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Chapter 2
by bingbong123
Whose story do you follow?
Max Keating: A young man faced with the realities of his world
“Max darling, it’s time to wake up,” his father’s delicate voice calls from the bottom of the stairs as the sleeping young man begins to stir. He looks over to his alarm clock and remembers that today begins the last week of his senior year in high school. He groans as he lifts himself out of bed and begins stumbling to the bathroom to get ready for the day.
He shuffles past his twin sister’s door and can hear the distinct sound of heavy metal coming through it. He just smiles and shakes his head wondering how can someone listen to that this early in the morning. Just then his sister throws open the door to her room.
“Good morning little bro!”
“Good morning Alice.”
“Hey Don’t hog the bathroom all morning I need to get ready too.” Max gave a cute little grunt and continued his groggy walk to the bathroom. As he finally reached his destination he looked up and saw his reflection in the mirror and gasped. His normally long brown and well kept hair was strewn all over the place and his face without his makeup was quite a mess. He sighed and started the shower. He began to take of his big girlish t-shirt that he had stolen from his sister and to his horror he realized he didn’t have any panties on. All he could do was hope his sister didn’t notice when he walked by her room.
He sped through the shower and dried his hair and brushed it. He put on his makeup and put his hair in a ponytail, than gave himself a pretty little smile in the mirror and walked back to his room.
Again he passed by his sister’s room and this time kicked on the door. “Hey Alice, you can have the bathroom now.”
“Geez kid I told you not to take long!” She said, teasing him more than anything.
“Sorry.”
“It’s ok I know you boys like to look all nice and pretty,” she said rolling her eyes and giving him a smile. Max’s cheeks flushed and he turned around quick so she wouldn’t see and scurried back to his room. Alice gave a little chuckle and turned to go to the bathroom, her cheeks flushed with color as well.
Max stood, his back pressed against his door breathing heavily trying to calm himself down. He had feelings for his sister but he knew it was wrong and so he kept it bottled inside him. She was his handsome sister and she had always looked out for him. She was the star quarterback of the football team at their high school and was easily the most popular girl in school. However, as this year comes to close the two 18 year old teens we’re going to be separated. Alice had been accepted to one of the best schools in the country if not the world, while Max was going to have his wife selected for him by his mother and that would be his life. Alice had always felt bad for her brothers fate and wish she could do something about it but she knew the rules could not be changed for one little boy.
Max was not very popular but because he was the twin of the most popular girl in school he was well known and people treated him well. He was very pretty with his long brown hair that he almost always put in a ponytail and his big green eyes could make any girl swoon. He wasn’t very tall just 5’ 7” but his legs were long and he had a very good sense of fashion which his mother disapproved of.
He stepped away from his door and began to change into his clothes for school. He put on his short black skirt that rode up pretty high and showed more of his thighs than his mother would like. He than put on his shirt, knee high white socks and sneakers. He also put on his special pink lacy panties that made his tiny little dick feel very special. He smiled to himself and headed downstairs.
“Oh darling you look so pretty!” His dad said as he walked down stairs and into the kitchen.
“Thanks dad.”
“I’m not sure your mother will approve but if you two leave early enough she’ll never know,” he said with a little wink. “You did a much better job on the mascara sweetie.”
“Yeah I tried a little harder today.”
“It looks good Max,” Alice said and gave him a big smile. Max ducked his head and raced to sit at the table, his panties straining from the compliment.
“Thanks,” he said.
“Here you go you two,” their dad said as he set down their breakfast of chocolate chip waffles. The two teens devoured the delicious meal and thanked their father for the meal and got up to head for school.
“Alice why don’t you head to the car I need to talk to your brother for a minute,” he said.
“Okay dad,” Alice said. Max panicked had he noticed his hard on when Alice had complimented him. “See you in a sec Max.”
“Come here son,” his father said and Max walked slowly to his father’s side. His father was very attractive, he kept his long brown hair down around his shoulders and always made sure his makeup was perfect no matter what and wore a long green sundress. His long slender legs came to rest in a pair of very attractive white heels that clicked when he walked. “I want to talk about your future.”
Max gave a verbal sigh of relief but soon realized this could be just as bad. He knew all to well this day was coming when his mother would select a bride for him. “I know dad, I just wish I had more time.”
“I know it can be hard but I’m sure your mother will pick a good fit for you and try to keep your interests in mind,” his dad said with a sad sigh. He himself wished these old ways would be abandoned but it was still the norm even in this day and age. “Well since you know what’s going on I won’t keep you from school have a good day hun. Now get going before your mother wakes up and sees you in that skirt!”
Max quickly made his way to the garage and into the car with his sister.
“What was that about?” Asked his sister.
“Nothing.”
“Ok, but you know you can tell me anything,” she said and looked down on her cute little brother with a smile. Max blushed and shifted in his seat and suddenly felt very uncomfortable.
“Thanks Al,”he said trying to contain his dark fantasies. They lived very close to school only three minutes away and they rode the rest of the way in silence, Max trying desperately to make his hard on go away.
“Hey can I show Riley your drawings?” His sister asked. Max’s eyes went as wide as they could go and stared down at his seat nervously twiddling his fingers. If there was one person who Max liked more that his sister was her best friend Riley. She was just as handsome as his sister, just as muscular and strong but she was much taller and more charismatic.
“Umm-” Max started.
“Great!” She said cutting him off. “I’ll just show her this.” She held up his little black sketchbook where he sketched everything he saw of interest and was very private.
“Where did you get that?!”
“I found it in you backpack while you were talking to dad.”
“Alice!”
“Oh shush, I saw the picture you drew of her. It’s very flattering.”
“No Alice that’s private! Please!”
