The Life of Sara Wincester Ch. 03

"Hey girl!" Rachel beamed, feeling the fabric of her skirt, "We're almost matching today!"

Rachel was talking about their uniform, both girls had chosen to wear their mini skirt and thong, however, where Sara wore a thin, see-through crop-top, Rachel simply wore black pasties over her nipples, shaped like an 'X' which had the words "Fuck Me" written on them in white. Sara nodded in approval, running her thumb over the words.

They both walked towards the school building while chatting away about all their latest happenings since last week. They walked into the campus grounds, past the giant arch that read 'Freeside Academy.'

Freeside Academy was a unique combination of 'Late Secondary' and 'Tertiary Education' aimed at educating the adult youth. Once someone had reached eighteen years of age they would join the adult world, be treated like another respectable member of society and get to enjoy all the perks of adulthood, including the social rules of 'Sexual Conversations.' Students aged eighteen to twenty-five would come here to finish the last part of their education, as well as learn about their roles in society.

Unfortunately for Sara, 'anyone' who turned eighteen would eventually be moved to Freeside Academy, which meant that her brother, Max would soon be enrolling in this very school. He was currently in the transitional phase having recently turned eighteen a few months back, but soon he'll be riding the bus, and her ass, all the way to school.

Sara sighed at the thought, while she held no true ill will towards her brother, she was all too aware of how obsessed he was with her and while truthfully she enjoyed the newfound closeness with her brother, she could also get really annoyed at how pushy he could be.

Max had turned into an adult just before holidays had started, so Sara had spent two months, most of which being her summer break, having to satisfy her younger brother's sexual frustrations. She knew that becoming an adult was an exciting moment, finally being able to fuck and have your way with almost anyone you could meet, but Max never seemed too interested in leaving the house to meet new people.

Part of that could have been the fact he was the oldest of his friendship group and now was separate from the children, but most of it had to do with his, until recently, harmless crush on his big sister. Sara mainly blamed herself for spoiling the boy, she should have said something sooner but she was having just as much fun.

She didn't hate him, however, while having several cocks in her face throughout the day was pretty normal, having the same cock chasing you around all the time could get very irritating.

Rachel led her by the hand through the halls of the building, her soft fingers interlocking with her own calmed her down. She at least could enjoy what time she had left and she knew deep down that she'd enjoy whatever perverse thing her brother would do to her at school.

As they neared her class Sara looked at the classroom numbers and realized that hers was at the very end, she looked at Rachel and smiled sweetly. Rachel chuckled as Sara let go of her hands, she opened the door to her classroom and looked around the area.

Most of the other students were filling in, a few of them, mainly the boys gave both of them a sly smile. Sara could tell she wasn't going to like the reason why, this was quickly confirmed as Rachel squealed with delight.

"Oh goody!" Rachel beamed, shaking Sara on the shoulder, "It's our turn on the board!"

"Seriously? Today?" Sara whined, reading her name written on the whiteboard under the title 'Class Relief.'

Class Relief was a rather simple yet important position. Each day, four students would be chosen at random, two boys and two girls to be assigned to give the remaining students sexual relief throughout the day. This was to prevent classrooms from turning into all-out orgies.

It's impossible to teach a room full of horny teens and young adults if all they do is fuck each other, so a handful would be volunteered to help 'keep order.' While being on duty was a lot of fun, Sara much preferred to use the relief rather than being the relief, it was far less tiring and required a lot less concentration.

"Which one do you want?" Rachel asked, holding out two pink collars, one read 'Cumdump,' the other had 'Sex Doll' written in silver glitter.

"Cumdump" Sara replied with a chuckle, grabbing the appropriate collar and attaching it to her neck, "Seems to be my nickname these days."

The other two collars were handed out to the two boys of the day, both blue, one reading 'Asshole' and the other 'Good Boy'.

Sara watched as James, A small, thin boy who was wearing the 'Good Boy' collar was immediately snatched up by Ruth, a tall tomboy woman who promptly pulled him onto his lap at the back of the class and forcefully jerked him off. Taking pleasure in the moans and gasps James made as she used him.

"Okay, what's the plan of attack?" Sara asked Rachel, hoping to divide the load between each other.

