Naive Teacher in Winston Ch. 09

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"I cannot imagine a woman who would not want to have a taste of it." - she quietly reveals her secret thoughts to Herbie.

"Wow, Miss Lana. I feel much better." - the shaved boy says with a wide grin.

The rest of the examination proceeds as well as it can. Lana can't help but tremble and moan every now and then as she handles the big organ in front of her.

"Nine and a half inches! Dear... what have they been feeding you, it's the biggest of the day." - she exclaims, amazed by her student.

He smiles proudly, his ego fully inflated.

'I've never seen any prick like this before... not that I have seen many... wait... maybe now I have! I saw all my student's willies, and Roger, Jack, Jack's dad and Dens. My word! How did I go from seeing one peen to over twenty, in a few days... so wrong, improper... but also exciting...' - she thinks, amused.

The doctor finishes the exam, and the boy is about to leave when he turns towards his teacher.

"Erm... Miss Lana... can I have a quick kiss? I never kissed anyone and wanted my first time to be with the woman I have feelings for." - he asks quickly.

Not understanding fully what the boy meant, the teacher approaches him.

"Of course, Herbie. Here is a nice mouth kiss as a reward for being a good boy." - she says with a teasing tone.

Since they were basically the same height, the teacher unceremoniously smooches her mouth directly onto his chubby lips.

They kiss for a few seconds, and she breaks it, stepping away with a dreamy smile full of desire.

"Wow, that was amazing. Thanks Miss Lana. Hope to see you on Sunday, doc!" - Herb says before disappearing out of the tent.

"One to go." - Lana says, turning to the old man. "Hum... are you planning to come this weekend?" - she asks nervously.

The last thing she wanted was this lecher old man groping her in front of her fiancee and the whole town.

"I'll think about it. Seems like a good opportunity to see you again." - he gives her a yellow toothed grin.

