This is fiction. It is a Cinder-fella story about boy who would trade place with Cinderella as it would be a step up. There are scenes of spanking, shaving and sex among various teens. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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My sister is five years older than I am and has always been aggressive and tough like a tomboy even while still being feminine. We were half of the typical family until father died when I was seven. After that mother had to take a job working the swing shift which meant that my sister effectively had a job also: caring for me, her kid brother, after school – a babysitter or more to the fact a substitute mom.
Our parents also believed in spanking us. You know: "Spare the rod and spoil the child." The punishment procedure was quite formal to the point of being a ritual. Both parents would do it the same way. First, the errant kid would "discuss", i.e., be lectured, about the misconduct. Second, he (or she) would be sent to his room to think about it. Third, he would return naked to the parent, ask forgiveness and, four, be spanked OTK. Finally, he was required to stand in the corner, still naked, for some time exhibiting the red butt. When I was little I wasn't modest and frequently ran about naked. But it was very different when as part of this discipline procedure I had to be naked and fully exposed to all. That is what I most hated about this regimen. I once got to see my sister this way and she was very embarrassed. She told me that I better make myself very scarce the next time or else; her message was very clear. Several times my sister's friends just happened to be visiting when I was being punished and they took great delight in my humiliation and embarrassment. In retrospect, I think that mom liked this to happen and even encouraged (planned?) it. By the time my sister was thirteen, mom allowed her to wear a nightgown if I was around. I was always required to be naked even (particularly?) if my sister and her friends were around.
About six months after dad died, one evening I did something naughty or bad; I don't even remember exactly what, but it rated a spanking if mom found out. I knew it and, worse, so did my big sister. She gave me a choice (of sorts). I could take a spanking from her immediately as per the described script or wait for Saturday morning for mom to do it. To help me make a decision, she told me she expected that two of her friends would be visiting then and she was sure that they would enjoy the show. I accepted her offer and she began the ritual. A half hour later I returned, naked and for the spanking that I had earned. She promptly obliged by putting me over her lap. She hit as hard as mom did and in a few minutes I was crying like a seven year old should when spanked. While doing my corner time, my solace was that her friends wouldn't see me naked and getting spanked nor would I have to dread the weekend. Also, my sister would see me naked and embarrassed regardless of which option I choose.
In her role as substitute mom my sister completely rescinded the even little privacy that a kid usually has. Not only did she check my homework she also very intimately (intrusively!) supervised my baths, toilet use and dressing. Even when she did not actually give me a bath, she never allowed me to close the bathroom door or, even, the bedroom door. Being naked and eliminating with my sister watching became as natural for me as it does for a pet dog. If I was sick, she would act the nurse and meticulously take my temperature rectally, of course, very frequently because she knew I hated it. She took even greater pleasure in solving another problem – constipation. I would have to wait naked on the bed while she filled the enema bag and brought, dangling on the IV stand, it to my room. She did it two ways. Sometimes I would lie prone and she would spread my checks while other times she would have me on my back and make me lift my legs. In either case she would then put some grease on and into my butt hole handling me as much as she could. After she pulled her finger out she would shove the nozzle in (ouch) and hold me in place until the bag emptied and then for another agonizing ten minutes. Then I would run to the toilet and let it out along with every else, when she permitted me.
By the time I was ten or eleven, I really tried to get some privacy but I was trapped. Between "Don't be shy; it isn't any different from what I saw last week." and "Do you want mom to know about whatever." she kept her control of me. Her best friends even became part of this for sometime while I was doing my meditating before a spanking she would invite her friend over to watch the rest of the show. She even videoed it a couple of times so that they had tapes of me naked and being spanked. Once they even taped me when she was giving me an enema. "How would you like your friends to see that?" she asked. I was virtually her slave after that. The job mom had kept her tired much of the time so she never considered why I minded my sister so well and never, ever was the pesky little brat that kid brothers are expected to be. She just enjoyed the peace and quiet. Correspondingly, my sister enjoyed dominating me and she could always maintain control.
My sister was always physically bigger and stronger then I was which made it harder to resist even as I got older. She even devised a tickling torture game. She would tickle me and if I could keep from yelling for a minute then I would be free of the game for at least two days. If not, I had to stop resisting and yield to her mis-handling (pun intended) of me. I usually ended up naked and frequently spanked (although gently). I really hated this game and just the threat of if made me very responsive to her wishes. There was a complication to this game. Excessive tickling would make me lose control and pee in my pants. This got me a spanking and put into a diaper for the night. In order to avoid this fate, particularly if any of her friends were there, I would stop resisting very soon and assume the spread-eagle yield position if I felt that I might pee in the hope that she would be kinder. She loved to get me naked and embarrassed before her friends.
