Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: Poshboy on January 02, 2016, 06:15:11 PM
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Kyle had once again got himself in trouble at school. He had been teasing an 8 year old girl in his class who due to a nervous complaint, had frequent wetting accidents. Kyles teasing had yet again caused her to wet herself in front of the class much to her embarrassment. Betty had earned herself the nickname “Betsy Wetsie” largely due to Kyles teasing.
“Kyle Morrisey, come here this instant” shouted Miss Morgan, Kyles teacher.
“This is the last time you shall tease poor Betty”
Kyle went to Miss Morgan who grabbed his ear and dragged him into the store room. He was told to remove his school shorts, underpants, socks and t-bar sandals. He reluctantly did as he was ordered and stood and faced the wall. Betty was asked to come in and was given her spare clothes to change into whilst Kyle stood half naked with his nose to the wall and his hands on his head.
Once Betty had changed into clean clothes she returned to the class.
“Put these on” ordered Miss Morgan.
Kyle was handed Betty's wet clothes.
“Please Miss I can't, I will be laughed at.” he cried.
“You should have thought of that before you tormented poor little Betty. You will find out just how bad she felt” replied Miss Morgan.
Kyle stepped into the navy panties that were still warm with Betty's accident. As he pulled them up around his waist he was aware of his stiffening member, a cause of confusion and embarrassment. He hoped that Miss Morgan had not noticed. He had to sit down to pull on the gray tights which he found difficult at first. He stood up to pull on Betty's pleated skirt and then went to retrieve his sandals.
“No Kyle you put these on” Miss Morgan said as she handed Kyle a pair of Mary-Janes from lost property.
In tears Kyle put on the girly Mary-Janes before being lead out to his class. He was met with howls of laughter and taunting which Miss Morgan did nothing to stop. After a while Miss Morgan quieted the class down and announced that for one month Kyle wold continue to dress as he was now dressed. He would have all bathroom privileges withdrawn. At this Kyle burst into tears much to the amusement of his so called best friend Markus who shouted'
“Look at sissy Kyle crying like a baby”
Kyle was told to apologize to Betty and take his seat. Reluctantly Kyle did as he asked and sat silently on his seat. The lesson continued on whilst Kyle tried to concentrate, aware of his new clothing. As the lesson continued he became aware of his growing need to pass water. Would he truly be denied the bathroom as Miss Morgan had told his class. The more he thought about it the more the pressure built.
Eventually Kyle had no choice, he put up his hand to ask for a bathroom pass.
“Yes Kyle” Miss Morgan asked.
Eventually Kyle felt the warm spreading in “His” panties and tights. Soon a fair sized puddle formed under his chair much to the amusement of the class and the utter humiliation of Kyle. The sissy was now wetting himself in his girly clothes.
“Have you finished going potty Kyle” asked Miss Morgan.
In tears Kyle nodded yes.
“Go get a mop and clean up your mess” ordered Miss Morgan.
Kyle stood up revealing his shameful accident even more to the class and was witnessed by the class mopping up his accident. Thankfully his school day was at an end and he could return home.
Miss Morgan called him to her desk and handed him a note for his mother. He asked if he could change into his shorts and socks before returning home. Miss Morgan handed him his shorts, socks and sandals in a sealed bag and was told not to open it until he got home and gave the note to his mother.
Horrified Kyle realized that he would have to not only travel home on the bus in girls uniform, but also in wet panties too. He was totally miserable as he travelled on the bus home. He ran home after getting off the bus to avoid getting beaten up by the local bullies.
He opened the front door to be greeted by a very angry mother...
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Part 2 – Kyles New SISSY Life
When Kyles mother saw him dressed in his girls uniform and smelt the distinct odor of stale pee, she grabbed him by the ear and lead him up to his bedroom. He was told to pull down his tights and panties and bend over his desk. Once bent over the desk Kyle had to lift the back of his skirt up over his back whilst his mother went to get the paddle that was hung up above his bed.
Kyle knew what was coming and started to cry like a baby rather than the 9 year old boy he was supposed to be.
“Stop that crying young man, you have brought this on yourself. You have embarrassed me and the family and I will make sure this never happens again!” shouted his mother.12 12
She proceeded to spank Kyles exposed butt. As he whaled in pain his younger sister, 6 year old Dorothy appeared at the door. She was shocked to see her brother dressed in girls clothes and giggled until she got the look from her mother.
After 12 spanks with his paddle, Kyle was told to pull up his panties and tights and come downstairs. He slowly pulled up his damp panties and tights and lowered his skirt before joining his mother and giggling sister downstairs.
“Drink this Kyle” his mother said handing him a large glass of soda.
Kyle took the soda and drank it as instructed. He was handed a further 2 glasses to drink whilst his sister drank her small glass of soda.
“We need to go shopping for clothes for Kyle” said his mother to his sister.
Kyle knew all too well not to say anything and was told to take hold of her hand whilst they went into town for new clothes. The trip on the bus was a nightmare. He felt the eyes of everyone staring at him and saw many kids sniggering and whispering to each other.
He was relieved to get off the bus. Once again he had to take the hand of his mother like a toddler whilst his sister skipped ahead of them. The first shop they called at was the local uniform shop. He couldn't stop his tears as his mother measured pleated skirts against him.
He was shocked when he saw his best friends older sister coming towards them.
“Hello Mrs Mc Fearson, can I help you?” she said to Kyles mother.
“Yes Anne, Kyle needs a new wardrobe” replied his mother.
Smiling at Kyle Anne said “Oh yes my brother told me about what happened at school, I will be happy to help.”
Soon a pile of pleated skirts, girls school panties, tights, frilly socks, games leotards and skirts, blouses and cardigans lay on the counter. Anne made out the bill and charged it to Mrs Mc Fearson's account.
Kyle was told to thank Anne for her help.
“Thank you” replied Kyle reluctantly.
“What for sweetie” replied Anne with a smile.
“Tell her Kyle” his mother said.
“For helping me with my new clothes.” whimpered Kyle.
“For your girls clothes” sniggered Dorothy.
Kyle was lead out of the store by his mother. Again he was forced to hold his mother's hand. As they traveled to the next shop he could feel pressure in his bladder from the sodas he was made to drink earlier. He started to hold his crotch as best he could with his free hand. Noticing his mother slapped his hand away from his crotch.
“Stop that. Young ladies don't do that” his mother shouted.
He was lead into the barbers and after enduring taunts from the barber had a short back and sides haircut to emphasize that he was a boy, a little boy in a skirt. The humiliation was becoming unbearable. What else was he going to have to go through.
After leaving the barbers he was lead into the pharmacy and told to take a seat. Sullenly he took a seat and tried to take his mind off his growing need for the bathroom.
“I need diapers for my son here” announce Kyles mother.
“Mommy noo...please” cried Kyle.
“If you can't keep your panties dry you need diapers Kyle” replied his mother.
At this Kyle felt his bladder give way. In tears Kyle felt warm pee soak his panties under him and dribble down his tights. Soon a puddle formed under his seats. Kyle buried his face in his hands in utter embarrassment.
“Shame on you Kyle, how dare you embarrass me like this.”
“I see what you mean Mrs Mc Fearson, I will get some cloths to mop up his accident” said the assistant.
She went away returning with the cloths. She was told to give them to Kyle to clean up the mess he had made. Kyle proceeded to wipe up his pee pee. After cleaning up he was told to remove his skirt, tights and panties and put them in a plastic bag that was supplied by the assistant. The look on his mothers face told him not to argue. Slowly Kyle removed his skirt, tights and panties and put them in the bag.
After some discussion it was decided that cloth diapers were best. Kyle meanwhile stood in the pharmacy half naked whilst onlookers stared at his small hairless pen-is. Soon he was told to lay down to be fitted into one of his new diapers.
“We only have pink plastic panties in his size I'm sorry” said the assistant.
“That's ok, pink WILL be his favorite color, won't it Kyle” replied his mother.
Tearfully Kyle nodded in agreement whilst he was put into a cloth diaper. He then had to stand and step into the pink plastic panties. After paying for the purchases Kyle was lead outside in just his diaper and plastic panties. He couldn't bear to look up at anyone as he was lead to the next shop, Bosleys shoe shop.
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Part 3 Bosley's
Kyle was relieved to arrive so he could escape the embarrassing stares of people. He took a seat and tried to cover up his diaper. Much to his relief he was handed one of HIS school skirts to put on thus hiding his diaper.
As he sat there, his mother announced to the assistant “I need a pair of school shoes for my on here”
The assistant looked at Kyle and then at his mother.
“Sandals or girls Mary-Janes” she asked quietly.
“Well as my son is dressed like a girl I suggest the girls shoes” said his mother loudly, casing Kyle to try and hide himself even more.
The assistant went away after measuring Kyles feet.
Kyles mother sat beside him and stroked his short hair. She straightened his skirt and whispered in his ear.
“You have brought this on yourself. I have had enough of your macho naughtiness. You will be my sissy son for some time”
Soon the assistant returned with a pair of patent black Mary-janes. Reluctantly Kyle was helped into them by the grinning assistant. Kyle was then told to walk up and down to model his shoes off. He was then told to bend down and feel his toes. Tearfully Kyle did as he was told.
