Naive Teacher in Winston Ch. 10

"Showing them my underwear, on purpose?" - the future-wife asks, flushing.

Lana could feel her rosy nipples hardening at the prospect.

"Correct. Or you could pretend it was an accident. Let's test it, flash me your panties, now." - he orders.

She gasps softly, partly shocked, but partly aroused at the command.

"If I must..." - she says submissively.

She takes a hold of the hem of her skirt and pulls it up, until the bottom of her underwear becomes visible. She then opens her legs wide, giving him a good view of her white cotton undergarments.

The teacher's cooch twitches lewdly, sending shivers through her body.

"Good job, doll. You can stay like that for a bit." - he says with a lecherous smile. She releases her skirt, leaving her legs spread wide. "You should encourage the students to flip your skirt, boys love that." - the old man continues.

"Oh, my... and how about kissing?" - she asks.

The wife-to-be secretly wanted his boss to encourage her to keep kissing her students.

"Yes, kissing is expected. If they are doing well, even a french kiss is appropriate. The more tongue and saliva, the better." - he explains, and she nods enthusiastically.

She blushes again at the stimulating conversation. Her hands drift to her panty-covered vagina and she touches it softly.

"And exposing my body like this is not bad?" - she asks, already knowing the answer.

"Not at all, it will all be part of the 'Incentive Program'. You should bare even more!" - he states, and she squeaks, a mixture of a gasp and a moan. "What else you got?" - he asks.

"Erm... the students seem to like it if I touch them. Is that not wrong?" - she asks nervously, but her hand was slowly caressing her needy pussy.

The principal lets out a loud laugh.

"Not at all, doll. That just seems reasonable to me." - he says approvingly. "From now on, you have carte blanche to do as you please." - the old man gives her a naughty smile.

"Really, anything at all?" - she asks, her thoughts all over the place.

"Anything at all. As long as the progress continues and you respect the basic rules, like the uniform... and some others." - he explains, whispering that last part.

"That seems reasonable." - she says agreeably. She was truly excited for the future.

"Do you agree to take part in the 'Incentive Program'?" - Bill asks, with a serious tone.

'Oh, gosh... this may get out of hand. No. Don't worry, Lana. This is for yours and Dens' future. And for your students' future. You need to do it.' - she tells herself.

"Yes, I would love to be part of it!" - the naive fiancee agrees.

"Great. I have the papers to sign on my desk. After that we can try on the new uniforms." - he says, standing up.

The meek teacher looks up again, impressed at how tall and large he was.

"Thanks, Bill, for giving me this opportunity." - she squeaks, a mixture of nervous, thrilled and aroused.

"My pleasure, buttercup." - he says, giving her a wide smile.

Bill points toward his desk. Lana closes her legs and slowly gets up.

She walks past the principal, and he gives her a slap on the butt.

"Atta girl!" - he says. "You are making us all proud."

She can feel her ego swelling by his praise. She can also feel the sting of his hand on her bum.

'Hmm... I kinda like it... imagine how would his slap feel on my bare bum... no... stop it...' - she chastises herself, but her sex was throbbing with desire.

"Thanks, Bill." - she says earnestly.

They go over to his desk, and he gets some papers out of a drawer and lays them out for her.

The top says 'Winston-Phillips School -- Incentive Program'.

"Sign here." - he orders, pointing at the line at the bottom.

Something on the back of her mind says she should be prudent and read the contract first. She dismisses it as an unfounded concern.

'Bill would not do anything bad. I need to show that I trust him.' - she decides.

She starts to skim it, but the old pervert starts groping her ass cheek, underneath her dress. He kneads her panty-clad assflesh with zest.

The lewd action distracts her from reading, and she is now only paying attention to one thing.

The teacher arches her back, proudly emphasizing her behind to her superior. He lifts her skirt with his other hand.

"Saw it already, a bit too boring." - he says disapprovingly.

"Ah, Bill, that is embarrassing." - she says, wiggling her bum

"No need to be shy, this is all part of the program now." - he explains with a horny voice.

"You said my panties were boring?" - she asks, looking at him.

"Not something a beautiful young woman should wear." - the old pervert states.

"But these are the only types I have!" - she explains.

"Do not fret, the 'Program' will provide you with some new ones." - he explains. Before she can say anything else, he continues. "Now, sign."

Lana obediently signs the contract.

