Naive Teacher in Winston - Side Story - Andrew

Winston Stories: Andrew's mother is a slutty reporter.

This short tale is part of the "Naive Teacher in Winston" stories. It is strongly suggested that you read some of the other Chapters first.

~~~

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 coincidences.

It is highly encouraged to read "Side Story - Chloe" before this story, as that one gives a lot of backstory on Andrew and Chloe's relationship.

This quick story happens before the start of the original series and focuses solely on the Winston-Phillips, more specifically Andrew and his family.

This tale serves as an insight into Winston's customs and origins. There is not a lot of sex as the goal was to establish some backstory.

Enjoy the quickie!

~ Potato Head

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Intro

~~~

Andrew

Andrew "Drew" Winston-Phillips grew up pampered and sheltered. He had the best of everything. His pampering parents and his overindulgent family made sure of that.

The Winston-Phillips family were the founders of Winstonstead and they owned one of the largest trading/transportation/cargo companies of the Midwestern United States, the Winston-Phillips Co. Needless to say, his family was wealthy and powerful.

Andrew was the only child of Nigel and Jade. Nigel had a similar life story as Andrew, as he had been born a Winston-Phillips. Jade, her actual birth name, on the other hand, was a simple hostess from a low-class family. Young Nigel and her met during a work trip to Las Vegas and they immediately fell in love. They eloped in Vegas that same week, and she moved back to Winston with him.

Not even a fortnight had passed when the newly-wedded couple announced that Jade was pregnant. The other women from the Winston-Phillips family disliked the redhead at first, but they warmed up to her, especially when baby Drew was born, with his impossibly cute dimples and his pretty white-blonde hair.

Andrew's grandfather, Richard, was the most powerful man in Winstonstead, as he was both the Mayor and the President of the company. Together with his brother, William, they played an important part in making sure Jade was accepted and well-received into the family. Both of them were always around when Drew was going up, and he was thankful for that, as both men were always nice to him, always inviting him to play catch, chess, or other fun games.

The boy loved his life, he was extremely rich, loved by his parents and his grandparents, and had a wonderful girlfriend, Chloe Chase.

The two teens got together when they were both 13 years old and had been together ever since. They had a lot in common and they complemented each other, with Andrew being more serious and calm, while Chloe was always smiling and having fun. He helped her become more thoughtful about her studies and her future, while she taught him to relax and savor his financial condition.

Of course, things were not without turmoil as Chloe started to blossom sexually. Andrew had been groomed by his father and mother to be serious, distinct, and decorous, so sexuality to him was something to be done only by husband and wife behind closed doors. Chloe was displeased when he told her. He gradually became more open, but nothing beyond kissing, light touching, or masturbation.

One of the reasons Andrew avoided any sexual act with his girlfriend was that he was overly self-conscious about the size of his penis. Of course, his dick was under development, but he couldn't help but worry, especially since a lot of his classmates and family members had a huge advantage over him in the endowment department. Chloe insisted that this wasn't a problem, but he knew better.

~~~

Eighteen

Nevertheless, Andrew was on top of the world.

Why? Well, it's easy to see...

Drew was handsome, tall (6'3), and had comely blonde hair. All the girls would swoon as he passed. Even the older ones.

In school, he was top of his class and he was also the Captain of the Wrestling Team. He was primed to an Ivy League university with a full scholarship, not that he needed it. Once he came back, he had a guaranteed job with a bright future ahead, as eventual CEO of the Winston-Phillips Co.

Currently, his father was the vice president of the company, and soon would be taking over the presidential duties, as Dick was planning to retire in the next few years. His mother Jade worked as a reporter for WinstonTV, the local broadcasting channel, owned by his family. She was well beloved by all the people in town and was treated as a celebrity everywhere she went.

Things started to take a turn for the worse after Andrew (and Chloe) turned 18 years old.

Winstonstead had an extremely adult and dark side, full of deep secrets and depravities. Nevertheless, it was customary to leave young people in the dark until they became of age (or sometimes even later). After that, they were to slowly be initiated into the town's real customs by family members or close relatives. Some initiations were brutal and sudden, while some were sweet and gradual.

Andrew's abrupt initiation came on the weekend after his 18th birthday. This is that story.