"You do not have to come..." - she starts to say, but she is interrupted by the arrival of the last student.

~~~

Greg Zimmer

In comes Greg, the boy who is playing Lana's son at the school play. Besides that, the teacher didn't know him well at all, just that he is a short boy who is extra overweight.

"Helloooo..." - the boy says with apprehension.

"Mr. Zimmer, come in. You are the last one." - Dr. Hardik states.

"Hi Greg, it's good to see you again after yesterday." - the teacher smiles.

"Good to see you also, Miss Lana." - Greg says.

For the final time, the examination goes smoothly and nothing sexual happens.

Lana notices that the boy seems down during the whole session. The exam is almost over when the teacher decides to ask him about it.

"Greg, I could not help but notice that you look sad. Anything wrong?" - she asks worriedly.

"Ah, nothing. It's just... never mind." - he dismisses quickly.

"You can tell me, I am here to assist you!" - she says, flexing her arm.

"Are you sure?" - he asks wide-eyed.

"Of course, I will do anything to help my students. And in a way, you are my student, we are in the Drama club together." - she says warmly.

"Erm... I am embarrassed." - he admits, his face flushing.

"By what? You seem fine and healthy to me." - she says with a big smile.

"My dick... is too little." - he says with his head down.

'Ah... another one... what is it about boys and their size... it is tiny... poor boy... no stop, don't make fun of him. You should help him, it's your duty as his mentor.' - she ponders.

"Most men are small when soft." - she explains, trying to reassure him.

"Really? I don't think that's true." - he says unsure.

"It is true, right Dr. Hardik?" - she asks the old man, who nods vehemently. "See, there you go."

"I don't think it's much bigger when I have a boner." - Greg says gloomy.

"It probably is. Why don't you show me?" - she asks with second intentions.

"What should I do?" - he asks, clearly nervous.

"You can touch yourself." - she suggests with thirst in her voice.

"I've never done that in front of anyone before!" - Greg explains with big eyes.

"How about this, I'll touch your weenie and make it erect. Sounds good?" - she says aroused. 'What am I saying... I keep offering myself to the students... what is happening to me? Ugh, too late now.' - she reflects.

"Okay, Miss Lana, but please don't laugh at it." - the boy says with sadness.

"I would never do that! Let me help you..." - she says.

Lana doesn't waste time and wraps her glove-covered hands around the small, shriveled shaft of her student. She starts to rub and squeeze his diminutive penis.

She glances up at him as he is staring at her with fire in his eyes. His cheeks are flushed, and his breath is quickening.

With a naughty smile, she starts to jerk it rhythmically, basically giving the boy a hand job.

He starts to moan and pant, closing his eyes trying to contain his ejaculation.

In a few seconds, his young smooth cock is hard and pulsating in her hands.

"See, that does not look bad at all!" - the teacher says.

"Liar, it's small... only five inches...it's pitiful." - he says mournful, his penis deflating.

"Stop it Greg, your penis is bigger than my fiancee's." - she admits. 'It's true... even this chubby teen's wiener is bigger than Dens by half an inch. It's not by much... but still...'

"You are just saying that to make me feel better." - he complains, downhearted.

"It is the truth. I am with him, and he has a small peepee." - she says, still holding his now limp willy. 'Why am I telling him this? Sorry Dens, it's just so he can feel better.'

"No girl would want to be with me." - he says depressed.

"Do not get dispirited... I promise you, it is average!" - she tries to pep him up, letting go of his member.

"I will be alone forever." - Greg says with teary eyes.

"Do not dare say that! You will find someone who loves you." - the teacher says, holding his hands.

"No! Nobody can love a man with a tiny dick." - he says with tears running down his fat cheeks.

"I do! I love my future husband, even with his below average weenie." - Lana says, squeezing his hand tightly.

"He must be handsome or rich..." - the chubby boy says, crying.

"Beyond all he is a great person! Like you!" - she says, and he sniffles.

"Maybe he is great in bed then! I wouldn't know what to do, I'm a virgin." - he complains downcast.

"He is not very good... well I would not know either, I am a virgin too." - she declares, embarrassed.

"Really? No man has put his cock in your pussy?" - the overweight boy asks, wiping his eyes.

"Not at all... my coochie is chaste and pure." - she admits timidly.

"Huh... so even a busty sexy lady like you can love a wimp like me and him... without having any sex..." - the boy says to himself. The teacher nods encouragingly.

"How can this teacher assist you, Greg? I will do anything." - she declares trying to lift his spirit.

"Anything? Promise?" - he asks, wiping his tears.

Reality was, Greg was indeed depressed about it, for a few years now, but he was also a talented actor. The boy ended up acting it up for the teacher so she would pity him and spend longer by his side.

You see, Greg didn't do it out of malice or second intentions, for once in his life he felt good being on the receiving end of someone's affection and got carried away.

The chubby boy was extremely lonely, with no friends or a caring family, so this was a unique moment for him.

"Yes, I swear on my role as an educator. How can I help?" - the teacher says affectionately.

"Caham... may I make a suggestion?" - the old doctor interrupts with a kinky hint in his voice.

"Sure, anything to help him get over his slump." - Lana answers with determination.

"How about you masturbate him?" - the elderly man says clinically.

'Oh, I knew it... this pervy old fart... what is he up to... hmpf...' - she rages in her head.

"Ye-ye-yes... pl-pl-ple-please..." - the boy stammers with red eyes.

"Erm... how is that going to help? He is already hard." - the teacher says trying to find a way out.

"No, to completion. Make him ejaculate." - the Indian physician states with a smirk.

