Disciplined Pleasure

"Many a man thinks he is buying pleasure, when he is really selling himself to it." - Benjamin Franklin

It had been nearly a month since nineteen year old Pleasure's doctor appointment that altered her entire life. She was her oldest brother's whore now. Wholly and completely and forever, to do with what he wanted - just as she had been, from the moment he first kissed her at the doctor's office...

What she hadn't understood at first, was now that Pleasure was her brother's whore - it wasn't just her body that belonged to him. The next morning, her parents sat down with her and both her older brothers to ensure she fully understood, by consenting to be her eldest brother's whore - she was now his responsibility, and as such would be handling most of her decisions on a daily basis... even her parents would restrain themselves from liberties unless her eldest brother had given consent.

Initially, Pleasure hesitated to agree to such strict rules of possession. However, when she realized that her parents and brother recognized her eldest brother's claim and would be honoring the family's pact - that she wouldn't ever be able to be fucked by any of them again if she failed to accept the terms, she signed the pledge of possession.

Once signed though, her eldest brother explained that Pleasure shouldn't have hesitated & she would need to be punished. At first she laughed, but seeing the stern look in her brother's eye - she began to panic trying to make a haste retreat to her bedroom, daddy caught her arm though and although she struggled against him, Pleasure was powerless to stop him from lifting her off her feet.

Pleasure's momma held open the basement door and followed the men downstairs to family room. Long ago, the family room was outfitted with soundproofing and Pleasure had been told at the time, it was for movie night not to disturb the neighbours - but that initial panic rose, as she realized that no one could hear them...

She need not have worried about the sound of her screams though, as the men ripped her sheer little nightie from body, momma placed a leather strap in her teeth and instructed Pleasure to bite down, and as she did the strap was fastened around her head. She was then leaned over one of the benches at the bar before being struck by a leather covered paddle! She winced, trying not to cry as she received her punishment - but it hurt so much!

One, two, three... she made it to five strikes of the paddle before she couldn't hold back her tears. Six, seven... she felt her head being pulled up by her braid. Eight, nine... it wasn't anger in her brother's eyes though, it was lust! And as their daddy landed the tenth strike to her tender bottom, cum began to run down her inner thigh!

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At school the following Monday, Pleasure was so exhausted from fulfilling her whore duties after her punishment, she could barely keep her eyes open during her classes. This didn't go un-noticed and when several teacher's expressed their concern to the principal, she was sent home early with a note suggesting to be better prepared on the morrow or risk detention.

After her punishment over the weekend, Pleasure had been afraid to show her momma the note - however when she finally worked up the courage, momma reminded her that Pleasure needed to show her brother the school's note. Reluctantly, with her head hung, she knocked on her eldest brother's door...

As she entered his room, Pleasure began taking her clothes off, as one of her new whore rules was that she wasn't to be clothed in the house unless there were guests present. Her brother looked up from his computer and smiled, but jumped up to hug her tight when he saw the worried look on her face. With tears on her cheeks, Pleasure apologized for getting into trouble at school - however, her brother laughed as he wiped the tears away and promised that he'd try to make sure she got more sleep.

Then taking her hand, sat back down at the computer and pulled her into his lap as he showed her the design of his new website. He explained since he wasn't going to allow her to keep her after school job, to ensure she was at his beck and call, they would need to supplement her spending money somehow and he'd decided to publish pictures and videos of her. He could feel her body stiffen and as he began to slowly finger fuck her as he continued to tell her about the site, opening one of the videos loaded. It was of her first spanking and as he assured her, her face was never visible nor would it ever be - but her cunt... her asshole... well she would show the world just how much of a whore she was & with that, he lifted her quickly off his lap, spun her around and dropped her with force on his erection. With a gasp, she grasped his shoulders to steady herself as her brother lifted her up and down on his hard cock until she came once, spurring him on to fuck her tight cunt even harder until she came again when he emptied his load in her.

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True to his word, her brother made her quit her job at the grocery store and expected Pleasure's tight pussy promptly delivered to him every day after school. Over the next week, Pleasure continued to try and keep alert in school - however, by mid afternoon classes, the steel butt plug her brother insisted she wear to ensure that she remained awake during class, became unbearably uncomfortable the more she squirmed in her desk chair. So she began cutting her last class to get home as early as she could.

On the third day that she arrived home early, her brother had that stern look in his eye again and demanded to know why their momma received a call from the principal about her skipped classes. Pleasure couldn't help the fear that flickered at memory of her first spanking, and her brother seeing the glimpse of fear assured her as he guided her to the family room - he wasn't angry that she had skipped her classes. Her relief was short-lived though, when he explained that she failed to ask permission for her truancy and again she found herself bent over one of the benches along the bar.

Pleasure had been about to remind her brother that he had forgotten to remove the butt plug... however, with the first crack of the paddle, she realized he knew and that it was part of her punishment, to have the small steel plug feel like it was being buried deeper and deeper into her asshole with every lash against her beautiful bottom. And again, the cum began to flow from her...

