Naive Teacher in Winston Ch. 12a

"Homeless helper and vibrating massage."

(This is a small edit to the Meet and Greet to remove some fluff parts)

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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 coincidences.

This chapter contains the morning/lunch of Day 14 (Sunday). The afternoon will continue on Ch. 12b. Thanks for the support!

Enjoy the read,

~ Potato Head

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Potato Note: continuing with this section! This chapter is part of Sunday, so I am reminding y'all of some of the relevant storylines below.

* Fourteen fateful and sex-charged days have passed since our heroes, Lana and Dennis, arrived in Winstonstead. In the last two weeks, their prudish views have been slowly shattered. The townsfolk's efforts are paying off, and the couple's corrupted minds are starting to show.

* Lana has been teaching at the local school, and the shenanigans she got involved with students and staff culminated in her being enrolled in the "Incentive Program" by Principal Bill.

** To celebrate Lana's success, Dennis booked her a "life-changing" massage and a romantic dinner at a fancy restaurant, all scheduled for Sunday.

* At school, Lana is the supervisor of the AV Club. She helped the members, Jim, Herb, and Simon, create a tantalizing recruiting poster and a making-of video of her in a diminutive cosplay.

** They agreed to meet on Sunday at the Town Square and set up a booth to promote the video, which may include some more raunchy cosplay.

** Lots of people mentioned meeting up with our teacher, including Dr. Hardik, the lecherous local doctor; Dick, the mayor; her neighbor Jack; some of her students; and many more.

** Also at school, Lana agreed to become Greg's "school girlfriend", all to save him from his bullies classmates, led by Zack Archer.

* On the previous day, the teacher spent her time at the beach with her students on an official school trip and attended Dennis' work party at night.

** At the beach, there were naughty rewards in class, massages, lesbian exploration, and lots of interactions with the locals. She met Jade, a local bimbo reporter, and gave her a live interview for TV where she had her pussy exposed. She also met Cal, the leader of the homeless man of Winston. She promised the man that she would stop by the park on Sunday where he and his buddies live to give him money and a kiss in exchange for her beach cover back.

** Afterwards, she and Dennis went to the party with his teammates, hosted by her best friend, Mary Hunter. The party got out of hand. They played naughty card games and took photos of Lana's pussy. She even let Dennis' coworker hump her ass and come all over her dress. She decided to ask in a future opportunity if Dennis minds if she practices anal play. And that is not even mentioning the "Horn Test", where her friends led the gullible teacher. She ended up masturbating and licking the dick of another one of Dennis' colleagues. Even Dennis had his fun, getting a promotion and ejaculating all over his female work friend, not necessarily in that order.

* Dennis couldn't get it up during the couple's nighttime play, even when Lana tried her best, licking and teasing her fiancee. She was apprehensive about it and decided she needed more experience. ASAP.

~~~~~~~

Lana Cox wakes up feeling something hard between her legs. Confusedly, the beautiful young teacher looks underneath the blanket and realizes she fell asleep mid-masturbation.

She is naked from the waist down with a blue dildo lodged halfway between her plump thighs.

In a panic, she glances at her ginger-haired fiancee, asleep beside her. She sighs deeply.

'Phew... Dens didn't notice it. That would have been so embarrassing.' - she thinks.

Discreetly, she picks up the sex object and wipes it down. Satisfied, she places it back in its hiding spot at the back of the second drawer of her bedside table.

Lana puts her shorts on and gets up to shower. She looks at her sleeping future-husband and smiles.

Dennis Laywood is tall, around 6'2, with nice ginger hair, fair skin, a boyishly handsome face, and lovely caramel eyes. In another universe, he could have been an athlete. Still, his current lanky and out-of-shape build would discourage anyone from thinking that.

'He's been so supportive lately. And adventurous. I am glad we moved here.' - she thinks lovingly, a wide smile on her flawless face. 'I can't wait to get married.' - she squeals excitedly.

The brunette walks to the bathroom, momentarily stopping in front of the closet mirror to admire her curvaceous 5'3 tall body. She does a little spin, and her voluptuous 38DD breasts jiggle underneath her pajama top. She giggles at the arousing sight.

She wipes the sleep off her large green eyes and undresses in the bathroom. She turns to admire her shapely butt, toned and thick, a boner-inducing vision to most men (and some women).

Lana hops in the shower and starts to clean herself. She stops when she gets to her cooch.

'Hmm... she's getting a little bit hairy. Should I shave her?' - she reflects, running her hand through her brown pubic hair. 'Ah, she can probably wait. It's not like anyone is going to see her today. Besides, even if they did, she seems fine.' - she decides, admiring her tight, hungry, and pink pussy.

After the shower, she wears a pink cotton bra and matching panties, ordinarily dull. She decides on a pair of blue leggings and a pink floral top for her outfit, ideal for a casual Sunday setting. Admiring her pink toenails, she again decides on a pair of open-toed flats but tan-colored this time.

Suddenly, she receives a message on her phone.

* Blip, blip! Blip, blip! *

Message -- 7:30 am -- Jim Rouge

* Jim - Hi, Miss Lana. Meet us at 10:30 at the town square. We will be setting up our booth!

* Lana - Of course! Cannot wait!

* Jim - See you there!

The buxom teacher smiles, happy to be able to help her students with their projects.

Back in the bedroom, she doesn't find Dennis. Instead, she hears some noises coming from the kitchen.

'He must be preparing breakfast. Yay!' - she squeals, skipping happily to the living room.

