Naive Teacher in Winston Ch. 01

(This is an edit to Chapter 1)

Foreword

Everyone in this story involved in any sexual activities is at least 18 years old.

This tale is not real and probably could never be real in 2021, so any correlations with real-life are mere coincidence.

This story is a slow burn, so don't expect sex or very explicit content early on, it is mostly about the slow corruption of a naïve young lady. Main themes include exhibitionism, teasing, groping, virginity, naivete, corruption, light cheating, netorare, abuse of power, pranks and more.

Also, please keep in mind that English is my third language and I do not have an editor for the time being, so please be patient with dear ol' me.

This story is inspired by games like "Succulence", "The Humbling Experience", "Agent Alona", "Mischief Wars" and many others, and stories like "Miss Nishida Motivate the Boys", "Just One of the Guys", and other Lit stories.

This first chapter is lengthy and contains a lot of introductions and setup, including the first day in town. Hopefully this is the first chapter of many, since I currently have until Day 22 sketched out.

Enjoy the read,

~ Potato Head

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Prologue

Lanette "Lana" Cox, future Mrs. Laywood, was very excited. She had just arrived in Winstonstead, at her beautiful new house, with her handsome fiancee, Dennis, and with a brand new job to boot.

Before we continue with the present, let me elaborate on the backstory of our heroine.

~~~ Lana grew up in a very religious family in a medium-ish sized town on the Midwest of the US. She was the third sister of four and was always the shy one of group.

She grew up relatively wealthy and sheltered, so her experiences were very limited. Lana never left her home town until now, so y'all can have an idea of whom we are dealing with here.

She was a Biology major with emphasis in Education, since her dream has always been to become a teacher. After graduating college, she had a few jobs and eventually became Teaching Assistant at the local college, where she met Dennis, who was a year older than her and was doing some computer courses.

Lana was 26 when they started dating, and after a couple months they were madly in love. They were both from religious families and complete inexperienced virgins, promising to wait until marriage. Well, actually, Lana promised to wait until marriage, to the chagrin of Dennis, who tried and tried to convince her to no avail. In the end he was happy with what he could get.

The reason why Dennis was so patient? Lana was a knockout. She was 5'3 (161 cm), medium-length light brown hair, big green eyes, a curvy body with an ample bust (38 DDs), and an ever bigger ass. She was THICC, but in good shape, since she went to the gym religiously. It was basically her second church, focusing a lot of the attention on her flat stomach, toned legs and juicy butt. Squats city baby. She was also oblivious to the ogling of the other gym regulars.

It may seem strange that Lana was shy and virgin, and yet took care of her body so much. Well, that transformation started when she was 24 and met Chad, her previous (and only) boyfriend. He was a gym rat and let's just say that he implanted some ideas into Lana's head about what men wanted. She has been taking care of her incredible body ever since.

Quickly describing Dennis, he was tall, at 6'1 (185 cm), and had a nice face, too soft to be consider manly, but not girly either. He had a curly mane of ginger hair and fair skin. He was at the same time skinny and out of shape, with a slight belly from years of sitting on his computer.

Dennis didn't waste much time, and 4 months into the relationship he proposed to Lana. She was ecstatic. And so were her parents, after all, Dennis Laywood was from a good conservative family with a solid job and an even more solid reputation. He could relieve them from a lost cause of a daughter, one that seemed destined to stay single her whole life.

The couple started planning the wedding and preparing to move in together to start a family. However, things changed when Dennis got a huge promotion at his company. The caveat was that the promotion came with a relocation package to the firm's headquarters. He was happy to accept the offer, as he longed to get away from his current work environment where his co-workers made fun of him and called him Penis (saying it like Dennis but with a P) and teased him about his sexy girlfriend. All he wanted was a brand new life with his hot new bride-to-be.

Dennis worked for Winston-Phillips Co, a very traditional company involved in Trading, Transportation and Cargo, founded over a hundred years ago. The company had a lot of subsidiaries that handled most of the "grunt work", with the headquarters being largely the brains of the operations and where the money was. Winston-Phillips Co HQ was located in Winstonstead, somewhere on the middle of the US, and they both belonged to the Winston-Phillips family, a very rich, old and white family.

Lana knew that Dennis' job involved something with computers, but beyond that it was all above her head. Don't get me wrong, Lana was very smart, but only on certain subjects and situations. She was great at studying, biology, teaching and much more... but lacked common sense and a wide range of knowledge.

After she and Dennis started organizing their move, she applied for a teaching position at the local school. Apparently it was a really good private school, everyone was at least 18 years old, exclusive to Winstonstead citizens, and mostly focused on life lessons and good habits, like Finance, Taxes, Sex Ed, Art and Technology.

Lana was confused when she received a call back from the Principal's Secretary asking for different types of photos of her (including one in a swimsuit), but she was assured it was common practice, so she obliged and sent lots of photos from her phone (all very conservative).

The old Principal was more than happy to offer her a job once he saw her photos, and called her the next day offering a position of Biology/Homeroom/Women's Gym/Support Teacher. She questioned him about all the different roles, but he mentioned that teachers there needed to wear "Many Dresses". She was even more confused since the expression was "many hats", but she happily accepted the offer. After all, it meant she was going to live with Dennis all by herself in a new town!

Winstonstead, simply called Winston by its inhabitants, is a small village of 150-200 people, most of which work for or around Winston-Phillips Co. The village almost looks like one big campus, with a school, a place for kids, a clinic, a church, a small police station, a diner, a grocery store and a couple small shops to serve the locals. It was a very traditional place with old generational families and people connected to the Winston-Phillips household. It was extremely hard to "get in".

Outsiders were a novelty, and soon Lana and Dennis would learn that.

