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Cindy was frustrated.

She was frustrated because she was a successful executive at a big downtown firm and had high expectations for those around her.

And she was frustrated because she'd married a man who, to her disappointment, had turned out to be nothing but a premature ejaculator. He'd proven totally incapable of satisfying her sexual needs and Cindy had many needs to be satisfied. And despite all of Dave's bravado and claims of manliness, he'd turned out to be anything but manly. In fact, she found him to be rather sissyish, and her suspicions were proven correct when she found him one day masturbating in her panties. However, as she was to find out later, that was just the tip of the iceberg. Quite by accident, Cindy stumbled upon Dave's secret stash of diapers and baby clothes which left her shocked and not just a little angry. Worse yet, Cindy found cum stains in the diapers, which revealed clearly where Dave had been devoting his sexual energies. She kept her discovery to herself as she considered what she should do about it until one day, when she came home one day to find him, dressed in diapers and a frilly yellow little girl's dress.



That did it for Cindy.

Yanking his diapers down, she jerked him across her lap and proceeded to blister his bare bottom with her hairbrush for all she was worth. Dave kicked and cried but she didn't stop until his buns were a blazing cherry red and her husband's face was wet with tears. Sobbing and blubbering, Dave admitted he was worthless as a man and wanted nothing more than to be a treated like a diaper-dependent baby girl.

While Cindy was considering what to do with her pathetic husband, she decided in the interim that he needed a chastity device to put an end to his masturbatory misadventures. Before the end of the week, Dave was wearing his newest accessory which, to his growing frustration, would be his constant and implacable companion.

Still, while Cindy's timely solution put an end to Dave's mischief, it did nothing to solve her increasing need for a real man.

Tim in Accounting had made his intentions quite clear and Cindy realized that Dave was a serious roadblock on her path to ultimate happiness.

That was when her good friend Victoria offered her a opportunity she couldn't refuse. Raising a baby of her own, Victoria told her it would be no trouble to raise another. After all, washing two sets of diapers was hardly more work than washing one.



And as an added bonus, Victoria was still lactating quite generously from her ample bosom, a fact she'd make sure Dave came to appreciate firsthand.

The next day, Cindy brought Dave, along with his supply of baby clothes and diapers, over to his new home where he met Victoria for the first time. His initial delight was dampened not only by his recent wetting, but also by the fact that his new "mommy" felt it prudent to start things off on the right foot by giving him a good hard spanking, just so he'd know who was in charge.

Closing the door behind her, Cindy smiled to herself as she heard the hard slaps of Victoria's paddle rain down upon her former husband's fanny as he bawled like a baby.

She knew for sure her hubby was in good hands now.
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Wannabe_Baby
Aw, absolutely fantastic cappies/short story, Baby Bobby. It's so great that you finally have your own gallery. Your captions are my favourite on the site and I can't get enough of them. They're perfect.
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DanniLace
Wow Fantastic
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slutboy18
I would love to be him
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Mina Silverwind
I love all of these wonderful captioned pictures, the last one is my favorite, and I would love to have Victoria as my mommy.
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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sissytiana
so sexxi ;)
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sissycuddle
I would love to be in Dave's position. Or would I? I love the picture with the yellow dress. Maybe someday. Keep up the good work.
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lonelymommyliz
maybe try to make them more short and to the point but good otherwise
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Lexi
very nice!
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ROCK BOTTOM
Great story and pics too.
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sissy-toddler-jen
that wassimply fantastic! Love the idea of just walking away leaving him trapped like that for ever
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Baby Bobby__


Β that wassimply fantastic! Love the idea of just walking away leaving him trapped like that for ever Β 




Hee hee! Me too!Β 
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marcorpsdoc
Change is good.
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red
I have to write stuff to get to a hundred comments
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sissk101
Sounds like how I was introduced to my neighbors, the lesian twins.
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therunning21
very yummy indeed, good show
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PissyPrincess
You think that you could continue this story? Like, maybe Victoria could place Dave in Cindy's Firm's Daycare?

Or maybe Continuously babifying Dave?
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TiresiasRex
"Cheating" on someone like Cindy with his diapers? Yeesh. This man does have problems.

Stilll....to have to choose between his wife and Victoria - damn, tough one. And I believe we've seen this incredible red head in another one of Baby Bobby's short stories...was her name Megan? In a black and white striped bikini? mmmm-mmmm.
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c2bear
Great job on the story and pics that work well with each other I hope you will continue with the story.Β 
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TiresiasRex
Whoops. My mistake...I confused Victoria above (a strawberry blonde) with the beautiful Heather in "Denna's Return To Babyhood."
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Baby Bobby__
Understandable. Both are hot women, very well endowed, and emminently suited for being nannies for sissy boys. ;o)
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PissyPrincess
So will there be a possible follow-up to this story? Just please no strap-ons, although it is your story!
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sissybaby92
Loved it. Very well done. I'd love to be this good at captioning. Maybe one day...
Once a sissy, always a sissy.
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sexxygirl326
Excellent job on the story and cappies!!
Kisses!
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