The following story is fiction about a tween boy who mistreats his less developed sitter. The sitter gets even with the help of his 'identical' cousin teaching the boy a long lasting lesson. The story contains scenes of spanking, strapping, shaving and gay sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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I was new to the neighborhood and it seemed that all the usual ways for a youth to earn some bread were over booked. Everyone already had contacts. Householders knew the available pool of guys. I was new and unknown and far, far down the list to call if even on it. I kept trying, however. I continued posting in the supermarket and community center and hoped that someone would get sick or that there would be a big snow storm.
Then I got the call. The Ronald's regular sitter was sick and, although they did not say so, everyone else was booked as it was busy night in town. It promised to be an easy job for Russ was eleven and should be able to take care of himself. I, at fourteen, just had to be there to satisfy the state law that under twelves may not be left alone. I accepted the gig eagerly.
I immediately saw that Russ was almost my size being on the large size for his age while I was on the small size. I made sure that I got the important information from his parents about where to reach them, emergencies and Russ's rules. The rules applied throughout the family so that when cousins and friends visited everyone would be subjected to the same, consistent rules. (That explained why they had age conditionals in them.) It was not that surprising to learn that one of those rules was that naughty boys get spanked and that clears the slate. Although it would not be for a couple of hours that I would learn how important that rule was. Even when Russ told me that his sitters had spanked him and had not told his folks, I did not think much about the rule.
We had the dinner Russ's mom had left and I made sure that he had done his homework before we got to watch the TV. It was then that I spread my stuff out on the kitchen table to get to my homework while Russ went off to get ready for bed. When he came down a few minutes later I was looking at a comic book a friend had stuck into my book bag and I was surprised that he was nude. An even bigger surprise was that he was well into puberty, already having a thick forest of pubes and a cock that was substantially more than boy sized. He was totally blasé about it. He even explained that he had been sleeping nude before he turned ten.
It was a bit unnerving to me because I had not yet started puberty. I was as bald as a baby and with only a boy sized package. I already knew I that I was maturing much later than most of my classmates from the showers in school. I figured that it would be better not to let Russ know since those with hair tended to lord it over those of us without. He saw my school stuff spread out on the table and picked up my assignment book. He took only a few seconds to see that I had not done all my assignments for the next day. He called me on it. I said that "I had lots of time to do it."© YLeeCoyote
"That's no excuse, young man, for having watched TV before. Sometimes things take longer than you expect or you get distracted by something – like a comic book." he said in a loud, booming, low register voice, sounding just like my Dad had only week ago when he spanked me, and even holding up the evidence. I was flummoxed and couldn't give a coherent response. I felt like a little kid caught with his hand in the cookie jar. Eventually, it all came down to that I had broken the rules and thus had earned a spanking. His self confidence was amazing. Officially he was in my charge but although he was younger and naked he immediately took charge of me.
I was in a daze when Russ pulled me to my feet, yanked my belt out of my jeans and then opened them. I was making incoherent noises of protest when he yanked them along with my boyish tighty-whities down to my ankles. It happened so fast, like he had practiced, that my head was spinning. It was an automatic reaction that I covered my crotch with my hands which got me into more trouble. "Put your hands aside, LITTLE BOY, you ain't got nothing to hide." Now he knew what I had not wanted him to know and instantly was taking advantage of it.
My self confidence was quite shattered now. In a twinkling of an eye suddenly I was just a naughty little boy about to get another spanking. That it would be from a boy three years younger than I just made everything infinitely worse so that I could not react. Russ turned a chair around. He sat. He pulled me over his lap. He got a good grip on my waist. He next spoke with his hand.
Russ had started to spank me. I yelped at the unexpected sting. Then there was a barrage of spanks. None of them hurt by themselves but collectively I began to feel them. «What was happening?» was roaring through my head as the pain was building in my butt. Then it stopped. I thought it was over until I felt the belt – my own belt – connect with my butt. That carried far more sting then had Russ's hand and it went on forever. Well, of course not forever, but at the time it seemed liked it. I could feel his hard cock poking me as I lay on his lap.
I knew that he was certainly in charge now and he surely knew it also. I was, shamefully, crying like a little boy when Russ stopped spanking me. He stood me up but, weak, I slipped to my knees and my head fell onto his lap. His naked lap with his erect cock sticking up like a lone tree out of the surrounding bushes. As I sobbed, his man scent got into me and affected me. I could not help but to be fascinated by his huge cock, compared to mine own little boy sized one. "You may touch it, boy. The slate is clear now that you've been spanked." he said like an adult in charge.