As he was getting up he noticed a pair of legs clad in white tights and patent Mary-Janes with gold buckles on the side. As he lifted his head he saw the legs belonged not to a girl but a boy dressed in blue velvet shorts, velvet bolero jacket under which the boy was wearing a very lacy blouse. Kyle also noticed the distinct bulge of a diaper.
As kyle looked at the boy, he recognized him as Toby a boy from his school. Toby was a bit of a loner and known to be a sissy because of his effeminate manner and his tendancy to play with girls mostly. It was rumoured he also did ballet.
“Hi there, Kyle isn't it” Toby said.
“Er yes” Kyle responded.
“I'm getting new shoes too. Mommy is buying them for my birthday, along with this smashing new suit, what do you thing.” said Toby swinging his hips to show off his sissy suit.
“Ok I guess” replied Kyle.
At this Kyles mother came over.
“Who's this Kyle darling?” she asked.
“I'm Toby.” Toby replied stretching out his hand to shake Mrs Mc Fearsons hand.
“My what a gentleman, and what a nice outfit you are wearing” Kyles mother replied.
“Yes mommy likes to dress me nicely and I like to please my mommy by being a smart and good little boy” replied Toby.
'What a little sissy' thought Kyle.
Soon they were joined by Toby's mother, Ms Grayson. The mothers talked for a while and Toby and Kyle sat down together. Toby tried to make conversation but Kyle wasn't in the mood to talk. Soon the mothers returned and announced that they were going to Toby's house for play and dinner.
After paing for Klyles new shoes they left Bosley's and got on a bus to Toby's house. Kyle tried to make himself invisible as people noticed him and Toby. Toby kept feelingnthe leg of his shorts telling Kyle how wonderful velvet feels.
Thankfully they soon arived at the stop next to Toby's house and got off the bus and walked to Toby's house. When inside Toby lead Kyle to his bedroom to play. Kyle could not believe what he saw before him. Toby's room was just like a baby's nursery, he even had a large crib. Teddy bears and other cuddly toys were every where along with a number of dolls. Posters of ballet dancers also adorned the walls. There was a large changing table along one of the walls along with a large flat sreen tv and xbox.
“What do you think of my room” Toby asked.
“It's a baby's room” shouted Kyle.
“It's a nice room and I like it. Mommy says it's a special boys room and I'm her special boy” replied Toby almost in tears.
Kyle feeling guilty for upsetting Toby appologised and sid they should play on Toby's Xbox.
Toby agreed and loaded up a game. Horrified the game was Care Bears amazing adventure. Kyle asked if Toby had any “real” games like Halo.
“Mommy says they are too violent” replied Toby.
Reluctantly Kyle procedded to play the baby's game on the Xbox as the alternative was playing dollies.
As they played Toby's momy arrived and handed them baby's bottles filled with soda. Toby eagerly took his bottle and proceeded to suc-k on the bottle. Kyle was not as keen, but fearing how his mother would be he took it and like a good sissy drank from it.
Kyle asked Toby not to tell anyone at school about how he was dressed and the baby stuff. Toby agreed as long as Kyle was his friend. Kyle reluctantly agreed.
Soon Kyle needed to pee and asked where the bathroom was. Toby said that the bathroom was only for his mommy and sister and that boys had to use their diapers. Reluctantly Kyle peed into his diaper as Toby took his turn on the Xbox.
“I need my diaper changing, do you Kyle” asked Toby.
Kyle shook his head yes. At this Toby went off and returned holding his younger sisters hand.
“Jessica will change us” said Toby
“No, I can't” cried Kyle.
“She needs to practice and mommy says we have to” replied Toby.
Kyle had to agree to this torment and agreed to have 6 year old Jessica change him. Toby was the first to climb up onto the changing table. Jessica pulled down Toby's shorts and tights revealing bright pink ruffled plastic panties which were removed revealing a yellowed soggy cloth diaper. She removed the diaper pins and diaper and cleaned Toby's privates causing Toby to get errect. Soon he was put into a new cloth diaper and redressed.
Next Kyle nervously climbed onto the changing table. His skirt was lifted up around his mid section, his plastic pants pulled down and diaper removed. He too was cleaned and tried supress his erection. He was tearfully embarrassed but Jessica just put him in a cloth diaper as if it was nothing.
After being redressed Kyle and Toby followed Jessica downstairs for dinner. Both Kyle and Toby were put into pink bibs and then given their dinner in Winnie the Pooh bowls. Their food had been chopped into bite sized chunks and they were handed plastic spoons to eat with. Jessica on the other hand had a proper plate with a knife and fork to eat with.
After dinner it was announed that Kyle would be stopping for a sleepover with Toby. Despite pleading with his mother
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Chapter 4 Sleepover
When it was time for bed, which in Toby's case was 7pm, both kyle and Toby were lead upstairs to the amily bathroom. Jessica was preparing a sweet smelling bubble bath for the two boys. Jessica helped both Kyle and toby remove their clothes and their sodden diapers. Then jessica told them both to get in the bath. Kyle looked confused, but knew not to question it.
He climbed into the bath with an excitable Toby who proceeded to play with the bath toys like a toddler. Kyle sat there bemused until toby handed him a mermaid to “play” with. Reluctantly he started to play with his mermaids hair.
Soon Toby reached over and proceeded to wash Kyle watched by Toby's mom and Jessica. Kyle was not at all keen on Toby's advances. Soon Toby was satisfied with Kyles cleanliness. Toby announced that it was Kyles turn to wash him. Kyle reluctantly lathered up Toby and proceeded to wash him all over even Toby's dinky which at Toby's insistance he reluctantly washed.
Soon oth boys were lifted out of the bath and dried all over by Jessica and Toby's mom. They were the powdered with Johnson's baby powder (only the best...Ed). Smelling like a couple f newly washed babies they were lead downstairs into the lounge to have supper. Kyle was very conscious of his naked state, particularly when Mrs Mc Fearson started taking photos “for the family album”.
Thankfully the “photo shoot” was soon over and it was time to get dressed. Jessica had Kyle lay down on a large bath towel and proceeded to put him in 3 cloth diapers that were pinned around his waist tightly. His legs were lifted so that a pair of pink ruffled plastic panties were put on over his diapers. His feet were put into pink night socks with lace tops. He stood up and was helped into pink towelling shorts with gathered leg holes. A matching pink towelling top with a yellow bunny motif on the pocket. His hands were put into wool mittens and he was handed a baby bottle of chocolate milk to drink. Toby was dressed in a matching outfit only his was yellow with a pink bunny motif.
The boys were lead up to Toby's room and helped into Toby's crib which had the noisiest plastic mattress protector on under the pink fleece sheets. They were read a bed time story by Jessica who then kissed the boys goodnite.
For Kyle it all was too much and he began to cry. Toby cuddled him close and stroked his hair whispering “It's ok now. You are special like me. Our mommies love us and I love you too. There there.
Kyle could not believe what had happened to him. One minute he had been a macho well respected bully of his school and now he was sharing a crib with a sissy baby who no one would talk to and avoided like the plague.
As he continued to cry and be comforted by Toby he started to feel different somehow. He started to feel warm inside. He felt somehow calm and had a fuzzy feeling inside. As he calmed down he felt his eyes getting heavy and soon sleep took over.
As both boys slept their diapers became warm as they happily wet their diapers. Both safe and secure in the knowledge that was what their diapers were for.
At around 7 am Kyle was the first to wake. It took him a while to work out where he was. He was accutely aware that his diaper was wet. He was also aware that he needed to empty his bowels. As he strggled with his need Toby woke and kissed Kyle on the cheek. Taken aback Kyle sat up sharply.
“What's a matter Kylee” asked Toby.
“ I need to poop” replied Kyle, not noticing the femenine name toby had used.
“Do poo poo in you diapee” replied Toby.
“I can't” replied Kyle.
“I will show you” said Toby.
Toby sat up into a crouched position and proceeded to push poop into his sodden diaper. Satisfied with his accomplishment Toby told Kyle to try. Kyle proceeded to crouch and pushed. He was surprised how soon his diaper was being filled with poop. Toby clapped excitedly and told him how well he had done.
“Yes, Kyle well done”
Kyle turned to see Jessica standing at the doorway clapping with a smirk on her face. She asked if both boys had finished their poopies. Toby smiling confirmed he had and Kyle after prompting shook his head yes.
Both boys were lead downstairs to have breakfast sitting in their poopie diapers. After breakfast the boys were lead upstairs to be bathed and readied for the day. Jessica announced that they would be dropped off at ballet class whilst he and Mrs mc ferson would go shopping.
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Chapter 5 Ballet Class
Jessica took off both boys dirty diapers and dumped into the diaper pail in Toby's room. She then bathed them both in a lavender bubble bath. Once they were clean and smelling nice they were dried powdered and taken into Toby's room to be readied for ballet class.
First the boys were helped into Princess pullups. They were then helped into pink tights and a pink leotard with attached chiffon skirt. They wore lace ankles and Mary-Janes whilst being taken to the ballet class.
Jessica took both boys downstairs to Mrs Mc Ferson. “Oh don't you two look adorable”
Kyle was a bit taken aback being called adorable. Not a term he was used to, but he also liked it. Toby hugged Kyle and said “Your my best boyfriend”
Kyle started to cry as he was not used to being loved so much.
