Naive Teacher in Winston Ch. 13b

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"It's a quiet place to study." - Greg mutters, turning red and looking down at his book.

"Oh! Your brother said you need some tutoring, right?" - Lana says.

"I do..." - the rotund boy mutters.

"I am free later this week." - the busty teacher says, putting her hand on his shoulder.

"How a-about fri... Friday... after s-school?" - Greg stutters.

"Sounds good. Tell Justin to message me." - she smiles, and he nods.

"Oooohh... Fatso needs some help at school!" - one of the class hooligans says. The other students snicker. Greg gives him the middle finger.

"Stop that!" - Lana reprimands the rowdy teen, who cowers.

"Why are you here, Miss C?" - Zack interrupts. He is of medium height and build, with a large head and a permanent smarmy smirk. He is the leader of the school bullies.

"Mary asked me to cover for her." - Lana explains briskly. She doesn't want to give him the light of day.

"Oh, so you are in charge of detention today?" - the bully smirks.

"I am." - the buxom teacher replies.

"Nice!" - Zack celebrates, hi-fiving his lackeys.

"Uhh... are you three also in detention?" - Lana asks Zack's underlings.

"Yeah, we told Mrs. H that if Zack is in detention, we all are." - one of them says. Lana couldn't recall his name for the life of her.

"It was some Spartacus shit!" - the other one comments.

"Language!" - she chastises. 'Who is that one again? Ugh. I should call him L1 and the others L2 and L3. L for Lackey. At least that will make it easier.' - she giggles in her head.

"Sorry, Miss C." - L1 says.

"*Sigh*... okay, take your seats, boys." - the teacher orders.

"What are we doing today?" - Zack asks.

"Just do some schoolwork for the next hour." - she says, seeing them exchanging glances. "No chit-chatting!" - she barks, and the boys recoil.

Lana puts her things on the teacher's table and sits on the chair, thinking of what to do next.

'Gee... way to go, Lana, you wanted to avoid Greg and Zack, and where are you now? Basically trapped with them.' - she laments.

'But maybe it won't be that bad. If anything happens, I need to stay in control, don't let them go too far.' - she considers.

'Besides, they all have tiny weenies, so this might be good practice for Dens, as Mary said.' - she reflects. 'Not that anything will happen.' - she adds quickly.

"Miss Lana?" - a voice to her left makes her jump in her seat.

"Huh?!" - the busty educator looks startled at the obese teen standing right there.

"Erm... since you are my girlfriend..." - Greg says. He has chosen this moment to show his teacher that he is also a 'real man'.

"School girlfriend." - she corrects him. 'I need to lay it on the line for him.'

"Uhh... right. Since we are a c-couple... c-can I get a 'hello kiss'?" - the fat boy asks. Zack and his underlings snicker. Greg turns beet red. "Pleeeease, Miss Lana?" - he pleads in a soft voice.

"Uh-huh..." - she says hesitantly. The other students chuckle at the teacher's clear lack of interest. Lana notices it. 'No, I need to step up this. I'm tired of Zack making fun of Greggy. Yes, he is pitiful, but that's not right.' - she evaluates. 'Help him, Lana.' - a voice, maybe Justin's, echoes in her head.

The busty teacher stands abruptly, determined to shut them up.

"What girlfriend will I be if I do not greet my boyfriend properly? Silly me." - she announces to Zack and the others with slack-jawed expressions.

Greg beams at her and makes a kissy face with his chubby lips. Since they are the same height, Lana steps forward and mashes her sexy rosy lips with his. The smooch lasts a bit longer than the teacher planned, but nothing unusual.

"Wow, thanks, Miss Lana. I mean, Lana." - Greg says with a stupid grin. He glances at Zack and gives him a cocky smirk.

"Bah, that's nothing. You're still a loser, fatso." - Zack says, clearly jealous. One of his lackeys, L2, whispers in his ear. "Hah, that's true! Everyone has been groping your girlfriend." - he scoffs.

"Yeah, I did it!" - L2 agrees. The other two nod.

"It's so lame letting her get kissed and touched by everyone." - the bully continues.

"It doesn't matter. She likes me!" - Greg says, seemingly unaffected by his snarky comments. He turns to the teacher. "Right, Miss Lana?"

"Mm-hmm." - the curvy educator agrees.

"Then she should give you a blowie or a fuck to prove you are her real boyfriend." - Zack states with a smirk. The other bullies agree.

"Zack Archer!" - Lana snaps, and the boy flinches. "Do not say these things."

"But it's true, Miss C. What kind of girlfriend lets other people kiss and grope her but don't fuck or suck her boyfriend." - the big-headed bully says. And she gasps.

