The following story is fiction about a boy and his babysitter and her kid sister and his hopes to get even for past wrongs. The story contains scenes of spanking, strapping and shaving. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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There are many ways of saying it. "As twig is bent, the tree will grow" will suffice. I was only nine when I made the wrong choice and took the easy way rather than the proper way. Over the course of a year, I repeated that decision several times until it wasn't a choice for me any longer. In some ways, I'm like an insect who has landed on a pitcher plant. It not a good place to take off from so I try to walk up but inexorably slide down closer to the deadly acid pool at the bottom. I better go back and start at the beginning.
I was only nine when Ellen started to be my babysitter. She was a big girl, almost a teenager which at the time seemed very old to me. Ellen liked be a little mommy and she soon had me loving her getting me ready for bed. Although, Mother just said: "It's bedtime." and I was expected to be "a big boy" and undress, take a bath, brush my teeth and urinate all by myself, this is not what happed when was Ellen sitting me. She made a game of it and I did not have to do anything for she undressed me and washed me in the tub. I still brushed my teeth and urinated although under her close supervision. I was too young to be shy (i.e., modest) at the beginning and then when I was older it was what I was used to so it continued. I was often naked in the house and yard when I was young and usually did not dress until after breakfast for school. I even slept naked.
My parents were pretty strict and believed that spanking was the time proven method for correction of naughty boys. It really was not clear what was meant when my folks told me: "Jimmy, you had better listen to Ms. Ellen or you will get a spanking." I thought that it meant that I would get spanked by Mom or Dad the next day but Ellen insisted that it meant that she could spank me. She was bigger and stronger and when I got into a contrary state, she spanked me. It was not traumatic that she yanked down my shorts and briefs for she often saw me naked but it was when she pulled me over her lap and had me crying in just a few minutes of using her hand to spank my little bottom. I was still in the corner when the folks returned and she got praised for turning my butt bright red. I no longer had any doubts about her authority after she was complimented for that first spanking.
Frequently, Ellen would bring her kid sister, Kari, who was three years younger than I. She thought of herself of as "mommy's little helper". I objected that she would see me naked but I quickly lost that discussion. I started to yell at Ellen and she told me to be quiet. I was not. "OK, I'll give you something to yell about." That's right, she meant a spanking. A bare bottom spanking with Kari watching.
Ellen quickly undid my shorts and within seconds I had lost not only them but also my briefs. Of course, Kari saw my boy parts and then watched as her sister spanked my bare bottom. When I was stood up I was only interested in rubbing my hot tushie and doing the spankers' dance. By the time I had recovered Kari had studied my stuff and I soon learnt that I was smaller than her cousin Dakota who was a year younger than I and her cousin Jake who was fourteen and even had hair about his penis.
That evening Kari watched me get bathed by Ellen and even helped to dry me. The next few days got very hot and both Kari and I got to run around in the lawn sprinklers. I was completely naked since that was how I always did it and both of them had seen me before so there was not anything to hide. Kari was in a two-piece bathing suit because that's what ladies – even little ladies – wore.
After the third spanking Ellen gave me with her kid sister watching, Kari started to assist. While I was over Ellen's lap, Kari would give me a few spanks. They were softer than Ellen's, of course, so I only made minor objections because I was then spanked less by Ellen. Oh, that was an evil trap and I was continuing my descent.
After a few months, my babysitter had a full-fledged assistant. They shared all the duties of the babysitter. Even though Ellen was always there, her little sister, who was younger than I, out ranked me and I learnt to obey her just as I did Ellen. I was still frequently naked around the house and that did not change when they were there.
It was when I was eleven that I made that big decision which still haunts me to this day. I was offered the choice of Kari rather than Ellen spanking me. I would have to get over her lap and submit to her spanking me. At first, these spanking were gentler, but soon Kari learnt some tricks and started to use a flip-flop or a hairbrush increasing her effectiveness. She was making me cry even more than Ellen did. I tried to stop it, but they said they were in charge and they insisted that they would now decide who spanked me and how.
I was trapped in this situation for about a year until I turned twelve and my folks decided that I did not require a babysitter any longer. I thought that I was free but Mother still insisted that I not get dressed until after breakfast until I grew pubes. "The air is good for you and little boys don't need to be very modest." she explained.