~~~~~~~

Revelations

~~~

Dick and Bill

It was Saturday and the sun was setting in Winstonstead. Andrew was walking along the fancy cobblestone path that led to his household. After a day of wrestling training at school, the 18-year-old boy was exhausted, but that didn't stop him from spotting his great-uncle's car next to his father's. However, his mother didn't seem to be home yet. The teen sighed, remembering that she worked until late at the TV station on Saturdays.

"I am home!" - Andrew announced, as he took his shoes off and exchanged them for posh slippers. The Winston-Phillips never wore outside footwear indoors. That would be outrageous.

"Andrew, we are in here!" - he heard the voice of his great-uncle William booming from the living room.

Excited, the teen rushed to greet his favorite uncle. As he entered the living room, he was surprised to also see his grandfather there, along with his dad. The three men were seated on cozy armchairs around the fireplace.

"Oh, good afternoon, grandpa Dick!" - he said, pleased. His grandfather was his favorite person in the world.

Richard 'Dick' Winston-Phillips was an old man. He was well into his seventies, but still jovially fit and elegant, with white hair and a cheeky smirk that Drew loved. His grandfather loved to play pranks on people, much to the delight of his grandson.

"Hello, hello, Drew. Your timing is impeccable." - Dick said with one of his classic smiles.

"Greetings dad, greetings uncle Bill." - Andrew said to the other two men.

William 'Bill' Winston-Phillips was extremely different from his brother. Besides being a bit younger, in his late-60s, Bill was a big man, being a couple of inches taller and twice as wide as his older brother. Due to his physicality, he looked more like a retired NFL defensive lineman than the Principal of Winston's School. He was always nice and reasonable, although overly lecherous, one of the few things Drew disliked about him. Even though William was Andrew's great uncle, he insisted on being called only 'uncle'. It made him feel younger.

Nigel Winston-Phillips was a carbon copy of Andrew. He was also tall, blonde-haired, and handsome. Although Nigel had a sickly fragility to him that Drew didn't have. The boy attributed that to the fact that his father didn't like sports, being more interested in the academic side of things.

"Hey, boy." - Bill greeted him, patting himself on the stomach.

"Hi s-son." - Nigel said nervously. Something was off, Drew felt it in his dad's voice.

"What is going on?" - the blonde teen asked.

"You turned eighteen last week, thus it is time for us to have a discussion." - Dick said cryptically.

"We need to teach you the ways of our family." - Bill explained. Andrew's eyes widened. He heard rumors from his older cousins, but he always dismissed them as silly gossip.

"Please sit, Drew." - his grandfather said lovingly.

Anxious, Andrew took a seat on the empty mahogany armchair.

"Should I be worried?" - the boy asked, visibly nervous. While he loved his family, they intimidated him tremendously, as he was expected to fill their shoes one day. And big shoes they were.

"Do not worry, child. This is part of your duties. The role of being a Winston-Phillips. You need to know, learn, and live our history and our customs if you ever aspire to lead this family." - Dick said seriously.

"Dad, you are putting too much pressure on him..." - Nigel mumbled unhappily. Bill guffawed.

"Hah! It's good for him to learn. He needs to grow a spine. Unlike a certain someone." - Bill smirked, his jab clearly directed at the weak man.

"Come on uncle Bill... not today..." - Nigel muttered, shifting his legs, uncomfortable.

"Hmm... where should we start?" - Dick pondered. "It has been a while since I have done this."

"Brother, just start from the beginning." - Bill said impatiently.

"Does Andrew need to know about all that?" - Nigel asked, gulping.

"Quiet, Nigel." - Bill said dismissively. Andrew was used to the two men dismissing his dad, but he always assumed it was due to his father underperforming at the company and at his duties within the family.

Nigel had an innate knack for messing things up and always preferred to let his wife Jade or his older family members take the lead. He was content enjoying what he had. Of course, the reason why he was like this, was much more wicked than Andrew could even envisage.

"Very well..." - Dick said, clearing his throat and starting to tell the story of the town.

