Naive Teacher in Winston - Side Story - Chloe

"More..." - she whispers to Kenny, her sultry voice filled with desire.

The janitor starts to pull his pants down to free his raging boner.

The principal realizes that he needs to put a stop to the situation before the young tarts gets fucked by the custodian in his office. That would be a scandal indeed.

"*Caham*! Thanks Kenny, that will be all." - orders the principal.

The tall pale man scrambles to get his pants back up and moves away from the student.

"Yes, Mr. Principal. Thanks for the authorizations." - he says with a slight bow. "And thank you, Miss Chase, it was hot. Seeya around!" - he says with a dumb smile.

"You're welcome, young man. Keep up the good work. Chloe, what do you say?" - asks Bill expectantly.

"Thanks for the spanks, Kenny. My ass appreciates it." - she says shyly.

The janitor nods and leaves, closing the door behind him.

~~~

Outercourse Training

"Well done, Chloe, you behaved perfectly." - the principal compliments her.

"Yeah, but that almost got out of hand, it was a little scary." - the blonde admits, although she was still feeling frustratingly horny.

"Don't worry, Kenny is a decent guy, he just needs to be ordered around, or else he can turn into a wild animal." - the old man laughs.

"Really?" - she asks, images flashing on her twisted mind.

"Oh, yeah. He was pulling his pants down, if I hadn't stepped in, he would have fucked you senseless." - the principal says.

"Wow... ahm... thanks for looking out for me, Uncle Bill." - Chloe says.

"You're welcome. Now let's continue where we left off." - he says.

She starts to put on the first outfit. She is quite enjoying showing off to Drew's uncle, it feels somewhat taboo. She finishes getting dressed and then poses for him.

"Hmmm, it doesn't work." - he says adamantly.

"What doesn't work? I think it looks pretty cute." - she says looking in the mirror.

"Right, but I think your underwear is in the way. Take it all off and try again." - he instructs.

"Is it necessary? I think we can have a good idea." - she asks.

"Yes, it is. But don't worry, I have seen you wearing less." - he reminds her. "And I have touched you all over, as have the rest of the family." - he winks.

"Please don't tell Drew, he wouldn't like it." - the blonde pleads.

"Of course, but don't forget I saw your beautiful tits and pretty snatch already and he accepted it." - Bill says.

"Well, he doesn't particularly enjoy it..." - she explains.

"Ah, he'll get used to it, it's expected from the family. And I sense that you don't mind it much, you are way naughtier than I judged. I approve." - he says.

"No! I also mind it! I'm not entirely comfortable with being naked in front of you." - she admits.

"Ah! I see the problem now..." - he exclaims.

Principal Bill starts to quickly disrobe. Chloe is taken aback by his sudden behavior. She interrupts him when he is wearing just his loose boxers.

"Uncle Bill! What are you doing?" - she says, slightly covering her eyes.

"Getting naked with you. This way you'll feel more at ease, since you're not the only one." - he explains nonchalantly.

He starts to remove his underwear.

"That is not what I me...." - the blonde starts to protest.

Chloe trails off when his huge penis comes out. She just stands there staring at it. His member is thick and long, and his swollen balls hang low, covered in white pubic hair.

It looks like the old man is sporting a baseball bat with a couple baseballs between his legs. Chloe's big dick fetish seems to take over her mind and will, now she has only one thing in her head.

"Wow..." - she says quietly.

"Do you like it? It gets a bit bigger when hard. I never heard complaints." - he brags.

"How big does it get?" - the blonde student asks bashfully.

"Around 9 inches I believe, but it's been a while since I measured it!" - he boasts.

"Almost twice as big as Drew..." - she says absent-mindedly, eyes fixated on his cock.

He smiles, this was going better than he hoped for, the girl was in dire need of a real dicking.

"See, I told you. I knew you would be more comfortable if you weren't the only naked." - he says with a sly grin. "Now let's fix this."

He approaches her and deftly unclasps her bra. She can see his dick growing as it rubs against her bare skin.

"Finish removing your bra and I'll take care of those precious panties." - he orders.

She feels her nipples ache as she removes her bra, letting her bare tits out. Chloe has decently sized breasts, extremely perky, with small dark red areolas and tiny pointy nipples.

The principal smiles and sits back down. He pulls down her panties and exclaims pleasantly when he sees that she is fully shaved. He can tell she is sopping wet as a trail of her juices dribble down from her dark red slit into her panties.

"Beautiful, that is how Winston-Phillips's women should be, bare." - he praises.

"Thanks, I prefer it. Feels cleaner this way." - she explains.

"Me too, and she smells great." - he says, taking a deep whiff.

"Erm, thanks, Uncle Bill." - she says bashfully.

"Now it's your turn to undress me." - he says with a grin.

"Hm? You're already naked." - she says, ogling his old cock.

"Well...." - he says and points down at his socks.

