Naive Teacher in Winston Ch. 03

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Upskirt, kisses, moaning and Sex Ed class.
8.8k words
4.62
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Part 3 of the 18 part series

Updated 03/28/2024
Created 12/16/2021
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(This is an edit to Chapter 3)

~~~

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 2021, so any correlations with real-life are mere coincidence.

This story is a slooooow burn. And still no editor, sorry about that.

This is the third chapter of the misadventures of a Naive Teacher. It is strongly suggested that you read Chapters 1 and 2 first.

This chapter contains the following School days schedule:

* Day 2 -- Morning: Free --- Lunch ---- Afternoon: Homeroom --- Clubs: N/A (Week 2 onward)

* Day 3 -- Morning: Bio --- Lunch --- Afternoon: Bio Lab --- Free

Enjoy the read,

~ Potato Head

~~~~~~~~~~~~~~~~~~~~~~

Day 2 -- Tuesday

Morning

The sun shines bright as Dennis' alarm goes off indicating it was time for the couple to wake up.

Dressed in just a short robe with a pink slip underneath, Lana goes to the kitchen to prepare breakfast. She cooks scrambled eggs, toasts a couple sourdough slices and puts on a fresh batch of dark coffee.

The young fiancee didn't have time to reminisce about the previous day, she just went into cooking-mode to get everything done for her lover. The teacher is just finishing putting the food on the table when Dennis shows up, ready for work.

"Thanks for breakfast, hun! Can you please do me a favor and get me the mail? I am waiting for some important documents, and I can't be late for work." - asks her husband-to-be.

"Erm, I am not wearing much... what if the neighbors see?" - whispers a worried Lana.

"Hahaha, you are covered enough, besides, it's hot outside so it doesn't matter. Thanks babe!" - Dennis replies, digging into the food. "This is delicious, you are amazing!" - he compliments.

Feeling giddy with her fiancee's encouragement, she walks to the front door to pick the mail. She glances quickly at herself in the mirror on the way out. She frowns.

Her robe is short, stopping about a hand above her knees, and her slip is shorter still, not going much further than the bottom of her bubble butt. The robe is not tightly shut as her big breasts won't allow for full closure, giving anyone a nice view of the top of her slip and the slight transparency it provides. You can distinctly discern the upper part of her tits through the sheer fabric.

'I am not decent... ugh... I'll be quick, Dens said it was okay.' - she thinks.

She opens the door and quickly walks towards the mailbox, all the way at the sidewalk. She collects everything inside without looking. Lana is already halfway back to her porch when Jack's door opens.

"Morning, neighbor! Nice and sunny today, huh!" - the overweight neighbor greets with a wave.

"M-morning, Jack. Listen, I have to go..." - Lana starts to explain.

"I just remembered, my wife Lilly and our son Evan are out of town at her parent's this week, but they told me they really want to meet you." - he interrupts her.

"Oh, that is nice, I didn't know you were a dad!" - she says, feeling more trusting of Jack. "I want to meet them too, when are they back?" - she asks the balding neighbor.

"Friday, so a few more days. Come here, let me show you a photo..." - he waves at her to come.

The naive Lana is feeling a little self-conscious due to her outfit but knowing that Jack is married helps set her mind at ease.

The wife-to-be crosses the imaginary line that divides their properties and walks towards his porch. He holds his phone up, motioning for her to stand next to him.

"Look, isn't Evan so handsome? Smart too!" - he says proudly.

She sees the photo of a smiling young kid next to a woman in her late 30s, who looks exhausted.

"Indeed, he is a cutie patootie. How old is he?" - she asks, intrigued.

"Just turned five last month!" - the neighbor beams with satisfaction.

"Oh, I am looking forward to meeting them soon." - she replies. His face lights up at that remark.

"Brilliant idea! We can take some photos now and I can send it to them, that way they get to meet you." - he says matter-of-factly.

"Oh, sure, that seems reasonable. We just have to hurry; I need to bring Denn..." - she starts to explain.

"Okay, okay, come closer...." - he says, opening his arms and putting his hand behind her shoulders. "Smile!" - he says taking a couple photos.

Jack looks at them and makes a sour face.

"What is wrong with the photos?" - she asks curiously.

"Too many clothes, can't really see you clearly. Can you open your robe? They need to get to know you well!" - he insists.

"O-open my r-robe?" - says Lana, taken aback by the request. "Is it necessary?" - she asks unsure.

