Lily’s Embarrassing Punishment

By Olga's Little Boy

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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It was a very strict school and she hated being there but Lily’s mother was fed up with her lying and disobedience. She just couldn’t handle her anymore and at 12 years old she only seemed to get more difficult. She had been divorced for most of Lily’s young life and it was difficult raising the willful child alone. Mrs. Hansen found a strict religious school that promised to turn difficult children around, to make them more docile and Lily needed a strict hand.

The principal, Alice Ford, assured Mrs. Hansen that Lily would learn her lesson at her school for girls. Alice, as she was known by the staff and students had already met the wayward 12 year old and looked forward to managing her discipline personally. Lily sat outside her office as she discussed matters with her mother in private.

The waiting room had a couch opposite the desk where the principal’s assistant, Ryan, sat glancing often at the pretty girl. Lily was an eyeful and Ryan enjoyed watching the young pre-teen in her short skirt and white ankle socks. Lily had platinum blonde hair pulled back into a pony tail and alabaster white skin, no doubt from her Swedish ancestry. She looked so incredibly innocent with blue eyes and an angelic but very strikingly beautiful face. She was slim but not quite skinny and a little small for her age but that just added to her very cute attractiveness. She looked more like a very pretty10 or 11 year old child.

But looks are deceiving as Ryan knew from working at a girl’s school and Lily’s admission to this strict school meant that she had some discipline in her future to his delight since he knew Alice’s ways with disobedient girls. Most of the girls learned quickly but it may take a few visits to Alice’s office and the application of some strict discipline. In the next few weeks Ryan expected to see Lily again and he felt some anticipation at the thought. He had quit college last year and while working at this school for girls had seen some pretty interesting sights and sounds.

Mrs. Hansen said goodbye to her daughter and Lily was escorted to her dorm room by Abigail, one of the older girls. There were a number of dorms and about 10 to 15 girls to a dorm. Lily had been used to her own room and now found herself in a room full of beds sharing with other girls and she certainly felt this was beneath her. Abigail had the first bed near the entrance and she led the small pre-teen to a bed somewhere near the middle of the room. Abigail had helped carry her bags and told Lily that soon she’d get used to the place. Some of the other girls soon took a dislike to the beautiful child mostly envy because she was just so pretty but Lily really didn’t do much to make friends and influence her new roommates. She was a little more than haughty, partly out of shyness in her new surroundings, and the other girls took this as an obvious conceit.

Sure enough Lily found herself back in the principal’s office just a few days after getting admitted. Someone had played a prank on their 6^th grade teacher, Ms. Lisa, and somehow Lily got blamed. Well, Ryan thought, as Lily sat opposite his desk, her skirt well above her knees and her platinum blonde hair again pulled back from her very pretty face in a ponytail, it didn’t take long to see her again. She wore slip on shoes and white ankle socks that just added to her innocent charm. He glanced at her slim pretty white legs and expected that Alice would be exposing a bit more for the dreaded paddle across her pantied bottom.

He had been called more than once to help hold a girl in place while discipline was applied and he certainly hoped he might take part in Lily’s attitude adjustment. Little did he know since Alice was feeling quite wicked this morning and wanted to make an example to put some fear into the girls. Things were getting lax and these pranks and misbehavior would have to stop.

The door opened and Alice looked out motioning Lily to come into her office. She looked the young girl over and felt a wave of sudden lust take over. She was an attractive woman in her 40’s and had never cottoned to liking men a whole lot. But the young girls in her care were close to her heart in some…well…unorthodox ways. Lily noticed the large table across from Alice’s desk and the bar hanging from the ceiling on the other side of the table looking like a chin up bar but adjustable. They seemed a little out of place in the principal’s office. She also had a couch against the opposite wall.

“Young miss you just got here days ago and already you’re up to mischief. We can do this the easy way and you’ll take your punishment with the paddle or I can get tough and really make you regret you misbehaved.”

“I didn’t do anything and I’m not taking any punishment from you or anyone else,” said Lily with a defiant tone that angered the principal.