"Very good, come give this old fart a celebratory kiss." - he says, opening his arms.

They embrace and kiss. Bill starts to grope both of her ass cheeks underneath her panties.

To her frustration, he quickly breaks the kiss. She groans.

"We can easily get carried away. We have things to do." - he says in response. She nods.

He opens one of the cabinets and grabs a sizable bag. He guides the busty teacher back to the couches.

"Are you ready for your new wardrobe?" - the kinky principal asks.

She nods anxiously, her breasts bouncing due to her accelerated breathing.

He lays the clothing out on the middle couch.

Lana can see a few skirts, a few shirts and some panties.

"That is all? Where are the bras?" - she asks naively.

"Well, there are no bras. We suggest you go braless with some of these outfits. Of course, it's up to you, but it's highly encouraged by the 'Program'." - he explains.

"Ermm... I see...." - she stammers, not knowing what to do.

Sensing her discomfort, Bill starts showing off the new outfits to distract her from the worries.

In total there are 6 skirts, 2 of each color between red, white and gray. They also vary in length, with 3 of them being on the longer side if compared to the other 3. However, the longer ones are more flowy, while the shorter ones are tighter.

There are also 6 blouses, again, 2 of each color. They are all sleeveless. The 3 opaque ones have a v-neck, hopefully leaving a good amount of cleavage. While the 3 sheer blouses button up all the way to the neck.

"Do you like them?" - he asks with a grin, and she nods shyly.

'Some of these are too daring. Maybe I can avoid the sheer blouses and the shorter skirts.' - she reflects.

As if hearing her thoughts, Bill interjects.

"Feel free to use any combination you want, but you cannot repeat one until you wore all six." - the old lecher states with a grin.

"What? But..." - she protests, terror stamped across her face. 'Oh, no!' - she panics.

"It's in the contract you just signed." - he explains with a raised eyebrow. "I thought you were reading it." - he reprimands her.

"I got distracted by your groping..." - she justifies, nervously.

"Don't blame me, Missy. It's your fault for not reading it thoroughly." - he says with a wrinkly frown.

"Sorry, Bill. I did not mean to accuse you." - the teacher explains. 'Gosh, I should not have said that.' - she thinks worriedly.

"It's all right." - he says, putting his hand on her hips. She lets out a sigh of relief. "Also, no need to be worried, it's part of the 'Program'. Wearing the uniforms will benefit everyone." - he says merrily.

"You are right, sorry, it is just... I never wore anything like that. Not sure Dennis will approve." - she admits bashfully.

"Of course, he will. My brother will have a talk with him." - Bill says with a devilish grin.

"Thank you so much, Bill. It's good to have someone looking out for me." - the gullible teacher says, happy that the principal was helping her grow so much.

"It's my pleasure, peach. Also, you're obligated to wear the skirts, blouses and panties provided, the rest is up to you." - he explains.

"Okay, and how does the underwear look?" - the future-wife asks, concerned.

He lays the panties out on the couch.

There are also 6 pairs, red, white and black instead of gray. There are 2 cheeky-style, covering less than half her cheeks, 2 also cheeky-cut but lacy and quite sheer, and 2 thongs.

"*Gasp*... are you sure I have to?" - she asks, looking him in the eyes. He nods with a serious look. "Since I... hmm... never wore this type of... ensemble... erm... I... do not think it would look good on me." - she admits, chagrined.

"Don't be daft, your body is perfect. You have beautiful curves. You should be proud." - he assures her, running his hand through his white hair.

"You are not just saying that? You mean it?" - she asks with demure.

Lana knew she had a good body, she just needed to hear it from others once in a while.

The voluptuous fiancee was unconsciously getting addicted to compliments, even more so if they were somewhat crass.

"I would put money on it." - he grins. "Anyone in town would give their fortune to spend a night with you and your body." - the principal affirms hornily, taking the bait.

"Aw, thanks." - she blushes and her cooch twitches at the idea of sex. "Are you certain about the outfits?"

"They'll look great. How about we try a few of them on?" - he says lecherously.

"Right now?" - the wife-to-be asks, taken aback by the proposition.

"We need to make sure the size works. This is what this time is for." - the old principal says casually.

"I guess so. Let me go to the Staff bathroom and I will be right back." - the teacher says naively.

"No. Right here." - the husky man demands.

"Eh?" - she exclaims, her eyes almost popping out of their sockets.

