Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
D: "Cool, cool. Don't worry, babe. Just follow the Program, and everything is going to be fine."
L: "Why are you saying that?"
D: "I got an email from Mr. Winston-Phillips this morning, reminding me today is the start of it."
L: "Mayor Dick?"
D: "Yeah, I guess he is very interested in your performance for some reason."
L: "I guess... but about what you said... are you sure?"
D: "Yeah, embrace it. If we both get promoted, we can go for a weekend getaway or something."
L: "Oh, that will be nice."
D: "I will ask if there is anywhere cool around here to go."
L: "That sounds lovely. Thanks, Dens. You always calm me down."
D: "You're welcome, babe."
L: "Ah, you called me! Silly me, rambling about piffling things. Is everything okay?"
D: "I called to let you know that I'm at the clinic now. I'm next!"
L: "Hun! Good luck!"
D: "Thanks, babe. I just needed a boost of confidence. I'm a little nervous."
L: "Aww... everything will be all right, my Silly Carrot."
D: "I guess we both needed each other."
L: "*Giggles* True"
D: "Anyway, I better turn off my phone."
L: "OK! I love you, hun."
D: "Love you too, babe. Talk later."
L: "*Mwah!*"
++++
'Dens is right! I need to embrace it. It's what Bill and Dick expect. It's what Dens wants. It will be good for me and everyone.' - she thinks, getting out of her stall.
The steamy wife-to-be is feeling much better after chatting with her man. She glances in the mirror, admiring her beauty and sexy body.
"You can do this, Lana!" - she peps herself.
The buxom teacher walks to her supposedly empty classroom, Class 2-D.
~~~~~~~
Classroom
Lana enters her classroom and is face-to-face with Principal William Winston-Phillips.
"Hello, peach." - the big man says, towering over her.
The teacher gulps. She is always nervous in his presence, as he is an enormous man of both height and weight. His size clearly shows that he spent his glory years playing professional sports.
"H-hi, Bill." - she says, admiring the still impressive figure of the man in his late-60s. She inhales, trying to compose herself. "What can I do for you?"
"I just came to have a chat. I have four things to discuss." - he says, patting her butt.
"Uhh... I have detention soon." - she informs him, looking around nervously.
"Don't worry. I will be out of your hair promptly, buttercup." - Bill smiles, and he strolls to Lana's desk, taking a seat on her chair.
Awkwardly, Lana walks to the front row, and she is about to sit when the principal clears his throat.
"*Caham*. Over here." - the lecherous old man says, patting her desk.
Obediently, she hops on top of her desk. Her gray skirt rides up, exposing all of her thighs and the bottom of her white panties. She blushes and pulls it back down, covering about a third of her legs. With a smile, Bill places his hand on her exposed flesh.
"So, how can I help?" - she shyly asks her boss.
"Good girl." - Bill says patronizingly, squeezing her leg. She squirms with happiness. "First, I wanted to say that sending the email was a great initiative. Well done." - the principal says, and Lana is about to say it wasn't on purpose when he continues. "I will share it with the board." - he smiles.
"The photo?!" - the big-titted fiancee blurts, wide eyes.
"No, no." - he chuckles. "Your accomplishments and progress."
"Ah, I see." - she exhales, relieved.
"I don't want a photo to be the first time they see you. We will organize an event later on so you get to know them better. How does that sound?" - Bill says, caressing her supple thighs.
"I guess..." - the teacher agrees sheepishly.
"Excellent! I am elated, Lana." - the burly old man says.
"That is good?" - she says, unsure if she is doing enough to please her boss.
"It's fantastic. However, you still have some ways to go to reach Chloe in terms of progress." - Bill says seriously.
"Chloe?" - the bombshell brunette asks, feeling a pang of jealousy.
"Yes, she is doing really well. Beyond expectations. Not that you aren't. She is just excelling." - the principal reveals as he stops caressing her bare legs.
"I see..." - Lana says with mixed feelings. 'I should be proud of her, she is my student... but... why does she have to also be at some sort of Program simultaneously? I don't like it...'
"Although she doesn't have such a voluptuous body." - the sexagenarian says, eyeing Lana's curves.
Lana juts her tits out proudly. Bill cops a feel and nods his head approvingly.
"But it's hard to compete with an 18-year-old athlete. She's impossibly fit." - the principal analyzes.
"Hmph..." - the brunette educator mutters, jealous of her pupil. 'He knows I have a better body than Chloe, right? He needs to see it... and understand that I'm serious about the Program. I can't let my student leave me in the dust.' - she evaluates.
