Naive Teacher in Winston Ch. 09

Physical checkups, asshole pic and detention titfuck.

~~~

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.

IMPORTANT:

This chapter will be huge. Sorry, it got out of hand.

I was initially going to divide it into 2, but I am trying to preserve the 'at least one day per chapter' thing. So, you may see some part A and B mentions.

Sorry about the butchering of the Indian character. I tried to have fun adding some Hindu words, but I am clearly out of my depth here. Please forgive me!

Day 11, Thursday, contains the following schedule:

* Part A -- Morning: Lilly / PE / Physical Checkups;

* Part B -- Morning: Shower; Lunch; Afternoon: Detention; Clubs: Library; Dennis;

Thanks everyone for the suggestions, keep 'em coming!

Enjoy the read,

~ Potato Head

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PART A

Asshole pic, first fingering and male physicals.

~~~~~~~

Day 11 -- Thursday

Early Morning

Lana Cox stirs awake by the sound of her fiancee's alarm going off.

Lana was a naive busty brunette beauty, with big green eyes and fair skin. She was short, standing at 5'3 (161 cm), but was in great shape due to all the exercise.

For those who enjoy curves, Lana had an all-natural dynamite body, with 38DD breasts, a peachy phat ass, thick and toned thighs, flat tummy and a voluptuous curvy figure.

Yes, she was not everyone's cup of tea, but people could not help but stare at the prude and innocent fiancee's body. Her frame stirred something deep inside, even in the best of us.

"Ugh... morning..." - Dennis mumbles groggily.

"Morning, Dens! This is going to be a good day!" - his busty betrothed announces.

"How do you have so much energy...." - he complains, rubbing his eyes.

The teacher stretches and gets up, ready to seize the day.

"I slept so well last night! Since coming here my sleep has been fantastic." - she says, starting to get ready for work.

"I'm glad for you... I basically passed out. Ugh, so tired." - he rumbles, sitting up.

"You are getting old, Mr. Tired-pants!" - she giggles, leaving the bedroom.

She hears Dennis grumble something but pays no mind, nothing will ruin her day.

Why is our young naive protagonist so enthusiastic? The teacher simply had a good feeling about all the new possible opportunities.

'Yes, it's true I've been getting into 'delicate' situations lately, but today is not going to be like that. Today is going to be fun and free of accidents!' - she decides.

~~~

Lana's Rousing

Well, readers, as you know, Lana grew up boringly conservative. Extremely so.

However, as a teen and a young adult, instead of firmly believing the lessons her family, friends and church implanted on her, she simply learned how to push her desires deep inside.

She became a master of suppressing her sins.

Young Lana did not change her thoughts, she learned how to control them.

She didn't know why, she only knew it was not proper, but in the abyss of her psyche, she felt them stirring. Waiting to be woken up.

A looming wild fire of lust.

A craving for sexual freedom.

A hunger to experience the pleasures of flesh.

A thirst to let her inhibitions loose.

She knew she had slipped a few times in the past, with the occasional masturbation or mutual touching with one of her two partners, but she dismissed those incidents as 'necessary' to keep her inner demons at bay.

The events of the last 12 days were hot in her mind, and she knew she needed to curb them, it was what was required and expected of her, right?

That is what she decided to do from now on. Of course, she would fail, miserably.

You see, unfortunately for our dear heroine, it's almost impossible to put the toothpaste back into the tube. Her hidden sexual monsters were already too unruly to ever be tamed again.

Today was going to be the start of a steamy new page for our Naive Teacher.

~~~

She starts to prepare breakfast while humming a tune. Her fiancee comes into the kitchen, dressed and ready for business.

"What has gotten into you?" - asks Dennis grumpily, serving himself fresh coffee.

"Ah, nothing. Just ready to get stuff done!" - she flexes her muscles. He groans.

She fixes up some eggs with sausages and sits down with her future husband to enjoy the meal.

"I know we are going to Jack's house tomorrow night, but will there be another team event on Saturday?" - Lana asks curiously.

"Yeah, we're having a dinner party at the Hunters. Lucius plans to announce our new project." - he explains, midst sip.

"That will be fun. Also, I have a school trip on Saturday morning. It's mandatory." - she says.

"Oh, score, I get to sleep in!" - he cheers, she giggles. "Where are you going?"

"To the beach. I am their chaperone, and we will have a biology lesson." - she explains.

"Hmm... please make sure to wear a conservative swimsuit since I'm not around." - he asks.

"Of course, dear. Last time I wore that one just for you." - she reminds him.

"Be careful, these kids are pranksters and naughty. Out of control, the lot." - he says worriedly.

