Naive Teacher in Winston Ch. 05

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. We are starting to get hot hot hot.

Note: This chapter was going to contain Sunday too, but it was getting too big, so I decided to release just Saturday and then make another Sunday chapter (maybe with Monday too).

Here is what you can expect from this chapter:

* Day 6 -- Saturday -- Lunch with Jack and Lilly -- Dinner with Dennis' team

Enjoy the read,

~ Potato Head

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

Day 6 -- Saturday

Morning

Lana wakes up reinvigorated with the session from the previous night. She lays in bed reflecting on how well she slept, better than she had in months.

'Maybe I can orgasm more often.' - she thought. 'After all, it is for my health.'

Next to her, Dennis is still in deep slumber. The teacher doesn't even remember him coming to bed at all, must have been late. She decides to let him sleep, grabbing a robe and tiptoeing out of the bedroom.

The lovely fiancee has a lazy morning, watching some news and organizing the house.

Dennis doesn't wake up until later in the morning, he apparently stayed up almost all-night working.

'Poor dens...' - she reflects, while serving him coffee. He looks exhausted.

"Babe, what time do we have to go?" - he asks sipping his coffee.

"Very soon, at noon sharp... Dibs on the shower!" - she says giggling and running out of the kitchen.

"Hey, not fair!" - he mumbles trying to sound playful.

Lana showers and starts to get ready. While Dennis is showering, she spends some time deciding on her outfit, opting for a knee-length light green sundress, that buttons up from her navel to her upper torso, not leaving any visible cleavage. However, even if the dress was conservative, her voluptuous figure was rather obvious, hugging her hips nicely and accentuating her amble bosom.

When the couple is ready, they make their way to the neighbors for lunch.

~~~

Interlude -- About Lana

You reader might have noticed that Lana doesn't like to back down of something after she agreed to it or said it. This is due to her strong and conservative morals, believing firmly that lying is wrong and that your word is your bond. She is unaware that this constantly gets her into trouble, with everyone exploiting this characteristic of our heroine.

Another quick detail about Lana that hasn't really come up yet is that sometimes she has a mean competitive streak. She vehemently dislikes losing in certain circumstances.

This is mostly due to jealously (and insecurity), often happening in situations related to her relationship with Dennis. One example is Lana trying to one up any woman that comes close to him.

This behavior also comes out in certain situations, like Lana taking care of her body and regularly exercising. She secretly wants to prove to others that she can maintain her figure in top shape.

So far though, our heroine didn't have to compete or bet on anything, but this was about to change.

~~~~~~~

Lunch

Dennis rings the bell and Jack quickly opens the door.

"Hello neighbors!" - he says shaking Dennis hand. He then hugs Lana quickly.

"Thanks for the invite, Jack." - says Dennis seriously.

"Our pleasure. Come in, come in! Follow me." - he says, leading the couple directly to the end of the corridor. Lana glances at the other rooms but doesn't pay too much attention.

Their kitchen/dining area was relatively big, with a lot of open spaces. A big marble island separated the kitchen per se from the dining table, which was already set and ready for lunch. An open door led to the living room and the rest of the house.

Lilly was busy finishing some last-minute dishes on the kitchen, and Evan, their 5 year-old kid was already sitting at the high chair on the end of the table.

"Lilly, meet our neighbors Dennis and Lana Laywood!" - Jack announces.

"Actually, we are not married yes, Lana is a Cox." - corrects Dennis.

"Right, she likes Cox indeed." - says Jack quietly snickering. Dennis seems confused by the sentence.

"Ah! So lovely to finally meet you both!" - says Lilly loudly, dropping her things and coming to meet the couple.

She hugs Lana first and then Dennis, giving him a big kiss on the cheek.

Apparently, Lilly is not very photogenic, as in person she looks way better. She is pretty, on her late 30s, her body is slightly overweight, but still in decent shape. The housewife is wearing loose leggings pants and a tight top showing some cleavage, the shape of her small breasts noticeable underneath.

Lilly is clearly out of Jack's league, who is bald, out of shape and in his mid-forties. He is wearing a t-shirt and sweatpants, again.

"Nice to meet you too, Jack told me only good things." - Lana says smiling.

"I really hope so! And this cutie is Evan, our little precious." - she says, pointing at her kid.

Lana waves at him, he puts his head down shyly. Dennis approaches him and extends his fist towards the boy. The boy fist bumps him and laughs. Dennis has always been great with kids, one of his many qualities. Lana's heart skipped a beat thinking of her future children with her almost husband.

