe sighed heavily and glanced at Barry who had clearly perked up next door. His mother handed him the rope. Joe had to think of something else to do quickly – something she would agree to.
“Can I play with the dolls instead?” He almost threw up as soon as he’d said it. His mother was clearly pleasantly surprised. “Of course dear.” So Joe went to the boxes and picked up a doll, cringing as he tried to think what he was supposed to do with it. He went over to the garden seat and tried to arrange his petticoats beneath him with one hand as he clutched his doll with the other.
His mother placed the box of doll’s clothes beside him. “There you are. I think she’d look pretty in that cerise dress!” He looked into the box. Cerise? What the f*** was cerise? He could see that Barry was losing interest – throwing his eyes up at the sissy girl playing with dolls.
Joe consoled himself that sitting on the garden seat in his yellow dress, petticoats and white tights playing with dolls was marginally better than skipping and showing off his yellow rumba panties.
He finished dressing the doll and placed it beside him on the seat. He chose another doll and outfit. His mother was watching from the kitchen window so he had to keep playing with the dolls or there was a danger she’d insist that he skip again.
When she next came out next, he had three dolls lined up beside him on the seat. “You should have a tea party!” she suggested, pointing to the plastic toy tea set in another box. Again, Joe felt sick at the thought of having a pretend tea party with his dolls in his yellow dress and petticoats. He stayed where he was.
“Why don’t you get that nice doll on the display cabinet in the dining room?” his mother suggested as she passed back. “That peach dress fits her as far as I recall.” Joe looked in the box. Peach? What the hell did peach look like?
Anyway, he reckoned it got him out of Barry’s view for a few moments. He stood up and carefully arranged his petticoats around him before walking back into the house. He went into the dining room and saw the doll on the lower shelf of the display cabinet.
He went over, bent down and picked it up. He turned clutching the doll and froze as he heard “Hello!” and then a very surprised “Who’s that?!” His granny was in a Zoom meeting with her three sisters – Agnes, Kate and Peg.
“Oh, sorry I didn’t tell you”, his granny responded. Joe could see the screen on her computer. Her sisters were looking intensely at their screens. He could see his granny’s quarter of the Zoom meeting. She was leaning back and he was clearly visible in his yellow dress, full petticoats and white tights, his pigtails tied with yellow ribbons and now he was clutching a large doll.
“Come here Joe”, his granny beckoned. He was horrified at her reveal. “Joe?!!!” he heard in unison from his great aunts. He moved disconsolately towards the screen. “Doesn’t he make a pretty girl?” “I LOVE the matching rumba panties!”, Agnes giggled. Joe cringed. Why hadn’t he been more careful picking up the doll? Ugh! The doll!
He could see the amazed, giggling, tittering faces on the other three screens as his granny explained how he’d had no choice but to wear dresses and was now playing in the garden every day in front of the other children in his pretty dresses. He’d even been to the shops to buy those rumba panties.
“I bet you love wearing those white tights!” Kate teased. “Oh, why don’t you put on those pretty lace patterned tights for them?” his granny suggested. Kate squealed with laughter as Joe stood mortified. “You look so pretty in your petticoats and pigtails”, Peg added.
“What’s your dolly’s name?” Agnes persisted. His granny whispered ‘Abigail’ to him. “Abigail” Joe told them. “Is she your favourite?” He sighed. “I remember the box of dolls there”, Peg recalled. “Which one is your favourite?” Joe wasn’t taking the bait.
“We must send you the video of Easter Sunday”, his granny told them. Joe was horrified. “We had an Easter Egg hunt. He was wearing his mum’s floral Easter dress with those petticoats, his lace-pattered tights and pink rumba panties. Wait until you see him skipping!” His grand aunts’ jaws dropped simultaneously. “Oh do send it. I can’t wait to see that!”
Eventually Joe squirmed away from the screen and took his doll outside. After another hour of dressing his dolls his mother suggested that he needed to do some vacuuming. It was that or skipping he reckoned.
She was pleased that his extensive apron fitted nicely over his dress even poufed out with his petticoats. They called on him to bring them tea in the garden when he was half way through vacuuming.
As he brought the tray out the wind caught his petticoats. He was clutching the tray and could do nothing to stop his petticoats whirling up around him. He placed the tray on the table and turned to go back. He was met by the broad grin of Barry staring though the fence. Despite all Joe’s efforts he’d clearly got what he’d been hoping for.