~~~

Reginald Winston-Phillips was 24 years old when he founded a cult on a farm in a small village in the Midwestern United States. He named it the "Cult of Winston", after an old book he had found when he was growing up. Ronald's origins were a mystery, as he changed his name multiple times before settling for Winston-Phillips. and burned any documents that contained information on his birth or real family.

Reginald preached about community and wealth, with a big emphasis on sexuality and sharing between the cult members. Being an extremely good talker, Reginald's following soon grew to dozens of devoted members. He took multiple wives and surrounded himself with highly skilled, albeit naive and easily influenced, individuals. His devotees grew in number and quickly took over the small village. Reginald was elected mayor and renamed the town Winstonstead, the place of origin of his group.

The "Cult of Winston" had an interesting way of viewing the sexuality of its members. Any sexual orientation was welcome in the cult, but nobody could possess another person, everyone was free. Of course, that monogamy was not discouraged, but it had to come from both individuals. If one of the parties wanted to explore or have sexual freedom, the other partner had no say in that. For Reginald, individual sexuality was the most precious and important thing a person had. He also encouraged senior members of the cult to corrupt and help newer members to explore and find their depraved side since Reginald was aware that sometimes people needed a push in the right direction.

Needless to say, Reginald and his followers, were all in favor of Polygamy, Sharing, Swinging, Cuckolding, Fetishes, and any other kind of sexual expression. Reginald's goal was to create a place where certain sexual desires could be explored and enjoyed. Of course, only the ones that fit in the scope of the law were allowed, as he abhorred any kind of dark or evil inclination.

Reginald, his wives, and his followers expanded their small village into a wealthy area, using their skills to trade and transport goods around the region. Their sudden enrichment soon called the attention of local governing authorities. Being a cautious man, Reginald abolished the notion and any mention of a cult and established a company, the Winston-Phillips Co., which took care of the business side of things. This way, they could work with authorities and wet enough hands so that everyone would slowly forget what his town really was.

Most of the detailed information about the origins of Winstonstead was shortly forgotten in the annals of history. Only Reginald's direct descendants kept this knowledge and passed it to each new Winston-Phillips generation.

Nowadays, most outsiders didn't even bat an eye at the small town. Winston was considered a hick place with nothing of interest, besides being the inconspicuous headquarters of a dull company that held a few other subsidiaries around the country. Nothing out of the ordinary.