I did not want to. At least that what I told myself but I was drawn to it like a moth to a flame. It was so close. Russ's hands were on my head and he guided me so that his cock stroked my check. It was so hard yet soft. The tip brushed my lips and it was wet. Automatically, I licked my lips and tasted it. That was new to me for I did not know about pre-cum. Russ was still holding my head right above his rampant cock. I was mesmerized as my crossed eyes tried to focus on his big hard cock.
"Go on, boy, give it a lick so you know what it tastes like." And I did. I had fallen under his spell and after he told me to open my mouth he lowered my head onto his spike. Soon I was sucking him without knowing why and not actually being told to. Russ was stroking my head and telling me "Good boy." It was soothing to hear that since I had just been spanked.
Anyone with any experience would have realized what was about to happen but not naïve me. Suddenly he gripped my head tightly and pushed it all the way down on his shaft. Right afterwards he exploded blasting his ejaculate deep into by gullet. Some I immediately swallowed and the rest filled my mouth. It was a new taste and he told me to swallow and I did. I pulled off of his cock when he released my head. I had given my first blow job without knowing what I was doing.
"I see that you liked that, Kris. Your little pricklet is hard." said a smirking Russ. "We can do this next time, boy. But now it's time for you to do your homework and for me to go to bed. Goodnight, cocksucker. You shouldn't tell my folks about this." He went off to bed. I rubbed my hot red butt and, after checking it out in the mirror, pulled up my pants. I was too confused to get my homework done.
When his folks got home, I told them that all was fine. I slept fitfully that night not sure about anything. Then I worried that the world would end because of me but it did not. Actually, Russ's mother called a few days later. She reported that Russ was happy with me and asked me to sit him again.
* * * * * * * * * *
I never expected such a wonderful outcome when the folks got this new sitter for me. Kris met the legal requirements to be a sitter since he was fourteen but he still a little boy in every other way. I sensed that he was a wimp right away but decided to play it cool. If I was right, he sure would be a better – from my perspective – sitter than those others that Mom has inflicted on me. Those girls all are perverts! They all want to do is to examine my junk. I wouldn't mind that if they would reciprocate like the girls in my classes have done over the years when we played doctor and such. They just want to molest my body for free by giving me a bath and washing my dick. Don't they have boyfriends or brothers to Ms-handle [pun intended]?
Anyway, when Mom told me she had gotten Kris – a boy! – to sit me I was delighted. If he was stuck up, he would leave me alone and if not then we could have fun doing guy stuff. Perhaps I could get him to share his porn like he was a big brother. Now that would be fun!
So, Kris showed up and it was soon clear that he was a goody-goody wimp. He just wanted to follow the rules and I guess that was reasonable. What he did not know was in my neighborhood, the house rules applied to everybody and all the 'rents were entitled to spank everyone for infractions. Actually that made things easier since the rules were uniform. We just had be outside to break them safely – and that was getting easier to do as I was getting older.
The evening went very quietly until after I had my shower. I went downstairs nude and Kris was at the kitchen table with his books spread out but he was reading a comic. When he saw my junk his eyes opened up like saucers. What the hell was he thinking? I knew I was an early bloomer but why was he so interested?
It was obvious that he wasn't the perfect goody-goody that he made out to be because with his school stuff open he was reading a comic. Then I noticed his assignment book and he had a couple of things due in the morning not checked off. I decided to have some fun. "You had no business watching TV, Kris. You haven't done ALL of your assignments." I said boldly, and then added: "THAT IS A SPANKING OFFENCE."
A real guy would have laughed, slapped my butt and sent me off to bed but he didn't. He just looked scared so I pounced. Although he was older than me, I was almost as big and I got him over my lap. Even then he could have fought back but he did not so I spanked him. I had already taken his belt and dropped his pants so I started with my bare hand on his bare butt. A few SPANKS and his ass was turning pink and I was feeling on top of the world. By the time I switched to the belt I was rock hard and he was crying like a little baby boy. Well, I guess that was because he was a little boy. He was totally bald; not even a single pubic hair yet; with only a little boy's pee-pee and wearing tightie-whities. No wonder he had stared at my dense bush and big cock. He must have a hell of a time in the shower in high school.
Spanking him was lots of fun but I stopped. I lifted him up but he just collapsed onto his knees before me and dropped his head into my lap. I held his head and somehow started to move it about. It felt good when my hard cock brushed about his face. I got the sense that he was enthralled by my cock and after a drop of pre-cum got on his lip he licked it. When his mouth was open I guided him down onto my cock. He started to suck it and I was delighted. It was only when I was about to cum that I pushed him down and shot deep into his mouth. He swallowed some of my jizz immediately. After I raised his head and told him to swallow the rest and he did so to my delight.