* * * * * * * * * *
It seemed a great idea when Kari's 'rents asked me to babysit her when her big sister was not available. I was already a teenager then and she was only ten-years-old. As you can imagine, I thought about getting Kari naked, giving her a bath and, most of all, spanking her. It did not work out that way at all. On the first gig her mother informed me that Kari needed only minimal supervision and was more than capable of showering by herself and the like. Also, that her good little girl was not spanked like I was. I resigned myself that just being in charge would be sufficient.
Once we were alone, Kari happily reminisced about times past especially when I was naked and over her little lap for spankings. I told her that she was just her big sister's proxy and she had not really been in charge of me. "Just forget it." I finished up.
She laughed and grinned. "I'm certainly not going to forget it. It was lots of fun spanking you, bathing you and watching your little pee-pee flop about when you were running a round naked, especially in sprinklers. I'm sure that you still get spanked when you're a naughty little boy."
«Hell,» I thought, «how the fuck did she know that.» "That's all past." I lied, trying to be authoritative. It turned out that she did not need very much watching and she even decided to go to bed early. I wished that I could bathe her like she had me but that was impossible. I got bored soon after she went to bed. I started to explore (otherwise known as being nosy) and soon found her dad's stash of hot magazines. I was no longer bored for they were intensely interesting. I even opened my jeans so I could play with my junk as I read.
I was startled when she spoke. "I see that you still have just a teeny-tiny little pee-pee without any hair, Jimmy." I looked up and she was standing there. "That's the best shot of all." I grabbed for her phone but she laughed. "It's too late, little boy, I send them already."
I started to fix my clothes but she stopped me. "I'm sure my folks and yours will be very interested in these pictures of you snooping and playing with yourself. Among other things you surely will get spanked."
She was, to my deep regret, quite right about that. Without thinking, I played right into her hands. "Please, Kari, don't show them. Please."
"But then you'll escape your punishment certainly including a well-earned spanking, Jimmy. That would be very wrong." She was smiling – evilly. I did not know what to say. It was at least a minute before she spoke again. "Of course, if you get spanked now, then there wouldn't be any need to show them." Again she paused and the horrid truth hit me hard. She wanted to spank me and just like the very first time it would be easier than owning up properly although obviously I wasn't thinking it through.
She, on the other hand, knew exactly what she wanted. It was to be like old times when she was "mommy's little helper" and babysitting me. After she made me put the magazines back, I followed her to her bedroom. She undressed me completely just like she did when her sister was sitting me. Now it felt very wrong but I was helpless because of those pictures she had. When I covered my junk with my hands, she scoffed. "I've seen your little pee-pee many, many times, Jimmy. You don't have anything to hide."
Reluctantly, I moved my hands to my side and she stared. "It has not grown very much at all and no hair either. My cousin Dakota is much bigger and even has a big bush like I do." Damn, her cousin is a year younger than I. I felt even smaller.
"I'm getting hair." I said defensively. "They are just starting. Look close." She did but it did not help my argument any. She sat on her bed and pulled me across her lap. She planned well for much of my weight was supported by the bed. She started with her hand which did not hurt much but that was just a preliminary for she then switched to her hairbrush. Now that really hurt for she spanked me long and hard with it. I was even crying much to her delight by the time that she stopped. I knew I was very well punished little boy then.
I was not expecting the next thing at all. She rolled me over while I was on her lap. She carefully examined my crotch and declared that I had almost two dozen hairs starting to grow. I was very proud that was happening. "Naughty little crybabies don't have pubic hair. Such hair is for grownups."
«What the hell was she talking about?» I wondered.
Then I felt her drag something over my pubis. "There; all taken care of. No more nasty hairs, Jimmy. You're a proper LITTLE BOY now." It was a safety razor that she had dragged over me setting me back months in terms of my anxiously awaited hair.
She took me into the bathroom and washed my face and held my hose while I pee-peed. Then back in the bedroom, she took some more pictures before she dressed me. "Don't forget that little hairless boys, like you, should only wear tightie-whities and I'll be checking up on you to make sure you stop wearing boxers."
When she got into bed, she reminded me that she still had those pictures and that I had better be her obedient little boy. "I'm going to tell Mom that you're the best babysitter and then we'll see each other a lot."
All I could think of while I waited for her parents to return was the mess I was in. I knew that I couldn't tell anyone that the ten-year-old girl I was babysitting had stripped, shaved and spanked thirteen-year-old me as if I had only been five-year-old like Kari had done. All I could do was hope that she would not tell anyone.