In his last few years, Reginald created a large book to guide his descendants on the customs and ways of the family. This book served as a base for how Winston-Phillips' family members governed the town and molded its inhabitants. According to Reginald's rules, the size of the community should be no more than 150-200 members, and all of them should work for or around the company/family. Outsiders were not allowed in town (unless invited for important business), and new residents could only be recruited once a year, but only to supplement the population's numbers or the necessary skill set.

~~~

"... I believe that covers our history." - Dick said with a satisfied smile.

"You tell it so well, brother." - Bill said, patting his brother on the back.

Andrew's mouth was agape.

"D-dad... did you... did you know?" - the boy croaked, shocked by his grandfather's story. Nigel nods shakily. "Wow... I had no idea..."

"Drew, I would have let this marinade in your head for a few days, but we have a golden opportunity." - Dick said, nodding to the other adults. Andrew looked confused.

"That's right, boy. We want to talk to you about the sexual side of town." - Bill said. Andrew gulped, he was nervous about this subject matter. "Tomorrow there's a family party. Nigel, why don't you explain to the boy?"

Nigel nodded apprehensively.

"Erm, son... you see... tomorrow you and Chloe are attending the party. And now you are both 18. So that means... erm... there are expectations. You know? Consider what Dad, grandpa, said. People are free here... these things are encouraged. You know? I think you may like it. So tomorrow... you and Chloe can have fun. You both will start to like it. She is a beauty. And you too. Lots of women for you... ermm... I know you don't have experience... but... humm... it's all right. It's just expected..." - Nigel bumbled his way through some sort of nonsensical explanation.

Bill facepalms and Dick laughs at his son.

"God damn it, Nigel, you are useless." - Bill complained. "Listen, boy. What your dad tried to say is that tomorrow your training starts. Chloe's too."

"What does that mean?" - Andrew asked, taken aback by everything.

"Drew. You, as the future of the Winston-Phillips family, are required to serve as an example to the townsfolk. Continue the family's 'traditions'." - Dick explained.

"Does everyone in town know?" - the boy asked, still not wrapping his head around it.

"No, only certain individuals. The others just believe this is part of the culture and they revel in it. Even the women." - Dick elaborates.

"Secretly, everyone wants to be free." - Bill said with a huge grin.

"What if they don't?" - the teen blurted out, more as a reflex than anything else. He was sweating.

"Then, they do not have to. We are not obligating anyone to do anything against their will. People are free here, including to leave the town if they so desire." - Dick said, trying to assure his grandson. To him, his grandchild needed to understand that they were good-hearted and that Winston was a thriving and free place.

Andrew nodded, still unsure about the whole thing.

"But, as Reginald, your great-great-great-great-grandfather, wanted, if one of the sides of the relationship has these desires, they should be permitted to explore." - Bill pointed out.

"What does that mean?" - the boy asked, trying to have a clearer picture.

"That means that, when we identify individuals that have potential, we will try to influence them, so their hidden side comes out. We want everyone to be able to express themselves and be who they truly want and desire to be. Even if deep down." - Bill explained. Nigel gulped and shuffled in place.

"So I don't have to do anything?" - Andrew asked with relief.

"Well, Drew, as a member of this family, certain things are expected of you. So we will give you some time to figure it out." - Dick said fondly to his grandson. He patted him on the head.

"And Chloe?" - the teen asked, looking at his father. His father's eyes widened, and he hastily lowered his head.

"Even your girlfriend. We can tell you all of the details later, but we will not do anything she does not want." - Dick said with a reassuring nod.

"This is just a... small push in the right direction." - Bill added with a hearty chuckle. "You can consider this part of her initiation into the family. Our traditions."

"What if I don't want her to?" - Andrew asked concerned. He knew his girlfriend was strong-willed and started to become more interested in sexual things. He was nervous that she would be open to whatever this was.

"You do not have a say in it. The only person who can decide is Chloe herself. You do not own her. But that also can be said about you. You are the one responsible for your decision." - Dick said.

"So you can choose to be like your dad, or take charge of your own destiny, like us." - Bill added.

"Like d-dad?" - the teen blurted out, staring at his dad who was extremely quiet until now.

"Yes, your dad is weak-willed. He is a cuckold. Right, Nigel?" - Bill chuckled, patting the man on his back.

"Well... I wouldn't say it like that... but..." - Nigel mumbled.

"You are more than happy to see your wife being shared or fooling around with other men while you wank your weenie." - Bill continued.

Nigel shuffled in place, he didn't want his son to see this side of him. Not yet. But at the same time, he knew that he was the one who opted for this path, so he couldn't blame his uncle and father for going into details.

"What?! Mom?!" - Andrew asked, perplexed.

"That's right. Your dad wanted to be monogamous and 'proper'..." - Bill said, making air quotes. "But your mother did not. So after being corrupted by us..." - he pointed between him and his brother. "She loosened up and started to do whatever she wanted. Oh, and loose she is." - he chuckled.

"We do not discriminate here. You can be whatever you want, even a slut or a cuck. You are free to make up your mind." - Dick said to his grandson, sensing his hesitation.

"Of course, being part of the family is a bit trickier." - Bill grinned widely.

The boy looked worriedly between the three adults.

"Dad, is uncle telling the truth? Why did you choose this?" - he asked.

"Tell him, son." - Dick said seriously.

"Erm... well... you see... it's easy that way... and I... gosh... erm..." - Nigel mumbled. He closed his eyes. "I like it!" - he shouted and proceeded to hyperventilate.

An alarm goes off.

~~~

WinstonTV's Saucy Saturdays

"Anyhow, that was enough exposition. Drew, it is time for you to see for yourself." - Dick said.

"What do you mean?" - the teen asked, confused.

"At 9 pm on Saturdays, there is a special program on WinstonTV..." - Bill said. He grabbed the TV remote and turned it on.

Andrew watched Sandy Rivers behind a news desk, talking about the current gas prices or something along those lines.