When a sister is in charge
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Josh resented the hell out of his haughty, imperious sister, Kelly.

Even though she was a year and a half younger than he was, she still pushed him around and told him what to do all the time. And because of Josh's effeminate and weak personality, his mom had given Kelly the right to discipline Josh whenever she was away at work.

Consequently, Kelly lorded her authority over Josh with a heavy hand, making him hand wash her lingerie and do all the chores around the house, even those that had been specifically assigned to her by their mom. And if that weren't bad enough, she insisted he dress in a frilly maid's uniform and heels, just to humiliate the hapless boy.

At the end of the day, Kelly had set aside what she called "inspection time". This was where she went around and checked up on all the jobs she'd given Josh to make sure they were done to her satisfaction. If they weren't, Kelly felt it was her responsibility to see to it that Josh was properly motivated to make sure he'd do better in the future.

Inevitably, this meant no small amount of tears and a very sore bottom.

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cd404
kelly is very sexy, I love the idea. What colour of maids uniform?
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Wannabe_Baby
I love your captions as much as ever, Baby Bobby. They're my favourites on the site.
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Baby Flo
What a goddess! I love this cappie, thanks!
Love everybody
and
everybody will Love you
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Sissygirl92
Great story
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Mina Silverwind
I love the caption that came with the great picture, this would make a great series of stories, and you are a great contributor.
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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slutboy18
I have no idea how many times I have made my clitty do something bad in my panties when looking at this photo 
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sissy sabrina
A lovely picture and a nice caption.
makes me very excited.
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francescd
Sisters should be in charge of paddling thier sissy brothers when needed.
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Arianna
I want to be spanked by her. Wow to be sissified by a dominant sister. Now he's sooooooo cute!!!!!!
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carrilee
Kellie is a HOTTIE!!! I'll let her work me over any time!!! I would love to have a body proportioned like that!!!!
huggs and kisses
sissy carrilee
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babyem
ill be her maid anytime
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ROCK BOTTOM
Kelly can be my sister anytime.
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poohbear
she can spank me
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poohbear
over and over
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karengirl
thanx for sharing this beautiful story
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Baby Bobby__
Josh's mother was increasingly impressed by the way her household was being run in her absence, a fact she attributed to her lovely daughter's methods. As a consequence, Josh's numerous complaints about Kelly's discipline fell on deaf ears.

It was just a short time after that, that Josh had an accident in his bed, and Kelly suggested diapering the boy at nights to protect the mattress and sheets. Convinced of her daughter's wisdom, Josh's mom quickly agreed and together, they all made a shopping trip downtown to pick up supplies. With Kelly's inspired direction, they soon obtained everything they needed; two dozen cloth diapers, a half dozen soaker pads, diaper pins, baby powder, and a sizable collection of plastic panties.

Josh's mom had initially picked out the plain white pairs but Kelly strongly advised against it.

"I know the pink and nursery print panties will be somewhat embarrassing for him to wear but they will also encourage him to make more of an effort to stop his bed wetting," she told her and her mom was once again impressed with her savvy daughter's thinking.

That night, the two of them put Josh in his first diapers since he'd been potty trained so many years ago. He squirmed and fidgeted but his mom's warning about a sound spanking soon quieted him down. He pouted miserably as the colorful nursery print plastic panties were pulled up over his soft but thick diapers. Kelly smiled down at him in satisfaction as he she ran her long nails around the waistband of his panties, making sure the diaper was all inside.

"There," she said with a smug smile, "that should keep your bed dry."

The next day, after Josh's mom had left for work, Kelly was changing Josh into his usual maid outfit when she decided against dressing him in his usual frilly panties.

"I think a sissy bedwetter should wear diapers during the day as well," she told him firmly.

Josh had finally taken all he could take.

"No!" he shouted in an angry hissy fit, "I won't do it!"

Kelly, who had been sitting down at the time, pulled out her favorite instrument of discipline, the oak Spencer paddle and laid it across her lap.

"Oh, I think you will after I've warmed that little sissy bottom of yours."


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Ami
Wow! Nice update!
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sexxygirl326
I love it! Keep up the good work!
Kisses!
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