MY FIRST BLOW JOB! WOW!
I told him to do his homework and I floated off to bed. I was already looking forward to the next time.
* * * * * * * * * *
I encouraged the folks to get Kris the next time they were going out. He must have liked what happened because it was only two weeks later that he was back. This time I was quite prepared knowing that I would have a compliant little wuss to play with. Of course, he could never tell for all the other kids would laugh at him (and do the same if they could) and my 'rents would not have gotten him again. I knew I was safe. I was extra diligent in getting my homework done so that I would have lots of time to play with my new boy-toy again.
I lured Kris up to my room by asking him to help with my homework. After some pious comment about not doing it for me, he came. Then I shoved him down on the bed and told him that he was a naughty boy for what happened the first time and that I was going to spank him for it. The wimp begged me not to but I just pantsed him. Now with his bald pee-pee hanging out I got him over my lap and started to spank him.
I loved how my hand prints showed at first until they all blurred together. Then I switched to a flip flop to really be effective without hurting my hand. It was delightful how the baby howled from that. Even more than the belt which I had not used to its best. Soon his tail was deep red and very hot. His other end was bawling. Of course, my cock was like steel and as he lay there crying, I stripped down.
I smeared some petroleum jelly on my shaft and his butt hole. I was kind and even pushed a couple of fingers into him to lube up the inside. I don't think he knew what was happening yet. I got on my knees between his legs and positioned my rod at his hole and pressed forward. I slipped in and then got a good grip with my arms. I had him now. It was a great joy to have his cherry and even (truth be told) to lose my own virginity and I pumped away hard. This was even better than the bj last time.
I'm sure that he loved it because he had a dry cum as I pounded away at his ass. After I planted my seed in his ass, I withdrew. I sent him to the john to clean up and then I showered and sacked out to relive the experience.
I WAS ELATED!
* * * * * * * * * *
The second time sitting Russ was a far greater disaster personally for me than even the first time. Russ was terribly aggressive and after spanking me even raped me. I know that I should have fought back both times but I'm not that sort. I guess that I'm a wuss or worse.
I should tell but I'm too ashamed to admit that an eleven-year-old did that to me. I would have stopped sitting for him but he told me that he would tell and then everyone will get a piece of me. Besides, I need the money. I'm trapped.
I'm sure that the next time will even be worse. I've been worrying about what might happen. It was a miracle that I was saved.
My cousin Kory is like a twin brother. Not only do we share the same birthday but we look like twins. He showed up unexpectedly for two nights because his folks suddenly had to take a two day trip. Kory got the entire story out of me in just a few hours on Friday night. There are two ways that we are not alike. First, he is not a wuss like me but aggressive like Russ. Second, he started puberty two years ago and got the hair and junk to prove it.
"I got the solution, Cuz. I will take the babysitting job for you. When that uppity brat tries his funny business, I'll give him his comeuppance. He'll be a meek little boy when I'm finished with him."
I'll let my cousin tell you how he handled that insolent brat.
* * * * * * * * * *
I arrived before Russ's parents left and they thought I was Kris as did Russ. The deception worked. In front of his parents, he gave me a great big hug and called me his favorite sitter. Russ was most anxious for his folks to go so that he could assault me. He was in for a big surprise.
Right away he started to show how obnoxious he could be and I warned him that naughty little boys get spanked. He treated that as a joke. "You're the one that's going to get spanked, boy. And then fucked!" he boasted loudly.
"You had best behave, Russ, or you will be sorry." I warned him.
I let him go on for a bit and then I struck. Unlike Kris, I'm stronger than Russ so I started the lesson. I grabbed his arm and seconds later I had him in a painful hammerlock and pressed to the wall. He was screaming. I told him to be quiet and gave him an incentive with a bit more pressure. He got the message and shut up.
"Russ, please unbutton your shirt and jeans for me." He hesitated but complied. "Kick off your sneakers, now, please." Again he obeyed. "That's my good little boy."
I backed off a bit and made him lose his clothes. He was cowed enough not to try anything funny and certainly confused. Once he was naked while I was still clothed, he was more subdued. It certainly helped that he knew that he was definitely not in control.
I led him into the hall and sat on the study, straight-backed, side chair and pulled him over my lap. "Please, don't spank me, Kris, please." he begged. I answered him with a barrage of hard spanks on his most deserving bottom. I was not gentle and it had the desired effect – his ass turned deep red, very hot and he was crying. I made sure he would remember by generously giving him some extra spanks.
