Denna's return to babyhood
A frustrated mom finds the best way to deal with her sissy son is to return him to babyhood
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Denna had always been a bedwetter for as long as he could remember.

His mom, who knew all too well about his sissyish tendencies, decided that triple thick cloth diapers and plastic baby pants at night were the correct answer. Between that solution and a crinkly vinyl mattress cover, she finally managed to successfully keep his bedding dry. He was embarrassed having to wear the humiliating diapers but his mom had her mind made up.
They had a routine every night when Denna would report to his bedroom at 7 00.

But as time went on, Denna fell into the dismaying habit of wetting his pants during the day as well and his mom was forced to re-evaluate his situation. She decided on training pants initially and she ordered a batch of various cute designs from Ebay.



Denna managed to soak right through these so after a sound spanking, his mom began putting noisy plastic panties over the training pants, hoping the added humiliation would encourage Denna to try harder.
Her efforts notwithstanding, he would arrive home after school, with wet spots on the seat of his pants where his pee had soaked through the thin layered training pants. With a heavy sigh, Denna's mom realized more serious measures were needed and only a thick, thirsty pair of diapers would be enough to keep his pants dry throughout the day.

But Denna was having still other problems at school. The stress of trying to live up to being a boy was apparently too much for the youth and he tended to cry over the slightest provocation. After being picked on by the other boys and teased about being a sissy, his mom considered pulling him out of school. She was at her wit's end and unsure of what to do with her prissy son when she hit upon an idea.
As it turned out, her good friend happened to be a tutor and one day, over some drinks around their swimming pool, she agreed to teach Denna at home for a fraction of her normal fee.

When Denna came home that afternoon, his diapers soaked as usual, his mom brought him into their kitchen to meet his new tutor.



Denna blushed with shyness at his new teacher. He had always had difficulty holding eye contact with attractive women and this stunning stranger was certainly no exception.

"Hello Denna, my name is Heather," she said in a voice reserved for toddlers, "I'm sure you and I are going to be the best of friends," she greeted him warmly, "And I'll bet you're anxious to get out of those wet diapers and into some dry ones, hmm?"

Denna's face burned hotly with embarrassment. Up until now, nobody knew about his shameful habit except his mom and his anger at her was exceeded only by the crushing shame he felt as Heather looked down at his bulging hips and smiled knowingly. It was only with great effort that he fought back the tears blurring his vision.

"Aww, don't cry little Denna," she said as she leaned forward, giving him an excellent view of her fabulous cleavage, "maybe you can show me where your mommy keeps your diapering supplies?"



"What a wonderful idea!" his mom gushed, much to Denna's chagrin, "And what a great way for you two to get a chance to know each other better."

With his cheeks blazing with shame, Denna reluctantly led Heather back to his room with her close behind him. He'd totally forgotten that he'd left his pink teddy bear on his bed and as they entered his room, he momentarily panicked. Doing his best to shield it with his body, he quickly threw it on the far side of the bed but it was too late.

"What a lovely teddy bear!" she remarked eagerly, "Why don't you hold that for comfort while I'm changing your pampers?"

Poor Denna was far too weak-willed to say anything to oppose her so he held his teddy in his arms as she gently laid him down on the bed and began taking his pants off.

"You can call me Ms. Heather, from now on, Denna," she said as she pulled his pants down and exposed his bulging, wet diapers, "And from now on, I'll be your teacher and nanny and there's going to be a few other changes around here as well."

As she reached down to peel his clinging plastic panties off his diapers, Denna could hardly return the look her in the pretty eyes.



"Now that you're out of school, and away from all those teasing boys, there's no need for you to wear all these extra clothes. You and I are going to go shopping and we'll pick out some cute diaper shirts and tops that will make changing you easier. Won't that be fun?"

Denna gasped with humiliation at the future she was painting for him but again, he was too much of a coward to say anything to stop her.

"I'm also a big believer in spankings so I expect you to do as you're told, without question--Do I make myself clear?" she asked, her tone serious now.

"Ye-yes, Ma'am," he squeaked weakly as he clutched his teddy bear to his chest tighter.

Quickly and efficiently, she cleaned up his damp bottom and groin before taking a fresh stack of diapers and positioning them under his rump.

