Naive Teacher in Winston Ch. 13b

(This is an EDIT to Chapter 13b. The ending scene, where Lana and Dennis are in bed together, was changed substantially.)

"Sausage size bet and naked lesbian art."

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 2023, so any correlations with real life are mere coincidences.

This chapter contains the second part of Day 15, Monday. This will encompass the afternoon and night times.

Thanks for the feedback on the previous chapter. I will try to concentrate more on bigger scenes and sprinkle smaller ones throughout. Will do my best to cut out some boring or unnecessarily 'samey scenes' (if you see any, let me know in the comments or on Reddit).

Enjoy the read,

~ Potato Head

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Potato Note: reminding y'all of some relevant storylines and threads from the last chapters!

* This day, Monday, Day 15, marks the start of the third week of Lana and Dennis' adventures in Winstonstead. So far, they have been enjoying themselves tremendously while their morals have been slowly corrupted by the mischievous townsfolk.

** The fiancees, with the help of their neighbors, are planning their wedding for Day 40, the Friday after the Winston-Fest. You better bet Lana will use every spare second to plan her special day.

** Lana's status and notoriety in Winston are quickly growing; most people already know her by name, face, and body. She is starting to feel part of Winston because of that.

* Monday marked the start of the "Incentive Program" for Lana, where she gets rewarded by bonding with and physically encouraging her students. Also, she had to wear a new uniform that was more revealing than anything she had ever worn before (although not as revealing as some might like).

* Dennis got promoted at work and started a new role as Team Lead. One of his new employees, Uwe, seems to be a disgruntled man out to get his new boss. Unlike the others, Uwe moved to Winston and will join the team locally. To make matters worse, Lana showed up during Dennis' first Zoom meeting with the new team and let her towel fall, exposing her naked backside to the new employees.

** Dennis was dreading meeting Uwe at work, as he gets a bad vibe from the gross man. Also, Dennis has an appointment with Dr. Hardik during lunch to discuss his fertility so he can start a family with our busty protagonist.

* While Lana's morning was very eventful, the afternoon also promises to be interesting, as our heroine will meet her friend Mary for lunch, and they have lots to discuss. She also has to attend the Art Club since she promised her students and colleagues, and after school, she swore to visit Cal and his homeless friends at their camp.

* A couple other notable things: Lana's nipples are still itchy and sensitive, and Dr. Hardik will bring her some medical cream on Thursday, but meanwhile, she needs to be careful with them; during a pee break on Sunday, people took some candid photos of Lana urinating, while Jim was getting rejected by Jen; and Dennis booked a Pink Deluxe massage for Lana, giving her one of her first genuinely lesbian experiences, and emphasizing that "women don't count".

Now, let's recap her morning at school...

* On her way to school, Lana ran into Jack (whom she will see again on Thursday at the Senior Home), Derek Archer (whom she will see again when she visits the Lingerie story), Pringle (who promised to meet the teacher for some naughty time this week) and Justin (who asked Lana to take care of his baby brother, Greg, suggested some dinner at their place, and reminded her of the 'Daily Selfie').

* Principal Bill held a school-wide assembly in the morning, where he discussed the dates for the Winston-Fest and the School Fair. The lecherous principal also revealed to the students that Lana is part of the Incentive Program, coercing her to show her panties (and a bit of her snatch) to all the students and teachers.

** Dates: current week (days 15-19), last regular school week (days 22-25), Winston Week (days 29-31), School Fair (days 32-33), Winston-Fest (days 34-35), school trips (week after).

* The principal's revelation awoke the student's curiosity, and they became more daring and naughty with our teacher, trying to strip her clothes and grope her. The same can be said about Lana's colleagues, that tried to molest her and invite her to have sex at any chance they got. Of course, the fact she sent a picture of her pussy to all the school staff might have contributed to that.

* Greg (or 'Big G') asked Lana to kiss him at the school gate to show everyone she is indeed his "school girlfriend". Zack made fun of the fat kid and pushed the faux couple further. Lana let the boy grope her butt, but Zack wanted more, getting him in trouble with Mary Hunter, his homeroom teacher. Worth mentioning that Lana still owes Greg a reward for him helping the AV Club during the weekend and that Dennis basically gave his full blessing on the situation, even mistakenly agreeing to let her behave as she did at the start of their relationship.