-
DaraJaney, You have a way with words. Between the embarrassment if skipping in front of Barry, having to play with dolls or displaying his rhumba panties to his great aunts, Joe has felt it all. In the end, Joe is doing the vacuuming when he has to serve tea to his mom and granny. Of course, Barry got to see Joe's white, tight covered bottom. Fun. 8) 8)
-
Things never seem to get better for the protagonist when more people find out about his frilly predicament, so this can't end well for Joe. I imagine much more domesticity and many more pretty dresses in his future.
-
As the weeks passed Joe’s hair grew longer and it was starting to be difficult to get his wig of pigtails to stay in place. His mother and granny considered the situation. Neither felt competent to cut his hair. They had no experience at styling hair either, being totally dependent on their local salons which were, of course, closed.
One Sunday morning his granny said “there’s only one thing I can think of. Remember when you were little?” His mother thought about it. “Oh, have you still got that?” His granny went to rummage in the attic.
His mother washed his hair and sat him down in the dining room. She rubbed smelly lotions into his hair. His granny came up behind him and started tugging his hair. It felt like she was wrapping it around something. His mother joined in and soon his full mop of hair was tightly wound around in dozens of places.
He heard his granny plug something in behind him and then he felt his hair heating up. His mother sprayed lots more stinky stuff over his head and then placed a plastic thing like a shower cap over the hair.
“Just a couple of hours”, she told him. Joe was surprised. Hours? What was he to do? He tried to stand up. “Ow!” His hair had been tugged all over. He had no choice but to sit in the chair as his hair was attached to whatever was plugged in at the wall. His mother fetched the box of dolls and dolls’ clothes. He sighed. He really didn’t want to play dress up with his dolls again but after twenty minutes of boredom he gave in and started unbuttoning the dress on one of the dolls.
Eventually they came, turned off the switch at the socket and took the cap off. They started undoing what they had done – his granny working at the back and his mother from the front. A couple of tight curls dangled above his eyes. He looked at them dubiously. Was his whole head of hair going to be like that?! There was no mirror. He was still confined to the chair as long as his hair was attached to the socket in the wall. He just had to sit there in his pink Sunday dress, petticoats and lacey tights, clutching the doll he’d just finished dressing.
As his granny continued at the back his mother started tying two pink ribbons in his hair. Then she left the room. She returned with the laptop which she placed on the dining table a few yards in front of Joe. “Time for the first extended family Zoom meeting!” she announced.
Joe’s jaw dropped. He saw the Zoom app loading. He was in the direct line of the webcam. He tried to get up and leave. “Ow!” He was still attached to a couple of pins and had to flop back on the chair. He looked on in horror as his mother clicked “Join meeting”. All of his relatives popped up on the screen. Then he saw his own webcam’s image. He was sitting there is his pink Sunday dress for all to see. His hair was now a mass of ringlets, two bunches tied up with big stiff pink ribbons tied in bows. His layers of petticoats rested on his knees and his flowery patterned lace tights were clearly visible. And he was clutching the damn doll!
His mother and granny sat down closely either side of him. He was stuck in the seat and couldn’t get rid of the stupid doll. He could hear the laughter increasing from his extended family. “I’d heard about it from Agnes! But I couldn’t believe Joe was wearing pretty dresses and playing with dolls!” “You mean Josephine!” his mother corrected her, smiling at her mortified son in his pretty dress.
“Is he wearing those pretty pink rumba panties?” Kate asked. Joe instinctively pushed his petticoats down and they all knew that was confirmation that he was wearing said panties. They burst out laughing.
“Stand up and give them a twirl sweetie”, his granny urged him. She ran her fingers through his ringlets at the back to show him that she had discretely freed them from the heated pins. It now looked like he had been happily sitting there while they started the Zoom meeting to reveal him to the whole extended family in his pretty clothes.
He stood up and his mother and granny pushed his elbows to make him twirl. When he had his back to the camera he felt his mother pull his petticoats up at the back and there were screams of laughter at his pink rumba panties.
He sat down again quickly but just had to stew there is his petticoats and tights, clutching his doll miserably while the Zoom meeting continued. Nobody else seemed to want it to end. He looked at his full head of ringlets and wondered how long they would last.
