Chapter 63: Herby and Then a Scary Saturday

Madison handed the late note to her teacher and took her seat. She looked up and saw the teacher looking at her with suspicion. Did she suspect what she was doing? She looked around and saw a lot of the kids looking at her. She sighed and opened her notebook to give the impression she was paying attention.

The bell rang and she wandered to fifth period. She started to think about her date later. What would the son look like? She was pretty sure he wasn’t going to be a stud, or his daddy wouldn’t have to pay a girl to spend time with him. Paid? She was being paid to go on a date. That still seemed strange to her. She understood the money they gave her for posing, even though she knew the increase had nothing to do with her posing. She wondered if she was obsessing far too much about this, it was just a date and even if she had to have sex with him it’s not like that is anything new, she already screwed his dad. The bell rescued her from her straying thoughts, and she packed up her things.

She looked at the clock and it was 3:05, she had 40 minutes before she was going to be picked up. She walked towards the back door of the school and pushed it to go out into the fresh air. She saw a few kids hanging around in the middle of the track. She turned and headed for the side of the school. She went around the building and then walked into the open spot she was familiar with. She sat down next to Shelly and the girl smiled at her.

“Hey pretty girl, you look amazing in that dress. I never knew how much hair you had, it’s awesome.” Shelly said and ran her fingers through her long hair.

“Thanks. I thought I would wear it down today to be different.” Madison said.

“Shit, do this more often, it’s beautiful.” Shelly said and Madison giggled.

“Where’s the rest of the guys?” Madison said.

“Johnny’s in detention again, he pretty much lives there. Jimmy and Marge usually don’t hang on Fridays.” Shelly said.

“Why do you hang on Fridays?” Madison said.

“Baby, anything I can do to stay away from my house works for me. I only have two more weeks and then I will be eighteen and I can tell him to shove it. I have a little saved up and I want to eventually get a place of my own.” She said and Madison frowned.

“He’s that bad?” Madison said, remembering Sam’s daddy.

“Sometimes he is. The problem is you don’t know when those times are. My mom is almost fed up, but she is hanging on, mainly because she has nowhere else to go and I have a little brother that is still stuck in that shithole. He doesn’t have it as bad as me; he doesn’t have tits.” Shelly said.

“I’m sorry.” Madison said.

“Thank you, baby, but I will be ok. He only grabs my tits occasionally now when he’s really drunk. He still remembers the kick in the nuts the last time he grabbed my ass.” Shelly said.

“You’re kind of a badass.” Madison said and Shelly giggled.

“Yeah, all 5 foot and 100 pounds of badass.” Shelly said.

“You control Johnny pretty well.” Madison said.

“Not well enough, he took advantage of you twice.” Shelly said.

“That’s ok, I don’t mind doing that.” Madison said and Shelly sighed.

“A 14 yr-old should not be ok with sucking cock.” Shelly said.

“Why not?” Madison said. Shelly put her hand on her arm and rubbed it.

“Baby girl, what happened to you?” Shelly said.

“Not sure, the man that paid for my virginity did end up raping me along with all his friends.” Madison said.

“Yeah, I heard about that. How do you feel about that?” Shelly said. Madison sighed.

“You know, everyone thinks I am messed up because of that but I have come to terms with it. The worst one is dead, and the rest are in jail. I really don’t think about it much anymore. It was horrible but it’s over.” Madison said.

“That’s good. One of them is dead?” Shelly said and Madison nodded.

“Yeah, he committed suicide.” Madison said.

“Wow, I’m not sure what to say about that.” Shelly said. Madison looked at her phone.

“I have to go in a few minutes. I have a date tonight.” Madison said and Shelly smiled.

“That’s cool, good for you. What are your plans for the weekend?” Shelly said.

“I’m not sure. What are you doing?” Madison said.

“I have to work all weekend, one of the other waitresses is sick and I have to work doubles.” Shelly said and groaned.

“You’re a waitress?” Madison said and Shelly nodded.

