Naive Teacher in Winston Ch. 07

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 2022, so any correlations with real-life are mere coincidence.

This story is a slooooow burn. And no editor also, so bear with me :)

This chapter contains the following days schedule:

* Day 9 -- Tuesday -- Morning: Jack's house; Lunch; Afternoon: Homeroom; Clubs: AV Club;

Enjoy the read,

~ Potato Head

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Day 9 -- Tuesday

Early Morning

The young couple wakes up bright and early, ready to face a new day. They prepare themselves for work and sit together to have a yummy breakfast cooked by Lana Cox.

"Thanks for breaky, babe. Gotta say, the guys weren't wrong about your boobies." - says Dennis Laywood, smiling broadly, remembering the night before.

"Oh, you! What did they say again?" - she asks, trying to feign disinterest.

"Remember? They said your boobies were big and hot. They were right." - he grins at her.

She slaps his arm playfully and giggles.

"Maybe we can play some more tonight." - she says blushing. He nods enthusiastically.

They finish breakfast and Dennis prepares to leave for work.

"What do you have going on this morning?" - he asks her at the door.

"Nothing much, just tidy the house and then stop by Jack's on my way to school." - she answers.

"Jack? Why?" - he asks with a frown.

"He asked me to come over to pay the bet!" - she answers.

"Ugh, we need to stop making bets." - comments Dennis worried. "At least Lilly will be there, so nothing to worry about." - he says, and she nods.

He gives her a quick goodbye peck and he leaves for the day.

Lana goes upstairs and finishes getting ready for work, putting on a long-sleeve button up burgundy blouse. She decides to be a little daring, and leaves the top couple buttons undone, leaving her neck and collarbone exposed. Oh, the audacity!

Realizing she needs to do some laundry; she picks her only professional skirt left. It's a conservative gray knee-length piece, but it's extra flowy and flimsy, one of the reasons she avoided wearing it. She opts for simple yellow cotton panties and a basic matching bra.

An hour goes by, and Lana is organizing their bedroom when her phone lights up.

Message -- 09:37 --???

*??? -- Hello Lana, 'morning!

* Lana -- Who is this?

* PB-Justin -- Justin, I work with Dennis... remember me from the weekend?

* Lana -- Hi! Of course. How did you get my number? *worried emoji*

* PB-Justin -- Dennis gave it to me just now. Do you mind?

* Lana -- Ah, I see. I don't mind :)

* PB-Justin -- Good. Just wanted to ask if you gave any thought to what we asked him yesterday?

* Lana -- What do you mean?

* PB-Justin -- Dennis said he told you about it...

* Lana -- *confused face*

* PB-Justin -- We asked him to ask you if you could flash us your pussy again this weekend?

* Lana -- Justin! You shouldn't say that!

* PB-Justin -- Is just a friendly banter between friends ;)

* Lana -- Still, doesn't seem appropriate to talk about this with Dens' coworkers.

* PB-Justin -- He knows we are chatting, so no worries there.

* Lana -- He does? I guess then...

* PB-Justin -- So... will you show us your bare snatch? :)

'Hmm... Dens didn't say no to them, and he told me he doesn't mind showing and exposing... he said it was even encouraged! Kim did it on the story, her husband seemed to like it. Maybe I can do it too...no, Lana, it's not proper...they work with him!' - debates Lana in her head.

* Lana -- I probably shouldn't...

* PB-Justin -- Fuck yeah, you should! Thanks for agreeing.

* Lana -- Stop it, Justin!

* PB-Justin -- The boys will be happy! This weekend will be awesome.

* Lana -- I didn't say I would do it! :(

* PB-Justin -- ;) I'll add you to our group chat later and we chat more. TTYL Lana!

* Lana -- Bleh :P, tell Dens I say hi.

She frowns, she didn't agree to it, but he basically made it sound like she was going to do it. She would have to clear things up in the group chat. Future Lana's problem.

The young and stacked fiancee finishes getting ready, picks up her work materials and makes her way to Jack's house.

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Morning -- Jack

Lana knocks and Lilly opens the door, inviting her inside.

"Hi, dear! Thanks for coming over." - says Lilly, holding a bag in one hand and Evan in the other.

"Oh, no problem." - she smiles, dropping her work stuff at the entrance. "Where are you going?"

"I am taking Evan to a class. He loves to swim." - she says and pats her son in the head.

"He is a cutie." - admires Lana. "You two have fun!"

Lilly says her goodbyes and leaves with Evan in tow.

"Jack?" - asks Lana sheepishly out loud.