"I am a big girl, I know how to take care of myself, Dens. Do not worry." - she assures him.

"Okay, I trust you, babe." - he says getting up. "Thanks for breaky, 'twas delish." - he compliments.

"You are welcome. Love you and have a good day at work!" - she says, giving him a quick peck.

"Love you too." - he says grabbing his work stuff. "Ah, also I wouldn't mind getting a new selfie today!" - he winks at her mischievously.

"Oh, you!" - she giggles like a schoolgirl and gives him another kiss. "Will see what I can do!"

He leaves for work and Lana goes get ready. She wants to arrive bright and early to get the Physical Checkups out of the way. She quickly showers and does her makeup.

"Ahh... forgot to do laundry again. Lana, darn it, where is your head at." - she chastises herself out loud, rummaging through her drawers.

She finds her "backup to the backup" pair of undergarments. It's an old beige cotton bra with some holes and some old beige 'granny panties'. They were all loose and fugly, but there was nothing she could do.

Still without any clean skirts, she opts for a baby-blue sundress. Again, it was light and flowy, leaving her forearms bare and ending a couple inches above her knees. It also provided a hint of cleavage, but it was still an outfit that would be considered prude and tame by most.

After getting dressed, she grabs a post-it and writes "DO LAUNDRY!!!", attaching it to the fridge.

Her phone buzzes with a message notification.

"Ah, I should check it. It is still early, I have over an hour to get to work." - she tells herself.

Message -- 07:04 -- Cox Friends

* PB-Justin -- Morning sunshine!

* Lana -- Morning, boys.

* CoolPaul12 -- Hello gorgeous

* Noel Murns -- Good morning, this is Noel.

* Lana -- I know! *lol*

* PB-Justin -- We really liked the pic yesterday

* CoolPaul12 -- And we heard Dennis enjoyed himself too *wink*

* Lana -- Well, he didn't approve that I sent it to you guys!

* Noel Murns -- Right, you should send it directly to him from now on. But we can help.

* Lana -- Ahm? What do you mean Noel?

* PB-Justin -- We thought we could do a 'daily selfie' thing

* CoolPaul12 -- It's a very popular thing online!

* Lana -- Ah, yeah. I think I saw it on Insta.

* PB-Justin -- So how about you send Dennis a photo daily?

* Lana -- That's a good idea, but Noel said you guys can help?

* Noel Murns -- Correct, we don't want Dennis to get bad photos.

* CoolPaul12 -- Or, heavens forbid, get bored of them! *shocked*

* Lana -- Yeah, I wouldn't want that.

* PB-Justin -- so we are on the same page then

* Lana -- I guess we are? *confused*

* CoolPaul12 -- Great, so you should send us 2 or 3 pics and we can help you choose the top *up*

* Noel Murns -- Ensure it stays fresh for Dennis.

* PB-Justin -- He'll love it!

* Lana -- Erm, I promised Dens I would avoid sending you naughty selfies!

* PB-Justin -- You're not sending us pics, you are just asking the Cox Friends for their opinions

* Noel Murns -- Who better than us, Dennis' male coworkers, to help you figure it out.

* Lana -- But you will still have the pics in your photo gallery!

* CoolPaul12 -- We promise we won't save them, we'll just look at them in the chat

* PB-Justin -- That way, we won't have them

* Noel Murns -- Yes, only Dennis will have the pics, so it seems fair. We are just helping you.

Lana looks at the clock, a few minutes have passed, this was taking too long.

Message -- 07:09 -- Cox Friends

* Lana -- Okay, I have to go now. I'll think about it!

* Noel Murns -- Have a good day, Lana.

* CoolPaul12 -- Nice, maybe snap a pic of something other than your bra

* PB-Justin -- Don't forget to up the ante! TTYL!

* Lana -- Bye, guys.

'I guess they would just be helping me pick a good photo. And Dens asked me to avoid sending a pic of my bra, so something else would be reasonable, like Paul suggested. Hmm, maybe if the opportunity arises.' - she decides.