The conversation eventually sagged and he wondered if the meeting would finally end. “Time for the quiz!” Peg announced. Everyone else perked up but Joe sagged in his pink Sunday dress. “Round 1 of 20!” Joe cringed.
When the interminable quiz reached its last round, his mother smiled at his ringlets. “You’re going to look so cute now when you are skipping”, she told him. “Skipping?” a number of relatives shouted into their mics. “Oh let’s see!”
Joe was ushered out into the back garden. His mother handed him the skipping rope while his granny positioned the laptop on the patio table. Jenny was next door. “Oh what cute ringlets!” Barry was inevitably on the other side.
“OK this is the finale to our meeting” his mother announced. Joe was cringing. At least this would make it end. He tried to push his petticoats down as a far as he could before he swung the rope over his head and jumped.
His petticoats whirled and his full head of ringlets danced – except for those tied up with pink ribbons. He could hear laughter and clapping coming from the laptop. “Count to one hundred!” his mother urged them. Joe grimaced at her but his relatives were all counting and he had no choice but to continue skipping as they counted. He could see from Jenny and Barry’s eyeline that his pink rumba panties were putting in an appearance.
When he finally reached one hundred they all cheered. He desperately tried to smooth down his petticoats and felt his ringlets, thinking they must be all in disarray. But they were all still dangling stiffly from his scalp.
“See you all next week!” his mother told the meeting. Joe sighed heavily. “You must practice more skipping tricks for next week’s meeting”, his mother told him. “You can wear your Easter dress again and we’ll renew your ringlets every Sunday before the get-togethers. “Looks like this lockdown is going to go on and on.”
-
DaraJaney, Josephine really hates his ringlets. This lockdown is really a pain for him/her. The dress, rhumba panties and ringlets were a great look for the Zoom Meeting. Can't wait to see what his Granny and Mom come up with. ;)
-
At a certain point, Joe has to come to the realization he's become his mom and granny's primary source of lockdown entertainment. They've clearly gone beyond what's necessary to keep him clothed, not that I mind one bit. Almost makes me wonder if some poor boy somewhere in lockdown is getting a (admittedly less extreme) version of this in real life. It's a very large world we live in!
-
Poor Joe(sephine). Nothing but fancy dresses, voluminous petticoats, rhumba panties, tights and mary janes and no end in sight. No mention of Mom lacking clothing causing one to wonder if this really was a setup to tame Joe. As others have pondered, can't imagine Barry's "interest" in Joe's clothing escaping his mother's attention. Can't see Barry escaping a good petticoating since he's been scolded time and again about gaping at Josephine's cute undies. Jenny may provoke the issues due to some prior offense by Barry.
Glad you're continuing the story. It was so unlike you to leave such a large time gap between chapters. Was honestly concerned that you may have been unwell.
-
When news came through that the lockdown was to be eased and people could travel further distances again, Joe asked if they would be able to move home so that his nightmare of having to dress and act like a sissy girl could end.
“No we must stay here and take care of your poor granny, mustn’t we?” Joe fiddled frustratedly with the frills on his apron. “Well, can we just go and get some of my proper clothes?” he pleaded. “Don’t be silly! You don’t want everyone in the neighbourhood to know that you are a boy who’s been wearing pretty girl’s clothes for the last few months do you?” She fluffed up his petticoats while Joe sighed, realising that he would be teased endlessly about his frilly panties and lacey tights.
“Now it’s an hour til bedtime you’d better start tying up your ringlets so they’ll still be nice and bouncy in the morning.” “Yes mother.” As if it wasn’t humiliating enough having his hair in ringlets, it took so much work – tying up each individual ringlet in pink ribbons every night and untying them in the morning, while sitting in front of the mirror in his pretty dress.
As people could now meet outdoors, his granny had the idea of inviting one of her friends over for tea in the garden. Mrs Winstone had been on her own through the whole lockdown and his granny was worried that she was quietly going mad. She was rather posh which was the one thing that his granny couldn’t stand about her. She even used to have a maid but in recent years was unable to retain anyone who would meet her high standards and demands.
As his granny and mother were discussing this, Joe came out with their tray of tea. His granny smiled as the lace trim on his apron fluttered and his petticoats swayed as he walked. “You know what would be really funny?” she mused. “If Mrs Winstone thought that we had a maid! She would be so jealous.” They laughed at the idea.
