Naive Teacher in Winston Ch. 09

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The foul elderly man snaps another photo and presents it to his daughter-in-law.

"Hmm... something is missing... I need to pose next to her. Yeah." - Lilly decides, clapping her hands.

She stands next to Lana and rests her chin on her big bubble butt. She sticks her tongue out mischievously.

'She is so close to my butt, hopefully it doesn't stink. No, I'm clean... wow... this old man has a massive hard-on... erm, erection I mean... that is so improper... just looking at my anus made his dick hard... I mean penis...' - she thinks, the situation muddling her thoughts.

Jack Sr. takes another picture and Lilly goes to his side to take a look.

"Gah... still not perfect... Ah! I have an idea. Lana, bear with me, please." - Lilly warns her, coming back to her side.

She suddenly feels something prodding at her budding orifice.

"Eeek! What are you doing!" - the brunette teacher protests.

"Relax, I am just poking your ass with my finger... it'll look great!" - the wife explains, slowly jabbing at the entrance.

"Be c-careful, it feels w-weird." - Lana says with a horny tone.

She unconsciously arches her back even more, lifting her enormous thick rear.

"Wowza... it's huge!" - the elderly overweight man comments quietly, clearly impressed.

"Ready, dad. Take the photo!" - Lilly asks with a smirk.

She thrusts her index finger inside Lana's virgin butthole. Just up to the end of her fingernail.

"Eeeeeep!" - the gullible neighbor shrieks in surprise.

Lilly slaps her ass with the other hand.

"It's for the picture! Cooperate! The more you move, the longer it takes." - Lily explains sternly, feeling slightly frustrated.

"Stay still pumpkin, we're almost done." - the ugly old man says.

Feeling very uncomfortable, Lana tries to come down from her shock.

'Oh, no... Lilly has a finger up my anus... it doesn't feel as bad as I thought... I don't feel anything. I mean, it feels wrong, I shouldn't let her do it... no, we are just about finished, so I will endure it for now.' - she makes up her mind.

"Okay..." - Lana whispers sheepishly, turning towards the camera and smiling.

The senior man didn't waste any time and snapped a pic.

The scene was bizarre.

Here it was, our naive virgin teacher, with her dress hiked and her panties partially peeled, exposing her pink asshole to two people, one of whom she had just met. The old man had a massive stiffy in his pants, while the middle-aged woman had her fingertip inside the teacher's anus.

What a weird and freakishly sexy situation.

Lilly removes her finger with an audible *Pop*. She giggles and joins Jack Sr. to check on the photo.

"Much better! This is great. Thanks, Lana, for being a good sport. We are done." - Lils announces.

Lana breathes a sigh of relief and starts to move to adjust her dress when she is interrupted.

"Can I also take one? As a souvenir! It has been years since I was in the presence of such a pretty young lady." - he asks with a pervy grin.

"It's a good idea dad. I don't see why not!" - exclaims Lilly, clapping her hands.

"Ahm... are you sure Lilly?" - the credulous Lana asks with worried eyes.

"I wish to remember this day on my deathbed. I beg." - the paunchy old man pleads.

"You surely can't refuse the wishes of a man who is dying... someday..." - Lilly comments, whispering the last part.

"Oh, no. I had no idea! I guess there is no harm in it then." - the naive teacher agrees reluctantly.

"Marvelous! Thanks, pumpkin." - the unattractive elderly man celebrates.

"Please, be quick, I can't be late for work..." - she says as Jack Sr. stands next to her.

"All ready?" - asks Lilly, holding the camera.

"One second, Lils." - he says holding his hand up.

Lana turns to look at the wall and takes a deep breath.

'This is ending soon...' - she thinks.

She is not paying attention, when suddenly she hears a gasp from Lilly.

"Dad!" - the lady of the house shouts.

The teacher looks back at Jack Sr. and she shrieks, startled.

"Eeeek! What are you doing!?!" - Lana yells, recoiling a bit.

You see, the reason why both women were taken aback was that the old man had removed his pants and underwear, standing there fully naked from the waist down. He was, as we call in the industry, 'Winnie-the-Pooh-ing'.

The teacher has a front row view of his wrinkly ancient sagging butt.

"Lils, it's just for the photo." - the ugly man says and turns to Lana, his hefty penis flopping around with the movement. "Apologies, I thought it was okay, since you did it with my son." - he explains.

Lana's mouth is agape. The old man's penis is huge, full of veins and wrinkles and covered in white pubic hair. It was currently 9'', standing at full attention.

