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Sex Story Sissy Boy

Sentenced to a Life Of Diaper and Petticoat Punishment (Submitted by Baby Penny)

The cure for this ‘boys’ bad behaviour was to be placed in the ‘care and control’ of Auntie Tina who knew only too well how to ‘deal’ with naughty little boys who spent too much time ‘playing with themselves’ rather than making an effort to grow up……..

Now instead of spending hours on the internet searching for disgusting sites leering over pictures of naked Ladies….he spends his time in very different pursuits………

Once an adult male called Ian this ‘disgusting and dirty’ little boy was to become Penny… obedient, devoted and diapered little girl……who would learn to accept the many painful punishments and humiliating assignments which were part of his ‘Sentence to Sissihood’ a programme of ‘Behaviour Modification’ which would now be supervised solely by Auntie Tina.


‘Penny’ as she was now to be called would, in time, learn to accept her new life as Auntie’s very own Prepubescent, Panty Wetting, Little Baby Girl completely dependent and utterly vulnerable……….to any and all Grown Ups who were ‘invited’ to witness her ‘training and tuition!’

Penny’s Programme - Diaper Discipline, enforced Petticoat Tuition, Private and Public Punishments, strict Dress Codes, Personal and Domestic Task training, complete Financial Control and Dependency assisted by constant ‘supervision and humiliation’ all these were aspects of a Disciplinary Programme designed by Auntie to assist her in the creation and ‘application’ of a programme which would , once and for all, strip Ian of any ‘male arrogance or aspirations!’

First his name was ‘taken away’ from him…and replaced with the more appropriate name of Penny Pee-Pee.


Ownership Mark - Her first trip out with Auntie Tina and Auntie Donna was a late night journey across town……to a Tattooist…a Ladyfriend of Auntie Donna.This was to be her first shameful ‘indignity’ Penny was stripped completely by Auntie Tina. Forced to walk naked between her two Aunties down the dark corridor they entered the ‘parlour’ where the Lady to a table in the middle of the room.

Penny was then instructed to climb up onto the table and her ankles were secured u p in the slings. Her wrists were then secured to the side of the table so that she could not move. The Lady then proceeded to apply a previously agreed ‘design’ just above Penny’s little bits and pieces ensuring that her ‘identity’ would never be questioned again……

By the time Penny was taken back home by Auntie Tina and Auntie Donna Penny had been ‘marked’ permanently……. On her shaven panty area at the front for all to see was tattoed

Baby Penny


On her botty was tattooed…..

This Baby belongs to Auntie Tina

These shameful ‘marks of Ownership and Identity would now be with her for life…….like the diapers on which she would eventually be forced to rely…..

Baby Pants and Waterproof Panties - Penny was then ‘introduced’ to her new ‘undies’….and sternly reminded by Auntie Tina that from this moment on….she would only be permitted to wear a mixture of thick nappies, disposables and ever present waterproof Babypants…….

No more boxer shorts…..not even pretty little panties…..just ‘nasty naps’ from now on…..a life sentence… a result of her previous disgusting and compulsive habit of ‘playing!’

In this way Auntie’s Little Toy would be constantly ‘protected’ from any attempts to ‘misbehave’ by being ‘humiliatingly imprisoned’ under layer upon layer of fluffy towelling and ‘noisy’ plastic panties.

Modesty and Privacy were two Adult Privileges which Penny would no longer ‘enjoy’ Like all other Adult Privileges and Pleasures these were among the list of ‘luxuries’ which had been ‘suspended permanently’ in an effort to ‘regress’ Penny thoroughly into her new life as Auntie’s Baby Girl…..

Puberty Rule - Forbidden to display any signs of Puberty..Penny’s panty area was constantly ‘inspected’ and thoroughly shaved keeping her in a permanent state of Prepubescency…..and also making nappy changes that much more hygienic.

It was always a pleasure to be able to ‘show off’ her Prepubsecent state as well as her Ownership and Identity marks at nappy changes!!!

Potty/Panty Training - Forbidden to use any Grown Up toilet ever again….Penny now has to learn to ‘recognise’ her toilet needs and quickly find a Grown Up and ask ‘nicely’ for her potty…..Of course if the request is not considered ‘polite enough’ the request is always denied and in this way Penny is ‘sentenced’ to a ‘nasty nap!!’

‘Potty or Panties’ was the only choice for Penny….and Auntie insisted on her learning this from day one……

If it was not convenient for Auntie or another ‘supervising’ Adult to supervise Penny on her potty…..then she would ‘re learn’ the skills of ‘panty wetting and messing’ The shame of having to remain in them until an Adult was inclined to ‘grant’ a nappy change was a very shameful and humiliating experience for her.

In the initial stages of her training Auntie Tina locked the potty away and in doing so forced Penny to ‘re learn’ the skills of ‘using’ her nappy properly…..Long periods were spent in ‘nasty naps’ until Penny came to accept the fact that this ‘practice’ was the normal situation for her and that ‘potty was a privilege’ which could only be earned by good behaviour and effort.