Joe agreed to go along with the prank. He was spending more and more time in his apron doing chores around the house and bringing them tea anyway.
In the days leading up to the visit, some parcels arrived. Joe hadn’t paid much attention - they were getting lots of deliveries since they couldn’t go out shopping.
Two days before Mrs Winstone was to come, his granny and mother came into his bedroom in the morning with some of the boxes. His mother took a black dress out of one of the boxes and hung it on the back of the door. It was a maid’s uniform, black with white lace collar and trim on the sleeves and hem. “What the ….?” Didn’t he look enough like a maid in his apron, he thought? Apparently not.
He got out of the bed and they got him to take off his nightie. His granny opened another box and removed a pair of small silicone breasts! Joe’s jaw dropped. “We want you to show a nice shape in your uniform.” The breasts were on bra-like straps and they quickly adjusted them to give him nice little boobs.
While Joe was somewhat mesmerised by his new acquisition, his mother held up a particularly large pair of knickers. She made him step into them and when she pulled them up, he realised that there were thick pads in the bottom and over the hips. Next was a basque with waist clincher and bra cups. His mother hooked him up at the back and the stiff wire under the bra cups presented his new little boobs nicely.
Joe noticed four straps dangling from the basque. He examined them and when he looked up, his mother was rolling up a black stocking. Once his stockings were attached to the suspender straps his granny took the maid’s dress, threw it over his head and zipped it up. Immediately his mother took one of his petticoats, made him step into it, pulled it up under his uniform and tied it in place at his higher, narrower waist. Then they produced a full white apron, tied it around his waist on a big bow and settled the frilly starched straps over his shoulders.
“Now for your make-up!” Joe emitted regular protests and yelped occasionally when something hurt but there was no stopping the two women on their mission. They applied foundation, drew dark eye-brows, eye-liner and eye-shadow before gluing on false eye-lashes and thickening them with mascara. They drew thick red lips with the stick and powdered some blush on his cheeks.
They placed a lacey headband into his ringlets and gave him white gloves which had lace trim at the wrists. Finally his mother took a pair of black high-heels from another box. She strapped them on and they pulled him to his feet. He stumbled in the four-inch heels. They made him wobble across the room. “I can’t walk in these!” he protested. “Don’t worry”, his mother smiled. “You have a couple of days to practice and get used to them.”
Joe looked in the mirror. At least his maid’s uniform came almost to his knees. He stood sideways to appreciate the little boobs pressing through the bib of his apron. His petticoats stood out perkily over his padded bottom and hips. “Now!” his granny declared. “Time for you to make our breakfast!” Joe sighed heavily.
-
Oh, dear! Barry might just faint if he sees Joe in his maid outfit!
-
DaraJaney, Poor Josephine. Now he has to play maid for his mom and granny. The next part of this story should be real interesting. Mrs Winstone is going to be surprised by the maid that his granny has.
GREAT story chapter. More please. 8) 8) 8) 8) 8) 8) 8) 8) 8) 8) 8)
-
When news came through that the lockdown was to be eased and people could travel further distances again, Joe asked if they would be able to move home so that his nightmare of having to dress and act like a sissy girl could end.
“No we must stay here and take care of your poor granny, mustn’t we?” Joe fiddled frustratedly with the frills on his apron. “Well, can we just go and get some of my proper clothes?” he pleaded. “Don’t be silly! You don’t want everyone in the neighbourhood to know that you are a boy who’s been wearing pretty girl’s clothes for the last few months do you?” She fluffed up his petticoats while Joe sighed, realising that he would be teased endlessly about his frilly panties and lacey tights.
“Now it’s an hour til bedtime you’d better start tying up your ringlets so they’ll still be nice and bouncy in the morning.” “Yes mother.” As if it wasn’t humiliating enough having his hair in ringlets, it took so much work – tying up each individual ringlet in pink ribbons every night and untying them in the morning, while sitting in front of the mirror in his pretty dress.
As people could now meet outdoors, his granny had the idea of inviting one of her friends over for tea in the garden. Mrs Winstone had been on her own through the whole lockdown and his granny was worried that she was quietly going mad. She was rather posh which was the one thing that his granny couldn’t stand about her. She even used to have a maid but in recent years was unable to retain anyone who would meet her high standards and demands.