"We'll start today on your new warddrobe. It just so happens I know of a store across town called Babies And More that will have all sorts of cute outfits in your size. You've made it clear to your mommy that you want to be more of a baby so I'm going to make sure you get what you've been asking for."

Denna started to protest, his mouth trembling as he struggled to think of a way to prevent what was happening to him.

Taking a big pink rubber pacifier out of her purse, Heather plopped it into Denna's gaping mouth and beeped him on the nose playfully.

"And now let's get you diapered and ready to go--we want to be sure to beat the crowds downtown," she told him as she began pulling his plastic panties up his legs.

What had his mom gotten him into? Was this the end of Denna's attempt to reach maturity?
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Mina Silverwind
The story is well executed, the pictures made it very impreessive, and i hope you have continued success all you post.
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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sissy-toddler-jen
that was lovly thank you so much
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bubblebutt
awesome new story
plump and soft
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clarisselovelace
Very good story indeed. I would do anything she asked me to do.
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BabyMandi
I loved this, i hope to see more like this from you in the future.
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babyjessie
please please please tell me there is more!
Lots of tight and long hugs!
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Baby Bobby__
After pulling up Denna's plastic panties, Heather sat back and took a closer look at her new charge but she couldn't help stifling a giggle.




"You really do look like a baby, you know that? But at the same time, these diapers look so natural on you, I can't imagine you being without them."
Denna squirmed uncomfortably, his mouth still filled with the big pink rubber pacifier Heather had stuffed into it. Quickly and efficiently, she put away his diapering supplies and then folded his jeans neatly, putting them away in his dresser.

"B-but...aren't I going to wear those?" he quaked nervously.
"No, I think you'll be just fine without them. The only pants you need are your plastic pants," she giggled as she patted the thick front of his diapers with her manicured hand.
"Bu-b-but--" he whined.
Taking his pacifier, Heather pushed it back between his lips and smiled down at him. To further emphasize her point, she took a strawberry and put it in her own mouth, to illustrate what she wanted him to do.



"That's it Baby," she said with that coy smile of hers, "suck on your paci like a good baby."
Denna was devastated to think of going out the front door in just his diapers and a shirt but he couldn't think of any way out of his predicament. And he certainly didn't have the backbone to stand up to his intimidating, pretty new babysitter.

Before he could give it a further thought, Heather grabbed her car keys and took Denna's hand, leading him out to her car. Denna squirmed and blushed as the harsh light of sunshine shone down on his new, babyish look. His cheeks were burning hotly as he scurried around to the front seat, only to find it locked.

"No Sissy," Heather shook her head, "Babies have to sit in back."
She finally unlocked it and Denna jumped inside trying to hide his shameful appearance.

They drove across town and before long, were pulling into the parking lot of Babies and More where Heather's friend Jennifer was just heading inside to start her workday. As Heather pulled a trembling Denna out of the car, she introduced him to Jennifer.

"This little sissy stills wets his diapers and we'd like to get some age-appropriate clothes for him," she told her friend.
Jennifer bent over to get a better look at the brightly blushing Denna.



"Hello there, Babykins!" she greeted him cheerfully, "Why don't you come in with me--I know just the right section for us to find some cute outfits for you."
In Denna's panic, he felt a surge of warm pee flooding unannounced into his diapers but he was too embarrassed to say anything about it. Instead, he stared at the ground hoping in vain that it would swallow him up. The ground failed to oblige him however, and Heather and Jennifer took him into the store where the patrons couldn't help but stare at the obviously diapered sissy boy.

Jennifer was very enthusiastic about helping Heather and they found a number of outfits that would be a perfect match for Denna's prissy, weak-willed personality. The first was a darling pink and white gingham baby dress, purposely cut short to make sure Denna's diapers would always be on display;



"Won't this be lovely?" Heather enthused, "Everyone will be able to see your sassy ruffled rumba panties."
Denna blushed hotly as the two women looked down on him, eager for his reaction.
They picked out a few more and then Heather told Jennifer she'd need some outfits just for Denna when he was toddling around the house.
"I need an outfit that he can wear in the crib, playpen, or just when he's in his nursery playing with his dollies," she explained.
"How about this?" Jennifer offered.
It was a short white diaper shirt with pink accents and matching rumba panties.



