Naive Teacher in Winston Ch. 12b

Simon cuts the dress slit to be almost level with her pussy. Herb doubles down on it and makes the slit go to her waist. Any wrong move could expose her virgin cunt to everyone.

"Boys! This is too much!" - she complains, looking at their latest alteration.

"Don't worry, Miss Lana. We're almost at the end of the event." - Simon assures her.

"And Dennis is fine with it." - the chubby student adds.

"I am not sure he likes when everyone sees my vajayjay." - Lana says.

"It's too late now. We already cut it. And I guarantee he loves it." - Herb makes an OK sign.

'Hmm... I'm not convinced, but it is too late to worry. Let's see what Dens says.' - she evaluates.

~~~~~~~

Pee Break

Herb starts to walk back to his place, but Lana calls him.

"Herbie, I need to pee. Can you show me where?" - she asks.

"Erm... we don't have a spot. Maybe we can go to the convenience store?" - Herb asks Simon.

"We can't, Hoseman. We are almost out of time, and there are still a few people for the photos." - the long-haired boy points out.

"Damn." - the fat student says. He suddenly has an idea. "Ah! I can take you to the bushes. It's secluded enough. Nobody can see."

"I guess so." - the teacher says in agreement.

As Herb escorts the busty wife-to-be, they pass by the line of fans, and people catcall and shout all sorts of names at her. Greg is there, trying to keep everyone in order.

"Oh, Greg. Come with me. I need your help." - Herb says to the lonely chubby boy, who nods and follows them.

The AV Club student guides them to some bushes near the event area. The "bathroom" location is only about 50 feet from the line, so the townsfolk can see them clearly.

Sheepishly, Lana goes into the vegetation and chooses a spot. Herb gives her a thumbs up. She nods apprehensively toward the fans, who are looking their way.

"We'll protect you. Don't worry." - Hoseman says, turning his back to her and blocking the villager's view with Greg.

They cross their arms as if they are security guards. Lana giggles at their antics.

She glances in the direction of the people, but the two fat boys are doing an excellent job of blocking her from sight. Satisfied, she turns, hikes her dress, and squats.

As Lana takes care of her business, Greg shuffles around, letting people get glimpses of Lana mid-pee.

Herb notices this and playfully punches the chubby boy, asking him to stand straight. Greg, feigning dumb, keeps wobbling and moving. Frustrated, Herb decides to let go.

Unbeknownst to our naive teacher, many people saw her taking a leak, and some took pictures. Some of these photos might make a reappearance in the future.

~~~

As she leaves the bushes, the trio sees Jim chatting with Jen a few feet away. Jen is Chloe's best friend, and Jim has had a crush on her since forever.

The two have yet to see the group. Lana puts her finger to her mouth, asking Greg and Herb to be quiet. She wants to eavesdrop.

"So, will you go out with me?" - Jim asks, flustered.

"Hah! Did Chloe put you up to this?" - Jen asks, amused.

"Erm... no..." - the ginger boy stammers.

"Well, the answer is an obvious no. I wouldn't be caught dead with a nerdy boy." - the brunette athlete says.

"But..." - the AV Club president mutters.

"Better luck next time." - Jen dismisses, leaving.

They see Jim's eyes fill up with tears. He runs away, heartbroken.

"Shit. I better go after him." - Herb says worriedly.

"Let me know if I can help." - Lana offers.

"Thanks, Miss Lana. But Prez needs his bro." - the shaved-haired teen says, running after his friend.

The teacher sighs. 'Poor Jim, Jen was so mean to him. She is so daft! She will never find a better boyfriend than Jim. Even his penis is great. I mean... that doesn't matter. Maybe a little. But his personality is good too. He is sweet, loyal, and caring.' - she reflects.

"Man, that's gotta hurt. I know the feeling." - Greg says sadly.

"Oh, poor Greg." - Lana says, caressing his chubby cheek. 'I will talk to Jen tomorrow. Maybe I can change her mind to give Jim a chance.' - she decides.

[Potato Note: while Jen was extremely mean to the boy, neither Jim, Herb or Lana realize that the girl is a lesbian. Oh, well. Mistakes abound! Good for us.]

~~~

Lana returns to the photo area, and some more townsfolk come over. Every single one of them requested the teacher to expose her twat during the photos. They also rub the props on her vagina, which she lets them all freely do. Thankfully, no one tries to insert the object into her (to her slight disappointment).

Her Princess Leia cosplay top has been chopped to show a bit more cleavage, while the bottom of her dress now ends halfway up her thigh. Combined with the dress slit that goes to her waist, her costume looks scandalous.

As the people come and go, our gullible teacher is increasingly desperate for relief. As a reminder, her nipples throb desperately.

'Maybe I can orgasm after the next person?' - she thinks, pinching her aching nipples.

