Naive Teacher does Cheerleading

(This is an edit to fix a few mistakes or broken tags)

This short tale is part of the "Naive Teacher in Winston" stories. It is strongly suggested that you read some of the other Chapters first.

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Foreword

Everyone in this story involved in any sexual activities is at least 18 years old. This story is not real and probably could never be real in 2023, so any correlations with real life are mere coincidences.

Thanks for being patient with me. I have not had much time lately as summer/family/work are all taking over what little time I have to spare. Expect a couple Jessica chapters soon and then a mainline Naive Teacher chapter eventually!

Enjoy the read,

~ Potato Head

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Potato Note: This story happens during the events of Chapter 17 (not yet published at the time this story came out). It is not crucial to read chapters 14-17 first, as this is a side story involving Lana and her students.

Potato Note 2: This whole tale is only 3h long; it's supposed to be a side adventure for Lana and some of the students.

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Day 19 -- Friday

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Early Afternoon

The gorgeous 5'3 brunette locks her large green eyes with the dark-skinned bus driver through his rear-view mirror. He smirks, and she reciprocates with a shy smile.

Her ample 38DD breasts, constrained in only a tight red sleeveless top with a black stylized WS logo, shake erotically due to the bus' constant vibration. She is braless. The driver licks his lips, and the young teacher's cheeks turn slightly red. She squirms in her seat.

The man pumps his eyebrows suggestively at her. She averts his gaze but timidly opens her toned, thick legs, clad in a pleated red skirt and white knee-length socks. She opens them until her diminutive red thong is fully exposed to the driver. The underwear also has the school logo in front, a stylized WS.

The teacher feels warmth spreading from behind her panties. The black driver caresses his crotch obscenely. Her mouth opens slightly, images of his dark manhood flash in her mind. She shifts in her seat.

Trying to compose herself, the young fiancee looks out the window and sighs. However, her legs remain wide open, teasing the driver with the sight of paradise.

'What bad news this morning. I wonder if Dens and I will ever be the same,' she reminisces. 'So many things happened in the last few days. Gosh.'

The busty teacher sighs again, a tad overwhelmed.

'And now Chloe asked me to do this... Ugh,' she touches her temple. 'At least I get to keep this outfit,' she smiles, glancing at the Winston Cheerleader uniform. 'Can't forget that I have to meet that bastard Uwe at the diner later today and tutor Greg and Zack afterward.'

She feels her asshole throb as the tiny purple butt plug lodged inside her stimulates her virgin hole. Not a lot, just enough to keep her in a constant state of arousal.

'I didn't even have time to remove Teddy. He's such an inconvenience right now', she laments. She thinks briefly and shakes her head, 'Oh, well. It's good training for my anus, according to Mary. So, this is for the better. Just hang on, Lana. It's going to be worth it for Dens.'.

