Sarah teaches Kay a lesson

PG 13 Sarah teaches Kay a lesson

sarahsissyboots

My turn with the crop as Headmistress Bossyboots turns a very bratty schoolgirl into a simpering sissy baby girl.

Posted on September 23rd, 2018 ~ 4:52 pm

Posted in

Photogenic Beauties

Add A New Image To This Gallery

Sarah teaches Kay a lesson - My turn with the crop as Headmistress Bossyboots turns a very bratty schoolgirl into a simpering sissy baby girl., nappies sissified mistress petticoat punishment, Diaper Lovers,Feminization,Dominating Mistress Or Master,Spankings

Click any of the images to see their full size

Headmistress Bossyboots after confiscating Kay's school uniform from the naughty little pansy and replacing with babywear and a very sore bottom! The poor sissy can only suck on her dummy and cradle her teddybear as Bossyboots decides what punishment to next bestow.

Gallery Images by sarahsissyboots

Display More Images

Last Post

8,416 views

26 posts

::Would you like to advertise at Sissy Kiss? Click here for details!::

These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!

Add your message here..

Pink Balloon

Posted September 23rd, 2018 ~ 7:18 pm

Suppose it's the only way Kay will learn.

Just make suee it's a good punishment. *giggle*

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:07 pm

@ Pink Balloon

Oh have no fear sweetie the punishment definitely fitted the crime and I'd like to think Kay will learn though I have my doubts as her attitude remains very poor and a vast improvement is required if she is to progress from nappies to panties again let alone big girl panties.

Quote

◆

Pink Balloon

Posted September 30th, 2018 ~ 7:11 pm

@ sarahsissyboots

I suppose only time will tell.

Quote

Baby Puss

Posted September 23rd, 2018 ~ 8:08 pm

Oh my, what goings on. I know teddy must be enjoying all of this, I can almost see a smile there. Such a cute, but maybe somewhat deflated, sissy baby Kay. I luvs the pink satin outfit. Oh, I like the purple ankle cuffs too. They look a bit shiny, are they leather? Well, enjoy Kay! Actually, both of you should should be enjoying, and teddy too. 😉

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:12 pm

@ Baby Puss

Thank you I'm glad you enjoyed the outfit and the pink dress was specifically selected to humiliate my poor little sissy (though only what she deserves especially after she had the temerity to answer back during a lecture). I shall order Kay to answer your query about the cuffs and she can describe how the cuffs were used as part of her punishment, whether she likes it or not.

Quote

◆

kay3070

Posted September 30th, 2018 ~ 1:31 pm

@ Baby Puss

Mistress most definitely makes sure there is no escape for me whilst I'm being punished Baby Puss. The cuffs and collar go on even before I've been put into baby girls clothes and remain in place from then onwards. Mistress says they are very necessary for such a little brat as I am locked down every time she punishes my bottom - be that over the spanking stool or hanging from chains attached to the hooks in the ceiling. Of course, between these and many other methods of discipline then I am lead around on a chain leash attached to my collar - but always made to walk with my dress lifted up to show my nappies and plastic panties - especially when out in the garden.

All of our cuffs are leather sweetie - they need to be as they are certainly well used. Plus the fact that it all adds to the true feeling of bondage. Same with the fastenings - we both always use padlocks, no doggy clips - you're not in bondage if you can get yourself out of it! (lol). xxxx

MU-WAH!!! luv and hugs from Kay Kandyfloss xxx

Quote

◆

Baby Puss

Posted September 30th, 2018 ~ 3:32 pm

@ sarahsissyboots

Thank you too Sarahsissyboots, I see very well the situation. And, it very well needs to be done in such a controlled fashion. Kay did as you instructed, and explained the cuffs were indeed leather, and how they are implemented. Thank you, for instructing Kay to do so.
My interest in the cuffs, was because I liked the color (no other reason, honest! LOL.) I had thought, they would have been leather. But was not 100% sure, they were not pleather, or other vinyl material.
I have made a set of reins myself, from a leather like material called, biothane. It really couldn’t be mistaken for leather, but it’s strong, and I like it nonetheless.

Quote

lil sissie

Posted September 23rd, 2018 ~ 11:19 pm

Way to go BossySarah mes sees you Put Kay back where She belongs in nappies

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:14 pm

@ lil sissie

Thank you kindly dear although nappies dp not appear to be improving her obedience so I may just need to keep the little pansy babified for the foreseeable future.

Quote

chrissiesissy

Posted September 24th, 2018 ~ 12:02 pm

Luvs your pink knickers, I's sure they ended up round your ankles for a good spankies 'giggles' ♥

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:22 pm

@ chrissiesissy

The pink baby panties are so cute aren't they (all part of the punishment) I think by this stage I'd already blistered Kay's bottom until it was the same colour as her nail polish (giggles).

Quote

deedeesissy

Posted September 24th, 2018 ~ 5:03 pm

Teehee, that's it, Mistress Bossyboots, put the pansy back in nappies after a good spanking, although we all know she luvs it really, and is getting off in that nappy unless you put a stop to it, by restraining those naughty sissy handies!

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:28 pm

@ deedeesissy

Thank you dee she does try to be a big girl but we cant be having that can we (winks) I think the little pansy would be rubbing the front of her nappy and plastic panties if I left her unattended but no fear we have plenty of restraints, chains and locks to ensure no naughtiness and she can pout and stamp her feet all she wants - that's when her plug and punishment gag gets fitted before a trip over Bossyboots knee (giggles).