“Missy you’ll step over to the punishment bar, indicating the “chin up” bar, behind you and grab it tightly while you get paddled a good 10 strokes or you’ll end up regretting this day,” said Alice, who already had a quite humiliating experience planned for the pretty girl if she continued to disobey and she hoped the girl remained defiant as she licked her lips in expectation, almost knowing for sure that Lily would continue her insulting defiance.

“I will not do that and you can’t make me.” Lily was her own worst enemy in her defiant, arrogant attitude, more so than other girls and Alice was looking forward to taming the young pre-teen princess. Alice stalked out of her office leaving the pretty girl bewildered but not for long. When the door opened Alice was back with Ryan and two other young men, the janitor, Harper and a male teacher, Logan. Logan loved his job and he looked forward to these little punishment sessions knowing that Alice could take such examples quite far.

Harper had also helped to hold down a recalcitrant girl for punishment and his eyes went wide when he saw such a beautiful young girl who looked about 10 or 11 maybe 12 at most he figured. The last time he held down a real cutie with her short skirt pulled up exposing her panty while Alice applied some really wicked smacks with the paddle. But Lily was really very pretty he noticed and he hoped for at least the same pulling up of her skirt and watching as the paddle came down across the young girl’s buttocks with nothing more than thin cotton panty to soften the blow. Last time it was just him but with Ryan and Logan in the room, well he wondered how much manpower Alice needed to hold down such a small young beauty for a simple paddling.

Alice waved at the men to grab the girl by her arms and legs and get her up on the table. Ryan and Logan grabbed her arms as Harper went for her ankles. The pretty girl hollered, her voice breaking with fear as the men grabbed her, “w what’s going on, help! Please Alice, please let me go, leave me alone!!”

They lifted the young beauty without any effort as she tried to struggle and kick but it was useless as she felt her body swing through the air and onto the table. Harper’s heart fluttered as her short skirt flew up exposing her pretty legs and white panty. He already felt aroused holding her slim ankles and he could feel his cock hardening watching the pretty girl about to get her comeuppance. They laid her out still struggling on the table as Alice looked her over. Then to Lily’s utter horror and everyone else’s surprise, she started unbuttoning the girl’s white blouse while the men held her on the table, Ryan and Logan at each arm and Harper down at her ankles.

“What’re you doing!” hollered Lily horrified at that her blouse was coming off in front of all these grown men. All the men, Ryan, Logan and especially Harper were amazed and wondering how far this was going, probably down to her underwear then a good paddling thought Logan. Alice had always just had the girls skirts pulled up so probably just the blouse and maybe her skirt might come off for a good paddling he thought.

“Nooooo…please Alice, please leave me alone,” hollered Lily hoping this was not going very far and embarrassed having her blouse taken off in front of the grown men. Alice unbuttoned the little girl’s blouse and pulled it open revealing a thin silky training bra for young girls. Harper gulped. He’d been with young naked women before but had never seen a young beautiful preteen girl undressed. But, he thought, it’s just her blouse and maybe her skirt before Alice applies the paddle.

Alice wrestled the girl’s blouse completely off with Logan and Ryan holding her arms, then helping her and making it easy. Everybody, including Alice, licked their lips gazing at the girl’s blemish free smooth milk white skin as the blouse fell away. Lily’s arms were up above her head pinned to the table and her underarms looked soft and completely hairless, not shaved but hairless at her young preteen age. She had almost no breasts, almost a completely flat chest but her small breasts were just starting to mound up and Ryan could just about make out her nipples under the thin halter fabric.

Alice grabbed one of Lily’s ankles and started slipping off a shoe and ankle sock as she ordered Harper to “take off her other shoe and ankle sock.” Harper obeyed slipping off the left shoe and nervously removing the girl’s white ankle sock as Cassandra removed the other one exposing the girls pretty white feet.

“Shoes and socks, for a paddling?” thought Harper as his stomach did flips realizing a little more clothing might be coming off than necessary for a paddling. With the shoes and socks gone Harper held the girls ankles and looked at her small pretty feet.