The only response she got was the sound of gagging and slurping as Rachel had already been engaged by three boys. Already on her knees, Rachel sucked on the cock of one boy while her hands jerked away at two other dicks. A true multitasker, Sara couldn't help but be impressed.

The remainder of the class looked at her hungrily but before Sara could be chosen by someone a voice called out from behind her.

"I'll be using this Ms Wincestor for this session." Said a firm, strict feminine voice as it confidently entered the classroom.

Ms Haywood was first periods teacher, at thirty-eight, she had a figure that screamed 'certified MILF'. Specifically, in her thick thighs and large ass, her attitude wasn't motherly at all, however. She was a rather stern and altogether grumpy woman, although some people were into that, Sara often found her very intimidating.

"You can take a position under my desk." Ms Haywood continued, walking towards her desk, not even looking up to greet the class.

Sara walked towards her desk, students still reaching out to grope her as she passed. the desk was cut out in a way that someone could easily crawl up under from the front, usually, this whole would just be used as a pleasant window to the teacher's crotch, but it also made for easy access for students to give oral.

As Sara crawled through the desk, she could see the tight, short pencil skirt that Ms Haywood was wearing. She obviously wasn't wearing any underwear and Sara could smell the fresh scent of semen on her legs. Someone had recently fucked her before class or more accurately, someone had fucked her thighs.

Ms Haywood raised her leg, revealing her cunt along with the sticky residue of still warm cum on her inner thigh. Before Sara could get any further, the leg wrapped back around her neck and pulled her in, the sticky feeling of semen mushed along her cheeks as her mouth was yanked towards her teacher's cunt.

Admittedly, Sara did not have as much experience in cunnilingus as she'd wanted, she wasn't a total virgin and she'd practiced a lot with Rachel and her own Mother, the latter taught her all the ways to please a woman. However, it wasn't as common for her to give head to a woman compared to the amount of cocks she had swallowed over the years.

Her lack of experience however wasn't going to stop her from giving the 'old college try'. Sara licked her lips, slowly bringing her tongue out of her mouth and brushing her tongue along the seam of Ms Haywood's pussy, her mouth instantly being invaded by a wave of heat. The pressure was getting harder to control and Sara felt the need to move faster, but she needed her teacher to loosen up. Sara felt around as her tongue moved faster against Ms Haywood's wet pussy, all the while saliva dripped from her chin. She began to suck on Ms Haywood's clit, moving her tongue in circles over it. As she continued to lick Miss Haywood's pussy, she felt the teacher's hands gripping at her hair softly, a sign of approval that filled Sara with pride.

Once she found confidence in her oral skill, Sara relaxed into the position, lapping away at her teacher's cunt. She couldn't hear what the lesson was about as Ms Haywood's legs held Sara's head in place for the remainder of the class, she would look up at the older women to see if she was still happy with her performance.

Ms Haywood would continue to say nothing to Sara, barely acknowledging her presence beyond the occasional head pat or by squeezing her legs. Occasionally she would feel hands from behind her and guessed that students would fondle her ass as they approached the desk.

She didn't know how many times that happened during the lesson, she just kept licking away at her teachers pussy like an obedient dog, completely losing track of time. After what felt like fifteen or twenty minutes of oral servicing she finally felt Ms Haywood's legs clench around her as she shuddered. The woman's face held its composure as Sara suspected that nobody else in the classroom would even realize that Ms Haywood had just came. Once the last of the spasms had stopped, Ms Haywood untangled herself from Sara, allowing the young girl to sit upright, under the desk, a wide smile across her face.

"Good work today, Ms Wincestor." She complimented, causing Sara to flush with pride.

Sara spent the next minute using her tongue to clean up around her teacher's thighs before exiting the desk. She took a moment to admire her handiwork before returning to her usual seat with a smile. She turned around and saw Rachel, who was currently under the desk of another boy at the back of the class. She appeared to have worked her way one by one down her row, her ass swayed hypnotically as her head bobbed back and forth.

The bell rang out, signaling the end of class. Sara waited patiently at the classes exit while all the students filed out while she waited for Rachel to finish, she watched as the teacher grabbed her things and left the room, stopping briefly at the door to look back at Sara. She pulled her in for a single deep kiss before walking off without saying a word, a rather intimate action that left Sara feeling rather warm inside. Rachel walked up behind her and locked her arms with her.