It wasn't just her girlfriends that she showed me off to but also to her boyfriends. Instead of watching a tape or TV they would play with me not a playmate but as a toy. Her favorite game was house. I was a naughty boy and would have to be spanked. Most of the guys liked the game for they blamed me for not being somewhere else with my sister. Others pretended that I was their own nuisance of a kid brother or that they had turned the tables on their dominating older brothers and really tanned my butt. One thing that they had in common was that they all got very hard erections that I could feel through their pants while I was across their laps. Once on a night that I had been put in a diaper, my sister and her boyfriend came and woke me up. They tickled me hard and long until I both cried and wet my diaper. I was required to stay wet until morning.
When I was just I little into puberty and just getting some pubic hairs I messed up late one Saturday afternoon. After morn had lectured me she said if she wasn't so tried that she would spank me. My big sister then volunteered to do it. After finding out how much my sister had been doing her job and, in particular, that she had been spanking me for literally half my life, mom ordered me to go to my room to get ready. I protested that I was grown up and even had pubic hair. "Don't worry about it son," she said "that's not a problem at all." Mom then told sis to take me to the bathroom and shave my crotch so that I wouldn't be embarrassed mistakenly thinking that I was a man when I was being spanked over her knee. I tried to protest because of what the guys would say in the school shower but mom wouldn't hear anything. As sis dragged me to the bathroom, I pleaded with her not to shave me but just to spank me. "No way, boy" she said, "we're going to do just what morn said. I sure it will be fun; lots and lots of fun." Then she added "If you resist I'll get my boyfriend, Chuck to help." I went compliantly after that. Chuck was a big hunk who did not like me and sis did not make idle threats. As he already told me that my butt was even cuter than my sister's, there was even the additional possibility that he would then fuck me in front of my sister.
While I stripped and got into the bath tub, she set up the camcorder to tape this event. I knew that I was totally impotent in this situation. So impotent about what was happening that my usual semi-hard to hard teen cock was as soft as could be. After ordering me to keep my hands behind my back sis wet my crotch down with warm water from the shower hose and covered my pubes with shaving cream. Then with a fresh sharp blade in the razor she removed the beginnings of my small bush as I watched with consternation. After rinsing me off she dried me and sent me to my room to contemplate my upcoming spanking. A half hour latter as she put me over her knee Mom was watching and encouraged her to make me really feel it. Then as I stood in the corner with my red butt hanging out, mom told sis that she wanted her to take charge of me full time – officially. She then told how she had kept dad shaved for years and that made him much easier to manage. Mom also counseled that I be kept hairless for a while so that I would remember that I was still just a boy. Sis said that sounded like a great idea and mused that least six months would be needed – at a minimum. She shaved me once a week to keep me hairless for the rest of the term and through the summer vacation. She sometimes had her best friend help her to show how she still controlled me.
When school restarted in the fall I was starting my junior year and I begged her to let me have hair for school like almost all my classmates. With more than her usual glee she shaved me extra close the night before school reopened and then told me I would have a choice the next week. The first option was that she would continue shave me every week and my classmates would just think that I was late in getting hair. The second was that she wouldn't shave me unless I earned three spankings in any five week period and then I would have the fun of explaining why I suddenly had bald pubes to my presumably hairy-crotch classmates. I knew that she would certainly be able to find reasons to spank me that often and thus shave me again in mid-term. So the next week when she asked for my decision; I did not have one, but just begged her again to be kind and merciful. "Very well" she declared "as you can not make a decision you are obviously still a just boy, therefore you must continue look like a boy." I was already naked as per her instructions as she led me into the bathroom where she covered my crotch with a depilatory. In a few minutes I showered to wash the cream off and I was as smooth as a baby. She then made me "tinkle", rubbed some body lotion on my pubic area and put me to bed like a little boy. She even gave me my old teddy bear. I cried myself to sleep as I then realized that I was going to be her little boy for a long time. I expected then that it would be likely that I would be the only one with smooth pubes in my graduating class because she wished it and has the power to do it.
At winter recess mom unexpectedly had to go to visit her sick sister and my sister had previously made plans to stay with Chuck. As I couldn't stay alone it was decided that I would go with my sister. Chuck's brother, Terry, was two years younger than me and we could kept each other amused. Terry was like his older brother – big, strong and aggressive. The night before we went, my sister shaved me and told me that I had better listen to what I'm told or she would spank me – bare-assed – before Chuck and Terry. Also, since I was a guest, I should do as my host, Terry, wanted. This last instruction was not at all required as Terry immediately established his dominance over me with amazing ease. With a bit of supposed playful wresting Terry showed me that he could control me totally. In just two minutes I was flat on my back with him on my chest. He saw that I was looking at his hard cock straining at his jeans. "Now we all know who's top dog." he said and I nodded submissively.
