Naive Teacher in Winston Ch. 14a

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"You can let go now. We're here," he grins.

"*Gasp*!" She quickly sits back in place and looks around worriedly. "Jack! You should have told me we arrived at school. Someone could have seen me!"

The fat man grins, "You were having too much fun, I didn't want to interrupt."

She sighs and shakes her head, a little vexed. "Thanks for the ride, I enjoyed it," she says, opening the door.

"My pleasure," he winks, and his thick dick bobs in response. Her eyes widen, and she glances around.

"I should go. Thanks again, Jack. Bye," she says, exiting the car. He smacks her ass one more time. She can't help but yelp. She turns and smiles back at him.

"See you later, naughty teacher!" Jack waves. As she walks away from the car, he feels compelled to admire her round sashaying butt.

The overweight man smiles and picks up his phone to inform the Winston Secret Chat Group about "Dennis' condition".

As Lana crosses the school gate, her nipples are throbbing, and she is achingly hot and bothered.

~~~~~~~

Early Morning -- School

The naughty teacher struts across the schoolyard, every teenage eye on her.

A boy whistles, causing her to blush, self-conscious of her state. She continues with determination.

The teacher's tight white skirt accentuates all her voluptuous curves, emphasizing her toned legs and ample bottoms. The skirt ends only a palm below her buttocks, leaving her creamy legs on display for all the hungry teenagers. As she walks, her ass wobbles enticingly.

"Nice ass, Miss Lana!" Timmy says. He's a butt-obsessed boy from Class 2-A and a member of the Art Club and the Wrestling team.

Lana inhales and feels her pussy clench.

The teacher's gray sleeveless blouse, covering her giant orbs, is quite a sight to the students. It's apparent that the busty educator is not wearing a bra under her top. Her body movement causes the weight of her melons to bounce and sway with each step.

"Look at her boobs..." Timmy's friend says, making a pointy gesture with his finger.

"I think Miss Cox is not wearing a bra!" another boy points out.

Lana turns even redder, somehow causing her nipples to get even stiffer.

"Fuck... I wish I had classes with her," a tall boy from the Wrestling team says.

Another one agrees, "Imma jerk off to her so much today!"

'He is? Gosh...' she thinks, her coochie throbbing.

A few more whistles and catcalls later, Lana safely enters the school.

'Wow... this was so intense... every student is much more forward now... I wonder if they will get used to my attire,' she thinks, rubbing her thighs, 'Or if it'll only get worse... imagine what they would do to me if we were alone... would they ravage me? Oh, my...' she swallows, her nipples burning up.

"Morning, Miss Lana," Greg Zimmer says. He is a short, round-faced, obese boy from class 2-C who is constantly bullied by his classmates. The pitiful boy seems to have been waiting for her.

The teacher smiles at her 'School Boyfriend'. "Morning, Greggy," she says endearingly. She looks around and sees other students staring. "I mean, Big G," she corrects, remembering his requested nickname. She leans over and smooches his chubby lips. "My boyfriend..." she announces, playing it up.

Greg smiles dumbly, but someone suddenly pushes him to the side.

"Damn, Fatso, you're so lucky your girl has giant udders," Zack Archer smiles. He is the school bully with a large head, medium height, and build. "Hey, Miss C!"

His three underlings smirk behind him.

"Hello, Zack," the teacher greets coldly. "I thought we agreed to stop the bullying?"

"Well, I didn't technically lose the bet," the shit-head grins. "So I'm free to keep doing it," he adds. Zack reaches out and squeezes the teacher's left tit.

"Eeep!" she yelps and slaps his gropey hand away. "Stop that. Do you want me to tell Mary?"

"Che..." he grumbles and pushes Greg again as a payback. "No bra," he tells his underlings.

"See you later, Big G," the teacher says, kissing the sad, round student on the cheek.

Greg smiles dumbly again, "Bye, Miss Lana!" And wobbles away.

Lana scowls at Zack as she passes. 'Gosh, these boys drive me mad... why can't they leave poor Greggy alone?' She reflects.

To her surprise, L1, one of the underlings, lifts her skirt and bunches the garment around her waist.

"Eeeekk!" the teacher yelps, turning around to confront her pranksters. "What the heck!"

All the students around start whistling and shouting obscenities at her.

"Nice panties!" "What an ass!" "She's thicc!" "Sluuuut!" "She's a fucktoy!" "Go, Miss C!" "So phat!" "Let me fuck you!"

She turns crimson and feels a twang in her coochie. She stares in shock at Zack and his underlings. The gang starts laughing at her predicament.

"We got you good, Miss C!" Zack high-fives L1.

The curvy fiancee struggles to pull down her tight skirt, giving all the students a good eyeful of her fucktastic butt and red cheeky panties. She finally manages and exhales with relief.

"I will make you pay, insolent boys," she huffs at them, extremely upset.

She bolts up the stairs, her heart thumping. The mischievous teens were still laughing behind her.

'Rahhhh, the audacity... gee... I get so upset at them. They are so mean and have no respect. I've been weak to stop them until now, but I need to establish clear boundaries. Like Mary does,' she considers. 'You got this, Lana. Zack and those demons can't keep getting away with it!'

The busty wife-to-be realizes her panties are soaked, and her nipples are aching.

'Goodness... I got so hot... did being humiliated turn me on? No... it can't be. That's crazy. This is just my body's reaction, probably from Jack earlier in the car. Yes, it must be. Right?' She ponders as a poster catches her attention.

At the top of the stairs, there's a new poster.

"WinsTok - Available today! Download now" and a huge QR code underneath.

'Huh, strange. I wonder what this is... An app, maybe? I should ask, she makes a mental note.

Lana walks to the Staff Room.