Lily felt vulnerable with her blouse removed and getting manhandled by the three men and wondered and hoped Alice would stop. The principal started tugging at the girl’s skirt zipper and side button then said aloud to the little girl’s utter shock and everyone else’s surprise, “everything comes off, little girl, all you’re your clothes, you’ll be completely nude a minute, stripped to the skin, butt naked in front of everybody. I promised you’d regret this day!!”

“OOH! No! No! Please don’t take my clothes off, I promise I’ll do whatever you want! Pleeeeeaase” she said almost crying with embarrassment. Her face and upper body had reddened realizing she was about to be completely undressed in front of the three men and everyone noticed her embarrassment as Logan said nervously, “gee look at her she’s really blushing red.” Lily felt so humiliated at the thought of her impending nudity in front of the grown men, her crimson blush spread over her pretty face as she felt the principal’s hands removing her clothes one piece at a time. She looked around with desperation on her face but her impending nudity thrilled the onlookers, Alice as well. Lily was quite a young girlish beauty and her imminent nudity gave the scene an unreal atmosphere as all anticipated her undressing, imagining the little pretty girl completely nude, her alabaster white body exposed naked.

Alice pulled the little skirt down off her hips exposing small white panties, Harper gulped nervously looking at her hips and the small panty as the skirt came off and she continued removing the skirt along Lily’s pretty slim legs. Alice stopped a moment as she flung away the skirt and looked at the nearly nude and helpless young girl. The white panty hugged her hips with the elastic waistband below her navel and, oh god! The mound of her vulva looked so prominent with the panty slipping into her genital slit and outlining her young hairless pussy mound.

The hapless preteen girl looked beautiful laying almost nude, just the panty and halter training bra left, with her alabaster white body and platinum blonde hair. But of course at her young age probably hairless everywhere else on her pretty body as Harper thought expecting her panty to come off any moment. He felt a little dizzy having never seen a girl her age completely nude, especially one so pretty. She was about to be stripped of her last garments, exposing the white expanse of her almost flat girlish chest and hairless preteen vulva, the thoughts and images were very arousing.

“Ok, off with your bra little girl, looks like you’ve got little budding breasts under that silky bra. Let’s get it off and see your…well…tits,” mocked Alice embarrassing Lily even more if that were possible in front of the grown men. Alice tugged at the bra pulling it up since it was just a small child’s training bra without snaps. As she tugged and lifted the fabric away from her mid-section the little girl’s pale pink nipples appeared. They almost blended with her creamy smooth white skin they were so pale pink but seemed almost as big as quarters showing she had just started puberty. She had small breast mounds hardly needing a bra.

The feeling in the room was intense as the girl’s last garments were soon coming off and everyone felt nervous and excited. With the help of Logan and Ryan the training bra came away from her upper body and arms, also to be tossed in the growing pile of discarded clothing. Her slim white body lay almost completely exposed, completely hairless, a delicious mix of white and pink and blushing red with embarrassment.

“Well little girl,” said the principal mockingly, ‘just your panty left and in a minute these big boys will get an eyeful of you completely nude without any clothes on at all, your girlish sex all exposed for everyone here to see.” Living alone with her mother Lily had never been nude in the presence of any males, men or boys and now these grown men were gazing on her almost nude body with her last garment, her panty, about to be pulled off completely exposing her hairless genital mound. She felt so vulnerable, exposed and embarrassed by the presence of males watching her being forcibly undressed.

Lily twisted her body, as if she could prevent her last garment from coming off, and groaned pathetically as Alice’s fingers grasped the elastic waistband of the panty. Lily twisted and turned as Alice tugged nervously on her panty, trying desperately but without any real hope to keep her last garment and her sex mound covered but knowing that in a few seconds the panty would get pulled off exposing her girlish genital mound in front of the principal and worse in front of the three grown men.