"Wow, it's almost lunchtime! Time sure flies when you're on relief duty." she beamed as she led Sara towards the cafeteria. "What are ya hungry for?"

Sara laughed, "How can you think about food? Didn't you just swallow like, five loads in a row?"

Rachel giggled in response, "Please, that's not a proper meal. And I only swallowed three of them."

"Well, three isn't bad," Sara commented, pulling out her phone as they reached the doors of the cafeteria. "I think I'll go for something light, pasta or a salad"

"Salad?" Rachel questioned, her eyebrows raised, "That doesn't really seem like fun at all... But whatever. I'm definitely gonna go for some nachos though."

Both girls lined up and collected their food, making sure to keep relieving anyone who approached them. When they sat opposite one another and ate Sara continued to chat quietly with Rachel, occasionally interrupted by the odd student shoving their cocks in her face.

Usually, she would sit with a larger group of friends, but being on duty meant she had to be available at all times and she knew her friends would take full advantage of that, she wanted to actually get some time to eat. Halfway through the meal, Rachel's eyes widen slightly, Sara knew exactly what she was concerned about and sighed.

"Uh-oh" Rachel sighed nodding behind Sara with her eyes, "Here comes the Virgins."

"Great..." Sara replied, readying herself.

The sound of several teen-aged boys chuckling grew louder and louder. 'Virgins' weren't literally virgins but was the nickname given to anyone recently turned eighteen. They were new to adult society and were a little too excited to take part in Sexual Conversations.

'Virgin' boys in particular would often not fully respect all the subtle social rules that went along with it all. In short, they all acted the same way as Max would at home, uncaring about anyone or anything beyond getting themselves off.

Beyond Rachel's comment, there was no other warning before the Virgins descended upon Sara, pushing her forward and lifting her up just enough to shove a cock directly into her cunt. Another boy forced his cock into her throat while a third ran around to Rachel, Sara didn't get a chance to see what the boy ended up doing to her but by Rachel's excited moans she guessed she was getting a similar type of assault for the rear.

Usually, such a forceful introduction would be met with arguments, however, their duty collars labeled them as open to anything, within reason, so Sara relaxed her jaw and allowed the boys to relentlessly fuck her holes.

One boy even managed to slip his finger inside her asshole as he fucked her, she felt him use his other hand to stroke up and down her clit whilst penetrating her. It hurt a bit more than she liked, but she was glad that Rachel was there to distract half the boys because she honestly couldn't have handled all of them by herself.

Truthfully she was a little thankful for spending the holidays with her own 'virgin' brother, it prepared her for moments like these.

After several more moments of this intense sexual treatment of the two of them, the boys finally tired themselves out. Two torrents of semen flooded down Sara's throat and up in her pussy, with heavy breathing, Sara tried desperately to catch her breath. The upside of dealing with Virgins was that they never lasted as long, often looking to just cum as fast as possible and move on.

Sara relaxed as she watched the two remaining boys finish in Rachel, one boy was happily fucking her asshole. He came suddenly and collapsed onto her back, pushing Rachel forward and releasing the second boys cock from her mouth.

"What the hell, man?" The second boy complained, obviously not finished yet and annoyed that his friend's orgasm had ruined his.

Not wanting to be blue-balled, the boy opted to stroke himself off to finish. Specifically, he chose to aim towards Sara, who was currently looking down at her salad and attempting to gather her composure. A quick spurt of cum shot across the table, a few drops sprayed along Sara's nose but the bulk of it landed directly in her salad. Now it was Sara's turn to complain.

"Seriously, dude?" Sara whined, giving the younger boy a glare. The boy simple responded with a shrug.

"What?" He said nonchalantly, "I thought you needed some dressing."

Sara didn't bother to give the bad joke a response, electing to continue to glare at the boy till he left. Once they left, she and Rachel collected themselves and went back to chatting. Sara poked and prodded at her salad with a fork, she didn't understand the boy's obsession with cumming on food.

Her brother would do it all the time, she learned pretty early on not to ask him to bring any food, from homemade sandwiches to Uber eats, any food for her that passed by her brother's hands would quickly find itself coated in his seed in one way or another.

