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Transforming Babysitter

by Y Lee Coyote

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 07 Sep 2015

The following story is fiction about youth who is subjected to CP to change his behavior.  The story contains scenes of spanking with various implements, humiliation and young femdom.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

This work is copyright by the author and commercial use is prohibited without permission.  Personal/private copies are permitted only if complete including the copyright notice.

The author would appreciate your comments – pro and con, including constructive criticism, and suggestions.  Please take a moment to e-mail.

There was exactly one thing that fourteen-year-old Ricky and his stepmother, Mrs. Hollins, agreed about.  That was that they hated each other.  Ricky could not understand why his father had married such an evil witch or was she a bitch or even both.  Boy and woman were at each other throats constantly but fortunately not literally.  Mrs. Hollins had decided that she would break Ricky so that he would be a docile, obedient and respectful boy just like she had broken his father and now controlled him and thus his fortune.  There’s no need to mention whom she thought, er, knew was the superior sex.

For vacation Mrs. Hollins had arranged the stay in a cabin in the forest where the nearest neighbor was supposedly an unimaginable distance away.  Just to discourage the boy from trying to run away when they drove up to the place she made several extra loops on the seemingly identical forest roads so he would be very confused and even think they were even deeper in the forest and thus further from civilization than they were.

In preparation for the real transformation, she gave the boy a drug that would weaken his will power secretly hidden in his milk before bring in Shari.  Shari was from a clan of feminists and for years had been dominating all the boys she encountered especially her brothers even though she was still a tween.  A cover story had been made for Ricky had been told by his evil step mom I have to be away a couple of days, boy.  I’ve arranged for a sitter since you can NOT be alone.  Ricky objected, as expected, assuming that it would be some bossy girl.  You’ll be pleased to know that I’ve arranged for Kent to stay with you.  He is a year older than you and knows about the woods.  That surprised and pacified Ricky.

Just as expected the old pickup truck chugged through at ten bring a load of groceries from the little town’s general store.  Ricky helped the delivery guy carry the cartons inside.  When the truck drove off Shari rather than the expected Kent was standing there.  She explained: My brother, Kent, has been taken ill and has to remain at home.  Knowing you had plans, I came in his stead, Mrs. Hollins, rather than causing you a great problem.

Ricky objected again even pointing out she was younger.  I already have my sitters’ licence and lots of experience. was the young lady’s emphatic response.  In a couple of days, you will agree that I can do this job.  Little did Ricky suspect how true that would be although then he could not possibly envision how it would be.

That was most thoughtful of you, Shari.  Ricky, that is more than enough. said his mother sharply.  Shari is your sitter and you will obey her or else.  She has full authority to punish you; even to spank you as she sees fit.  End of discussion.  With that she got into her car and drove off leaving the two effectively stranded.  Little did Ricky know that Shari was a wild cat far fiercer than his mom.  His ignorance would soon be cured the hard way through painful experience.

* * * * * * * * * *

Bring my suitcase in, Ricky.

Bring it yourself.  I’m not your servant.

I’m telling you to bring it in.  If I have to force you there will be unpleasant consequences for you.

He laughed observing that she was younger, smaller and merely a girl.  NO! he repeated very sure of himself.

That unleashed the wild cat.  In a flash Shari moved.  She got hold of Ricky’s wrist and twisted his arm painfully up his back.  He tried to free himself but she knew a lot more tricks than he did and was even stronger.  Now, pick it up, boy, and take it inside.

OK.  OK.  Let go of me.

That is Yes, Ma’am. boy.  Understand?

Yes, Ma’am.  She did not let go of him but keep a tight hold as he carried the suitcase to the bedroom.

You have earned a spanking, boy.  Open your belt and push down your shorts and undies.

What?  No way!  You can’t do that.

Yes way!  I can and I will!  It would be better if you cooperate.  Pants down, now, boy.  It wasn’t until she increased the pressure on his arm that he obeyed.  It took an extra bit of pressure to get him to drop his underpants but he did that also.  He then got over her lap as directed.  He was already confused especially by her ability to inflict so much pain seemingly effortlessly.

The first spank was hard and surprised him especially from a girl.  Initially, he remained silent but that quickly became increasingly difficult.  After a while, he succumbed to the hard spanking and began to beg for it to stop.  Only after he was sobbing a bit and had promised to obey, did she stop spanking.  She directed him to stand in a corner with his hands on his head after he removed his shirt like a well-spanked little boy should.  There was not any need to remove his pants as he had already kicked them off.

As Ricky stood in the corner, naked with his tail on fire he was perplexed.  Shari was younger and smaller than he was yet she had manhandled (girl-handled?) him such that he was totally at her mercy.  He had even, shamefully, cried a little and that was just from a hand spanking.  He was acutely aware that not only was he naked but that she had seen all of him including all of his most private places.

