A Painful Adjustment

[Baby Bobby__]

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.

http://pixprincess.com/cg/albums/userpics/10646/12.jpg

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.

http://pixprincess.com/cg/albums/userpics/10646/paddle.jpg

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.

http://pixprincess.com/cg/albums/userpics/10646/baby_dress.jpg

Alice's friend Heather, thought he was just the cutest little thing and she often told him what a pretty little sissy he was.

http://pixprincess.com/cg/albums/userpics/10646/Denise180.jpg

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.

http://pixprincess.com/cg/albums/userpics/10646/Baby_girl2.jpg

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.

http://pixprincess.com/cg/albums/userpics/10646/Denise284.jpg

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.

http://pixprincess.com/cg/albums/userpics/10646/Alice10.jpg

"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(?)

[clarisselovelace]

Man. Sissy is going to have to change her name to blue balls.

[bubblebutt]

please pelase do countine

[Mellsissy]

Ouch that would stink. But a great story.

[francescd]

Wonderful story, sweety.:)

[diapered_tristan]

great story cant wait for more:LollyPinkKiss:

[c2bear]

Great story so far and good choice on the images. Hope you will continue the story:girl1:

[babie]

ou loves that paddle hope i am next

[Mina Silverwind]

I love all of these, the story behind them is excellent, and thanks for sharing all of your fantastic work with us.

[DiaperDreams]

oh i wish i was him

[Katie_Babygirl23]

very nice I can't wait for more

[Daddy Bradley]

Nice story. Alice and Heather are true beauties. Please continue.

[marcorpsdoc]

Contiunance?

[babyjessie]

Yea, Will you continue?

[BabyDiana]

This was really good. Please Continue!

[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.

http://www.pixprincess.com/cg/albums/userpics/10646/Dress_panties.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/04Denise.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/Denise332X.jpg

"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...

[babyjessie]

I agree! It's a great addition, but please dont just leave it at that! I can't take it anymore!!!

[bubblebutt]

she is evil but know one would ever know

[red]

That's a big momma

[straightsissy13]

Isn't that everyone's secret dream haha :)

[Flyff]

Wow, I haven't read a story this good since sissybekcy's site was taken down. Nice.

[koharu]

please post maor

[Puppy Amber]

Please, please write more!!!

[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."

http://www.pixprincess.com/cg/albums/userpics/10646/Denise361.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/diaper_girl10.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/Penny8X.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/Jordan94.jpg

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."

http://www.pixprincess.com/cg/albums/userpics/10646/Jordan96.jpg

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.

http://www.pixprincess.com/cg/albums/userpics/10646/polkadots25.jpg

"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.

[ProperPrepSchoolPrincess]

I am in love with these stories

[bubblebutt]

with women like those around all the time im suprised he has exploded yet, but i lvoe your stories

[gigglesalot]

i love it. i am sure glad that i am not in a chasity device like that. pure torture. especially with all of those hotties around. post more soon baby bobby

[babytephx]

No cummies :( what a painfull way to live

[Hi00180]

http://pixprincess.com/cg/albums/userpics/10646/Baby_girl2.jpg



Where can I get diapers like that?

[Sissybaby Thuthy]

http://pixprincess.com/cg/albums/userpics/10646/Baby_girl2.jpg



Where can I get diapers like that?

Nice and thick the way I like it!

(You can't get them that thick. You just use 2. or 3 or 4?)

:girl1:

[Baby Bobby__]

Yes, that's the problem with disposables--its hard if not impossible to find a suitably thick pair. That's why I wear nothing but cloth diapers and plastic panties. I like them nice and thick so they're impossible to hide.

[Littlepissy]

very lovely story

[Sissy Desiree]

This is a great story! And I love the pictures! Thanks.