Her face and shoulders were blushing red as Alice tugged on the panty exposing the little girl’s lower white smooth tummy further below her navel. Even her frantic squirming did not stop Alice from deliberately in a slow manner pulling off her panty. Alice stopped for a moment just leaving her panty low on her hips but not completely off, barely just covering her sex mound. She knew that the deliberately slow panty removal and pause just before uncovering her genital mound would embarrass the hapless preteen even more. Harper gulped nervously gazing at the almost nude young girl with her panty almost off barely exposing the swell of her sex mound.

“And what shall I do with you after the panty comes off completely little girl?” Alice asked mockingly and leaving all with imaginations of what was next. “Well let’s take a look at your girlish sex little missy.” Lily groaned helplessly as Alice grasped the panty waist once again and tugged the garment just off the little girl’s sex mound. Harper almost gasped when her hairless white sex mound and genital slit were revealed as the panty came down further, off her hips. Alice gently tugged the panty down along her thighs and slim legs and with Harper’s help at her small feet she removed the thin garment completely and tossed it away into the pile of Lily’s discarded clothing.

All in the room gazed at the nude pretty girl laying on her back, her small feet held slightly apart and her arms way up over her head. Harper, holding her ankles, had the best view of her vulva, her genital slit and…wow…looks like her pink clitoris just poking at her slit. Her skin was milk white as snow and her nipples so pale pink on the small mounds of her just budding breasts, no hair at all on her body yet and her smooth underarms exposed.

“Boys, let’s turn her over with her butt in the air,” said the cruel principal as the hapless girl’s humiliation continued. The men easily flipped the cute nude girl over onto her tummy exposing her naked pristine white bubble butt to view. Harper held her slim ankles and made sure to keep her legs spread just enough to get a good view of “everything,” with her hairless virgin pussy still in his sights. The windows let in plenty of light and, as she squirmed trying desperately to get free, he could easily see her cute pink anus and the thin moist line of her genital lips.

Alice enjoyed humiliating the young girl and said aloud, “take a look at her naked white butt cheeks. They won’t be white for long after I get done” causing Lily to cringe tearfully. “I promised you 10 good whacks with the paddle young miss and now on your bare butt cheeks while the boys look on.” She walked over to her desk and retrieved a large wooden paddle; it looked menacing, making Lily cringe and tearfully whimper “oh, no, no please Alice, I’ll do whatever you want.”

“I know you’ll do whatever I want little girl. You just need a little humility and persuasion, and you’re getting it right now!” Alice whacked the paddle lightly against her own hand making a loud “thwack” noise that caused Lily to flinch noticeably and yelp aloud even though she hadn’t been touched yet.

Suddenly the paddle came down on the girl’s exposed ass cheeks with a louder “thwack” causing Lily to yelp out loud and catch her breath. She felt tears welling up in her eyes as the sting against her pretty bare butt spread across her naked ass cheeks. Harper, holding her small ankles, felt her legs go stiff as the paddle contacted her naked white ass flesh. As Alice had predicted her ass checks reddened immediately.

“That’s just the first one little girl and it’s for being so defiant, another 9 left to go.” After a few brief seconds, another “thwack” sound filled the room as the paddle came down on the girl’s bare ass a second time.

“That’s number two for talking back,” said Alice licking her lips as the little girl’s ass cheeks quivered and she yelped aloud again this time with a sob. Her reddening butt cheeks seemed to glow with heat as the crimson spread across the mounds of her pretty jutting ass. Her hips seemed to jump off the table and she tried to move her mid body around as if it might relieve the sting. Harper seemed beside himself gazing wide eyed at the naked little girl’s squirming as if she could avoid the pain, her pretty naked ass rising and moving with her milky white smooth flesh quivering.

For a third time the loud “thwack” resounded in the room as the paddle contacted the little girl’s cute reddening bottom. Alice seemed to not be in any hurry, allowing time between each stroke of the paddle to let Lily dread the next stinging blow to her sensitive butt flesh that was getting more sensitive and stinging with each stroke.

“Well as I said before your cute white cheeks aren’t white anymore as the boys can see for themselves,” said Alice deliberately reminding the humiliated girl that the grown men, boys as Alice preferred to call them, were witnessing her naked cheeks receive punishment. Then a fourth “thwack” sounded as the paddle continued to pound the cute girl’s naked ass flesh.