~~~

"Morning, babe!" - Dennis says as his lovely betrothed walks in.

"Morning, hun!" - she replies with a big smile. She makes her way to him, and they exchange a quick peck on the lips.

"You smell amazing. I love your shampoo!" - he says adoringly.

"I know you do. It is vanilla coconut!" - she beams. She sniffs the air; something is baking in the oven. "And what are you cooking?"

"There is some bacon in the oven. I'm thinking pancakes. Maybe some fruit, too." - he explains.

"Sounds yummy." - she fawns over him.

"It will be, but I barely started." - he admits. He grimaces, thinking of all the effort ahead.

"Let me help, you silly carrot." - she says and pinches his cute butt playfully.

As they cook, they chat about the previous night.

"Sorry again about that. Not sure what happened." - the ginger fiancee says awkwardly, referencing the fact he couldn't get up during their adult time.

"It is okay, Dens. I will fix it." - she says obstinately.

"What do you mean?" - he asks, unsure of what she has in mind.

"You will see!" - she says boastfully. 'I will get lots of practice, and then I'll surprise him. He'll be blown away!' - she thinks, proud of her plan.

"If you say so." - he shrugs, deciding not to pry any further. Sometimes Lana could be quite a confusing nut to crack, but he got used to it after being together for so long.

'I will ask Mary if she has other ideas too. She must have some experience with this.' - she decides in her head.

Dennis concentrates on the food while his future-wife hums a happy tune.

"Last night got a little crazy, right?" - he chuckles, breaking the silence.

"True. Your coworkers are a wild bunch." - she says, chopping some melons and strawberries.

"Don't even get me started... I'm still getting used to it. So much drinking too. Ugh." - he says, pressing his temples, feeling the tiniest of headaches.

"Too much. But I am happy that I became part of the team." - she says. 'It was a great idea to fool around with the guys. In the end, they all admitted me into the team. Even Lucius. I have to thank Mary for coming up with the games. They helped.'

"Me too, babe. We need to have friends around here." - he says, stirring the pancake mix.

"We have so many now! But some of them might be too much." - she giggles. 'They always try to grope, tease, or see me naked. I'm glad Dens doesn't mind... he's so confident and trustful now. There's no arguing that.' - she thinks, recalling other men who would have gotten more upset at their friend's advances.

"Yep... but so is your friend, Mary!" - he adds, and they both laugh.

"I know. Mary is so forward. And beautiful too." - Lana says, thinking back to her friend touching herself while Paul humped her ass. 'Ah! I should ask him about that...'

"Mary must be a handful for Lucius. But she also seems like a good partner." - he says, and she nods.

"Not as good as us!" - she sends him a kiss while arranging the fruits in bowls with some fat-free Greek yogurt. "Speaking of handful...."

"Hm? What is it?" - he asks, taking the bait. He starts to cook the pancakes now.

"Guys seem obsessed with my backdoor. Even Paul." - she says nonchalantly.

"Your backdoor?" - he chuckles uncomfortably. Dennis feels a stir in his pants at the thought of her juicy butt.

"Um-hum! I did not know you men were so interested in anuses." - she says, trying to measure his response. 'Let's see what Dens thinks...'

"Well... I guess it's a thing for some." - he replies, trying to sound uninterested.

