A Painful Adjustment
A confirmed sissy finds his new home not what he expected
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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(?)



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clarisselovelace
Man. Sissy is going to have to change her name to blue balls.
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bubblebutt
please pelase do countine
plump and soft
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Mellsissy
Ouch that would stink. But a great story.
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francescd
Wonderful story, sweety.:)
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diapered_tristan
great story cant wait for more 
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c2bear
Great story so far and good choice on the images. Hope you will continue the story 
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babie
ou loves that paddle hope i am next
likes my fanny in warm hands and to be foundle by anyone you would like to play .
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Mina Silverwind
I love all of these, the story behind them is excellent, and thanks for sharing all of your fantastic work with us.
success is not how many times you win but is instead our ability to learn that we win by never giving up when times are tough.
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DiaperDreams
oh i wish i was him
It shouldn't matter whats between your legs but instead what is in your heart.

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Katie_Babygirl23
very nice I can't wait for more
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Daddy Bradley
Nice story. Alice and Heather are true beauties. Please continue.
Look pretty for Daddy!
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marcorpsdoc
Contiunance?
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babyjessie
Yea, Will you continue?
Lots of tight and long hugs!
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BabyDiana
This was really good. Please Continue!


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Baby Bobby__
Timmy's life became one of anxiety and frustration. It seemed like every day found him hornier and hornier, desperate to escape the cruel embrace of his chastity device. His thick, prissy diapers mocked him with their softness every time he stroked the shiny plastic front of his waterproof panties. And while his aunt Alice had stocked his dresser with them in all manner of colors and styles, he found the nursery print styles to be the most humiliating.



They were so inherently babyish that there was no way anyone would confuse him for someone with a medical problem. No, his nursery print plastic panties guaranteed that anyone seeing him would realize he was a full blown sissy baby.

But that was really not the biggest of his problems. His biggest issue was trying to deal with his inability to masturbate--an activity that he had engaged in with such enthusiasm previously but was now denied because of his accursed chastity device. Try as he might, he could not achieve any sort of orgasm, no matter what he did and it was maddening for the horny sissy.

Alice's friend, Heather, often babysat when his aunt was away but Timmy found her to be a mixed blessing.

On one hand, Heather was always kind to Timmy, indulging all his sissy desires and doting on him like he were her own baby girl. On the other hand, Timmy found her voluptuous figure more than he could stand and as would happen so often, he'd find his tiny penis straining painfully in his chastity device as Heather played with him or changed his wet diapers. She seemed totally oblivious to the effect she had on him and she'd smile angelically while Timmy gazed at her pretty face, amazing figure and cried tears of frustration.



He wanted so badly to rush into his nursery, as he used to do, and masturbate furiously to the delicious visions of Heather swimming through his mind. And while Heather was the friendliest and most accommodating of all his babysitters, she fully agreed with aunt Alice that sissies had no business masturbating or getting erections.

"I'm sorry Sissy," she tell him in that soft, sultry voice of hers, "But babies like you shouldn't be playing with their willies. You'll just have to think about something else."

Of course, it was quite impossible to think of anything else, with Heather sauntering around in her clinging tops and uber-short shorts.

One day, when Timmy was climbing the walls with unrequited sexual frustration, he begged Heather to have mercy on him. Seeing the genuine tears of angst trickling down his face, she couldn't help but feel pity for the poor diapered sissy.

"Awww, I'll bet you're just as anxious as can be, with your tiny little thing locked up, hm?" she asked in a voice reserved for toddlers.

He nodded his head and renewed his desperate pleas for relief from his stunning babysitter.

Heather smiled down at him and took his hand, leading him over to the sofa in aunt Alice's living room. Wordlessly, she slowly unbuttoned her clinging top and set it aside, revealing her tremendous milk laden breasts to the dumbfounded sissy.



"Since I had my own baby a year ago, I'm finding that I'm still producing more milk than my little one can accept...and since you've been such a good little sissy for me, I think you've earned a special treat."

Timmy gaped in amazement as Heather undid her bra and let the sensuous cups fall away from her heavy mammaries. Taking Timmy across her lap, she gently brought his quivering lips up to her firm, dribbling nipple.

"There you are, Sissy,' she whispered, "Suckle like the big baby you are..."

Timmy closed his eyes and accepted her warm, welcome nipple into his mouth. As her milk began to flow, he tried to ignore the throbbing pain in his implacable chastity device...
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babyjessie
I agree! It's a great addition, but please dont just leave it at that! I can't take it anymore!!!
Lots of tight and long hugs!
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bubblebutt
she is evil but know one would ever know
plump and soft
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red
That's a big momma
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straightsissy13
Isn't that everyone's secret dream haha :)
PAINT MY TOES AND CALL ME GABI
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Flyff
Wow, I haven't read a story this good since sissybekcy's site was taken down. Nice.
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koharu
please post maor
lalalalalalala
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Puppy Amber
Please, please write more!!!
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Baby Bobby__

One weekend, aunt Alice was busy with errands and she left Heather to babysit Timmy.

