Naive Teacher in Winston Ch. 13b

"Yes, he really seemed to get a kick out of me teasing the waiter. He even wants us to do it again." - the beautiful brunette says. Mary chuckles.

"Precious, he is a voyeur and a cuck." - the blonde teacher states.

"You think so?" - Lana asks automatically.

"He encourages you and gets turned on seeing you show lots of skin. He loves it when you openly tease for him to watch." - Mary elaborates.

"That is true..." - the future-wife agrees.

"Maybe that's why he wasn't so into Saturday night... you didn't stimulate his mind enough. You needed to tease him about the Horn Test or the beach." - the Hunter woman states.

"Oh..." - Lana mutters, realizing Mary might be correct.

"Try to stay focused on his kinky side. Bring the subject up slowly and play with him when you're alone or when he's watching." - the blonde bombshell suggests.

"I never thought about it like that. Wow, bestie. You are a genius!" - the brunette teacher exclaims.

"Thanks. Maybe I should be the one teaching sex ed!" - Mary says.

"You should!" - Lana agrees, and they both laugh.

They finish their meals and clean up the desk.

~~~

"So how are you feeling about it?" - the milf teacher asks.

"I think I can do it. But I am nervous. Will Dens and I be the same after this, you know?" - Lana questions, worriedly biting her lip.

Mary sighs. She holds her friend's hands and looks Lana deep into her green eyes.

"Precious, you need to stop questioning things. You know Dennis likes this new side of yours. We saw it. Multiple times." - Mary says adamantly.

"We did..." - she agrees gullibly.

"So, it's time for the next step. Practice and get better. Let go of your restraints, babe." - the blonde says, almost like an order.

Lana gulps. She doesn't realize it yet, but a large wall in her mind just crumbled. Mary's words always struck her harder than anyone else's.

"But Dennis..." - the naive fiancee insists.

"Will be the happiest man on earth." - Mary completes her sentence, squeezing her hands. "With the naughty version of you by his side."

"You think I have what it takes?" - Lana asks hesitantly.

Mary smiles at her. A smile overflowing with fondness and love. She needs to show her best friend that she is fantastic in every way. That every man and woman wants to have her.

Instead of replying, Mary turns toward the scrawny old professor, catching him staring.

"Henry!" - Mary shouts at him. He squeaks like a mouse and turns away. "Stop pretending. I know you were eavesdropping."

"Well, I couldn't help it." - the bony elderly man says.

"Doesn't matter. Come here." - the sexy blonde orders, motioning for him to approach.

Cautiously, Henry gets up and approaches the two hot teachers.

"How can I help?" - the mousey professor asks warily.

"Are you aroused by Lana?" - Mary asks bluntly. Lana gasps.

"Without a doubt." - Henry states without skipping a beat.

"But... Prof. Henry is a lecher!" - Lana says.

"Indeed he is." - Mary laughs. "But Dennis is too. All men are." - she points out.

"That is true..." - the gullible brunette mutters.

"So, Henry, what's your fetish?" - the blonde bombshell asks teasingly.

"Big Bazongas! Love 'em." - the old professor declares proudly.

Mary giggles and rolls her eyes.

"Of course you do. Men are so simple." - the blonde says, licking her lips seductively. "Bestie, pull your tits out." - she commands.

"Ahm? Right now?" - Lana asks, eyes wide as saucers.

"Yes, this will help you. Trust me." - Mary assures her.

'Mary knows what she is talking about. I asked for her help. I'll do it for her and Dens.' - the brunette thinks, inhaling deeply.

The busty fiance unbuttons her red sleeveless blouse and opens it, revealing her white cotton bra. She lets her blouse fall onto the chair and puts her hand on the bra clasp but hesitates.

"Come on, bestie. Show this old pervert your perfect breasts." - the milf teacher teases. "You'd like that, Henry?"

"Yes, please... show me your big knockers, Missy." - the old professor says, almost drooling.

Lana's coochie throbs hungrily. She takes another deep breath and unclasps her bra.

"Can you remove it for me, bff?" - the innocent brunette asks, clearly nervous.

"No, you need to do it yourself. You need to know that you took your slutty tits out for this old lecher on your own." - Mary says. Lana feels her nipples sting, and she nods.

The wife-to-be gingerly removes her brassiere, displaying her 38DD breasts to the hungry eyes of her colleague. Her giant boobs barely sag, and her wide pink areolas are capped with small, pointy, and equally-pink nipples.

"Cat got your tongue, Henry? What do you think of Lana's tits?" - Mary demands.

"Young Lady. I'll never not be impressed by these. They are the best I've seen. Better than any prostitute. I said you'd make good money with these puppies, and I meant it. They are perfect and take my breath away." - the professor says eloquently.

"Oh... thanks..." - Lana says, blushing. Absentminded, she crosses her arms underneath her boobs, pushing them up for his pleasure. 'This feels quite nice... I like how amazed he is by my boobies... it makes me feel hot and good... mmm... Mary knows what she is doing...'

"Good, good. Henry, do you want to suck Lana's tits?" - Mary asks teasingly. Henry's eyes widen.

"Mary!" - the brunette protests.

"Oh, hush, babe. He did it yesterday." - her sexy friend says.

"All right..." - Lana agrees sheepishly. She didn't really want to stop; the objection was basically involuntary.

"Indubitably." - Prof. Henry says. He takes one of Lana's breasts in his wrinkly hand. She moans softly. "Don't mind if I do, dearie." - he says as he dives in.

The scrawny old man starts sucking Lana's right boob with gusto. She moans approvingly.

'Oh goodness... this is a little indecent... doing this in the Staff Room...' - she thinks, delighted.

"Do you like it, Lana? Having your coworker sucking your tit." - Mary asks, rubbing her friend's bare thigh.

"I..." - Lana wavers.