Soon it was time to set off to ballet class, so both boys held hands and skipped in front of Jessica on the way to their class. Kyle was still a little self conscious of his appearance out in public, but skipped with Toby. They got plenty of oohs and ahhs from passer byes aswell as teasing from other neighborhood boys.
Non too soon they arrived at the local ballet school and entered quickly. They went into the “boys” changing room and changed into ballet slippers and then sat together and waited for class to start.
As they waited Kyle was surprised to see a boy he knew all too well enter the room. It was Billy, the school bully. Only he was dressed in a sailor suit. It was white with white shorts under which he was wearing white tights with shiny patent Mary-Janes on his feet.
When Billy saw Kyle he went white as a sheet. He came over to Kyle and with a tear in his eye, pleaded with Kyle not to tell anyone at school. Kyle promised as long as Billy promised to protect him at school. Billy agreed and went over to his mom to get changed. As Kyle watched in amazement, Billy's mom removed his shorts and tights revealing that he was wearing girls ruffled panties. When Billy looked at Kyle, Kyle just smiled and gave him a thumbs up. Billy was then helped into Princess pullups, pink tights and pink leotard like Toby and kyle.
As Billy was changed two twin boys entered the room. Both were dressed I short kilts, white tights worn under white ruffled panties. They also had the laciest blouses Kyle had ever seen. They were helped to change. Both boys were diapered so their leotard and tights displayed a distinct bulge.
Once ready all the boys went to join the girls to start ballet class. Kyle soon picket up the basics and found he enjoyed the music and dancing to it. Billy was very good at the dancing and was very graceful. The girls loved seeing the sissy boys dancing and at the end of class they all curtsied and thanked their dance teacher. Toby had to show Kyle how to curtsy.
After changing back into their outdoor clothes Kyle and Toby were invited over to Billy's house for a sleepover the following week. The twins were also invited. Apparently it was going to be Billy's 10th birthday. Jessica said it was ok and that she would take the boys hopping for presents for him.
After leaving the ballet school they joined Mrs Mc Ferson to go shopping. Kyle chose some tights and new panties for Billy. The pack of panties were princess days of the week panties and the tights were delicate white ones. Toby got Billy a new pair of of blue satin shorts with matching jacket saying it would go nice with Kyles present.
They returned to Tobys home were Kyles mommy was waiting. Kyle did something he had not done in years. He ran to her and gave her the biggest hug with tears in his eyes. He said that he was sorry he had been mean to the girl in school and that he had been such a brat.
It was a special moment for them both as they returned home. Kyle loved his mommy and loved the attention he was now receiving.
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Kyles Punishment
Chapter 1 in Trouble Again
Kyle had once again got himself in trouble at school. He had been teasing an 8 year old girl in his class who due to a nervous complaint, had frequent wetting accidents. Kyles teasing had yet again caused her to wet herself in front of the class much to her embarrassment. Betty had earned herself the nickname “Betsy Wetsie” largely due to Kyles teasing.
“Kyle Mc Fearson, come here this instant” shouted Miss Morgan, Kyles teacher.
“This is the last time you shall tease poor Betty”
Kyle went to Miss Morgan who grabbed his ear and dragged him into the store room. He was told to remove his school shorts, underpants, socks and t-bar sandals. He reluctantly did as he was ordered and stood and faced the wall. Betty was asked to come in and was given her spare clothes to change into whilst Kyle stood half naked with his nose to the wall and his hands on his head.
Once Betty had changed into clean clothes she returned to the class.
“Put these on” ordered Miss Morgan.
Kyle was handed Betty's wet clothes.
“Please Miss I can't, I will be laughed at.” he cried.
“You should have thought of that before you tormented poor little Betty. You will find out just how bad she felt” replied Miss Morgan.
Kyle stepped into the navy panties that were still warm with Betty's accident. As he pulled them up around his waist he was aware of his stiffening member, a cause of confusion and embarrassment. He hoped that Miss Morgan had not noticed. He had to sit down to pull on the gray tights which he found difficult at first. He stood up to pull on Betty's pleated skirt and then went to retrieve his sandals.
“No Kyle you put these on” Miss Morgan said as she handed Kyle a pair of Mary-Janes from lost property.
In tears Kyle put on the girly Mary-Janes before being lead out to his class. He was met with howls of laughter and taunting which Miss Morgan did nothing to stop. After a while Miss Morgan quieted the class down and announced that for one month Kyle wold continue to dress as he was now dressed. He would have all bathroom privileges withdrawn. At this Kyle burst into tears much to the amusement of his so called best friend Markus who shouted'
“Look at sissy Kyle crying like a baby”
Kyle was told to apologize to Betty and take his seat. Reluctantly Kyle did as he asked and sat silently on his seat. The lesson continued on whilst Kyle tried to concentrate, aware of his new clothing. As the lesson continued he became aware of his growing need to pass water. Would he truly be denied the bathroom as Miss Morgan had told his class. The more he thought about it the more the pressure built.
Eventually Kyle had no choice, he put up his hand to ask for a bathroom pass.
“Yes Kyle” Miss Morgan asked.
Eventually Kyle felt the warm spreading in “His” panties and tights. Soon a fair sized puddle formed under his chair much to the amusement of the class and the utter humiliation of Kyle. The sissy was now wetting himself in his girly clothes.
“Have you finished going potty Kyle” asked Miss Morgan.
In tears Kyle nodded yes.
“Go get a mop and clean up your mess” ordered Miss Morgan.
Kyle stood up revealing his shameful accident even more to the class and was witnessed by the class mopping up his accident. Thankfully his school day was at an end and he could return home.
Miss Morgan called him to her desk and handed him a note for his mother. He asked if he could change into his shorts and socks before returning home. Miss Morgan handed him his shorts, socks and sandals in a sealed bag and was told not to open it until he got home and gave the note to his mother.
Horrified Kyle realized that he would have to not only travel home on the bus in girls uniform, but also in wet panties too. He was totally miserable as he travelled on the bus home. He ran home after getting off the bus to avoid getting beaten up by the local bullies.
He opened the front door to be greeted by a very angry mother...
Part 2 – Kyles New SISSY Life
When Kyles mother saw him dressed in his girls uniform and smelt the distinct odor of stale pee, she grabbed him by the ear and lead him up to his bedroom. He was told to pull down his tights and panties and bend over his desk. Once bent over the desk Kyle had to lift the back of his skirt up over his back whilst his mother went to get the paddle that was hung up above his bed.
Kyle knew what was coming and started to cry like a baby rather than the 9 year old boy he was supposed to be.
“Stop that crying young man, you have brought this on yourself. You have embarrassed me and the family and I will make sure this never happens again!” shouted his mother.12 12
She proceeded to spank Kyles exposed butt. As he whaled in pain his younger sister, 6 year old Dorothy appeared at the door. She was shocked to see her brother dressed in girls clothes and giggled until she got the look from her mother.
After 12 spanks with his paddle, Kyle was told to pull up his panties and tights and come downstairs. He slowly pulled up his damp panties and tights and lowered his skirt before joining his mother and giggling sister downstairs.
“Drink this Kyle” his mother said handing him a large glass of soda.
Kyle took the soda and drank it as instructed. He was handed a further 2 glasses to drink whilst his sister drank her small glass of soda.
“We need to go shopping for clothes for Kyle” said his mother to his sister.
Kyle knew all too well not to say anything and was told to take hold of her hand whilst they went into town for new clothes. The trip on the bus was a nightmare. He felt the eyes of everyone staring at him and saw many kids sniggering and whispering to each other.
He was relieved to get off the bus. Once again he had to take the hand of his mother like a toddler whilst his sister skipped ahead of them. The first shop they called at was the local uniform shop. He couldn't stop his tears as his mother measured pleated skirts against him.
He was shocked when he saw his best friends older sister coming towards them.
“Hello Mrs Mc Fearson, can I help you?” she said to Kyles mother.
“Yes Anne, Kyle needs a new wardrobe” replied his mother.
Smiling at Kyle Anne said “Oh yes my brother told me about what happened at school, I will be happy to help.”
Soon a pile of pleated skirts, girls school panties, tights, frilly socks, games leotards and skirts, blouses and cardigans lay on the counter. Anne made out the bill and charged it to Mrs Mc Fearson's account.
Kyle was told to thank Anne for her help.
“Thank you” replied Kyle reluctantly.
“What for sweetie” replied Anne with a smile.
“Tell her Kyle” his mother said.
“For helping me with my new clothes.” whimpered Kyle.
“For your girls clothes” sniggered Dorothy.
Kyle was lead out of the store by his mother. Again he was forced to hold his mother's hand. As they traveled to the next shop he could feel pressure in his bladder from the sodas he was made to drink earlier. He started to hold his crotch as best he could with his free hand. Noticing his mother slapped his hand away from his crotch.
“Stop that. Young ladies don't do that” his mother shouted.
He was lead into the barbers and after enduring taunts from the barber had a short back and sides haircut to emphasize that he was a boy, a little boy in a skirt. The humiliation was becoming unbearable. What else was he going to have to go through.
