For all of his youthful life, Timmy's mother Donna had molly coddled him and encouraged his love for girl's panties and clothing. Perhaps it was because she'd never had a daughter of her own that she did it, but in any event, Timmy was dressed as a little girl more often than not, and he grew up becoming ingrained with his naturally sissy ways.
This would have probably gone on indefinitely, except that Donna received an excellent offer to do some work in a foreign country that she couldn't refuse. While it meant a huge financial boon to their cash-strapped family, unfortunately, one of the stipulations was that her son Timmy would not be able to accompany her. She was devastated to be without her little "girl" Timmy, but it was a temporary sacrifice she was willing to make.
As fate would have it, her sister Alice lived nearby and she expressed her willingness to have Timmy come live with her. Alice was aware of the way Donna treated her son and while she had her own ideas about how a little boy should be raised, she agreed to become his guardian, provided he would be willing to live by her rules. Donna could find nothing at all wrong with that so she quickly accepted the job offer and thanked Alice for her graciousness.
As Alice accepted her sister's praise, she assured her sister on the phone that Timmy would come to love his new home.
Timmy, for his part, was not so sure. He knew his aunt was a total hottie but he also knew her to be rather strict and set in her ways. He was used to getting his own way around his mom's house and he doubted that his aunt Alice and he would see eye to eye.
Later that week, Timmy arrived at his aunt's house, hoping to resume his pampered life as a sissy.
Unfortunately, he was due for a rude surprise. Alice had her own ideas about how to raise a sissy and the first thing she told him was that he would be expected to wear diapers and plastic panties to bed every night. Timmy threw a hissy fit and that was when he found out just how Alice settled arguments.
That turned out to be just the first of many humiliating spankings, administered by his strict aunt for seemingly trivial offenses. And he soon learned of another one of her traditions, which was to give him a long, hot soapy enema once a week "just to keep him pure"--whatever that meant. His aunt certainly had her own ideas about discipline and she enforced them rigidly with an iron hand.
He also began to notice that the dresses she bought him tended to be more and more babyish as time went on. He pouted for the entire morning when Alice presented him with a cute white party dress and matching panties.
Alice's friend Heather, thought he was just the cutest little thing and she often told him what a pretty little sissy he was.
Timmy was very shy around her but he actually began to resent her when she suggested that Alice "lower his age" to that of a baby whenever she happened to visit. She thought his diapers were simply adorable and she insisted on having him put into them whenever she came over to babysit. Alice was easily convinced that this was all for Timmy's own good and he soon acquired a vast layette and wardrobe of babyish clothing. Heather suggested to Alice that she make the emasculated sissy take naps during the afternoon and once again, her suggestion quickly became policy.
One day in August, Alice got a call from her sister informing her she wouldn't be able to come home for possibly a couple of years. Was she still willing to look after Timmy? Alice assured she was and that things had worked out wonderfully for her sissy son. Donna was beside herself with relief and she thanked Alice profusely for everything she'd done, promising to make it up to her some day.
So it was that as time went on, Timmy was forced to become more and more of a baby, wearing his embarrassing outfits all hours of the day. And as he grew older, he became resigned to his humiliating treatment and even came to secretly love the soft, comforting embrace of his thick sissy diapers. He soon discovered he was quite incapable of resisting the urge to masturbate in them and his private time was often dedicated to satisfying his sexual needs.
And so it came as something of a shock when his babysitter Heather calmly informed him that she was aware of his habit of playing with himself and that she had every intention of telling Alice when they got home.
Timmy was mortified as he looked over at her smiling face and he blushed furiously as she went on to explain her plans for how best to deal with "his problem".
Two days later, he found out firsthand the reality of Heather's idea. After his morning diaper change, but before Alice had dressed him for the day, he was fitted into his new chastity device, a CB6000s, the 's' being for 'short shaft'.
Timmy quickly found out he would no longer be able to play with himself, or even get an erection so long as the cruel device remained locked in place. And Alice assured him it would be his constant bitter companion for all time, only coming off long enough for cleanings before she locked it back in place with her titanium lock. Frustrated and angry, Timmy threw a tantrum but it got him nowhere. Stamping his feet and balling his fists in defiance, it was only a matter of seconds before he found himself over Alice's lap, feeling the harsh slap of her ****en paddle. It was a sorry, bawling sissy who found himself being diapered and dressed that day with a scorching hot bottom that wouldn't be going away anytime soon.
Timmy found his enforced chastity nearly impossible to deal with, and of all Alice's humiliating rules and requirements, this one was surely the most difficult. It wasn't made any easier by the fact that she liked to saunter around the house in just her underwear and Timmy often found his little penis throbbing painfully while in her presence.
One day, he walked into the living room to find her lying on the couch watching TV. He had decided it was time to beg her, using every argument he could muster, to unlock his poor captive wee-wee, if only once.
She looked up from her show to give him a look of annoyed disbelief.
"Not in a million years, sissy boy," she said flatly, "Your chastity is going to be permanent--better get used to a life without cumming ever again."
....to be continued(?)