Naive Teacher in Winston Ch. 09

Trying to not mull over the events any further, she makes her way back to her stuff at the printing computer.

As she walks by, the library patrons look at her with knowing smirks.

~~~

She arrives back at her station. It feels like it was hours ago that she was there to print her photo, a lot of stuff happened in a short period of time.

Her mind was still a jumbled mess of thoughts.

'Forget about everything for now... let's just print Kenny's photo and go home.' - she decides.

Lana surreptitiously prints the photo of her displaying her butthole happily.

She grabs her stuff and scurries out of the library, trying to avoid people's glances.

The teacher spots the janitor's tools outside the Staff Room.

She enters the room and runs into Kenny, stumbling back against the force of the impact.

"Eeekk!" - she yelps in surprise.

The custodian, by reflex of course, grabs and holds the teacher by her ass, preventing her fall.

"Erm, thanks Kenny." - she says, embarrassed.

"You're welcome, Miss." - he smiles wide, still gripping her ass.

Lana was secretly enjoying being manhandled by this tall man, feeling like a small delicate lady in his long arms. He was over a foot taller than her.

'Don't get carried away...' - she thinks. "You can let me go now." - she says sheepishly.

"My pleasure." - he releases her from his grasp. "How can I help ma'am?"

"Kenny, I came here to give you the picture." - she states.

Professor Henry was still in the room and perks up, hearing the voice of the curvy educator.

"What picture?" - the custodian asks seriously.

"The picture of my anus." - she says, turning red. 'Why am I saying this out loud? What's wrong with me?' - she shakes her head.

"Ah, 'course! Where is it?" - he asks excitedly.

"Here." - she says, taking it out of her purse and handing it the photo to him.

He whistles out loud, impressed. It was even better than when he saw it on her phone.

"What a perfect butthole..." - he comments, adjusting the bulge in his pants.

"Thanks." - Lana replies timidly.

"Can I have one too?" - Prof. Henry asks, coming over to them.

"No! This is for Kenny only." - she tells the old man.

"Ah, shame. Can I see it, youngster?" - the lecherous elderly asks the custodian.

"Yes, sir." - the janitor says, showing him the photo.

Lana gasps, not expecting this development. She was blushing furiously.

"Wowza. Nice buttocks. Maybe next time we can see that fanny." - the pervy professor beams at her.

"Erm... well... maybe... I should go...." - she says, trembling. She turns and bolts from the room.

"Thanks, Miss Lana! It's amazing!" - Kenny shouts as she leaves.

"Can I make a copy..." - she overhears the old man ask the janitor as the door closes behind her.

'Ugh, of course that depraved Professor Henry saw my anus... another one to the list of people who have seen it before Dens. Argh. I will have to talk to the old man tomorrow and explain the situation somehow.' - she considers, trying to come up with an excuse.

Prepared for a night of chores, she makes her way to her residence.

~~~~~~~

Musings

During her walk home, her mind races about the events of the day...

Dens' coworkers suggested she send a Daily Selfie to her fiancee, and of course, they would help her judge the photos beforehand, to 'ensure' quality. It was normal to ask for a second opinion after all.

She finally managed to pay the bet with Jack and Lilly, although she wasn't happy about letting them take a picture of her bare butt and anus. She even let Lilly poke her tight hole and let Jack Sr. get naked and pose with his big thick penis next to it. Glad he stopped before putting his dick inside her asshole.

'Phew, that was close. I'm not ready yet to lose my anal virginity...' - she thinks.

Then Nurse Park examined her in front of all the students. She touched her breasts, her cooch and her anus. Argh. At least Vivian was nice about it.

Oh, and the students saw my naked butt, public hair and a bit of my cooch... all before my future-husband! Thankfully it was an accident, so it didn't count.

Well, but the doctoring fingering her did count. He saw her naked and penetrated her with his finger.

'I was going to skip the fingering in the "get even" list... but at least now I am truly even with Dennis in this regard.' - she shrugs her worries away.

'Glad my brave students stopped that greasy old man from ruining me any further, but it's a shame that it backfired.' - she reminisces.