After leaving the barbers he was lead into the pharmacy and told to take a seat. Sullenly he took a seat and tried to take his mind off his growing need for the bathroom.
“I need diapers for my son here” announce Kyles mother.
“Mommy noo...please” cried Kyle.
“If you can't keep your panties dry you need diapers Kyle” replied his mother.
At this Kyle felt his bladder give way. In tears Kyle felt warm pee soak his panties under him and dribble down his tights. Soon a puddle formed under his seats. Kyle buried his face in his hands in utter embarrassment.
“Shame on you Kyle, how dare you embarrass me like this.”
“I see what you mean Mrs Mc Fearson, I will get some cloths to mop up his accident” said the assistant.
She went away returning with the clothes. She was told to give them to Kyle to clean up the mess he had made. Kyle proceeded to wipe up his pee pee. After cleaning up he was told to remove his skirt, tights and panties and put them in a plastic bag that was supplied by the assistant. The look on his mothers face told him not to argue. Slowly Kyle removed his skirt, tights and panties and put them in the bag.
After some discussion it was decided that cloth diapers were best. Kyle meanwhile stood in the pharmacy half naked whilst onlookers stared at his small hairless pen-is. Soon he was told to lay down to be fitted into one of his new diapers.
“We only have pink plastic panties in his size I'm sorry” said the assistant.
“That's ok, pink WILL be his favorite color, won't it Kyle” replied his mother.
Tearfully Kyle nodded in agreement whilst he was put into a cloth diaper. He then had to stand and step into the pink plastic panties. After paying for the purchases Kyle was lead outside in just his diaper and plastic panties. He couldn't bear to look up at anyone as he was lead to the next shop, Bosleys shoe shop.
Part 3 Bosley's
Kyle was relieved to arrive so he could escape the embarrassing stares of people. He took a seat and tried to cover up his diaper. Much to his relief he was handed one of HIS school skirts to put on thus hiding his diaper.
As he sat there, his mother announced to the assistant “I need a pair of school shoes for my on here”
The assistant looked at Kyle and then at his mother.
“Sandals or girls Mary-Janes” she asked quietly.
“Well as my son is dressed like a girl I suggest the girls shoes” said his mother loudly, casing Kyle to try and hide himself even more.
The assistant went away after measuring Kyles feet.
Kyles mother sat beside him and stroked his short hair. She straightened his skirt and whispered in his ear.
“You have brought this on yourself. I have had enough of your macho naughtiness. You will be my sissy son for some time”
Soon the assistant returned with a pair of patent black Mary-janes. Reluctantly Kyle was helped into them by the grinning assistant. Kyle was then told to walk up and down to model his shoes off. He was then told to bend down and feel his toes. Tearfully Kyle did as he was told.
As he was getting up he noticed a pair of legs clad in white tights and patent Mary-Janes with gold buckles on the side. As he lifted his head he saw the legs belonged not to a girl but a boy dressed in blue velvet shorts, velvet bolero jacket under which the boy was wearing a very lacy blouse. Kyle also noticed the distinct bulge of a diaper.
As kyle looked at the boy, he recognized him as Toby a boy from his school. Toby was a bit of a loner and known to be a sissy because of his effeminate manner and his tendency to play with girls mostly. It was rumored he also did ballet.
“Hi there, Kyle isn't it” Toby said.
“Er yes” Kyle responded.
“I'm getting new shoes too. Mommy is buying them for my birthday, along with this smashing new suit, what do you thing.” said Toby swinging his hips to show off his sissy suit.
“Ok I guess” replied Kyle.
At this Kyles mother came over.
“Who's this Kyle darling?” she asked.
“I'm Toby.” Toby replied stretching out his hand to shake Mrs Mc Fearson's hand.
“My what a gentleman, and what a nice outfit you are wearing” Kyles mother replied.
“Yes mommy likes to dress me nicely and I like to please my mommy by being a smart and good little boy” replied Toby.
'What a little sissy' thought Kyle.
Soon they were joined by Toby's mother, Ms Grayson. The mothers talked for a while and Toby and Kyle sat down together. Toby tried to make conversation but Kyle wasn't in the mood to talk. Soon the mothers returned and announced that they were going to Toby's house for play and dinner.
After paing for Klyles new shoes they left Bosley's and got on a bus to Toby's house. Kyle tried to make himself invisible as people noticed him and Toby. Toby kept feelingnthe leg of his shorts telling Kyle how wonderful velvet feels.
Thankfully they soon arived at the stop next to Toby's house and got off the bus and walked to Toby's house. When inside Toby lead Kyle to his bedroom to play. Kyle could not believe what he saw before him. Toby's room was just like a baby's nursery, he even had a large crib. Teddy bears and other cuddly toys were every where along with a number of dolls. Posters of ballet dancers also adorned the walls. There was a large changing table along one of the walls along with a large flat sreen tv and xbox.
“What do you think of my room” Toby asked.
“It's a baby's room” shouted Kyle.
“It's a nice room and I like it. Mommy says it's a special boys room and I'm her special boy” replied Toby almost in tears.
Kyle feeling guilty for upsetting Toby apologized and said they should play on Toby's Xbox.
Toby agreed and loaded up a game. Horrified the game was Care Bears amazing adventure. Kyle asked if Toby had any “real” games like Halo.
“Mommy says they are too violent” replied Toby.
Reluctantly Kyle proceeded to play the baby's game on the Xbox as the alternative was playing dollies.
As they played Toby's mommy arrived and handed them baby's bottles filled with soda. Toby eagerly took his bottle and proceeded to suc-k on the bottle. Kyle was not as keen, but fearing how his mother would be he took it and like a good sissy drank from it.
Kyle asked Toby not to tell anyone at school about how he was dressed and the baby stuff. Toby agreed as long as Kyle was his friend. Kyle reluctantly agreed.
Soon Kyle needed to pee and asked where the bathroom was. Toby said that the bathroom was only for his mommy and sister and that boys had to use their diapers. Reluctantly Kyle peed into his diaper as Toby took his turn on the Xbox.
“I need my diaper changing, do you Kyle” asked Toby.
Kyle shook his head yes. At this Toby went off and returned holding his younger sisters hand.
“Jessica will change us” said Toby
“No, I can't” cried Kyle.
“She needs to practice and mommy says we have to” replied Toby.
Kyle had to agree to this torment and agreed to have 6 year old Jessica change him. Toby was the first to climb up onto the changing table. Jessica pulled down Toby's shorts and tights revealing bright pink ruffled plastic panties which were removed revealing a yellowed soggy cloth diaper. She removed the diaper pins and diaper and cleaned Toby's privates causing Toby to get erect. Soon he was put into a new cloth diaper and redressed.
Next Kyle nervously climbed onto the changing table. His skirt was lifted up around his mid section, his plastic pants pulled down and diaper removed. He too was cleaned and tried supress his erection. He was tearfully embarrassed but Jessica just put him in a cloth diaper as if it was nothing.
After being redressed Kyle and Toby followed Jessica downstairs for dinner. Both Kyle and Toby were put into pink bibs and then given their dinner in Winnie the Pooh bowls. Their food had been chopped into bite sized chunks and they were handed plastic spoons to eat with. Jessica on the other hand had a proper plate with a knife and fork to eat with.
After dinner it was announced that Kyle would be stopping for a sleepover with Toby. Despite pleading with his mother.
Chapter 4 Sleepover
When it was time for bed, which in Toby's case was 7pm, both kyle and Toby were lead upstairs to the family bathroom. Jessica was preparing a sweet smelling bubble bath for the two boys. Jessica helped both Kyle and Toby remove their clothes and their sodden diapers. Then jessica told them both to get in the bath. Kyle looked confused, but knew not to question it.
He climbed into the bath with an excitable Toby who proceeded to play with the bath toys like a toddler. Kyle sat there bemused until Toby handed him a mermaid to “play” with. Reluctantly he started to play with his mermaids hair.
Soon Toby reached over and proceeded to wash Kyle watched by Toby's mom and Jessica. Kyle was not at all keen on Toby's advances. Soon Toby was satisfied with Kyles cleanliness. Toby announced that it was Kyles turn to wash him. Kyle reluctantly lathered up Toby and proceeded to wash him all over even Toby's dinky which at Toby's insistence he reluctantly washed.
Soon oth boys were lifted out of the bath and dried all over by Jessica and Toby's mom. They were the powdered with Johnson's baby powder (only the best...Ed). Smelling like a couple of newly washed babies they were lead downstairs into the lounge to have supper. Kyle was very conscious of his naked state, particularly when Mrs Mc Fearson started taking photos “for the family album”.
Thankfully the “photo shoot” was soon over and it was time to get dressed. Jessica had Kyle lay down on a large bath towel and proceeded to put him in 3 cloth diapers that were pinned around his waist tightly. His legs were lifted so that a pair of pink ruffled plastic panties were put on over his diapers. His feet were put into pink night socks with lace tops. He stood up and was helped into pink towelling shorts with gathered leg holes. A matching pink towelling top with a yellow bunny motif on the pocket. His hands were put into wool mittens and he was handed a baby bottle of chocolate milk to drink. Toby was dressed in a matching outfit only his was yellow with a pink bunny motif.
