Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: derry on January 03, 2018, 05:29:42 PM
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Rosemary and Dorothy held their children’s hands. Rosemary explained:
“They are cousins not actual twins. Both are a bit tall for being 10. Billie is quite mature for her age. Bobbi is a bit immature.”
The two of them did look similar. Both looked like pretty typical girls for England in 1960. Both wore pig tails. Billie wore heels. She looked like having the same height. Actually Bobbi was five foot and Billie only four foot ten.
The lady in the girl’s department smiled.
“Harriet will see to them, the changing room is that way.”
‘Bobbi’ was terrified.
Robert Porter looked on the outside a LOT like his cousin. However he had what his aunt and cousin’s insisted on calling a ‘tinkle thing’. He also had different underwear to his cousin. He was actually 16 but short for his age.
(do people want to hear how this situation came to be and Bobbi's further experiences?)
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I would love to hear more. I'm guessing that Robert aka Bobbi has or soon will have some pretty little boobies. I really love stories where the hero is fitted for or has to wear a bra.
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Sorry boobie is in the sense of stupid, like a boobie prize. Babies and LITTLE girls do NOT wear bras
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Derry, now you have whetted my appetite I would love for you to continue.
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Oh yes, please continue!
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Robert was an only child. His mom had let him get away with stuff. It got worse when his dad died. He managed to buy build up shoes to look taller. He tried to be super macho. He was very aware of his short stature.
His Mom, Dorothy, found a job in England. They could live more cheaply with his aunt and her girls.
Billie was a very girlish girl. Rosemary had worked in very manly ways during the war. She felt women could be as strong and good as men. Rosemary was a bit disappointed by her youngest.
On the other hand Alexandra, who often called herself Al, was a super tom boy. She was a year younger but 4 inches taller than her cousin.
A few years earlier they had visited the USA. Billie had struggled with her cousin’s name. She had called him Boobie instead of Bobby.
Robert was sure that as a boy he should not do “girl’s work”. Rosemary was very insistent. Dorothy agreed that her son should do the dishes.
Robert was very resentful. He did not do a good job with the dishes.
One afternoon Dorothy and Rosemary were out with little Billie.
‘Al’ noticed that her cousin had not done his job. She reminded him twice. He ignored her.
Alexandra knew what happened when she disobeyed her mother. It was half past nine in the evening. Half an hour earlier she had talked to her cousin.
“This is your last chance WASH THOSE DISHES.”
Robert watched television, rather loudly and in fact disrupting Al’s studies. She turned off the television.
“What the f***k are you doing he asked?”
She responded. I need to deal with a naughty child.
Fifteen minutes later the front door opened. Dorothy was shocked by what she saw. Her son was crying and kicking over her niece’s knees.
At breakfast the next day Dorothy had an announcement.
“Robert from now on until you learn to do ironing and other housework you will do ALL the dishes.”
It got worse.
“When neither I nor Aunt Rosemary is around Al will babysit both Billie and Bobby.”
For those weeks of June 1960 a lot of the time Al took charge. Now technically the boy’s uniform could be short pants. A few boys in the secondary school first year (like 11 and 12) wore such trousers.
Robert was not careful with his clothes. He managed to get his trousers muddy and torn.
He had also often been late.
One morning Robert was shocked when he was given his uniform. He was in short trousers. Alexandra insisted on holding his hand.
Robert was also mean. Now for a few weeks little Billie had a problem with an infection. She had a number of wet beds.
Lots of Billie’s little friends were with her. She opened gifts. Robert gave her a rather large looking gift. She cried when she saw that her gift was nappies.
Alexandra gave her boy cousin a severe spanking. He then took visits over his aunt’s and his mom’s knees.
A few days later thing changed a LOT. Billie saw what was happening. Robert had found ways of spying on her sister in the bathroom.
Bobby’s Mom agreed with Alexandra’s suggestion. On Saturday morning he had a HUGE pile of dishes to wash. He hated doing “girl’s work”.
That weekend he did not have to wear short pants. Instead he was in one of Al’s old uniforms. The gray socks were knee length. The skirt, jacket and blouse were all pale blue. He also had to wear an apron.
As he washed the dishes with a sore bottom Bobbie thought that things could not get worse. He was wrong
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Thank you!
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The long summer holiday started. Alexandra talked to her Mom and her aunt, Boobie’s mother.
Alexandra talked to her cousin.
“I do not think you should wear my uniform during the summer.”
Bobby responded:
“So I get to wear pants!”
Alexandra smiled
“Oh no, we need to get you NEW clothes made.”
Now Robert did not have visible face hair. His hair was quite long. Alexandra brushed the hair. She then put it into a pony tail with a ribbon bow.
Then she quietly chatted to Billie. She LOVED the idea of joining them.
‘Al’ wore jeans, her hair was quite short. She held her cousin’s hand. People who did not know him would likely think that ‘Bobbi’ was a school girl.
The American boy allowed his cousin to lead him to the bus stop. They took 2 busses.
The 15 year old Alex asked her little sister to knock on the door. She did so.
Bobbi/ Robert recognized Molly. He had been trying to date his pretty feminine classmate.
Molly beamed.
“Let’s measure you for your new clothes.”
Molly was doing very well in her needlework class. She aimed to be a fashion designer. Alexandra explained:
“Billi is quite mature for a ten year old. Can you design something quite mature for her? Bobbi on the other hand is rather immature for age 10.”
Robert who was 16 did not like the sound of this. Alexandra continued:
“I brought some of Billi’s older clothes. Could you do something similar that will fit Bobbi?”
Molly took Billi into her bedroom and measured her carefully. The long dress would make her look maybe 16. Molly managed to find a push up padded bra for the smart 10 year old.