Quote

Baby Butch

Posted September 25th, 2018 ~ 12:37 am

Bossy Boots is a good character. Kay is not old enough to be a schoolgirl and you did the right thing!

http://sissykiss.com/gallery/baby-butchs-gallery/

http://sissykiss.com/Baby-Butch/blog/awards-blog/

*Hugs Baby Butch*

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:33 pm

@ Baby Butch

Thank you Baby Butch that's very kind and yes Kay does have ideas above her station which had to be swiftly nipped in the bud. Bossyboots is still not satisfied with her attitude so there will be more punishment assignments for my darling little pansy to come.

Quote

sissybabysamantha2

Posted September 26th, 2018 ~ 9:32 am

Well well Kay you have been a naughty girl again i bet you where chasing the boys. So Bossy Boots is right to put you back in nappies where you belong Keep up the good work Sarah. I do love that dress

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:42 pm

@ sissybabysamantha2

Thank you Samantha I can tell you there was a long list of transgressions (attitude, non-regulation panties and bringing dildos to class to name just a few) clearly this could not be tolerated so nappies and baby dresses (not to mention a very sore bottom!) was the least the little pansy deserved).

Quote

kay3070

Posted September 26th, 2018 ~ 2:27 pm

Oh please Headmistress Bossyboots, don't humiliate any further. When you confiscated my school uniform and made me wear a proper little baby girls smocked pink satin dress and frilly bonnet I was so embarrassed. Then when the collar and cuffs went on I knew I was going to have a very sore bottom but didn't imagine that you'd stretch my little sissy hole too - I felt like such a naughty girl when you finally put me into a big bulky nappy and plastic panties with those very frilly panties over the top. To make matters worse you forced me to stand there sucking on my dummy with my pretty dress lifted up to show off my baby panties whilst you took pictures of me - but I didn't know you was going to share them online! Now everybody can see what a naughty little sissy baby I am. I said I was sorry Miss - please don't tell them that I'd shamefully spurted in my nappy like a little pansy - I'll be a good girl ... honest.
xxxxxxxxxx

MU-WAH!!! luv and hugs from Kay Kandyfloss xxx

Quote

◆

Pink Balloon

Posted September 26th, 2018 ~ 10:11 pm

@ kay3070

What's fun about being a good girl?

Just have fun, and if it gets you in trouble, weeelll. *giggle*

Quote

◆

kay3070

Posted September 29th, 2018 ~ 12:47 pm

@ Pink Balloon

Oh no worries there - my promises to be a good girl usually wear off around the same time that my bottom stops throbbing - way too much fun being naughty (giggles).
Don't tell Mistress Bossyboots tho or we'll both end up in trouble!
xxxx

MU-WAH!!! luv and hugs from Kay Kandyfloss xxx

Quote

◆

Pink Balloon

Posted September 30th, 2018 ~ 3:57 am

@ kay3070

It'll stay between us Kay.

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:45 pm

@ Pink Balloon

There should be no secrets kept from a Mistress. I think you pair of pink sissies would both benefit greatly with a visit from my good friend Mr Paddle.

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 1:38 pm

@ kay3070
Well well well my pretty little naughty nappied pansy it would appear from the many comments here how gleeful your fellow sissies are to witness Kay Kandyfloss getting her comeuppance and so I think that seals the deal that far from your humiliation being at an end, we need to continue in this vein.

I see you are full of pleading and apparent remorse although at the same time you are rather foolishly attempting to keep secrets behind my back - what did you think I wouldn't notice? That indicates your apology and subsequent promise of good behaviour to be nothing more than a sham, clearly a Mistress cannot tolerate a sissy mocking her in this way so it looks like your punishment and public humiliation will have to be upped until there is a genuine sign of improvement.

As for spurting in your nappy that is beyond the pale and proves that your tiny baby cock is not ready for panties other than baby panties and you will have to be kept in nappies and baby dresses until you start behaving like a big girl, a large vibrating plug to train that naughty sissy hole for the real thing, punishment dummy to keep you from whining and maybe we should fit some nice clangy bells to your wrist so everyone knows there is a sissy approaching (oh yes you will be going outside maybe have you mince down the high street with your dress pinned up too). Oh and I shouldn't forget your bottom will be throbbing after I've topped up the stripe marks.

No doubt there will be some sobs of shame but you really only have yourself to blame my pretty little fairy with you resisting your babified status and giving me plenty of backchat when I was reading the riot act, make no mistake about it there is plenty more punishment and humiliation awaiting you and we've barely got started.

Quote

◆

Pink Balloon

Posted September 30th, 2018 ~ 7:14 pm

@ sarahsissyboots

Eep, y-y-yes, understood. *curtsy*

Quote

Sissybeckyfunstuff

Posted September 27th, 2018 ~ 5:28 am

My How the tables have turned! :)

Quote

◆

sarahsissyboots

Posted September 30th, 2018 ~ 12:50 pm

@ Sissybeckyfunstuff

Oh yes becky revenge is a dish best served sissy (giggles). Of course as we do switch its not lost on us that any punishment or humiliation we serve up could well come home to roost when its our turn on the spanking stool.

Quote

Tags:

nappies sissified mistress petticoat punishment

Categories:

Diaper Lovers

Feminization

Dominating Mistress Or Master

Spankings