The boys were lead up to Toby's room and helped into Toby's crib which had the noisiest plastic mattress protector on under the pink fleece sheets. They were read a bed time story by Jessica who then kissed the boys goodnite.
For Kyle it all was too much and he began to cry. Toby cuddled him close and stroked his hair whispering “It's ok now. You are special like me. Our mommies love us and I love you too. There there.
Kyle could not believe what had happened to him. One minute he had been a macho well respected bully of his school and now he was sharing a crib with a sissy baby who no one would talk to and avoided like the plague.
As he continued to cry and be comforted by Toby he started to feel different somehow. He started to feel warm inside. He felt somehow calm and had a fuzzy feeling inside. As he calmed down he felt his eyes getting heavy and soon sleep took over.
As both boys slept their diapers became warm as they happily wet their diapers. Both safe and secure in the knowledge that was what their diapers were .
At around 7 am Kyle was the first to wake. It took him a while to work out where he was. He was accutely aware that his diaper was wet. He was also aware that he needed to empty his bowels. As he strggled with his need Toby woke and kissed Kyle on the cheek. Taken aback Kyle sat up sharply.
“What's a matter Kylee” asked Toby.
“ I need to poop” replied Kyle, not noticing the femenine name toby had used.
“Do poo poo in your diapee” replied Toby.
“I can't” replied Kyle.
“I will show you” said Toby.
Toby sat up into a crouched position and proceeded to push poop into his sodden diaper. Satisfied with his accomplishment Toby told Kyle to try. Kyle proceeded to crouch and pushed. He was surprised how soon his diaper was being filled with poop. Toby clapped excitedly and told him how well he had done.
“Yes, Kyle well done”
Kyle turned to see Jessica standing at the doorway clapping with a smirk on her face. She asked if both boys had finished their poopies. Toby smiling confirmed he had and Kyle after prompting shook his head yes.
Both boys were lead downstairs to have breakfast sitting in their poopie diapers. After breakfast the boys were lead upstairs to be bathed and readied for the day. Jessica announced that they would be dropped off at ballet class whilst she and Mrs Mc Ferson would go shopping.
Chapter 5 Ballet Class
Jessica took off both boys dirty diapers and dumped into the diaper pail in Toby's room. She then bathed them both in a lavender bubble bath. Once they were clean and smelling nice they were dried powdered and taken into Toby's room to be readied for ballet class.
First the boys were helped into Princess pullups. They were then helped into pink tights and a pink leotard with attached chiffon skirt. They wore lace ankles and Mary-Janes whilst being taken to the ballet class.
Jessica took both boys downstairs to Mrs Mc Ferson. “Oh don't you two look adorable”
Kyle was a bit taken aback being called adorable. Not a term he was used to, but he also liked it. Toby hugged Kyle and said “Your my best boyfriend”
Kyle started to cry as he was not used to being loved so much.
Soon it was time to set off to ballet class, so both boys held hands and skipped in front of Jessica on the way to their class. Kyle was still a little self conscious of his appearance out in public, but skipped with Toby. They got plenty of oohs and ahhs from passer byes aswell as teasing from other neighborhood boys.
Non too soon they arrived at the local ballet school and entered quickly. They went into the “boys” changing room and changed into ballet slippers and then sat together and waited for class to start.
As they waited Kyle was surprised to see a boy he knew all too well enter the room. It was Billy, the school bully. Only he was dressed in a sailor suit. It was white with white shorts under which he was wearing white tights with shiny patent Mary-Janes on his feet.
When Billy saw Kyle he went white as a sheet. He came over to Kyle and with a tear in his eye, pleaded with Kyle not to tell anyone at school. Kyle promised as long as Billy promised to protect him at school. Billy agreed and went over to his mom to get changed. As Kyle watched in amazement, Billy's mom removed his shorts and tights revealing that he was wearing girls ruffled panties. When Billy looked at Kyle, Kyle just smiled and gave him a thumbs up. Billy was then helped into Princess pullups, pink tights and pink leotard like Toby and kyle.
As Billy was changed two twin boys entered the room. Both were dressed I short kilts, white tights worn under white ruffled panties. They also had the laciest blouses Kyle had ever seen. They were helped to change. Both boys were diapered so their leotard and tights displayed a distinct bulge.
Once ready all the boys went to join the girls to start ballet class. Kyle soon picket up the basics and found he enjoyed the music and dancing to it. Billy was very good at the dancing and was very graceful. The girls loved seeing the sissy boys dancing and at the end of class they all curtsied and thanked their dance teacher. Toby had to show Kyle how to curtsy.
After changing back into their outdoor clothes Kyle and Toby were invited over to Billy's house for a sleepover the following week. The twins were also invited. Apparently it was going to be Billy's 10th birthday. Jessica said it was ok and that she would take the boys shopping for presents for him.
After leaving the ballet school they joined Ma Grayson to go shopping. Kyle chose some tights and new panties for Billy. The pack of panties were princess days of the week panties and the tights were delicate white ones. Toby got Billy a new pair of of blue satin shorts with matching jacket saying it would go nice with Kyles present.
They returned to Tobys home were Kyles mommy was waiting. Kyle did something he had not done in years. He ran to her and gave her the biggest hug with tears in his eyes. He said that he was sorry he had been mean to the girl in school and that he had been such a brat.
It was a special moment for them both as they returned home. Kyle loved his mommy and loved the attention he was now receiving.
Chapter 6 Billy Is 10
When Kyle and his mommy returned home they sat on the couch and watched The Nutcracker. Kyle sat with his head in his mommy's lap. He said how he liked the boys clothes and how he liked Toby's clothes too. Mrs Mc Fearson said that she could get him some new “Boys Clothes” like on the Nutcracker and like Toby's as well as girls clothes for when he wanted girl time. Smiling up at his momm he said :-
“That would be nice mommy.”
Mrs Mc Fearson was so pleased to get her nice son back and remembered the early days when she was able to dress him in little kilts and nice panties.
As Kyles mommy continued to stroke the hair of her boy dressed in his ballet clothes, Dorothy came in with a cup of coffee for her and a bottle of formula for Kyle. Smiling she handed Kylehis bottle to drink.
“I love your leotard Kyle” she said kindly.
Soon it was 7pm and Kyles new bedtime. Kyle did actually feel very sleepy, so didn't argue when Dorothy offered to bath him and get him ready for bed. Dorothy took Kyles hand and took him upstairs, removed his leotard, tights and diaper and helped him into his bubble bath. She bathed him, dried and powdered him before taking him into his bedroom. She had him lay on his changing mat and put him in 3 thick terry diapers, helped him into pink ruffled plastic panties. He was then dressed in pink footed pajamas with a large rag doll motif on the front. After handing him a pacifier to suc-k on he was tucked into bed and she read him a bedtime story before kissing him on his cheek.
“Good nite my sweet little brother. I'm so glad I have such a nice baby brother to care for”
Meanwhile at Toby's house he was getting similar treatment. Toby was waering his “nightshirt” which was a mass of lace frills. He told Jessica how he loved Kyle and was glad he had become a sissy like him and Billy was also becoming one too. Jessica smiled and said hom glad she ws too.
As the morning arrived Kyle awoke to the now familiar wet diaper only he also noticed that he had a mass of poop deposited in the back of his diaper. He was embarrassed when Dorothy entered his bedroom and noticed his childish condition.
“Is my baby brother a wittle stinky butt” said Dorothy smiling.
“Yes and big sis has to change it” said Kyle smiling back.
“is it ok if I do it after breakfast” Dorothy asked.
“Sure then I can squish it around some more” laughed Kyle.
“It's so good to see you two getting on so well” said their mommy arriving at the door.
They all went to breakfast. Kyle true to his word sat wiggling his butt so poop was squished all over, much to the amusement of his sister and mommy. Dorothy said they would have to get gass masks for diaper change time.
As soon as breakfast was over Dorothy took kyle to get ready for school. Kyle was cleaned and re-diapered. He was dressed in his boys school uniform, only he opted for a kilt rather than shorts and mary-janes rather than trainers. The kilt was an option for the boys uniform that was rarely chosen by other boys in the school. But Kyle chose it from now on. He was not teased at school as it was made clear that he and Toby were now under the protection of Billy who also had started wearing the kilt option.
Soon it was time for Billy's birthday party and sleepover. Both Kyle and Toby were looking forward to it and had special outfits prepared. After being bathed and diapered Kyle ws dressed in his outfit. First his white lace tights were pulled up hi legs and fastened around the waist. Next red velvet shorts were pulled up. Two pearl buttons were on the bottom of each leg and on the inseam were snaps to aide diaper changes. Tucked into the shorts was a lace blouse with huge lace colar and cuffs. Over his blouse was a matching bolero jacket. Dorothy then had kyle sit down whilst lace anklets were put on his feet followed by black patent mary-janes.
Kyles mommy just gushed when she saw how sweet Kyle looked and took many photos. Excitedly they waited for Toby and his mommy to pick them up for the journey to Billys. It seemed to take far too long for Kyle, but eventually they arrived. Kyle hurried to the door. Toby stood at the door dressed in a velvet baby blue romper suit with white tights and blue mary-janes. He was holding tightly onto Jessicas hand. More photos were taken before Toby and Kyle were strapped into car seats and setting off for Billys.