~~~

Back to present day, Lana Cox, now 27 years old, and Dennis Laywood, almost 29, had just arrived at their brand new 4-bedroom 2-story house, including a backyard pool, with lots of spaces for kids, pets, parties, and anything the couple's heart desired.

It was around 6pm already when they started unpacking the Minivan, with most of their things having already been delivered and placed inside by the moving company.

Two hours later, Lana was bringing in her last box when she saw her next-door neighbor, a balding man in his mid-forties. She waved with a warm smile and he waved back. As soon as she turned her back, he picked his phone, took a series of quick snaps and started texting.

"Dens, last box finally!" - exclaims an exhausted Lana as she passed by him.

"Oh babe, watch out, your panties are showing above your Jeans!" - he says.

"Ooops" - she says pulling up her pants to cover her pink lacy panties, hoping that the neighbor didn't see anything.

They had a quick bite to eat, Dennis whipped them a couple sandwiches while Lana showered the day-sweat away, and they settled down in bed after a small routine.

"I am looking forward to tomorrow, to walk around and meet some of the people of Winston!" - says Lana excitedly.

"Me too love, me too. Hopefully I can meet some work colleagues too, I only talked to them via Zoom or chat.... ahhhh..." - yawns a tired Dennis.

"Let's get you to sleep then, it was a long day." - she says concerned.

"Ahh... tsk... was hoping we could fool around a little bit." - says him with disappointed on his voice.

"Control yourself mister... we will have plenty of time for that after we get married!" - Lana says teasingly with a smile.

"Oh you!" - laughs Dennis giving her a quick peck on the lips - "Okay let's go to sleep, goodnight my love."

"'Night, I love you." - says her warmly as she turns off the bedside lamp.

~~~

Interlude --- Winston Secret Chat Group

"Guys you won't believe Dennis' wife! She is fucking stacked" - typed Jack. "She can't be that hot!" - said someone. "Yeah I doubt it!" - said another. "Well, here is a pic of her ass so you all can shut up" -- said Jack sending the pics he took. The pictures framed her big butt perfectly, including a nice view of her lacy underwear. "Oh what a big ass" - said one person. "You can even see her sexy panties" - said user RoGer. "Would love a round with that butt" - said a different resident. "You and your tiny limp dick!" - mocked LukasTTT. "Gentlemen, calm down, let's take this easy and we can have some fun." - said someone called 'Rich4', emphatically putting an end to the topic.

~~~

Day 0 -- Sunday

Daytime

The sun shines brightly as the loving couple wakes up. They cuddle lazily in bed for a bit and get up to do their morning routines. Since it's Sunday, they take it easy. While they are having breakfast Dennis suggests they take a walk on the village since is so hot and nice outside.

Lana is putting on her usual blue jeans, when Dennis walks by.

"Oh babe, how about a summer dress? It will give a good impression to everyone." - he suggests.