~~~~~~~

Mayor Dick

"Miss Lana, we're ending soon. The next person is the last." - Simon announces.

The shapely future-wife sighs, a mix of relief and pent-up frustration. 'Calm down, I will be able to take of it soon...' - she tells her fired-up body.

"Looking lovely, Ms. Cox." - an elegant elderly man says, strolling towards her.

"Mr. Wins-" - Lana starts to say, but she catches herself due to his expectant gaze. "Mr. Dick!" - she corrects. He smiles, pleased.

"Mayor Dick..." - Simon says nervously. "I'm sorry, but just a reminder that there is no touching our model directly."

"Of course, youngster. I appreciate the reminder." - Dick nods.

Richard 'Dick' Winston-Phillips is an elderly man in his seventies who is still fit and elegant. Even though he has white hair, his cheeky smile indicates that there is something more playful to his personality. He is the town's Mayor, the president of the Winston-Phillips Co., and the patriarch of the Winston-Phillips family. He basically owns Winstonstead.

"It is good to see you again, Mr. Dick." - Lana says politely.

"Please, dear. Skip the mister. Just Dick." - the Mayor grins, stopping beside the teacher. "And yes, it has been a whole week. How are you enjoying the town?"

"Oh, I love it. It already feels like home, Mis... Dick." - the busty fiancee says.

"That is fantastic. I heard extraordinary things from my brother, Bill." - Dick says.

"Thanks, I am enjoying teaching at the school." - the teacher smiles.

"The 'Program' suits you perfectly. I am elated you agreed to be part of it." - the Mayor nods.

"Ah... uhhh... the honor is all mine." - Lana says, blushing.

"Indeed!" - Dick smiles, his eyes sparkling. "Let us take some photographs now?"

"I'm ready when you are, Mayor." - Simon says from behind the camera.

"Dick, people have been using props to pose with me. Do you want one?" - she points at the prop box.

"No need for that, Ms. Cox. I am too old for these things. 'Stellar Wars'." - the old man chuckles.

"It is Star Wars..." - she says quietly.

Suddenly, Lana sees her fiancee walking into the photo area.

"Oh, Mr. Winston-Phillips! Glad you came to the event." - Dennis says from the entrance.

"Mr. Laywood! Nice to see you." - Dick grins. "Thank you for letting me borrow your beautiful fiancee." - the old man says, moving behind Lana.

"You're welcome, Mayor. I'm happy to please." - the ginger man says subserviently. "Lana, what are you wearing?" - Dennis asks, seeing the current state of her outfit.

"Ah, some people went overboard." - she tries to explain.

"Sorry, Mr. Laywood. We couldn't stop them." - Simon adds.

"I think it is fine. Ms. Cox looks mighty wonderful. Don't you agree, Mr. Laywood?" - Dick asks, intently staring into Dennis' eyes.

"Oh, yes. Lana looks beautiful." - the ginger man agrees. He decides to drop the subject until later.

"Good, good." - the Mayor smiles.

Lana feels Dick's hand rest on her butt. She ignores it, and he gropes her ass. She flinches slightly.

"Dens, you wanted to talk to me?" - she asks, trying to overlook his advances. Dick squeezes her thick posterior a couple of times.

"Yeah, babe. But it can wait a minute. I'm sure Mr. Winston-Phillips wants to get on with the photos." - her fiancee says.

The phat-assed teacher feels Dick's hand slide down and under her dress. She holds her breath.

'What is he doing? That's against the rules! Dens is right here...' - she thinks worriedly.

"Please go ahead, Mr. Laywood." - the company's president says.

"Not at all, sir. I don't want to be rude." - Dennis says adamantly.

Lana feels Dick's hand contact her cooch. She holds in a gasp.

'Oh, gosh... Dens might get mad at the Mayor if he finds out... not good... I don't want any trouble... maybe I should pretend nothing is happening...' - she considers.

"You are not. Go ahead and talk with your future-wife. I do not want to disrupt a schmooze between lovers." - the Mayor asserts seriously. Richard's bony hand starts to caress the teacher's bare snatch.

"Sir, If you insist." - Dennis says, unsure.

'Gee... Dick is playing with my coochie in front of Dens... mmm... if Dens gets mad at Dick, he can lose his job... ahh... I better ignore him... let him do it...' - she deliberates.

"I do indeed." - Mr. Winston-Phillips nods.

The old politician rubs his finger along her aroused clit. A jolt runs across her body, making her shake slightly, including her braless boobies.

"Babe, are you okay? You just shook all of a sudden." - Dennis points out, a concerned look on his face.

"Ah... I am fine, hun... just a shiver..." - the wife-to-be says weakly.

"Probably just a gust of wind. Particularly common around this area." - the Mayor says, flicking at her clit. She trembles again, almost letting a moan out.