Latter when we were getting ready for bed, I showered first and put on a fresh pair of briefs. When he came out he was nude with his fully mature equipment already half hard and sporting a full bush before he was even thirteen. He ordered me to strip for him and then made me turn around so that he could inspect me. After years of directions from my sister, I was conditioned to follow such orders particularly knowing that he could easily force me to do as he desired. "Chuck was right; you do have a very cute butt and you been shaved." he stated very frankly after feeling my pubes. As he pulled down the covers on the bed for action, he asked: "Do you like – to suck first or get fucked first?"
"I don't do either" I said in my most masculine voice.
He just laughed. "If you don't do as I say then you're not a good little boy and I'm going to spank you; so what will it be?" When I didn't respond. He grabbed me, sat down on the bed and pulled me into spanking position. As his hand reddened my ass I could feel his cock get very hard. The spanking, of course, put me into a extremely docile and submissive state.
After a few minutes he just pushed me down on the bed and sat on my chest like he had earlier in the day but now he was playing with his already hard man-tool. I shook my head no and he said: "You're goin' to; will it be the easy way or the hard way?" he asked taking my balls in his strong grip. I got the message and opened my mouth as he leaned forward. I was sucking my first cock because a ninth grader had told me to. As I was being used I somehow felt good although I did not understand why. After a few minutes he shot his load and kept in me until I swallowed it all. Still hard, he moved between my legs and lifted them up exposing my ass hole to his still rampant cock. (This was like my sister giving me an enema.)
"Please be gentle; it's my first time, Terry." I pleaded. He smiled as he pressed forward and my hole yielded to his hard man cock first the first time. Occasionally I had jerked off, but this was really different as he rubbed against my prostate. I came before he did, shooting a mess of come over my own chest. He gave a mighty roar has he came in me for the second time in just a few minutes.
Suddenly I heard Chuck saying: "Congratulations, Terry, you won the bet by getting both his cherries in less than a half hour." I looked and saw both Chuck and my sister standing there.
"Would you like sloppy seconds, brother?" he asked Chuck.
"Not tonight; I have something much better."
As she left my sister said: "Have fun, boys." Predictably, he was always in control and refused even to play with my dick. He called it "a baby's little hairless pee-pee" and told me that I was a pussy-whipped sissy. All that night he constantly used one end or the other of me. I learnt how to suck his cock and balls to please him and even to rim him. Once when I tried to refuse, he just turned me over and gave me a few very hard slaps on my ass to remind me of my subservient role. After that I did what ever he wanted immediately like an obedient little boy.
In the morning when he decided he wanted to get up, he announced that this would be the last fuck of the night. He had me prone and was on top of me. He took his time and made it last. After he came he told me to keep still and held me down (not that I could go anywhere). Then I realized that my gut started to feel full and recognized the sensation; it felt like an enema. He was pissing in me.
When I returned from my shower, I looked for my bag. It did not have my clothes in it but a girl's dress and panties. My jeans and other clothes were nowhere to be found. Terry was not helpful at all. He even said that the dress in the bag was "a nice little girls' dress and that I would look very pretty in it." Then he added: "Wear what you brought or nothing but don't take anything of mine; I don't want a sissy boy (or is it girl) in my clothes." He dressed quickly going off to breakfast and left me alone with my dilemma.
Of course my sister had done this for she wanted me in that dress, but what should I do? I almost went out naked but imagined that my sister would immediately order me back to put on the dress. Then I would end up both being ordered publicly to wear the dress and wearing it. I chose to put it on. It was very short so I also added the frilly pink panties that were also in my bag to cover my crotch both fore and aft. They were all waiting for me downstairs. Chuck laughed, Terry wolf-whistled and my sister said that I looked very pretty in the dress. Over breakfast, Terry told how he used me all night and again offered me to his brother. Chuck said that he had the real thing but just for the fun of it, later. He also said to my sister that she was right predicting that I would NOT have the guts to come down naked or in a towel, to look for my clothes or to use Terry's. She continued that we should keep him in the dress all week since he put it on by his own free will. To insure this Terry took my clothes which were just on the sideboard and locked them in a cabinet.