"No need to go anywhere, Chloe and Mary changed right here." - he says as if it was the norm.

"They did??" - she blurts out.

'If they trust him, I suppose I should too... Bill seems like a harmless old man... although he is quite big... hihihi...' - she giggles in her head.

"Okay, Principal Bill." - she mutters timidly.

"Perfect. Give me a minute, buttercup. I just need to make a quick call." - he states, and she nods sheepishly.

~~~

He walks to his desk and plops down on his fancy expensive chair.

Bill knew he could push the teacher even further if he was alone, but this was not the goal here. The goal was to break her down and make her experience some more embarrassing situations.

He shouldn't forget that this was a long-term plan. He could wait longer to have her.

He picks up his phone and dials.

~~~

Lana sits down. Her mind is whirling, too distracted to notice what the principal was scheming.

'Gosh, gosh, gosh... I will have to change in front of him... courage, Lana. This is normal. Mary and Chloe did it too. Besides, I am wearing underwear, so it's not much different than a bikini. And I am going to wear a two-piece tomorrow on a public beach. Jeez. What am I getting myself into.

Her breathing quickens.

'Hopefully this "Incentive Program" is beneficial to everyone, including me and Dens. I'll have to talk to him tonight, I hope he gets on board. I need his support. Focus, Lana, you have a pressing matter at hand'.

She takes a deep breath, trying to concentrate.

'Let's try these uniforms to know what to expect next week. Gosh... with luck they won't be too revealing, since the whole school will see me wearing them... wait... the whole town! Hmm... I'm nervous. My stomach is in knots. It's weird being both anxious and aroused at the same time... no... I'm not aroused, it's just a normal body reaction. Focus...'

The principal clears his raspy old throat.

Lana jumps and shrieks, not realizing that the beefy man was standing next to her.

"Oh, I didn't mean to scare you, doll." - he says with a fond smile. "You can start undressing now." - he adds, his kind smile changing to a perverted one in a flash.

Awkwardly she starts to unbutton her blouse. Her body starts to grow hot.

The burly elder principal sits on the couch, and crosses his legs, admiring the show.

She blushes furiously, feeling even more self-conscious.

Lana removes her blouse, exposing her enormous bra-encased breasts to the depraved man.

"*pheeeeew*" - he whistles in appreciation. "Amazing."

She blushes even further, and she can feel her nipples hardening. A fact that doesn't go unnoticed by Bill.

Closing her eyes and holding her breath, she pulls her skirt down, letting it bunch around her ankles.

"Your booty is so plump and round. It should be a sculpture." - he says with a naughty grin.

"Erm... thanks, Bill." - she says, abashed but aroused.

Suddenly, the door opens.

~~~

Professor Henry rapidly walks in and closes the door behind him.

The professor was an older scrawny man, about the same age as the principal. He has a mousey look and feel to him, being short, small and white-haired.

The naive teacher turns around at the sound. Her massive mountains of flesh bouncing wildly.

"Eeeeekkkk!" - Lana yelps. "Why is he here?"

She bends over in place, trying to cover her private parts.

"I invited him, he helped me judge Chloe's outfits yesterday. It makes sense to get his help." - Bill states as if it was obvious.

"He can't! I barely know him!" - the panicked teacher complains.

"Nonsense. Don't be a prude, dear. Professor Henry here is one of your most devout supporters with the board." - the old principal states.

"He is?" - she asks wide-eyed. "You are?" - the newbie educator inquires to the visitor.

"That's right, sugar. We haven't interacted much so far, but I see you're doing a marvelous job. This school needed a shake up and you were a godsend." - the mousey old professor says.

During Chloe's event, Professor Henry was very nervous, as he was caught by surprise. This time however, Bill had filled him in on the situation and he had been readying himself all day.

"Oh, thanks." - she says, blushing. Lana was still covering her boobs and crotch.

"Come on, old friend. Sit, sit." - Bill ushers, pointing to the seat next to him.

The scrawny teacher sits and makes himself comfortable on the couch.

"You can go ahead and remove your hands now." - the overweight principal states.

"Erm... does he have to stay while I change?" - she asks, uncomfortable.

"Of course. It's too late now to do anything else. You can change in front of us. Do you mind, Henry?" - the husky man asks with a grin.

"Not at all, Bill. It will be my pleasure to help." - the senior professor says with a horny voice.

"Gah... but..." - the teacher stammers, slightly nervous. 'You must do this, Lana. Don't be nervous. This old decrepit teacher is harmless. I reckon Dens would laugh at the situation.' - she considers.

"So? We don't have all day, sunshine." - the principal says impatiently.

"Ah... okay." - she agrees reluctantly. "I do not need to try the panties on, right?" - she asks, optimistically.

"What should we do here, old friend?" - Bill asks the bony elderly teacher.

"We should have compassion and let her skip that part." - Henry says, winking at Lana.

"Very well. I guess we can do her that favor." - the old principal says.

Unbeknownst to Lana, they had already agreed on this course of action beforehand. They wanted her to feel that they were being benevolent to her.

"Phew... thanks." - she says relieved.

She drops her hands down and straightens up, showcasing her body to the lecherous professor.

"Wowzah!" - the mousey white-haired man exclaims. "What enormous melons!"

The young teacher blushes and unconsciously bounces a little, making her heavy boobs jiggle. Their eyes go wide.

The naughty fiancee can see a little protuberance forming on Harry's slacks. Bill still has his legs crossed, hiding his straining erection.

"Thanks... I will try some outfits on now..." - she says bashfully.

She tries different blouses and skirts combinations.