'Eff! It's enormous... so hard... and thick... looks bigger than Jack's... what are people being fed in this town... every prick is huge... my, my... no, Lana, don't look... you need to stop staring at the fat dick... I mean penis... why is this making me wet? Just reflexes, yeah... why is he showing it to me? It's so nice... I wonder how it feels to stroke it... no, stop... Dens looks like a kid next to this senior man and his peen, covered in white pubes... it looks so nasty... so manly... hmm... control yourself, you need to answer him back...' - she thinks trying to fight her inner lust.

"Erm... eh... I s-see... ahm... o-okay..." - she stammers, her brain malfunctioning over the sigh of the monstrous snake in front of her.

"See! You worry too much, Lils. Pumpkin here says it's dandy." - Jack Sr. says.

"If she says so." - Lilly shrugs. "All ready now?" - she asks.

The old man stands sideways, in order to give Lana a nice view of his wrinkly stiff cock.

"Ready and willing! Right, pumpkin?" - he asks. She nods absent-minded, still ogling his big member.

He rests his member on top of her butt cheek, she winces at the contact but moans softly, her sexual arousal rapidly ascending.

Jack's wife takes a picture and puts the camera down.

"Looks good!" - she gives them the thumbs up. "Are we done?"

"One more for good measure! Let me re-adjust!" - the crude white-haired man says.

He moves his penis away and the teacher whimpers lightly in frustration.

Nobody is prepared for what the perverted gross grandfather does next.

Jack Sr. moves behind Lana, and lines his old cock with her anal hole. He then moves forward and pokes her asshole with his dick head, trying to force it inside.

"Ahhhhhh!" - Lana yells, recoiling away from the hefty meat stick. She backs into the couch, scared.

"Dad! What are you doing!?" - Lilly shouts angrily.

"I was posing for the photo. I was going to put the tip in, like you." - the slimy man says nonchalantly.

"Not with your fat dick! You are scaring the poor thing!" - his daughter-in-law yells.

He looks at the situation, almost as if a spell has been broken. It dawns on him what he just did.

"Oh, pardon me. I got carried away, could not resist the temptation." - he says, apologizing to Lana.

'What just happened... Jack's old dad tried to put his penis in my anus... oh, no... is the first strange penis that makes direct contact with my sex... oh, wait... the anus is not a sexual part... so I think it's fine, it's not like it felt good anyway. He said he got carried away, so I will forgive him. Argh... no... not a big deal, Lana, you are still peachy.' - she tries to excuse it in her mind.

"Erm... it's o-okay... I f-forgive you." - she stammers, her heart beating a million times a minute.

"Get, out of here, now. We'll have a talk later." - Lilly tells the pudgy old man sternly.

"Hmpf." - he grumbles. "Bye now, pumpkin. Thanks for the memory!" - he says with a crooked grin.

"Y-you are w-welcome..." - Lana replies quietly.

"I can't wait for the boys from the senior home to hear about this and see the photos..." - he comments with a chuckle as he leaves the room.

Lilly approaches the brunette teacher and helps her get up from the couch.

"Sorry Lana, he's a big old pervert. He's also a bit senile, I should've warned you." - Lilly says to her neighbor.

"Ahm... I guess nothing bad happened, so it's all right." - the gullible educator concurs.

"Thanks for understanding. I'll have a talk with him." - Lils explains angrily. "You can go now and consider the bet paid!"

"Ah right, the bet. Thanks!" - Lana says, putting herself together and gathering her stuff.

The two women walk together to the front door.

"Ah, one more thing. Since it was Kenny's idea, I promised him you would show him the photo, pretty pleeease?" - Lilly asks with her phone in hand.

"Erm... sure, since you promised." - the busty neighbor accepts, still a bit out of it.

"Here, I sent it to you." - Jack's wife says, fiddling with her phone.

Lilly opens the door with a smile.

"Bye, neighbor, have a good day!" - Lana says.

"See you tomorrow night, thanks for stopping by!" - Lilly waves.

The buxom teacher starts walking towards school.

'Ugh... what just happened. No, let's not think about it, this was a one-off.' - she evaluates.

She picks her phone and glances at the pic that Lilly sent.

It was one of the first photos, showing her bending over the couch. Her dress was hiked up and her creamy butt partially exposed, with her beige panties pulled down and her pink bumhole in plain view.

In the picture. it looked like she was proud of displaying her asshole, due to her wide smile.

'Goodness... looks so naughty... so lewd... what am I doing, I look like a tramp...' - she complains.

She glances at the time and gasps.