Lana unconsciously widens her legs. Pleasantly surprised and thinking the submissive teacher is inviting him to tease her some more, Bill places his old hand back on her thick thigh.
"Anyhow. For the second topic..." - the principal says, sliding his hand up her leg. "Pringle talked to me about some... let's say, less dignified... photos from the beach."
"Gee..." - she mutters, embarrassed. Bill starts massaging the inside of her thigh. "Mmm... that feels good..." - she moans.
"The man that took photos was trying to blackmail you and the school." - Bill says seriously.
"Oh, no! What happened to him and the photos?" - Lana asks worriedly.
"Don't worry. He has been taken care of." - Bill says cryptically. His words hang in the air menacingly.
Lana gulps. 'Goodness... I'm not sure what that means... maybe he means he paid the guy off? But... is Bill dangerous? No... he seems like a big teddy bear... right?' - she questions.
"Hmm... that is a relief..." - she says softly.
"There were also some friends of Pringle, correct?" - the husky principal says.
"Yes..." - she squeaks. 'Did something happen to them too?'
"Well, they won't bother you anymore. So you can rest easy." - Bill smiles. She cowers a little and feels chills down her spine.
"Oh, gosh. I hope it was not a bother, Bill." - Lana answers, holding her breath.
"Nonsense, doll. It's the least I can do for my most promising teacher." - the old principal says, still massaging her thighs. He pushes his hand against her legs, almost as if asking to open them more.
"Ah..." - the curvy fiancee blushes. "Thanks..." - she says shyly. 'Can't be. Bill is so nice. Maybe something else happened... better not to think about it. He's looking out for me.'
Lana opens her legs wider. Bill's hand slide up, stopping only an inch from her panties-covered cunt.
"Speaking of photos, this is a good segue into our third topic." - the massive man says. "About the Biology Supplement. I hired Pietro, the WinstonTV cameraman, to take the pictures. His skills are top-notch."
"Oh! I met him Saturday. He is Simon Romano's father." - Lana says, already having come to terms with the fact that her betrothed's new best friend will see her naked. 'At least he is a professional, and Jade trusts him greatly. Even Bill does.'
"That's correct, peach." - Bill says, happy to see her so willing.
"He seems like a solid choice." - she says, and Bill's finger starts playing with the edge of her panties. "Also, Roger mentioned to me that you asked him to be the male model?"
"That's right, you two will make a nice couple." - the burly principal says.
"Just for the photos!" - she says quickly, turning red.
"Of course." - he chuckles. "Although all the ladies like him. Do you, Lana?"
"Hmm... he is a bit too perverted for my taste." - the brunette teacher says. Bill's hand climbs higher, touching her panties-covered cooch. "Eeeppp..." - she yelps softly but says nothing else.
"That's not what I meant. Do you think he's handsome?" - the older man pries.
"I..." - she stammers nervously. 'Is it bad if I do? Roger is my colleague... I shouldn't say it... and I have Dens. Oh, come on, Lana. Is just a harmless question... it's not like I can't find other men attractive...' - she rationalizes.
"Come on, you can tell me." - Bill insists, rubbing her cooch and making the busty teacher moan.
"He is remarkably handsome." - she professes, squirming on Bill's skilled hand.
"And his body?" - the principal asks.
"It is great." - she says softly, trying to contain a moan. "I... admit Roger is a good choice for being the Biology model."
"Do you like him, sunshine? Tell me..." - Bill says, rubbing pussy in circles. She moans, enjoying the sexual massage.
"I do have a little crush on him..." - the future-wife confesses, unable to hold back.
"That's terrific. I am happy to know." - the old man says jolly.
"You are?" - she asks, a little out of breath due to the pussy-play.
"Of course, being more intimate with your colleagues is outstanding. Part of the Program." - Bill explains.
"Anngg..." - she moans. "That is true." - she says agreeably as the principal rubs her needy snatch. 'Gosh, this is so good... what Bill is saying makes sense... being close to other teachers should be fine... mmm... but a lot of things are part of the Program... hmm...'
"And it will make things easier for the shoot..." - he says, lining the bait.
"It... will?" - she asks breathlessly, falling into his trap.
"I guarantee. Since there is some chemistry and desire, things can be more natural. You're gonna be more relaxed than if it was a stranger or someone you didn't like." - the overweight man says like it is obvious. "The result will speak for itself."
"Oh... yes... that makes sense." - Lana concurs. Her pussy is drenched and in need of more attention.