She lets out a surprised exclamation, she knew what was going to happen.

Bill opens his legs wide, and she kneels between them, extremely close to his masculine penis, who seems to be growing harder by the second.

"I noticed your pussy is wet, did Kenny get you excited?" - he asks. "Be honest."

She starts to remove his left sock. Her face is inches away from his almost fully erect cock.

"Yes, I enjoyed the spanking. And seeing your big dick. I wish Drew would let me play with his wiener more." - she admits.

"Well, I am family, so he will certainly not mind if we fool around a bit." - Bill explains.

"Are you sure? I don't want to upset my boyfriend." - she asks, removing his right sock.

She glances at his dick, who is now at maximum attention. It was the biggest she had ever seen, even larger than Lukas's. It was so thick and meaty, and she wondered if it would hurt if it slid inside her.

"Of course! I am his great uncle, and we come from a long line of Winston-Phillips's men. It's important that you are well trained for him." - he says nonchalantly.

She is staring intently at his large member. He moves forward a bit and starts to rub it against her face.

"You know I am devoted to Drew, that's why I can't cheat on him." - she says, practically salivating over it.

Her pussy juices were dripping on the floor, obscenely.

"This would not be cheating. Think of it as practice." - he informs.

"Okay. Just a little bit then. What should we do?" - she asks as her twat twitches.

"I would love to have you suck on it, but I don't want to end this too quickly." - he says, and she looks somewhat disappointed. "How about you come up and sit on my lap, so I can show you some moves." - he says lecherously.

"Okay, but no sex, I am a virgin. My pussy is off limits." - she reminds him. He nods.

She stands, letting his prick rub all over her face and chest. When his massive dick contacts her tits, she lets out a loud groan.

She straddles him, pinning his cock between their bodies. She is in ecstasy.

"We call this outercourse." - he says. "Doing it like this, allows you to rub your slobbering cunt along the shaft of the penis without the risk of it going inside." - he explains to her.

He holds her by the waist and starts moving her up and down, her virginal cooch sliding along his big member. They keep grinding for a bit. Chloe is moaning deeply, extremely close to coming.

"Of course, you can't go too high, or it can accidentally penetrate your snatch. Like this..." - he says.

He lifts her up until the head of his dong is aligned with her vaginal opening. He pokes at it and puts a quarter of his cockhead inside. She cries with pleasure, almost climaxing.

He then immediately puts her back down, sliding her cunt along the length of his erection.

"Ah...." - she lets out a frustrated sound, not hiding her disappointment.

He repeats the move another time and again she lets out an upset guttural noise.

"Maybe another time." - he winks at her. "However, if the guy is too small, this might be risky. How big is Andrew again?"

"Hmm... probably a bit more than half your size, but way thinner." - she admits, panting.

"Yeah, that won't do. I guess I need to show you another position." - he says.

"Yes, please... yesssss... teach me, Uncle Bill." - she nods enthusiastically.

He holds her waist and pushes her away from his cock. He then slides the head of his penis across her whole slit, letting it come out at the bottom, momentarily poking her asshole on the way. She moans, her orgasm imminent.

He positions her back on top of his shaft, letting it part her pussy lips lewdly. He then starts to slide his hog back and forth on her slit, coating it in her dripping juices. She groans lewdly.

"Do you like this one?" - he asks.

"Oooooh.... I do... fuuuuuck... so I need to do this with Drew... feels good..." - she moans.

"Yes, and if he doesn't want it, come here and I'll help." - he says. "Now, are you ready to come, little slut?" - he asks.

"Yes... Yes... please..." - she pleads.

"Where do you want to come? All over my dick? Ask me like the good tramp that you are." - he orders.

"Mmm... all over your big fat cock... ngg... yes... let me squirt on it, like the slut I am... fuckkkk... slide your cock all over my wet pussy... yeeeesss... I'm a pervert... letting Drew's uncle slide his big cock on my virgin cunt... fuuuuuuck... nnnng.... Yesssss..." - she cries, climaxing hard onto the principal's prick.

She shakes uncontrollably on top of him, having had the most intense orgasm of her young life.

Principal Bill gives her some time to recover, his steel hard member ready for a climax of his own.

"Well done. Andrew will be pleased with your progress." - he states. "Now it's my turn..."

A knock on the door brings him back to reality.

"Tsk..." - he says. "Give me a second!" - he yells at the person behind the door.

He lifts Chloe and plops her on the couch, as if she didn't weigh anything. He gets up, opens a closet and takes out a big fluffy robe, putting it on and tying it tightly.

"Come on in!" - he says with blue balls for not having ejaculated.

Chloe finally realizes what is happening and she panics, but it's too late.