"Language!" - she says. "But... those things are too far. I barely even do that with my fiancee. And no sex." - she admits. 'Ugh... why did I say that? Why do I feel the need to justify myself to this little bastard.'

"Woooooow!" - the bully says. "Must be so boring to be your boyfriend. They get nothing." - Zack mocks, and his friends snicker.

"Don't say that about Miss Lana! - Greg says, and the bully scoffs.

The round student growls at Zack, but the teacher holds him by his shoulder.

"My boyfriends at least get nice and steamy kisses..." - she says, turning to Greg and kissing him deeply. She invades the obese boy's mouth with her wanton tongue, and they make out sloppily. 'Why am I doing this? I guess I need to help Greg and prove Zack wrong.'

She breaks the kiss. All the boys feel their young penises stir at the lewd display.

"Meh. Miss C, does your boyfriend at least get to see you naked?" - Zack insists.

"Fiancee." - she corrects. "And sometimes... just recently..." - she says earnestly. 'Why did I say that?!' - she shouts in her head.

"Have you seen her naked, Greggy?" - the head bully says mockingly.

"No... maybe a little..." - the sad boy says. Even though he helped during the AV Club shoot, he barely saw anything as he was busy trying to hide his teacher from view.

"Greggy is a gentleman." - Lana defends and kisses him on his chubby cheek.

Zack and his underlings whisper among themselves.

"We have an idea!" - L1 announces.

"It's time to prove yourself, fatso." - L2 says.

"Show us you're not lame." - L3 chimes in. He rarely spoke.

"What is it?" - Greg asks, falling for their plan. He can't help but be curious about how to finally show them he is cool.

"Let's make a bet." - Zack proposes.

"No more bets!" - Lana says, but the boys ignore her.

"The winner gets to see under Miss Lana's skirt, no panties. You can finally see your girlfriend naked, fatass." - the Archer teen says.

Lana gasps.

"Absolutely not!" - she protests. 'I'm getting roped into these teen's shenanigans again... I can't let it happen...'

"What's the bet?" - Greg asks curiously. Lana groans.

"Whoever has the biggest dick wins." - Zack smirks.

"This is stupid. I do not agree to it." - the teacher says, flustered.

"DEAL!" - the obese student shouts, grinning. This is his chance to show he can be a real man and get rewarded with his teacher's sweet private parts.

"What the heck! Do not decide it for me." - Lana shouts.

"Man, your girlfriend is so lame!" - the bully says.

"So lame!" - L2 concurs.

"She can't even be naked in front of her boyfriend." - Zack insists.

"I bet she's not even his girlfriend!" - L1 chimes in.

"She is!" - Greg says. Lana nods.

"Being naked in front of your lover is one of the most reasonable things ever." - the Archer boy says.

"That is not up to you to decide!" - the teacher says, clearly upset. "It is between me and Greg."

"Isn't being naked totally reasonable?" - Zack smirks.

"Well, yes... but..." - Lana stammers. 'Maybe with Dens it is... where is he going with this?'

"I thought Bill said anything reasonable is valid to the Program." - the bully says. Derek, his brother, had told him the nasty rumors about a previous teacher in the same Program as Lana.

"*Gasp*! I...." - the future-wife says. 'What do I do? He has a point, but I can't just let them see me naked. If it was only Greg, maybe. But not Zack and his lackeys. They are driving me crazy!'

"Miss Lana, can I talk to you?" - the rotund student asks her, making puppy dog eyes.

"Ermm... yes." - she agrees, sitting down. "You four, quiet!" - she barks, trying to have some authority.

