Naive Teacher in Winston - Side Story - Chloe

Winston Stories: New uniform tryout with Bill and guests.

Foreword

Everyone in this story involved in any sexual activities is at least 18 years old. This story is not real and probably could never be real in 2022, so any correlations with real-life are mere coincidence.

This story is part of the Naive Teacher in Winston stories. It is strongly suggested that you read Chapters 1-8 first.

This story happens during Day 11 (Chapter 9), showing Chloe's side story with Principal Bill and some other surprise guests. Lana won't appear in this story. The timeline is between Chapters 8 and 9.

Enjoy the read,

~ Potato Head

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Day 11 -- Thursday

Morning -- School

Chloe Chase knocks on the imposing door of the principal's office.

"Come in!" - says a voice on the other side.

The blonde opens the door and is surprised to see Principal Bill sitting on the couch with a couple of oversized shopping bags.

"Hello, Mr. Bill?" - she says unsure.

"Chloe! Thanks for agreeing to do this. Also, as I told you before, please call me Uncle Bill." - the old man says with a wide grin.

He gets up to greet her. Bill is as tall as his nephew Andrew, at 6'3, and she can see that he was once a very attractive man, even if he was old and slightly overweight now.

"Oh, sorry, Uncle Bill. It always feels weird calling you that at school." - she explains.

"Nonsense, we are family. Now come give me a hug!" - he orders.

She approaches him and they embrace intimately, with him taking a big whiff of her scent.

He then puckers his lips, expecting a kiss. With reluctance, she stands on her tippy toes and gives him a quick peck, the loud smacking sound echoing across the room.

"Thanks, darling." - he says, breaking the embrace and sitting back down. "Hopefully, Andrew is taking good care of you." - he mentions, emphasizing the words.

"He is, Drew is a great boyfriend." - the cheery students answers.

"I know he's great, but I meant it in a sexual way. Is he making you orgasm often enough?" - he asks nonchalantly.

Chloe sighs, she was already used to the lecherous behavior of the men in Winstonstead.

"You know we are both virgins, Uncle Bill. Andrew thinks it's more appropriate for us to wait until we are out of school and can get married." - she says.

"Beh! That 'saintly' mother of his putting nonsense in the boy's mind." - he shakes his head disapprovingly. "Nevertheless, have you been doing other stuff, like..." - he says, making a jerking motion with his hand.

"Rarely. You know how Drew is focused and serious about his future." - she answers.

"Certainly, a young sexual thing like you must want it?" - he says with a knowing smirk.

"Erm... of course, Uncle, but Drew is my boyfriend, so I have to respect him." - the young lady admits.

"Well, if you need, I can teach you a few things." - he guffaws.

"Hmm, thanks but... no need... Miss Lana has been teaching us enough." - the blonde says.

"Ah, so I heard. That is very good." - he looks at her seriously, his demeanor changing. "Still, you need practice with a real cock if you are going to be able to please my nephew and have his babies. It's expected from all the women of the Winston-Phillips family." - he says, with a reprimanding voice.