As his granny and mother were discussing this, Joe came out with their tray of tea. His granny smiled as the lace trim on his apron fluttered and his petticoats swayed as he walked. “You know what would be really funny?” she mused. “If Mrs Winstone thought that we had a maid! She would be so jealous.” They laughed at the idea.
Joe agreed to go along with the prank. He was spending more and more time in his apron doing chores around the house and bringing them tea anyway.
In the days leading up to the visit, some parcels arrived. Joe hadn’t paid much attention - they were getting lots of deliveries since they couldn’t go out shopping.
Two days before Mrs Winstone was to come, his granny and mother came into his bedroom in the morning with some of the boxes. His mother took a black dress out of one of the boxes and hung it on the back of the door. It was a maid’s uniform, black with white lace collar and trim on the sleeves and hem. “What the ….?” Didn’t he look enough like a maid in his apron, he thought? Apparently not.
He got out of the bed and they got him to take off his nightie. His granny opened another box and removed a pair of small silicone breasts! Joe’s jaw dropped. “We want you to show a nice shape in your uniform.” The breasts were on bra-like straps and they quickly adjusted them to give him nice little boobs.
While Joe was somewhat mesmerised by his new acquisition, his mother held up a particularly large pair of knickers. She made him step into them and when she pulled them up, he realised that there were thick pads in the bottom and over the hips. Next was a basque with waist clincher and bra cups. His mother hooked him up at the back and the stiff wire under the bra cups presented his new little boobs nicely.
Joe noticed four straps dangling from the basque. He examined them and when he looked up, his mother was rolling up a black stocking. Once his stockings were attached to the suspender straps his granny took the maid’s dress, threw it over his head and zipped it up. Immediately his mother took one of his petticoats, made him step into it, pulled it up under his uniform and tied it in place at his higher, narrower waist. Then they produced a full white apron, tied it around his waist on a big bow and settled the frilly starched straps over his shoulders.
“Now for your make-up!” Joe emitted regular protests and yelped occasionally when something hurt but there was no stopping the two women on their mission. They applied foundation, drew dark eye-brows, eye-liner and eye-shadow before gluing on false eye-lashes and thickening them with mascara. They drew thick red lips with the stick and powdered some blush on his cheeks.
They placed a lacey headband into his ringlets and gave him white gloves which had lace trim at the wrists. Finally his mother took a pair of black high-heels from another box. She strapped them on and they pulled him to his feet. He stumbled in the four-inch heels. They made him wobble across the room. “I can’t walk in these!” he protested. “Don’t worry”, his mother smiled. “You have a couple of days to practice and get used to them.”
Joe looked in the mirror. At least his maid’s uniform came almost to his knees. He stood sideways to appreciate the little boobs pressing through the bib of his apron. His petticoats stood out perkily over his padded bottom and hips. “Now!” his granny declared. “Time for you to make our breakfast!” Joe sighed heavily.
<>
So Joe spent two days in the maid’s uniform and full make-up, mostly training to walk convincingly in the four-inch heels. His mother insisted that immersion was the only way. No pain, no gain. The quickest way to get used to high-heels was to wear them all day every day.
When it came to the time for Mrs Winstone to arrive his granny and mother fussed over his uniform – fluffing out the frilly lace over his shoulders, poufing out his petticoats, settling the bow at the back of his apron and renewing his lipstick and rouge.
Mrs Winstone was invited to go down the side passage of the house into the garden where she sat socially distanced from his granny and mother. They smiled knowing she was quite unsuspecting.
They had placed a bell on the patio table. His granny reached forward and rang it. Mrs Winstone was clearly puzzled. The back door opened and Joe flounced out in his maid’s uniform. He tried to maintain a pleasant demeanour as he walked across the patio in his now familiar high-heels, his hands resting lightly on his petticoats, ensuring that they wouldn’t be ruffled too much by any sudden gusts.
His granny and mother savoured the look on Mrs Winstone’s face as she watched this maid in full uniform approach. “Tea for three please Josephine.” “Yes Ma’am” Joe replied as trained. He was about to whirl around to get out of there as quickly as possible but remembered that he would be in danger of exposing his stocking tops if he did that so he maintained a dignified slow turn and walked back to the house.