Lana Cox looks at the green landscape and sighs again, 'Why me?'

~~~

Earlier this morning at School

Lana Cox had just arrived at the Staff Room when the volleyball team's captain, Chloe Chase, rushed in.

"Miss Lana, I need your help!" the blonde student declared. She is Lana's class representative and is a crass 18-year-old with a tight athletic body and perky 36C breasts. Albeit her naughty behavior as of late, she is still a virgin.

The teacher's eyes widened, and she straightened herself almost automatically. She felt warm inside, ready to help her pupil. "Hi, Chloe. What is going on?"

"The girls have food poisoning! We are a few members short!" Chloe said desperately.

"Oh, no! That is terrible!" Lana exclaimed worriedly.

"Right?!" The blonde agreed. "We are cheering for the wrestling squad this afternoon. It's a major match!"

The naive teacher cocked her head, confused. "How can I help?"

Chloe placed her hands together, "Please, fill in for them!"

"Huh?!" Lana exclaimed, surprised. She glanced at Prof. Henry, who seemed interested in their conversation. "Wait... Uhh... what... I mean..." she stammered, not knowing what was going on. She took a deep breath, "What do I have to do?"

"Easy!" Chloe said with a broad, cheeky grin. "Just be a cheerleader. Jen and I are the only ones not sick."

"Cheerleader?" Lana repeated, baffled. "Were you not on the volleyball team?"

"Yeah, we do it on big away games," the blonde student explained. "The boys also cheer for us when we play away. It's an arrangement between the teams."

"Hmm..." the teacher processed the new info.

"And I love to see the boys cheering from the sidelines," Chloe winked naughtily.

The teacher muttered, "Ohh..." her imagination was running wild.

The blonde student approached her teacher and held her hands. She looked deeply into Lana's eyes: "This is a match against our rivals in the regional league!"

Lana was taken aback. She awkwardly said, "I see..."

Chloe nodded, "It's serious! They are way better than us, so we need to support the boys. We may finally have a chance this time. All the boys have been practicing a lot."

Henry cleared his throat, and the two women looked at the old, frail professor. "Think of it as part of the Program, Lana," he grinned, imagining the big-titted teacher wearing a cheerleader outfit.

Lana nodded weakly. 'Prof. Henry is right. It's expected that I help my students with whatever they need. I'm just unsure about this,' she gulped. "Uhh... I have never done cheerleading before..." she admitted.

Chloe assuredly placed her hand on the anxious teacher's shoulder. "Don't worry about that, Miss Lana. We simply cheer the team and lift their spirits. There's no routine or anything."

"Oh... all right. It is my duty to help," Lana said, glancing at her older colleague. "Is there a uniform?"

Smiling widely, the blonde student ruffled through her backpack and produced a small sleeveless red top with a black school logo, a short pleated red skirt, and long white knee-high socks.

Lana's eyes widened at the outfit. "Hmm, is there a sports bra or some shorts? Those spandex ones," she asked, hopeful.

Chloe giggled, "Don't be silly, Miss Lan-... ah!" She exclaimed, and the gullible teacher almost sighed with relief, thinking her student remembered a missing piece. "Are your panties red like mine?" Chloe asked, lifting her skirt and showing her tiny underwear to her teacher.

Lana gasped, and Henry let out a pleased exclamation. "Yes..." said the curvy brunette blushing.

"I need to make sure," the hot slutty student said, grabbing the hem of the teacher's white skirt and exposing her red panties. "They're red. Not bad. Is it a thong?"

Prof. Henry cheekily lifted the back of Lana's skirt, exposing her fat ass and essentially leaving her bottomless in the Staff Room. "Indeed they are!" He confirmed.

"Eeeep!" Lana exclaimed, moving away from their lewd hands. 'Oh, gosh. They've all become so naughty,' she thought, a mix of embarrassment and arousal.

"Great, you're all set then," Chloe beamed.

Lana turned crimson, "When is it?"

"Right after lunch, won't take more than 2 or 3 hours," Chloe explained. Sensing her teacher's discomfort, she added, "It's super easy. I will guide you through the whole thing."

Lana nodded, seemingly assured. She glanced at the clock worriedly, "It is almost time for class. I need to let Stella know..."

The frail professor cleared his throat again, "Go ahead, Lana, I can do that for you."

"Thanks, Henry," she smiled at her colleague. He grinned back, happy to make her owe him one. "Let us go to class, Chloe," the teacher added, leaving with her naughty pupil.

~~~~~

Bus Ride

Back to the present, Lana sighs. 'Can't be helped. It's part of the Program. And Chloe needs me. Enough sulking, Lana! You are also supposed to chaperone them. Roger put you in charge.'

The naive teacher decides to check on her students. She didn't have a chance to talk to them before they took off.

She stands up, and her eyes meet Pringle's, the black driver. She notices that he is rubbing a huge bump on his jeans. Lana blushes and feels her cooch throb in response. 'It's not the time for that. Later,' she tells herself.

As she makes her way to the back of the small school bus. Pringle can't help but admire her large and shapely bubble butt swaying underneath the tiny pleated red skirt. He licks his lips. If only the dark-skinned man knew that the naughty teacher was wearing a butt plug in her tight virgin backdoor, things would've probably been different. But, alas.

Lana smiles at Chloe and Jen, who are dressed in the same cheerleader outfits as her. 'They look cute.' The naive teacher then analyzes the male members of the wrestling team.

There were 5 boys in total:

Andrew Winston-Phillips is the captain of the team and the wealthiest and most popular boy in school. He is blonde, tall, handsome, and is Chloe's boyfriend.

Then there was Timmy, a boy she only knew from the Art Club, along with two other boys from Class 2-A, Roger's class. The fourth 2-A teen on the Wrestling team is absent as he is sick.

Finally, Lackey #3, or L3 for short, is a boy with a large build who is in Mary's Class and is Zack's underling. Lana could not recall his name to save her life.

'Huh... What a weird Wrestling team,' the busty fiancee reflects. 'A better name would be "the small penis team",' she chuckles, recalling their boyhoods in her head. 'No boys here have a big pecker... the largest is Andrew, and he's barely bigger than Dens. That's a shame,' she shakes her head. 'Wait... I mean... peepee size doesn't matter,' she corrects herself.

