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Chapter 5
by bingbong123
The next day
The dream
Max woke up with a groan. He had the best dream of his life. It was so strange it felt so real like Alice had actually done those things with him. He started to think maybe she felt the same way about him. But he pushed those thoughts from his mind, he knew his sister could have any boy she wanted she wouldn’t choose him.
He started to get out of his bed but noticed this strange crust that was all over his body and the smell was over powering. It made his tiny cock ache. He managed to pull himself out of bed and he opened his door and made his way to the bathroom. As he walked by his sister’s door it opened with a whoosh and she stood there already dressed for the day looking so handsome.
“Hey Max, you look cute,” she said with a smile that was a little to mischievous.
“Good morning Al and thanks. How did you sleep?”
“I didn’t really, I had some things on my mind.”
“Oh, I’m sorry,” Max said and turned for the bathroom.
“Dad said you didn’t have to go to school today.”
“Really? Ok thanks for letting me know.” Alice returned to her room and continued to get ready for school. Max reached the bathroom and stepped inside, took one look at the mirror and nearly screamed. What was all over him he thought. It was all over his shirt, which was actually his sister’s and covered his face and was sticking to his hair like glue. He didn’t know what it was or how it got there but he knew he needed to get it off. Whatever it was mommy would disapprove.
He started the shower and washed himself until all of the mystery substance was off of him. He got out of the shower dried his hair and put it into his signature ponytail and did his makeup. Much better he thought to himself. He wrapped his towel around him and opened the door. He stepped out and ran right into his sister who was waiting on the other side. As he fell his sister tried to grab him but only succeeded in grabbing the towel concealing his most private parts. When he hit the ground his chest and small boyhood were revealed, much to his sister’s delight and his horror.
“Max I uh-”
“Don’t look Alice please! Just give me my towel.”
“Ok ok here,” she said and handed him his towel and he quickly covered up and scurried off to his room and slammed the door shut.
“Fuck” he said to himself as leaned against the bedroom door. Unable to get the look of his sister’s face out of his mind. It looked like pure lust and desire. Maybe that wasn’t a dream maybe she did come to his room last night.
“Bye Maxy I’m off to school,” she said but Max didn’t respond he was still in shock.
He decided since he didn’t have to go to school he would sit in his room and draw all day. Avoiding any confrontations with his mother. As the hours slipped by he found himself only thinking of his sister and what he wanted her to do him. It made his cock throb just thinking about her. But as he was reaching down to pull his cock out he got a text from Riley.
Hey hope you’re feeling ok. Your sister said you were sick. I hope I didn’t scare you off I really enjoyed our conversation last night.
Max quickly answered back,
No of course not I did too! I was just feeling under the weather today that’s all.
Ok well I was wondering if you wanted to got the movies with me on Friday?
What the movies? With Riley? He couldn’t believe it! Arguably the most popular girl in school wanted to take him out to the movies.
Ok sounds like fun!
Great I’ll pick you up at 6!
He couldn’t believe it. He didn’t know if his mother would approve but he would cross that bridge when he got there he thought to himself. He continue mdr to draw with a huge smile on his face thinking of his date on Friday.
Just then a knock came on his door, “Max come down and talk to me please, I’ll be in my office.” His mother’s voice was like a wake up call to the fantasy he was thinking about.
“Shit,” he said out loud and got up from his desk. He made his way downstairs and saw someone’s brief case that was not his mother’s and as he made his way to his mother’s office he could hear faint voices coming from inside.
“He’s a good boy he’s just trying to find himself right now. You know how boys get with their emotions and everything.” He could clearly make out his mother’s voice but he didn’t recognize the second.
“I understand I want to get to know him, to find who he wants to be.” Max knew this day was coming and that’s probably why he got to stay home from school.
“Those are dangerous words Erica, boys shouldn’t be given that much room they need to be loved yes, but they also need authority.”
“I disagree, but I don’t think we are alone anymore.” Max froze, they knew he was standing outside the door listening.
“Max please come in here,” his mom said. He slowly opened the door and peeked his head through and then stepped in the rest of the way. What he saw before him blew him away. She was the most handsome woman he had ever seen. She was tall and muscular and her face looked like it had been chiseled by the goddesses themselves. Her hair was blonde and short and she had a pair of thin transparent glasses on. She wore a suit and tie and looked very important. “What are you wearing?!” His mother yelled at him.