- Sissy Desiree

[Sissy Desiree]

One other thing. You can make a thick diaper by laying a thick, absorbent bath towel on the bed and putting two or three thin, cheap bath towels on top of it. (You can even use pink towels if you like :) After you've powdered your bottom, sit on the middle of the towels and fold the ends over in front and back to get the right length, then pull them up and around your waist and pin them on snugly. You can get kilt pins that look like safety pins; these make nice big baby diaper pins. Then pull on your plastic baby girl panties. This kind of diaper is fine for a long night of heavy wetting. If you want, you can add a few rags between your legs as extra padding to give you more of a babyish waddle as you walk. It's fun to wear this under a pink baby girl pajama suit. You can find one of these at http://www.bigfeetpjs.com/ for example. Now if only I had a real crib to sleep in... :)

- Sissy Desiree

[Icehaze]

I love those plastic panties >.<

[therunning21]

i like them really crinkly, so sometimes i just put on 2 or so

[therunning21]

i really like your story hun

[bedwetter41]

[QUOTE Great post here Baby Bobby. I liked all of it -- but by far the most telling aspect is when the sissy is so horny -- he only thinks about "running to his Nursery and masturbating furiously". Not making love to the girl. Not F-ing her hard (like a man would do) -- but "running off to his Nursery to masturbate (?!?!?)
You see -- this is where his inate sissiness betrays him -- and keeps him under "lock and key" (figuratively and physically) His own weakness -- his own childish self-pleasuring mindset. For this reason alone -- he belongs right where he is. In diapers -- sleeping (Alone!) every night of his life in his Nursery - and locked in chastity. (? BTW Can sissies actually be "chaste"? They aren't ever going to have sex with a girl anyway -- so they are only "chaste" in the sense that they are not "dating" their hand. ?)

[TiresiasRex]

Your most amazing collection of beauties, yet, Baby Bobby! And oh, how I would love to be in nice, thick diapers like our "hero" and surrounded by these women. Ah, to dream....

[Baby Bobby__]

[QUOTE Great post here Baby Bobby. I liked all of it -- but by far the most telling aspect is when the sissy is so horny -- he only thinks about "running to his Nursery and masturbating furiously". Not making love to the girl. Not F-ing her hard (like a man would do) -- but "running off to his Nursery to masturbate (?!?!?)
You see -- this is where his inate sissiness betrays him -- and keeps him under "lock and key" (figuratively and physically) His own weakness -- his own childish self-pleasuring mindset. For this reason alone -- he belongs right where he is. In diapers -- sleeping (Alone!) every night of his life in his Nursery - and locked in chastity. (? BTW Can sissies actually be "chaste"? They aren't ever going to have sex with a girl anyway -- so they are only "chaste" in the sense that they are not "dating" their hand. ?)

Bedwetter41;

Rarely have I seen someone articulate so well, the plight of true sissies as you have, both here and elsewhere in my gallery.

You are exactly right on several levels--these sissies are naturally intimidated by babes that come into their narrow, limited world and they know better than to think that they would have a chance with them (which would be zero, in any event). At best, the very most that they can hope for, is a minute or two of uninterrupted self pleasuring by themselves in their nursery, so they can cum in the safety of their soft, bulky diapers.

But savvy women know this, and take measures to lock up the diminutive wee-wees of their prissy sissies. They reason (quite rightly) that since the sissy can't please a real woman, there's no reason why they should be able to please themselves whenever they want either.

The downside for a sissy in that position is unremitting horniness and frustration. But on the plus side, they are able to indulge in the sissy pleasures of wearing their baby girl outfits and soft, cozy diapers.

So thank you for your cogent, on the mark, observations. ;o)

[tina101]

great story

[diaper2509]

This is truely the starting of a great story. like everyone else I love the pics

[Baby Bobby__]

"Time to wake up, Timmy," Heather sang cheerily as she strode into his nursery.
Looking down on the sissy stirring in his baby crib, she smiled down at him with her natural air of superiority.

http://www.pixprincess.com/cg/albums/userpics/10646/Denise500.jpg

Jimmy sleepily yawned and sat up, swinging his feet over the edge of the crib that Heather had just opened for him. As she slipped his Mary Janes onto his feet, Timmy clutched his teddy bear and sighed heavily. His thick, bulky diapers were soaking wet, once again.

http://www.pixprincess.com/cg/albums/userpics/10646/Dscn0050.jpg

He realized the wetness had even seeped all through his seat and up and around because even the waistband of his nursery print plastic panties were damp.
Timmy couldn't remember the the last time he'd woken up from the urge to pee--anymore, he just slept through it and even when he was awake, it seemed like he could hardly keep his diapers dry for more than an hour. And Aunt Alice had long since told him that training pants were out of the question.