When they arrived they were greeted by Billy dressed in a pink satin sailor suit with pink tights and matching ballet slippers. Billy hugged both Kyle and Toby. After saying goodbye to their mommys, Kyle and Toby joined the party. The other boys at the party ranged from 5 year old Simon to 15 year old Peter. They too were dressed up Simon was dressed in a white sailor dress short enough to show off his white ruffled plastic panties. Peter was dressed in a navy eton short pants suit white pereline knee socks and sadle shoes. Billy's cousins, twins Markus and Jasmine were dressed in matching ballerina outfits. Both 8 year old twins sported distinct diaper bulges under their pink leotards.
After a few party games they had their party food. All were given strawberry milk in baby bottles aswell as being put in large bibs so as not to spoil there nice clothes. As soon as all had their fill of party food it was time for diaper change. Peter helped with the twins diaper changes whilst Billy helped Kyle and Toby into fresh dapers. He made sure to excite both boys during this time. Peter was changed by Billy's mommy. Kyle changed Billy and returned the favor he had bestowed on him.
Soon it was time for Billy to open his presents. He got an entire new wardrobe of fancy clothes including skirts, dresses, rompers, sailor suits, kilts, tights, panties, cloth diapers and plastic panties. He also got a few dollies and other toys.
Too soon the party was over and time for the other children to leave. So there was a period of hugs and kisses before Billy, Toby and Kyle were left alone and it was time to get ready for bed. The boys shared a nice bubble bath together. They were then diapered and put into nighties ready to go to bed. Billy slept in the middle of Kyle and Toby. After their story they were told that they would be on holiday for a week and would be going to a new school, a special school for boys like them.
It was hard o sleep as the boys were excited about their new school.. :)
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Here's the update. Had probs with internet for a few days...
Chapter 7 – New uniform
In the morning Toby and kyle woke to find Billy's hands down the front of their very soggy diapers. They both turned and kissed Billy on the cheek waking a rather embarrassed Billy. The boys got up and waddled downstairs for breakfast. It was there favorite Cheerios. They managed to get milk all down their nighties which caused a lot of giggles. After watching Barney and Rugrats on TV the boys skipped to the bathroom to be bathed. All the boys enjoyed period of bath time “ play” before going into Billy's room for diapering and dressing. Billy was dressed in his new kilt with white tights that had lace on the rear. His lace blouse went under a red velvet bolero jacket and on his feet he wore lace anklets and black patent Mary-Janes. Toby and Kyle said how cute he looked whilst his mother snapped a few photos.
Kyle and Toby were dressed in blue cotton sailor suits with white tights under their shorts and black Mary-Janes. The distinct diaper bulge showed under their shorts which was thought very cute by all.
Billy's mommy, Mrs Jones, announced that they needed to go to get their new uniforms after which they could go to play in the park.
“Yey” said the boys in unison.
Soon they were strapped into the back seat of Mrs Jones 4x4 and were travelling to the specialist clothes shop outside of town. The boys happily chatted about how nice it would be to be with boys like them at the new school.
They soon arrived at the clothes shop and were fascinated by the huge collection of beautiful boys clothes that ranged from large romper suits to kilted and skirted suits. Large selections of baby apparel in their sizes were there also. The boys were so excited that simultaneously they wet their diapers.
Other boys were trying on all sorts of new clothes. Some reluctantly and some excitedly. The reluctant ones Mrs Jones explained were undergoing “Petticoat Punishment”. Toby could not understand how dressing in nice clothes was a punishment.
The new school uniform consisted of a baby blue kilt and matching Eton style jacket, white lace blouse with baby blue bow tie. White tights were worn in summer and grey in winter. Their current Mary-Janes were suitable for school shoes. Ofcourse diapers would be worn, but disposable ones were not permitted so pink cloth diapers had to be worn under pink plastic panties.
For P.E. the boys would wear baby blue leotards, white tights and pink ballet pumps. A gym skirt of white would be worn for netball. One piece blue swimsuits would be used for swimming lessons.
Soon the boys had their new uniforms sorted out and also got to pick out new romper suits as a special treat. They also chose new pacifiers, baby bottles and a new teddy bear for taking to the park.
It was decided to change all boys diapers before going to the park. So they headed to the changing station at the back of the shop. Billy recognised his friend Peter from the party. He was standing in a white shirt with short puffed sleeves and peter pan collar that was edged in pink gingham trim. His shortalls were on the changing table leaving Peter just in his cloth diaper and clear plastic panties. His diaper was already yellow from excessive wetting. Peter could be heard grunting as he was trying to poop. Billy went over and tried to assist by rubbing his back and giving encouraging words. Soon Peter achieved his aim and a distinct and growing bulge was witnessed in the seat of his diaper. Peter was then changed by his sister Mary whilst Billy excitedly told him about the new school that he, Toby and Kyle would be attending next week. Peter told them what a great place it was.
After their change the boys carried their new clothes out to the car and after kissing Peter goodbye set off for the park.
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Chapter 8 The Park
Excitedly the boys got into the car to set off for the park. Mrs jones said that they would be going to the park attached to their new school where they would be able to play with sissy boys like themselves. The boys grew even more excited and could hardly wait.
After about half an hour they arrived at the park. Mrs Jones said that as it was such a nice day and not to ruin their nice clothes, the boys should strip to their diapers. Billy helped Toby strip to his diapers and plastic panties whilst Mrs Jones helped Kyle. Kyle then helped Billy. Soon they were all in just their diapers and plastic panties. The boys folded their clothes neatly and rolled their tights into little balls.
Billy held onto his mommies hand whilst Toby and Kyle held each others hands. They followed Mrs Jones to the park and soon saw an array of boys and girls of all ages. All dressed in the cutest outfits you could imagine. The girls tended to be supervising the boys rather than playing.
“Lets go and play in the sand pit” said Toby and kyle excitedly.
“I'll go on the swings” announced Billy.
So off they went whilst Mrs Jones found a table to sit at.
Billy sat on a swing next to a boy dressed in white ribbed tights, short blue t-shirt and blue t-bar sandals. He looked to be about 7 and had long blond hair with beautiful ringlets. A distinct diaper bulge could be seen. Billy introduced himself to the boy.
“I'm Wupert” lisped the boy.
Billy thought it so cute how he spoke and complimented him on his outfit. After giving Rupert a pus he got onto the swing and pushed himself off. Rupert was quite the chatterbox and soon both boys were chatting.
Toby and Kyle reached the sand pit where two boys were playing. A boy of 6 was playing with a toy digger. He was dressed in a blue cotton dress, white anklets and blue Mary-Janes. The other boy was building sand castles and was dressed in blue shortals that showed the evidence of recent wetting “accident”. He wore nothing on his feet or under his shortals. He looked to be about 8.
Toby and Kyle introduced themselves and found out the boys were Karl and Francis. They decided to build a large sand castle together. Soon the boys were busy building a huge sand castle.
After 15 minutes Francis got a far away look on his and soon a large wet spot was forming on the front of his shortals. The boys excitedly watched as Francis made potty small in his shortals.
“I'm making the moat” giggled francis.
After emptying his bladder fully the boys returned to their sand castle. Kyle and Toby made their own moats in their diapers with applause from the other boys. Soon it was Karls turn to make potty small. He lifted the front of his dress whilst on his knees revealing pink panties edged with white lace.
Toby and Kyle turned and looked. They watched as the pink panties turned dark pink around the tip of his dink. Soon a steady flow could be seen soaking into the sand. As soon as he finished Karls brother came over dressed in red shorts and white blouse. Without saying a word he pulled down his shorts revealing yellow panties with “princess boy” written on he front. He took them off and handed them to Karl who had taken off his wet panties and handed them to his brother. His brother took them and put them on before pulling on his shorts.
“Thanks Karl” said his brother before skipping off.
Karl pulled on the dry “Princess Boy” panties and announced that he and his brother Peter liked to share. The boys laughed together and chatted about how they liked wet panties and diapers.
Soon it was time for lunch so Toby and Kyle said goodbye and joined Billy at the table Mrs Jones had laid out a picnic lunch on. The boys were soon demolishing a delicious lunch and drinking from new baby bottles. After lunch Mrs Jones announced that the boys could go to the paddling pool. She went to the car and got the boys their swim suits. Soon the boys were stripped and eagerly getting into one piece swimsuits with cute ruffled skirts around the waist.
The three boys went off to the paddling pool whilst Mrs Jones cleared the table. When they arrived at the pool they saw Karl and Francis splashing about. Francis was in a pink bikini and Karl was skinny dipping. They had fun splashing each other and soon it was time to go. They agreed to meet at school next week.
Toby, Billy and Kyle went to meet Mrs Jones at the car. As they were re-diapered and getting dressed an 11 year old boy came over recruiting for the pastel scouts of America. He was dressed in a pale pink box pleat skirt, white tights, white blouse with brown waist coat. On his feet he had black Mary-Janes. He handed Mrs Jones a flyer as the boys climbed into the car.
Soon the boys were heading home. Mrs Jones took Toby and Kyle home before returning home with Billy.