Bobbi’s experience was different. All the girls watched as Molly undressed him. There were giggles as she commented on his
“Little man it is SOO VERY LITTLE.”
Three days later they returned.
Billi loved her new outfit. You could believe she was 17.
Bobbi’s experience was different. He allowed himself to have a pink camisole vest lowered. The panties were cotton and had mini mouse cartoons on them
Then Molly giggled as she lowered his dress:
“See you can be like a movie star?”
The dress looked like one Shirley Temple had worn age about 8 trying to look 4
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Billi had an idea.
“My friend Sarah’s sister has her 4th birthday party tomorrow. If Bobbie is a good girl maybe he can go.”
The next morning Bobbi was good. He did NOT want a sore bottom. He washed all the dishes.
Billi took his hand. This time she was wearing jeans as was her friend Sarah.
Sarah’s sister, Sophie, was dressed in a style very much like Bobbi. The funny thing was that Bobbi quite liked looking pretty. He played with the Sindy dolls (a British version of Barbie).
He did look a little silly. The little girls giggled.
In the next week or two he went from being a bad boy to being a good girl.
Dorothy and Rosemary agreed.
“Both Billi and Bobbi should have new clothes for their birthdays.!”
Bobbi threw a tantrum:
“Molly will tease me. I do not want kids at school to know what I wear. If you make me go there I will LEAVE school.”
It was late August. Rosemary saw an advertisement. It was for a sale at a Department store. The store was in a town 20 miles away.
Robert agreed to go to the store. Now Robert remained a coffee addict. He had drunk a LOT of coffee.
Just before they were due to go he went to the bathroom. Dorothy asked Rosemary:
“What if he need the bathroom whilst out.”
Rosemary responded:
“Well women would not want a male, even in a dress in their area. I have an idea. We could take the 1.30 instead of the 1pm train”
Rosemary left the house for a few minutes. She went to the Boots pharmacy store
Robert threw a tantrum. He needed a VERY severe spanking. However he was overpowered.
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They had to take two trains to get to the town with the big department store, Bobbi was NOT comfortable. He hoped people would think he was a girl. It was better than them guessing he was 16 and dressed as an 8 year old girl.
His mother and Alexandra held his hands firmly. They just missed a train connection.
The boy in pig tails found himself fidgeting violently. Billi went to the ladies toilet. She then smiled at her cousin. He looked VERY uncomfortable.
Just before the new train arrived Bobbi stopped fidgeting. His mother saw the expression on his face.
Bobbi thought back 40 minutes. He wondered if he had drunk too much coffee. The worse part of this was that in some ways he was grateful that his underwear was NOT what an 8 year old girl would wear. He remembered the shock when he found out what would happened
Rosemary had used old fashioned words. He was not worried when she talked about ‘napkins’. He had kind of assumed that his younger cousin had her period. He was not very interested.
Just before they were due to leave for the train his aunt laid out the terry cotton squares. He suddenly realised they were DIAPERS. He flatly refused. Both his aunt and his Mom had spanked him severely.
They had held him down. It was Alexandra who pinned the didies on him. He had plastic panties pulled over them.
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Rosemary led the explanation in the store.
“Bobbi is not actually a 10 year old girl. Have you heard of petticoating as a discipline method?”
Harriet giggled.
“Well Bobbi looks like an adorable girl.”
He stamped his Mary Jane sandals. Aunty talked to Dorothy.
“I think Billi should get her new things first.”
Dorothy held his hand. Other customers noticed ‘the girl’ again violently fidgeting. His mom was glad that the two nappies had been pinned on and that the kite pattern would concentrate absorbency where it was needed.
She whispered :
“I did bring a diaper bag.”
He felt the nappies getting wetter.
After half an hour Billi came out. She had decided to be a tom boy. She looked like she could be 16
Dorothy led her son into the changing room in the girls’ department. Alexandra joined them. It was a relatively large changing room.
Al (in jeans like her sister Billi) unbuttoned her cousin’s dress.
Alexandra explained, well he could not use a girls toilet and we could not trust him on his own in a boys bathroom.
Harriet, the 18 year old store clerk, fought hard and avoided giggling as she saw his soggy sagging nappies. She whispered to his mother
A few minutes later she returned and put some old newspapers on the bench.
“I think someone did need a CHANGING ROOM.”
His Mom laid him on the bench. She pulled off his plastic panties. Alexandra unpinned the nappies. She held up the heavy soggy nappies. She put the diapers into the waterproof section of the ‘diaper bag’.
Then his mommy held Bobbi’s legs up. Alexandra wiped him. Harriet commented:
“What an adorable LITTLE man he has.”
As his cousin wiped him the little man got a little bigger. Alexandra commented
“I think Bobbi does LOVE err NAPPY time.”
Then his cousin smothered his manhood with clean nappies.
Harriet looked at him, just in the nappies and a camisole.
“I wonder if there are dresses that might go better with your new underwear.”
She left the changing room. 10 minutes later she returned.
Harriet had chatted to a girl in the maternity department. Molly had heard some ladies compare that some of the maternity smocks made them feel like they were children or babies.
Alexandra smiled. His mom and his cousin had to restrain him to get this particular dress on Robert. He saw in the mirror. It looked a little bit like a baby dress. It certainly made the diapers VERY conspicuous.
Harriet then sorted out a different dress. It was like pinafore or jumper dress. It looked like it was designed for a 5 year old but in his size. It was however long enough to hide his diapers.
Alexandra asked:
“Would you like your Mommy to ask for THAT dress, curtsy and say pretty please.”
Bobbi curtsied and said pretty please for a dress that most 8 year old girls would feel super childish.