An effective punishment which Auntie often used to ‘instill’ better behaviour in Penny was simply to ‘lock the potty away’ for days at a time….sentencing Penny to the cruel prospect of using her nappies for all her ‘natural’ needs……just like a real Baby forcing Penny to endure the cruel torment and ridicule of visiting Grown Ups

Accepting that ‘diaper and potty training’ were now to become a daily and constant ‘task’ was very difficult for Penny…..but the constant supervision of Auntie and her friends prevented any kind of ‘avoidance’ of this necessary ‘skill acquirement.’

Over many months Penny would learn to ‘perform in her potty’ if she had been a Good Little Girl or suffer the indignity of ‘performing in her panties’ as a consequence of any hint of disobedience.

Learning to ‘squat like baby’ infront of guests when no potty was available would be a frequent occurrence…..enabling Penny to complete her ‘pooh’s or pee-pee’s’ satisfactorily for any supervising Adult.

The removal of ‘toilet privileges’ and the ‘lack of any privacy or modesty’ at such times re inforced the ‘inevitability’ of Penny’s Regressional Programme….

The continual ‘shame and humiliation’ caused by this aspect of Penny’s training.helped to create a more ‘docile’ child…..more compliant and definitely more obedient……traits which were considered by Auntie Tina as extremely desirable and absolutely necessary.


Dress Code - Gradually Penny’s Grown Up clothes were replaced with more and more dresses and petticoats. Auntie insisted on a rigorous ‘dress code’ at home…

Penny’s programme of Petticoat Discipline meant that she was required to be dressed in her pretty little dresses and petticoats at all times for Auntie…..the wearing of Adult clothes was strictly forbidden to Penny once she was home from work.

Domestic and Personal Training - Despite being dressed in this way Penny was ‘trained and taught’ to carry out a whole range of Domestic Duties….ensuring that Auntie’s home was always kept spotless. Although Penny was forbidden to use the Grown Up toilets at any time……she was nevertheless expected to scrub and polish them regularly ensuring that they were immaculate for Auntie and her guests.

It was ironic that Penny’s potty was always kept on ‘display’ on the floor next to the Grown Up toilet. It even had her name on it!!!!!!

Auntie Tina often had guests over in the evenings or over night….sometimes Penny was permitted to ‘stay up’ at such times merely to perform various duties such as ‘waiting at table’ or ‘fetching and carrying’ drinks for her friends but at other times it was considered Adult time and as such Penny would be locked in the Nursery upstairs sitting at her little desk with a Punishment Gag strapped into her mouth writing out lines or Punishment Essays to ‘keep her busy’ before bedtime.

If Auntie had enjoyed an evening dinner party with guests Penny would be brought down from the Nursery and ‘paraded for their pleasure’ in front of all her guests and then sent into the kitchen to ‘wash up’ and clear away while the Grown Ups relaxed in the lounge.


Corner Time - If Penny had been especially ‘naughty’ Auntie would place her in the corner ‘on display’ for all her guests as a form of ‘public humiliation.’ She would have to remain in the corner and to keep her there Auntie would place a pair of her ‘dirty panties’ between Penny’s nose and the wall…..and she would be warned about the consequences of letting them fall to the floor!!!

What made this particularly difficult for her were the constant ‘examinations’ Penny was forced to suffer as Aunties guests explored her petticoats and examined her nappies….increasing her shame immeasurably and at the same time ensuring the ‘pleasure and amusement’ of all the guests as Penny was teased and tormented about having to wear diapers and petticoats ‘at her age!’

As well as learning to carry out Domestic Chores Penny was taught how to ‘satisfy’ Auntie by being taught to perform a range of Personal Duties for her……

Toilet Training

‘Special Feeds’

‘Toilet time’ was a special ‘moment’ for Baby and Auntie….A special Feeding Funnel was used and this was strapped into Penny’s mouth at such times…She was made to lie on the floor and ‘demonstrate her devotion’ to Auntie by drinking all of her ‘Golden Juice’ as she knelt down over the funnel to ‘feed’ Penny……

Penny was taught that this was a very special ‘privilege’ and over months she learnt to accept this ‘Duty and Privilege’ as such……

Every morning Auntie would come into the Nursery and before releasing Penny from her ‘cot straps’ the funnel would be strapped into her mouth so that Auntie could give Penny her ‘morning feed’ before sending her downstairs to make Auntie’s morning coffee for her.

The ‘Morning Feed’ was always the strongest as it had been in Auntie’s ‘tummy’ all night and in the early days of her ‘sentence’ Penny hated it……but she was trained by Auntie to ‘accept and love’ this each morning and politely thank Auntie afterwards.

‘Toilet training’ was eventually extended to Auntie’s closest friends such as Auntie Donna who sometimes ‘gave Penny a feed’ in this way when she was staying over……..



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