** As promised, Evie told her teacher about losing her cherry with Wyatt. The petite pixel made Lana question if her fiancee would be as patient with her as Wyatt and if Dennis could fill her entirely due to his size. Maybe Lana can use a dildo to get a feel for it. Evie volunteered to wear a strap-on on her teacher.

** Things are a little awkward between Jim and his teacher after the blowjob in the tent. Maybe some unresolved feelings. But they had a quick chat, and Lana decided to discuss matters personally with Jen at the Art Club.

* Afterward, Lana met Bill in her classroom. They discussed the accidental email, the Blue Beach Bar photos (which he "dealt with"), and the Biology supplement on Tuesday morning (in which Bill recruited Roger and Pietro to participate).

** As requested by Mary, Bill also brought a purple butt plug, so Lana can start training her asshole for her fiancee. Bill suggested she use it daily to get used to the feeling and move on to 'larger things'. She needs to come up with a name for it.

* BJ showed up to detention along with Wyatt, who was there to 'protect the teacher and redeem himself'. Bill explained to Lana that the Program was about motivation and encouragement, not punishment, so our teacher was coerced into giving Benjamin a tittyfuck, something the little bastard always wanted. Lana got very excited during it and started teasing the principal to get some attention from him. She got rewarded with a rimjob from the burly man and her new butt plug up her ass. The ass-play gave her a small orgasm while BJ spilled his seed all over her.

** In the end, Bill was proud of her, although he chastised her for wearing a bra more than once, which Lana didn't enjoy.

** Our protagonist went to the bathroom to finish freshening up, but Evie was there blowing Wyatt. Lana left quickly to meet her best friend, Mary, for lunch.

This is where our story resumes...

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Lana leaves the bathroom and saunters upstairs to the Staff Room. The bell rings, indicating the start of the lunch period.

'I'm excited to catch up with Mary! It's been since Saturday night...' - she thinks giddily. 'Lots to talk about... like the email, the butt plug Bill gave me... the lingerie... oh, she doesn't know about Sunday either!' - she thinks, biting her lip and recalling all the naughty situations she got herself into.

Although Lana had just lightly orgasmed a few minutes ago, she is still aroused, as is evident by her sensitive (and burning) nipples and by her throbbing pussy.

'Mmm... I really need some friendly advice about practicing for Dens... Many people have told me things, but I don't trust them like Mary. I know I can rely on her advice.'

As she walks, she notices some students looking at her funny.

'Probably what Bill announced earlier...' - she thinks, a little embarrassed.

Some teens snicker and whisper things as she passes, making her blush.

'I guess this is what I have to go through now... they'll probably get over it, right?' - she reflects as she goes into the Staff Room.

Lana hears a loud, excited clap when she enters.

"Perfect timing, Missy!" - Prof. Henry says jollily. "We just put this beauty up!"

The scrawny old lecher points at an 11' x 17' poster on the corkboard.

The brunette teacher gasps out loud. She is staring at a blown-up photo of herself in the full Princess Leia cosplay, lifting her dress and exposing her hairy twat to the world.

"Prof. Henry! This is not appropriate!" - she shouts, her heart thumping loud in her ears.

"Oh, pish-posh! I love the bush. I think your beaver looks majestic. So wild." - the short, bony professor says.

"Uhh..." - she stutters, embarrassed by the compliments. "But what if a student sees it?"

"Oh, bird, it's not like they haven't seen it." - the sexagenarian man chuckles.

"Not everyone!" - the busty teacher points out.

"Then it's a good opportunity for them to admire your banging beauty." - the scrawny professor smiles.

"Ah... I..." - Lana stammers, lost for words. 'Goodness... this is mortifying... having my naked selfie on display in the teacher's room... this is crossing a line... right?' - she ponders.

"It's just a shame your knockers aren't showing. Can you send us a new photograph?" - Henry asks.

Before Lana has time to reply, Mary Hunter appears from the bathroom. The sexy teacher is wearing a tight white blouse tucked into a black leather pencil skirt, dark stockings, and black heels. She is a blonde beauty in her mid-30s, with fake C-cup breasts, slightly tanned skin, and full pouty lips.

"Bestie!" - the blonde says excitedly, a personality trait only seen by a few close friends.

"Ahhh!" - Lana squeals, and the two bombshells hug, their boobs mashing together.

Prof. Henry's jaw falls open, both by Mary's schoolgirl display and their sexy embrace.

Mary breaks the hug and looks peculiarly at her best friend.

"You have something on your face..." - Mary points at Lana's left cheek.