She gets closer to them. 'But Dennis would fit right in!' She can't help but think with a tiny smirk. 'At least that means they're not a threat to me...' she glances at the dark-skinned driver, 'unlike a certain someone.'

Dismissing her thoughts, she sees Andrew sitting alone at the window while Chloe, his girlfriend, and Jen sit with the other boys in the last row. They are chatting enthusiastically.

"Why are you alone, Andrew?" She asks her student, who seems lost in thought. She insists, "Drew?"

The handsome boy whips his head to his teacher. "Oh, hi, Miss Cox. Sorry, I was distracted."

"How come?" The busty teacher-cheerleader asks, leaning on the empty seat next to him.

"Just planning the matches. Strategy is key," Drew says seriously. "I am their captain, after all."

Lana nods and is about to ask if he wants some company when Chloe interrupts them from two rows back.

"Miss Lana, come sit with us!" The blonde cheerleader motions to the teacher.

The gullible teacher glances at the lonely boy, who nods earnestly. She smiles at him, feeling a little sorry for him and all that he has been going through. 'His and Chloe's dynamic seems to have changed since Wednesday's class,' she reflects as she goes toward the students. 'Hopefully, they are okay.'

She passes by L3, also sitting alone. They lock eyes for a second, and the boy turns away, beet red.

'He's cute... how is he friends with Zack beats me,' she shrugs, continuing forward. She feels a hand firmly grab her butt for a hot second. 'Mmmm, I guess that's why.'

The teacher stops at the last row, noticing that there are only five seats, and all of them are taken. Jen is at the window, and Chloe seems to be sitting on the lap of a tall boy. Lana's eyes widen, but they seem to be behaving themselves.

"There does not seem to be a free space," the teacher says with a weak smile.

Jen stands up. The volleyball team's vice-captain is a brunette version of Chloe, with perky C-cups and a banging body. She is a lesbian, however, something that Lana learned the hard way. "Timmy, do you have space for Miss Lana?" she asks her classmate.

With a cheeky smirk, the boy grabs the teacher's hand and pulls it toward him. "You can sit here!"

"Eeepp!" Lana exclaims, losing her balance and falling tits first on top of Timmy. "Timothy!" She reprimands him. She turns and sits with her ample ass on his lap, feeling the pressure of her butt plug, Teddy, against her backhole.

The pervy teen and his friends laugh. He seems to be their leader, not Andrew.

"Sorry, Miss Lana, it's so fun to mess with you," Timmy admits.

The young teacher sighs, slightly frustrated, but decides against scolding the boy further.

Chloe explains how the matches will go to Lana, who pays half attention. You see, as the bus continues, the slightly bumpy rural road makes the teacher's bubble butt bounce on Timmy's crotch, drastically distracting her.

'Gosh, even with my skirt, I can feel the hard bump of his peen under my butt,' she thinks, absentmindedly rubbing her large posterior on his lap. 'Mmm... Teddy feels good inside me when I do that,' she mewls in her head.

Lana feels her student's hand rubbing her skirt-clad butt. She automatically wiggles her bum on his palm. Thinking she is encouraging him, Timmy slides his hand under her skirt and grabs a handful of naked assflesh.

"Ahhhh, I missed your ass, Miss Lana," the boy whispers in her ear. She moans softly, enjoying the lewd massage of his young manly hand and the sensation of her butt plug stimulating her tight hole. "Did you enjoy it when I played with it during the fire on Monday?"

She bites her bottom lips, "I did," she admits, almost whispering.

"Good, I jerked off a hundred times to you since then," Timmy says, bringing out his phone and showing her his lock screen. It is a large image of her naked ass and her cooch, only covered by golden-colored pasties.

"Goodness... that is so naughty..." she says breathlessly. 'I love that these naughty boys are so forward now... this was a crazy week, but it was for the best. I feel much closer, loved, and respected by the students. And Dens seems to be happy with it too,' she reflects.

"You're a hot slut, Miss Lana. You deserve all my cum," he whispers hornily in the teacher's ear, and she exhales, clearly aroused. "I need to see it," the little pervert says, lifting her skirt and exposing her bare ass and red thong to anyone who is watching.

"Timmy! Not in front of everyone," the curvy teacher protests weakly.

The student chuckles and points to Chloe, "Don't worry, they are busy."