Dennis would love to play with any part of her, but he is too chicken to say that out loud. He knows he will get it all once they are married, as Lana will do anything for him. He just needs to have patience.

"You are not like that. Right, hun?" - she asks curiously.

"Of c-course n-not, babe." - he stammers, trying to distract himself by concentrating on the food making.

'Hmm, that's what he keeps saying. Maybe the others are into it because their partners were experienced?' - she ponders.

"We were always taught the anus was gross." - the busty brunette says.

"Yeah, it's not something that came up in our old community." - he agrees. "Exit only, as they say." - he chuckles awkwardly.

"Oh, so you do not think it is sex when you use it?" - Lana asks curiously.

"Well, we were told it's not made for that. So I'm not sure. Maybe not." - he says, focusing on perfecting his pancakes to fully capture what she means.

"Agree, I do not think so either. And do you think it would hurt?" - she pries.

"Probably? Who cares?" - he says dismissively, his mind elsewhere.

'Dens is right. That is what lube is for. Can't forget that.' - she reflects.

"Babe, why all these questions?" - he asks, unsure how the chat got to this spot.

"Like I said, guys seem obsessed with it." - she repeats.

"Ah, right. I guess the guys at work might be." - he nods, trying to seem indifferent again.

'So he's not interested in my anus... maybe he will be if I get really good? Will it be bad if I practice with another person? No... he just said it's not sex, so it's probably fine. He will be happy when I surprise him. He always is.' - she evaluates.

Lana starts arranging the table while Dennis finishes the pancakes. A minute passes.

'I'll ask if Dens minds if I get some practice using my anus. I'm doing it for us, after all.' - she decides, mustering the courage.

When she calls his attention, the ginger fiancee is taking the bacon out of the oven.

"Hun, do you mind if I do something you are not interested in?" - she asks with a cute pout.

"Hmm... not at all, babe." - he shrugs.

"Maybe if I practice a lot and get good at it, you would be interested in trying it with me?" - she asks.

"Sure, that's possible..." - he says, thinking it is related to a hobby. "At least I want to hear all about it." - he says supportively.

"Really?" - she blurts out. 'Oh, gosh. So he wants to know? Well, that seems fair. Hope it doesn't ruin the surprise. But it makes sense if he wants to understand more.' - she rationalizes.

"Uh-huh, I love when you get passionate about things." - he says, smiling fondly at her.

'Oh... will I get passionate about letting other men play with my anus? I didn't know. I guess it will feel good like Pringle said. And if Paul's fixation is any indication, then Dens might be correct.' - she contemplates.

The couple finishes preparations and sits down to eat.

"Dens, would you rather I am good at something before introducing you to it?" - Lana asks after a few bites.

"What a weird question, babe... hmm..." - he says as he shoves food into his mouth. Dennis thinks while chewing. He swallows. "I guess it makes more sense if you at least understand it. Or have some knowledge, you know?" - he concludes.

"Why do you say that?" - she asks, surprised by his answer.

"Like a card game..." - he says before stuffing his face again. Lana anxiously waits until he finishes chewing. "It's easier to explain the rules and for others to learn if one of the people has played before." - he elaborates.

'Aha! So Dens thinks so too! His explanation is perfect.' - she thinks to herself.

"Wow, hun! That does make sense. You are brilliant." - she praises her future-husband, giving him googly eyes.

"It's just logic!" - he winks at her.

'Then it's decided. Dens will be more receptive to my anus once I learn about it and have some practical experience.' - she considers, chewing her breakfast. 'I wonder if I need to do the same with intercourse? Lucius said so. Hmm, better to take one step at a time. I already have to practice with my mouth too. I'll worry about my cooch later.' - she decides.

They eat for a few more minutes, enjoying each other's company and the lovely food in front of them.

"So, babe, what's the plan today?" - Dennis asks, munching on a beacon piece.

"I need to meet the AV Club later this morning. What time you booked my massage again?" - she asks. He glances at the time on the microwave. It says 8:35 am.

"In less than an hour." - he answers, sipping his OJ.

"Oh, I better go soon then." - she says, standing and starting to clean up.

"Yeah. I hope you'll like the masseuse." - he says, helping his fiancee with the dishes.

"I will! You said she is highly recommended. Thanks, hun." - she stands on her tippy-toes to kiss him on the cheek.

"And... uhh... can I join you at the booth today? You know... to help." - he asks, his pervert side speaking louder.