Lana quickly grabs her purse and teaching materials, and leaves for school.

~~~~~~~

Early Morning -- Lilly

Lana is almost at the sidewalk when she hears someone calling for her.

"Lana, dear!" - says a high voice from behind.

She turns and sees Lilly, her neighbor, waving at her.

"Hi, Lilly! Sorry, I have to go." - shouts Lana.

"Don't worry, it'll be quick. Come here!" - her neighbor motions.

The teacher makes her way towards Lilly.

Lilly was Jack's wife, she was in her late 30s and still pretty, albeit slightly out of shape. She was fun, easy-going and extroverted. She had a cutie 5-year-old son named Evan.

Lana really liked Lilly, although she could be a bit too perverted and exhibitionist for her liking.

"Hi, neighbor!" - the wife greets again.

"Hi. Sorry, I can't be late to work." - Lana explains the rush.

"I have a proposition for you, won't take long." - Lilly smiles.

"What can I help you with?" - the newbie teacher asks, unsure.

"Well, how about we end the stupid bet with just one more quick pic?" - the neighbor asks.

"Oh, even though I owe you two?" - she asks, trying to keep it cool. 'Score!' - she thinks.

"Yeah! Come on in." - the housewife sees the worried look on the young fiancee's face. "Don't worry, ten minutes tops!" - she assures her.

"Okay, I guess I can afford 10 minutes." - Lana agrees.

Both women walk in and make their way to the living room. There is an old man sitting on the couch taking care of Evan.

"Lana, this is Jack Sr., Jack's dad. He sometimes comes over to see his grandson." - Lilly introduces.

"Oh, hello. I am Lana Cox, Lilly's neighbor." - Lana greets him.

The old man gets up to greet the beautiful newcomer. He looks very similar to Jack, ugly, with the same short and overweight build, although he is in his mid-60s with balding wispy white hair.

Both Jacks look a bit disgusting to be honest. Lana questions momentarily why Lilly was with her husband, when a flash of Jack's thick penis flashes in her head, making her blush.

"Greetings my dear, it is very nice to meet such a beauty!" - he greets, kissing her hand.

Lana giggles. He even had similar mannerisms to his son.

"Is your husband not around today?" - Lana asks her neighbor.

"No, he had work to do. Important things or whatever." - Lilly rolls her eyes.

"Well, I'm sure the two ladies have matters to take care of, I'll leave you to it." - announces Jack Sr., sitting back down on the couch with Evan.

"Oh, dad, I thought you could help us take the images." - says Lilly.

"Lilly... but the photos... erm..." - stammers the young neighbor, embarrassed.

"Don't worry, pumpkin. Lils here told me all about it." - the old fat man clarifies.

"You did?" - she asks the neighbor, shocked.

"Of course! And we even showed him the photos." - she says nonchalantly.

"He s-saw the p-photos? All of them?" - she asks with wide eyes.

"We wanted to get his opinions on the best ones to show tomorrow night. You wouldn't want us showing them to strangers, now, would you?" - Lilly asks rhetorically.

"Erm... I guess not..." - Lana says. 'Oh, so it is common to ask others' opinions on photos... hmm... the guys were right...' - she reflects.

"I have to say, a marvelous job. You are a wonderful model, Mrs. Cox, your husband must be proud." - the senior man says.

"Thanks! Oh, and it is Miss Cox. Dennis is only my fiancee." - she clears up.

"I see, shame that a radiant flower like you is not married. That boyfriend of yours should hurry before someone snatches you away, pumpkin." - the elderly man laughs.

Evan laughs too and starts yelling 'Punkin' 'Punkin' 'Punkin' repeatedly. His mom calms him down.

"Aw, thanks." - Lana giggles embarrassed by the compliment. "If you do not mind me asking, why are you calling me pumpkin?" - she asks curiously.

"Ah, because you are carrying two big ones, right there." - the old man grins, pointing at her ample chest. He chuckles when Lana makes a mortified expression.

"Ignore this lecher, Lana." - Lilly says, slapping him lightly. "About the photo, it was Kenny's idea, but it was a good one." - she explains.

"Kenny is super nice. What did he suggest?" - Lana asks, intrigued.

"A picture of you showing your asshole." - the motherly neighbor says casually.

"Gasp!" - the buxom young woman gasps. "M-my a-anus?" - she stammers.

"Yeah, it's no big deal, we all have one." - the housewife points out.

"Is that not going too far?" - the brunette teacher protests, abashed.

"Come on! You are late for work and this simple photo will get you out of the bet." - Lilly justifies.

"It's a simple bumhole, not very enticing." - Jack Sr. agrees. "Shame to let such a good opportunity go to waste on such an irrelevant part."

"Hmm... yeah... I do not see the point in that hole... but, still... it is too intimate and improper." - Lana says, visibly rose-cheeked by the prospect.

"You don't see me complaining, Lana. If I recall, in the last photo you took, my husband's fat hog was inside your pretty little mouth." - the small breasted neighbor says woefully.

"Sorry Lilly! I did not mean to upset you, things got out of hand!" - the naive teacher tries to explain.