When I stopped spanking, I got him on the floor between my feet and let him cry with his head on my lap for a few minutes. "Open my pants, boy." I commanded. He obeyed and my hard rod popped out from its bushy home to his amazement. I did not let him think about it but set him to suck it instead. I kept a good grip on his head so he knew I was totally in control. He gagged a few times but that was also good. He got my first load with much of it blasted down his gullet. The rest filled his mouth and I warned him not to do anything but to swallow it. Not surprisingly he did.
Certainly by now he knew I was not the wuss he had thought. I parked him in the corner with his hands on his head and told him to think about how he should be a good boy and not to make a sound. I can't be sure what he was thinking but he did not move or speak. I reinforced the lesson by having him write two hundred times: "I must be a good little boy and obey my parents, teachers and SITTER."
About an hour after the first spanking, I took the humbled crybaby upstairs for his next lesson. This time I stripped as he waited in the corner of his own room. I prepared a few things for later and then called him from the corner. He was afraid to get over my lap again but I told him he would not like it if I had to force him. Whimpering he complied. I gave him another spanking and he quickly got to the bawling stage like I wanted him.
I put him on his back and got his legs on my shoulders so that I could watch as I fucked him. He begged me not too, but I reminded him that he had not heeded my pleas in the past. He was crying as I lubed up his butt hole and positioned my hard cock. I was the irresistible force as I pressed into him. Then I began a long slow fucking. I wanted it to last. Just as I expected, my banging away at his prostate made him get erect. He had fear in his eyes but his erection did not falter and I fucked the cum out of him before I exploded blasting my cum deep into his guts.
I adjusted our positions for the next act. I got my knees forward and his legs about my side with my cock still up his boyhole. "You are too immature to have pubes, little boy." I said as I began to clip them short with my scissors. "P…l…e…a…s…e." he begged but I did not even pause.
When I sprayed the shaving cream on, he was passed begging and crying. I soon had him baby smooth. There was defeat in his eyes along with the fear.
He chose to eat standing up and was very respectful. I had him stand in the corner for an hour before I took him back upstairs. He did not like that I gave him a bath rather than letting him shower but that was part of the treatment. I watched him brush his teeth and pee before putting him into bed naked. He wanted his pj's so he had to admit that he had lied about not wearing them.
I told him several things as I tucked my little boy in for the night. First, that he should look up the Golden Rule before he was nasty to anyone else. Second, he had another spanking coming for his past behavior and could expect it next time. Third and finally, I wished him pleasant dreams.
I was sure that Kris would not have any trouble with Russ after tonight.
* * * * * * * * * *
I sure had trouble getting to sleep after Kris spanked, fucked, shaved and bathed me. I did not like it at all. Just like he can't tell, neither can I. I sure do understand the Golden Rule thing a lot better now. I treated him nasty. He turned around and did it back to me even worse. I guess that why they say turnabout is fair play.
I'm sure not looking forward to another spanking. I hope I can talk him out of it.
* * * * * * * * * *
It was most exhilarating to hear Kroy tell how he dealt with that insolent brat Russ. I hope that the boy has truly learnt his lessons for I'm not sure that I could do what Kory did while impersonating me. Kory decided that I must practice being in charge so he been giving me lessons.
The big thing is to feel that I can do it especially with the little whippersnapper. It's all one's attitude. The other thing is that I had to practice was spanking. Kory generously volunteered to be the spankee and I practiced eight times with him and it has gotten easier.
It actually helped to think of one of my first books. With Kory over my lap, I spanked him thinking: «I–think–I–can, I–think–I–can…» and, like that tough little engine, I could.
Well, the showdown was this evening and it was great. Russ was a very polite and quiet boy as he was obviously worried about what might happen. He showed me that he had done his homework before asking permission to watch some TV. He even promised to be a very good boy so that I would not have cause to spank him. He also begged me not to give him the promised spanked as he had already learnt his lesson.
"Please drop your pants and get over my lap, Russell." I said calmly. He sniffled but obeyed. He looked a lot more boyish without any pubes. Once he was in position, I patted his butt a few times and then asked if he was going to remain a good boy.
He immediately promised the world and more.
"I'll make a deal with you, Russ. You remain a good boy and keep your pubes shaved then I won't spank you." I punctuated it with a gentle spank.
He hesitated and said: "Deal." I quickly let him up and he immediately pulled up his pants, we shook hands on it.
He been good ever since and it has been six months. I'm getting pubes now and he been asking if he may stop shaving. I'm going to say yes shortly.
© Copyright A.I.L. January 7, 2013
The URL for this page is: https://yleecoyote.asslr.org/HandCookieJar.html
Last updated: September 15, 2023