"In here!" - comes a booming voice from the living room.

She enters the room and is surprised to see there is someone else there with Jack. He is turned and fiddling with some wires, so Lana can't see his face clearly.

"Hi Lana! Good morning." - beams Jack to his neighbor.

"H-hello Jack. Who is this?" - she asks nervously.

"Ah, I thought you two had already met." - says Jack pointing to the man. "This is Kenny, he is the janitor at the school."

The man turns and smiles. Lana recognizes him from the day prior, when he waved at her.

"Oh, hi Kenny! Nice to meet you, I am Lana Cox, a teacher at the school." - she introduces herself.

"Hi, Miss Cox, pleasure to meetcha." - says Kenny simply.

Lana takes a good look at him. He is in his early twenties, tall, around 6'3, skinny, extremely pale and has an absent look on his face. He is wearing blue sweatpants and a t-shirt covered with paint stains.

"Neighbor, sorry to ask, but why is Kenny here?" - she asks trying to sound respectful.

"Ah, right. Kenny sometimes helps me with maintenance around the house. He is very good at it." - informs Jack. "He was helping me this morning with the wiring, so I asked him to stay around to assist with the photos, you know, frame them better." - he answers.

"I see." - says Lana. "Not sure I am comfortable with it..." - she says nervously.

"Nonsense, Kenny here is a great lad." - compliments Jack. "Extremely trustworthy. I can vouch for him."

"My bad, Miss Cox, I'm only here to help ya." - Kenny completes with a sad look on his face.

"Ah, Kenny, I didn't mean anything by that. It was insensitive of me." - she tries to course correct. "Of course, you can stay, you seem like a decent young man."

"Good, it's sorted then." - smiles Jack. "Kenny, please finish up with the wiring on the living room, while I get my photo equipment." - instructs Jack. Kenny nods.

He quickly finishes his work and Jack brings in his equipment, setting it up in an open space.

"Lana, dear, since you came in so late, we'll only do 1 pose today, okay? We can do the rest in the future." - explains Jack.

"Sure, that is fine by me, I need to get to school anyway." - she says relieved.

"My idea is to have a simulated photo. I don't want to cross any boundaries between you and Denny-boy." - informs Jack seriously.

"Oh, nice of you to worry, Jack." - she says pleased. "What do mean by 'simulated'?"

"You know... simulated." - he replies seriously. "We'll pretend to do something, but it won't be real."

"Right, it's just posing for a photo." - she says slightly confused by his affirmation.

"Yeah, pretend we are both models, it's not real, so there is no need to worry." - he emphasizes.

"Ah okay, if it's just pretend... seems harmless." - she says agreeably.

The overweight neighbor guides Lana to the other side of the camera and instructs Kenny to signal when they are in frame.

"Jack, what are we going to do?" - asks Lana innocently.

"Oh, we are going to do a simulated blowjob photo." - he says nonchalantly.

"What!?" - says the young teacher in shock. 'Jack is asking for a photo of me giving him a blowjob? I couldn't...' - she worries.

"Don't worry, it's not a real blowjob. It's pretend." - explains the balding man.

"I can't do that!" - she says exasperated. "I shouldn't get close to your penis!"

"First of all, it's just posing. You won't be sucking me." - he clarifies. "Second, you and Denny-boy lost the bet, so you owe me a few poses of my choice. This is what I picked out."

"Darn it Dens..." - she mumbles. "Still, I shouldn't interact with your thingy!" - she argues.

"You may not have to, it's only simulated." - elaborates Jack, trying to convince her. "You can just get close and look at it, may not even need to touch it!"

The naive teacher didn't get the emphasis on the word 'may'.

"That's still too much!" - she says. "Dennis is not comfortable with this!" - she justifies.

"What are you and Dennis comfy with? I bet you never even talked about it." - he provokes her, trying one last desperate attempt.

"You just lost that bet, mister!" - she replies, falling into his trap. "As a matter of fact, me and him had a few conversations this weekend." - she explains proudly.

"Oh, yeah?" - he smirks. "What did Denny-boy say?"

"Accidents don't count, so as long as things are not on purpose, they are okay." - she says. "But posing is not an accident, definitely on purpose." - she states. 'Of course touching his big penis would not be an accident...' - she reflects.

"What things? Kissing, touching and looking were part of the rules?" - Jack says, slowly guiding her towards the path of corruption.

"Well, those are fine, he didn't seem to mind when they happened." - she admits. "But anything else, is not!"

"If it's just ogling my dick, as you just mentioned, Dennis is fine with that." - he says.