"I know, it was kinda hot. But still, you also owe me one for that." - the housewife explains.

"I guess I do..." - Lana agrees reluctantly.

"Think of it as killing two birds with one stone. Except this stone is your bootyhole." - Lilly giggles.

"I don't like it, but you are right. As long as we do it quickly." - the newbie fiancee concurs, uneager.

"Okay, let's do this! Dad, get the camera ready." - Lilly commands.

"Ahm... Lilly, can you do me a favor?" - Lana asks halfheartedly. The neighbor nods. "Can you not include the most salacious pics on the slideshow?"

"We have it almost done, but I'll see what I can do. For you." - Jack's wife agrees.

"Thanks!" - she breathes, relieved. 'What Dens doesn't know won't hurt him.' - she thinks.

"Lils, you should take Evan to the other room, he shouldn't witness such a shameful and whorish display." - says the ugly old senior.

Lana feels a stir inside at his bold words.

The young kid starts yelling 'Shame' 'Shame' 'Shame'. Lilly sighs deeply.

"You're right, dad. Lana, please get ready and bend over on the couch with your dress hiked up. BRB." - she instructs, taking Evan to the kitchen.

Her heart beating fast, the youthful teacher bends over the couch, putting her hands on the back cushion and lifting her ass up in the air.

She glances behind and sees Jack Sr. ogling her with a lecherous smile.

'What am I doing... I decided that today was going to be different. Argh. No, Lana. Focus. This is a one-off. You'll pay this stupid bet that your fiancee made and be free of it. Yes, it's a single occurrence, the exception.' - she debates in her head.

"Go on, pumpkin. Lils told you to hike your dress up and expose your bum and underpants." - the hideous potbellied man states.

She makes a disgruntled noise and starts to lift her dress in front of Jack's father.

'He is just ogling me while I raise my dress... ugh... am I really going to show my anus to them? At least Dens won't see the picture. And it's just an orifice, it's not really a sexual organ. Anuses are common and everyone has them. It's not proper of me to do this, but it could be worse.' - she deliberates.

The teacher bunches her dress at her waist, revealing her full creamy butt, covered by a pair of beige granny panties.

"Goodness me, pumpkin, you are plump. What a big booty, I love it." - the old letch compliments.

Lana blushes and opens her mouth, ready to reply, when Lilly comes back to the room.

"Everything set? O..." - she trails off when she sees the raunchy neighbor on display. "Lana dear, what horrible panties!" - she proclaims.

"Ah! I forgot I was wearing them!" - the half-naked fiancee exclaims. "I forgot to do laundry."

"Oh, well. It's not ideal, but we'll work around them somehow." - Lilly shrugs.

"What does that mean?" - the naive brunette asks anxiously.

"I was planning to move them to the side, but they're too bulky and ugly. So, we'll have to lower your panties down a tad." - the neighbor's wife explains nonchalantly.

"Gasp! No!" - Lana gasps, her chest tightening and getting hot.

"You said you were late, so we don't have time, let's do this quickly, no complaining." - Lilly chastises the teacher.

Lana glances at the clock, she was still good if this ended soon.

"Ugh... fine... quickly..." - she answers sheepishly, closing her eyes in apprehension.

Lilly approaches her, and unceremoniously starts to pull her panties down her peachy butt. She continues pulling them until her tight, pink asshole comes into view.

'Oh, my, goodness... she is going to expose my anus... oh... no... it's out... stop... don't keep going, don't let this old man see my cooch...' - she begs in her head, starting to get secretly aroused.

Lana holds her breath, fearing for the worse, but the neighbor doesn't go any further, letting go of her undergarments. The busty fiancee breathes a sigh of relief.

"There ya go, it's beautiful. So tight and small. I can see that your asshole is unused." - Lilly comments.

Lana blushes and feels a wave of excitement emanate from her vagina.

"Ready when you gals are." - Jack Sr. comments with lust in his voice.

Lana glances at him and sees that he is adjusting his pants for the boner that is rapidly forming. She gasps quietly.

'Oh, my... he is getting worked up just seeing my bare butt and anus... I wonder if he is as big and thick as his son... no don't think about that... let's end this fast.' - she reflects.

"Is this okay, Lilly?" - Lana asks submissively, arching her back a bit and emphasizing her posterior.

"This will do, I guess." - the housewife answers dismissively. "Dad, please snap a pic."

He grins broadly, showing his yellow crooked teeth. He focuses the camera and takes a picture. He shows it to Lilly who makes a displeased sound.

"Ah, take another one. You zoomed too much on her butthole. You need to show her face." - Lilly orders. "Lana, babe, turn your face to the camera, and don't look so distressed."

With a slight nod, the bootylicious neighbor turns her head and smiles to the lens. It looked very out of place, her butt and asshole out for all to see while she beams happily.