Eventually, Shari summoned him from the corner.  Ricky stood in front of her with his hands covering his junk.  That got him yelled at sharply.  Hands at your sides, boy!  I’ve already seen your little teeny-tiny worm of a pee-pee and you ain’t got anything to hide.  My kid brother has a bigger one and he doesn’t cry as much as you do from a spanking.  In truth, none of these statements were true but just part of the plan to make Ricky feel more babyish and less self-confident.

Now go set the table while I get lunch, boy. she ordered.  Ricky looked for his clothes but they were not about and she informed him.  Naughty boys who get spanked stay naked with their teeny-tiny pee-pees and red bottoms on display.  Now get to it or you get another spanking.

As they ate, Ricky told him that the next few days could be pleasant or otherwise.  If you do as you are told, then they will be pleasant.  If you are naughty, disobedient or even uncooperative then you will be spanked harder and harder each time.  Do you understand?

Yes, Ma’am. he said quietly already fearful of his young sitter.  After lunch and after clearing the table, Ricky ran off to hide in his room.  He remained there until called for dinner.  At dinner Ricky explained the rules which Ricky did not like and thought that they were for little kids not a fourteen-year-old like himself.  These are the rules, boy.  If you break them, I will spank you.  It’s that simple.  Is there anything that you don’t understand?  He shook his head and she added: Good.

After the clean up was finished, Ricky announced that it was time for Ricky to get a proper haircut so that he would not look like a girl.  As he tried to get away, Shari grabbed him and pressed on a pain pressure point.  It was like she pressed like a super pain button and he collapsed from the excruciating pain.  This was to convince him it was going to happen no matter how much he liked his long locks and it would be shorter if he was spanked first.  Ricky unhappily sat on a stool on the porch while Ricky buzzed his head using a quarter inch (seven mm) glide giving him a crew cut.  He might have even liked it had it been his idea, but since it was forced on him he felt violated.

Shari did not have any patience when Ricky objected to getting a bath.  I can shower myself. he insisted.  She pushed him over the porch railing and used Ricky’s own sandal to roast his ass for the second time that day.  The WHACKS were very hard and Ricky could not help but to howl.  Very quickly he agreed to be bathed and the spanking stopped.  She lead him to the bathtub like he was a little boy.

It was Ricky first bath in more than a decade.  He was not happy and since he did not keep his eyes tightly shut, the shampoo got into them when she rinsed his hair giving him more to be unhappy about.  He could not decide which was worse – her handling his junk to wash it or scrubbing his crack noting how he did not wipe properly.  Since he refused to tinkle after brushing his teeth, she pulled him over her lap for the third spanking of the day, this time using the convenient bath brush.  He tinkled even as he cried and she watched.

Ricky was not a happy puppy when she tucked him in at seven with warning to stay in bed or else.  With the way his bottom hurt he was quite afraid to do other than she ordered.

Shari, on the other hand, was quite delighted at how things were going.  She saw Ricky was a weak (both physically and mentally) wimp male – a common example of the weaker gender and her assignment was going to be easy.

* * * * * * * * * *

Ricky did not sleep well at all.  Not only did his bottom (as he was thinking of it in a little boy mode) hurt something awful but he was terribly confused.  This wildcat of a girl – younger and smaller than he – had totally taken control of him and spanked him three times in just one day.  He thought of running away but knew he was deep in the forest and had been totally confused about directions during the winding twisting ride here from the little town.  Being lost and starving in the woods full of hungry bears and wolves was even more terrifying.  A young man would take some food and take his chances but a little boy with an under sized pee-pee who was whipped by a girl could not even imagine doing such a thing.  He would have to suffer here and hope she would not spank him again.

In the morning Shari was all smiles and joy when she called him for breakfast but she was just as tough as the first day.  Ricky started to get dressed but she stopped him.  I told you that you lose your pants until the next morning when you are spanked, little one.  Yesterday, you got three spankings so no pants today.  If you manage not to get spanked today, then I’ll let you have pants tomorrow, boy.

Ricky sensed that it was hopeless to ask for a reprieve so he remained silent.  He tried to tell himself that it did not matter since she had seen everything close up and even washed it.  His head accepted that but not his heart.

Shari made sure to keep up the pressure by reviewing the rules and making Ricky say that he should be spanked whenever he violated any of them and whenever he disobeyed her.  Although he did not want to go anywhere except his room because he was pantless, she insisted that they go for an hour’s walk for some exercise.  He was terribly afraid of meeting anyone but knew that she would spank him if he refused.

He had some thoughts that perhaps he could learn about the woods a bit but she returned just by retracing the outbound route so that he failed to gain any useful information.

Ricky managed to get through the day unspanked even submitting to being bathed again which he hated.  However, he did keep his eyes tightly closed and did not get shampoo in them.  He slept better not knowing what was in store for the next day.

Shari was most pleased with herself having decided that Ricky was a classic case and easy to dominate.