"That's exactly what I need," she agreed. Together, they found a few more in baby blue and lemon yellow so Denna would have variety.

"Oh, there's just one more thing..." Heather said as she stacked the baby clothes into her cart, "I'm not sure if you can help me but as Denna's babysitter and nanny, I could really use a good wooden paddle for when he throws a sissy tantrum..."

"Not to worry," Jennifer beamed, "I have a nice oval one over here that will make sure your little sissy is on his best behavior." The two of them giggled like school girls as they perused the section of disciplinary aids.

"This one will be just fine, don't you think Sissy?" Heather asked as she held up a slim oval shaped paddle.



Denna squirmed and blushed again as he mumbled something unintelligible beneath his breath.
"But then, I'll bet your little sissy here would probably cry with just a hand spanking--am I right Babykins?" Jennifer asked.
Denna's face was burning with shame as he stood there, captive to these women's humiliating comments.

"Mm-hm," Jennifer smirked, "I can always tell those little boys that cry over the tiniest little things."



As if to confirm her suspicions, Denna found himself fighting back the tears from this onslaught of female degradation.

"Aww, you poor little thing," Heather said as she bent down and put her hand on his shoulder for comfort, "I think he's upset because he wants to wear one of his new outfits home."

....to be continued(?)










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bubblebutt
oh please do countine it loving this story
plump and soft
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babyjessie
no doubt about it, this must be continued. absolutly!!!
Lots of tight and long hugs!
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Prissie
Whoever that girl is, I luv the way she poses for those pictures!

**Prissie jumps up and down and giggles and is all excited   **
   Prissie
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marcorpsdoc
Best education a sissy could ask for
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TiresiasRex
"...to be continued (?)"

Will we ever see the continuing misadventures of Denna again? (And I vote for more appearances from Heather, please).
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yobo
Please more baby bobby! I beg you!
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jessybaby
continue? YESSSSSSSSS
a new me teehee
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BabyBarby
definitly!!!!!!!!!!!
Come Visit my Gallery!!!
I have TONS of cappies that need commenting!!! REALLY GIRLY CAPPIES!!!

::::::: GALLERY :::::::


PM me!! I Photoshopped my head (with make up and wig obviously! onto a sexy girls body in my Avatar, anyone like?? Im still disquised a little hehe xx
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Jennifer Funshine
Really love this babyhood tale, Baby Bobby plus the pictures are outstanding!
I particularly adore the two outfits and Jennifer's playful demeanor is quite welcoming.
Seeing as how you have such a dedicated audience (myself included)
I do hope you continue with this cute story... Pretty pweese! :)
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Baby Bobby__


 Really love this babyhood tale, Baby Bobby plus the pictures are outstanding!
I particularly adore the two outfits and Jennifer's playful demeanor is quite welcoming.
Seeing as how you have such a dedicated audience (myself included)
I do hope you continue with this cute story, Baby Bobby... Pretty pweese! :)  




LOL, I'll see what I can come up with. ;o)

Btw, the second outfit pictured is actually one of mine that I wear to bed. 
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LilGreg
please, please!!!! OMG!!!!!! this series rocks!!!

The only thing better if he would get off on it!!!
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lucysmith
i love the mix of pics and story.. thank you :)
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Baby Bobby__
On Easter morning, Denna woke up to bright, warm sunlight streaming through the frilly curtains and into his bedroom. Slipping out of bed, he sighed and stretched, feeling the clammy embrace of his soaking wet diapers beneath his pink plastic panties. He rubbed the sheet over his mattress and was thankful for the crinkly vinyl covering that protected it.
His mommy came in shortly after and she looked down on her bedwetting sissy son to see for herself that once again, he'd had another predictably wet night.