"I am not sure, isn't it a smidge inappropriate?" - she asks shyly.

"Nonsense, I want to impress my new boss Lucius with my beautiful bride!" - he beams. - "We will meet him early afternoon."

She blushes and happily obliges as she puts on a knee-length yellow sundress that hugs her curves and ample bust nicely.

~~~

The couple leaves their house after lunch and go stroll around the main plaza, the open area surrounding all the main buildings of the village. As they start walking while holding hands, lots of people start gathering to see the new residents.

They pass by the neighbor that Lana saw and stop by to introduce themselves to him. He is sitting on a bench leisurely reading a newspaper.

"Good day, I waved to you last night!" - says her.

"Oh dear, I remember! I am Jack, your left-door neighbor, nice to meet you both." - says the balding man as he gets up. He is wearing a blue t-shirt and a grey sweatpants, very casual.

"Nice to meet you too, I am Dennis and this is my fiancee Lana." - motions Dennis towards Lana while shaking Jack's hands.

"Lovely to meet such a fair and lovely flower..." - says Jack embracing Lana with a big hug. She makes a dumbfounded expression.

"Erm... thanks..." - squeaks Lana.

"Oh right, sorry about that, it's common here in Winston for people to hug when greeting. You are prudes from the city, so I can see that you were taken aback, my apologies to the beautiful lady." - says Jack very elegantly.

"Oh don't worry about it Jack, we are neighbors and probably co-workers, hugs seem like an appropriate greeting." - intervenes Dennis as he didn't want to cause any issues on his first week of work. Jack grins at that remark.

"Co-worker! That is right, I forgot... let's talk about it for a bit then. Dear, why don't you sit down for a second, this shouldn't take long..." - motions Jack to the bench as he guides Lana with his other hand, placing it on her lower back.

Lana recoils at the stranger's touch, but sits down. Jack and Dennis dive into a complicated conversation about work while Lana reflects on what had just happened.

She had just hugged a stranger and then he touched her, should she be worried? Probably not, it seemed innocent and a custom of the village. Yes, they are new, they will take a while to learn all the ropes. It's okay, it was harmless.

As her thoughts focus back on the two men in front, her eyes are drawn to a big bulge on Jack's sweatpants. It was just a couple feet from her face. She quickly turns away. Jack looks at her and smirks. "This might be easier than I thought..." he ponders.

Her mind was once again in turmoil. How could it be so big? What was she thinking. No. Dennis was her fiancee. Besides, she never saw a "peepee" before, it could be just a sock. Yeah definitely, that is what it was. She keeps stealing glances at the sweatpants, too stunned to fully look away.

At this moment Jack shakes Dennis' hand and walks away. An illusion was broken, and Lana immediately gets up, visibly flushed.

"What happened?" - asks Dennis.

"He had a big bulge in his pants..." - whispers a red Lana.

"Hahaha, nonsense, it was probably his phone." - dismisses Dennis.

~~~

They continue walking and her mind keeps racing. She never had sex, but she touched a peepee before, as she calls them. Two peepees to be more exact. Dennis' and Chad's, her other boyfriend. She never saw them, she only touched them in the dark. She also did what Chad referred as a handjob, but she didn't like the experience, it ended up with semen all over her chest, gross. She performed a handjob for Dennis too, but only after a couple months of dating on Valentine's Day. She knew Dennis was impatient about having sex, so that seemed like a good one-and-done compromise at the time.

She keeps thinking about Jack's bulge, it looked notably bigger than the other ones she touched. Maybe it was just a wallet, yes, that was probably it. She shakes her head to keep the nasty thoughts away as she keeps on with their stroll.

"Dennis, you are finally here!" - states an imposing voice. They both turn to greet the stranger.

"Hello Lucius, glad to finally meet you in person." - says Dennis to a clean-shaved well-dressed man in his early forties. He had short brown hair, piercing blue eyes and was movie-star handsome.

"It is about time you decided to come to Winston, it will be great for your career!" - says Lucius as he shakes Dennis' hand. He then turns his head towards the beauty next to him. "Oh, this must be the fiancee that I heard so much about. You didn't lie Dennis, she is a stunner. Lucius Hunter, pleasure to meet you..." - compliments Lucius as he opens his arms waiting for a hug.

She shyly obliges and hugs the stranger.

