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Short stories
#61
please put me in sissy dresses im a sissy and should spend my life in girly cothes and wear a bra and spend he rest of my life as a girly
I remain as always

Your Deeply Obedient Ever Worshipful Sissy

Sissy Baby Connie Pickles
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#62
He begged his mother not to put him back into a nappy, but she was determined to go through with his punishment.

"But the girls will see I've got a nappy on, and they'll tease and tease me!" he protested. She assured him that once he had his shorts on no-one would be any the wiser. He still wasn't convinced, and it was only the threat of another spanking and being made to wear a skirt rather than his shorts that ensured his meek compliance.

But when she put the nappy on him, and his plastic baby knickers, she made sure to pull them up as high as they would go, and fastened his shorts so that both his nappy and his baby knickers were an inch or so above the waistband of his shorts. The t-shirt she chose for him was short, so although he didn't yet realise it, as soon as he started playing, or bent over, or lifted his arms, the girls would get a good view of his his babyish underwear.

   
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#63
Trying to hide a nappy under denim is never going to work, TBF. Honestly, if you’re being put back in nappies, the best thing to be wearing is the prissy dress pictured earlier (which is exactly the sort of outfit that would have accompanied my own nappy punishments).
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#64
(10-04-2020, 04:24 PM)Girlygirl Wrote: Trying to hide a nappy under denim is never going to work, TBF. Honestly, if you’re being put back in nappies, the best thing to be wearing is the prissy dress pictured earlier (which is exactly the sort of outfit that would have accompanied my own nappy punishments).

Very true
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#65
1

How did it end like this?

5 years ago he met Jane at the disco.

Love at first sight, she melted into his arms.

Married, blissfully happy.

Then Jane changed. She became bossy, assertive, dominant.

At first he was happy, playfully submitting. The sex was great.

Then everything changed.

His cock begged to be released from its prison.

Uncomfortable latex maid uniform, dangerously high heels.

Knees hurt from crawling on floor.

He picked up the brush and started his scrubbing.

Did not want to feel the cane again.

Did not want to feel the force of Jane's tongue again.

2

Pathetic.

What did see ever see in him?

Never loved him, she was a good actress.

She had now got what she wanted, a pathetic male maid.

All she had to do was keep giving him hope that she would unlock his cage.

She had thrown away the key years ago.

The key hanging on the chain round her neck was something she had found in a drawer.

Still the stupid mutt thought it would unlock his cage.

She had no intention of telling him anything different.

Why ruin things?

3

He smiled at the pathetic man in front of him.

Dressed in a frilly maid dress, pink panties, stocking tops on show.

Stupid mutt actually curtised to him and called him Sir.

Jane dismissed the pathetic disgrace of a man wearing the maids dress from the bedroom.

He was pleased to see the back of him as now he could f♡♡♡ Jane to his hearts content.

In the morning the stupid mutt would serve breakfast in bed and remove the used condoms.


4

Was everybody happy with this arrangement?

Jane got a proper man to service her and a maid at her beck and call.

Her lover got free no strings sex. 

He got to wear a maids dress and be permanently humiliated.

You can decide if everyone was happy with the arrangement.
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#66
Having been caught peeking at the lingerie section of the catalogue yet again, Auntie came up with the perfect punishment. The short dress and tutu style petticoats ensured his frilly knickers were on show at all times. "As you're so keen on seeing every one else's underwear it's only fair that we can all see yours". It also had the added bonus of saving her the trouble of having to lift his dress out of the way for his daily spanking and his burning cheeks (both sets) were always on display
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#67
Pineapple and Satin Jessie, I enjoyed reading both your short stories today.
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#68
(12-05-2020, 01:52 PM)Satin Jessie Wrote: Having been caught peeking at the lingerie section of the catalogue yet again, Auntie came up with the perfect punishment. The short dress and tutu style petticoats ensured his frilly knickers were on show at all times. "As you're so keen on seeing every one else's underwear it's only fair that we can all see yours". It also had the added bonus of saving her the trouble of having to lift his dress out of the way for his daily spanking and his burning cheeks (both sets) were always on display
Not only was it I am sure to the great amusement of his associates, but he no doubt learned a great deal from the experience himself. He will one day thank his Auntie from what I am sure will have been but one of many similar experiences.
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