"Tell me the truth..." - the blonde milf orders, her hand going up her bestie's leg.

"I do! It feels good. And so inappropriate... we are in the Staff Room! What if someone comes in? Mmm..." - the brunette says earnestly.

"That means you want Henry to stop?" - Mary teases, dangerously close to her pussy.

Prof. Henry stops for a second, listening in.

"No!" - Lana croaks. With a smile, Henry releases her boobie and engulfs her other one, making sure to suck and lick her nipple simultaneously. "Ahh... this is so improper... but it feels good..." - she moans.

After only about twenty seconds, Mary interrupts them. Lana whimpers, and Henry grumbles.

"See, Lana. This is what Henry likes. Now he's hard." - the sexy blonde says, rubbing the bump on the professor's pants. Lana gulps. "You need to use what Dennis likes to your advantage." - she states.

Without saying another word, Mary unzips Henry's slacks.

"Mary, what are you..." - the naive teacher questions. Her friend lifts her finger up.

"Now whip your dick out, Henry." - Mary bids. Her hand returns to Lana's thigh.

"Yes, dear." - the old man says, pulling down his loose boxers and letting his hard prick spring free.

Lana gasps at the unexpected sight. His old cock is wrinkly and covered in white pubic hair; however, it's reasonably sizable and thick.

'Wow... Prof. Henry's penis is thick... I didn't expect it... it doesn't fit with his thin and scraggly body. It makes it look bigger than it is... not that it's small... his pecker must be about 6.5 inches... two full inches bigger than Dens... and much thicker, too... gosh... Henry... who knew...' - she thinks, licking her lips absentmindedly.

"I know, right? I was pleasantly surprised, too." - Mary says. "Do you like it, bestie?"

"I do..." - Lana admits, feeling steamy. She feels her friend's hand rubbing the inside of her upper thigh.

"Missy, how do I compare to your young boyfriend?" - the boney professor asks.

"You are bigger than him..." - the busty fiancee says, not bothering to correct him.

"By how much?" - the old man insists.

"F-fifty percent..." - she says softly, biting her bottom lip.

"A couple inches?" - Prof. Henry says, and she nods. "Hah! It's good to know that we old folk don't lose out to the youth nowadays." - the elder man brags. "I'm sorry to hear about your boyfriend, birdy."

"It does not matter because I love him..." - Lana justifies, unable to break eye contact with his prick.

"Nonetheless, show Henry your appreciation by kissing his wrinkly thick cock." - Mary orders.

Lana gulps and glances at her best friend, who stares at her impassively.

'Dens, this is for you...' - she inhales, images of her smiling fiancee warming her heart.

With a slight, shy nod, Lana holds his hot and hard penis and leans forward, kissing the angry purple head of Henry's willy. She looks up at him expectantly.

"Delightful, young lady." - the professor says. "Can I have more?"

"Good idea. Lana, please kiss all over his shaft." - her blonde colleague says.

Lana plants tiny smooches all over Henry's cock, including his white hairy nutsack.

"Is this good?" - the gullible fiancee asks Mary.

"We're almost done. Now be a good girl and put him in your mouth." - Mary says nonchalantly. Almost as if rewarding her friend, she softly caresses Lana's pussy above her panties.

"Ahh... okay..." - Lana moans, unable to resist.

The busty brunette opens her mouth and engulfs the head of her coworker's old dick. Henry groans, delighted.

Lana sucks on his cockhead for a minute while Mary rubs her snatch.

'Gee... this is so lewd... ahh... I'm sucking on Prof. Henry's penis while Mary plays with my cooch... imagine if Roger comes in... or Stella... or a student! We wouldn't be able to explain... mmm... this is so hot...' - she moans, extremely aroused. 'I love it... I see what Mary is saying... mmm... I just need to let go of my restraints and practice for Dens.' - she evaluates

"Okay, this is enough. I believe I proved my point." - Mary says, removing her hand from her friend's sex. Lana pulls Henry's wrinkly prick out of her mouth with an audible 'pop'.

"Ah... yes..." - Lana says, slightly frustrated. She lets go of his sausage.

"Gah! You can't stop now, dear. I'm getting close." - the scrawny professor complains.

"Henry, get out of here. You abused your stay already." - the Hunter woman orders, standing up. She is taller than him because of her black heels.

"But you asked me to whip my cock out!" - Prof. Henry argues.

"And you were spying on our private conversation." - the blonde milf says, crossing her arms.

"Argh. But..." - the old man grumbles.

"Get out before I tell Bill about it." - Mary says with fiery eyes.

"Fine, fine. But I will have my way sooner or later." - Prof. Henry says, stumbling to put his prick back in his pants. He grabs his briefcase and leaves, thwarted.

Mary sits down and holds Lana's hand, who is breathing heavily.

"See? You let Henry suck your tits, and you sucked his dick, and nothing bad happened." - the blonde says.

"I guess..." - the curvy fiancee agrees.

"Be bold, babe. Explore and play. Get better and experience things. Everyone wants that." - Mary says.

"They do?" - Lana asks weakly.

"Yes, you are part of Winston now. Everyone wants you here. Forever. Break free of your shackles. I believe in you." - Mary smiles fondly at her friend.

The wise blonde's words resonate with our protagonist. This is all she wants, to be part of the town. To be loved by her fiancee and her friends. Another wall crumbles.

'Mary is right... I need to stop doubting myself and Dennis, and everything, really. Everyone is telling me to embrace things and be happy. I am the one stopping it from happening. Why can't I see that? No more. I will strive to be better.' - she decides.

"Thanks, Mary. I can always count on you." - Lana says lovingly, squeezing her hand back.

"You're welcome. Now I have something secret to discuss." - Mary says, lowering her voice.

Lana nods as she fixes her bra and shirt. She can still taste Henry's penis in her mouth.