"Huh? AH!" - Lana exclaims, mortified. Her colleague leans forward and sniffs it.

"Is that cum? Lana, you horndog!" - the blonde exclaims with a wicked grin.

"Noooo..." - the brunette moans, rushing into the bathroom. She looks at herself in the mirror and sees a few splotches of sperm she missed earlier. 'That's why the students were staring! Oh no!' - she thinks, chagrined. 'Maybe they didn't know... I bet they thought it was my lunch... yeah... I hope so... ugh... what would they think if they knew their teacher was walking around with her student's fresh semen on her face... gosh... so improper...' - she squirms.

The buxom fiancee properly cleans herself this time and returns to her colleagues. Mary is already sitting at the table with their lunch set out. Prof. Henry is at his desk, quiet as the mouse he is.

"Welcome back." - Mary grins. "Who was the baby juice donor?"

"Ew, you are so crass, Mary." - she says. "Benjamin..." - the brunette replies softly.

"BJ Tan? Lucky's friend?" - Mary blurts, using her son's pet name. Lana nods. "My, my. You'll have to tell me all about it."

"Ehmm..." - Lana says, glancing at Henry's direction.

They start eating, and Mary tells her friend about the mini-trip she and Lucius took to their vacation home.

"Finally got Muffin back! I missed him so much." - the busty blonde says.

"Muffin? I did not know you had a dog." - the pretty fiancee says.

"Right! He's been in a doggy retreat for the last month. He needed a break after some stressful times." - Mary explains.

"Oh, that sounds nice." - the brunette comments, munching on her meal.

"Yes, my little baby is all recovered now." - the blonde milf says.

"I cannot wait to meet Muffin." - Lana smiles.

"You will. This weekend at Dennis' surprise party." - Mary says and her friend nods.

Lana then recounts to Mary all about Sunday and everything that happened. Her friend listens attentively, just nodding or making short acknowledgment sounds.

"You had a pretty big day!" - the blonde bombshell declares.

"Gosh, it was crazy..." - the curvy fiancee agrees.

"I loved the restaurant bit. That was well done, bestie." - Mary praises her.

"You think so?" - Lana asks doubtfully.

"I know so. That and the lingerie! You probably made Dennis super happy." - the Hunter woman says.

"I really hope so." - the brunette says, looking down at her food.

"Are you still troubled?" - the older teacher asks.

"Uh-huh, I need to keep him satisfied." - the youngest woman explains.

"Seems like you are on the right track then." - Mary states, squeezing her friend's hand in support. Lana smiles at her. "So, Dennis loved the lingerie. When are you getting another one?"

"Sometime this week. Want to come with me, bff?" - the voluptuous brunette asks.

"Sure, that will be fun." - the milf agrees. She eats a couple bites of her salad. "And anal?" - she asks out of the blue.

Lana almost spits her water.

"Excuse me?!" - the wife-to-be shouts, surprised.

"Bill gave you the purple butt plug, right?" - Mary says.

"He did..." - Lana admits sheepishly.

"Where is it?" - the luscious blonde asks.

Lana glances at Prof. Henry, who whips his head away and pretends to not have been listening. She sighs and brings out the anal toy.

"Here... Bill wants me to name it." - she says dubiously.

"Good, good. Did he show you how to use it?" - Mary asks.

"Well..." - Lana tells her best friend about the detention, trying to keep her voice low. Mary doesn't interrupt or embarrass her, patiently listening to the story.

"Wow, that sounded fun. I wish I was there." - the sexy blonde says.

"Hmm... me too..." - Lana earnestly says, blushing. "Why did Bill have this?"

"Well, he has a huge collection at his house. Maybe he can show you someday." - Mary explains.

"Gee..." - the brunette mutters and blushes, imagining the burly principal showing her a room full of various dildos and toys. Of course, he is naked while doing so, his enormous dong swinging around heavily.

"So, now you need to keep using it. After a couple more days, you should be ready to try a real one." - Mary says nonchalantly.

"A penis?!?" - Lana blurts outs. She sees Henry staring at them, wide-eyed. Mary giggles.

"You're so precious. Of course, what else?" - her blonde friend says.

"But... I am n-not sure I a-am ready..." - Lana stammers, clearly flustered.

"You want some practice. That's the best way." - the Hunter woman says. She notices Lana's expression. "Don't stress about it. Give it a few more days. Use your new friend and let people play with your bum. You'll be willing in no time." - she assures.