Lana sees that Chloe is grinding on the tall boy's crotch while Jen is groping her captain's tits through her top.

The hot teacher feels a hand grab her left breast. "But I am not," the boy next to Timmy says. She purrs in approval.

"Good idea, Vic," Timmy says, slithering his naughty hand under her top and grabbing her braless bare right boob. "Fuck, your tits are awesome, Miss Lana."

She moans softly in response as her breasts are tender and throbbing for attention.

Seeing his buddy go further, Vic also slides under her red top, squeezing her left breast.

'Mmmm... feels nice being manhandled by them... or would it be boyhandled?' She giggles, enjoying them groping her boobflesh.

Suddenly, Chloe moans loudly, and they turn to see her grinding wildly on the tall boy's lap.

"Chlo! What the heck!" Andrew shouts, looking back at his girlfriend from his seat.

"Babe! You gonna come sit with us?" The blonde cheerleader asks with a sly smile.

"What? No... I... still have some planning to do," the captain replies, unusually frazzled. "What are YOU doing?" He demands.

Chloe giggles softly, "You're cute! I'm just motivating your teammates," she replies sultrily. "We need this win!"

A soft moan escapes her lips, and Andrew's eyes widen.

The blonde wrestler points at his girlfriend's crotch. "Wait... where is Ivan's hand!?"

"Mmm... don't worry about it..." Chloe replies breathlessly.

Lana sees that the tall boy's hand (apparently named Ivan) is inside Chloe's skirt, seemingly playing with her private parts in front of her boyfriend's eyes.

"Is h-he touching your kitty?" Andrew asks aghast, reminding the teacher of Nigel, the teen's weak-willed father.

"Oh, Drew, don't be silly," Chloe says playfully, lifting her skirt and revealing her tiny red thong to everyone. "See? His hand is just touching my panties," she purrs.

The captain of the wrestling team is speechless while his girlfriend's pussy gets rubbed in from of him by his teammate. Lana sees lots of feelings going through Andrew's face. Chloe openly moans with Ivan's touch.

Andrew's face turns red and a conflicted look flashes over it. Chloe moans erotically and sends him a kiss. The rich boy 'tisks' and turns back to his seat, clearly displeased.

The teacher feels herself getting extremely wet seeing her student's slutty display, she wiggles her majestic ass on Timothy's lap (feeling her anus squeeze Teddy), and he rewards her with a grope on her right breast. Vic follows through on her left, and she moans appreciatively.

"Chloe is such a hot bitch, Miss Lana," Tim whispers in her ear as his erection twitches against her butt. "Can I play with your pussy, too?"

"Mmm... better not," she replies, trying to maintain a semblance of control. "Maybe later..."

The boy groans, frustrated. "In that case, let me free myself," he says, removing the hand from her boob and unclasping his shorts. "Move up a bit..."

She does, and for a moment, the horny teacher thinks her student is going to free his weenie, but he only pulls his shorts down, keeping his gray boxers.

Timmy lifts her skirt and orders, "Sit back down." She does, and she feels her almost-naked ass rubbing against the soft fabric of his underwear. Her pussy and anus throb hungrily. The boy shimmies around and sandwiches his diminutive but rock-hard pecker between her mighty ass cheeks. "Ahhh, much better. You can keep grinding on me..." he says, a bit too commanding for her taste.

'Well... I might as well... just for a little bit. How did Chloe put it? It's our job to motivate the team,' she rationalizes as she rubs her bubble butt on his teen erection.

The boy's rod is pointing upwards, but the teacher can still feel it rubbing through his thin boxers against her thong-covered bum. Every rub causes her ass to clench around Teddy. It's driving her mad with lust.

Next to them, Vic gets up and stands in front of Lana. He continues massaging her boob with one hand while rubbing his boner, above his shorts, with the other. The teacher bites her lip, seeing her student being so crass about it in front of everyone.

'I barely even know him... them... and I'm letting one student freely play with my boobies while the other rubs his peen all over my naked bum... mmmm, it feels so nice. It's just motivational, I'm just doing what Chloe asked me to... part of the Program,' she tells herself as she thoroughly enjoys their molesting.

Surprising his innocent teacher, Vic lowers his bottom and frees his small 3-inch erection.

'Oh... it's so cute! Small penis team indeed,' she chuckles. 'Is he going to spurt his seed on me?' She thinks, licking her lips.

"Please, Miss Lana... suck it..." the boy begs.

The turned-on busty fiancee gasps softly, but seeing the pleading look on her student's face, she decides to help him out.