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The next morning, Pleasure's eldest brother woke her earlier than usual for school, explaining he'd had a request on the website & wanted to film it before she left for school. She was still sleepy as he guided her down to the family room, but was compliant and laid down on the game table where the lights and cameras were already set up and her brother slid a position pillow under her hips to elevate her ass to just the right angle before placing her blindfold on and lacing her wrists to her ankle restraints, that when pulled on, spread her legs to expose her sweet cunt and dainty little pucker.

Normally her own moisture was slick enough to accommodate the toys Pleasure's brother had been using to fuck her on their website, so she was surprised when the cool lube touched her ass. After squeezed some lube in her pucker, he reached for a rather large carrot - the end was naturally rounded and the seven inch rabbit food's circumference tapered from just under an inch at the top to nearly three inches at the base. Pleasure yelped at the cool temperature of the vegetable, but that did not deter him and her brother continued to ease the carrot into her ass, and when only the large base was all that could be seen, did he pick up a small cucumber...

Small wasn't quite right, the cucumber was nearly ten inches long - though it didn't have a large girth, with the carrot shoved in her ass it was tight enough and soon Pleasures cum coated the cool cucumber. He brother let her climax once before removing the cucumber and feeding it to her, and she wrapped her lips around it like she was sucking a cock, biting off the tip and licking her juices off the edible shaft.

Fuck he was hard! Her brother loved having his baby sister as his whore! He loved that she enjoyed being fucked and he loved pushing her limits... just as he knew he was about to. He gave the carrot another few strokes in her ass before picking up the lube coated zucchini. It was longer than his cock by nearly four inches and tapered only slightly, being about two inches on its end nearly the circumference of a beer can at its largest. Pleasure felt a pinching and gasped in pain as her brother pushed the narrowest end into her still wet cunt. He held it there, allowing her to get used to the fullness, before rubbing a small vibrator against her clit in tiny circles and as her orgasm began to build, he turned up the speed and eased just a bit more of the zucchini into her tight hole.

It wasn't until he knew she was at the apex of another climax, did he dare to attempt to ease the widest part of the zucchini into her and Pleasure's scream rang in his ears! Slowly, very slowly, to avoid tearing her, he pushed the fat zucchini into his sister's stretched twat, in long steady strokes, easing it in and out - it was only when the painful whimpers began to resemble growls of ecstasy did he begin to fuck her in earnest, only stopping his assault when her final orgasm won out shaking her whole body to its core... only then did he grab his throbbing cock and jack his cum all over the protruding vegetables in Pleasure's cunt and ass.

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Pleasure didn't make it to school that day. She had passed out after the overwhelming video session, only waking the next morning when her alarm jolted her from a delicious dream of having her pussy licked...

Glancing at the clock, she realized she barely had time to shower before catching the bus for school! Oh the hot water felt so good... her muscles were so sore... oh her life was so different now that she was a whore!

The younger of her two older brothers knocked on the bathroom door, not waiting for a response - Pleasure squealed when he entered the shower, but when he told her that their eldest brother had given his permission, she allowed him to push her to her knees. And as the hot water pulsated all around them, she wrapped her mouth around her brother's morning wood. She knew it was late so used just a little more pressure than he normally was used to and was rewarded with a quick hard cum for her efforts. Planting an even quicker kiss on his surprised mouth, Pleasure grabbed a towel & raced back to her room to dress for school.

She brushed her hair and tossed it up still wet into a clip and grabbed her school uniform from the closet. She had already inserted her steel butt plug and was just applying a sheer gloss to her pouty lips, when momma popped her head into the room to tell her daddy could drop her at school if she was ready to leave right then!

Even with the ride from daddy, she arrived late to home room breathless and a little flushed from daddy fingering her pussy on the drive to school. Before she took her seat, the teacher stopped her and told her that she needed to report to the principal's office.

The principal was in a meeting and she was told to sit outside his office to wait. Pleasure was still sitting there nearly twenty minutes later when her brother appeared at her side. He told her to relax, he was sure there would be no detention but once the school called a parent or guardian needed to be in attendance for the new principal's meeting.

Just then the office door opened, and the principal asked her and her eldest brother to step in. Pleasure hadn't met the principal before, as he'd just transferred in at the beginning of the semester and she had missed a lot of classes and school assemblies.

He was very handsome, a black man in his early thirties. He smiled gently at the clearly nervous girl. He had glanced at her file just before the meeting, and remembered reading she was nineteen - but with no make-up other than the sheer lip gloss, she looked barely older than fifteen and the principal felt his trousers tighten.

He cleared his throat and asked her brother if their parents would be attending the meeting - her brother shook his head, explaining that his parents were tied up with work as both he and his sister were above the age of majority, he was empowered to act on their behalf for his sister.

The principal nodded and explained it was a little complicated, that with the shift in the school's disciplinary policy, there had been a return to corporal punishment in the school bylaws. And as Pleasure had begun skipping classes and now was tardy to classes, the school was being forced to take action.

Her brother agreed with the principal, that Pleasure needed to learn there were consequences to actions and was sure that his parents would support the decision. His only concern was that they would want to ensure that any actions taken would be documented for her record and of course that it be in private. The principal consented and got up and locked his office door returning to his desk and asking Pleasure to bend over the desk.