~~~

Prof. Henry Sesh

The door opens and an elderly scrawny man comes in. He seems to be a bit younger than Bill, but not by much. He has a mousey look and feel to him, being short, small and white-haired.

The senior man stops dead on his track when he sees the naked blonde student, unsuccessfully trying to cover her bits.

"Oh, s-sorry, d-didn't mean to i-interrupt." - he stammers.

"Nonsense, Henry, join us. Chloe, you know Prof. Henry, right? He is the music and tech teacher." - the principal says.

"Erm... yes... hi Prof. Henry. Can I get dressed, Uncle Bill?" - the sexy class-rep asks flushed.

Henry is so hypnotized by the young tart that he doesn't notice that the principal is in a robe.

"I don't see a reason for it, we'll resume as soon as I talk to Henry, so stay put." - he orders. "What can I help you with, Henry?"

"Oh... erm... well... you see... I was wondering if we can get a couple of new instruments for the class." - the professor stammers, not breaking eye contact with the nude girl.

"Of course, you have my approval. Stella will arrange anything you need." - Bill says.

"T-thanks, Bill." - the skinny man says, not moving an inch.

"Anything else? We need to keep going here." - the principal says hastily.

"What w-were you two doing?" - the scrawny teacher asks.

"Ah, just trying some new uniforms for the students." - Bill answers.

"C-can I s-stay and w-watch?" - asks Henry with a lustful look.

"I don't see why not. Are you okay with that Chloe?" - he asks rhetorically.

"No!" - the principal stares at her. "Ah...I guess so." - she says reluctantly.

"Very good, you made the right choice. It's what is expected of a woman with the Winston-Phillips name." - Bill nods approvingly.

"Erm... do I have to be naked the entire time? It's embarrassing." - Chloe protests.

"Of course, dear. You didn't complain much until now." - the principal reasons.

"It's because you are my uncle, and you gave me no choice!" - the blonde argues.

"Well, nothing changed in my view." - says Bill, pointing Henry towards an empty couch.

The elder teacher sits down with a lecherous grin.

"Professor Henry is here now! Drew is not going to like me being naked in front of him. Can I at least put on my underwear?" - she asks in a desperate attempt.

"No, you will stay like that. I am Andrew's uncle, so he'll have to get over it." - the old principal says sternly.

Chloe sighs deeply, she was already expecting his answer, there was no way to reason with a male from Winston. Especially the ones from the family.

She was feeling mortified. The only men who saw her fully naked before were Andrew and Bill. Yes, some family members saw it, but only glimpses when they were molesting her.

Nevertheless, parading totally bare in front of a random teacher was too much for her.

"You can go ahead and start trying on the uniforms!" - Bill says nonchalantly.

Chloe starts to try on and go through different outfits. Both men express their approvals and their dislikes. In total, the blonde volleyball captain was naked for over ten minutes in front of the old man.

Her pussy was completely damp again, thoroughly enjoying the unwanted attention and slobbering everywhere.

The class-rep was worried, she was starting to relish these situations too much, even if she was slightly betraying her boyfriend. Maybe that's why Mary did it. She wasn't expecting to see eye to eye with Mrs. Hunter on this day.

Both men were fully hard after the shameful exhibition by the young temptress, as is evident by Henry's pants bulge and the principal's massive tent on his robe.

"Well done." - the principal claps. "I think we have a few winners." - he says.

He puts a few winning outfits to the side, for Lana to wear in the future.

"Thanks for letting me watch it Ms. Chase, this made my year." - admits Prof. Henry, not nervous anymore.

"I didn't have a choice, but you're welcome." - she says defeated.

"Thanks for the input, Henry bud. Before you go, want to request anything from Chloe?" - Bill asks.

"Anything?" - the scrawny elderly asks lustily, adjusting his boner.

The blonde turns red, imagining all the ways the professor could ravage her.

"Sure, she's also in training today, so it would be good for her future." - the principal assures him.

"In that case... since she has been flaunting that tight body of hers, I need to try it. Can I give her fresh cunt a lick? I could smell her pheromones the whole time." - Henry asks, any hint of shyness gone.