"I know it does, doll." - Bill winks, knowing he should continue to tease the teacher a bit further.
"Mmm..." - she moans. The principal pulls his hand away, and Lana whimpers softly, immediately missing his big hand. He glances at the clock and nods. "Oh... I see... it is almost time for detention." - she says sadly.
"Indeed. As for the last topic, I had a good discussion with Mary yesterday, and she asked me to bring you this." - the principal says with suspense.
Bill pulls a plastic baggy with a small purple toy from his jacket pocket.
"Oh... what is..." - she asks, intrigued.
"It's a butt plug." - he says nonchalantly. She holds her breath. "Here..." - he says, extending it to her. As soon as she takes it, he resumes his coochie massage.
The voluptuous brunette takes the bag and examines the pleasure assistant closely as she enjoys her pussy being played with.
The toy is short and stubby, about 4 inches long and 1.2 inches in diameter. It has a thin tip but gets wider in the middle, with a notch and a flared base to hold it in place.
'Mmm... It looks interesting... similar to the ones Summer showed me. Ah... Almost the same size as Dens' peepee... although a bit thicker. It's so naughty... can this really go in my butt? Mmm... if I want to let Dens in... mmm... this seems like a good way to get used to... practice...' - she reflects, having trouble thinking clearly due to Bill's expert hand.
Bill notices her curiosity and grins widely.
"I am so proud of you." - the principal says, patting her head. She feels warm and fuzzy.
"You are?" - she beams at him, happy with her boss' praise.
"Tremendously, peach. This is a great start. I have a few others, so let me know if you need to up the size." - Bill says.
"Oh... I am not sure I will need it." - she says, slightly intimidated, analyzing the toy. 'Seems big enough...'
"Sure you will. This is a beginner's." - the hulking man states, pressing his hand firmly against her twat and rubbing it against the wet spot.
"Anggg.... it is?" - she asks after a high-pitched moan.
"Yes, once your asshole gets used to it, you need a thicker one." - Bill explains.
"Ahh... um-hum..." - the busty future-bride says, panting.
"Something closer to a real dick..." - the principal suggests.
"Only some..." - she mutters, thinking of all the cock's she has seen lately. Bill chuckles.
"That's right. Although you might be happy to know they don't get much longer." - he says.
"No?" - she questions, sounding a little disappointed.
"Nope. It's all about girth here. So it's okay to practice with smaller tools, as long as they are close to the real thing." - the old man hints while massaging her cooch.
'Hmm... so a real penis is still better... I see... so I need to build up to that... maybe try with some thicker ones or something... this cute toy will help me get used to it...' - she reflects, biting her lip.
"Promise me you will name it by tomorrow." - Bill interrupts her thoughts.
"Ah... okay..." - she agrees. "It is so I make a connection to it?" - she deduces.
"Correct, sunshine." - Bill says, flicking her clit. She moans intensely. "Do you have some lube at home? I forgot to bring mine to give you."
"I have it here!" - she says proudly, pulling out the bottle of lube from her purse.
"Oh?!" - the large principal exclaims, surprised.
"Vivian... I mean, Nurse Park gave it to me." - she explains. 'I don't want Bill to think I'm a lewd teacher that carries a bottle of lube in her purse... although... that's exactly what it is... gosh...'
"Excellent! Good call being prepared." - he compliments her, and she purrs happily.
Lana lifts the baggy with the purple butt plug as the bell rings. Bill craftily removes his hand from her cooch as the classroom door opens.
~~~~~~~
Detention
Two of her students walk into the room.
Benjamin Tan is a tanned southeast Asian boy with black hair and a big head. His family is from Singapore, and he is in love with his buxom teacher. His bad jokes, lack of awareness, and inability to contain himself constantly get him into trouble.
Wyatt Walters is Evie's boyfriend and a dark-skinned teen with bleached hair. He is usually the balanced voice in their friend group, although he also tends toward the mischievous side.
BJ stops in his track, staring at the toy. Lana gasps, noticing it.
"It is not what you think!" - their teacher blurts out, turning beet read.
On the other hand, Wyatt can't help but ogle at his teacher's exposed wet panties. The contour of her pussy is prominent, giving him an instant chub.
"It's not?" - BJ blurts out.
"I was just explaining to Lana how she can train her asshole for her fiancee." - Bill says. Lana gasps, turning even redder.
"Damn, lucky Dennis." - Wyatt says.
"Yeah... fuck..." - Benjamin agrees, adjusting his pants.
"I j-just..." - the teacher stammers awkwardly.
