The following story is totally fiction.  It contains scenes of spanking , shaving, w/s and sex in a man/teen/pseudo-boy setting.

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 email.

Click to have ​Metric units​ (​American/English units​) used in the story.

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Penitant Boy

By

YLeeCoyote@juno.com

TUESDAY:

I fucked up at work – royally.

WEDNESDAY:

The boss had a little talk with me.  It was just like Dad's lectures after I had brought home one of those little notes from the school's vice-principal.  I felt bad about it but didn't really hurt.

TUESDAY:© YLeeCoyote

In the give away weekly paper personals was the ad:

I called, left a confession of my misdeeds and that I was feeling like a naughty school boy in need of a, er, er, discussion with uncle since dad was away.

FRIDAY:

When I got home, there was one message on my answering machine.  In the same commanding voice that was in his voice mail greeting I heard: "Boy, I got a letter from your school principal and I'm very disappointed.  We need to have a serious man to boy talk right away.  Call Uncle Sam immediately at: OTK-SPANK."

Of course, I called without delay.  He took immediate and total control of the conversation.  He was so charismatic that I quickly told him everything about me that he asked (and more) and agreed to report him immediately for the discipline that we both knew I needed.  I showered, shaved (my face) very close and dressed like a high school kid, even wearing my old hometown high school jacket.  On the way over to his house, I stopped at a store for a pair of white briefs two sizes small and put them on in the store's men's room.  These held my genitals very tightly, minimizing my small basket, which underscored my boyish appearance in my tight jeans.  Just an hour after the call, I was at his door dressed precisely as he had ordered.  When Uncle Sam opened the door, I saw that he was exactly like his voice mail had stated: a fatherly looking man.  He was a big man, at least ​6′8″​ (​203 cm​), and since I'm only ​5′2″​ (​157 cm​) I really felt Lilliputian and like a pre-teenaged kid.  He lead me to the basement family room which looked like it was used and that he really had some kids; it felt like home.  We sat on the couch and he began the lecture: "I spoke with your principal and he told me that three of your teachers have complained of your sassiness and neglect of your homework. Is this true, lad?"  I turned away while making incoherent noises but he did not let me get away that easily.  "Look at me, boy" he ordered sternly and repeated the question: "IS THIS TRUE, BOY?".

As he started into my eyes, I felt compelled to admit my failings: "Yes, it is true, Sir.  I have been naughty, Sir." I blurted out with some strange feeling of relief in a meek boyish voice.

"Then you must be punished so that you will be a better boy in the future.  Take off your cap, jacket and sneakers." he ordered.  After I had done so he summoned me over with a beckoning hand and I was standing before him in just a T-shirt, jeans and sox.

Wordlessly, he reached for my jeans, opened them and pulled them down to my ankles.  I immediately recalled the only time that dad did this to me.  Although I was pre-puberty and we were alone I was terribly embarrassed and ashamed.  Now, even though I am on my own, I again felt exactly that same way.  I started to relive that experience.  I knew that I was certainly blushing and it even seemed that my penis was shrinking.  I'm also certain that Uncle Sam could tell for I was wearing the extremely tight new briefs and my crotch was but two feet from his face.  I wanted to move; to run away but I was paralyzed and couldn't even blink.  Also, now that the spanking was so imminent, my fear of that increased although I knew that then my shriveled little thing would be hidden.

"You know that you deserve this spanking, boy?" he asked gently.  I nodded a bit and he pulled me over his knee and held me in place.  At his first touch I could feel how much stronger than I he was.  I knew that now that I was under his control.  There was no turning back.  I had past the point of no return.  Now I would experience the real spanking that I needed.  Then my guilt would be assuaged and I would go on with other things.  He began gently; relatively gently but still it hurt.  I yelled at the first stroke which had surely left a hand print on my butt.  It didn't take long before I was throbbing and feeling like a helpless boy getting a well deserved spanking at his father's will.  He lifted me up and I though it was over but I was never so wrong.  My briefs then quickly joined my jeans about my ankles and my T-shirt seemed to evaporate.  Then I was pulled back so he could continue the OTK spanking – now on my bare butt.  Soon I was really crying just like a little boy; just like I cried when dad spanked me long ago.  I was no longer a man of twenty-four for I had been transformed back to be a boy of twelve years!  Although I did not know it at this time this marked my rebirth as a boy.  Uncle Sam was the doctor who had pulled from me from the womb and got me to take my first breath by slapping my bottom.  I was begging him to stop and promising to be a good boy, a very good boy, really, really truly, Sir.  My ass was on fire when he finally stopped and stood me up.  I could hardly stand as he asked if his little boy had learned his lesson.  I nodded and in a meek, weak little boy voice mumbled: "Yes, Uncle Sam."