'Oh my... I did just say that... am I sure Dens won't mind? What if I am staring at his naked phallus while posing for photos? Ugh, I guess it's covered by the chat.' - she says in her head, torn.

"And, like I explained, you may not have to touch it, so nothing to worry about." - the bald man continues. "Didn't I say it, Kenny?" - he asks the other man.

"You betcha, Mr. Jack." - agrees Kenny.

Lana looks at him spooked, forgetting he was there for a second.

'The janitor is here! I'll have to ogle Jack's peen in front of him!' - she thinks.

"So, time to pay your bet dear Lana, it will be quick." - the middle-aged neighbor says.

"Even if I agree, I shouldn't do this in front of Kenny!" - she argues.

"He won't say anything. Besides, you promised it was okay for him to stay." - smiles Jack.

'I did promise... I guess it can't be helped...' - Lana reflects. "Ugh, fine. Let's get on with this so I can go to work!" - she says reluctantly.

"Great." - Jack smiles. "Lana, crouch and turn towards me so you are sideways to the camera." - he instructs.

She sighs deeply and does what she is told. Jack turns towards her and quickly pulls down his sweatpants to his ankles, revealing he is not wearing any underwear. His heavy penis flops against his hairy thigh.

Lana gasps out loud, surprised by the appearance of the bare penis. She looks at it intently. Jack's penis is still soft, but it's already so thick. She shudders, remembering how big it was the last time she saw it.

'Oh my goodness, oh my goodness, oh my goodness.' - she panics in her head. "What n-now?" - she asks wide eyed to the balding man.

"Move that plump booty forward, dear. Get closer to my dick." - he commands.

She moves sheepishly, mesmerized by the presence of the manly snake in front of her. Her face is now a foot away from it, his strong musk assaulting her cute little nose.

"Is t-this good?" - she asks uncertain, both embarrassed and excited about the events. 'What a strong and intoxicating smell... Dens doesn't smell like this... it's so manly...' - she thinks.

Jack puts his hand on his chin, as if wondering. He holds the base of his soft penis with his other hand and lifts it a little, getting it even closer to the teacher's face.

"Hmm... I don't think this looks right. Kenny?" - inquires the neighbor.

"Not at all, Mr. Jack." - agrees the young man.

"What is wrong?" - asks Lana looking up at him. She can feel her nipples harden underneath her bra.

"It doesn't look like you are giving me a blowjob. I'm not even hard." - he states calmly.

"Erm... can't you get it up?" - she asks naively.

"You know that's not how it works, dear. The best way is for you to make it hard." - he smiles at her. She feels her coochie twitch at his words.

"I can't! H-how? What s-should I do?" - she stammers, a thousand thoughts crossing her mind.

"Do what I'm doing, just hold the base of my dick. It'll get hard in no time." - he grins.

'Oh no, I'll have to touch his fat penis... No, he said it wasn't required.' - she reflects. "But you said I probably wouldn't need to touch it." - she says nervously.

"I say you may not need to touch it." - he clarifies. "But here we are, you'll need to do it. It's the only way." - he says.

Her eyes widen again, and she opens her mouth to say something.

"Besides, Denny-boy said touching was fine and he already saw you touch it on the weekend." - Jack interjects. "I even have photos." - he smiles.

'I did touch it... and Dens enjoyed it...I kind of want to...' - she thinks. "And it's only simulated, right?" - she asks, using his previous words to justify her behavior.

He nods emphatically. The future wife feels her cooch twitch again, she is really going to do this.

She moves her hand forward instinctively, softly contacting his hot peen. Her coochie pulsates and gushes as soon as she does so, slightly wetting her yellow panties.

Feeling her warm and soft hand, and seeing her lustful face is enough to get Jack going. In a span of mere seconds in her hand, he goes from completely soft to rock hard.

"Oh, my!" - she exclaims out loud, eyes as wide as saucers. 'I am touching his erect member... my neighbor's thick penis is in my hands... it's hot... I am so wet already...this is so naughty...' - her thoughts roam.

She can feel his warm and erect penis pulsating in her hands. Her engorged nipples so hard that they are trying to escape through her blouse.

The pose is extremely lewd, Lana is crouching in front of her neighbor's fat 7'5 cock, while she holds it with her right hand less than half a foot away from her face.

"Nice job Lana. Much better, right Kenny?" - inquires Jack.

"Looks fucking hot, Mr. Jack." - agrees the janitor. "So real, she looks like she needs a cock."

Lana squeals at the young man's words. Jack laughs deeply.

'It's just pretending, it's not real. It's only to pay the bet.' - she tells herself.