"Evan seems to like Dennis." - says Love. "He is lovely!"

"He is, he will grow up to be strong and good, just like his father." - says Lilly touching Jack on the arm. She still loved her husband very much.

"Love you Lillykins!" - says Jack, kissing her on the lips and playfully slapping her ass.

Dennis and Lana exchange shocked looks at the display of affection.

"Oh you! Let me finish lunch." - Lilly says. "Please sit." - she instructs, moving back to the kitchen.

The couple sits down on the table, still with a surprised look on their faces.

"Oh, my bad Denny-boy. Forgot you both aren't from here and are prudes, apologies. PDA is common here, as Lana might know." - he informs, winking at her.

"We are not prudes. It is just different where we are from." - replies Dennis.

"What is a PDA?" - asks Lana confused.

Evan starts to shout 'PDA, PDA, PDA, PDA' out loud. Jack stops him.

"Oh, it stands for Public Display of Affection. You know, kissing, hugging and touching in public is all very normal and encouraged here, as you're already aware." - the couple nods shyly.

"Yeah... we noticed." - mentions Dennis.

"People seem to like PDA-ing me specifically." - comments Lana a little frustrated.

"Of course! Who wouldn't want to touch your slutty body?!?" - exclaims Jack. Lana turns red.

Dennis starts to open his mouth to say something, but Lilly comes to the table, interrupting.

"Lunch is serveeed!" - she announces happily. "I prepared my specialty, Stuffed Chicken and Lemon Cilantro Rice. Enjoy!" - she says, pointing out the dishes.

Evan starts to shout 'Stuffed, Stuffed, Stuffed, Stuffed' out loud.

The food looks delicious, with sides of salad, potatoes and warm bread. There is even some chicken nuggets for Evan. Everyone starts to eat, the previous discussion completely forgotten.

Evan rapidly eats his nuggets and Lilly takes him to the living room so he can play with his toys. She quickly comes back to the table.

The two couples talk about their lives and get to know each other over the scrumptious meal.

"Ahh! I am stuffed! Thanks, Lillykins, it was amazing as always." - states Jack lovingly.

"So good, Lana, you have to learn a thing or two from Lilly." - jokes Dennis.

"I can probably do it better..." - the teacher mumbles quietly.

Jack leans back on his chair and belches loudly.

"Jack! Manners!" - his wife says, slapping him playfully on the arm.

"Can't help it when the food and the cook are so delicious!" - he winks to his neighbors and quickly squeezes her breast in front of everyone.

Lana and Dennis both open their mouths, shocked. They exchange incredulous looks.

"Ermm... Jack, I would appreciate if you didn't do this in front of Lana, she is not used to it." - says Dennis towards his neighbor.

"Hey, I can take care of myself, I am a grown woman." - Lana says slightly upset. "You can do whatever you want at your home Jack." - she says, looking daggers at her fiancee.

Dennis mouths a 'sorry' with his mouth, she smiles back.

"If you say so..." - says Jack turning and starting to make out with his wife. The kissing intensifies, until he is groping one of her breasts. Their tongues are fully exploring each other's mouths.

The naive couple sits there, appalled at the situation. They are blushing furiously, both incapable of pulling their eyes away from the sloppy makeout session.

Jack then breaks the kiss up. The couple regains their senses, a spell broken.

"Thanks for that Lana, not everyone is cool with it." - he says looking the fiancee and getting up from the table.

Lana gasps loudly and points at jack. He has a massive erection, creating a noticeable protruding tent in his sweatpants. His jutting boner seems bigger than anything Lana or even Dennis ever saw, being a solid 7.5'' (inches) long, although very thick.

"Wow!" - says Lana impressed, not containing her thoughts. Jack smirks.

"Ermm... Jack, can you not do this? Lana is not comfortable with this." - asks Dennis.

"I am an adult Dens." - says Lana upset at her husband patronizing her. "Jack can do whatever he wants at his house with his big boner..." - she says quietly.

"That is right hahaha!" - bellows Jack, starting to walk.

"You don't mind this lewd behavior, Lilly?" - says Dennis fully turning to Lilly and ignoring Jack.

"Of course not, why would I be upset at my husband having desire for me? It is flattering." - she explains.

"But it is not proper behavior." - Dennis argues. "Right Lana..." - he turns back, and his voice trails off.

Jack is towering over Lana, his sweatpants-clad erection poking at her left cheek. She seems frozen in place, with eyes wide as saucers and not saying a word.

"Jack! What in the heavens are you doing!" - exclaims Dennis towards him.