I was perplexed.  When I fantasized about being spanked, my cock is always rock hard but now it was not.  As I stood with my head down sobbing, I felt just like a little boy even though inside I was very eroticized.  As I saw my little penis, I felt puzzled at why a little boy such as myself had hair down there.  It didn't feel right somehow.  Was I a freak?  I was in a reverie in my own private universe trying to sort it out.  Then a hand entered into that universe; it took hold of my little sex organs and then a second hand materialized.  This one was holding a barber's hair clipper and proceeded to remove the unseemly hair.  Inside my head the little boy was cheering the correction of something improper while the young man was outraged at being stripped of an external sign of manhood without warning much less consent.  The latter made some protesting sounds (almost words) but Uncle Sam commanded silence and so the little boy sighed with relief while the young man sighed in resignation as they both slipped back into their private universe.  When the chipper had removed all the pubic hair that it could, it moved up and repeated the operation in the armpits.  In the wall mirror I could see that from afar I appeared just like a boy as I didn't have any body hair not even the tiniest of a pubic bush.

Uncle Sam just picked me up and carried me to a table at the other end of the room.  He sat me down and removed my socks, jeans and briefs.  I was now completely naked.  The table was by a sink and he proceeded to shave my entire crotch while standing between my legs and then repeated the process on my ass.  He used a hot towel, hot lather and a straight razor like I had seen the barber do when he shaved the big men in his shop.  The hot lather felt really good as he continued to transform me into a little boy.  When he had finished, he washed me and I was baby ass smooth both front and back.  He dried and powered me and then he made me stand in the corner while he had dinner and watched TV.

In the dark of the corner I stood for a long time.  I rubbed my red hot butt in a futile effort to reduce the pain but it did not help.  I had deserved a really hard spanking.  I had gotten a really hard spanking.  This had traded the mental anguish I had for a less complex physical pain (that would fade with time).  I was also enthralled by my hairless pubes which I was looking at while I stroked them.  The world seemed simpler now that I was only a little boy again.  I had been naughty.  Now I was being punished and then it would be over.  Since I had been in high school, the other guys had taunted me about my small penis, even referring to it as a mere pee-pee.  Now, hairless again and feeling like a boy, it felt right just having a little boy's pee-pee rather than a big man-sized cock.  I guess that's why it wasn't hard before; I was only a little, impotent boy.

Uncle Sam put off the TV, called me over and asked how I felt.  "My bottom hurts.  It hurts a lot,  Uncle." I replied with boyish simplicity while standing naked before him.

"I'm sure it does, boy; it's supposed to so that you will learn to behave properly.  And now it's time for little boys to go bed." he said.  Taking me by the hand he lead me to the bathroom, watched while I tinkled (at his command) and tucked me into a small bed in a boy's bedroom.

"I'm hungry, Uncle Sam," I whined.

"Of course, boy," he replied, "you were standing in the corner during supper so you missed it.  You should know that naughty boys always get sent to bed without dinner."  Even though my bottom was red hot and hurting, I soon drifted off to sleep (lying on my tummy) as a little boy should having been tucked in safely in his bed by his uncle.

SATURDAY:

After breakfast Saturday morning he did some work about the house while I was required to do boys' chores such as raking the lawn and taking out the garbage.  In the afternoon we went to the park and happened to meet one of this friends and Jason, his son.  Although Jason was only a high school junior he was already on the varsity football team.  I was introduced as a visiting cousin who was just in junior high school.  Since I am so short it all appeared consistent.  We all played together for a while and then had takeout at Uncle Sam's house for dinner.