“Now, Sarah it’s ok he didn’t know I was coming it perfectly alright.” Max looked down and saw his mother was right, he wore a pink tank top that showed off his cute little tummy and a pair of white Cotten panties with little bunnies on them. He didn’t even realize he was dressed so inappropriately until his mother yelled. He was to caught up with thinking about his date with Riley.
“Nonsense! Go to your room and change this instant young man!”
“I’m so sorry ma’am,” Max said and started to walked back to his room to change.
“Max, right? It’s ok really I don’t mind you look rather nice.” She said and gave him a warm smile that made his cheeks flush. “Can I take you out to lunch?”
“Today? As in right now?” Max asked.
“Yes.” She said with a warm smile.
“Umm-yeah I uh-” Max started.
“No not right now he needs to be punished for looking like this in front of you it is embarrassing!” His mom yelled at him.
“Hush Sarah! He couldn’t have possibly known you didn’t say anything to him about me.”
“Yes well, he should’ve dressed more appropriately even if he was just talking to me.” My mom said with a huff. The tall handsome lady came up to Max and put her hand on his shoulder and looked into his eyes.
“It’s ok sweetie, we are gonna grab lunch ok.” She said with kindest smile you could imagine. All Max could do was nod with his mouth wide open in amazement. No one had ever talked to his mom that way. “But we’re going to go to a place that requires a little more clothing.” She said with a small laugh that made Max smile.
“I’ll uh-I’m going to uh-” he couldn’t finish his sentence. She was to perfect for him.
“Ok sweetie I’ll wait down here.” She said and stepped back from him. As Max walked back to his room he could here the two woman discuss him but he didn’t care he was to focused on looking perfect for her.
He got to his room and picked out a dress that went just above his knees. It was tight to make sure whoever was watching him could admire his hour glass shaped body. It was black with a white bow at the waist. He had bought it for himself but never really planned on wearing it, it was the type of dress you would wear to a very fancy party. He also grabbed a pair of black 6 inch heels and went to the bathroom. He took out his ponytail and let his hair flow down his shoulders. He did a little fixing of his makeup and tried to curl his hair to make it look as sexy as possible. He looked in the mirror and frowned he just looked like stupid high school boy, not a man of class this woman was obviously used to.
He couldn’t do any better with the time he had though and opened the door and made his way downstairs. As he was walking back to his mother’s office his sister walked through the garage door and nearly fell over when she saw him.
“Max? Is that you? My goddess you look beautiful!”
“Thanks Al,” he said with a blush and walked up to her and gave her a kiss on the cheek. “I love you so much.” He said to her as he pulled away. He started walking again but his sister grabbed his arm and pulled him back.
She shoved him against the wall of the hallway and look deep into his eyes. “Alice please your hurting me.” She didn’t realize she was holding him up, his feet were off the ground and he looked scared.
“I love you too,” she whispered into his ear and then kissed him on the lips. Max was in shock he couldn’t register what was going on. Then he felt her tongue pushing against his lips. But he didn’t fight it, he opened his mouth and her tongue began to furiously flicker against his own. He didn’t know what to do he had never been with anyone before, he just stood there being held up by sister in complete awe.
Then she reached under his very fancy dress and she found his most private place and squeezed. Max buckled and shuddered unable to control himself. He felt it coming just as when his mother had spanked him. He began to shake and convulse. His sister pulled away, not really sure what to do.
“Max?! I’m sorry are you ok?”
“Ieeeeeeereeeeeeeeeeeeeeee,” he let out a high pitched squeal and fell to his knees and Alice could see the white liquid start to puddle underneath him.
“Oh my goddess Max! You’re so sexy when you cum baby! And you cum so much every time!” Max couldn’t really process what she was saying he just sat there with his tongue out and panting like a dog in heat with a pool of his spunk around him. “Here stand up, take these and use the bathroom down here to clean yourself up. Luckily it didn’t get on your dress. Fuck baby you’re so sexy I can’t take it.” As she was saying these things to him she shoved a pair of his panties into his hands which she had obviously stolen and brought him to his feet and shoved him in the downstairs bathroom.
Max stood there looking at himself with a pair of panties in his hand that his sister had stolen from him and cum still dribbling to the floor.
The Date
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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.
- Tags
- 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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