Zack and his friends discreetly fist-bump under the tables.

~~~

Size Bet

"What you want to talk to me about, Greggy?" - the teacher asks, looking up at her student.

"Please call me Big G." - the boy asks.

"Oh, I forgot. Yes, Big G." - she smiles.

"Help me prove Zack wrong. Please?" - the obese student begs.

"I want to help you, you know that. But this seems too much." - she says.

"I'm tired of them making fun of me." - Greg explains. Also, he wants to show her that he is a man.

"Hmm..." - she thinks, biting her lip.

"You said you owed me for helping in the AV Club event." - the fat teen says. He hates to use his ace, but he needs this now more than ever.

"Ah... I did... but I do not want Zack to see me naked..." - Lana says, torn.

"But I can't lose." - Greg says.

"Wait, what?" - she exclaims.

"The bet is about penis size. Who has the bigger dick?" - the fat boy asks cockily.

"Oh...." - Lana mutters. She knows Greg is larger since she has seen both pricks before. Although not by much, maybe an inch.

"Who is bigger, Miss Lana?" - he insists, squeezing her large melon.

"You are, Big G." - she says sheepishly.

"So it's impossible to lose. Help me." - the obese bastard smiles.

"I do owe you..." - she sighs. Greg nods.

'This is a terrible idea.' - she gulps. 'But he asked for my help and I promised a reward for yesterday... gosh.' - she reflects. 'Actually... is not that bad. I can teach Zack a lesson, and then I can probably get in private with Greggy and pretend I got naked for him. Then he can get some clout, as the kids say. It could be worse. And as he said... he can't lose.' - she chews over.

"All right... but then we are even. Also, you will not see me naked. We will go somewhere alone and only pretend." - Lana says seriously.

"I accept." - the round boy says, hopeful he can convince her otherwise once he wins. Maybe even get a handjob or something. He smiles and feels his wiener stir.

The pretend couple turns back to the bullies.

"You are on, Zack." - Greg says boastfully.

"Great, fatso." - the Archer teen says, standing up. Lana grumbles.

"Zack, you have to promise one thing." - the brunette teacher interjects.

"Anything for you, Miss C." - the bully smirks at her. He walks toward the teacher.

"Once you lose..." - she starts saying.

"If I lose." - Zack corrects her.

"Sure..." - she rolls her eyes. "If you lose, you will leave Greggy..." - the obese boy clears his throat. "I mean... you will leave Big G alone. No more bullying." - she says sternly.

For a second, the youngest Archer almost falters. He takes a deep breath. The bully knows this is a gamble, but if it works, things might escalate and open new doors with the hot teacher. Zack can't wait to tell his big bro Derek if his plan succeeds. His brother will certainly be proud, right?

Zack stands on the teacher's right side, opposite Greg. He smirks at the fat student and gropes Lana's left breast. She lets out a surprised moan.

"Deal." - the bully says with conviction.

"Dude!" - L1 exclaims.

"Woah!" - L2 shouts while L3 puts his hands on his head.

Zack turns to his underlings and gives them a thumbs up.

"We need to do this properly..." - the Archer boy smirks.

The two students stand in front of the class with their backs on the whiteboard. They position the teacher's chair before them, less than two feet away.

"Let us get this over with. Ready?" - the busty teacher asks. They nod. "Pants and undies down."

Greg and Zack pull their bottoms down, exposing their soft little guys to their teacher.

'So cute...' - she thinks, admiring the 2-inches of penis on each student. The obese boy is slightly larger and thicker than his bully, but not by much.

"Big G is clearly larger. He wins." - Lana declares.

"Don't count your chickens. We're still soft." - Zack says, leaning forward and grabbing the teacher's left tit. She moans with surprise, and the bully's weenie stirs and grows.

'I shouldn't let him do that... but it won't change anything... Greggy is still an inch bigger when hard.' - she reflects, letting the Archer boy molest her boobie.

Zack uses his other hand to play with his quickly hardening peen. In mere seconds, he is fully erect. Oh, to be young.

"See, I'm bigger now." - the bully says, pushing his hips forward and emphasizing his 4.5-inch weenie to the curvy teacher.

"You call that big? You should be ashamed of it." - the future-wife replies without thinking.

"Uhhh..." - Zack mumbles, surprised at her reaction.

"It is like a puny little worm." - Lana wiggles her pinky finger. "Pathetic. There's no way you can make any girl happy with your 4-inch wee-wee." - the fiancee jeers.

The hooligan stares wide-eyed at the busty teacher. Greg chuckles, happy to see his bully get his comeuppance.

'Look at his face! Hah! That's what he gets. Trying to harass my boyfriend... I mean, my student... and me. What was he thinking? His weenie is so small, even hard.' - she smiles.

Something clicks in her brain.

'Oh.... Dennis is the same size as Zack... I... Uhh.... No... no... I love Dens' peepee... this is different. Right? Yeah! I'm just trying to make Zack feel bad for all he did to Greggy. Dens' small peepee doesn't bother me.... Not at all. Dens is more than enough for me.' - she tells herself.

Zack blushes and almost falters again, being mocked by the sexy woman. Somehow, his boner remains strong. Oh, to be young.

"That may be..." - the bully stammers. "But I'm still winning!"