“You’re so talented Maxy and I’m gonna show you off,” she said as they pulled into the parking lot at school. “Now run along and I’ll see you later today.” She gave him a kiss on the cheek and Max grabbed his backpack and started walking towards school his hips swaying sexily as he walked. What he didn’t know was she also saw the many drawings of herself. She picked up her phone and texted Riley to meet her at the basketball courts.
Max walked into his first class which was his favorite. Mr. Gerard’s advanced art class was always the highlight of his day. Although it was at the beginning of the day he loved drawing and painting and was very good at it. His best friend Jack was also in it which only made it it better. Jack wasn’t very pretty but he’s had been Max’s friend since they were little kids. He was kind of chubby and had a very poor sense of fashion.
Mr. Gerard however was absolutely stunning! Fresh out of college he always wore a cute little sundress and a pair of short heels. His long blonde hair flowed with grace over his slender shoulders. All the girls tried to get into his class but most of them were not cut out for the advanced art class.
“Ok everyone today we start the final project,” Mr. Gerard said with a smile. “We are gonna do portraits so everyone pair up and we will get started. Just then Max walked into the class breathing heavily. “Nice of you to join us Mr. Keating please have a seat we are doing portraits.”
Max sat down at his assigned seat and noticed his best friend was absent. He noticed everyone had partnered up with someone except him.
“Max come here please,” his teacher said in his distinct high voice. Max got up and made his way to his teachers desk his sneakers squeaking as he walked. “Now I know Jack isn’t here today, I was told his mother has arranged a bride for him and he’s meeting her today.” Max was stunned! How did Jack get a bride before him? Not that he wasn’t happy for his friend just taken by surprise. “With that I will be your partner for your final project and you can paint me.” Max was once again left in silence. He was going to have to paint his teacher? His teacher leaned in close and said, “now your easily the most talented in this class so I’m glad it’s you painting me. So grab your things and come sit by at my desk.”
The rest of the class went by quickly and the two talked the entire time and Max got quite a bit done with his painting. Just as soon as the class started it was over and the bell rang letting everyone know it was a time to change classes.
“Okay everyone have a good day and I’ll see you tomorrow,” his teacher said with a smile. “Max can I talk to you for a second please.” Max stayed behind while the class filed out. “Now I know you have a real passion for this and you’re so talented I would hate to see your life wasted as some househusband for an ungrateful wife.” Max let out a sharp gasp, he had never heard his teacher talk like this before or any man for that matter.
“I uh-” max started.
“I know it’s a hard thing to hear and especially when you’re so pretty, I’m sure your mother already has several prospects for you to choose from.”
“Mr. Gerard I don’t know what you want from me.”
“Go to school Max! Become an artist don’t live under this shadow.” He put his hand on his shoulder and got real close. “You could be famous you have so much talent!” Max didn’t know what to say and his mouth just stayed open, he had no idea how to respond to that. “Just think about it ok. I can right a good letter of recommendation for you. And here you’re gonna need this for your next class.” Mr. Gerard handed him a pass that would let his next teacher know that he was talking to him. “Just think about it ok.” He smiled as Max turned around and started to walk towards his next class.
The rest of the day was a blur, the classes slipped by and he hardly said a word to anyone. The word of his art teacher echoing in his head. He pulled out his phone and texted his sister wondering if he could get his sketchbook back.
Sure! Meet us by the basketball courts.
As the last bell of the day rang he started making his way to the basketball courts. He couldn’t keep the words of his teacher out of his head. College? He couldn’t go to college that was for girls and rich boys he thought.
He saw his sister with her back turned to him with her group of jock friends. She would would know what to say right? He wasn’t sure he should tell her he wouldn’t know how she would react. As he got closer he saw Riley was with them and she saw him and her handsome face gave him a smile. Max blushed and walked a little faster his ponytail swaying with each step.
He stood right by his sister and he looked up at her. “Hey Ali-” he started.
“Get off me slut!” Alice shouted and threw her arm back never turning around and hitting Max in the face. Although it wasn’t a hard hit it was enough for Max to lose his footing and he tripped and fell. His butt landed on the hard tile with a slap. When he fell his skirt lifted up exposing his frilly pink panties and his tiny penis to his sister’s friends.
Riley looked at him with her mouth wide open in shock. “Alice! That was your brother!”
Alice turned around and with horror filled eyes looked down at her brother. With tears falling from his eyes he stood up fast and started running away.
“Max wait!” Alice yelled. “Oh my goddess what have I done!”
Max’s Mother
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The Fairer Sex
A world of strict gender roles, reversed
Explore a world where the roles of each gender are still strictly enforced though societal and social pressures, only they are the opposites of those we know. Women are expected to take the lead in almost every situation, with the men in their lives as meek followers, and scorn and mockery awaits anyone who steps outside these boundaries of good behavior. This is clearest of course in the world of romance.
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- Mother, Mother-son, Discipline, Bondage, Spanking, Femdom, Training, Alternate Universe, Gender Role Swap, Crossdressing, Personality Change, threesome, femboy, Proposal, Romance, Pussyjob, Humping, Female Supremacy, Male Sub, Gender Roles, Marriage, Cuckquean, Pegging, Love, Cum eating, spank, pretend couple, interracial, Outercourse, mommy, CFNM, Nursing Handjob, Gentle Femdom, Wife, Boobs, Handjob, father, daughter, panty sniffing, Striptease, Punishment, Fdom, Domestic Discipline, Comfort, Tears, Househusband, 1950s, Mommydomme, MILF, Doctor, Nudity, Choosing, Older Sister, Amazon Position, Riding, Rough, Muscles, Amazon, Workplace, Stripping, Domination
Updated on Jun 13, 2025
by Conan The Librarian
Created on Aug 13, 2020
by Haoro
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