"Weird, I didn't feel anything..." - the ginger man says, looking around. "Oh, well." - he shrugs.

"So, Mr. Laywood. Go ahead, talk to your woman." - Richard says, petting Dennis' future-wife's wet twat.

'Eeeekkkk.... Dick is going overboard... he needs to stop...' - she thinks, extremely aroused.

"Right. So, babe, I just came to tell you that me and Pietro are..." - the ginger man says.

"Pietro and I...." - Lana corrects, interrupting her fiancee.

"Ugh! Pietro and I are going to play some games at our place." - Dennis finishes, motioning to the exit.

"Ah... all right..." - she says breathlessly. Her face is unusually flushed.

"Are you sure you're okay?" - the worrying fiancee asks.

"I am... I just..." - Lana starts to say. 'I can barely speak, Dick is distracting me...' - she thinks, so on edge from the day that she really doesn't want the pussy-play to end.

"Maybe Ms. Cox got worn out from the day." - the company's president completes, coming to her aid.

"True. It was draining." - the ginger man agrees. "Don't exert yourself, babe. I'll meet you for dinner, 'kay?" - he locks eyes with her. And she nods weakly.

Lana feels Dick's thin finger slips inside her sloppy cunt.

"Nnnggg..." - she groans faintly. Dennis looks worriedly. 'Oh, gosh... keep it together.' - she tells herself. The busty teacher inhales, trying to compose herself. "I am alright, Dens." - she assures her trusting fiancee.

"Okay. Pietro is waiting. I should go." - Dennis says. Not wanting to make things more awkward in front of his boss' boss, he decides to quickly leave. "Bye, Mr. Winston-Phillips." - he begins to leave.

"Mr. Laywood, are you not going to kiss your betrothed goodbye?" - Dick asks as he gradually slides his finger in and out of the teacher's pussy.

Lana bites her lip, trying to keep her voice from coming out.

"Oh, I didn't want to be rude." - Dennis explains, glancing worriedly at Lana. She forces a smile.

"Nonsense. It is the least a loving fiancee can do to his significant other." - Richard insists again.

Knowing there is no way out, Dennis shyly approaches them and gives Lana a quick peck on the lips. As he does, the lewd Mayor pushes his finger further inside her. She flinches.

Dennis notices that his betrothed is breathing a bit too heavily.

"See? Much better." - Mr. Winston-Phillips says with a wide smile.

Lana squirms under Dick's naughty finger. She feels an orgasm building up.

"Thanks, sir." - Dennis smiles. "You're so red, babe. You might have a fever." - he puts his hand on her forehead. "Not too hot, just a tad. Take care, okay?"

Dick removes his finger and daftly pulls her dress down. The curvy fiancee feels relief but also disappointment that she didn't get to come once again.

"I will... see you soon." - the voluptuous teacher says, trying to keep any feelings in check.

"I'm worried about you. Do you want me to stay?" - Dennis asks quietly.

"Not necessary, young man. I assure you that I will tend to your bespoken." - the Mayor says, resting his hand on her ass again.

"Yes, sir. See you at dinner, babe." - Dennis says.

"Bye, hun." - the buxom educator says breathlessly.

The ginger man nods to Simon and walks away with a final wave.

As soon as he is out of sight, Lana moves away from Dick.

"Mayor Dick! What do you think you are doing?!" - she shouts, panting. Simon looks at them, confused.

"Ah, darling. It was a silly prank. I could not resist." - Mr. Winston-Phillips gives her a cheeky grin.

"Oh..." - the naive teacher says, her defenses immediately coming down. 'Dick was just teasing me! Still... that seemed too much...' - she thinks, unconvinced.

"You were not aware that I love to play pranks on people?" - the old Mayor explains.

"I did not..." - she admits. 'Was it really? Hmmm... if it's true, pranks can't be helped... He is the Mayor... he wouldn't just abuse me in front of my fiancee, would he? No... of course not...' - she thinks gullibly.

"Ah, I understand how that might have come across then. Apologies." - Dick says wholeheartedly.

"Oh, it is not an issue... I just... was not expecting it." - Lana says earnestly. 'He seems sincere. I guess since it was a prank, Dens won't be upset. Phew... and here I was worried for a second.' - she considers, relieved.

"Well, next time, you know." - Richard says with a grin.

'Next time?' - she exclaims in her head.

"Mr. Mayor, do you want a few photos?" - Simon asks, interrupting her thoughts.

"Hmm... maybe just one photograph. I could display it in a picture frame on my desk." - Dick says.

"At city hall?" - Lana asks.

"Yes. Have you been, Ms. Cox?" - Mr. Winston-Phillips inquires.

"I have not had the pleasure." - she says genuinely.