The teacher glances at Greg's soft hotdog and gasps. In Zack's aroused state, the bully is about an inch bigger.

"Gee..." - she mutters.

"Way to go, boss!" - L1 cheers.

"Wait! I can still get hard." - Greg says, tugging at his little guy.

Silence falls onto the classroom, everyone staring at the fat teen playing with his wimpy penis. He keeps looking around, intimidated by all the stares. His eyes widen, and he ferociously pulls his wiener to make it hard. Unsuccessfully.

"Big G, just make it erect. For me." - the teacher urges.

"I... uhh... can't... it's not working..." - the obese student says, starting to panic.

"Pfff... look at fatso. Can't even get hard!" - Zack mocks, swinging his boner around.

Unconsciously, Lana lightly slaps the boy's wiener.

"Stop it!" - she shouts at the bully.

"Woah! Miss C touched boss' D!" - L2 cheers

"I did not... It was..." - the curvy fiance stammers.

"She did! I saw it!" - L1 says.

"The slut loves dick." - Zack smirks.

"I do not... you were just harassing poor Greggy!" - she tries to justify.

"There's nothing in the rules to say that's not allowed." - the bully points out.

"But..." - she mumbles. She stares at Greg, still trying to erect his soft peepee. His eyes are watery. 'What can I do? Hmm... Ah! Zack got hard really quick, touching my large breasts...' - she considers.

"I guess I win then." - Zack declares with a wide grin.

"Not yet." - she sighs. "Big G, please grab my breast. My tit." - she says, opening her blouse and pulling her right boob out.

Nodding, the pitiful student stretches his chubby hand and grips the teacher's bare breast.

"Nice tit, Miss C. You should show us the other." - Zack smirks.

The teacher ignores him and looks deeply into Greg's teary eyes.

"Go on, Greggy... touch your girlfriend's slutty tit..." - she whispers, trying to egg him on. He gulps.

For a second, nobody says anything, and Lana sees the blubbery student's weenie stir.

"You're so lame, Fatso!" - Zack mocks.

"So lame!" - L2 agrees.

"Blubberboy!" - L1 chimes in. L3 nods.

"Can't even get hard when you have your girlfriend's boobie in your hands. You're a poor excuse of a man!" - the head bully laughs. The others join in.

The erection that was forming between Greg's legs shrivels immediately.

'Darn.... Zack will not make this easy on poor Greggy... what can I do.... Ugh... I don't want to get naked for him...' - she ponders.

"Help me, Miss Lana..." - the obese student pleads with tears rolling down his chubby cheek.

"What can I do to make you hard?" - she asks bluntly.

"Please... lick my wiener...." - Greg sobs pitifully.

Lana inhales, taken aback.

'This is a bad idea... I don't know if it's the proper way... hmmm...'

'No! Stop it.'

'Remember what Mary said. Stop doubting yourself. Dens already said I could do what I did with him at the start of our relationship. And it will help Greg! It's my responsibility with the Program. I also need to practice for Dens with smaller penises.'

'This is just how it is. I need to change my mentality and embrace things... uhhhh...'

'Easier said than done, but maybe I'll get there. Deep breaths. You got this, Lana.'

Exhaling, the teacher grasps Greg's peepee. The boy moans softly.

'I'm doing this for you, Dens.' - she thinks lovingly.

She leans forward and kisses it, inhaling his masculine smell combined with soap and sweat.

"Fuck me, Miss C!" - Zack says, impressed.

Smiling, she plants lots of small kisses on the fat student's weenie. No reaction. She looks up, and Greg is looking at his classmates.

"Focus on me, Big G..." - Lana purrs to get him aroused.

The wife-to-be begins licking his shaft. She laps all over it, even licking his small-ish nutsack. He groans softly, and taking that as a good sign, she licks his dickhead enthusiastically.

She hears some snickering from the other boys.

"Fatso is a sissy!" - Zack mocks.

"He's going to be a virgin forever!" - L1 comments.

"Such a soy boy." - Zack agrees.

"I bet he would love to get pegged..." - L2 laughs.

Again, any progress made by the teacher is immediately undone. Greg's eyes tear up again, and his little guy shrinks to nothingness.

Lana sighs. 'This is more difficult than I thought... maybe Greggy is like Dens... he doesn't think I'm good enough... do I need to get better to arouse Greg? No... it's probably because of these hooligans... I need to try more things...' - she thinks, determined.

"Do not pay attention to these idiots. Your girlfriend will take care of your nice cock today...." - she coos sultrily. Just the sentence alone awakens his peepee again.

'Ugh... I hated saying that...' - she winces.

The wife-to-be takes a deep breath and wraps her mouth around the fat student's tiny weenie. Greg groans approvingly.

'Oh, he is growing... I can do this....' - she evaluates, using her tongue to lick the dickhead inside her mouth.

At the same time, she hears some jeering and mocking from the bullies, and Greg's member immediately shrivels.

'It's like putting a wet noodle into your mouth... like a squishy gummy worm... I wish Greg's penis was bigger... we could have fun... mmm... wait! What am I even thinking? Ugh. His size is decent, like Dens' peepee. Darn it... focus Lana...' - she thinks, closing her eye and bobbing up and down his shaft.

To her surprise, she manages to take him entirely inside her mouth. She smiles, proud, even though he is still mostly soft.

'Yes, it's not even 4 inches... but it's progress...' - she tells herself happily.

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