She went about her normal business of changing him, pinning a fresh set of thick diapers on him, followed by a lace lined pair of yellow nursery print plastic baby panties.
"I think today it would be wonderful to try that precious yellow dress that Heather got for you," she told him as she pulled his pantioes up for him.
Denna blushed at the memory of it. As his mommy brought it out of the closet for him to see, his eyes caught the humiliating inscription across the bodice;



It was mortifying to have to wear such an outfit, all the more because it advertised his childish incontinence to anyone who could read. Nevertheless, Denna didn't argue as she slipped it over his head and secured the small, impossible to reach buttons in back. Once again, he would be helpless to remove it without someone else's help. And as usual, the choice had been made for him, by someone else, and Denna was too weak-willed to protest.

After breakfast, Denna's mommy led him out to the back yard to put him into his playpen where he could play with his toys in the sunshine.
Denna quietly amused himself for a half hour until he heard the sounds of another woman's voice along with his mommy's coming closer. Stepping through the back sliding glass door, his tutor and nanny Heather walked out, carrying a basket of colorful Easter eggs.
She looked down at the blushing Denna and smiled at the emasulated sissy wearing his dress and diapers.



"How's my favorite little sissy?" she greeted him enthusiastically.
Denna was so bashful he could hardly keep eye contact with his pretty mentor and he fidgeted as he looked down at the shiny white vinyl of his playpen, with its cheerful and happy nursery characters. When he did look back up, his gaze fell upon the yawning cleavage of Heather's low cut top and he gulped reflexively, even as he tried to tear his eyes away from it.

"Hi, Ms. Heather," he squeaked.
"We're going to have all kinds of fun today, Denna," she told him breezily, "and I know you'll be just delighted to know that my friend from the store, Jennifer, will be stopping by later."
Denna cringed at the thought of the two of them seeing him in his current outfit that told everyone about his nightly bedwetting.
"And look what else I brought you--I have a specail surprise for my little sissy today."

Denna's cheeks turned even redder as he beheld the pink pacifier she was holding for him with great eagerness.



Popping it into his mouth, Denna whimpered weakly as he held onto the padded sides of his playpen, his mommy and Heather smiling down at the now pacified sissy.
"Oh yes--that definately suits you," Heather said.



"C'mon sissikins, let's play on the swing set," she said as she helped him step gingerly out and over the side of his babyish prison. She led him over to the swing set and after getting him seated, started to push him forward to get him going.

At first, Denna was having great fun initially, although his short baby dress was starting to blow up alarmingly as the wind caught it and it exposed his bulging, embarrassing diapers to the neighbors watching him from next door.

His cries of excitement began to take on a concerned tone as he struggled in futility to keep his balance and hold the frilly hem of his dress down to cover his colorful plastic panties.
Behind him, Heather waited for him to swing back in the seat before she launched him even higher into the air with each push. Denna squealed with fear as he soared higher and higher--this was too much for him!
"St-stooopppp!!!" he wailed in his high pitched, frightened voice, "I'm scared! Mommy!!!"

Before long, the inevitable happened. As poor Denna held onto the swing chains for dear life, he felt the front of his diapers growing wet and warm, as fear-induced pee quickly saturated the front and seeped its way into the thick seat. As Heather stopped pushing his swing, tears of shame tumbled down his reddened cheeks as he felt his bottom squish miserably against the sopping wet cloth within his plastic baby panties.
"Aww, poor little sissy," Heather said as she came around the front of the swing to console him, "I know that look. Did sissy have another accident that he needs to tell me about?"

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TiresiasRex
You continued it! YES! A dream come (cum?) true for me. Thank you, thank you, THANK YOU, Baby Bobby for listening to our requests!

(And as an aside: I have been following the thread re: one of your posts being taken down...and yes, sometimes the "vulgarity" censorship does seem a bit...irregular. Especially as many of your previous threads - which I am fine with, by the way - contain more, ahem, hardcore images. As for THIS story, however, it is possibly as "innocent" as a fabulous sissybaby story can be...).

P.S. My only critique: I preferred Heather as a redhead...but beggars can't be choosers, can they?
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babyjessie
Holy! I came back from a week away and I love what i see! Please don't stop this one :)
Lots of tight and long hugs!
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staceyrockz
What an amazing set of cappies. The fashionista in me must know where you found the panties in the first post with the I Dream Of Gina print?
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Gayby!
All your cappies always make me wet myself! hehe 
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jessybaby
uh oh, whats next for baby?
a new me teehee
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