“That’s to teach you humility because you’re sassy and need to learn some manners,” came another rebuke from the cruel principal. Lily’s whole body seemed to quiver now with sobbing as the stinging on her bare butt seemed to grow with each blow. The ass cheeks of her reddening bubble butt also got more sensitive with each stroke making it feel more painful. “Ooohh, please, please Alice, it hurts!” sobbed the hapless child knowing another stroke would soon come down on her sensitive ass cheeks.

“Just a few more to go young missy, to really bring these lessons home and make sure you learn how to behave,” said Alice almost soothingly, aware that Lily had already been thoroughly humiliated and punished. “I promised you 10 strokes and I keep my promises, 10 strokes it will be,” she said without mercy.

“Are you ready for another stroke of the paddle,” said Alice putting Lily on notice and dread that another painful blow was about to make contact. Without waiting for any reply Alice swung the paddle causing another “thwacking” sound as it painfully contacted Lily’s exposed bare ass. Lily sobbed again louder as the stinging pain against her cheeks spread and her butt came off the table squirming on reflex to Harper’s perverse delight.

And so it went on with Alice delivering another admonition with each painful stroke against Lily’s crimson bare butt, the red had nearly turned purplish as the whacking on her butt cheeks continued.

Finally after the ninth blow of the paddle Alice asked “we aren’t going to sass the principal ever again are we little missy.”

“N…nnn…no Alice,” sobbed Lily completely chastened by the whole humiliating and painful experience.

“We’re going to obey our elders and do as we’re told aren’t we little girly,” pressed the principal once again.

“Ye…yyyy…yess, ma’m, Alice,” said Lily through her tears, completely subdued now.

“I know you’ve been through a lot, what with these boys looking on at your undressing until completely nude and these awful whacks with the paddle but I’m sure you’ve learned some good from this little missy and we’re going to get along from now on, aren’t we.” Alice seemed almost sympathetic. She was a master at disciplining little girls and she smiled sweetly as Lily responded through her continuing sobs. “Yes…yess, Alice.”

“You have one more whack coming since I promised the full 10 but it’s the last one.”

“Ohh!...please Alice, it…huuurts so much! No more, please!” Lily cried plaintively. All in the room felt sorry for the little girl as she seemed so completely chastened.

“No just one more, the last and I’ll make it better after,” said Alice with a parental almost loving tone. Then a last sudden “thwack” as Lily sobbed louder, her little white body quivering and her hips moving up off the table as the pain and sting persisted.

“And that’s 10!” said Alice as she placed the paddle down and walked over to her desk. “I know it’s been a hard day for you, having all your clothes forcibly stripped off in front of these boys and then having your bare butt whacked, again in front of male company but it’s all over now,” she said soothingly as she came back to the table, Lily still held face down. She had a bottle of white lotion in her hands and a towel drapped over her arm. She put some of the lotion on her hands as she stood over the little girl’s bare reddened ass. She spread the lotion onto Lily’s red ass cheeks soothingly, “here the lotion will make your sore butt cheeks feel better.”

“Oooo…oooo…Aaah…,” exclaimed Lily feeling the alcohol based lotion sting but it also felt cool on her glowing red ass cheeks. Alice fondled the little girl’s ass, applying the lotion and enjoying the feel of her soft fleshy butt. She rubbed thoroughly between the cleft of Lily’s bare cheeks enjoying the warmth of her naked flesh and little girl’s moist sex. She fingered the little girls pink anus as she slipped her hand between her naked butt cheeks. Harper’s mouth was agape while he stared at Alice feeling the cute girl’s sexual charms. Ryan eyes seemed glazed over and Logan looked nearly catatonic as Alice sexually fondled the pretty child so blatantly.

“Alright boys, you can all leave now, I believe we girls can handle everything from now on,” said the principal in a voice thick with arousal as she contemplated her time alone with the pretty girl. She draped the towel over the little girl’s nude body and put an arm around her as the men left the room dazed probably to remember this day forever.

(End of File)