"Please visit me this week. At any time." - the old man requests, patting her bum.

"I will. Do I need an appointment?" - the teacher asks.

"Not at all. I have an open-door policy." - the Mayor informs her.

They pose next to each other, smiling for the photo.

"Shame that I cannot stay longer. I have a family event to attend." - the old man says.

"Oh, with Principal Bill?" - Lana asks.

"Indeed. I heard that things are already remarkably intriguing." - Dick says, hinting at possible events.

Surprising the teacher, the Mayor steals a kiss from her. He chuckles as he strolls away.

~~~

Since the event is over, Simon turns off the camera.

"Miss Lana, can you help me arrange things? Herb is still talking to Jim. And my dad and Dennis just left." - the long-haired boy says, exasperated.

"Of course, Fabio." - the teacher answers fondly. 'Gosh, I need to delay my orgasm... Mr. Dick got me so hot... I know it was just a prank... still... I need some relief... badly.' - she thinks.

As they pack and arrange the photo area, the teacher chews over what happened with the Mayor.

'I wonder if maybe it was a test? Maybe Bill is testing me..., or Dick is testing Dens. I am so confused. Maybe it has to do with his promotion? I wonder if I should tell him. No... I probably shouldn't reveal it to him if it was a test. Maybe it's part of the test? Argh! Maybe Mary will know what to do or what it meant. I will ask her tomorrow.' - she ruminates.

Simon keeps glancing at his teacher, who, due to her short dress, is unknowingly flashing him her glistening pussy with every other movement. His pants are already a mess from Chloe, but now, Miss Lana risks causing him another accident.

Thankfully, they are interrupted by Herb.

"Hey, Miss Lana. Prez needs your help." - Hoseman says.

"He does?" - she asks worriedly.

"Yeah, with the Jen thing. He's in the tent." - the shaved-haired student points.

"All right. Sorry, Fabio. I should go help Jimmy." - Lana says, putting the equipment down.

"Go ahead, Miss Lana. I will fill Fabio in and be right behind you." - Herb says.

The busty teacher nods and prances toward the tent, eager to help her favorite male student.

"Who is going to clean all this shit?" - she hears Simon ask his friend.

"You? I'll owe you one." - Herb says.

"I can help!" - Greg says, coming from the entrance of the event area.

"Where were you?" - Simon inquires, frustrated.

"Pooping!" - the friendless fat student says proudly.

"Fucking hell, dude..." - Simon mutters as the large-assed teacher enters the tent.

~~~~~~~

Lana sees Jim sitting on top of a wooden box, quietly moping. He looks up at her with big puffy eyes. He had been crying.

"Hi... Miss Lana..." - he says sadly, barely paying attention to her.

"What happened, Jimmy?" - she asks, going toward him and caressing his hair affectionately. She had witnessed enough of the event to know what had occurred.

"*Sigh*.... your suggestion didn't work." - the nerdy boy says sulkily.

'He must be serious. He did not even look at the state of my cosplay...' - she thinks, her aroused state still dominating a good chunk of her brain power.

"It is going to be okay, Jimmy. I am here now." - the teacher hugs his head and gently strokes his soft ginger hair.

"It's all your fault..." - Jim says darkly.

"Mine!?" - Lana exclaims. She steps back, feeling attacked. Herb silently comes into the tent.

"I thought... I thought... *sniffle*.... That since you showed interest in me..." - the ginger student starts to say.

"I just... was trying to motivate you and.." - the busty educator begins to defend herself.

"Caham! Miss Lana." - Herb interrupts her with a serious tone. She stops. "Let Jim finish. It's important." - he says. She nods meekly.

Jim takes a deep breath and wipes his eyes. He slaps his cheeks, pepping himself up. He looks down at his feet and starts to spill the beans.

"I never thought I had any chance with girls my age. None of us did. We were content to be our lame selves in our own isolated world." - Jim says, pausing.

"That's right." - Herb agrees, filling the silence.

"But then you came along, Miss Lana. A beautiful girl... nay... woman. Smart, hot, pretty, and fun. The sexiest woman I have seen. One that likes nerdy stuff and that wants to see us grow. And you paid attention to us! Three nerds with their own geek club. It was the stuff of our dreams." - the club president says. The teacher blushes furiously.

"It was, it was." - the chubby student echoes his friend.

"When you, an amazing woman, showed interest in us, in me, it gave me hope. If this gorgeous and voluptuous teacher could be involved with me, a girl my age certainly would. At least asking one out seemed plausible now." - Jim explains, shuffling his feet.

"That's true." - Herb nods along.

"I knew I could never be with you, Miss Lana. You are basically married. Yes, I love you, but it's one-way love. I recognize that. It's not realistic." - the ginger boy says, and Lana feels her heart beat faster and her tummy tingle.