Lana gulps. Her friend's words resonate with her.

"You think Dens will like it?" - the naive teacher asks.

"Oh, for sure. I have never met a man that's not into anal play. Just get comfortable with it first." - the blonde says.

"Why do you say that?" - Lana asks curiously.

"Last thing you want is to introduce the idea when hesitant or not into it. That will end any future possibilities." - Mary says emphatically.

"Ah... I would not want that." - the busty brunette accepts.

"Then practice and surprise him." - the sexy milf winks seductively.

"Hmm... maybe a birthday gift?" - Lana says tentatively.

"That works. But that's soon, bestie. Are you ready to be buttfucked?" - the blonde questions.

"Gee..." - the innocent teacher says under her breath. Her nipples ache at the idea.

"You'll need to get a few hard cocks in your ass before Saturday." - Mary says, not measuring words.

"Uhh... I am not sure..." - the trusting fiancee mumbles hesitantly, but her cooch twitches and gushes at her friend's words.

"Just take it one step at a time." - the experienced woman says, squeezing her friend's hand. Lana exhales, happy for the support. "So... did you like having the plug inside you?"

"I did..." - the future-wife admits.

"A real one can be even better. So you can look forward to that." - Mary smiles.

Lana nods her head, both apprehensive and excited about it.

The two hotties eat a bit more, Lana chewing over her friend's advice. The naive teacher has no idea how heavily Mary's words will weigh on her future decisions.

~~~

"And have you been practicing for the play? I guess Jim and BJ were good efforts." - Mary asks after a while, referencing her recent adventures.

"A little..." - Lana says shyly.

"Use the dildo I gave you. You can use it in different holes." - the blonde says suggestively.

"I will try." - the fiancee promises. 'I need to ask Mary about it... my performance with the boys wasn't that good...at least not good enough for Dens.' - she thinks as she bites into her food. "Bestie, how did you get good at oral sex?"

"Don't worry, I'm mostly talking about acting. You're probably decent enough at blowies, babe. At least for Dennis." - the blonde tries to reassure her friend.

"I am not certain... Jim and BJ were not all that impressed. And they had zero prior experience. Dens was completely soft the last time I tried on him." - Lana says, visibly disturbed.

Mary notices something in Lana's voice. A hint of her competitiveness, a desire to be better than others. The Hunter woman realizes she can use that for her friend's sake.

"I heard Cynthia is very skilled at blowjobs." - Mary comments, eating her salad.

"What? She is?" - Lana asks, wide-eyed. She didn't expect that.

"Remember? She made Dennis come in her mouth." - the blonde says.

"Ugh... do not remind me about that." - the busty brunette says painfully. "How can I become better than that bitch?" - she asks, determined.

"You want to be the best cocksucker around?" - Mary asks. Lana gasps but nods timidly.

Mary Hunter smiles, a plan coming to her. Even if Lana gets good at blowjobs, if everyone keeps saying she needs to improve, her competitiveness will push her to keep perfecting her technique. Mary makes a mental note to spread the word around.

"That sounds so dirty..." - the gullible brunette mutters, her cooch clenching.

"It's what we're called." Mary winks at her. Lana feels a shock on her snatch.

'Am I a c-cocksucker too? I guess so... I wanna become the best one for Dens... he will love it. I will show him that I am way better than that tramp.' - Lana thinks.

"My best advice is to practice your cocksucking skills. Perform as many blowjobs as you can." - the blonde continues.

"Really?" - the brunette asks. 'That makes sense, I guess...'

"Yes, all dick shapes and sizes. But if you are unsure, try smaller ones first. They will be good practice for Dennis." - Mary says, and Lana nods agreeably.

Once again, her vulgar and wise words ingrain deep into Lana.

"But what if Dens is not into it?" - the buxom fiancee questions.

"Well, you just need to find what tickles his fancy. Like the feet thing." - Mary giggles.

"Mmm... true. What does he like..." - Lana ponders.

"He's always excited about you fooling around with others..." - the blonde points out.

"Oh... are you positive?" - the naive teacher asks doubtfully. Mary sighs.

"He liked the Horn Test on Saturday night, the Photoshoot on Sunday, and the restaurant play. What more proof do you need?" - the milf says, throwing her hands up.

"As long as I do not go too far." - Lana adds with a giggle.

"Mm-hmm! Stay within limits, and he loves it." - Mary concurs.