"Lana, last thing. Look at the camera, open your mouth and widen your legs to expose your panties to the lens." - orders Jack.

"Okay..." - she whispers obediently. She does as he instructed, her damp yellow panties coming into view.

With her mouth now open, it does look like she is about to wrap her soft lips around his dick. She whimpers at the thought of being so slutty.

'They can see my damp panties... and his penis is so close to my lips... what would Dens think if he saw it... what would my students think... seeing me holding my neighbor's thick peen right in front of my open mouth and exposing my wet cooch to the camera... so lewd... such a bad teacher...'

"Shoot away young man!" - says the balding man, posing with his arms at his hips and grinning widely.

Kenny starts to take a lot of photos, the nonstop flashes and click sounds inundating the room. After half a minute, he stops and gives his boss a thumbs up.

Lana absentmindedly starts to squeeze Jack's dick. He smirks at her, who seems lost in thought.

"They look good?" - he asks and Kenny nods. "Come here and show me." - he doesn't want to interrupt the cock massage he is getting from the young teacher.

The young janitor approaches them, and Lana notices a huge bulge on his sweatpants. Beyond huge, it looks massive.

'I am glad I am not doing this to his massive thing... that would be improper...' - she thinks.

Jack makes an unsatisfied noise, and Lana looks up at him, not letting go of the penis.

"What is wrong?" - she says, with lust in her voice.

The overweight neighbor signals to Kenny and he moves back to his spot behind the camera.

"It's still not convincing enough. Your blowjob simulation is not good Lana, maybe you're a bad actress." - says Jack unhappily.

"I am not! I know I can act." - she says, not liking to be criticized. "What can I do?"

"It doesn't look like you are blowing my dick on the photos, so that's the only way." - he says seriously.

"What is?" - she asks slightly confused, her nipples aching at the mention of blowing him.

"You'll have to put it in your mouth a little bit. Just the tip." - he says nonchalantly.

"Ahm? No, I said that wasn't okay!" - she argues back, her coochie betraying her at the thought of doing it. She tightens the grip around his fat member.

"This is all pretend. It's not real. So, what you discussed with the fiancee doesn't apply!" - argues Jack.

"Putting your penis in my mouth is definitely beyond the boundaries!" - she argues back.

"Wait, what exactly did you both agree? Be honest." - inquires Jack.

"No penetration or putting things inside me..." - she explains frankly, giving his cock a squeeze.

"Did Denny-boy specify where?" - says Jack, seeing an opening. His penis twitching in her hand.

"In my vajayjay, he said." - says Lana weakly, almost knowing what was about to happen.

"So, your pussy is off-limits. Deal. But nowhere else?" - pushes the neighbor.

"I guess not..." - she says realizing Dennis hadn't said anything about mouth or hands.

"Even in your tight ass?" - interjects Kenny.

Lana nods shyly, noticing the bulge on his pants get bigger. Her eyes widen.

"You're already touching my dick, and he's okay with you kissing others." - arguments Jack. "This is just like you kissing the tip of my cock." - his peen jerks again in her hand.

'Oh, no. He is right... it feels a bit wrong... maybe I want to... why I am still holding his thick penis? Ugh! Dens didn't forbid me of doing this... my mouth is probably okay... that tramp did that to him anyway... I'll almost be even if I do. Yeah... I need to pay this bet and if this is the only way....' - she decides in her head.

"If I do this, will you consider the bet paid?" - asks the young fiancee, squeezing his penis.

"Yes, this photo will be done." - agrees Jack sneakily.

"And it's just pretending, right? I am not going to blow you." - she says, her cooch spasming.

"I promise." - swears Jack, making his cock twitch.

"Fine then, but let's do it quickly so we can end this." - says Lana trying to sound unenthusiastic.

"Cool, back to our poses then." - instructs Jack. "Ready, Kenny?

Lana holds the neighbor's penis firmly, opens her legs wide and smiles at the camera again.

The pale lean youngster readies himself to take the photos and gives them a thumbs up.

"Go ahead, dear Lana." - pushes Jack. "Wrap your plump and pretty lips around the tip of my cock."

Lana squirms at his words. Her heart beats strongly in her chest.

'Oh, my goodness... I am really going to do this... this will be the second penis ever in my mouth... the first one in broad daylight... and they'll take pictures... heck, they'll have these pictures of me with a big fat penis in my mouth forever... ugh... what I am doing... but I agreed to it, I can't back down now... it's just to pay the bet.' - she says steeling her resolve.

"Here I go..." - warns the busty teacher to herself.