Naive Teacher in Winston
Exhibitionist & Voyeur Story

Naive Teacher in Winston

by Potatohead42 16 min read 4.7 (19,300 views)
teacher naive corruption exhibitionism teasing groping virgin cheating
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Lunch shame and AV Club's naughty lasso.

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 2024, so any correlations with real life are mere coincidences.

This chapter contains the afternoon of Day 16 (Tuesday). The morning was recounted on Ch 14a, and the night will be on Ch 14c. Thanks for the support!

Enjoy the read,

~ Potato Head

~~~~~~~~~~~~~~~~~~~~~~

Previously on...

Potato Note: reminding y'all of some relevant storylines and threads from the last chapters!

* Currently: Day 16, Tuesday. Lana and Dennis' third week in Winston.

** Wedding day 40 (Friday); Winston-Fest days 34 and 35; Winston week + Fair days 29 to 33;

** Lana's fame and notoriety in Winston is growing, and she is getting recognized quite often by the townsfolk.

Important Topics

*

Mary's Influence

- Broke down some of Lana's barriers, she will slowly stop doubting herself too much and try harder to embrace things. Her restraints and morals are crumbling.

- Mary is planning to overthrow Bill and take over as Principal. She needs Lana's help; don't let Bill get suspicious.

- Mary wants to turn Lana into a Blowjob Queen -- asks others to say she needs to improve; keep practicing (competitive side), even if she gets good.

- Mary said Dennis was a cuck. Lana thinks he is a Voyeur who likes to see her playing around, teasing, and showing off her sexy body. She decided to ask one of Dennis' friends about it.

*

Incentive Program

- New program where she gets rewarded by bonding and physically encouraging her students. New school uniform: pick a fresh blouse, skirt, and panties daily.

- Principal Bill revealed to the whole school that the newbie teacher was enrolled in the program. Everyone became more daring and naughty with her now.

- Dennis encouraged Lana to ditch a bra with her new uniform due to a misunderstanding.

- Due to Lana rushing out of the Bio Supplement shoot, she is currently without panties.

*

Dennis' Medical Orders

- He is not allowed to cum until the spermiogram exam on Friday. No relations, no fooling around. Dr. Hardik emphasized he needs to avoid erections at all costs.

- Lana can still send him photos, but he can't see them until after the exam. He agreed that she can send pics of her bare boobs.

- Lana is saving what she has done for the weekend; she is convinced Dennis wants to hear all about them. Anita, Lana's mother, said it was okay to fool around if Dennis can't perform.

*

Dennis' New Rival

- He is in charge of a new team. Their leader, Uwe, moved to Winston and will work locally. Dennis needs everything to remain peachy to earn a huge promotion.

- Uwe is secretly blackmailing Dennis with photos of Lana's wardrobe malfunction during a Zoom meeting and from her urinating in the bushes (her vagina on full display). He also has unrevealed pics he is saving for another occasion.

- Dennis asked Lana to be friendly with Uwe and motivate him. She agreed to go for lunch at some point and show him a good time around town.

- Lana accidentally showed herself naked in a Zoom meeting again, giving Uwe more ammunition for the blackmail. Uwe is also putting naked photos of Lana in the kitchen at work. They are cropped to hide the fact that it's Lana.

The Day

- Morning: Biology Supplement Shoot (w/ Pietro and Roger)

- Afternoon: Homeroom, AV Club

- Night: Simon Tutoring, Pietro and Simon Dinner

This is where our story resumes...