* * * * * * * * * *

Ricky asked the first thing in the morning if he might get dressed.  He was very careful to ask super politely not wanting to risk angering Shari.  She agreed but said after breakfast.  He managed not to try to cover his nakedness and found it was easier than initially for he knew that she had seen everything and even washed it twice.

Ricky cleared the dishes away in record time anxious to get dressed.  They went to his room and Shari got a T-shirt and shorts from his dresser that Ricky had never seen before.  He wanted his regular clothes but Shari insisted that these were the proper ones for a little boy like him but he was welcome to stay naked if he wished.  Rather than nakedness he opted for the Tiny Toons T-shirt and the short-shorts with an elastic waist but neither fly nor pockets both of which were undersized and tight.

Ricky reasoned that at least he would be dressed when his stepmother returned and she would not see him naked like a baby.  Shari also instructed him about how to speak respectfully to her and warned him that if he did not he would get spanked.

After lunch, Shari got on Ricky’s case to make sure that he knew how to talk to his mother when she returned.  Shari deliberately taunted Ricky until she could announce Boy, you have been arguing with me for sometime.  I know how to stop it.  You are getting a spanking – NOW!  The boy was appalled and begged forgiveness.  Of course, none was forthcoming; only a spanking would be.

They were on the porch so it was there that Ricky was to be spanked.  He quickly stripped knowing that any delay would annoy her and extend the spanking.  Once naked, he got over her lap and she began to spank him with her hand hard.  What Ricky did not know was this was planned and his mom was watching from the woods so that she could drive up and catch her stepson being spanked naked.

It was when Shari stopped that Ricky learned that his mom was watching.  Of course, then it was too late and she had also seen his naked body.  Shari told him to greet his mother as practiced, forcing him to fully expose his teary face and nakedness before being sent to the corner.  Mrs. Hollins was totally delighted at what had happened while Ricky was totally mortified.  It is totally impossible for a teenaged boy to act like a male chauvinistic pig in his state.  As he stood in the corner, he heard Shari reporting all that had happened including the four spankings which only further depressed him.

After his corner time was up, Ricky got a very long lecture about how terrible his conduct was and that things would be different now.  Once again he hid in his room until dinner after which Shari gave him another bath with his mother watching all and then tucking him in for the night.

* * * * * * * * * *

The next day, again in his little boy clothes, his mom required him to do stuff rather than hide so he had to walk about the woods with Shari.  She selected another route this time and they encountered twelve-year-old Ruby and her thirteen-year-old brother Tyler.  Shari introduced him This is Ricky, the naughty fourteen-year-old I told you I was sitting.  I’ve had to spank him several times and bath him.  This amused the siblings but embarrassed Ricky to the point of blushing and wishing he was dead.

Not surprising as he looks like he is only eight with that haircut and those clothes. observed Ruby.

The siblings were heading to a swimming hole and Shari decided that they should join them.  The girls, it turned out had swim gear on under their shorts and tops while Tyler simply lost his shorts and jumped into the refreshing water.  Ricky was resistant to stripping in front of the others and Shari had to encourage him.  Your mom wanted you to get some exercise, so strip and get into the water unless you want me to strip and spank you first.  It was an offer he could not refuse so he stripped and jumped in.  He was mortified when Ruby noted how underdeveloped he was compared to her brother who was a bit younger.  In spite of himself he did enjoy the swimming although he could not understand how Tyler did not care about being naked around the girls.

They have seen me nude since I was little.  Yawn.  Yawn.  Who cares? he said with a laugh.  Ruby helps Mom measure me every six months to keep track of how I’m growing.  She was just as thrilled as I was when I got pubes.  Ricky didn’t know what to say as he was still bald as a baby.

Although he had been reluctant to go swimming, Ricky did not want to get out of the water when Shari said it was time to return home.  It took many tries to convince him and once he did Shari announced that he had earned a spanking for his obstinate behavior.

Absolutely, but you should use a switch.  Tyler please cut one for Shari. said Ruby helpfully.  In just moments he returned with a nice one.  When he switched it through the air it made quite the swoosh scaring Ricky.

Thank you, Tyler.  Ricky – bend over that log for your switching. said Shari in her command voice.  Once he was in position, she did not waste any time but immediately struck.  He howled and jumped up.

Back into position, boy! she barked.  Please hold him down, Tyler.

Shari gave him some ten cuts for which he howled a lot but thanks to Tyler he remained in position.  He was extra subdued for the rest of the day.  He was quite happy that Shari got picked up that evening.  Of course, at bedtime (early, of course, since he had been naughty) he was not so sure any more because it was Mom who was bathing him and getting a closeup of his entire body.  He was most unhappy when she tucked him in for the night.

When they returned home a few days later she had spanked him also.  He sat quietly on the trip listening to her lecture him about how things were going to be different from now on.  How he was going to be a good obedient and mindful boy or else!

The End

© Copyright A.I.L.  August 28, 2015

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