~~~

Author's note: I will skip the lengthy description of Lana trying each outfit and the men's reactions to it and will summarize how each piece looks on her curvaceous body.

The three v-neck button up blouses fit the teacher nicely, stretching tightly across her advantaged chest. The buttons look strained, almost as if they could pop at a minute's notice. The cleavage the blouses provide is modest, yet enough to be tantalizing, as the last button doesn't go all the way up, ending around the top of her mighty orbs. Her bare arms help completely the look, adding some more bare skin and allure.

It would be a somewhat normal blouse for a hot day out or a casual dinner, but definitely too much for a teacher to wear to school.

The partially-sheer collared-blouses are a bit more daring. Maybe too daring. These blouses are a looser fit than the others, not emphasizing her bosom as well. And although the buttons go all the up to her neck, her bra is obviously visible underneath, as well as her flat tummy. Lana has not even realized that the sunlight might make these tops become practically see-through. So, in a way, the lack of shape of the blouses is compensated by the insurmountable amount of barely covered skin. Her arms are also bare.

If the other blouses would be considered too much, these are definitely beyond the scope of what could be considered acceptable. But it was part of the 'Program', so Lana could not complain.

She decides to leave the sheer blouses for last.

The first three skirts are longer, but unquestionably shorter than anything that the teacher was used to. They only came about mid-thigh, leaving the rest of her creamy legs bare. They accentuated her big ass nicely, but nothing too obscene. The skirts were also loose and flowy, being overly easy to be displaced, as it was evident by when Lana did a spin, and her white panties came into view.

Overall, these were nothing much, maybe a tad short for a school environment. However, they would provide the students with lots of opportunity for pranks, and Lana with easy ways of flashing them her new underwear.

The other skirts were almost too much for our innocent teacher to bear. They came only about a palm below her phat white ass, leaving an indecent amount of bare thigh flesh. These skirts were also tight, shaping her massive posterior nicely and stretching tight across her cheeks. The skirts would be harder to lift than the others, but once it happened, the teacher would have a hard time pulling them back down over her shapely butt.

These skirts looked almost pornographic on the sexy teacher, with her big ass on full display. They were more appropriate to be worn by a stripper going to a dance club.

The combination of the tight, short skirt plus the sheer blouse, would decidedly cause a stir among the townsfolk, and a rise on all the teen penises at the school.

~~~

As Lana finishes trying the last of the outfits, a sheer red blouse with a flowy gray skirt, Bill finally stops her.

"Lana, doll, your bra looks terrible with this blouse. The white contrasts too much. How about you remove your bra so we can see it properly." - he orders, not giving her room to question.

"*gasp*! Prof. Henry would be able to see my breasts in this blouse! It would be inappropriate!" - the teacher protests.

"What do you think, old chap?" - the principal asks.

"I guess she's right, going braless with this blouse would be quite raunchy." - the scrawny professor says.

"Thank you!" - she says, thankful for his cooperation.

"That's true. Very well, Lana, please remove your bra and try the opaque red one." - the elder principal states nonchalantly.

"What? But..." - she stammers.