Jason and I were sent off to play together while the grownups talked.  I was too embarrassed to let Jason and his dad know that I was twenty-four so I continued with the charade.  In my fantasies I never expected to regress like this but it did feel so right to do.  Taking a break from the video game we were playing, I went to pee.  Jason quickly followed and we crossed our yellow swords.  (His sword won the duel.)  He had a really big and hairy cock and as soon as he stopped peeing it got fully hard.  I couldn't take my eyes off of it and Jason saw that I was staring.  Of course, he saw my little pee-pee and asked if I had hair yet.  (Remember, he thought I was thirteen at the most.)  Before I could answer, he pulled at my jeans opening the top button and swiftly de-pants and de-briefed me.  "Don't worry, when you get hair it will grow like mine did" he said kindly but also proudly flaunting his own mature development.  "Let me show you."  And he dropped his own pants and briefs.  Not only did he have a big (now hard and rampant) cock but a matching set of balls with a big thick bush.  I ogled this young man's tool even harder than before for I knew my little tool would never be any bigger than it was now.

Taking full control he led me back into my bedroom and sat on the bed.  Then he pulled my head down forcing me to my knees between his legs.  By staring so hard, I had told him that I was interested so he didn't need to ask if I wanted it.  Lusting, I parted my lips and his cock went deep into my mouth as he pulled me to it.  This young stud was delicious.  He didn't really let me suck him, but held my head and face fucked me.  In just a few short minutes, as he rammed his tool deep into my gullet, he blasted his load even deeper.  He let go of my head and I sucked and nursed on his wonderful potent shaft trying to suck him dry.  As I did this I was also playing with my own little pecker which was as harder and bigger then it ever had been previously but still tiny in comparison with his monster.  Jason was encouraging and directing me all the time.  His young body was constantly producing lots of delicious pre-come but suddenly he stopped me, told me to wait a minute and went into the bathroom.  He was back in a minute and had me kneel with my chest on the bed.  While he held me down with one hand, he applied some cream to my butt hole with the other.  Without any delay, he started to finger fuck me.  First with one finger but, with the impulsiveness of youth, was soon up to three and I was moaning with pleasure.  He removed his fingers and quickly pressed his cock to my fuck hole.  I pushed back as if I was a bitch in heat.  With each stroke he drove his shaft deeper into me until I felt his bush rubbing up against my hairless crack.  Then he started pumping away with great enthusiasm.  Each and every thrust rammed his shaft across my prostate and drove me wild.  If he hadn't pushed my face into the bed, my yells of pleasure would have surely roused the neighborhood.  He roared when he came which drove me over and I shot into the side of the bed.  He had me lick his cock and balls until his dad called that it was time to go.  I was terrible envious of how dominant this youth was and knew that I could never resist him nor even emulate him.

We fixed up our clothes and went downstairs with me walking just a little bit funny.  In the living room Jason was standing behind me holding me.  "Did you kids have fun?" asked Jason's dad.  I just nodded my head, Jason happily announced: "Great, Dad; he is a fantastic fuck with a really tight ass!"  While I was doing my beet impersonation, Uncle Sam said that he was really glad that you kids had fun.  Jason and his dad left leaving me with Uncle Sam.

I felt very different that next week.  I could not forget that Uncle Sam had shaved me and Jason had taken me.  They both had made decisions for me and I realized that I loved being under their control.  Uncle Sam had decided that I should be a hairless as a boy.  It seems that I was constantly reminded of the fact; in the shower, when dressing and, of course, in bed.  Even during the day for when I urinated and reached into my pants for my penis I would feel my smooth pubis and then find only the little pee-pee of a boy.

He also checked up on me every evening to make sure that I was a good boy.  We were the only ones to know of my double existence.

TUESDAY:

After Uncle's checkup call in the evening, I felt that I had to go out.  I went to the neighborhood bar, stayed out too late (not even having fun) and consequentially was late for work the next morning.