~~~

Mary Hunter tells her best friend about her goal to become the school's new principal.

Bill has been acting out for years, causing many issues for the company and the town. The blonde woman has gathered information and evidence on the principal for years. Mayor Dick, as his brother, has a soft spot for him and doesn't see all the trouble Bill gets into.

Mary needs Lana's help with her power play.

"It's time for him to retire." - Mary explains.

"Woah..." - the busty fiancee says.

"Please, bestie." - the milf pleads, noticing a little doubt in her friend's eyes.

"How does he get away with it?" - Lana asks curiously.

"Nigel, Bill's nephew, keeps saving his ass." - the blonde teacher says, exasperated.

"Jeez..." - Lana mumbles.

"Um-hum, even Lucius, Jade, and I are constantly covering his messes up." - Mary elaborates.

"I had no idea!" - the brunette comments.

"Just because you have a huge meaty cock..." - Mary says, and the naive fiancee gasps softly. "... doesn't mean you can fuck up and destroy our precious little community!" - the sexy milf says fiercely.

"Mm-hmm..." - Lana nods, deep in thought. 'I'm not sure if everything makes sense, but Mary is my best friend. I will support her no matter what. Like she just did to me.' - she evaluates. "Sorry. How can I help?" - the big-titted newbie asks, smiling at her friend.

"I knew I could count on you!" - Mary cheers happily. "For now, go ahead with everything Bill wants. He can't know I'm onto him."

"That is it?" - the gullible teacher asks.

"I mean it when I say EVERYTHING." - the blonde emphasizes.

"Sure..." - Lana shrugs. 'I really don't get what Mary means, but I will do my best.'

"I'll need more help later, but I'll let you know when the time comes." - her friend says.

"Sounds good. Anything for you, bestie." - the voluptuous brunette smiles.

"Thanks, bff." - the Hunter woman says, happy to have a real friend.

They grab their things and leave the Staff Room toward their classroom.

"Ah! One more thing!" - Mary stops dead in her tracks. "Zack is in detention the next period."

"For the morning thing?" - Lana asks, recalling the incident with her and Greg.

"Yes, but I need to deal with something urgent. Outside of school." - the blonde says cryptically.

"About the Bill sitch?" - the innocent teacher asks, a bit too loud.