She did end up touching the penis of every male student in the school. And even made some of them hard on purpose.

'All my pupils had big thick peckers, except for Andrew. All bigger than Dens. Well, at least the other half of them were tiny, and small peepees don't count.'

The teacher lewdly kissed Jim's penis and encouraged both Herb and Greg to get hard for her. Speaking of Greg, she ended up jerking him off and making him come all over her gloved hand.

'But he was tiny, so Dens won't mind.'

Of course, the slimy old doctor sprayed his elderly cum all over her gym shirt, ruining it. Hopefully it will be clean to use next week.

At least she met Vivian, who was really nice. Lana even agreed to help her new friend out in the nursing home at some point in the future.

Who could forget letting Kenny spy on her naked during her shower and showing him the asshole picture from that morning. Ugh, what was wrong with her.

'Shame that Mary was late for lunch, I wonder what she was up to with Bill.'

Lana was now in possession of the large blue dildo to 'practice' for the school play. I guess she should show it to Dennis, to ease his worries.

All the posters from the AV Club scattered throughout school were thrilling. Her students even molested her in the corridors and asked her lewd questions. My, my!

Detention was even more intense, with the TTT trio driving her crazy.

'Ah, I'll apologize to them tomorrow, I got exceedingly angry at them.'

The frustration led to giving Jim a titty fuck, all in an attempt to shut BJ up. In the end he came all over her breasts and inside her mouth.

'Phew, I am finally even. Hopefully Dens will be happy that I let another man squirt in my mouth. Although Dens semen tastes way better... maybe I need to sample some more to compare.'

The lewd teacher skipped around braless and made out with Principal Bill in front of some students.

She then removed her panties in public and sent a dirty pic to her fiancee and his colleagues. Of course, the guys were just helping her take a good pic.

For him to keep her secret, she decided to rehearse the play with Simon in public, resulting in him fondling her tits and her touching his peen, in front of all the library patrons.

'At least he didn't invade my cooch, once in a day is enough.'

Finally, she gave Kenny the photo of her asshole, but the ancient Prof. Henry saw it.

'Wow, what a wild day. Am I an exhibitionist? No... maybe... anyway, I need to have a stern talk to Dens, he was paying too much attention to that temptress Cynthia.'

What would Dennis say? What would Dennis say... well, I guess she would have to talk to him about the work event, the daily pic and show him the dildo.

She was not planning on telling him anything else.