Barry was in his garden as ever. His jaw appeared to have hit the ground. Joe did his best to maintain a composed look – as much as he could in a maid’s uniform with petticoats, full frilly apron, black stockings and suspenders, high heels, full make-up and fluttering eye-lashes.
Needless to say, Mrs Winstone was bursting to ask how they managed to have a well-turned out maid but didn’t want to acknowledge that they had something she couldn’t get. So she acted as if this was reasonably normal.
Joe served them tea and cakes and returned to clear the table when summoned with the bell. His mother decided to put Mrs Winstone out of her misery. In reality they didn’t want people to think they actually had a servant.
“Josephine here is in training. We agreed to take her for a couple of months and then the lockdown happened.” They could see the relief in Mrs Winstone as she readily believed the story. “Well I’d be very happy to take her on for a training period and could pay well”, she responded.
His mother and granny were surprised at this turn of events. Joe continued to gather the plates. “That’s an interesting proposition”, his mother said when she thought about it. Joe froze. “Why don’t you bring her over next week and we’ll see how it goes?” Mrs Winstone decided to strike while the iron was hot. “Let’s do that”, his granny agreed before Joe was in a position to raise any objections. He tried not to show his distress.
Joe’s objections were easily dismissed afterwards. A simple threat to share photos and videos with his friends back home silenced him. The idea of them seeing him skipping and playing with dolls in his Easter dress with full petticoats, lacey tights, rumba panties and ringlets was enough to strike terror in him.
The only relief for him was that they obtained a more normal and practical maid’s uniform for him – white trim but not lacey, no petticoats and sensible heels. He still had to wear the shaping garments to give him a convincing figure and some make-up.
But when they presented him at Mrs Winstone’s she clearly wasn’t happy. “What’s this? Where is her proper uniform?” His mother responded “that was her uniform for special occasions – like your visit”. She hoped that flattery might help.
“No, no, no!” Mrs Winstone insisted. “Bring her back in the proper uniform and we’ll talk. I can provide a special uniform for occasions.”
So they returned the following day with Joe in his lace-trimmed uniform, petticoats and high-heels, fully made-up with fluttering eyelashes. “That’s more acceptable”, Mrs Winstone agreed.
“Here is my standard contract. Six-month training period followed by a commitment to two-years after that”, she stated firmly. “Six months and two years?” his mother was taken aback. Joe tried not to fall over at the thought but was reassured by his mother’s surprise.
“I put a lot of effort into the six-months of training” Mrs Winstone insisted. “I need to be assured that she won’t simply walk off into another job.” “I see your point”, his mother responded. Joe tried to give her an insistent look that she couldn’t possibly agree to that.
“Very well”, his mother took the contract and signed it before he could demur. Joe nearly fell over. Two and a half years in petticoats, stockings and high heels!
His mother stood up. Mrs Winstone was smiling. “Why don’t you come back in a month and see how she’s getting on?” A month before there was any chance of release! “Marvellous, we’ll see you then.” His mother smiled at Joe, taking in another sweep of his outfit from his lacey headpiece and ringlets, down his frilly apron, petticoated skirt, black stockings and high heels. His wide-eyed look of desperation was really set off nicely by his long false-eyelashes.
-
Poor boy. This is terrible.
-
DaraJaney, Josephine is in a world of hurt and embarrassment with his new position as Mrs. Winstone's maid. She is going to put him through maid training like he has never imagined. I really feel sorry for him, NOT!!
Great chapter. Keep them coming. 8)
-
A month later, Joe’s granny and mother arrived at Mrs Winstone’s eager to see how his first month of training as a maid had gone. The door opened to reveal that she had delivered on her promise to obtain a new uniform for special occasions.
Joe squirmed in his bright pink uniform. The snow white full apron gleamed with thick lace trim and stiff upright lace on both sides of the shoulder straps. His new dress was much shorter and there must have been at least seven layers of petticoats.
He had long pink false nails, revealed prettily by fingerless white gloves which had delicate lace around the end of each finger and two-inch lace at the cuffs. Their eyes continued down to his white lace-patterned hosiery and his feet wedged into pink sandals with heels that must have been five-inches. Pink painted toes could be seen through the white nylon.