~~~~~~~

Prologue

~~~~~~~

Dennis and Uwe

The out-of-shape, 6'2 tall man walks down the corridor. He stops at the open entrance to the office kitchen. He spots some pornographic images on the team's corkboard. The ginger man sighs.

"Denny! I have your pills!" a peppy voice says.

The boyishly handsome man turns to see his pretty blonde coworker strutting toward him. He greets, "Hi, Cynthia-guh!"

The ginger-haired man is interrupted by Cynthia, who throws herself at him and squeezes his life out. "Gaaahh! You look so handsome today, Denny!" she says and kisses his cheek.

"Ah... thanks," he replies, blushing. "So, how's it going?"

"Better now," the blonde says flirtatiously. She bounces a little, causing her small perky tits to jiggle. Dennis almost chokes.

"Guh... good, good," he recovers, admiring her incredibly tight body. He loves his wife dearly, but Cynthia is a total knockout, capable of causing even the limpest man to get rock-hard. He chuckles at that analogy. "Uhhh... so, what can I do for you?"

"Can't I just come to say hi to my favorite person in the office?" she asks innocently.

"What about Paul? Your

boyfriend

..." Dennis emphasizes as if she had forgotten.

"Pff... he's boring," the blonde says. "I like you more," she adds, biting her lip teasingly.

Dennis quickly glances around to make sure nobody is watching. "That's good," he grins quietly.

Cynthia holds his hand and shoves two pills on it, "For your headaches."

"Ah!" The ginger man says. He has been suffering from migraines lately, but he doesn't want to worry his fiancee about it. '

Yet. She's so busy at work and taking care of everything... I don't want to burden her with one more thing...

' he justifies in his head.

He smiles at his blonde coworker, "Thanks, Cynths, I owe you one."

"Anything for you, handsome," she says, touching his cheek. "I have to go now, the boss calls," she pouts.

Before Dennis can react, she gets on her tippy toes and gives him a quick peck on the lips. He gasps. Cynthia giggles and bounces away, her tight ass swaying in her booty-hugging pencil skirt. She turns midway to make sure he's watching, winks, and continues on her way.

"Darn... she's gonna be the death of me..." the foolish man mumbles, adjusting his pants.

Dennis glances at the kitchen and sighs once more, remembering what he was here to do. He walks to the board and glances at the three new photos: a closeup of enormous boobs, a bottomless woman in the bushes, and a strange one of the same woman walking through a park. This last picture is cropped, so you can only see her from the legs down.

'

Looks like a park in Winston... she must be local...

' he ponders.

"She's hot," he mutters, admiring the pictures. '

Huh... she reminds me of Lana... weird... nah, that's crazy,

' he reflects.

"Dude, you like it?" Justin asks from the door. He is a classic jock, also with ginger hair.

Dennis turns, flushed. "Justin... stop putting these up!"

"Just sharing some nice photos with the world," the jock grins.

"Did Uwe put you up to this?" Dennis furrows his brow.

Justin shrugs, feigning innocence. "He has a bunch of them, so he asked me to place some here so everyone can admire this hottie."

"Whatever. Stop it, please," Dennis says, ripping the pictures and throwing them in the paper recycling bin.

Justin laughs, "You're no fun, dude!"

Dennis gives him a forced smile and leaves, going to a meeting. He has a dreaded 1-on-1 with Uwe, his new direct report.

He enters the meeting room, and Uwe is already there, waiting for his new boss. The ash-blonde man is pale and ugly, with yellow teeth and a splotchy face.

Dennis first notices Uwe's unmistakable smell: sweaty and damp with undertones of something a bit woody or nutty. It's odd and unpleasant. The ginger man grimaces.

"Hello, Mr. Penis! Sorry... bad habits. Dennis," Uwe corrects himself.

Dennis sighs. Every encounter increases his dislike for the gross man. "Hi, let's get this over with," he says, sitting across from his subordinate.

"Right to business? I like that!" Uwe grins. He rifles through his pocket and brings out his phone. He unlocks it and hands it to Dennis, "Here."

Dennis grabs the phone and stares at the picture. His heart skips a beat. On the screen is his fiancee's boobs spilling out of her nightgown.

"Guh!" the bumbling husband-to-be chokes.

Uwe snickers, "There's more, swipe to the right..."

Picture by picture, Dennis watches a breakdown of everything that happened that morning with Lana in the Zoom meeting.

"W-when... was this?" the ginger man asks, his breath ragged. '

This bastard tricked her... what the heck does he want now? Darn...

' he reflects, upset.

Uwe snickers again, "This morning."

Dennis nods and closes the photo to the gallery. He quickly taps on all of them and presses delete. The confirmation dialogue appears.

Uwe's heart races, and he panics; he can't let Penis delete the pictures. He has to think fast. The ugly man was so confident in his plan that he forgot to make a backup. "Hah! What do you think you're doing? I have dozens of copies!" he bluffs.

"Che..." Dennis grumbles, putting the phone aside, "What do you want?"

"What don't I want?" The ash-blonde bastard grins. "Maybe I will slow my work down even more... and send these photos to everyone..." he says tauntingly.

Dennis is livid. '

I can't let that happen... Lana will be destroyed, and Mr. Winston-Phillips will fire me... fudge, fudge, fudge...

' he freaks out.

"I see you understand the gravity of your situation, Dennis," Uwe provokes him. "So, when is my date with your fiancee?"

"Uhhh..." the ginger man mutters. He has not figured that out. He has been hoping that he could delay it and Uwe would simply forget about it.

The skeezy ugly man smiles, "Lunch. Tomorrow."

"You can't!" Dennis retorts. "I mean... I don't know if Lana can do it..."

"I am sure she can," Uwe smirks vilely. He yawns and stretches his arms, "I don't feel like working today... maybe Justin will be interested in checking out some pics at the park..."

"N-no! I'll confirm with Lana," Dennis says anxiously. The park reference is lost on him. '

I need to go ahead with this and figure out a way to stop him... fudge!'

The ash-blonde man grins, "I'm sure you'll manage. And... I want a kiss from her."

Dennis nods meekly, "Sure..."

Uwe continues, "And ask her to be extra nice to me...."

Dennis nods. '

I can just agree to all his demands now and figure a way out later... heck, Lana doesn't even need to do any of it. Just go for lunch with this bastard,

' he grins to himself.

"And tell your fiancee to not wear panties!" the gross man concludes.

"Sure..." Dennis agrees without thinking. "Wait, what?"

Uwe smirks, "No panties! I want her commando for our date."

'

This bastard is out of his mind! Lana will get a kick out of this... how crazy is he? Hah!

' Dennis laughs in his head. "Sure, sure..." he agrees. He thinks of something, "One condition."

"Go ahead," Uwe says, making a dismissive gesture.

"You cannot tell Lana about any of this," the ginger man says.

"Oh?!" the ash-blonde asshole exclaims with surprise.

Dennis explains, "She thinks she is just going for lunch with my new coworker. To show him the city and the famous Winston hospitality."

"Hmmm..." Uwe ponders. He reasons that his plan can still work. It only depends on how gullible Penis's wife is. "Deal! I'll see your fiancee tomorrow," he gives Dennis a slimy grin.