'Sorry Dens, what you don't know won't hurt you.' - she decides, for the third time that day.

~~~~~~~

Night

Lana arrives home and immediately does laundry. She couldn't forget it again, today's panties were her last.

'Imagine going to school without any....' - she shudders at the thought, secretly excited.

She tidies the house, folds the laundry and eats a quick meal.

Around 9:30pm, Dennis arrives home, in a drunken state.

"Hi, babe... hic..." - he greets her.

Lana gives him a quick kiss on the lips

"Ew, you stink of booze, mister." - she says giggling. "Had fun?"

"Uuhhh... yeah... I just need to sit down and recover for a bit." - he says, plopping down on the couch.

She brings him some water and an ibuprofen.

"I want to talk to you about some stuff." - she says, slightly embarrassed.

"Me too! But you can go first...hic..." - he says disoriented, the living room spinning.

"Why was I not invited?" - she asks, pouting.

"Uuhhh... Lucius didn't want people that are not part of the team..." - he says holding the couch so the spinning would stop.

"I am part of the team, the guys said it last time." - she protests feeling sad.

"Well... he said he didn't feel like you were... that you avoided him... he felt you judged their ways... hic... don't worry babe..." - he tries to explain and reassure her.

"Should I be more open in the next event? Would that help?" - she asks, seeing the light at the end of the tunnel.

"Sure, babe... anything you want... Lucius will be happy... ugh..." - he mumbles.

"Okay!" - she says excitedly. "I think I can manage that. I feel like I have grown a lot since last week." - she puffs her chest out, proudly.

"That's great..." - he slurs.

"Did you like the pic I sent you?" - she asks shyly.

"Babe, it was awesome! I got a stiffy immediately!" - he says merrily, gesturing wildly.

"Did you... masturbate?" - she whispers.

"Nah... we were in public, so I couldn't...but I loved it..." - he admits.

"So, can I keep doing a 'daily pic' from now on? Your friends helped me with the concept." - Lana says frankly.

"Ah... that would be great...you can keep doing it, I would like that." - he says with a big smile.

'Oh, so Dens doesn't mind. Glad he is on board. I can keep sharing with the guys and getting their suggestions.' - she evaluates.

"Thanks, hun for giving me permission. It will be fun." - the future-wife says.

"Yeah, and I bet it was Justin's idea... he is a sly one... hahah." - her fiancee chuckles.

"Right! Ah, also, have something to show you." - she giggles and opens her purse, pulling out the eight-inch-long blue dildo.

"W-what is this?" - he asks, wide eyed. Everything was foggy in his mind.

"It's the dildo from the play! Remember? It is ridiculous, right?" - the pretty betrothed says.

"Erm... sure... hic... but... ummm... why is it so big?" - Dennis questions.

"Ah, it is something to do with the cheating wife liking penises on the larger size." - she shrugs. "But it looks stupid right?"

"So lame..." - he chuckles. "Doesn't even look like a real penis!" - he says, opening his arms in exasperation.

"Do you think a real one would be better?" - she asks, unsure.

"Course! This is the wrong color... hic... you said it's simulated right?" - he asks lazily.

'Woah... is Dens suggesting that I simulate on a real penis? No way, I must be misunderstanding. I better make sure.' - she contemplates, her mind perverting his words.

"It is simulated, but... are you sure about it, hun?" - the fiancee asks hesitantly.

"Yeah! So a fleshy one would look more authentic!" - he bellows, smashed.

"Oh, I see..." - she says surprised.

'He is giving me permission to try on a real penis! And here I thought he would be against the dildo. Well, in a way he is. What a turn of events, Dens is always surprising me, that's why I love him.' - she thinks lovingly and anxious about his words.

"Mary and the students will be happy to hear that." - she continues with a shy smile.

"Eh... hic... surprised you didn't think of it sooner." - he says shaking his head.

Dennis was very confused, he didn't understand why she was so amazed at the idea of using a flesh-toned dildo, instead of the blue one. He was too drunk to spot the misunderstanding.

"If you say so. I will think about it." - she says flustered.

"Yeah, there is not much of a difference really." - he shrugs, befuddled by her answers.

"There is not? But..." - she says, her eyes wide as saucers.

"Nope. Seems like the same thing to me." - he states nonchalantly, still inebriated.

'Gosh... Dens really is saying that a penis is the same as a dildo... so if he is okay with me playing with a dildo, he might be okay with me using a peen instead? No... can't be. I'll ask him in bed.' - her mind whirls with her fiancee's words.

"You might be right. Thanks, dear." - she says, giving him a peck.

The smell of booze permeates his clothes and breath.

"Any time..." - he says, proudly to have helped her predicament. What was her issue again? He couldn't recall.

"Ah, you said you had something to tell me about the event today?" - she remembers.

"Unnn... yeh... I have been trying to keep away from Cynthia... but we ended up drinking... she wasn't leaving me alone the whole party... even though Paul was there! She flashed me her boobies and panties multiple times... I don't know why... it was some sort of game... please don't be mad. I was drunk and confused..." - he says, everything spilling out of his mouth at once.

"Dennis! Why... and we just got even today, so we were going to fool around!" - she says exasperated.

"Did we?" - the future-husband asks, confused. He didn't remember that. Weird.

"Yeah, we did get even, so I was going to lick your cute lollipop today." - she explains, frustrated.

"But... we can still do it... I behaved... it was just her trying to push me... I resisted!" - he pleads.

"You promise nothing else happened?" - she asks, her eyes squinting.

"Cross my heart and hope to die!" - he says making a big gesture.

"I believe you then. I will ask the guys tomorrow." - she says with a fond smile.

"Do you forgive me?" - he asks, both hopeful and drunk.

"Yes, Dens. I cannot be mad at you for that tramp's behavior." - she admits.

"Thank you... can we still mess around?" - he asks in an endearing way.

"Sure, Mr. Pervert! But just because you and your weenie are too adorable!" - she giggles.

"Aw yeah!" - he pumps his fists up. "Okay, meet me in bed!" - he rushes out the living room, stumbling over a bunch of stuff in the way.

'I love him so much. With each passing day I feel like we understand each other better and better.' - she smiles, getting up and making her way to the bedroom.