~~~

Staff Room

The teacher's room is empty, except for Lana's best friend.

"Morning, bff!" Mary greets her. "I was hoping to catch you."

Mary Hunter is a stunning 36-year-old blonde with fake C-cups, slightly tanned skin, a small nose, and full, pouty lips. She is the pornographic dream of a teen boy.

"Hi, bestie. I had a wild morning," Lana grins at her friend.

"I'm sorry, babe. We can catch up later. I need to go soon," the bombshell blonde says.

Lana is a tad disappointed, "Ah... okay..."

"I wanted to mention something... delicate," Mary says, sitting down.

The busty brunette sits and cocks her head, "What is it?"

The milf teacher seems unusually nervous. "Erm... about the things we discussed regarding Bill..." Mary stammers and Lana nods. "Please, bff, I need your full discretion."

"Of course," the naive teacher replies.

"Neat. So help Bill with anything for now," the blonde says. "I can't emphasize it enough. Do whatever he asks. He can't suspect anything is out of the ordinary."

"You can count on me. I have your back, bestie," Lana assures her.

"Yay!" Mary squeals and kisses Lana on the lips. The brunette teacher is dumbstruck. The blonde continues, "Thank you so much. I'm super nervous; this could backfire badly," Mary says, frowning. "Let's meet for lunch at the caf to discuss the plan."

The buxom brunette says quietly, "That sounds good. See you there."

"See you, precious!" Mary says, sends her a kiss, and rushes out of the room.

"Wow..." Lana mutters, 'I can't believe Mary kissed me on the lips... I guess it was just a spur-of-the-moment thing... mmm... it felt nice...' she thinks, feeling horny.

She drops her things and tidies her desk a little.

'Hopefully, I don't run into Bill this morning; trying to hide things from him will be awkward. I'm not very good at that. If I do, I need to remember what Mary asked and play along for now,' she sighs, a tad worried.

'Stella booked the Art room for the Biology supplement. It's almost time, so I'd better get there early,' she decides, leaving the room.

She's feeling a little uneasy, 'I'm glad it's just the bodies chapters.'

~~~

As she exits, she spots Evelyn, her student, holding a few books by the stairs.

"Morning, Evie!" the teacher greets her happily. Evie is her favorite female student.

"Ah, morning, Miss Lana!" the raven-haired girl greets back. She is a little pixie with small breasts and a petite frame. "I have some questions about class. Do you have a minute?" She looks worried.

"For you, all the time in the world," Lana says with a loving smile.

She walks toward her pupil at the top of the stairs, and they chat about the lessons for a couple of minutes. With a large smile, Evie thanks her teacher and bounces to the library.

Lana hears a clicking sound, and she looks behind her. A few steps below, a boy is taking photos under her skirt.

"What are you doing?" she asks, turning red. Her cooch clenches.

The teen smirks at her, "Just grabbing an upskirt photo for later," he says, running down the stairs.

"Gosh..." she mutters. 'I wonder if he's going to jerk off to me?' she thinks, her twat heating up.

Another student passes by. "Can you lift your skirt, Miss Cox? I heard you gave everyone a good show a few minutes ago," he asks cheekily.

"What? Eh.... No..." she says sheepishly, taken aback. The boy 'tisks' and leaves.

A girl from the volleyball team is coming in the opposite direction and squeezes the bottom of the teacher's buttocks. "Nice ass, Miss C," she says.

Her teammate interjects, "I want to try it too!" the second girl says, also squeezing the teacher's ass.

"Amazing, right?" the first athlete says.

Lana is momentarily stunned by the girl's advances as she feels her sex twitch hungrily. She shakes her head. "Uh... thanks, girls. I should go," she hurriedly bolts toward the right corridor.

"Boooo... no fun!" the second young lady says.

Her heart thumps as she marches down the corridor. She stops and leans on the wall. 'My, my... they are relentless...' she thinks, almost out of breath.

The busty teacher realizes she has her hand on another WinsTok poster. She shrugs and goes toward the Art Club room.

