“Ken's Sissy Buttocks“ Chapter 1

Of course you are not a girl dear, you're a sissy panty boy; anyway these are boys shorts and your Gran went to a lot of trouble making them didn't you mum?

Jessica said in a determined manner. ”Yes dear I did and they are definitely boys shorts. They suit his round buttocks very nicely in my opinion,” replied Angela his Gran as she admired the rotundity of her grandson's bared buttocks.

Now dear, please thank your Gran in a nice lisping voice.

"Thwank you Gwanny." Ken lisped still not used to doing this terrible voice they made him use at times.

"That's a good sissy boy. I know they are not normal boys shorts dearie but you are not a normal boy are you, Ken? You know Miss Blouse was quite insistent and particular in her instructions on how you were to look, and there was no point in trying to contain this bottom of yours in such fine flimsy material.

You wouldn't want your bare buttocks bursting out of your shorts if we had visitors would you? That would be very embarrassing. Best to leave them totally bared and that way everyone can admire the way they flounce about as you walk up and down. It would be a total shame to cover such buttocks wouldn't it mum? Jessica said as she palmed the right cheek of her son's backside tenderly.

It certainly would, dear and I certainly have no intention of unbuttoning and undoing those other shorts of his several times a day when I need to spank and cane his bottom.

No, they must be kept fully bared for the next few months as his discipline will need to be increased anyway his Gran retorted, feeling a heaving in her bosom as she thought about the way the boy's buttocks quivered under a stern and prolonged caning.

"Do you hear that Ken? Mum is being so considerate for you and you know she puts a lot of effort into chastising your bare plump backside every day. You are so lucky to have such a Gran. You do want these naughty cheeks of yours bare and ready for her every time she needs to discipline you don't you dear, hmm? Jessica asked admiring the deep blush on her pretty son's face.

"But I don't like the cane Mummy." Ken said helplessly.

I know you don't dear, but it wouldn't be much use if you did like it, now would it? You know your Gran and I only want the best for you and keeping your bare backside well chastised is part of your training. I think a nice ribboned bow from each wrist attaching at the penis pouch here may be a nice touch mum, or even attached to his frilly tit itself.

We simply have to work on his wrists and make them hang as a proper fairy boy would. That way we could instruct him to keep his penis pouch pulled up tightly all the time. Jessica said as she patted the tightly encased frontal pouch.

She marveled at how the front of the shorts were so tightly encasing but the back simply consisted of a flimsy string of silk which disappeared deep into the boys bottom cheeks. They were still full shorts she insisted to herself.

"Yes dear. I will have a look at that later," his Gran mused as she felt that may be a nice touch.

"Now is time for your blouse Ken; these pert nipples have been exposed for long enough I think. Can you pass me his bra mum please? Thank you."

My, what a big bra this is. You are going to be quite the busty sissy aren't you dear? How many pairs of your knickers will be needed for this one?" Jessica asked her mum as she looked towards the pile of silk Granny knickers on the sofa beside her mum.

"I have twelve pairs here, six for each cup. That should do. We can remove the ones we are wearing if we need more Susan," Angela replied, thinking how nice it may be to remove her daughter's warm pantaloons and her own slightly damp ones to help the boy be shown as a big bosomed sissy.

With my six pairs of Gran's bloomers, you are going to be quite a tease aren't you boy?

"Pass me the wooden spoon mum; I want to redden up these boobies of his before we encase them in his new big bra."

Won't that be nice dear, having your nice boobies peeking thru all of Gran's knickers as nice and red and swollen as they should be?” Jessica asked as she tweaked one of the boy's prominent nipples making him squeal.

"Eeooww No, no Mummy please! 

"No? Now you know Mummy doesn't like you uttering that naughty word don't you dear? And you know how well those girly nipples of yours simply beg to be chastised sternly? Jessica commented restraining the thoughts of delight she felt about walloping the boy's nipples till they glowed and became twice their normal prominence. How he came to have such mounds and pointed nipples she simply didn't know but she knew they made him look so pretty and matched his nice round facial cheeks. She had of course been training his nipples for a few years now and she and her Mum often spent 20 minutes pulling, pinching and tweaking on them as he squealed loudly.