As Heather was tenderly diapering Timmy for the day, she told him that she was going to invite some of her friends over to work on their tans by the pool. The prospect of being seen by a number of adult females made Timmy extremely nervous and he squirmed on the changing table as Heather removed his damp, clinging plastic panties.


"B-but...won't they see me in my d-diapers?" he quivered tremulously.

"Don't you worry about a thing, my little sissykins--I'll put you in a cute little outfit that will be sure to hide your diapers," she re-assured him.
Timmy wasn't so sure and he grew even more anxious when she pulled the short pink baby dress over his head and buttoned it closed behind him.

"You see, Timmy--you have nothing to worry about," she said with a confident smile, "You'll just have to remember to be careful about bending over."




Timmy pouted and fidgeted as he toddled about across the floor.

"Are you sure no will see them? I don't want anyone to know that I wear diapers," he whined.



Heather giggled and gave his nursery print covered bottom a playful slap.

"Relax Timmy--You have nothing to worry about," she told him with a giggle.



An hour later, Heather's friends started to show up. The first to arrive was Jessica who grabbed a spot by the cooler and sat down on her beach towel. When Heather nudged Timmy to go over and introduce himself, he could barely manage to face the attractive blond.


"Well!--you must be Alice's little sissy boy!" she exclaimed cheerily.




Timmy blushed hotly even as he tried unsuccessfully to avoid staring at her succulent bosom.

"You remind me of my three year-old niece," she continued, "She's still in diapers too--just like you."
Timmy's face flushed even redder as he desperately pulled the short hem of his dress down.
"I-I'm not wearing d-diapers," he stammered but the amused smile on her pretty face told him he wasn't fooling anyone.

The next one to show up was Heather's busty friend Susan. Timmy had met her before and he knew her to be rather cruel, and none too sympathetic to his unique situation. When the others were distracted, Susan came over to where Timmy was sitting on his baby blanket and as she towered over him, she bent forward to look down at the nervous sissy.


"Your aunt told me she locked up your tiny little penis to keep you from playing with yourself," she told him evenly.

Timmy squirmed on his blanket but said nothing, preferring more than anything not to be the focus of her attentions.
"I think all sissies should have their peckers locked up," she continued to lecture him, "lord knows how often you masturbated when she had her back turned."
Timmy was hoping Heather would come out of the pool and rescue him but she was completely oblivious to his little crisis.
Bending forward, Susan held her big melons in her hands and squeezed them before Timmy, taunting him mercilessly with an incredible display of her fabulous breasts.

"I'll bet you wish you were allowed to touch these--don't you Little Miss Priss," she said in a mocking, condescending tone of voice.



Timmy sadly nodded his head. His poor caged wiener was throbbing painfully inside his diapers and he knew he'd have a hard time trying to forget this image of teasing womanhood.

"Ha ha!" she laughed, "Not in a million years would I let a sissy baby like you touch these."



Hot, angry tears of frustration blurred Timmy's vision as he shifted and tried to alleviate the pressure from inside the hard, restrictive tube of his chastity device. His heartbeat was pounding in his head as he tried to cope with this sexy, yet cruel vixen before him. As she grinned down on him knowing there was nothing he could do about it, he called out to Heather for help.


"Aunt Heather!" he wailed pitifully, "Susan's teasing me!"

Heather was just coming up out of the pool on the swim ladder and she looked at Timmy with skeptical resignation.



"Looks like it's naptime for our little baby," she said with a sigh.

"B-but it's not even 2 o'clock yet," he whined miserably.
"Come along, baby," she said as she took his hand, "The party's over for you."
Pouting in helpless sissy frustration, Timmy stamped his Mary Jane clad feet as Heather led him into the house and straight to his nursery. He hated taking naps, not just because it was babies that needed them but because he found he was having and harder time keeping his crib dry by the time Heather came in to get him up. And now he was forced to go an hour early. How was he going to manage?

Heather stopped by the kitchen only long enough to grab his 32 ounce baby bottle that was already filled with formula.

"Here you go sissykins," she said as she tucked the fussy, fidgeting boy into his crib, "Make sure you finish it all up before I come in to wake you."
Defeated and completely controlled once again by his babysitter, Timmy regretted, not for the first time, his mom's decision to have him stay at Alice's house.
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ProperPrepSchoolPrincess
I am in love with these stories
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bubblebutt
with women like those around all the time im suprised he has exploded yet, but i lvoe your stories
plump and soft
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