Nervously, as she got up, Pleasure looked from the principal to her brother and back again. The principal asked if she would prefer a ruler or his hand for the spanking, and again she looked to her brother for help. Her brother stepped forward, his camera in hand and told the principal that she would learn the lesson better if it was an old fashioned bare bottom spanking.

This startled the normally unruffled principal - however, the idea of touching that beautiful ass even if was to strike it... his cock nearly broke through his zipper at the mere thought! Even when her skirt was lifted to reveal her milky white ass, it wasn't readily apparent that she had not panties on, he simply thought she had a g-string like half the teens in school - also as he was standing to the side, and not directly behind, the steel butt plug with the gleaming crystal wasn't clearly visible. It wasn't until the third strike of his hand, did the principal feel the plug... but the look of utter dismay when he did...

The flustered principal dropped into his chair, demanding to know what that was - however, nothing prepared him for the shock, when Pleasure's brother instructed her to show him and she reached back to spread her butt cheeks for him! There twinkling at him, as a beautiful crystal topped steel butt plug - far more beautiful though was the pussy directly below it! A pussy he recognized!! This was the pussy that had claimed nearly all his online time at home for the last week... this was the pussy that had been food fucked just for him yesterday, forcing him to be late for a pre-class meeting.

Unable to control his impulse, the principal reached out a finger and traced the glorious cunt that had been presented to him, whispering "so beautiful" under his breath. But common sense yanked his hand back, this was a student!

The startled principal stammered an apology... but he couldn't tear his eyes from Pleasures still exposed pussy. Then again, he briefly regained his composure and told her she could get up - but the teen knew better, she dare not move a muscle until her brother granted permission or risk an even harsher punishment once they returned home.

When she didn't move, the principal finally tore his eyes from her and looked to the brother for explanation - was even further surprised to find Pleasure's brother was still holding the camera and that it was aimed directly at his sister's twinkling butt plug!

Her brother very calmly told the principal that although user names were private, the name on the credit card that paid to watch the food fucking was not. The principal was outraged and jumping to his feet, demanded to know how much her brother was planning to blackmail him for?!

This time, before he responded - her brother put away the camera, then turned to the principal and apologized for the impression he was getting. In a steady voice, he explained for the administrator, his baby sister was his whore and since the principal had clearly enjoyed her performance online - he wanted to invite him to share Pleasure's body with him.

Dumbfounded, the principal dropped back into his chair. It was as though someone had walked into his deepest fantasies and cherry picked a favorite one to allow him to act out... a student on his desk... her ass cheeks spread wide just for him... again, he reached out a finger and traced the lips of her cunt... they were damp...

He looked back to her brother, but he had already dropped his pants and had his cock at his sister lips and as he filled her mouth - her principal pushed his finger into her wet pussy... oh god, she was still so tight! After a few strokes, he pulled the finger out and licked it, tasting her sweet nectar. Then leaning forward, he pulled her cheeks farther apart and began licking the cunt he'd been dreaming of for then last week. Just as he traced her with his finger, he let his tongue trace her pink folds before plunging it into her and fucking her with it. As she started to cum, he could feel her contracting around his tongue, milking it tightly as if it were his cock.

This was too much! He leaped out of his chair yanking his pants down and buried his cock in her cunt up to the hilt! So turned on, he only lasted a few strokes before blasting his load, and the harder he fucked her the deeper her brother's cock was slammed into her throat.

After they had cum, the men both striped the rest of their clothes off and began undressing Pleasure as well. Her brother loved watching the black man's dark slender fingers caress her milky breasts... and when he latched his lips on her tender nipples, he almost lost his load again!

Her brother laid down on the desk and pulled her onto him, while her brother brought her hips to his cock - her principal pushed his cock, still slick with both their cum, into her eager mouth. Mmm... he could feel her grasp his butt cheeks and liked feeling the air kiss his ass hole, but it when he felt her brother's finger ease into his ass - that was when he grabbed her head and began fucking her mouth as hard as he had her cunt! Fuuuuuck... her brother's fingering matched his own thrusts and he felt his balls tighten and as the school bell rang, he emptied his load deep into Pleasure's throat.

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As his student and her brother gathered their clothes, the principal sat back in his chair in a daze... had this just happened? Had he just fucked a student? Ten years of teaching to reach the point where he was a tenured principal for a private school and this is where he found himself?

And then Pleasure's brother broke the silence, telling the principal that he needed to know his whore was being given a proper education - however, he didn't think the regular curriculum was working for the skills she needed and wanted to know if the principal would be willing to be her primary teacher daily during school?

The principal reached out and caressed Pleasure's ass and nodded slowly, as he assured her brother that yes he would be more than happy to be of service. The two men shook hands, and the siblings turned to leave his office - when Pleasure reached into her school bag and brought a tin. She turned back and handed it the principal, as she kissed his cheek Pleasure smiled shyly and told him she'd made it from scratch... chocolate zucchini cake.