The blonde athlete gasps. Nobody had done that before.

"Hahaha!" - guffaws Bill. "Of course, of course. Chloe, be a dear and sit down on the couch and spread your legs for Henry here." - he says nonchalantly.

"I don't think I should. Andrew has not done it yet." - she admits timidly.

"Well, it's just another 'first' that my nephew will miss. No worries." - Bill says.

"Just one lick, please. I haven't had a tight young twat in my mouth in years." - the teacher pleads.

"Go ahead Henry, she doesn't mind." - the principal says.

Knowing it was useless to debate, Chloe reluctantly sits down fully naked on the couch and spreads her legs wide, giving them a perfect view of her bare dripping dark-red snatch.

"It's perfect..." - says the scraggy professor in awe.

"Go ahead Henry, we don't have all day." - his boss hurries him.

Not wasting time, he kneels in front of her and dives forward, licking from the bottom of her wet slit, all the way to the top, where her pubic would have been.

Chloe moans intensely. The sensation was like nothing she has ever experienced.

Instead of stopping at one lick, the boney old teacher starts to lap at her pussy, eagerly.

"That's enough, Henry. You had your fun, now get out." - Bill orders.

"Ah...." - the turned-on girl groans, not wanting this to end.

The senior man dislodges from her virginal sex, stands up and lick his lips lewdly.

"Thanks, Ms. Chase, exquisite taste. I'll see you again." - he winks. "Thanks, Bill, for the instruments." - he says, walking away hunched over, trying to hide his erection.

Still on the couch with her legs spread, Bill approaches her and opens his robes, freeing his huge hard-on. Fearing that he was going to fuck her, Chloe recoils a bit.

"Don't worry. I won't do anything. I just wanted to request something." - he explains.

"What is it, Uncle Bill?" - she asks innocently.

He kneels a bit and starts to hit her wet snatch with his dick, slapping it obscenely. She moans loudly with each cock-smack.

"So, I was thinking. From now on, how about you wear skimpier outfits? Maybe skip the bras entirely since your tits are so perky anyway." - he proposes, midst dick-slap.

"Ah... mmm... uh... I suppose... I could do that..." - she agrees between moans.

"You can even forego your panties sometimes. Only until we get the new uniforms." - he says.

"Ahh... I'll do it... hmm... I'll feel so slutty all day... Drew will be upset... ahhh." - she moans.

"He'll get over it." - Bill says. "You like this, you little slut?" - he asks, smacking her with his cock even harder.

"Ahhh... yessss... I love it... hit my cunt with your big fucking cock... ah... more..." - she pleads.

He suddenly gets up and ties his robe back. He knew it was not yet the time to take things any further.

"What... no..." - she complains softly. She was so close.

"I have an appointment soon; we need to finish this." - he says sternly.

Disappointment was stamped all over the pervy blonde's face. She wanted more, but she was not going to get it this time. She was frustrated again.

Suddenly, there is another knock on the door.

"Come in!" - says the principal merrily.

~~~

Hunter Sesh

In comes Mary Hunter, dressed in a nice tight pencil skirt and an opened button-up blouse, emphasizing her cleavage. Her breasts were made more pronounced due to her fake boobs.

"Oh, great of you to finally join us." - exclaims Bill, pleased.

She glances between him and the wet naked slut on his couch and giggles.

"Erm... this is not what it seems..." - Chloe stammers.

"Of course, it isn't." - Mary says giggling. "You were just trying the new uniforms, right?"

"Right... that is what we did... that is why I'm naked..." - the blonde excuses.

"And dripping pussy juice. Suuuuuure. Shame on you, Bill." - Mary winks playfully.

He laughs at the naughty teacher's acting.

"Don't make her feel bad, dear. We didn't go too far, today." - the old man says.

"Oh, so you didn't cheat on Andrew?" - Mary asks the horny teen.

"No, I am not like you..." - she retorts softly.

"Oh, I see. Well, don't worry, you seem to be more and more like me by the second." - she smiles. "I am also obsessed with huge pricks."

"I don't love large dicks... Uncle Bill is just helping me practice..." - Chloe says.

Mary giggles, impressed by the blonde's conviction.

"As you can see, she's still resistant to some things. Give her time." - Bill acknowledges.

"Good, that means I still can still have your big cock?" - Mrs. Hunter asks nonchalantly.

Chloe gasps at the teacher's attitude. Mary could be very forward sometimes.

"You can, I haven't gotten relief yet, this little tramp left me hanging." - Bill says with disdain.