"Yes, Uncle Bill." - Chloe answers with a sigh.

~~~~~~~

Lil' Backstory

Chloe + Andrew

Chloe Chase was 13 when she met Andrew Winston-Phillips. Well, "met" might not be the right word. Introduced, perhaps.

You see, the Chase family has always been a part of Winstonstead's history, so when Andrew's parents needed to arrange a future wife to become engaged to their eldest son, the Chases were one of the first names on the list.

Their first "date" was extremely awkward. It was a dinner party at the Chase's house, with the sole purpose of introducing the two lovebirds. Chloe was dreading the event, but when she and Andrew excused themselves to have some time alone, the blonde girl was surprised by how different he was and how much they hit it off.

They have been dating ever since.

Of course, dating a Winston-Phillips came with a lot of expectations. Chloe had to attend numerous parties, have perfect manners and always be on her best behavior. She was always required to stay quiet and talk as little as possible, mostly serving as a trophy girlfriend for the young boy.

Possibly that was the reason she was so cheery, peppy and crass outside of the 'fancy scene'. She started to develop an almost hatred of the prim and proper version of herself. Naturally, she was still devoted to Drew, so he had to tolerate this and act the part when they were with his family.

A good aspect is that everyone in the family was very respectful of her and treated her as their own. She was pampered and cared for, as if she was an official Winston-Phillips. That even extended to her parents. If they kept dating, she was set for life.

Chloe and Drew had a good relationship, but it was not without any issues. They were teens after all.

She started to get curious about sexual things and opening up with her boyfriend about it. Even though Andrew loved the cheery blonde deeply, he had been groomed to be serious, distinct and decorous, so he always pushed any sexual desires or explorations aside, much to the chagrin of the girl.

As they grew and developed together, Andrew started to become more accepting of Chloe's openness about sex, but still, he refused to go any further than kissing, light touching and masturbation.

They saw each other naked on occasion, but it was rare. She thought Andrew had a decently sized penis, but at that point, she had little to no real-life experience to compare.

Secretly, Chloe became slightly pervy, interested in everything related to sex. She read books and erotic stories online, looked up videos, masturbated and fooled around with some of her friends, mainly Jen, her bestie and neighbor.

She developed strong sexual feelings towards both men and women, and while she had many opportunities to betray her boyfriend, she refused any man that even remotely tried to get close.

Her best friend Jen was always frustrated that Chloe "cock-blocked" her, but she understood that Andrew was probably the biggest catch in their age-range. She knew her friend was ultimately doing the best thing for their future.

Needless to say, Chloe was extremely frustrated and horny all the time.

~~~

Eighteen

Everything was going great until Chloe turned 18.

You see, in Winston, it was customary to leave young people in the dark until they became of age, when it was then encouraged to share with them the deepest secrets and depravities of the town.

In the first week, nothing changed. Nobody dared get near to the future wife of one of the heirs to the Winston-Phillips name. Chloe knew she was lucky, and other girls and women wouldn't share the same fate as her, being at the mercy of every person in town.

But then, a big family gathering was held.

Andrew sat down with her and reluctantly explained what could happen during the event, since they both were adults now. He didn't like any of it at all, but there was nothing he could do, since it was "tradition".

He asked Chloe to grin and bear through it. Everyone considered this just part of her 'initiation' into the family.

That night, the blonde was touched, groped, squeezed, prodded and spanked. Every adult from the family kissed her in the mouth, some with tongue, much to the anger of Andrew. Of course, he was very frustrated by the events, but acted like nothing had happened.

They continued going to a few more parties, and things kept escalating. Some men made Chloe sneakily touch their naked members, while others openly twisted her nipples in front of everyone. Principal Bill was one of those men, being known as a notorious lecher in town.

This was the time that Chloe realized that her boyfriend, and future husband, wasn't very well endowed, with most of his family having bigger and thicker penises than him.

Chloe secretly started to develop a 'size queen' / 'big dick' fetish, which soon became her most searched and viewed porn term. Sometimes she would masturbate 5 or 6 times in a row to videos of teen blondes being fucked by monster penises.

After this, Chloe started to get some more attention around town, as the 'word' started to spread that the couple didn't mind the groping and that it was safe to do so, as long as their limits were respected.

The last event was held about a month before the school year started. That was the night where Chloe was fingered by a man for the first time. In front of Andrew.

Drew's grandfather, Dick, made her sit on his lap and started groping her in front of Andrew and some of his cousins. He called it a test of some sort. The old man soon started touching her under her skirt and finding no resistance from the couple, went a step further, touching her virgin cooch directly. In a span of a minute, he was fully fingering her young pussy in front of his grandsons.

They could all see the thick digit sliding in and out of her pink wet snatch. Andrew was mortified.

Nobody else had touched her twat before, besides Jen, and now she was letting Dick, Drew's grandpa, do it in front of him and his family. Chloe was trying to not enjoy it, but it was impossible. She felt lewd and horny. She couldn't avoid the massive orgasm that was building, and soon she came and convulsed all over the old man's index finger.

Andrew was extremely upset with his grandpa, swearing to abdicate from parties for the foreseeable future. That was only a month ago, but so far, he kept his promise, and they haven't attended anything since.