"Calm down, it was a joke! She said I could do whatever I wanted hahaha." -- he says laughing.

"I see... a joke..." - says Dennis uneasy.

Lilly starts to laugh, and soon Dennis joins too, trying to make the situation less uncomfortable. Jack is slowly rubbing his bulge on Lana's face as they continue laughing.

"Okay, that is enough hubby, poor Lana." - says Lilly warmly. Jack makes a disapproving sound ('Tsk') but goes back to his seat.

"I a-am o-okay..." - she stammers back. "Sorry Dens, I did say he could do whatever he wanted at his house."

Dennis looks at her incredulous, although he has a stiffy in his pants. He ponders that it was due to the shock of the situation, not that he found it arousing. No, not at all.

"I g-guess you did..." - he says. "Even so, not cool dude." - says Dennis towards Jack, who laughs.

"Okay everyone, time to clean up lunch. Lana, be a dear and help me please?" - asks Lilly going towards the kitchen. "Next time is your turn." - she says to Jack.

"Of course, my pleasure." - says Lana getting up and picking some dishes. Her nipples are visibly hard making small bumps on her dress.

"Dennis, I have to answer some messages from my boss, can you please go supervise Evan? Thanks, I will join you soon." - he politely asks his neighbor.

"Sure thing, I know how it is. Evan seems great." - says Dennis, going to the living room.