"Of course! How else are they supposed to get to know you? It's harmless, we're both wearing sleeping clothes." - motions him to his tank top and small shorts.

She looks at his clothes for the first time and notices a big bulge on his small shorts. They seem more like underwear than pajama shorts. They even have a flap that is slightly agape.

Lana starts to feel a little excited by the thought of Jack's bulge.

"R-right... we are..." - she hesitantly agrees. He looks at her expectantly.

She unties the knot on her robes and it falls open. Not much extra is showing, except now it's easier to have an idea of the shape and size of her ample breasts and have an unobstructed view at her creamy thick thighs.

"Perfect! Lilly will love these!" - says Jack putting his arm around her again and taking a ton of selfies.

The balding man keeps slightly moving and turning while making different faces. The naive fiancee follows his lead.

Suddenly, Jack stops taking photos and looks down at himself. His arm is still ready to take more selfies.

"Oops, don't look!" - he says with a grin.

Lana instinctively looks down and sees that the flap of his shorts is open, the head of his penis poking out slightly. The dark red is a clear contrast against his underwear.

She holds her breath, feeling herself blush profusely. She can't take her eyes away. It's the first piece of a penis she sees in person.

Her nipples harden, her mouth is agape, and she starts to feel warmth between her legs. She stays quiet, fascinated by the sight.

Not missing the opportunity, Jack starts to take a ton of photos. The teacher's poky nipples are obvious on the photos, making a distinct mark on her robe, as well as her red cheeks and head tilted down. It's clear to anyone looking that she is staring at his big dick poking out.

He smirks looking at the innocent young fiancee admiring his penis. He is proud of his thick 7.5 inches when hard, but right now it's soft and she still seems impressed.

Her mind races while Jack takes pictures.

'Oh my god, a peepee... well you can't really call that a peepee, it's more like a penis. So manly. What I am thinking.... It is so big.... No wonder his bulge is huge. Hopefully Denn's is as nice and large. I mean, it didn't feel as big, but maybe. If I touched Jack's I could compare. I mean, I wouldn't, I have Dennis... Right... Oh no.... I am staring. Lana, stop it! Stop looking at the big penis.'

"Last photo... and done!" - he announces. "What's wrong dear?" - he asks.

Lana is looking at him bewildered.

"Y-your p-penis is out..." - she says embarrassed while pointing at it.

"Oops, my bad. Thanks, dear, for the heads up, we wouldn't want anyone to see it right?" - he says, not moving and leaving it exposed.

"No..." - she whispers.

"Unless you want to see it again, of course. I can show you another time." - he says happily, trusting his hips very slightly.

"Oh... erm...it's still out!" - she stammers.

He laughs and adjusts his underwear.

"Better now?" - he asks. "Thanks for the photos! They will love it. I'll send you some too. Bye now and have a good day!" - he turns and goes inside, not waiting for an answer.

"H-have a good day!" - she says before the door closes.

~~~

She stays there for a second, regaining her composure. What had happened. Why did she think that? What was wrong with her? Maybe it was something she ate. She had seen a real-life penis and it had been so close to her.

Her mind keeps wandering when she hears the door to her house open. She looks at it startled.

"Babe? What is taking so long?" - asks Dennis worriedly.

"Oh, sorry, I was just talking to Jack. Here is the mail." - she says, handing him the pile of letters.

"Too late now, can you take them inside? I have to go. Why is your robe open?" - he asks. She blushes. "Never mind, I'm almost late. Have a good day, babe!" - he gives her a peck and leaves with his bags.

"Have a good day, Dens!" - she says absentmindedly.

After he leaves, the busty fiancee goes back inside, still flushed and with her heart beating a hundred miles per hour. She starts to clean up and get ready for work, but all she can think about is Jack's penis. Needless to say, she didn't get much done that morning.

As she is putting some clothes away, she receives a message from Mary Hunter, her colleague, asking Lana to join her for lunch at the school cafeteria. Noon sharp. She agrees.

She puts on a long sleeve blue blouse and a skirt, foregoing the tights and jacket from the day prior, as requested by Principal Bill. She opts for yellow lacy panties and a matching cotton bra.

As she is about to leave, she receives a message from an unknown number.

Message -- 11:30 -- Jack

* Jack -- Hi Lana, this is Jack. Got your number with the school, hope you don't mind.

* Lana -- Hi Jack, I don't mind, it's all good.

* Jack -- Just wanted to send you some of the best photos of this morning. Have a good day! :)

He sends her about 5 photos. Looking at the first she still has her robe closed and is posing next to Jack. Looks nice, although she could have done without seeing the top of her breasts.

The second and third are from after she opened the robe. Lana blushes seeing the photos, as you could clearly make out the inside of her breasts hidden by the semi-transparent slip and her thighs, exposed for all the world to see. She starts to feel hot.

Lana wasn't ready for the last 2. On them she could clearly see herself admiring and ogling the tip of Jack's big penis. Her mouth was agape, and you could make out her pokies on her robe. She never felt so horny in her life before, here she was drooling over another man's penis in a photo.

She stares at the photos for a good 20 minutes, when she suddenly glances at the time and remembers the lunch appointment with Mary. She rushes out the door to school.

