Naive Teacher in Winston Ch. 04

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Stretching, touching, male anatomy and masturbation.
16.8k words
4.75
37.9k
50

Part 4 of the 18 part series

Updated 03/28/2024
Created 12/16/2021
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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.

Sorry it took so long, was very sick during the holidays. Now that work started again, future chapters might take a while to come, but they will.

This chapter will be slightly bigger than normal as a thank you for reading!

This story is a slooooow burn.

This is the fourth chapter of the misadventures of a Naive Teacher. It is strongly suggested that you read Chapters 1-3 first.

This chapter contains the following School days schedule:

* Day 4 -- Morning: PE --- Lunch --- Afternoon: PE --- Clubs: Staff Room

* Day 5 -- Morning: Bio --- Lunch --- Afternoon: Staff Room

Enjoy the read,

~ Potato Head

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

Day 4 -- Thursday

Early Morning

Lana wakes up with an immediate need to pee. She glances at Dennis' alarm, and it reads 6:24am. She silently gets out of bed as to not wake her tired fiancee and tip toes to the bathroom. She quickly sits down and starts to pee. Oh, sweet relief. She glances down at her panties.

'Oh my!' - she exclaims in her head. 'What a mess...'

Her panties were stained and dried up. She had never woken up having made such a mess. She realizes mid-pee that she is still feeling horny. She needs relief. Maybe Dennis will have time tonight.

Trying to beat the horniness, she gets up and makes her way to the kitchen to prepare breakfast. When she is almost done, Dennis joins her, and the couple enjoys a calm meal together.

"These eggs are fantastic babe!" - He compliments. "Also, sorry about last night, Lucius' secretary gave me a pill and I got extremely tired." - he explains.

"Oh no! Is everything okay?" - she asks worried.

"Yeah, it was a big headache. Weird that I got so lethargic after taking the pill, but at least I feel fine today!" - he says flexing his arm playfully.

"That is good..." - she can't hold her curiosity for too long. "Is his secretary pretty?" - she asks.

"A beauty! And excellent at her job." - he blurts without thinking. "Sorry, she is an executive assistant, need to get on with the times." - he says hurriedly.

"Oh I see." - she says with a hint of jealously.

He laughs out loud. "Don't worry babe, she would never give me the light of day. You are the only one for me! Besides, she is dating my coworker Paul, we are on the same team, and he is a nice guy." - he assures her.

"Ah, okay!" - she answers. "Hopefully I can meet your team soon."

"Oh! Forgot to tell you!" - he says. "Lucius invited the team to a dinner at his house on Saturday! You are invited too." - he smiles.

"Who else is coming?" - she asks curiously.

"Well, Lucius' wife will be there. Your colleague Mary. Also, the 3 other members of my team, Paul, Justin and Noel. And Lucius' assistant, Cynthia, will be there too. So, you get to meet all of them!" - he answers.

"Oh god, a lot of pressure. At least Mary will be there to keep me company!" - she laughs.

"Yeah, we will talk a lot about work haha" -- he chuckles. "Oh, speaking of work, tell me about your day yesterday!" - he asks with a hint of curiosity. He got a little horny every time he thought of the situations that were happening to Lana. Weird, he never felt like this before.

"Y-you sure?" - she asks uncertain. How would she explain everything to him? She felt butterflies on her stomach at the thought.

"Of course, I want to know about my babe's day." - he reassures her.

"Okay... well, in the morning, one of the students was apologizing for the skirt incident and then sent me an image by mistake!" - she exclaims in mock horror.

"Oh, who was it? And what did they send? Some funny video or something I bet haha" -- he chuckles.

"Nooo... Lukas Hunter..." - she whispers to him. He nods. "He accidentally sent me a photo of his big penis!" - she says, covering her mouth.

Dennis seems shocked. He never heard his wife call it a 'penis' before, she always said 'peepee'. And did she say he was big? He must have heard it wrong. He needs to play it cool, she dislikes when he is jealous without a good reason.

"Hahaha, probably an accident! Kids these days are always sending what they call "dick pics"! - he says, trying to sound in the know.

"Dick pics? Are they?" - Lana asks shocked by the revelation.

"Yeah! This Gen Z is exploding with hormones all over the place!" - he continues laughing.

"Oh! That makes sense then. When I got to school, I saw one of my students masturbating on the women's bathroom!" - she says sounding shocked again.

"O-oh r-really?" - he says, visibly disconcerted. "What happened?"