~~~~~~~

Day 16 --Afternoon

~~~~~~~

Lunch -- School

The busty 5'3 teacher is outside the Art Club when her phone beeps. Her soft hands fish her device from her purse. The 27-year-old shuffles her ample bottom as she unlocks the screen. Her green eyes read the message from her loving fiancee.

* Dennis:

Can you go for lunch with Uwe tomorrow?

Lana Cox cocks her head slightly. She adjusts her medium-light brown hair and straightens her back. She is dressed in a tight white skirt, an opaque gray sleeveless blouse, and tan flats. Her voluptuous and toned body is a marvelous sight.

Message -- Dens <3

---------------------------------

* Dennis:

Can you go for lunch with Uwe tomorrow?

* Lana:

I guess... why the rush, Dens?

* Dennis:

The conversation with the president this morning. Need to figure this out

* Lana:

I see. Yes, I can help you! <3

* Dennis:

Thanks, babe. Also, won't believe this...

* Lana:

What?

* Dennis:

Uwe asked you not to wear any panties! The audacity!

---------------------------------

Lana puts her hand to her chin, contemplative, '

That's what Bill said too... to help Dens. He is probably right...

'

---------------------------------

* Lana:

He said that? Wow

* Dennis:

Don't worry, I will just tell him you did. He will never know

* Lana:

I could err on the safe side...

* Dennis:

And, please be extra nice to him... my job is at risk

* Lana:

Of course, silly carrot! I will make sure of that.

* Dennis:

Thanks, babe

* Lana:

I'd do anything to help you. *smile*

* Dennis:

You're the best

* Lana:

*giggles* Talk tonight? I need to meet Mary for lunch

* Dennis:

Sure! Love you *kissy face*

* Lana:

Love you too *heart*

---------------------------------

'

Dens will see, I will be super good to Uwe. Yes, he is gross and causing trouble to Dens, but it's my duty to help my fiancee however I can. Even if it involves that foul man,

' she concludes, proud of herself.

The buxom teacher's phone beeps again, and she glances at it, thinking it's Dennis.

Message -- Cox Friends

---------------------------------

* PB-Justin:

Sup, Cox! Where's our daily selfie?

* Lana:

Good afternoon to you too, Justin! *laugh*

* PB-Justin:

I'm bored in the toilet and thought I could rub one out to you really quick

* Lana:

Justin!

* PB-Justin:

You love it sexy

* Lana:

*blushing*

* PB-Justin:

So? *eggplant*

* Lana:

I will see if I can do it ASAP.

* PB-Justin:

Challenge: get someone else to take it and have them participate somehow

* Lana:

I'm not sure I can find someone...

* PB-Justin:

Just get a student, they'll be happy

* Lana:

I will try. *grimace*

* PB-Justin:

I'll be waiting *wink*

---------------------------------

'

Justin is so crass and naughty... I guess I can get a student I trust to do it...

' she ponders. The future-wife's ability to momentarily block any predicaments from her mind and bounce to another subject is extraordinary.

As if by magic, Lana spots Justin's brother coming out of the Staff Room.

"Greggy!" she calls him. "I need a favor," she says, approaching the chubby boy. The cherub-faced teen is nothing like his jock brother. Greg is an unpopular boy who is short, fat, and is constantly being bullied.

"H-hi, Miss Lana!" the student says, wiping sweat off his brow. The sexy teacher has him highly intimidated. "How can I help you?"

She promptly kisses his round cheek. "Did you learn your lesson yesterday? Stop mixing yourself with Zack Archer and his underlings," she lectures.

Greg's eyes get watery. "I did..."

"They are bad news," she continues.

The chubby student nods, "I will try to keep away from them. But maybe things are changing," he says with a hint of hope.

"Really?" she exclaims, pleasantly surprised.

He nods vehemently, "They are treating me really well today!"

"Good job, Greggy. Be careful, I worry about you," she says, caressing his cheek. "You are my school boyfriend, after all," she giggles.

"Thanks, Miss Lana," he replies with a big, dumb smile.