~~~~~~~

Interlude --- Winston Secret Chat Group

"Oh lads, I hit the jackpot this morning..." - says Jack, sending a ton of photos from their 'session'.

"Nice!" "Gross dude, I can see your dirty dick!" "Oh, her slip is sexy af..." "Her boobs are huge!" "You can see them through the blouse!" "Fuck me!" "She is hungry for some diiiick..."

"Lol, enjoy!" - says Jack.

~~~~~~~

School -- Lunch

Lana quickly makes her way to the school, trying to avoid as many people as possible. She arrives just in time. The teacher sighs, relieved, she didn't want to be late for lunch with her new friend.

The buxom beauty enters the school and makes her way to the corridor left from the entrance. She enters the first set of doors, marked "Cafeteria".

She promptly sees Mary on a table and makes her way there. Lots of students admire her as she passes. The table has a sign labeled "Teachers".

"Hi Mary! Hopefully I am not too late." - says a tired Lana, breathing hard.

"Hi Lana! Not at all, I just sat down. Let's go grab food." - Mary says, getting up from her chair and guiding Lana towards the line.

Lana can't help but admire her new friend: Mary is well dressed, stunningly pretty, with long blonde hair and seems to behave with proper manners. Lana is glad to have her around to show her the ropes.

All the students call Mary a MILF behind her back, as she always has a nice cleavage, exhibiting her fake C-cup boobs, and wears tight skirts that accentuate her shapely ass. She has an air of professionalism mixed with strong sexual vibes.

"How does the food work here?" - the new teacher asks.

"You go around to the 'food stations' and pick up whatever you want and put it on your tray. It's all free, covered by the town, however, in the end you have to go to the cashier so they can register your ID and what you got." - Mary quickly explains.

"Sounds good, I am hungry!" - says the naive fiancee.

They make their way through the stations and both teachers pick some stuff out, like a couple salads, some fruits and some yogurts. They line up at the cashier to register the items. Lana is the last in line.

There are about 10 students in front of them and the line is moving very slowly. Apparently the front student forgot their ID and they are discussing it with the old lady, who is operating the cashier station. She looks like a grandma around 60 years old.

After a couple minutes waiting, Lana hears a voice from behind her.

"Hey, teach, how is it going? Hi mom!" - says a young voice to both women. Lana looks behind and sees Lukas Hunter, her student.

"Right, I forgot Mary is your mommy!" - says an amused Lana.

"What's wrong with that?" - asks Lukas, sensing the amusement on Lana's voice.

"I didn't mean anything by it.... Mary... help me out..." - says the teacher looking at her colleague for help.

Mary snickers at the situation but doesn't intervene.

"I will show you!" - says Lukas.

He suddenly holds the bottom of Lana's skirt and lifts it up, wrapping it around the waistband. The front stays in place. Her lacy yellow panties come into view as well as her big creamy butt.

This happened quickly, but for the defenseless young teacher it felt like she could see it happening in slow motion. She screamed with surprise.

Due to the loud screech, everyone in the cafeteria turned to look at her exposed ass and panties. Lots of laughter and shouts could be heard from the students.

"Wooo!" "Nice ass" "What a huge butt" "Sexyyyy" "Take 'em off!" "Sluuut"

Lana was paralyzed, she didn't want to drop her tray and make a mess, but the entire school was seeing her bum and underwear.

They were seeing her in a way that even Dennis, her future husband, had barely seen her.

It was only her second day, and here she was, showing all the students her butt. She started to feel hot, wetness forming between her legs, in her secret place.

The desperate teacher looked at Mary, who was still snickering and then at Lukas, who grinned and bolted from the cafeteria.

Lana could hear phones going off and people taking photos and videos. She started to panic slightly.

"Mary, help me!" - pleads Lana, moving a little trying to untuck her skirt, in vain.

She mostly twisted and turned as her hands were busy with the food tray. This caused the opposite effect, as her plump booty was basically shaking lewdly to the young horny eyes of the students.

Mary approaches her and touches the top of her skirt.

"I am trying... he did a good job, stay still!" - barks Mrs. Hunter to the naive teacher. "Turn this way, let me analyze it. Don't move." - she orders.