* * * * * * * * * *
It was only three days later that Mom told me that she had spoken with Kari's mother and reported how pleased she was with the babysitting job I had done. "Kari was very happy with me and thought that I was the best babysitter ever. I had the job for as long as I wanted it and was needed." I was trapped. If I refused to babysit Kari, she had those incriminating pictures of me which would get me into big trouble. I was trapped.
I tried to use such praise as a reason to get dressed before breakfast. I'm not a little boy anymore, Mother. I'm a teenager already." I said. Mother refused saying that I still did not have pubic hair. Of course, I did but I certainly could not tell her that Kari had shaved them off.
It was after the second time I sat Kari, while I was eating breakfast – naked, of course, when Kari stopped by. I stayed seated, trying to hide that I was naked. She was all sunshine. She just wanted to thank me for being a great babysitter. I grumbled a response and Mother pounced on me that I should be more polite. "Stand up and reply properly, young man to the young lady."
"But I'm not dressed." I whined.
"Don't be silly boy, Kari saw you many times when she helped Ellen sit you and you haven't changed any."
"It's OK, Ma'am. I understand."
But Mom did not understand at all and made me stand up and thank Kari for her compliment.
"You're welcome, Jimmy." she said, "And you look just like you did last time I saw you." Mom did not see how she smirked but she now 'officially' knew I was hairless as when I was being babysat by her and Ellen.
Things got worse over the next few months. Every time I sat Kari, she was sure to get me naked, spank me and shave me. In short, she was in charge. She even grilled me about my behavior and I kept confessing stuff that neither my parents nor my teachers knew about. At the beginning I lied about things, of course, but Kari could always tell as if I was Pinocchio and my nose grew with every falsehood. I really had to revert back to briefs and told Mom that they were more comfortable. Fortunately, Kari did not order me to use cartoon briefs.
I must admit that Kari was fair at least about spanking me. She always had a reason usually based on my own confessions. If I was good and did not have anything to confess, then I was not spanked. I always had to strip for her every time and she always used that damn razor.
* * * * * * * * * *
This went on for more than a year. At the beginning I was getting spanked almost every week but things had changed and now it was more like once every five or six weeks. I thought that I was growing up and wished that she would stop shaving me every week. Maybe if she did, then I could grow a bush rather than a few tiny hairs that got mowed down with disgusting regularity.
Of course, I was not always the perfect boy. There was one week where I managed to mess up several times. Three times to be precise. That earned me a mega-spanking from Kari. It seemed like hours that I lay over her leg with my torso on her bed and her leg over mine while she pounded my most sorry tail with her hairbrush. She had been able to make me cry for just one offence and this spanking was for three.
Over and over that hairbrush connected with my naughty bottom turning it into a fiery hot pain center that surely glowed from the novas that she had ignited inside. Even after I was bawling she kept at it. I was reduced to a blubbering baby. I cried for a long time.
It was in the morning that the shit hit the fan. My tail was still afire and first Mother noticed me fidgeting and then got a look at my bottom. She demanded to know what happened. I confessed that Kari had spanked me very hard and that she had many times since I started to babysit her. "Interesting; very interesting. Now go to your room and stay there. Do your homework and don't bother to get dressed." she told me after breakfast.
It was a few hours later that I was called down. Mother and Kari were there and my life was about to undergo a major change. Surprisingly, Mother was pleased for thinking back my behavior had been much better since Kari had been disciplining me. What she said then was not to my liking at all. "Kari is a most mature young lady already. Just look at how her body has developed while you are still a just an immature little boy. She even recognized how you are in need of constant supervision and provided it." I could not help noticing that she already had breasts (albeit still small) and had boasted that she had a bush. It was clear that she was a young lady already.
Then she pronounced my doom. "From now on, Kari is in charge of you with full authority to spank you anywhere and anytime she decides that you need a spanking. You will call her 'Ms. Kari'"
"I'm most honored that you trust me, Margaret." Kari said smiling and using my mother's given name.
"One other thing," Mother added, "I agree with Kari that a little boy who needs oversight like you do, is too immature to have pubes, so she will keep you smooth."
To say that I was horrified would be the understatement of the year. There was not anyway out. Here I was, almost fifteen-years-old and Ms. Kari, a girl only eleven-years-old was in charge of me.
I have slipped completely down into that acid pool for Kari has promised me that I will remain her hairless little boy forever.
© Copyright A.I.L. May 7, 2012
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Last updated: May 7, 2012