Some time passes while the two women clean the kitchen. They chat and talk about their lives.

~~~

Lana is bent over the sink cleaning some dishes when she suddenly hears noises and turns around to see. Jack is behind the marble island with his phone held up.

"J-jack, what are you doing?" - asks Lana perplexed.

"Taking photos of your ass, what else?" - retorts him, like it was the most common thing in the world.

"You can't just keep doing things like this... me and Dennis do not like it." - she says trying to sound firm but failing.

"Oh darling, it's a great idea!" - says Lilly happily to Jack. "Lana let's take photos to celebrate the occasion!" - she proposes, dropping her cleaning cloth.

"I guess so, should we call Dens?" - the naive teacher asks hesitant.

"No need, he will join us soon." - assures Jack.

"Yay! Lana, follow my lead." - instructs Lilly clapping.

Lana puts the sponge and dishes back in the sink.

Lilly stands next to Lana and strikes a simple pose. Lana copies and Jacks snaps a few pics and gives them a thumbs up. They continue taking some simple pictures for a couple minutes.

"Okay Lillykins, time to turn it up." - Jack says making an up gesture.

"Lana, turn and give me a hug, then look sideways to the camera." - she orders her neighbor.

They take a few photos like this, some closer, some further apart.

"Okay now since we are hugging, this one will look nice. Copy me." - Lilly instructs.

Not breaking the embrace, she then bends slightly forward. Lana does the same. Lilly then quickly gives Lana a peck on the lips.

"Eep..." - Lana protests caught off-guard. "A kiss?"

"Sorry, didn't mean to surprise, but wanted to see if Jack could capture your reaction." - says Lilly.

"I didn't, too quick. Can you too do it again but stay like that for a bit?" - orders Jack.

Lilly looks at Lana who seems a bit flustered by the idea.

"Don't worry Lana, it will be a nice photo. It's all innocent and Dennis will love it!" - she says with a smile.

"He will? Maybe..." - she says awkwardly.

"You agreed to the photos, you wouldn't have lied to me, would you?" - Lilly teases.

"I wouldn't! Fine... we can do it..." - Lana says quietly.

Still embracing, Lilly kisses Lana again, holding the pose for several seconds. Jack takes a ton of photos from multiple angles. Lana is visibly red in every photo.

Jack realizes Lilly is doing a great job pushing Lana's boundaries, so he decides to stay invisible for now, pretending he is not there. Lilly seems in control.

"Okay, now hold my breasts with your hands!" - Lilly instructs like it was a normal thing.

"What? I can't do that." - Lana says aghast.

"Ah is just fun between us girls, it's normal. Besides, you agreed." - the middle-aged wife reasons.

"I guess..." - she reluctantly accepts.

Lana releases her hands from Lilly's back and stretches them forward, softly grabbing the small breast in each hand. Jack takes more photos.

"They won't break, you can squeeze and grope them harder." - commands Lilly.

'Grope them? Am I groping her breasts... oh my.' - Lana reflects starting to get horny.

Nodding her head shyly, Lana grips her breasts stronger, squeezing them with her hands.

"My turn!" - the wife says quickly.

"You can't..." - Lana protests weakly.

"Don't worry, your fiancee will love it! You will see." - she explains. Lana nods.

Lilly proceeds to grope and squeeze Lana's breasts above her dress. She is handling them with care but expertly, making Lana get even more excited. Lana's nipples start to visibly harden again.

Jack's fingers can't take photos quick enough.

"Okay dear, now turn forward and let me grab you from behind." - Lilly explains. "Are you having fun?"

"S-sure... this is fun..." - says the naive fiancee, still torn between desire and morals.

Lana turns towards the marble island and looks at the camera. Lilly stands behind her and continues to grope her breasts. Jack makes a subtle sign towards his wife.

"Oh dear, I think this outfit is not very flattering on you. You want these photos to look the best for Dennis, right?" - she questions her, releasing her boobs.

"Of course, I always want to look my best. I didn't know it wasn't good, what can I do?" - the young teacher asks nervously.

"Well, you have big, beautiful breasts, but this dress is hiding them and making them look flat and small." - Lilly states. The flat and small part was not genuinely true.

"What? Really? Oh no, I want to look good." - Lana says troubled.

"Okay, let me unbutton a couple buttons." - she explains, and Lana looks worried for a second. "It will look much better, Dennis won't be able to take his eyes off you!"

"Are you sure?" - Lana asks uncertain.

"Positive, I know how to keep my man happy. And this will make Dennis happy." - elaborates Lilly.

Lana nods and closes her eyes. Lilly slowly unbuttons her top 3 buttons, showing a little bit of cleavage and the utmost top of her bra-encased breasts.

"G-good?" - stammers the naive teacher.

"Maybe, let's take some more photos." - says Lilly, grabbing Lana's breasts again. She flinches at the initial touch but continues to pose for the camera.

Lilly continues to grope Lana's big tits and she moans softly each time. Jack makes another discreet hand gesture to his wife.

"Much better, but maybe we can improve it even further." - she states calmly.

"How?" - asks Lana curiously.

"You know how every man likes to see two women kissing?" - Lilly asks the young brunette.

"They do?" - she says shocked and looks at Jack. He nods vehemently.

"See. They all do!" - Lilly exclaims confidently.

"I had no idea..." - says Lana her mind wandering. "Does Dennis enjoys it too?"

"Every man, without a fault. Trust me." - Lilly states. "Let's give Dennis a special last photo, I bet he will come just looking at it!" - she continues.

"Wow... what do I have to do?" - the innocent teacher asks, a little excited.

"Turn your head sideways, part your lips and stick your tongue out slightly, I will do the rest." - she explains to her neighbor.

Lana shyly does as she is told. Lilly then meets the teacher's tongue with her own and goes in for a full kiss. Lana is so surprised by it that she goes limp and accepts the kiss.

Lilly continues to french kiss the young fiancee, gradually increasing the intensity of it. Lana's breathing accelerates and she starts to moan and get wet between her legs. She is really getting into it.

Deftly, Lilly uses one of her to unbutton more and more of the neighbor's dress buttons, until the dress is open halfway down her large breasts. She then starts to fondle them directly over her bra, Jack capturing everything. Lana moans louder and louder.

'Oh my... she is kissing me... this is not a cute kiss... this is a sloppy one... with tongue... she is good. Better than Dens? No... good... but different.... I like it. She tastes sweet and soft... mmm... I hope Dens likes the photos... mmm this is hot... I am getting so wet...oh she is playing with my boobs... feels good... I mean, Dens will love it... yessssss... play with them...I am getting there...' - Lana says in her head.

"What is going on here?" - inquiries Dennis entering the kitchen.

Lana and Lilly break their make out. Lana is panting hard and is very red on the face.

~~~

"Denny-boy! Welcome back, where is Evan?" - asks Jack, stopping with the photos.

"We played for a bit, and he is napping on the couch. What is happening?" - he asks again a little upset.

"Oh, just taking some photos." - the neighbor answers. "I will share them with you, they are so hot." - whispers Jack quietly to Dennis.

"They are?" - he says, getting excited thinking about the girl-on-girl photos of Lana.

Lana then rushes to Dennis and hugs him. They exchange a quick conversation. She doesn't button up her blouse, leaving it quite open.

"Sorry dear, we got carried away. Are you mad?" - she asks shyly.

"No, of course not. I was just curious babe." - he says genuinely.

"We kissed a bit for the photos. It was for you. Sure you don't mind?" - she asks worried.

"Not at all, besides, don't worry about kissing another woman." - he tells her.