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Sorry for delay guys...Been busy.
Chapter 9 – Sisters Turn Nasty
As Kyle was re-diapered for bed he asked his mommy about joining the pastel scouts. As she helped him into his pink footie pajamas she said she will talk with the other mommies. Kyle drank his night-time bottle whilst his mommy read him a story. He soon drifted off to sleep.
In the morning Kyle noticed his diaper had leaked and his bed was wet. Needing to pee more he released his bladder coating his crotch in warm pee pee, wetting his pjs and bed more.
Soon his sister Jennie came in to get him up. She took him to the bathroom and stripped him naked. She then told him to strip his bed of his wet sheets whilst she ran his bubble bath. Knowing not to argue he retrieved his wet sheets and put them into the laundry chute. He then washed his plastic nursery print mattress protector with lavender water.
After he was done he went and got into the bath and was washed by Jennie. She always thought it cute how he always got an erection when she washed him.
“Your soldier is at attention you little sissy” said Jennie
Kyle blushed red much to the amusement of Jennie. After his bath she dried him and covered him in baby powder. She took his hand and had him lay on his plastic sheet whilst she got a thick cloth diaper. She lined it with a diaper liner and then surprised Kyle by sticking her finger up his butt.
“Ooh that’s gross Jennie, why did you do that?” asked Kyle.
“You’ll see little sissy” replied Jennie.
What Kyle did not know was she had put a suppository up there. She wanted him to be humiliated whilst they went shopping later. Jennie had to take him shopping for his pastel scout uniform.
After three cloth diapers had been put on him she helped him into thin white tights, his kilt, white blouse and red velvet Eton jacket. He put his white Mary-Janes on and followed Jennie down for breakfast. Jennie made his bottle of milk (which she had laced with diuretic) and fed him porridge.
“Thank you Jennie for helping me out today. Kyle you be good for Jennie”. Said Kyles mom.
Soon it was time to go. So taking Jennies hand Kyle went shopping for his scout uniform. On the way Jennie bought Kyle the largest coke he had ever had. He was so happy that Jennie was being nice to him.
Soon they arrived at the specialist boys outfitters. Kyle met Toby and Billy there along with their sisters. As the boys were measured for their new pastel scout kilts. They fastened differently than their normal kilts, on the right rather than the left. As Kyle was taking off his kilt he felt gripping pains in his stomach. They got stronger then suddenly started to fill his diapers with liquid poop. At the same time hi bladder released torrents of warm pee. He then realised with horror that he had no plastic pants on and watched pee soak through his diapers and down his tights. His butt reflected in the mirror showed the brown stain of his explosion all around his butt and down the back of his legs.
Kyle started to cry as he was so ashamed. Jennie and the other sisters laughed and took many pictures on their phones. Toby and Billy who also had stripped to their white tights where in a similar predicament. The smell was intense and soon the boys were ordered to leave. The boys were taken outside in their soiled tights carrying their kilts. Jennie stayed behind to pay for their uniforms and soon joined the others.
“Guess we better take the shitty babies home” shouted Jennie causing people to look on.
The boys were dragged through the town whilst people stared at the sight of the shameful boys in soiled tights.
When home Kyle had to strip in the garden. His soiled clothes dumped in a large bucket. He stood there naked whilst Jennie turned a hose on him to clean him of the smelly poop. For the rest of the afternoon Jennie supervised him in the garden. He remained naked until half an hour before his mom would arrive home. He had to pee and poop in the garden like a dog.
He was dressed in a diaper and his scout uniform when his mom arrived home. He also had to suc-k on a pacifier and was ordered by Jennie not to say anything or else.
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Chapter 10 – New School and Pastel Scouts First Meeting
When Kyles mom arrived she looked at Kyle in his uniform. She admired his pink skirt and lifted it to check his tights admiring the ruffles on the rear.
“You look very smart Kyle. Where you good for Jennie?” she asked.
“Yes mommy” replied Kyle.
He was told to go upstairs and change out of his uniform so that he could have dinner without spoiling it. He went upstairs and carefully took off his scout uniform and folded it. He put on a pair of his play tights and pink polo shirt and went downstairs for dinner. After dinner he joined his mom on the couch to watch Frozen.
Soon it was time for bed and Jennie offered to get him ready for bed. Kyle was worried she would be mean to him again but she was nice as pie. Gave him a bubble bath and dried and diapered him in 3 night diapers and remembered his plastic panties before helping him into his footed pj’s.
Whilst Jennie was reading him a story his mom entered the room to say goodnight. She kissed him on the cheek and gave him his pacifier and night bottle. Kyle soon drifted off to sleep and his crotch became aware of the familiar warmth as he happily wet his night time diapers.
In the morning after a quick shower and dressing in his new school uniform. His mom took quite a number of photos for the family album and Kyle had to do a number of turns causing the kilt to flare out which Kyle just loved.
Kyle sat at the table for breakfast and was put in a bib so he wouldn’t make a mess. He was handed a new lunch box with the words “Mommies Little Princess Boy” on the lid. His backpack had 4 spare diapers and a spare pair of tights in. Soon Kyle and his mom were heading off to his new school. He endured the taunts of the boys from the other schools clinging close to mom.
Non too soon they arrived at his new school and were soon joined by Toby and Billy. They also saw Wupert (as he called himself) holding the hand of his mommy. He was dressed in pink rhumba tights and “Hello Kitty” top. He was suc-king his thumb and when he saw Kyle, Toby and Billie smiled at them.
The boys were escorted to their class by another student and after being introduced to the class took their seats. The teacher seemed kind and the lessons went well. At break time Kyle, Toby and Billie were taken by their diaper changers (nominated fellow students) to be changed in the assembly hall. All boys were stimulated by the application of diaper cream which did not seem to phase their changers. The boys went to play and soon were joining in skip rope and hopscotch with the other boys.
After lunch the boys went to a new lesson, “Clothes making”. Their first project was to make tennis knickers for their tennis lessons later that year. Kyle seemed to take to it like a duck to water, but Toby and Billy struggled. Soon however they all modelled their new tennis knickers with pride.
All too soon it was home time. The boys hugged each other before setting off home with their mothers, saying they would see each other at scouts later on. After changing into just his diaper Kyle had dinner. Spaghetti was Kyles favourite but he always made a mess.
“Mommy I need to poop” announced Kyle.
“Go ahead dear” she replied.
“Will you take me mommy” asked Kyle.
“No just do it in your dipee dear, you’re messy already” replied his mom.
Embarrassed Kyle pushed poopie into his wet diaper as Jennie smirked.
“Finished dear” asked his mom.
Kyle tearfully shook yes and Jennie was ordered to change him and wash him ready for pastel scouts. Kyle made sure to add to the load before Jennie changed him. It was payback for earlier he thought to himself.
After Jennie gagged a few times he was cleaned up, washed and lead naked into his room. He was changed into his scout uniform and more photos were added to the family album. It was soon time for Jennie to take him to the meeting. She dragged him all the way to the hall where scouts took place.
Entering the hall there must have have been 20 skirted boys running around chasing each other. There were a few shy ones that just sat at the side holding hands with some of the other boys. Kyle saw Billie and went to join him.
Jennie took off saying she would pick him up later.
“Gather round boys” called the scout leader, a man dressed in a black kilt and white shirt.
“We have three new boys joining us today. Kyle, Toby and Billie please join us”
Kyle, Toby and Billy joined the leader at the front. The other boys curtsied to them and they were shown how to curtsey back.
All the boys said their vows and the boys went to join the others. The first activity was surprising, it was self defence. It was explained that as they were special boys they would need to defend themselves against the rough boys and bullies. A look of guilt came over Billies face but he soon joined in.
It was quite a sight boys dressed in pink skirts, white tights with diapered butts doing karate kicks and punches, but at least they could defend themselves if attacked.
The next activity was first-aid, which Kyle loved. He helped Billy into a sling and almost had him picking his nose it was tied so tight, much to the amusement of the others. Soon it was tuck shop time and the boys tucked into all manner of sweets and sodas causing a new sugar high. After diaper changes it was time to go home. The boys did their final curtsey and gave each other a good-nite hug before being picked up.
Jennie again dragged Kyle home and remained totally silent all the way. When Kyle stepped through the door he couldn’t tell his mom fast enough how much fun he had. He demonstrated his karate and asked to put a sling on Jennie, but was refused as it was bed time.
Soon Kyle was drifting off to sleep and was soon soaking his nite time diaper….
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Damage now sorted thanks.
Chapter 11 – Modelling
In the morning Kyle woke to a saturated diaper and wet bed. His diaper had soaked through his pink sleepers and made the bed wet. Soon the door opened and his sister Jennie entered to get Kyle up for school. When she saw the state of his bed she was not happy as she would be expected to change it. However she kept her anger hidden from Kyle as she had plans for the weekend when she would be babysitting her sissy baby brother.
“Oh my poor sweet brother, looks like you were swimming last nite” said Jennie.
“I’m sorry Jenny” replied Kyle sadly.
Jenny reassured him helped him out of his wet things and into the bubble bath she had prepared. He was soon enjoying the warm bath and played with the bath toys that Jenny had sorted for him. Soon he was dried and dressed in his school uniform. His “My Little Pony” backpack was packed with his pink leotard, white tights and ballet slippers for P.E.