FRIDAY:

It was just my luck that the boss was in a bad mood that day and I was ordered to report to his office at the end of the day.  He was on a marathon call and so by the time I got to see him everyone else had gone for the weekend as it was well past quitting time.

He lectured me on my irresponsible behavior and I let it slip that I had stayed out late the previous night at a bar.  That really cooked my goose for his next words were that naughty boys need to be spanked and that my Uncle Sam had given him permission to do so whenever I required it.  I was dumbfounded for I thought that my boy status was a secret.  As I stood in shock he sat down on the office couch and ordered: "COME HERE, BOY!"  I meekly obeyed and he took my pants and briefs down to my ankles.  He felt my crotch and pooh-poohed saying: "All too often as soon as a boy starts to get a little hair he starts to think that he's a man and gets wild."  It was true; I was being to get a little stubble on my boy pubes.  Then he pulled me over his knee and commenced spanking me.

I was not prepared for what happened.  I expected a hand but he had a leather paddle and he hit hard.  He was not as strong as Uncle Sam but the paddle more than made up for it.  Very quickly I was bawling like a baby and begging him to stop.  And eventually he did.  Then, with my burning red ass upper most in my thoughts, he rubbed some cream all over my stubbly pubes.  While I stood there sobbing, he selected a piece of paper from his desk, sealed it in an envelope and then said: "O.K., boy, pull up your pants and you to go directly home.  Here are your orders; open them at home." he said and handed me that sealed envelope.  Wiping the tears from my face, obediently I did as he had ordained.

On the bus home, I stood while constantly looking at the envelope inscribed in large bold letters: NAUGHTY BOY'S ORDERS.  Once at home I immediately opened the envelope.  It contained one sheet of paper with the same heading as the envelope and the following terse instructions:

My burning butt reminded me that I must obey and I stripped down.  My crotch was also feeling strange so I took my shower.  As soon as I rinsed off, I realized that the boss' cream was a depilatory as my crotch was now smoother then when it had just been shaved.  Dutifully, I set the timer and started to do my corner time.  Just like last time, my hot ass, hairless pubes, and obedience convinced me that I was a boy again.  Even my job title confirmed it: Office Boy!  And since my boss knew, there wasn't any getting away from it.  The timer bell ran and I went off to bed without dinner.

XXXXXDAY:

Over the next few weeks I visited Uncle Sam frequently (at least twice a week).  I knew that he was training me to be a boy, but I could not resist him.  It was like a drug that I was hooked on.  He took more and more control.  Every time he shaved or spanked me I felt more like a boy and became more docile as his control became stronger.  He was very strict and soon I had ask permission to even go to a movie and I was required to be in bed very early just like I was a schoolboy.  Work seemed like school since my boss knew what was happening and also treated me like a boy.  I knew that he had that paddle in his desk and that he could use it again.  I did not know where I was headed but I was on a happy trip.  One day my landlady told me that she had sold the house and, as the new owner did not want a tenant, I would have to move.  When I told Uncle Sam, he invited (i.e., strongly suggested) that I move into his place which I did.  His control expanded as I was with him every day and I was living the part of a boy all the time.  Somehow my few friends didn't live up to his high standards and they drifted away.  My meager pay check went directly to his bank and he kept most of it for room and board.  I got a small allowance plus lunch money and carfare on work (or should I say, school) days just like a real schoolboy.  I became very emotionally dependent upon Uncle Sam.

SATURDAY:

Uncle Sam and I had almost finished dinner one Saturday at his place when the bell rang.  It was Jason.  Over a couple of beers (I had a soda) Uncle Sam then explained that he had to go out for a few hours and that Jason would be in full charge since I was too young to leave alone.  He essentially said I needed a baby sitter.  Then, just as he was leaving, he added: "Oh; I almost forgot.  The boy has been very rambunctious today and if he gives you any trouble at all just SPANK HIM."  I nearly fainted for without warning I had just been put into the custody of a large, strong, aggressive, dominant teenaged youth like I was a real little kid.  I knew that he knew that he could control me like he did that first day and that now he had full license to do so. "Don't worry, Sam, when Dad's away or very busy I'm in charge of my OLDER brother and sister and kid brother and I've had lots of practice keeping all their bare butts red hot." Jason told Uncle Sam as he left.  I noted how they were talking adult to adult showing that Jason knew the power and authority he had.  Even just as a high school junior he was a MAN!