"About the favor..." she glances around, "Come with me," she says, grabbing his clammy hand and dragging him after her. She guides him to the girl's restroom. He audibly gulps as they enter.

"W-what are we... doing here?!?" he says, scared.

She smiles lovingly at him. "Please, take a picture for me," she says, handing him her phone.

Lana feels completely comfortable with Greg. She feels he is like her younger brother and that she has all the power over him. '

He's like my puppy,

' she giggles in her head.

"O-okay..." the fat boy clumsily says as he fiddles with his teacher's phone.

'

Hmm... what should I do? Well, I guess Dens gave me permission to take photos of my boobies. That sounds

reasonable

,

' she reflects.

To Greg's surprise, she opens her gray blouse and exposes her bare breasts to her student. The wife-to-be large pink areolas and small rosy nipples are a sight to behold.

"Uhh...." the chubby teen mutters, hypnotized.

She giggles at him. "Greggy, the photo..." she reminds him.

"Uh... right..." he says and awkwardly takes a picture. He turns to show her.

"Hmm..." she mutters. '

Justin did say to get the person to participate....

' she considers. "Can you use your other hand to support my breast?" she asks sweetly.

"T-touch your tit?!" the fat boy blurts, his eyes almost popping out. This is Greg's true self without his bullies to show off to.

Lana giggles, "You are too cute. Yes, hold my breast from the bottom," she says patiently.

Nodding, the blubbery boy places his sweaty right palm under her bare left boob. Both moan softly as the contact happens.

"Mmm... feels nice," she says lustfully.

Greg takes a picture and shows it to his teacher.

"That looks great. Thanks... Big G," she says, her voice full of honey.

The pitiful teen turns crimson. "Uhh... welcome..." he squeaks.

"Will you be at the AV Club later?" Lana asks, and he nods enthusiastically. She giggles and pecks his chubby lips. "See you later then," she says, exiting the restroom.

'

I'm glad Greggy seems to be getting better. All I want is for him to turn out well and be happy,

' she thinks proudly. '

Hopefully Justin and the the Cox Friends like it,

' she reflects, sending them the picture.

---------------------------------

* Lana:

Here is it! Your baby brother helped me, Justin! *laugh*

---------------------------------

'

I bet he didn't expect the student to be Greg!

' she giggles, feeling kinda mischievous.

She hears a girly scream coming from the girls' bathroom. '

That must've been someone seeing Greg! Oops,

' she giggles.

The busty teacher continues down the corridor when she spots Flora by the stairs, walking to the library. The librarian sees her friend and waves.

Lana's phone vibrates like crazy, and she glances at the screen, reading the guys' reactions: "Fuck me sideways!" "Superb, Lanita! Save me some!" "My bro is so lucky! I'll do the same next time! I'm gonna go nut."

The horny teacher smiles friskily, feeling a pang on her cooch.

~~~

"Lana! I have some good news," Flora says as her colleague gets to the stairs. She is in her early 30s, has curly dark hair, and wears rimmed glasses. She always sports a sexy librarian look.

"Oooh! Do tell," the busty teacher smiles at her friend.

"I think I'm dating!" the librarian announces. And jumps excitedly.

Lana bounces with her, "That is exciting! Who is it?" Her ample braless breasts sway enticingly. Flora can't help but stare at them.

"Jen! We made out and fucked yesterday. It was amazing!" the bisexual woman reveals.

The brunette teacher smiles, "I am so happy for both of you!"

"I never met someone who could squirt before... it was delightful," Flora discloses.

"Ohh..." Lana blushes. Something comes to her mind. She lowers her voice, "Can you... date a student? Is it not wrong?"

The librarian giggles, "I don't think so! I never saw any rules about that. I can ask Stella."

Lana nods, "Thanks... l-let me know..."

Flora squints, "Is there any student you want to date?" She grabs Lana's oversized tit, "You can tell me..."

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