Jenny took kyle to school and even stuck up for him against the taunts of the local bullies. Kyle was so happy that his sister was at last being so nice to him. Soon he took his seat in class next to Billy who seemed to be fidgetting a lot.
“Whats up Billy” asked Kyle.
“My diaper is itchy” replied Billy.
Kyle agreed to have a look at diaper change time.
When it was time to change diapers, Kyle pulled down Billy’s tights revealing yellowed plastic pants and a very soiled cloth diaper. Kyle carefully removed Billy’s diaper and was shocked at the smell that greeted him. Billy’s crotch was very sore looking.
“You’ve got bad diaper rash, don’t your mom or sister clean your diaper area Billy” asked Kyle.
Billy told Kyle that his mom was away and his sister wouldn’t clean him and made him stay all day in his soiled diapers. Kyle asked the nurse supervising diaper changes for help. She gave him some special cream to rub into Billy’s crotch. She said that for the rest of the day that Billy was to wear nothing under his kilt and could use Kyles diaper for his pee pees. Kyle said he was happy to help Billy out.
When they returned to class it was announed that at P.E. they would be modelling some new “Unisex” clothes for a new government initiative. Kyle ws excited at this news whilst Billy was more occupied with his diaper rash.
Soon the boys filed into the rec hall for P.E.. At the far end of the hall was racks of new clothes. The boys were told to remove their clothes and put them neatly on their chairs. Soon all boys were happily stood naked and waited in line for the clothes they would model. Each was handed a set of clothes to model.
Kyle first put on a pair of pale blue panties with white lace trim. He then slowly pulled up sheer white tights. He the put on a box pleat skirt with a dinosaur pattern printed on the material. He then put on a pale blue blouse wth gingham edged peter-pan colar. He stepped into a pair of red mary-janes and waited for Billy to change into his outfit. Billy was dressed in red shortals, white tights and similar blouse but with red gingham.
All the boys were shown how to show off the clothes in front of the video camera. Soon they were all prancing in front of the camera as directed until their next change. This time it was the new range of diapers and plastic panties. Billy was excused this but was asked to stay naked as they wanted to do a shot of his diaper rash.
Kyle and the other boys dressed in blue diapers and transparent plastic panties showed them off to the camera before the cameraman asked “Does anyone want to go pee pee for the video”> Kyle shot his hand up along with five others. Kyle stood in front of the camera and in a short while proceeded to wet his diaper. As he wet the cloth diaper darkened and then started to turn pink. Kyle and the other boys were fascinated by this color change. Soon all boys were wetting their diapers and turning them pink.
Billy did some close up work on his diaper rash for the smiling cameraman. He was relieved to be back into his kilt when the modelling was over. Kyle asked Billy if he wanted to stay with them whilst his mom was away, which he readily agreed to.
After going home with Jenny. Kyle and Billy had dinner and a few sodas. After a bath Kyle and Billy got ready for bed. Kyle rubbed the rash cream into Billy’s diaper area causing Billy to sport a little erection. Billy returned the favor to Kyle and soon both boys now had little erections. They giggled as they continued to rub each other.
“Having fun sissy’s” giggled Jenny who had been watching at the door of Kyles bedroom.
Humilated the boys got diapered and climbed into bed. Soon they drifted off to sleep and soon the familiar warmth in their diapers could be felt as both boys peed themselves happily.
Jenny went to bed dreaming of the fun she would have this weekend when she would be alone with her sissy boys...
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Chapter 12
In the morning Kyle and Billy woke up in very wet diapers. The bed had a large wet patch under the boys. Kyle and Billy started to strip the bed and took the wet sheets to the laundry room. Soon the wet sheets and wet diapers in the washer and started the wash cycle. Naked and with firm erections the boys started to wash their plastic pants.
After hanging their plastic pants up they headed for Kyles bedroom to get dressed. On the way they met Kyles mom. Embarrassed by their aroused state both boys immediately covered their crotches.
“Don't worry boys I've seen it all before” said Kyles mom.
“Not mine you haven't” replied Billy.
“Are you sure about that Billy” asked Kyles mom.
The boys giggled and ran into Kyles bedroom and were greeted by Jenny. She had got their clothes out for the day. As Jenny dried and powdered both boys, Kyles mom shouted up to the boys.
“Bye my little princes, be good for Jenny and I will see you both when Billy's mommy and I return”
Jenny said “Should be princesses”
She then handed Kyle and Billy a suppository each. She told them to push them up each others butts. She said it was medicine to help them both.
Kyle asked Billy to bend over and with a little effort pushed a suppository up Billy's butt. Embarrassed Billy and Kyle got erections. Particularly when Billy did the same to Kyle. Jenny noted their aroused state and would use this to her advantage later.
Next Jenny had the boys lie down for their diapers. Kyle was the first to be diapered. Jenny wrapped 3 thick cloth diapers around his waist and secured them with large safety pins. She then pulled white lacy tights up his legs and around his waist. He was told to sit on his bed whilst she diapered Billy. As with Kyle, Billy had 3 diapers secured around his waist followed by white lacy tights.
Jenny then helped Kyle into pale blue short shorts that had two white pearl buttons on each of the legs. He was then helped into a pale blue sailor top. Finally he was helped into shiny black patent leather Mary-Janes. Billy was attired the same and both boys were told to hold hands whilst Jenny took their picture. Reluctantly both boys complied.
“Right little sissies, time to take you both shopping and show you off”
Kyle and Billy didn't like the sound of that, but knew that they had to do everything that Jenny said, so they both followed her, holding hands as instructed by Jenny.
“Skip my little sissies” shouted Jenny as they left for the bus stop.
Kyle and Billy skipped along half heartedly almost crying with embarrassment. They soon arrived at the bus stop along with Jenny. There were a number there old school friends waiting for the same bus. Seeing Kyle and Billy dressed the way they were invited the inevitable giggles and taunts.
As they waited for the bus the suppositories started to take effect and soon they both were trying to hold off the forthcoming soiling of their diapers. It was also at this time that Kyle realized that their diapers were not protected by plastic pants.
Kyle whispered to Jenny “Jenny I need to poop and we are not wearing plastic pants”
Jenny smiled and said “You have to earn plastic pants for YOUR DIAPERS!”
Both Kyle and Billy blushed deep red as they were now the center of attention. Soon both boys lost control of their bowels and filled their diapers with watery poop, They also flooded their diapers with pee. Inevitable the evidence of their soiling showed on their shorts and down their tights.
“Pew they stink” shouted one boy.
“Look at the babies they done stinkies in their sissy clothes” jeered another girl.
“Oooh my you can't go on the bus like that” smiled Jenny.
Both Kyle and Billy were told to strip out of their soiled shorts and tights, much to the disgust of their audience. Totally humiliated they stripped down to their filthy diapers. Jenny then handed them both pink frilly plastic pants to put on and then clean lacy anklets to put on their feet.
The poop in their diapers was starting to sting and both boys had to carry their soiled shorts and tights in transparent plastic bags. Soon the bus arrived and they took their seats and tried to cover their plastic pants. Again they were the center of attention and all this was being recorded on Jenny's smart phone. She planned to share all the footage on Youtube. Revenge was sweet she thought to herself.
Soon they arrived in town and Jenny took the boys to Mc Donalds and made them drink 3 large cokes. Jenny told them to let her know when they needed to peepee again so she could capture it.
After Mc Donalds they went to the “Little Princess” girls dress shop and were subjected to trying on the girliest dresses Jenny could find. They came out dressed in two of the dresses Jenny had chosen along with new tights and frilly anklets. The petticoats and dresses were short enough to reveal their thick and soiled diapers that were now being added to. Kyle and Billy spent the day being paraded around town in very soiled diapers that were making them very sore and every step painful.
They were glad to be heading home with the hope that they would be cleaned up and put into dry clothes. Soon they arrived home and Jenny told the boys to get into bed. They were to go without dinner as they had been such babies during the day. Kyle and Billy went to bed crying both out of embarresment and pain.
Jenny busied herself posting the footage on YouTube. She looked forward to tomorrow when she could torture her sissies more. Footage posted she went to bed to dream of what she could do next whilst Kyle and Billy had a fretful nite trying to get comfortable in their overly soiled diapers.
The next morning Kyle and Billy woke together. The bed was soaked and stained brown from the contents of their diapers. The diaper rash was now severe and the boys whimpered in pain waiting to see what the day had in store for them.
Kyle was the first to spot his mom at the door of his bedroom. She had returned home early after seeing footage from YouTube that one of her friends had sent to her. Seeing the state of the boys she burst into tears.
“Kyle, Billy, come here and lets get you cleaned up. I'm so sorry this happened to you my little princes”
Soon Kyle and Billy were in a hot bath enjoying being cleaned up. Though the pain of the diaper rash was hurting. As they bathed they heard Kyles mom and Jenny arguing. They gathered from what they heard that she was grounded and would be further punished. Soon Kyle and Billy were being gently dried and rash cream applied copiously. They were told that for the weekend they would have to remain naked from the waist down to help sooth their diaper rash. They also would be helping to punish Jenny and had to come with some ideas ;)