"Well... I was peeing and I heard some moans. When I was leaving my stall, I glanced at the next stall and saw her touching herself!" - she says flushing.

"At school? What was she doing?" - he asks. He can feel the blood flowing to his nether region.

"Yes! She was naked from the waist down and was using both hands!" - she says mortified.

"Where was she rubbing?" - he asks, wanting to hear more details.

"One hand was on her vagina and the other was on the clitoris..." - she whispers with her face beet red.

"Did you spy on her? Describe more to me, seems kinda hot." - he says.

"I couldn't help it Dens, she was right there, with her coochie in view." - she says quietly, starting to get horny remembering the scene.

The couple is interrupted by Dennis' phone ringing. It read "Cynthia" on the caller id with a photo of a pretty blonde showing some cleavage. Dennis picks it up and has a quick conversation.

"Sorry hun, Lucius wants me bright and early this morning, final adjustments to the presentation, you know." - he says sounding a bit sad. "Tell me more about your day tonight, deal?"

"Deal! Bye Dens, have a good day" -- she says, giving him a peck on the lips.

He grabs his stuff and hastily leaves for work.

She feels a bit relieved that she didn't have to tell him about the Bio class, when she showed her bra to her students, culminating on them seeing her naked breasts. By accident of course.

'Why I am feeling like this? This is wrong... I am not going to do anything lewd today! I will be a proper fiancee for Dens... it's not that I don't like it...I mean... no... it's wrong, I don't like penises. Yeah. Or showing off my body. No.... I don't. It's wrong. It's not proper. I won't do something I shouldn't in secret from Dens! If I don't do anything, I don't have to tell him anything... Right... I will be a good teacher... no looking at thick penises or showing my slutty boobs to people. Good, time to go be a proper teacher and fiancee.'

Deciding to start over from the last two days, Lana cleans up after breakfast and gets ready for school. She opts for a button up long-sleeve light blue blouse, a little form fitting, and a blue knee length skirt, which accentuates her hips well. She goes with blue cotton panties and simple bra to match.

As she walks to school, she remembers that her first period is PE. She looks at her outfit, not at all gym appropriate. Hopefully she won't have to participate in class.

~~~~~~~

Morning -- PE

She makes her way to the Staff Room to drop her belongings. There aren't any other teachers around to chat, so she decides to kill a bit of time. She is going over some materials for tomorrow's Sex Ed class, when she notices a door in the middle of the room.

The sign at the door reads "Staff Bathroom".

She almost facepalms when she realizes the masturbation incident from the day prior could have been avoided. The teachers had their own bathroom!

She makes her way inside, ignoring a small note below the lavatory sign. She turns the lock and sits down. The single bathroom was spacious, with a big sink, mirror, counter, chair, toilet and even a urinal, for the male teachers. Interesting and way better than the student's one.

She is going about her business when the door opens and Roger walks in. He stops in his tracks.

Roger has a nice view of her blue panties around her angle and can even see a bit between her legs, with her brown pubic hair making a slight appearance. His view is mostly obstructed unfortunately.

"Roger! I am in here!" - she screams still peeing.

"Oh, sorry Lana, I didn't mean to barge in." - he says, not moving an inch.

"Go away! I am on the toilet!" - she says louder.

"I can see that..." - he smirks while ogling Lana.

"Go! How did you get in...? I locked the door!" - she says trying to understand.

"Oh, the lock is defective, there is a sign and everything." - he says as if stating the obvious.

"Let me pee! Go!" - she shrieks loudly.

"Okay, nice pubes. See you at PE!" - he winks at her and leaves.

She is dying of embarrassment, Roger has just seen her sitting on the toilet. And apparently, he saw her pubes? Maybe he said it wrong.

She finishes peeing and washes her hand. She is extremely red.

'This wasn't anything lewd... it was an accident, accidents don't count!' - she reassures herself.

She finishes her business, grabs her materials and goes to the School Gym.

~~~~

Most of the students are already there, all wearing some sort of gym attire. She looks a bit out of place wearing her teaching outfit, she will have to talk to Roger about it.

The Gym is big, with a basketball court, a volleyball court and an area with lots of mats, probably for Yoga or Wrestling. On one side there are bleachers where spectators can cheer for their school, while the other side has benches for the students and the locker rooms, complete with showers and bathrooms.

Lana joins her fellow teacher in front of the students, and they wait silently until the last students arrive, which are BJ and Wyatt from her class.