~~~

They quickly get ready for bed, with Dennis making a drunkenly mess out of everything.

As soon as they lay down, he pulls his pants down enthused.

"I'm ready!" - he announces, still feeling plastered.

She looks at him and he is still soft.

"Does not seem like it." - she comments, feeling warmth between her legs.

"Silly goose, you just need to play with it." - he gives her a big grin.

Everything was still out of focus for him.

Lana starts to fiddle with his little guy, but nothing happens. She tries to jerk it a bit more, but nothing.

"Erm... it's not working, hun." - she admits, disappointed with herself. "I'm bad at this."

"No, babe... I just... had too much to drink. Maybe if I see your boobies?" - he begs.

She lifts her nightshirt, exposing her marvelous mountains to his viewing pleasure. He groans with desire and his wee-wee stirs.

Taking it as a sign of progress, she doubles down on her fondling efforts. Nothing happens.

"Should I... ahm... try to lick it?" - she asks, embarrassed.

"Yeah, that will certainly help!" - he agrees inebriated and drowsy.

She lowers her hot mouth to his peepee and starts to gently lick it. In a few moments, she is dutifully lapping at his head, shaft and balls.

To no avail.

"Gah... sorry, baby... I think I have whisky dick..." - he admits in shame.

"It is my fault, right? I knew I was not good enough." - she says thwarted. 'I need more practice to make him happy... Mary warned it... Dens need someone good.'

"No... it felt amazing... it's just... I drank too much..." - he says with a yawn.

"Okay..." - she sighs, both upset at herself and unfulfilled for not being able to fool around.

"I think I need to sleep... maybe we can try tomorrow night..." - he says, yawning again.

His eyes close as he starts to drift off to dreamland.

Suddenly an idea comes to her head.

'I can ask if he is okay with me playing with the dildo, and if he is, he said it's the same as me playing with a penis in the future! Not that I plan to, but at least I have his blessing, just in case it comes up.' - she considers. Her naive mind was more and more corrupted.

"Dens..." - she whispers. He opens one eye lazily. "Is it okay if I play with the dildo? You mention it is the same thing, right?" - she says, trying to make sure.

"Sure, babe, anything you want..." - he mumbles an answer, too intoxicating and sleepy to comprehend the real meaning behind her words.

"Thanks! Good night, dear." - she says. And he turns around half-asleep.

'Gosh, it's true then... he is okay with it. I wonder what changed his mind... oh well, let's not dwell on it too much, he approves and it's all that matters.' - she reflects, retrieving the dildo from the living room.

The naughty and credulous teacher lays back in bed and starts to rub the dildo on her cooch, above her panties.

She had never used any toys before, so the sensation was exciting and new.

In a few minutes, she was sliding it up and down her wet slit, her panties long forgotten at the end of the bed.

She was moaning loudly, but still careful not to put the dildo in her virgin hole.

Her mind was wandering between the events of the day: the fingering, the titjob, the erections, the photos, the exposure. Everything.

The stimulation of the dildo and the build up from the day was a lot for our inexperienced teacher.

That night, Lana had two strong orgasms, all while masturbating next to her passed out fiancee.

~~~

To be Continued in Chapter 10, "New teaching uniform and raunchy slideshow."

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

Afterword

Thanks for reading. Any feedback is appreciated!

Next chapter should be smaller and encompass just Friday. I originally was going to combine it with Saturday morning, but releasing just a small-ish day (Friday will be mostly uneventful), I can probably publish it quicker.

Thanks for the support and all the suggestions, much love!

~ Potato Head