Mary turns Lana towards the students, giving them an even better view of her juicy ass and her lacy panties. Lana is conflicted, she is feeling embarrassed but horny at the same time.

'Oh, goodness... what is happening, everyone is ogling me... not proper...I am a bad teacher.' - she thinks.

Mary starts fiddling with her waistband and makes a frustrated sound.

"He tucked them in your panties, I will have to lower them a bit to free your skirt." - says Mary nonchalantly.

"B-but... you can't... in front of everyone..." - stammers Lana. Her coochie twitches at the thought.

"It's the only way. It's fine, it's just the students, no big deal." - reasons Mary.

Her new friend doesn't wait for an answer and pulls Lana's yellow panties halfway down her plump ass. Mary stops, deciding not to push her colleague too much. This time.

Lana shrieks but doesn't move. She feels her heart thumping in her chest.

"Wow, your booty is huge Lana. Tell me the secrets of your bubble butt later, dear." - says Mary sounding a bit flirty. She winks slyly at the students watching the scene.

Lana blushes and knows that everyone in the cafeteria has a perfect view of half her butt without any panties. Naked. Her breath quickens and her mind races.

'Oh my... everyone is seeing my bum... without panties... I am getting so wet thinking about it. Am I enjoying this? It can't be, it is probably just embarrassment. Yeah... that is it. No... I am as hot as when I saw Jack's penis this morning... it was nice... maybe he would like my butt. What am I thinking? Stop... hmm... Maybe I can ask Dennis to touch me tonight? Yeah, maybe... ok. Stop it, Lana! Stop getting excited... control yourself!'

Mary finally finishes fixing her skirt. As she releases the skirt, she gives Lana's booty a huge slap that resonates loudly throughout the cafeteria.

The newbie teacher is at last covered, her indecent exposure ending, much to the chagrin of the horny audience. Multiple people recorded the whole incident, including the ass slap.

"Ow!" - complains Lana about the slap.

"Sorry, couldn't resist." - apologizes Mary.

"It's o-okay..." - whispers the young teacher sheepishly.

"Also, sorry for my son's pranks." - her new friend apologizes. "Now let's go eat our lunches."

"N-no problem, b-boys will be boys I guess... r-right?" - Lana says, laughing a little and paraphrasing Dennis. "Thanks for the help." - she adds.

They go through the cashier and sit down at the table. During their lunch, lots of students come by and compliment Lana on her big/juicy/bubble/round/fat ass. Lots of different adjectives were used.

Mary authoritatively insists Lana thanks them for the compliments, so, upon her attentive gazes, the naive teacher thanks each student, blushing every time.

Some students even call her a Pawg, she would have to ask someone about that one later.

The two teachers talk about their interests, books and shows they watch. They exchange phone numbers, as Mary promises to send her some tips for good books she could find in the School Library.

Lana has a good feeling about her new friendship, Mary seems nice.

They make their way to the Staff Room to drop their belongings, and then to their respective classrooms to start the afternoon period.

~~~~~~~

Afternoon -- Homeroom

Her students start to arrive a few minutes before the bell. She hugs every single one of them without a second thought. Lana was indeed getting used to the contact.

Lukas was the last one to come in and he smiles at her mischievously. His blue eyes sparkling with a playful glint.

Class was uneventful, with the students spending most of the time working on their term assignments, which would encompass every class and every subject into one long paper. Lana just lets her mind wander about the incidents of the day and helps the students with their questions when required.

A few minutes before class ends, Andrew puts his hand up and calls the teacher.

"Miss Cox, can you explain this to me and to the whole class?" - he inquires, lending her his phone.

She picks it up and looks at it, slightly shocked.

"Well... errm... isn't that the custom here? To give men above sixty, a kiss?" - she asks, embarrassed and confused. She hadn't realized people had taken photos of the moment.

"Indeed, I have a photo of you kissing my grandfather Dick, and also my uncle Bill, the Principal." - he states.

"O-oh, I didn't know you were from the Winston-Phillips family. Thanks for everything?" - she says a bit confused.