~~~~~~~

Morning - School

Bill

The innocent horny teacher is face-to-face with Principal Bill.

William 'Bill' Winston-Phillips is a big man in his late 60s. He is tall, broad, husky, and extremely lecherous. He runs entirely amok regarding women as his family and his brother, Dick, own the town.

"Morning, buttercup!" the Principal beams.

Lana is taken aback by his presence. "Oh... h-hi, Bill," she croaks. 'N-no way... I was hoping to not run into him today, never mind this soon!' She thinks, exasperated.

Bill chuckles at her surprise, "You must be wondering why I'm here?" She nods. "Well, this is your thing, so I won't interject too much, doll."

"Thanks?" she says, a bit confused. 'What does he mean, "too much"?' She ponders. Lana spots Pietro working on his equipment at the side of the room. They wave to each other.

The burly Principal gets close to her and says quietly, "How is the butt plug? Did you try? Does it have a name?"

The busty fiancee turns red, "Ah... uhm... T-Teddy..." she stammers.

The older man chuckles again, "Interesting name. Why?"

"Erm... I wanted to name it something cute, like a teddy bear..." she says, embarrassed.

"I guess it works," the broad Principal says. "Did you use Teddy on your own?"

"I did..." she admits sheepishly, "I liked it." She thinks apprehensively, 'I need to keep the conversation away from Mary... Bill can't suspect a thing.'

"Great! Keep on with that," he says, and she nods. "And I see you're not wearing a bra," Bill says, leaning in until he is a couple inches from her ample bosom. He inhales, smiles, and straightens up. "Well done," he says and pats her head.

The teacher mewls, happy to be praised. 'Hmm... I wonder why he didn't touch me... wait what am I thinking? Why am I disappointed by that? Ugh...' she shakes her head.

"Anyway," Bill says, swaying back and forth. "The reason I'm here. I discussed with the Board."

"The School Board?" Lana blurts out, her heart beating fast. 'Does he know?!' She panics.

"Precisely. This is one of the most important moments of the year for you," the big man starts discoursing as he slowly moves around the room. "I know this came from your own initiative, but the Board is pleased beyond belief," the hulking Principal states. "What you do here today will weigh heavily on your future job and promotions. I am talking about the permanent teaching role," he looks at her solemnly.

"Oh..." she mutters and nods, trying to transmit confidence. 'Phew, it's not related to Mary,' she breathes.

Bill smiles. "Depending on the results, I would feel confident nominating you for the 'Educator of the Year' award."

"Gosh, that is amazing," the naive teacher says.

"Indeed, buttercup. Indeed," the husky old man agrees. "So the Board discussed, and we would like to propose something for today. You don't have to accept, but keep in mind what I just said."

Lana nods assertively, "I will. What is it?"

"We would like to create supplements for future materials, too," the Principal says.

"I see.... Anything specific?" she asks, sensing something terrible is coming.

"Yes, we would like to cover the remainder of this year," he says nonchalantly.

The curvy fiancee gasps, realizing the implications of what he means. 'Maybe I misunderstood...', she reflects. She stammers, "Even... the 'intercourse' chapter?"

"Especially that one. It's not every day we have this golden opportunity with a talented photographer like Mr. Romano," Bill says, gesturing at Pietro.

"But..." Lana protests weakly. Mary's voice echoes in her mind, "Do whatever he asks. He can't suspect anything is out of the ordinary."

"Remember the detention yesterday? You were reasonable and followed the Program. It was rewarding for everyone. That's how you have to proceed moving forward," the Principal argues.

Lana knows she is in a pickle. She shifts nervously, "I am not sure how to do this..."

"It's just simulation. It'll be easy," Bill assures her. "Nobody will know. Your face will be cut off."

'Gosh... I don't think I have much of a choice... Mary asked me to do this. If I go against Bill, he might ask questions... no... that's risky. He needs to stay oblivious. I need to protect Mary. And Dens... well... he did tell me to embrace the Program so we can both get promoted. I will message him to check...' the teacher processes, her heart thumping. Her cooch, however, is twitching with excitement.