I was very embarrassed and ashamed. Now I also knew that I had really made the wrong choice by putting on the dress and I had a premonition that it would haunt me for a long time. They had tested me and I had failed ignobly. Like with the shaving decision at the beginning of the term I couldn't make a decision like man; I was still just a little boy like my sister said. They all thought that it was great fun having me go to the door when the supper delivery came. I'm sure that guy really stared at me since they wet my panties so that they were almost transparent. That night was pretty good for I liked the way Terry's cock fit into my holes.
At noon the next day, my sister told Terry that the time was up and he had lost his bet. The stakes had been high: if Terry won he had to right to fuck and shave my sister but if he lost she would shave him while his brother fucked him. And it had all been up to me – all I had to do was to show some spunk just once by asserting myself and Terry would have won. "A man does not welsh on his bets." he declared and he went upstairs. He returned a few minutes later naked. He gave his brother some lube and my sister a hair clipper and shaving stuff. We all went into the family room where Terry got down on all-fours. His brother greased up his ass hole and his own ridged tool and entered his kid brother doggy style. After a few minutes my sister told them to stop and they changed positions. Chuck was sitting with Terry, still impaled on his rod, on his lap with his pubes all exposed. My sister was over joyed as she carefully used the clippers reducing Terry's thick pubic forest to clear-cut stubble. Then she covered the area with shaving cream and made him smooth like a little boy. His hard cock seamed even bigger without the base being obscured by his big bush.
They resumed the doggy position and my sister ordered me to suck him as his brother fucked him. Then she announced that since Terry had been so courageous about this he deserved a reward. She slipped off her panties and allowed Terry to lick her pussy. When they had finished, Chuck told Terry that he was proud of how he lived up to his bargains even when it was unpleasant. "Hey, sissy wimp lie down here on the floor" Terry ordered and then sat on my face. "Eat out my ass hole, sissy." he commanded further. His brother's come was very good.
That night there was an envelope from my sister on Terry's bed containing two cards. The first done like a business ad was for "A FREE Shave by the Mistress". The second was a little note giving Terry full authority over me as long as my sister had control along with a recommendation that I needed a good spanking. The first card was useless but, as we went to the same school, he appreciated the second one: "It will be real nice having a junior to do my bidding at school and to fuck every afternoon. I wouldn't be able to find a girl that frequently and they require lots of attention. I was appalled for it now meant that I would have to submit to him all the time particularly at school.
After removing the dress, but not the panties, I knelt before my young master and took his hard cock into my mouth. I noted that without hair, he looked even bigger than the previous time. Later I asked him what he was going to do in the school shower to explained the hair loss. "No problem," he confidently replied, "I'll just say I did it to win a hundred dollar bet." He then explained that "I've been lusting for your sister for months and this was the only possible chance I had to get her. Besides I did get to go down on her and rights to you, pussy boy, forever – and you're a good fuck. By the way, I like you smooth and I'll shave you if your sister doesn't. I think you'll like being my boy."
He was right, I did like the idea very much. Then I got very bold (at least for me) and asked "But as your boy, I shouldn't wear a dress. Please let me have my pants back, Teddy."
"What will you give me?" I thought a bit, but realized that I did not have anything to bargain with since he already had me and told him so. He then said no dress but the girl's panties for three weeks. We settled on two weeks total but not pink or with lace after school started. "Enough of this chatter, boy, start sucking my rod."
This was the start. From that day one Terry and I saw a lot of each other. On most days he came over after school and we fucked and sucked. He kept me hairless as he promised and I was definitely his obedient pussy boy. In some ways he was even stricter than my sister and was always in control. I was never allowed to see any one else. My sister also insisted that I do more and more about the house so I even became a proficient housekeeper.
During this time, Chuck and my sister broke up. She found another guy who was even more submissive than I and took control of him. Within the first week, she gave the guy a full shave and told him that he had to do it himself every day from then on. She turned him into a maid and sometimes she would have some friends over who also had maids for a party. Once she had to take a trip but he had to remain so she put him under lock and key literally with the help of her best friend. He was stripped and forced to soak his cock and balls in ice water until they were practically frozen. Then without warning him, she grabbed his sniveled numb cock pulled the foreskin forward and punched two sets of holes through it using a leather punch. She plunged it back into the ice water and the bleeding soon stopped. Then she slipped a small lock through the holes and snapped it shut. She had infibulated him! Even after she returned from her trip the lock remained in place. Periodically she would remove it, so that he could clean under the foreskin. He was definitely hers.
Terry did find a girlfriend later that year. They enjoyed coming over to my house where they could fuck and both be served by me. Most of the time, however, Terry came over by himself. I liked that better; much better.
© Copyright A.I.L., March 18, 1999
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