"Shhh... yes." - Mary says, looking around. "Can you cover for me? Just for an hour."

"Oh... sure. Let me message Chloe to take care of my class." - Lana says, messaging the class rep.

"Thanks, precious. I don't know how I will repay you." - the milf says.

"No need. That is what best friends are for." - the young fiancee smiles.

They hug, exchange a quick mouth kiss and say their goodbyes. Mary goes toward the Library, and Lana goes downstairs toward Mary's class, 2-C.

~~~~~~~

Recalling the morning incident, Lana is apprehensive about running into the students. To her surprise, the corridors are mostly empty, and the few stragglers seem to be in a rush to their classrooms.

'I guess it's almost time for afternoon classes. I often forget how dutiful the students here are... even if many of them are quite perverted and mischievous...' - she reflects.

As she reaches the bottom of the stairs, she notices a commotion outside.

'There seems to be a lot of people there... I better keep away... but... I wonder why... just a peek won't hurt...' - she tells herself.

Curiosity killed the cat, as they say.

Opening the doors, the teacher sees a long lineup of townsfolk leading to a small table. Jim and Simon are on the other side, handing the people something.

"Miss Lana! Came to see how we're doing?" - Herb asks, approaching her. The fat and shaved-haired boy, and the other two, are part of the AV Club.

"Herbie, what is going on?" - the teacher asks.

"The making-of! Everyone is here to pick their ups." - the boy says, lifting a DVD encased in a plastic sleeve labeled 'AV Club -- Misty Making-of starring Lana Cox'.

"Oh...." - she says, looking at the people and recognizing most of them from yesterday, during the event. Not many students seem to be here. "OH!" - she exclaims, realizing what Herb said.

'Jeez... I better leave before they see me...' - she thinks, but it is too late.

"Oh, it's Lana!" - someone shouts.

"You look sexy today!" - another fan screams.

"So beautiful!" - a third villager says.

"Our muse!" - a townie yells from the back.

People start clapping and cheering for her. She turns crimson and waves to everyone.

"They love you, Miss Lana. We all do." - Herb beams at his teacher.

'This is embarrassing... but I kinda like it... everyone looking at me...' - she thinks.

"Show us your tits!" - a person shouts.

The crows start chanting.

'Show us your tits' 'Show us your tits' 'Show us your tits' 'Show us your tits' 'Show us your tits'

Lana gasps. Herb chuckles and rests his chubby hand on her butt.

"Do it, Miss Lana. Show your boobs to your fans." - the teen says, squeezing her bum.

'Oh, gosh... they really like me... I would normally not do something like this, but I need to keep in mind what Mary just said. Maybe I can tell Dens about it tonight, and he will get a kick out of it. Okay, I'll give them what they want.' - she decides.

"They deserve a little treat..." - Lana agrees shyly, to Herb's surprise.

The teacher untucks her red blouse from her gray skirt. She takes a deep breath and lifts it, taking her white bra with it.

Her juicy melons drop out and bounce erotically to all the townsfolk.

A massive wave of cheers emerges.

Lana turns beet red, but her cooch twinges and gushes, wetting her white panties.

'This is such a rush... they adore it... I love it... it's so arousing... gosh... just showing my breasts, no, my slutty tits, to everyone gets me all hot and bothered. Gosh... I almost want to get naked right here... I can almost feel the thrill... imagine if I took all my clothes and masturbated in front of everyone... wow... Dens would love it...' - she thinks, biting her lip.

The bell rings, waking her up from her horny fog. She inhales, knowing she should stop it.

The future-wife quickly pulls her blouse down, shyly waves to everyone, and hurries inside.

"That was awesome, Miss Lana!" - Herb says.

The busty teacher enters the school and leans against the wall, her heart thumping, and her nipples and cooch throbbing.

'What was that... such a rush... gosh... I need more... okay. I need to tell Dens and ask if he has some ideas to take things a bit further.' - she muses, rubbing her legs together.

A message from Chloe saying, "I got this, Miss Lana!" reminds her of her duties. She wanders over to her temporary classroom for another detention.

~~~~~~~

She takes a deep breath as she grabs the door handle for classroom 2-C.

'Zack and his minions are probably inside.' - she dreads. 'I need to be strong and set the law. They respect me when I put my foot down. You got this, Lana.'

She walks into the room, and to her surprise, Greg is also there.

"Greg?" - the busty teacher exclaims.

"Hi, Miss Lana." - the boy shyly waves his hand. Her 'school boyfriend' is round-faced, short, and obese. He is always sad and pitiful, making him an easy target for bullies.

"It is detention time. Why are you here?" - she asks, knowing this could not end well. 'Whenever these boys and I are together, unsavory things happen.'