"Welcome students to PE class! Miss Cox here will take care of the girls and I will oversee the boys, mostly." - he introduces. "Lana is everyone present?" - he asks, turning to the naive teacher.

"Yes, all 28 students accounted for. 17 boys and 11 girls." - she says, scribbling on her clipboard.

"Very well. Today we will do things a bit differently. For the morning, I will go discuss the lessons plan with Miss Cox and your lot will go play some sports." - he announces.

"R-right. Chloe..." - she says, directing her attention to her blonde student. "Since you are captain of the volleyball team, can you lead the girls to play some volley?" - she asks a bit uncertain.

"Of course, Miss Lana, it will be my pleasure! Let's go girls." - the blonde student says leading the ladies to the volleyball court.

"Good idea Lana! Andrew, take this lot to play some basketball for the morning." - orders Roger.

"Yes sir, will do. Come on boys, follow me." - says Andrew, clearly in control of the males.

Roger motions to Lana and they make their way to the benches in front of the locker rooms.

"Okay Lana, sorry about earlier, I was so shocked I couldn't think straight." - he apologizes.

"Ah, it's okay, it couldn't be helped. The lock was broken, and you didn't know I was in there." - she says, promptly accepting his apology.

"That is right. Oh, before we start, since we were in such a hurry, I didn't get my hug." - he says, opening his arms.

"O-oh r-right, almost forgot." - wavers the innocent teacher, hugging him.

He quickly breaks the hug and brings her closer to him. "So, about PE, let's go over some of the classes." - he says. She feels his breath on her face, he smells minty.

They go over the first few classes together. It takes a good portion of the morning and Lana is impressed that Roger has a lot of the lesson plan all thought out, or at least the high-level program. Of course, the minutia of her classes was up to her.

"(...) Ok, this is enough for the first few weeks." - he says, finishing the conversation.

"Thanks Roger, I appreciate the help." - she answers honestly.

"Any time beauty, any time. I am here to help you with anything you need and answer any questions you might have." - he says, smiling warmly at her.

"About that..." - she says blushing slightly.

She glances at the students to make sure they are not paying attention and are still playing. They are.

"Tuesday, some students called me a Paug." - she whispers quietly to him.

"What was that?" - he asks, with a slight smile.

"Paug? Poug? Pog?" - she whispers a little louder.

"Oooohhh, a PAWG!" - he says with a slight chuckle.

"Yes! Pawg! What is that?" - she asks innocently.

She is not ready for what he does next. He lays his hand on her butt. His whole hand, open palm against her left bum cheek.

"Hey! What are you doing!" - she exclaims surprised while blushing furiously.

Some students discreetly turn to see what is happening with their hot teacher. Roger removes his hand from her ass and puts a finger on her lips.

"Shhhh, they might hear you... When did they say that?" - he asks quietly, ignoring the fact that he just palmed her butt.

"W-when they saw my buttocks in the cafeteria..." - she says softly, still blushing.

"Oh right, when you showed your big ass to all the students." - he states with a chuckle.

"I didn't show it! It was an accident!" - she protests loudly. More students turn to see.

"Riiiiight, and you didn't like it one bit." - he says laughing softly.

"I didn't! That is irrelevant. What does 'pawg' mean anyway?" - she asks curiously.

"It means Phat Ass White Girl." - he says nonchalantly.

"W-what... the students said that to me... their teacher..." - she blushes and lets her mind wonder.

"Yeah, I guess they did because you wouldn't know the term and also because it is true." - he states and touches her ass again. She doesn't seem to notice.

"It's not! My ass is not fat!" - she protests, jutting her backside out a bit to prove it. She was proud of it, one of the reasons she spent so much time at the gym. She wanted Dennis to be attracted to her.

He controls himself not to squeeze her enormous butt, as he didn't want her to realize what he was doing. Meanwhile, quite a few of the students were looking and some even taking pictures.

"Noooo, you misunderstand. The ass is not fat, but 'phat', with 'ph'." - he states as if obvious.

"Aahhh...." - she says, as if understanding it. "... how is that different?" - she asks confused.

"Well, 'phat' with 'ph' is a compliment. It means thick. It means the students are attracted to your sexy ass. They liked seeing your juicy bubble butt. You should be proud." - he says condescendingly.

"O-oh, I s-see..." - she says feeling hotness between her legs. She was suddenly aware of his hand touching her bum. She feels her head spinning. She needs to stop this, it is not proper.