Dennis is secretly interested in possibly seeing his fiancee in cosplay and securing a copy of the steamy making-of for himself. Also, he wants to show off Lana to the other men in town, so he can brag about his sexy betrothed.

"Of course! I do not see a problem with that. The boys will love to have you." - she answers with a big smile.

"That's great. Can't wait to get to know them better." - Dennis says as he puts the plates in the dishwasher.

"Oh, yeah! I forgot you are all huge nerds." - she giggles. He chuckles and shows her his tongue.

"For your information, this nerd pulled out a hottie!" - he replies. He gulps and gingerly squeezes her boob playfully. She moans with both surprise and pleasure.

"Pfff... someone is too full of himself." - she giggles, and they exchange a quick peck. "I will message you when I get out of the massage."

"Perfect, I'll meet you there afterward." - he says.

They finish cleaning up, and Dennis excuses himself to shower and deal with some work. Lana sits on the couch and messages her best friend.

+++

Message -- 8:56 am -- Mary Hunter

* Lana - Hi, bff! Are you around?

* Mary - Morning, bestie. What's up?

* Lana - Dens had trouble getting up last night *shame face*

* Mary - Getting up?

* Lana - You know what I mean.

* Mary - I don't. Tell me...

* Lana - He could not get an erection! I tried everything. Even licking his peepee.

* Mary - *laughing emoji* You're so precious.

* Lana -- I am serious. What do I do?

* Mary - Well, I told you. You need practice.

* Lana - I know that, but I cannot do it now. It will take time.

* Mary - So?

* Lana - I want a quicker solution. Maybe there is something else I can try?

* Mary - Without experience? Hmm... I don't know...

* Lana - Pleeeeease?

* Mary - Ah! There's a good lingerie store in town. You should get one to try and see if it works!

* Lana - Lingerie? Really?

* Mary - You never wore any?

* Lana - No? Do I need to?

* Mary - It helps. Makes you feel sexy, and men love it.

* Lana - Wow! OK, maybe I will try it.

* Mary - You do that! Don't forget to send me a pic of it.

* Lana - I will. Ah, can we have lunch tomorrow?

* Mary - Of course, always. Want to talk about anything?

* Lana - I tried experimenting with the blue dildo. Too big. I need some tips.

* Mary - Lol, you are too precious. I'll help you tomorrow!

* Lana - *embarrassed emoji* Thank you. Are you coming to the town square today?

* Mary - I can't. Lucius and I are driving to our vacation house to check on it.

* Lana - Ah. Good luck!

* Mary - Thanks, talk tomorrow. Bye bestie *kiss* *heart*

* Lana - See you tomorrow, bff *kiss* *heart*

+++

"Mary is the best. She always has a solution for things." - Lana says to herself. She glances at the clock and sees it's five past nine. "Oh, I better go. Don't want to be late." - she walks to the bedroom door. "Dens, I am going!" - she shouts.

"Bye, babe. Love you!" - he shouts from the bathroom.

"Love you too, see you later." - she replies.

Lana fixes her flowery top, adjusts her blue leggings, grabs her bag, and leaves her house, ready to face the day.

~~~~~~~

As the voluptuous teacher makes her way to the sidewalk, she hears her neighbor calling her.

"Hi, Lana!" - Lilly waves with one hand. She is holding Evan, her 5-year-old son, with the other hand.

"Hello, Lilly! Nice to see you." - Lana says as the two neighbors walk toward her.

Lilly is Jack's wife, and she's in her late 30s. She is a pretty woman with raven hair and small breasts. Childbirth took a toll on her, making her slightly overweight and giving her a permanently tired look. She is fun, easy-going, and extroverted. Although a little too perverted and exhibitionistic for Lana's taste.

"Saw your poster today, neighbor. Sexy as heck." - the neighborly woman winks.

"Heck, heck, heck!" - Evan repeats happily. Both women giggle.

"My poster?" - the busty teacher asks, intrigued.

"The one where you're dressed boldly. Loved it." - Lilly explains.

"Ahm... w-where did you see it?" - Lana asks, concerned.

"It's all over the town center. I saw it on my way to get groceries this morning." - Lilly says.

"Oh, gosh!" - the brunette exclaims, flushing. 'This is so embarrassing... I didn't know everyone in town would see it... maybe it's not so visible? Hope so.' - she thinks.

"Don't sweat it. It's beautiful. And hot. Congrats for being so daring." - Lilly says.

"Erm... thanks..." - Lana replies, her face beet red.