Her Mum picked up the larger of the two wooden spoons saying "I think he needs this one dear as this is a very big bra and we want his boobies pushing against my knickers," getting more excited at the thought of her daughter spanking her grandson's wobbles hard.

When it came to naming parts of Ken's body, Jessica and her mum always used as many varieties as possible all designed to shame the blushing boy.

His bottom came in for much of this naming, along with his breasts and penis.

Words like, plump buttocks, fat cheeks, wiggly butt, fleshy globes, plumpers, pouty bot, botty bot, sweet cheeks, botty slot and those inviting deep buttocks of his all helped describe the boy's bottom.

For his breasts it was, titties, boobies, hooters, melons, roundies, nipplettes, suckies, twinkies, tweakys, boosies and floppies. His penis varied from, pee pee, wee wee, winkie, nubbin, jolly stick, sissy tit, munchies, dilly and clitty stick.

All of these phrases and many more, helped keep the boy confused and shamed and left him in no doubt of how his Mother and Grandmother saw the boy in their eyes: a total effeminate sissy trollop and felt he always would be.

Ken was 15 and had always been raised in a strict manner from a very young age.

His father having been killed in service when he was four, simply allowed his Mother to treat him in an even stricter manner. As he grew, his Mother noticed his development, particularly at his regular bath times. His big blue eyes seemed to get bigger and he always looked like he was in shock of something. His nicely framed pretty face, with those high cheekbones and pouting lips.

She often looked into a mirror examining her own lips as she considered her son’s. They were even poutier than hers and she would squeeze his cheeks tightly and relish in the picture they formed, like they were begging to be kissed most firmly.
He had a slender neck with nice rounded shoulders and then of course those boobies. Jessica often marveled at the boy's over-sized red nipples which seemed to the general observer to be in a constant state of excitement.

Of course Jessica knew differently and that they just naturally formed that way. The mounds of his breasts were also a mystery and she felt it was due to the natural genes running through the boy and the sissy inside screaming to get out, even though he found it difficult to accept it. However, accept it he would if Jessica and her Mother had anything to do with it.

When aged 8 and 9 and the boy started inquiring innocently about long trousers, Jessica made her first conscious decision and had a good chat with the boy about it. She tried her best to explain that many boys only wore long pants outside and changed into short ones when they got home.

She knew Ken didn't mix with many boys, if any at all, and he would find this difficult to confirm.

She also told him that the boys who did wear long pants were exceptionally well behaved boys and the need for constant routine spankings of their upper thighs and bare bottoms had passed away somewhat and had been reduced to a single spanking at their bedtimes.

However, she told him fondly, while he continued to be the way he was, he couldn't expect her or his Gran to be unbuttoning and pulling down his pants and undies several times each day for the times when he needed to be spanked. It was much easier to allow him to continue to wear pants but they just had to be the sort he wore, extremely tight fitting and extremely short, exposing a good portion of his bared buttocks.

In fact, she told him quietly but firmly, she had decided to make his shorts even shorter now as his bottom was developing in a way that it was becoming harder and harder to keep his buttock cheeks constrained in tight shorts that covered some of his cheeks.

She would of course consider long pants for him if he wished, however that would mean him having to be kept fully bare bottomed at home all the time and perhaps even nude, so he could be spanked as needed.

These types of chats helped keep the boy under her ways and she would adapt them as he got older. Her decision however was not of course to even consider long pants for the boy, but to start him on even shorter and more revealing pants for the coming few years.

She even decided on punishment pants for him which while full and buttoned at the front, completely exposed every inch of his full round bare bottom for her hand, wooden spoon, spatula and hairbrush during the day. He would be sentenced to wear these for weeks at a time and she found he was delighted to be let back into his normal short pants.

This all helped develop the boy's attitude towards his Mother and Grandmother's plans for him to be the happy wife of a rich well-hung husband with an obsession with sissies and anal intercourse.

++++++++++++++++

pantywaist-ken

"Obey! Be kind to your behind." (p.w.-ken too fond of playing with his idiot stick)