None of this quenched the blonde's horniness, it was just fuel to the fire burning inside her wanton and demanding pussy. She needed more, she wanted more.

~~~

Start of School

Chloe was elated when Lana Cox was introduced to the class. She found the busty educator extremely attractive and the more time she spent with her, the more she liked her.

Besides being sexually drawn to Lana, she also valued that the teacher was loyal to her fiancee, even if she had plenty of studs throwing themselves at her or even if she constantly got into naughty situations, showing her slutty body or stroking cocks.

That was one of the reasons she disliked Mary Hunter, as the vulgar teacher always cheated on her husband. In Chloe's eyes, it didn't matter if Lucius Hunter did the same, it was still not right. She would never betray Drew.

Chloe's commitment to Andrew was iron-clad. At least, that was what she thought until she saw Lukas Hunter at school again. He had grown a lot and had developed into a handsome, young man with piercing blue eyes.

Yes, she hated Lukas, but wanted to fuck his brains out at the same time. She always got wet just by provoking him and yelling obscenities at him. She secretly enjoyed seeing Andrew all jealous and bothered by their naughty interactions.

Chloe also loved to see Miss Lana in lewd situations, it excited her tremendously, to play around with her and see others messing with her. She never wanted to be mean to her teacher, as she cared for her, but sometimes her sexual side won over.

Her most prized possession was the photo of her and Lana flashing her boobs in the Gym shower. This selfie was something she had not shared with anyone and used at least twice a week for her daily masturbation sessions.

~~~

With everything that had happened lately, Chloe knew that she wasn't going to remain a virgin much longer, even if Andrew was not up to the task.

The pot was boiling and would spill over if this train of events kept going.

~~~~~~~

Back to Present

1 on 1 Sesh

"Glad we are on the same page, Chloe." - Bill says, pleased.

"So, what am I doing here today exactly?" - she asks, changing subjects.

"Right. So, you know that we are planning some new uniforms for this year?" - he says, and she nods. "It's a delicate subject with students since we never had anything of the sorts, besides dress codes and color requirements."

"Don't need to tell me twice. You remember that the student council voted last year, and we all agreed to the new uniforms, we think it will add more structure to the students." - the young class-rep says.

"Indeed. Still, might be a tough sell, that is why I asked Andrew to convince you to try them out and be the 'image' of the new uniforms." - he explains.

"I see, that is why he was so adamant about it. You know I can never refuse him, Uncle Bill. So, what do you need?" - she says with resignation.

"We have a few different pieces to try on. Then I will order them and when they come, I was hoping you would pose for a few posters wearing the outfits, to get everyone on board." - he explains.

"Okay, but I was also under the impression that this was also related to Miss Lana?" - Chloe asks, confused.

"Yes, well observed. Lana tends to dress too conservatively. It's out of place with our customs for such a pretty, youthful lady to wear such outfits." - he elaborates.

"Uhum, I can see that. Her sense of fashion is very outdated, she dresses like my granny." - giggles Chloe.

"Exactly! So, I am going to give her some of the best pieces from today, as a 'provisional uniform' until the real things arrive later this semester." - he says. "Mary will also join us later."

"Why is she coming here?" - asks Chloe, who disliked Mrs. Hunter.

"It would be good to try the clothes out with different bodies, to make sure it fits Lana properly." - he explains. She sighs.

Chloe approaches the bags and looks through them quickly. She notices that all the pieces are in shades of Red, White and Gray, the school's colors.

"Oh, they are cute! Yeah, she will look so much better with shorter skirts and sleeveless blouses. She needs to showcase her top curves and thick ass more." - the blonde says cheery.

"Precisely. I can see why Andrew loves you, you are not just a hot body with perky tits, you are a very smart young lady." - he compliments her.

She blushes. She is normally not shy at all, so she wonders where this sudden timidness is coming from.

The principal rummages through the bags and separates the outfits into a few sets. He hands her the first one.

"Here. Change." - the old man orders with a salacious smile.

"Where should I change?" - she questions, dubious of his intentions.

"Right here is fine, just strip down to your underwear." - Bill says nonchalantly.

"I shouldn't do that; Drew is not going to like it." - she says.

"Nonsense, he asked you to help me. Besides, I talked to him." - he explains.

"But..." - she starts to say.

"Don't make me lose my patience, Chloe. It is for the good of the school and the town. I'm sure your parents will be glad you are contributing so much to our future." - the principal says with a stern face.

"Okay, but don't laugh at my underwear..." - she warns, slightly embarrassed.

Chloe starts to strip down. She first removes her sweater, leaving her in a pink cotton bra.

Bill can't help but admire her figure. Chloe is fit and sexy, with big breasts for her frame and a small tight ass. What he wouldn't give to have a piece of that virgin pussy. Maybe one day, he thinks.

She finishes removing her skirt and blushes deeply. She is wearing a pink striped thong underwear with the words 'Thursday' on it. It doesn't suit her adult body, looking more like something a young girl would wear.

"Sorry about this, I wasn't planning on anyone seeing it." - she says, flushing.

"No worries, looks dandy on you. An interesting contrast with your fit body." - he says with a lecherous smile.