"If Greg was not here, I would have kicked you out." - Lana tells the doctor, enraged. "What does that have to do with his mental state?" - the credulous teacher asks, trying to legitimately understand.

Secretly, she was also quite intrigued by the idea, her body still horny from all the penises she interacted with during the day. She wanted to be pushed further, she just didn't know it.

"It would help give the boy confidence, since he never had contact with a woman." - the elder white-haired doctor explains.

"Is that your professional medical opinion or your perverted one?" - she squints at him.

"Professional. Sex is said to be a great cure for depression. By demonstrating that he can be accepted even by a prude adult woman, it would encourage him to come out of his shell and realize that having contact with girls of his age range is not an impossibility." - the old doctor says knowledgeably.

"I am not a prude..." - she protests weakly. "But yes... what you said makes sense, doctor. I promised Greg I would do anything I could." - she reflects naively.

"It would help me so much, Miss Lana." - he says wiping his face. "If even a girl as pretty and as hot as you can accept my small dick, then there is hope in this world." - he smiles.

'Oh... right... he has a small peepee. That changes things... tiny penises don't count, they are risk-free, harmless. So, I'll not be doing anything bad, It's only to help him get over his insecurities.' - she rationalizes.

"Okay, I swore I would do anything. It can't be helped." - she accepts, still slightly reluctant.

"Truly? This is the nicest thing anyone has ever done for me!" - the boy says excitedly.

She sees his little weenie stirring awake. Lana gives him a warm smile.

The teacher once again grips 'Greg junior' and starts to slowly jerk it. It quickly grows to full mast in her latex-covered hands, his red penis head engorged and shiny.

"Not bad... the little guy is so hot and angry..." - she mutters softly.

Greg is softly moaning with pleasure, too engrossed in the experience to hear the teacher.

'Here I go again... why do I keep getting myself in these situations?... because I like it... no, I should stop this... but it's so hot... Lana, this is not for you... it's for Greg... yes, I'm wet, but this is for his well-being.' - she reflects while tugging his dick.

Lana starts to slide her hand rhythmically, as his teen wee-wee starts to throb and leak precum in her palm.

'Oh wow... I forgot they did that...' - she thinks, licking her lips.

The buxom teacher picks up the pace, moving her hand faster up and down the teen's hard rod.

His precum continues to dribble from his boyhood. The curvy and lascivious educator smears it along his shaft, using it as lubrication.

"Ahh... teacher... it feels so good..." - the chubby boys groans in delight.

Lana's coochie reacts with every stroke, twitching and begging to be touched.

She uses her other hand to palm her mound over her damp panties. A moan of pleasure escapes from her mouth.

"Uhh... randi..." - she hears the doctor murmuring.

Lana glances at the elderly man and notices his pants are down and he is furiously wanking his old penis, covered in white hair, which looks to be the same size as Greg's.

The sight is surprisingly enticing to the wife-to-be, who starts to move her hand around her slit, masturbating herself gently.

In lust, the teacher doubles down on her duties and pumps the young penis in front of her, while she strokes her pussy with her other hand.

Wet slick sounds echo lewdly through the tent, mixing with the three guttural moans.

The scent of pheromones makes the air heavy to breathe.

Probably due to her inexperience and ineptitude handling such an instrument, the teacher's stroking pace is all over the place, rapidly increasing with each moan.

"Lana... I am going to come... ahh... don't stop..." - the fat boy grunts.

"Yes... come for me Greg... come for your lewd teacher..." - she utters, rubbing her pussy.

Lana keeps jerking his hard slippery weenie, his intense moans signaling his incoming orgasm. She can feel his shaft pulsating and swelling, full of his young semen.

'Oh... yes... he's going to spray on me... so naughty... mmm... make that dick squirt Greg... let your dirty teacher make you come... yeeeessss... - she squeals with pleasure.

"Ahhhhh...." - he shouts as he ejaculates.

Greg's hot seed spurts in small white ropes over the teacher's glove-covered hand and lab coat. The cum looks lewd against her clothes, making Lana moan in ecstasy, her own climax rapidly approaching.

Mesmerized, she continues to pump the wiener, extracting every last drop. Her hand is a blur between her legs, ferociously rubbing her own damp snatch.

'So... much... semen... ahhh... so hot... mmmm... nggg... yess... I am so close...' - she thinks, barely able to form coherent sentences.

From her side, she notices the old man approaching her, still masturbating his aged, veiny prick.

"I am going to ejaculate on your tits, slut! Commmming..." - Dr. Hardik lets out a loud pleasure groan.

He points his penis towards her breasts, spraying his old sticky cum all over her gray tank top, square on where her boobs were. Some of it spills on her lab coat.

This was the tipping point for Lana.

"Nnnnnnnnnnnnggggggg..." - she yells loudly, having her own earth-shattering climax.

She feels her body buzz, her right hand burning with Greg's fresh teen seed and the old doctor semen ruining her blouse, the strong manly smell of cum invading her nostrils.

Nobody says anything for a bit, as they are all breathless and panting, recovering from their orgasms.

Lana gets up and looks down at the mess. Her soiled blouse was possibly ruined by the doctor's old cum and the right arm of her lab coat was covered by her student's young sticky goop.

The pervy elderly doc looks at her with a lecherous grin.

Suddenly, reality comes crashing back and she realizes that things went too far.

'No... this was too far... I let myself go... I am an embarrassment as a teacher, how can I ever face my students again? Ah, I better leave, now!' - she thinks in panic.

Seeing the terror in his teacher's face, Greg awakes from his trance.

"Sorry, Miss Lana... I.... ermm..." - he stammers, but it was too late.

Lana bolts away from the tent, her mind whirling with anxiety.