“Yeah, the diner over on Fourth. The tips are good, at least I get paid for people grabbing my ass.” Shelly said and Madison laughed.

Madison picked up her backpack and looked down at Shelly. The girl stood up and hugged Madison.

“I’m going to hang out here until Johnny gets here.” Shelly said and Madison smiled.

“Need to feel some vibrations?” Madison said and Shelly laughed.

“Yeah, I don’t work until 7 so I usually go straight to work from here. He fills the time.” Shelly said.

“I will see you on Monday. Have a good weekend.” Madison said and hugged her.

“You too princess, have fun on your date.” Shelly said.

Madison walked out and around the school to the parking lot. It was only 3:40 but the big black car was sitting on the far side of the lot near the road. She walked over to it and the driver’s window lowered. There was a large white man with a big moustache and a black hat.

“Madison?” He said in a deep voice. She nodded.

“Get in the back.” He said and moved his head towards the back of the car.

She walked back and opened the door. The inside was big, there was a long back seat and a smaller seat facing her with what looked like a bar or something next to it. She felt really small in the back seat by herself as the car started moving. This car was much bigger than Aaron’s, she looked out the window and thought about him. She missed him, the last time she saw him she slammed the car door while he was talking. She knew she was mad, but she honestly didn’t remember why. She sighed and wondered if he would be disappointed in her too since she was pregnant now? She lost herself in thought and then the car stopped in front of a huge house. The door opened and the moustache man was looking at her.

“They are expecting you.” He said in his deep voice. It almost sounded like he was forcing his voice to be so deep, but she immediately realized that was stupid. It just sounded so strange.

Madison slipped out of the car and walked to the door. She saw the doorbell and hit the button. The door opened after a few seconds and Anthony was standing there. His tie was loose, and his white shirt was untucked. He had a beer in his hand.

“Madison, nice to see you again. Come in.” he said. She walked into a huge room with a fancy staircase to the left and an even bigger room to the right.

“Let me take your bag.” He said and he took her backpack off and hung it on a hook on the wall to her right.

“Herby is in his room. Do you want anything to drink?” He said and she felt incredibly thirsty suddenly.

“Water would be good.” She said and followed him into a massive white kitchen. She looked all around and was amazed at how big and clean everything was. He held out a water bottle.

“Thanks.” She said and opened the bottle and took a huge drink. She put the bottle down and realized he was staring at her.

“Fuck, you are so pretty. That hair is dramatic.” He said and she smiled.

“Thanks.” She said, unsure of what she was supposed to do next.

“Come on, I’ll introduce you to Herby.” He said and walked toward the stairs.

She followed him up, holding the railing and looking at all the art hanging on the walls. The top of the stairs opened to a balcony looking over the bigger room. It made the house seem even bigger. They walked down a hallway, and he went into a room. She saw a boy sitting with headphones on and typing on a keyboard in front of a huge monitor. He walked up and touched the boy’s shoulder. The boy hit a button and took off his headphones.

“Hey dad, what’s up?” He said.

“Madison is here.” Anthony said and the boy looked but he couldn’t see her behind Anthony. Anthony moved a little to the left and the boy looked at her.

“Herby, this is Madison.” Anthony said and the boy just stared at her. Anthony hit him on the shoulder lightly.

“Oh, sorry, nice to meet you.” The boy said in a nervous voice.

“Nice to meet you, Herby.” She said and held out her hand. He took her hand, and his hand was cold and a little wet. She shook it and tried to keep a smile.

She looked at the boy and the first thing she saw was his wild hair. It was dark and looked like he had been in the wind for an hour. He wore glasses with dark frames that he pushed up on his nose. His eyes were brown and kinda pretty, but his face was a little chubby.

“Dinner reservations are for 7:00. Bruce will take you; you should leave around 6:45.” Anthony said and the boy nodded.

“Ok, thanks Dad. Where?” Herby said.

“I got you a table at Frenchy’s.” Anthony said and the boy frowned.

“Ok.” He said.