~~~

Kenny Sesh

They hear a knock on the door.

"Come in!" - says the principal loudly.

The door opens and in comes Kenny, the school's janitor.

Having been caught by surprise, Chloe shrieks and covers herself with her hand.

"Oh, shit! Didn't wanna interrupt, I'll come back later." - says the janitor.

"Nonsense, Kenny, stay. Chloe doesn't mind, right?" - he tells her.

She nods, still covering herself.

"Ahm, okay. If you both say so." - Kenny shrugs indifferently.

"We do. Now, Chloe, don't make young Kenny here feel uncomfortable. Remove your hands. You are making it seem like something inappropriate is going on." - Bill orders.

"Yes, Uncle Bill." - says the blonde student.

She removes her hands and tries to stand at attention. She closes her eyes with shame.

Far from Kenny to complain about the situation, as he is practically drooling over the sexy volleyball captain's body. He knew how forbidden it was to get involved with someone from the Winston-Phillips family, and this blonde tart here was the next best thing.

Chloe is feeling so embarrassed, she can feel the janitor's eyes burning a hole through her already small underwear. Andrew would hate it if he knew that she was practically naked in front of the custodian.

"So, Kenny, what can I help you with?" - asks the old man with a cheeky smile.

"Well, you see Mr. Principal William..." - Kenny starts to say, and dives into a small list of issues that he needs authorization to fix.

The janitor's eyes are glued onto the scantily clad girl the whole time. She can't help but notice a huge bulge growing in Kenny's pants. It looks enormous. Her eyes widen and she starts to feel horny.

"(...) and that's it." - the man finishes explaining.

"Okay, you have my authorization. Tell that to Stella. Also, if I recall correctly, you are an ass-man, right?" - the principal asks.

"Thas right, Mr. Principal William." - the janitor admits.

"Call me Principal." - he says impatiently. "And you are in luck then. Chloe, please turn around and bend over, to give Kenny here a good look." - Bill says nonchalantly. "He has been doing a great job, so he deserves it."

Chloe's mouth falls open. She is initially conflicted, but her naughty side quickly wins the argument.

Turning fifty shades of red, the blonde athlete turns around and bends over, presenting her small tight ass to the custodian. She can feel her wanton pussy pulsating under her 'Thursday' panties.

"Wow, fucking hot. Thanks Mr. Principal!" - Kenny says, adjusting his massive bulge.

"Go ahead and give her a couple spanks." - Bill says, adjusting his own member in his pants.

Chloe looks at the old man to complain, but upon seeing them both sporting big erections, she decides against it. She arches her back, offering her tush to the pale janitor.

Without hesitation, Kenny approaches her and slaps her right ass cheek with gusto.

*smack*

The sound echoes lewdly in the room.

"Ouch!" - the blonde yelps. It felt good. She arches her back again, asking for more.

The janitor once again slaps her ass, this time aiming more towards the middle of her butt.

*smack*

The peppy student squeals, a mix of pleasure in her voice.

"One more for good measure." - instructs the principal.

Kenny aims between her cheeks and lets his hand fly.

*smack*

"Ahhhhh...." - the naughty class-rep moans, having been slapped right on her aching cooch.

"Very good, nicely done, young man. Now rub where you just hit her, we don't want her to be sore tomorrow." - Bill commands.

"Yes sir, Mr. Principal." - the janitor says.

Foregoing any demeanor, Kenny places his palm on her mounds and starts to touch it. He blatantly rubs her pussy above her panties, smirking at how damp they are.

Chloe moans loudly with lust. She was feeling horny and aching for more.