"Oh, no! I am going to be late!" - she exclaims, troubled.

Lana starts rushing to the school building.

Actually, she was going to be just in time for the class to start, meaning she was not going to arrive early to have a separate Physical Checkup, as Roger requested.

Troubling indeed.

~~~~~~~

Morning -- PE -- Checkup

Lana quickly makes her way to the Gymnasium.

She spots a couple strangers to the side and a couple tents set up in the yoga/wrestling area. She ignores them and rushes towards the Ladies' locker rooms.

The future-wife dumps her stuff in the locker with the "Teacher" sign and picks her gym uniform. She removes her dress and then her bra, putting on the gray tank top with the built-in sports bra. It stretches tightly (and lewdly) across her big breasts, leaving her midriff fully exposed.

She decides to leave her beige granny-panties on, to avoid the 'accidents' from last time. Yes, her panties would be showing, but it was better than giving them glimpses of her vagina. Struggling, she manages to put on the stretchy gray leggings. They highlight her fat ass and wide child-bearing hips.

Checking the clock, she still had five minutes before the bell. She grabs her trusty clipboard.

'Have I made it in time? Hope so...' - she thinks, optimistic.

She hurries to the two tents, finding Roger with an impatient look on his face. The strangers she saw before are nowhere to be found.

"Lana! Where have you been? I asked you to arrive early!" - her colleague reprimands her.

"Sorry... I got... caught up... in something else... I could not leave..." - she says, out of breath.

"No excuses! You missed it, now you'll have to do the checkups with the students." - he states.

"There is still time... can I do it... now?" - she asks, still recovering her breath.

"We are out of time. Look!" - Roger says, pointing to the gym doors.

Lana sees the students trickling in through the doors.

"Over here!" - the male instructor shouts at them, signaling.

They come over slowly and stand facing their educators.

"Sorry..." - Lana apologizes to him sheepishly. She was feeling intimidated by his wrath.

"Your funeral." - he shrugs. "I was only trying to protect you, now you'll have to suffer through the examinations with all of them." - he explains quietly.

"Thanks for looking out for me." - she says softly.

He makes a big to-do of rolling his eyes, causing our protagonist to feel lousy.

'I feel awful for disappointing him. I wonder what he means by "it being my funeral". Oh, well. I will need to make up to him later.' - she decides.

The bell rings as the last student gathers in front of the teachers.

"Welcome students to PE class! Today, we will have our annual physical checkups." - Roger announces.

The students groan and complain, knowing what awaited them.

"Suck it up, we do this every year." - he says with a laugh. "Miss Cox, is everyone present?" - he asks her.

"Yes, all 27 students accounted for. 17 boys and 10 girls." - she answers, scribbling on her clipboard, knowing that Chloe was absent from class.

Two strangers come out from the inside of the tents. They are dressed up as doctors, in blue scrubs and white lab coats.

"Good timing. Everyone, most of you already know Dr. Hardik, from the clinic." - Roger introduces.

"Hello, hello, kids!" - the old man he greets with a grin.

Dr. Hardik is an older south Asian man, in his early-60s, with an Indian accent and a slightly perverted attitude. He is not tall at all, standing at 5'7 only. He is a great doctor, with dozens of years of experience under his coat and being the chief of the town's medical clinic.

"And this is Nurse Park, as you boys might know." - the male teacher winks.

"Thanks Roger. It's nice to see everyone again, keeping healthy!" - she says happily.

Nurse Park is a petite east Asian woman, in her early 30s with long black hair. She has a tight body with perky B-cups, and is always wearing some revealing outfits, driving all the men in town crazy. Even now, the scrubs somehow accentuated her fit body.

She had worked with Dr. Hardik for the last 10 years, and while sometimes she still helps out in the clinic, the Asian woman recently got promoted as head nurse of the town's senior/nursing home.

"Give us a few minutes and we'll start the checkups. We have some stuff to discuss first." - Roger tells the students.

The students disperse somewhat, forming small groups and chatting among themselves.

"Hi, Doctor, I am Lana Cox. I joined the school this year." - Lana greets him with a smile.

The old man opens his arms, and they hug.

"Nice to meet you, Miss Cox. The rumors are true, you are indeed stunning." - the old doc compliments.

"Aw, thanks. Hi, Nurse, I am Lana." - the teacher says, turning to the small Asian woman.

"It's great to finally have a girl of my age around here! Hopefully we'll become good friends." - she says enthusiastically.

"I hope so too, Nurse Park." - the busty teacher smiles back.

"Please, call me Vivian, or Viv for short." - the petite nurse says.