It did not take me long to get into trouble with Jason.  I wanted to watch a different TV program than he did and I was a (little boy) pest as I insisted on staying with him.  He finally lost patience with me and flipped me over his lap holding me in place with a hammerlock.  "You asked for this, kid" and he started to spank me through my jeans.  He did not hit very hard and I started to giggle.  "So you think that this is funny?" he said.  With that he started to hit me hard.  After a few strokes I was begging him to stop and promising, as usual, to be good.  He stopped and stood me up and again surprised me my dropping my jeans and briefs.  When he placed me back over his knee and resumed pounding my butt until I was really crying.  As he was spanking me, I could feel his cock grow very hard.  When he stopped he pushed me to the floor between his legs and opened his own jeans.  He wasn't wearing any underwear so his massive organ sprung out fully hard and so did his man scent.  With the extra excitement of his musk, I instantly dove down upon the luscious tube and started to nurse it.  "Good boy." he said stroking (petting ?) my head as he leaned back to enjoy both the blow job and the TV.  After a long time I was rewarded by a delicious load of his come.  He kept me sucking on his half hard cock as he continued to watch the TV and downed another beer.

Then suddenly he announced: "I got to pee and don't want to miss this." and held my head in his strong grip.  Seconds later he let a hot stream of piss flow out of his massive tool into my mouth and down my throat.  I had to swallow very fast in order not to choke.  "That was fun." he chortled and continued to watch the program.  I tried to get up but he would let me until I begged to go to the toilet.  "O.K." he said "but you must leave your clothes here so I can watch your cute butt."  I stripped and ran off to pee.  When I returned, he let me sit beside him at which time he checked to see if I was getting any hair.  Uncle Sam hadn't had time that day to shave my pubes and so Jason found stubble.  "Well, well! You've been shaved and you're past due for another."  He killed the TV and said: "After I kept my older brother shaved for a few months he behaved much better.  Where does Sam put you for the shaving?  I just love to shave a guy."

"Please.  Please don't." I begged but he was adamant.  I got on the table and he took the stuff from the cabinet and lathered me up.  He was about to start when he suddenly put me on the floor and covered his very hard ram in lather also.  He lifted my legs and sprayed some lather on my butt hole and started to fuck me.  When he got all the way in, he pulled me forward over his thighs with my legs to his sides.  Now I was impaled on his man-cock and my crotch was fully exposed to his razor.  As he made pass after sensuous pass with the razor returning my pubes to their natural hairless state, I saw that it was my destiny to be a hairless little boy under the strict control of strong potent men.  It all felt so good – my pubes being smooth, my butt red and tingling, and Jason's shaft deep in my fundament.  I wished it would stay this way forever.

When he was done shaving me, he proceeded to fuck me hard.  As he was already deep into me, this happened instantly.  His cock seemed even larger than that first time just two months ago.  When he was ready, he gave a few extra hard trusts and blasted his load deep into my boy-butt.  When he pulled out he ordered me to get him another beer.  Then while he drank it and watched the TV, I was kneeling before him dutifully.  First I licked him clean and then, second, I happily sucked his wonderful tool.

We were still this way when Uncle Sam returned.  Jason told Uncle Sam that "after I spanked, shaved and fucked the kid, he's been the perfect angel."  They talked adult stuff ignoring my presence except that Jason kept a hand on my head to assure I continued to attend to his cock.  He even took another piss into me as they talked.  At 10:30 Uncle Sam said: "Time for bed, boy."  I got up, said goodnight and went to bed.  For a little boy must be obedient or he gets spanked.

The End

© Copyright A.I.L. December 12, 1996

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