She had even bought him a fuzzy pink diaper shirt--which he was wearing now--that said "Bedwetter in Training", a humiliating announcement of his infantile status.

Heather bent down, revealing her unbelievable cleavage to the frustrated sissy and squeezed the cushiony front of his soft diapers to check on him.
"Just as I thought--wet as usual," she giggled.
"Can you change me please, Aunt Heather?" he asked in his soft, plaintive voice.
"Sorry sissy, its laundry day and we only have one clean change left for you. You'll just have to wear those until beddie-bye time.
"But don't worry, that's only three hours from now," she said with her beautiful smile.

Timmy pouted helplessly.
It was increasingly rare for him to have his diapers dry anymore for any length of time. More often, they were partially wet or completely soaked until his next change.

"This should cheer you up," Heather said brightly as she pulled Timmy's diaper shirt off him, "Your aunt Alice bought you a lovely new pink dress with lots of frills--perfect for a big sissy like you."
Timmy raised his arms as Heather gently helped him into the prissy ensemble. Pulling the hem down, Timmy realized it barely covered the top of his diapers. He lifted the front and looked down with concern at his wet diapers.

http://www.pixprincess.com/cg/albums/userpics/10646/Dscn0061.jpg

"But everyone will see I'm wearing diapers, Aunt Heather," he complained.
"Timmy--everyone knows you wear diapers, that's no secret. You're going to have to get used to that fact because everyone sees you as nothing more than a big baby now. I know you thought you were going to be able to continue living as a little girl but you're just too immature. That's why Alice put you back in diapers."
Timmy pouted in silence, knowing there was nothing he could do to change his situation, he just had to suffer through it as best he could.
Heather popped his pacifier into his mouth and led him into the living room where she could keep an eye on him. With a wet squish, he sat in the middle of the floor and began playing with his dolls.

Later on, as the shadows grew longer inside the house, Heather checked the clock and suddenly exclaimed, "Oh my gosh--its getting late and I still have to get ready for my boyfriend!"
Timmy sucked feverishly on the pink pacifier filling his mouth. He loathed the idea of someone else getting Heather's attention and he was consumed with jealousy.
Oblivious of his feelings, she strode out of the room with her sexy sashay and he sighed in defeat.

About ten minutes later, Heather called out to Timmy in a provocative tone of voice.
"Oh Timmy? Can you come in here and help me with something?
Always eager to serve Heather in any capacity, Timmy waddled down the hall and into the bedroom.
"I'm trying to get ready and I need the last few clasps of my corset closed--can you help me with them please?" she asked in her sweet, musical voice.

http://www.pixprincess.com/cg/albums/userpics/10646/Denise446.jpg

Timmy gasped as he stared at her luscious melons, literally bursting out of the pink top. Instantly, his little penis was struggling within its plastic prison to become hard but it was quickly prevented from doing so by the infernal shortness of the chastity tube. He groaned and shifted his weight even as he rubbed the front of his wet diapers in a futile attempt to alleviate the pain.
Still, he couldn't take his eyes off Heather. His poor penis throbbed desperately as his heartbeat pumped into overdrive.

Panting heavily, Timmy brought his shaking hands up to try and close the last few hooks on Heather's corset.
"That's very sweet of you," she said breezily.
Timmy realized somewhere deep down that she was doing this just to torment him but he didn't have the willpower to walk away from her.
A bead of sweat trickled down his brow as his fingers brushed the soft skin of her beautiful breast. He trembled like a leaf as he tried to concentrate on the task at hand but his wee-wee was being painfully crushed within his chastity tube. It was like sticking one's hand in a vice and then slowly, willingly turning the handle!
"If you like what I'm wearing, I'll keep it on while I feed you your dinner," she whispered temptingly.

Timmy whimpered desperately even as he panted like a dog. How was he going to be able to eat, never mind swallow the baby food she normally spoon fed him when his entire view would be filled with these incredible breasts? What was a sissy to do?

[SissyDesiree]

Wow, even more! Thanks a lot, Baby Bobby -- I love this story!

- Sissy Desiree

[meisababy]

thank you for great story i love it a lot a lot a lot!!!!!!!!!!!!!!!!!!!!!!!!!!

[stellaindiapers]

continue the story and give some background please