Sara didn't have anything against drinking down cum from time to time, but she much preferred to keep it separated from her food. It would get pretty tiring if everything she ate all ended up tasting like semen, but more than that, she didn't understand the fascination with cumming on things. It just seemed gross to her, did the idea really arouse people that much?

Her answer came immediately as Rachel watched her eat with awe.

"What?" Sara asked, placing another forkful of salad into her mouth.

"Nothing..." Rachel replied, watching on as Sara swallowed another mouthful, "I think I just like, discovered a new fetish."

Sara shook her head and chuckled, "Try doing it for 'every' meal... you'll miss normal food after a while."

"Maybe I might." Rachel grinned in response.

The bell rang again as lunch ended, prompting Rachel and Sara to stand. They made their way over towards their next classes, today felt partially like a waste of time, being on relief duty meant that she wouldn't be able to partake in classwork.

The next few classes went by rather quickly, most students preferred some form of oral under their desks while they worked, which was slowly killing her knees, Sara wished that along with collars, the school would provide knee pads.

Thankfully a handful of students opted to have her climb onto them or have her bend over their desks, one class broke into groups to work on an assignment and simply allowed Sara to lie on her back while they all fondled and fucked her in a circle.

Before long, the school day was over. Sara, Rachel and all the other students on relief duty handed in their collars and headed to the showers. All bathrooms and showers were co-ed and sexual encounters in there were a given but everyone on relief duty would be too tired at this point in the day to try to initiate something themselves. The hot water felt glorious after a long day in class, Sara washed her face, body and hair thoroughly. She then dried herself off and dressed into a fresh uniform.

The two girls continued chatting all the way to the school's entrance, both girls continued to hold hands as they walked towards the line of cars. It didn't take long before Rachel spotted her Father's car.

"Daddy!" She yelled out, running over to the car, the window sliding down to reveal Mr Johnson waving out.

His hand wrapped around Rachel's waist through the window and placed steadily on her ass.

"Hey Pumpkin, how was school?" He laughed, kissing his daughters belly as he leaned up to the car window. "Afternoon Sara!"

Sara waved back as she pushed her pelvis towards the car window. Mr Johnson placed a second hand between her legs and rubbed her pussy as casually as one might shake a person's hand.

"Good afternoon Sir." Sara moaned, his fingers didn't stay there for long.

Rachel threw her bag into the back seat before turning back to Sara and giving her a loving kiss goodbye.

"Talk to you later!" Rachel waved as she ran around the other side of the car. She giggled as she sat in the passenger seat, staring at her father. "oh my god, Daddy! You're already so har-"

Her voice was cut off as Mr Johnson pulled his daughter down onto his cock while driving off. Sara waved as the car drove away before continuing her walk towards the bus stop.

She took a deep breath before climbing aboard the bus, still very much sore in parts of her body where she'd been fucked all day. She was too tired to entertain any commuters, so the trip home was overall uneventful. Once the bus reached her stop, she had to move an older woman who was using her as support while someone else fucked from behind, thankfully there was a handrail nearby she moved to, letting Sara pass. Sara made sure to thank her bus driver, allowing him to pinch her nipples for a brief second before getting off.

The walk home was also rather relaxing too. Only one or two elderly women were loitering about the roads or near the sidewalk as they shuffled past each other, nobody was in sight. Sara enjoyed the silence of the streets as she strolled along with them in front of her house, the only sound was the occasional passing car and the occasional dog barking somewhere far away, however, even those were drowned out by her music. After about five minutes she reached her house, pulling the door open before taking a step inside.

Inside, Sara was immediately greeted by the sight of her Mother and Brother lying naked on the couch. Her mother was sitting upright and smiled as Sara entered the living room, Max lay across the woman's lap, fast asleep while he subconsciously suckled on his Mother's large breasts. Her hand was gently stroking and rubbing his partially erect cock, there was also a small coating of cum already covering her hand. Mom had obviously been giving Max a relaxing nursing handjob while he fell asleep. Sara shook her head, she thought that her Mother spoils Max far too much but didn't say anything, she was too tired to risk waking her Brother at this time.