"Anything wrong?" - he asks with a sly smile, noticing the teacher seemed disturbed.

"Your hand... is on my... butt..." - she says quietly while pointing at it.

"Ah sorry!" - he removes it. "Must have been reflexes when I talked about your big ass." - he explains.

"P-please don't do that again." - she says, trying to sound firm.

"Sure, as you wish, Lana. I won't touch your phat butt for now." - Roger says with a smile.

"Wha..." - she starts to protest.

"Ah! That reminds me, we need to talk about your PE uniform." - he says quickly changing subjects.

"U-uniform? What uniform?" - she asks confused, forgetting about what had just happened.

He looks at her with a raised eyebrow and points at the students, then at himself. She turns and realizes that, while all the students are wearing gym clothes, they seem to be only wearing a combination of red and white pieces. Indeed, it does look like they are wearing a uniform. She facepalms.

"The students wear Red and White, while the teachers wear Gray." - the male teacher explains.

She looks back at him and takes a good look at his uniform. He is wearing a gray tight fitting tank top and matching gym shorts. Lana for the first time realizes that Roger is exceptionally fit, way fitter than Dennis, who is at the same time skinny and out of shape. Roger on the other hand, is muscular and toned, with a proper gym body. She can't help but feel a little attraction towards her colleague.

"Sorry, I hadn't noticed we had uniforms." - she says, pointing to her teaching outfit.

"Clearly, we have uniform tops..." - he points and his broad chest. "And bottoms." - he then points directly at his groin region.

She stares, noticing that the shorts he is wearing are loose and she can make out a little bit of his bulge. She starts to feel her chest heat up and tighten, but tries to shake the feeling away, it is not proper to think about sexual desires, after all she has a fiancee whom she will marry.

"Ah, your shorts are too small..." - she says blushing.

"Yes, yours will be too. These outfits are made to provide freedom of movement, like this." - he says as he starts to move around a bit, emphasizing his pelvis.

Lana has a clear view of his penis bouncing around on the inside of the shorts. She follows it enthralled.

"Oh wow..." - she whispers, feeling her head spin.

"Glad you like him!" - he says with a smile, but she misses the double entendre. "We have female teacher uniforms on the teacher's locker." - he explains.

"Where is that?" - she asks curiously.

Sensing an opportunity to grope the naive teacher, Roger quickly comes up with a plan. Although Lana is such a naive pushover that almost any plan would work on her.

"I can show you later, first we need to measure you." - he states.

"M-measure? I can tell you my size." - she stammers back.

"We have special sizes here in the school, so we need to do it. It is part of the rules, they measured me too for this uniform." - he explains.

"I g-guess it c-can't be helped then." - she nervously says.

"It can't! Now turn around and let me see your bottom." - he orders firmly.

She blushes, puts her clipboard down, lowers her head and obediently turns around.

"Arch your back, we can't see well enough." - Roger commands again.

The "we" was missed on her, but it referred to a bunch of the students that were glued to the situation. They seem to have completely forgotten about their practice.

She shyly arches her back, attempting to emphasize her bottom while struggling not to think about what she is doing. Her chest is feeling extremely hot.

'I am not showing off to him... this is not lewd, it is just how it works... it is not like I did it on purpose, Roger said is part of the process. Right.... The process... I am just following it... I think he had enough ogling... I mean... measuring...'

"Okay, that is good enough. Bottoms size medium." - he then slaps her ass lightly.

"Hey!" - she protests.

"Now let me get the measuring tape..." - he says ignoring her and rummaging through his stuff. "Found it!" - he announces.

"W-where are you going to use this?" - she asks uncertain.

"On the top! The bust is way more difficult, so we need to measure properly." - he says nonchalantly.

"No! You can't do that." - she looks shocked.

"Is either that or getting a small size and having your big tits spilling all over the place." - he explains.

"B-but the..." - she starts to protest again.

"Do you want the students to see your boobs? What a naughty teacher!" - he teases her.

"N-no, I am not! I am proper and I shouldn't show them my breasts!" - she says trying to explain.

"Okay, it's decided then, let's measure." - he says simply. "Now be a good teacher and stand still." - he orders. She nods her head visibly embarrassed.

All the students are looking at this exchange, lots of them not quite believing their eyes. Yes, rumors were spreading about the new naive teacher, but seeing is believing. Half of the boys were filming it.