PG 13 Tommy's New Underwear
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Tommy came home feeling frustrated, fussy, and cranky.

For the third day in a row, he managed to wet his training pants, despite his monumental efforts to the contrary. Yesterday, it had been because the school bus had been delayed in traffic getting home, and today, it had been a quick brush in with some bullies in the play yard during recess. Their intimidating ways had caused him to wet himself in fear--a not uncommon event in Tommy's life.

In any case, his trainers were now fully soaked and despite the extra protection of the plastic panties his mommy had wisely dressed him in, he nonetheless found them leaking around the edges. And Tommy knew only too well what that would mean. Instead of his obligatory nighttime diapers--his mommy would insist that he wear diapers during the day as well from now on. It was bad enough being called a sissy all the time wherever he went, now there would be no hiding his shameful secret from anyone.

By the time he reached his house, he'd reached a state of full blown pout. His lower lip puffed out as he trudged inside and he found his babysitter Brittany in the bedroom changing some sheets. She was two years older than Tommy, and with her long auburn hair and big breasts, he'd always held a secret crush on her.

"What's the matter, Tommy?" she asked as she took in his forlorn look and sad, puppy-dog face.

"I-I had an accident again," he mumbled dejectedly.

Brittany looked down at him and noticed the wet patches below where his plastic panties ended.

Brittany sighed and crossed her arms over her ample chest.

"You know what this means, don't you?" she asked him pointedly.

Tommy nodded his head but stared down at the floor, unable to look his attractive babysitter in the eyes.

"It means diapers and plastic panties all the time now--day and night time."

Tommy said nothing but sniffed as he fought back the tears that threatened to flow whenever something didn't go his way.

"Come along, Tommy, let's get you out of those wet trainers and into some nice thick diapers," she said as she took him by the hand and led him into his own room down the hall.

Standing in place as Brittany undid his pants and tugged them past his soaking wet underwear, Tommy let out a sob of shame.

"Couldn't I--I mean, couldn't I just try one more time?" he asked plaintively.

"Sorry, Tommy. Your mommy makes the rules around here and she said if you wet your trainers one more time, she'd put you into diapers full time."

Tommy knew the rule as well as anyone did but he stamped his feet in bitter frustration as Brittany pulled his pants off his feet and over his shoes. Taking him over to the changing table his Mommy had thoughtfully provided for the purpose, she sat him down and removed his plastic panties and wet trainers, putting them in his diaper pail which let out a pungent smell of stale pee from two nights worth of wet diapers that hadn't been washed yet.

After cleaning his bald crotch and damp buns, Brittany smeared diaper rash ointment across his bottom and powdered him liberally with baby powder. Tommy cried softly as she pulled a trio of very soft, but thick cloth diapers between his legs and pinned them closed on either side of his hips.

"Don't cry, Tommy," she said as she held a pair of white nursery print plastic panties before him, "See the cute baby pants your mommy bought for you?"

The sight of the waterproof panties only served to remind him just how far removed he was from that of the adult world. It was mortifying having to wear diapers like a baby but ten times as bad having them put on by his pretty babysitter. Now everyone would know just how much of a sissy he was. How could he ever hope to hide the humiliating garment?

Without waiting for a reply from her embarrassed charge, Brittany gathered the leg holes and quickly snaked them up his skinny, hairless legs, working them carefully over the bulky cotton diapers. Consumed with self pity, Tommy sobbed as Brittany followed the elastic waistband around him with her fingers, seeming to hug him as she did it. Tommy breathed deeply of her feminine perfume and wished desperately she would see him as a grown up, instead of a bed wetter and sissy.

When she finished, she sat back and playfully patted the now very thick crotch beneath his shiny plastic panties. His diapers were so thick they forced his legs apart just like a baby's.

"There you are, Tommy--all diapered and ready to go," she said cheerfully.

Despite her glowing smile, it seemed to Tommy that she took great pleasure in humiliating him.

It was all too much for the weak-willed sissy. He broke down and began crying not unlike the baby he now looked like.

Brittany stopped smiling and looked down on him now with concern and sympathy.

"Aww, you poor little thing...come here little Tommy."

She pulled him into her arms and hugged him close, patting the fat seat of his diapers comfortingly.

"Some little boys just can't keep their pants dry," she reasoned with him in a soothing voice as she stroked the back of his head, "But don't worry--you'll get used to your diapers and plastic panties."

That didn't seem to make him feel any better so Brittany decided on a different tact.

"I know what would make my little boy feel better..."

Sitting him up on a chair, Brittany suddenly pulled her top up to reveal her spectacular, round boobs that were filling out her smooth beige bra.

"Do you like what you see, Tommy?" she asked with a smile.

Tommy sniffed and nodded his head, a smile starting to tentatively grow across his tear-stained face.

"Take a good look because this is the last time I'm going to show you...I know you've never been with a girl and probably won't be with one anytime soon--if ever. Take a look and remember these, the next time you're playing with your little wee-wee."

With a playful giggle, Brittany leaned forward and pulled his head between her big boobs and mashed his face there, making the embarrassed sissy squeal with shock and surprise. Letting him go, she pulled her top back down and as she leaned over, she kissed him fully on the lips. Tommy squealed again--he had never been kissed by a girl before! His little pecker had grown rock hard within his soft diapers and he was panting hard as looked up at Brittany's smiling face.

It only took a brief and gentle rub on the cushiony front of his baby soft diapers to bring him to an earth-shattering orgasm.

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19 posts
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Yummy! Love it
*Giggles* Great as always Bobby. :)
I'm so jealous of Tommy right now!
That was awsome! Where do you find such amazing girls?
Lots of tight and long hugs!
Baby Bobby__

Β That was awsome! Where do you find such amazing girls? Β 

Lol, both had a little help from my photoshop. But I normally look for pics that seem to fit the scene of a story, particularly the facial expressions.
i love the story!!!
a new me teehee
loved the story and how she made him wear diapers.
Poor Tommy, I have a soft spot for kids with potty problems. I'm not sure I'd take the babysitters approach to comforting but still a very cute story.
love your story and the pics that go with it thanks
This was great!!!
Lots of humiliation yet such a nice babysitter!
~~~Love*Hope*Compassion*Will~~~These are the things that make up this little heart of mine.
I'm a big fan of these illustrated stories. You always find lovely pictures, and I always have fun imagining myself in the place of the diapered sissy in the story.
- Sissy Desiree

Ah...pain (the humiliation) and pleasure (the breast exposure and the orgasm)....I love how you always bring these two extremes together in your stories, Baby Bobby. And I agree with Clarisselovelace above: as of this moment, I am jealous of Tommy. Diapered and rubbed to an orgasm...mmmmm-mmmm.
Big bad wolf to that girl: "What nice boobs you have!"

Girl: "The better to shove them into your face and put you in your place. Now, take those silly BOYS underwear off and put on these frilly pink ruffled panties ..... "

Hope y'all don't mind,

Great captions the story was a good read nice job.
What an excellent and exciting story. Thank you for sharing although it's not my special day and am trying not to do the same as Tommy in this story.
great gal nice pics
inocent little miss sarah-jayne
Love the stories involving the sissy's crush... It's simple great!
Fabulous :)
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