He knew he was being studied and stood self-consciously fluttering his long false-eyelashed. Pink eye-shadow flashed every time he blinked. Was that rather a lot of blush or was it natural?
“May I take your coats”, Joe squeaked in his new posh voice. He sighed obviously, seeing that they were really pleased with his new look. He turned to put their coats in the closet. They could now see the black seam running down the backs of his legs to a Cuban heel. His dress and petticoats must have been made with some extra light material because they fluttered madly as he tottered along in tiny steps forced on him by the higher heels. The black tops of his stockings could now be glimpsed.
Having taken care of the coats he said “Follow me please” and headed for the reception room. He was now so tall in his heels that he had to bend a little to turn the door handle. They could now see his pink pettipants, the lower frills of which came almost to the tops of his stockings.
His mother wondered why he had kept up such an embarrassingly mincing walk with his hands delicately floating out from his body, hovering above his layers of petticoats when Mrs Winstone wasn’t even around to see it. She seemed to have trained him well so far.
Mrs Winstone welcomed them and invited them to sit. “Josephine! Three teas please and those nice cakes.” Joe curtsied! They could now see as he held out his petticoats that the alternate layers were pink and white. They watched and smiled as he scampered to the door, giving them that lovely flash of pink pettipants again as he reached for the handle.
They were surprised to see a small laptop on the table beside Mrs Winstone’s chair. She turned the screen towards them. “I had security cameras installed in each room last year. They are motion-activated and perfect for keeping an eye on the maid.”
They could see Joe scamper across the hallway and it was obvious now why he had to keep up his exaggerated mincing walk all the time. The screen switched to a camera at the bottom of the stairs down to the kitchen.
The angle gave a wonderful view of his madly fluttering petticoats as he descended, clutching the banister with one hand as he tried his best to control his petticoats with the other. Considering that he mustn’t be able to see the steps below his billowing petticoats and the fact that he was wearing five-inch heels, they thought he managed particularly well.
Mrs Winstone updated them on progress. “She is coming along adequately”, she pronounced. “As you can see her deportment still needs a lot of work.” His granny and mother nodded, though they had been astonished at his competence in walking in the five-inch heels and wondered exactly what another five-months of intensive training could do.
Mrs Winstone frowned at the laptop screen. She reached for the mouse. “Josephine!” They saw Joe jump in surprise and look up at the kitchen camera. “Why are you dawdling?” “Oh, I’m waiting for the kettle to boil Ma’am.” “I’m sure there are some worktops you could wipe down or something else useful. Don’t stand about.” “Yes Ma’am”, he curtsied to the camera. “I mean no Ma'am”. He scampered across the kitchen, grabbed some tissues and started wiping down the work-top. His granny and mother smiled at each other.
Joe eventually arrived with the tray of tea and cakes. He did his best to bend his knees while placing it on the coffee table but his ultra-light petticoats inevitably fluttered to reveal a couple more rows of his pink pettipants and his suspender straps straining at the tops of his stockings.
“You may resume cleaning the upstairs rooms”, Mrs Winstone ordered. Joe curtsied and tottered off out of the room. As they chatted they kept an eye on the laptop screen which followed Joe scampering up the staircase and into a bedroom where an old-fashioned heavy vacuum cleaner was waiting.
But first he picked up a feather duster. He minced around the room in his five-inch heels, dusting the furniture and reaching right up into the corners including the corner with the camera, giving them a lovely close-up view of his fluttering eyelashes.
Mrs Winstone glanced regularly at the screen which explained why Joe did such a thorough job of the dusting. They were impressed. She reached for the mouse again. A bell rang. Joe jumped a little again, put down his feather duster and scampered urgently towards the door.
They could see the seconds being counted on the laptop screen. They reached 35 by the time Joe entered the room. He scampered over and curtsied “Yes Ma’am?” “Thirty five is not good enough! You really need to make it in 30 seconds.” Joe looked at the floor. He clearly wanted to explain that it was impossible to go any faster in the five-inch heels but he held his tongue. “Sorry Ma’am.”
“Would you like anything else?”, she asked her guests. “More tea?” They were surprised. Joe looked to them anxiously, clearly ready to jump to it and satisfy whatever request they made. “No thanks.” They didn’t want to make things harder for him.
“Very well, you may return to your work”, she told Joe. He was clearly frustrated at being made to come all the way down for nothing but again just curtsied and said “Thank you Ma’am.”