"H-hi, n-nice to meet you, I am Lana." - stammers her as the embrace ends. She feels his hand slightly brush the top of her ass cheeks, but dismisses it as a mistake.

"Very nice, I see you are already aware of the customs of Winston. Also, wonderful choice of clothing, very free flowing, modest and pretty. Come, come, both of you, I have much to show you!" - says Lucius as he guides them around the small village.

He gives the young couple a tour, pointing out the numerous company buildings, the school and other necessary places, like the grocery store. Every time he points at a place, he touches Lana with the other hand. Sometimes on the shoulder, others on the small of her back and once even at her hips, meeting her panties. She flushes every time.

After what felt like forever, Lucius says his goodbyes to them. She feels something big poking her flat tummy during the embrace, but pays no mind to it.

~~~

They met and were introduced to numerous people during the day, with Lana being made to hug every single person they met, including the women. There were so many that she barely remembers any names, except for Roger, one of the teachers at the school. She remembers him, because his hug was tighter and took notably longer than any others, and he kept ogling her chest the whole time. The nerve.

She also remembers Benjamin, who apparently was one of the 18-year old students in the school. She remembers him because while she was saying hi to his parents, Benjamin lifted her skirt exposing the bottom of her bubble butt and her yellow cotton panties for everyone around to see.

Needless to say, she turned beet read and held her sundress the rest of the day.

"Dens, I don't know if I like this, everyone hugged me so much and touched me. Also they saw my panties! This is weird." - says a worried Lana quietly.

"Ah don't worry babe, everyone is super friendly here. They are all super close too. It's all harmless." - reassures Dennis.

"Okay, but I don't really like whe-..." - starts Lana.

"Don't make a scene, this is my first week of work, I need to impress everyone and we need to get used to the culture of this village. Let's embrace it and be happy! - suggests Dennis enthusiastically.

Lana's nerves subside with Dennis' loving words. He always had a way with her. In the background she sees an older gentleman accompanied by two young people of opposite sexes.

"Lana, that is Mr Winston-Phillips, the President of the company and also the Mayor of Winston." - whispers her fiancee.

The group approaches the couple with warm greetings.

"Good afternoon, you must be the Laywoods, I welcome you to Winstonstead, my family's home town. Enjoy your time here. Mr. Laywood, I heard great things about you from Lucius." - greets the old man.

"T-thanks a lot Mr. Winston-Phillips, I hope I won't disappoint." - stammers Dennis. "I am Dennis Laywood and this is my fiance, Lana Cox."

"Oh, I see, not married yet. Well, does not matter. Come here my dear and let me greet you properly." - motions the old man for Lana to come closer.

"Hello Mr. Winston-Phillips, nice to meet you..." - starts Lana.

"Nonsense. Please call me Dick, short for Richard. Only friends can call me that." - smiles the old man as he opens his arms for a hug.

"O-okay Mr. Dick..." - wavered Lana as she embraces the President/Mayor. The hug doesn't last long, but Dick shows a puzzled look on his face.

"Where is my kiss? Did Lucius and the others not teach you Winston's culture?" - questions him.

"Oh sorry sir, they explained that men and women hug when greeting each other, that is what I did." - answers a flustered Lana.

"Call me Dick, not sir. Yes, that is indeed the polite manner, however, when meeting someone older than 60, it is customary for the woman to give the man a kiss on the cheek." - explains Mr. Winston-Phillips nonchalantly.

Lana was visibly shocked and starts blushing furiously. She looks at her fiancee for reassurance, but he is eager to please the President of the company and gives her an encouraging look.

Reluctantly, she bends slightly forward and gives Dick a quick peck on his cheek. She smells very delicately of flowers and provides him with a front-seat view of her hidden cleavage, normally concealed by her prudish dress.

He laughs out loud at the attempt. "Do not worry, I understand you both are prudes, but we are a tightly-knit group of people here in Winston. Hugging and kissing will become habit soon enough." - says the old man. "Thanks for the kiss dear, and I will be watching your progress Dennis, we have high hopes for you." - he finishes.

He starts walking away and waves to his two companions to follow him. The couple had no idea who they were.

"T-thanks Mr. Winston-Phillips, w-we won't l-let you down." - says Dennis trying to sound confident but failing miserably.

The couple makes their way back home. The whole way back, Dennis sang Lana's praises for dealing well with Dick.