"Goodness me... I guess I will do it," she says, unsure.

"Perfect!" Bill says, giving Pietro a thumbs-up. "I'll leave it up to your and Mr. Romano's discretion on how to best approach the material. Please listen to him, as he is a professional."

"I will do my best," Lana says timidly.

The hulking man smiles, "I know you will make the Board and me proud. Mayor Dick will also be pleased. You're an inspiration to Winston."

The buxom brunette smiles, all warm and fuzzy by his praise, 'I guess it's not all that bad...'. "Thanks, Bill," she says sheepishly.

"Before I go, I have another quick topic," the Principal says ominously.

"Oh..." Lana mutters. 'Gosh, I hope it's not about Mary...'

"I heard from Dick that Dennis is having trouble getting his new team members to work productively." Bill puts his hand to his chin, "He has a weird name... German, I think?"

"Uwe?" the naive fiancee asks.

The large old man claps his hands, "That's it!"

Lana exhales, relieved that she seems to be again in the clear. 'Wait... why is Bill interested in Uwe?' She reflects on him, 'I don't like this man. He barely arrived, and he's causing all sorts of problems to my Dens...'

"So, I discussed this with the Town Council last night and we are all greatly concerned," Bill continues.

"Gee..." she reacts.

The Principal's expression is grave, "We are convinced that Uwe needs to be integrated properly into Winston's customs, or things could get bad."

Lana's eyes widen, "For Dennis?"

Bill nods, "Yes. We need him to prove his worth here -- like you have."

"Oh!" the innocent wife-to-be exclaims. "Dens asked me to take Uwe to lunch and show him a good time," she reveals. "I would love it if this could help Dens. What do you think?"

"Lunch, huh?" Bill ponders. "That's a start. Dennis might be onto something."

"He is?" she asks, not entirely following. 'My carrot is so smart!' She thinks proudly.

"Oh, yes, peach. You would be a great person to motivate Uwe onto the right track. Especially if you use your new Incentive Program skills," the old Principal grins.

"The Program? But that is for school," Lana says. She can feel her body heating up for some reason.

Bill shrugs, "Well, why not? Treat Uwe as a student."

"Uhh..." she thinks back to the conversation she had with her fiancee. "He does seem a bit childish..."

"See? Get close to him. Bond. You know how! Anything reasonable is game. Maybe skip the underwear, like today," the Principal winks.

"I have panties on!" the busty teacher points out. Bill laughs. "Do you think that would work?"

"Yes. One hundred percent," the large man assures her. "This man will be an easy catch for you, doll. He won't even know what hit him!" He winks again.

She blushes and agrees, "I guess if it is to help Dennis..." Although she doesn't really understand what she is agreeing to. She can't help but think, 'I will help, even though Uwe seems like a revolting and wicked man...'

Bill is pleased and announces that he has to go. He gives Lana a quick, innocent peck on her lips and fleetingly squeezes her braless melons.

As she stares at her boss leaving, she can't help but feel disappointed by his goodbye.

~~~

* Ring, ring! Ring, ring! *

The naive fiancee glances at her phone, 'Ah, it's Dens!' She thinks happily.

++++

Call -- Dens <3

L: "Hi, hun!"

D: "Hey, babe. You won't believe what happened!"

L: "Tell me!"

D: "So the guys put some naked photos on the communal kitchen board!"

L: "What?! Of whom?"

D: "No idea! It was just some boobies and close-ups of a vajayjay!"

L: "Goodness..."

D: "There was even one of them where the woman was peeing!"

L: "Ew, gross!"

D: "I know, right? I removed it right away. Before Lucius or any superior saw it."

L: "Good, good."

D: "But I think they will do it again."

L: "Those boys are incorrigible. Was it Uwe?"

D: "Yeah, he got Paul and Justin to tag along. I guess he is trying to fit in. How did you know?"

L: "Ah, Principal Bill mentioned he is causing trouble. Apparently, Dick is unhappy."

D: "Oh, darn... I know."

L: "You do?"

D: "Yeah, Mr. Winston-Phillips talked to me this morning. Asked me to deal with him..."

L: "Gosh...

D: "There was an insinuated 'or else' there too. I better figure something out."

L: "I can help! With the lunch date."

D: "Ah, yeah... that. I almost forgot. And it's not a date. But yeah, that will help. Let's talk tonight then..."

L: "Of course, Dens. And I almost forgot, need to ask you something."

D: "What is it baby?"

L: "I am a little nervous, Bill talked to the Board..."