“You will be fine; Marco is expecting you. Don’t lose track of time.” Anthony said and left the room.

Madison looked at the boy now and his arms were a little chubby as well, she couldn’t see much else with him sitting down but he looked big like his dad, just a little smaller version. He was still looking at her and she felt a little nervous.

“Do you not like that restaurant?” She said, trying to make conversation. He shook his head like she had broken him out of a trance.

“No, it’s ok, it’s just where all the snobs hang out. I don’t like going without my parents, not really my scene.” He said and she chuckled.

“I get it.” She said.

“You look like a witch.” He said.

“Sorry.” She said, not really understanding what he meant.

“No, it’s cool. How old are you?” He said.

“14.” She said and he looked stunned.

“Really? You look older.” He said and she smiled.

“Thanks, how old are you?” She said.

“16, I’m a junior, do you go to my school?” he said and she shook her head.

“No.” She said and he nodded.

“What do you want to do?” He said. She looked at his screen and it looked like stuff was still happening.

“What are you doing?” She said and he looked back at the screen.

“Playing a game. It’s called Wizard’s Quest; we just got it last week.” He said.

“We?” She said and he pointed to a window with two names in it. Ballbuster and Fireball.

“My friends, we can play together.” He said and she nodded.

“Ballbuster?” She said and smiled.

“Yeah, that is Mitch, he’s our fighter. Sorry about the name.” He said.

“Ok, so Fireball is your fireman?” She said and he laughed.

“No, he’s our mage.” He said and she smirked.

“Wait, you knew that didn’t you?” He said and she nodded.

“Sorry, I was teasing you.” She said.

“No, it’s ok, I’m not really good at picking up on stuff like that. You’re very pretty.” He said and she giggled.

“Thank you, Herby, can I play?” She said and he looked stunned again.

“You want to play?” He said, sounding very confused.

“Sure, it looks like fun.” She said. He looked nervous but he grabbed a second set of headphones and held them out to her. She pulled a chair over and sat next to him.

“We’ll have to create a character for you. What do you want to be?” He said. She looked at the screen and saw the pictures of the two other characters. She didn’t really know much about types of characters, so she said the first thing that came to mind.

“Well, I guess a witch, can I be that?” She said and he smiled.

“Yep, we need some more healing. Do you want to be a witch with healing powers?” he said and she nodded.

“Sounds good.” She said.

“Ok, cool. We have to design what you look like.” He said and hit a button. She saw a girl character standing on the screen wearing what looked like a small black bikini. She had short blonde hair, and she was tall.

“Can I have some clothes?” She said and he laughed.

“Sure, what do you want?” He said. She looked at the other two again and then at his picture, he looked like a knight with armor and a big sword.

“What are you?” She said and pointed to his picture.

“I’m a paladin. Sort of a cross between a fighter and a priest.” He said and she nodded.

“Ok, can I just look like me?” She said and he looked at her.

“That would be really cool, stand up.” He said and she stood and twirled a little, making her skirt and her hair flow around her.

“You are so pretty.” He said and then started moving the mouse and hitting buttons.

She saw her picture suddenly get shorter and then the hair changed to dark and got longer. He clicked again and she was wearing a black robe that went to her knees. Black boots popped on her feet, and she snickered when she looked down at her sneakers.

“Sorry, I like boots on girls. Do you want me to change them?” he said.

“No, they look cool.” She said and then she was holding a large stick.

“What is that, I thought I would have a magic wand or something?” she said and he laughed.

“No, you don’t need a wand. That is a Bo, we can give you some points in that, so can you use it to fight.” He said.

“I have to fight?” She said.

“Sometimes we run into monsters that are immune to magic and we have to fight them. Me and Ballbuster will do most of the fighting, but you may have to defend yourself.” He said and she nodded.

She watched him as he typed, he already looked cuter. He was excited and that made him seem more attractive for some reason. He finished, pushed his glasses up, and looked at her. She saw her picture and it sort of looked like her, her figure was moving slowly back and forth, and her robe was swirling along with her hair.