~~~

Continued below in Part B.

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

PART B

Detention titfuck, public selfie and drunk mistake.

~~~~~~~

Morning -- Shower

As Lana exits the tent, she sees Nurse Park relaxing on her phone near the gym wall. No other students are around.

The nurse's eyes widen as she sees the poor state of the newbie teacher.

"Hi, Lana. Oh, no... what happened?" - the Korean woman asks, concerned.

"Ahm... an accident..." - she says, glancing down at the mess, and joining her.

"I see. Let me help." - the nurse says, bringing out some tissues from her purse.

The teacher doesn't say anything and lets Vivian clean the semen off her right hand and arm. And helps Lana remove her soiled lab coat and gloves

"All done!" - she announces.

"Thanks..." - Lana says, panting.

"Well, you better hurry to the showers. We finished the exams." - she informs. "Everyone is just playing some sports now." - she points at the courts.

"Okay." - the teacher agrees weakly.

Lana starts to move, but Vivian holds her hand and hugs her. Lana reciprocates the embrace.

"You did a great job today, Lana. Don't be ashamed." - the nurse says.

"Really? I did not make a fool of myself?" - the teacher asks, feeling reassured by the warm words.

"Not at all, you are impressive." - the petite Asian woman affirms.

"Aw... thanks." - she blushes.

"Can we be friends? There aren't enough young willful women in town that are not already corrupted by this whole mess." - Vivian says, gesturing.

"I would love to be friends." - Lana smiles warmly.

"Great! So, I wanted to ask you a favor." - Viv says with big eyes.

"Anything for my new friend." - the teacher says ingenuously.

"Can you volunteer to help me at the senior/nursing home next week, please? We need all the help we can get." - she asks with pouting lips.

"Of course, Viv. I would be delighted." - Lana agrees, not thinking too hard about it.

"Okay, I'll give you my contact info and we can figure out the time." - she says squeezing Lana's left hand, avoiding the smelly one branded with cum.

"Deal! I should go now, bye Vivian!" - the teacher says hurriedly.

"It was great to meet you, Lana." - Nurse Park says. "Ah, also, next week, we'll be here again to post the results." - she waves goodbye.

Lana nods and quickly makes her way to the Locker Rooms, successfully avoiding her student's gazes.

Wow! Way to go, Lana! Don't be upset, Viv was right, I did good. I helped my students out so much with their issues.' - she praises herself as she walks into the room, ignoring the sign at the door.

~~~

The teacher removes her soiled clothes, wraps herself with a big white towel and grabs her shower accessories.

On the next section of lockers, she finds herself face to face with Kenny, the janitor. She yelps in surprise, calling his attention.

"Oh, hi Miss Cox, whatchu doin' here?" - he asks, astonished.

"I came to shower, what are you doing?" - she asks suspiciously.

"I'm cleaning, this Locker Room is closed." - he squints at her.

"It was not, I just came in." - she shrugs.

"Dagnabbit... lemme fix it. You should leave, miss." - the custodian complains.

"Wait! I need to shower, urgently." - she says determined.

"And I am to do my job, ma'am." - the young man says, holding the mop, unyielding.

"Please, can I just wash up really quick?" - she pleads.

Kenny can see a little bit of cleavage peeking from the top of the towel. Who is he to deny such a beautiful lady with big boobies, he thinks simply.

"A'ight, but don't tell anyone I let ya." - the tall man requests.

"Of course, thanks Kenny!" - she says grateful. "Ah... erm... I remembered something..." - she says, the events of this morning coming back to her.

"What is it, Miss Cox?" - the janitor asks.

"Well, you see... I posed for a photo this morning that Lilly, Jack's wife, said it was your idea." - the teacher tries to explain, embarrassed.

"Of your booty hole!?" - he exclaims enthusiastically.

"Shhh..." - she says looking around. "Yes... of my anus." - she admits red in the face.

"Are you gonna show me your asshole?" - he asks, blatantly adjusting his pants.

"Ermm..." - she glances at his bulge. "I promised I would."

"Cool, lemme see." - the tall custodian demands.

"It is in my locker, I will show you after I clean up." - she says.

"Deal! You can shower while I wait." - Kenny grins.

"Are you staying here?" - the teacher asks with wide eyes.

"'Course, I need to fix the door and finish cleaning, ma'am." - he says pointing to his supplies.

"Can you do it later, please? I will be embarrassed if you are here." - she asks.

"No can do. The girls need to use the room after gym class." - Kenny explains.

"But I am a girl and I need to use it now." - she protests.

"You're a teacher, miss, doesn't count. Why do ya need to use it so bad?" - he looks at her suspiciously.

"I cannot tell you." - she says, blushing.

"If ya won't say, I have to ask ya to leave, ma'am." - the custodian says stubbornly.

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