"Are you done yet? We need to start. Doctor, Lana will be the first to go since she missed the early call." - Roger informs the physician. "Remember what we talked about."

"Arre... I see, no problem." - the old Indian man says.

Roger calls the students back.

"Everyone pay attention! We'll start with Miss Cox here, she kindly volunteered to go through the checkup in front of you sorry lot." - the male teacher tells the students.

"Is that not what normally happens?" - she asks, confused.

"Sweety, we normally conduct the exams of the boys and girls, separately. I check the boys, while Nurse Park examines the girls." - the gray-haired doctor explains.

"But we always use curtains for privacy, since sometimes these checkups can get quite intimate." - the nurse adds.

"Ahm, I see. What is the difference?" - she asks.

"Well, rani, Roger asked me to demonstrate the checkups for the new students this year. So, we decided to examine you without the privacy screen and in front of all of them, no distinction between genders." - the old man explains nonchalantly.

'This is bad... do I have to be exposed in front of them? No, no... I doubt it, they seem professionals. They wouldn't do that.' - the naive teacher thinks.

"I told you to come early, Lana. I can't wait to see that." - Roger smirks.

"Ghanta, you'll do no such thing." - says the old man. "This is for the students, not for your eyes. Please excuse yourself while they do this, bas!." - the doctor looks at him sternly.

Roger lets out a frustrated groan and the students laugh at the teacher, who was expecting to be able to perv on Lana.

"Fine. Whoever finishes, can join me in the courts to play." - he says upset, leaving the vicinity towards the court.

Lana catches a glimpse of Nurse Park sticking her tongue out to the teacher as an insult. She giggles. She was starting to like this Vivian woman.

"Accha, Miss Cox, please follow Nurse Park inside, she will perform your examination." - the senior physician states.

Lana passes through the curtains, following the Korean woman inside the left tent, labeled "Boys". It's a small room with a high window to let in some light. There is a folding bed and a few medical apparatuses like a scale and a cart full of devices.

The teacher feels at ease. There was just a small gap through the curtains, where they came in from, so it looked like she was going to be safe.

"Lana, please undress to your underwear, while I set up." - Vivian instructs her.

The teacher nods and sits on the bed, with her back away from the entrance. She starts to halfheartedly remove her shoes.

Suddenly she hears a loud noise from behind her. She turns to see and gasps.

The petite nurse is pulling open the front of the tent. The front was basically a large white curtain, protecting those inside from prying eyes.

Vivian finishes opening the curtain and the result is that there is basically a huge open gap in front of the tent, leaving Lana fully unprotected from the 27 students.

'Oh, no... they all are going to see me being examined...' - she panics.

"Jhakaas! Much better, thanks Nurse Park." - the old doc grins. "Anything wrong, Miss Cox?"

"They are all going to see me in my underwear!" - she exclaims, exasperated.

"Do not fret, ishu. You'll be turned around, so the kids won't see anything more than your taut back." - the elderly Indian man explains.

"Ah... is that so? They won't see?" - the busty gullible teacher asks nervously.

"You're an educator, an example to these hoodlums, sweety. Don't be a fattu." - the doctor grins with a dismissive gesture.

"What Dr. Hardik means, is that this'll be important to set the new students at ease, knowing there is nothing to worry about." - Vivian interjects.

"Ah... okay... that makes sense." - Lana agrees innocently.

"Please, down to your underwear now, rani." - the old doctor orders.

She nods sheepishly and starts to peel off her gray leggings. Her beige panties come into view, but as she is sitting, the rowdy students only get a view from her back, which is fully covered by the modest underwear.

The students behind her start chattering about their sexy teacher.

She turns slightly to talk to the doctor, giving them all a side view of her creamy naked thighs.

"I am ready." - Lana says embarrassed. 'Oh, my... I'm in just a tight top and panties in front of all the students... this morning was supposed to be a one-off... no, calm down, Lana... you will show them more at the beach this weekend, no need to worry.' - she steels herself.

"Miss Cox, arre, you still have clothing on." - the old physician says, annoyed.

"Ah, hm... you see... this top has a built-in bra... so I am not wearing any..." - she stammers, trying to explain.

"It's okay, doctor. We can figure out a way around it." - Nurse Park comes to her defense.

Lana looks at her and mouths a 'thank you'. Vivian nods and smiles back.

"Bah, very well." - the senior Indian man grunts, turning around to the students. "Everyone, enough bak bak! Gather around and we will start the demonstration." - he shouts.