When he returned to the room he started vacuuming. They watched with fascination as he hauled the heavy machine around the room in his five-inch heels, his free hand held out daintily while he directed the nozzle across the floor. He had to stop the vacuum cleaner regularly to move chairs about and once again they were impressed that he left no corner untouched.
About thirty minutes later, he was summoned again. “You may take your 15-minute break now and speak with your mother and grandmother”, she told him. “You may make another round of tea for your break.” Joe curtsied and scampered off to the kitchen. His mother smiled as she watched him dust the cupboard handles while the kettle boiled, glancing nervously at the camera.
When he appeared with the tray Mrs Winstone stood up. “I’ll leave you to talk.” She left the room. Joe sat in a low chair and had to shuffle a couple of times to rearrange his vast layers of petticoats into some kind of order. His high heels forced his knees high and there was nothing he could do to prevent the exposure of stocking top and suspender strap. He was clearly relieved to take the weight off his heels though.
“So how are you doing?”, his mother asked. Joe looked at the camera suspiciously. Mrs Winstone had taken the laptop. She was probably listening in. He had five-months training left and two years as a fully-trained maid after that. He didn’t need to annoy her.
“Fine”, he responded – hoping that his minimalist answer would be interpreted correctly. “Do you like your pretty new uniform?” Joe maintained a fixed smile while he said “Yes.” “It must be quite difficult vacuuming in those heels.” There was a pause before he said “it’s fine.” “So is Mrs Winstone treating you well?” Again, a glance at the camera, “Yes.”
“Would you say that she is strict but fair”, his granny pressed him. “Yes, that’s right”, he was forced to respond. “That’s good”, his granny smiled. The stilted conversation continued for the 15 minutes, only making him feel more trapped.
As he saw them off his mother tittered “only another 17 months to go!” Joe glared at her. “I’m sure she’ll be keen to keep you on indefinitely after that”, his granny added. “I’m mean, what else will you be able to do at that stage anyway?” Joe’s face fell as the idea of him being a maid permanently formed.
The next morning he was quietly relieved to be back in his normal maid’s uniform, the few layers of petticoats coming almost to his knees. He raised his petticoats to check his suspender straps. At least he didn’t have to worry about any stupid seams. His black and white frilled knickers ought to remain hidden, most of the time anyway.
He placed his head band carefully on his ringlets and pulled on the white gloves. One final fluff up of the lace on his apron straps and he was ready. He felt so relieved to be back in his four-inch heels and he minced confidently off to start his day’s work. This was now his ‘new normal’.
THE END
-
Given the constant surveillance, Mrs Winstone must've discovered Joe's true identity early on. She must've savored the challenge of training a young man to be a maid that meets her high standards, perhaps even explaining her insistence on his mincing walk and other such details.
-
Wonderful story! I just love that Joe is going to get the close and continuing supervision he needs to become the perfect maid. And he's so fortunate to return to his comfy, everyday 4-inch heels. What a lucky sissy! I'm pleased that you found a nice way to end your lovely story. He has an exciting future ahead of him!
-
DaraJaney, NO, you can't end the story. I'm sure Josephine has more adventures in him. Come on, don't leave us hanging here. :'(
-
Wow what a story. Would be super interesting to visit joe in a year as he becomes more used to the life.
-
Is that the end of the story really? Please continue the story please.
Near the end of the story his mother says that it’s only 17 more months. That is wrong if the contract was for two and a half years which is 30 months.
Some questions not answered:
How does Mrs. Winstone’s force Joe’s cooperation? Does he really get paid?
Is there really a two plus year contract or is this a joke on Joe? Is this so Mrs. Winstone has company and will not be lonely?
Why does Joe’s mother latterly sell him to Mrs. Winstone? Won’t Joe want the answer to this question?
Does Joe in the following months tell his mother and grandmother that they are dead to him? That “ His mother would turn over in her grave if she saw him acting as a maid servant.”
-
DaraJaney, you've got all of us wanting more. Josephine has to have more adventures as Mrs. Winstone. He has started his maid service adequately and we all want to know if he continues is training or if he rebels. I'm sure you can figure something out. PLEASE!!!!! :'(
-
Please continue the story. What happens next?
Love the story.
-
Wonderful story