"Don't worry, peach. We're all adults here. It's normal to want to please your partner." - Bill assures her. She looks down shyly to avoid her students' eyes. "Speaking of pleasure.... Doll, why are Mr. Tan and Mr. Walters in detention?"
Lana notices that Wyatt is staring between her legs. She shuts them quickly and gets up from the table.
"Sorry, Bill, what was your question?" - she asks.
"Why are they in trouble?" - the old man asks point-blank.
"Just something Benjamin did yesterday." - Lana says, flushing slightly. 'I can't tell him... it's embarrassing.'
"Tell me." - Bill commands.
"Uhh... it is... erm..." - the teacher mumbles nervously.
"Go on." - the principal stares at her sternly.
Lana sighs, knowing she has no choice. Her face is fully crimson as she explains to the principal what has occurred.
"So he kept pushing the boundaries during the shoot. Nothing out of the ordinary for them..." - she glances at the boys playing dumb. "But at the very end, he touched my... coochie... with his... peen... and..."
"The what with who? Please explain properly." - Bill requests, deadpan.
"He poked my vagina with his penis!" - she blurts with her eyes closed. Her heart feels like it's going to leap out of her chest.
"That's no good." - the principal agrees, expressionless.
"Right?! After he was told to not touch me." - Lana says, relieved that Bill seems to agree.
"But, Miss Lana, it wasn't me. It was my dick." - BJ defends himself, pulling his half-hard prick out of his pants and wiggling it around.
"BJ! You stop that." - Lana gasps, unable to break eye contact with his sausage.
"It's okay, Lana. You did well. It's essential to enforce the rules." - Bill says, patting her ass. She sighs, happy to have her boss' support. "Mr. Tan, you are on thin ice, it's barely the start of the year, and you've been in detention multiple times." - the principal scolds him.
"Yes, principal, Sir principal." - BJ says, hurriedly putting his dick away. The boy is clearly scared of the burly old man.
"And why are you here, Mr. Walters?" - Bill inquires.
"I came to make sure BJ got here and protect Miss Lana. I'm her loyal knight until I redeem myself." - Wyatt explains.
Bill looks at Lana quizzically. She shakes her head as if to say, 'don't even ask'. Bill shrugs.
"Righto. Buttercup, I will stick around. I'm curious to see how you will discipline Mr. Tan." - the principal says, sitting back in her chair.
"Do you not have any appointments, Bill?" - the teacher asks. 'It would be better if Bill doesn't stay. I'm not sure what's going to happen with these two.'
"I'm sure Stella can take care of it." - the burly man states. "We can start, now." - he orders.
"Uhh..." - the teacher says, glancing at her students. "Boys, please go to your seats."
The pair of students apprehensively take their usual seats.
"Now, what is the plan?" - Bill asks impassively.
"I am just going to have Benjamin do some schoolwork. He is behind on some papers." - Lana says tentatively.
"Hey!" - BJ complains about being called out.
"You are, dummy." - Wyatt says, punching his friend softly on the arm. Lana can't help but giggle.
"That's not good enough. That's why Mr. Tan keeps transgressing. He will never repent like this." - the principal says with his booming voice.
"Ah..." - the teacher squeals. 'Why did I say that... I'm so silly... that's not good...'
"I expected more of you, Lana." - Bill reprimands her.
"I am so sorry..." - she whimpers, feeling lost and sad.
"Mr. Tan, what happened during the last detention? Did you learn anything?" - the heavy principal asks.
"I did. It was the toughest time of my life!" - BJ says dramatically.
"Oh? Do tell." - Bill demands, intrigued.
Lana shuffles anxiously, knowing what her student is about to recount to the principal.
Benjamin briefly explains what happened last time when Lana gave Jim a titjob out of frustration. Bill keeps an impassive face the whole time.
"She broke my heart! It was unbearable!" - the southeast Asian boy says exaggeratedly.
"Goodness, Lana. That's not great." - the gruff principal says, looking at the teacher.
The curvy wife-to-be puts her head down, ashamed of her past actions.
"Your first foray into detention was to make a student extremely upset. That's not how they learn." - Bill chastises her.
"What should I do?" - she asks, distressed.
"Well, you need to make up to him. We should always try to encourage them. That's what the Program is about." - her boss says, shaking his head.
"Gah..." - she squeaks.
"Well, what are you waiting for?" - Bill asks impatiently.
"Huh?" - the teacher asks, confused.
"Make it up to the boy." - the principal says, waving his hand at the tanned student.