“That’s amazing.” She said and sat down.

“Thanks, let’s get started, put your headphones on, the mic is on the left. He held out a little black box. This is your controller, it’s pretty self-explanatory, move the little stick in the middle to go that direction. If you want to cast a spell hit the red button, if you want to fight hit the blue button. I’ll help you if you get in trouble.” He said and handed it to her.

She watched him hit a few more buttons and the screen changed and started moving. It looked like a big field with a lot of trees and bushes. She saw what looked like a broken-down shack in the distance.

“Fellas, we have another player.” He said and looked at her. He covered his mic with his hand.

“What do you want your name to be?” He said. She tried to think of a cool name like theirs, but her mind froze.

“Can I just be Madison?” she said and he nodded.

“Guys, her name is Madison, and she’s a witch.” He said and she heard some voices in her headphones.

“Nice character, you fantasizing again buddy?” She heard a voice.

“Yeah, you know me.” He said and smiled at her.

“She’s hot, it will be nice to have some eye candy around.” She heard another voice.

“That’s what I was thinking.” He said and she heard laughter.

“Their real names are Mitch and Wendell.” He said.

“Oh, I was hoping I could call them Ballbuster and Fireball.” She said and she heard silence. She looked at Herby and he was smiling.

“Wait, it’s really a girl? Holy shit dude.” She heard a voice and she chuckled.

“Yes, it’s really a girl. Her name is really Madison so be nice.” Herby said.

“Now that wouldn’t be any fun.” A different voice.

“Don’t play any different just because I’m a girl.” She said.

“Cool, then let’s go. I have wanted to see what’s in this house for a while. Madison, take a spot behind me and in front of Fireball.” She heard a voice and moved her character.

Anthony sat in his chair and thought about the little cutie upstairs. He closed his eyes and remembered her hot little body bouncing on his cock and those fucking tits bouncing in front of his eyes. He rubbed his hardening cock and tried not to just walk upstairs and fuck her in the bathroom. She was so hot yet so innocent looking, he figured that’s what made her so irresistible. He grabbed the remote and tried to find a show to take his mind off those little titties and that perfect ass. He heard the front door open, and he looked over.

“Anthony, can you have Bruce get my packages out of the car?” He heard.

“Yes, dear. Did you have fun shopping?” he said and took a drink.

“It was ok, my favorite store was closed.” She said.

“Horrible, that is a tragedy.” He said and laughed.

“Fuck you, Anthony. Where’s Herby?” She said.

“He’s upstairs with his date.” He said.

“Oh, that’s right. She’s here. I need to go meet her.” She said.

“Missy, leave them alone. Let them spend some time, God knows he needs to spend more time around girls.” Anthony said.

“Fine, what time is their reservation?” Missy said.

“7:00, Bruce is taking them at 6:45.” Anthony said.

“Ok, I will just go and remind them of the time.” Missy said and headed for the stairs.

“Missy, do not embarrass him.” Anthony yelled.

“Quick, close the door!” Madison screamed and Herby hit a button.

“Good catch, what the fuck was that?” Fireball said.

“I don’t know, it was black and fuzzy.” Madison said and Herby laughed. She looked at him.

“No, I’m not laughing at you. It’s nice to have someone that says stuff like that.” He said and she smiled.

“It was black and fuzzy.” Ballbuster said and Madison giggled.

“Thank you, kind sir. Now, should we kick its ass or make it our pet?” Madison said. She heard laughter.

“I love this girl. Herby, I don’t ever want to see a picture of her, I just want to imagine her as I see her on the screen.” Ballbuster said and Madison snickered. She looked at Herby and winked. He smiled.

“No, I’m sorry. I didn’t mean anything at all. Shit, I shouldn’t have said that out loud.” Ballbuster.

“It’s ok, I’m confident about my looks but you can think of me like what you see.” Madison said and winked at Herby again. He snickered.

“Ok, I’m really sorry. Sometimes I just say stuff without thinking.” Ballbuster said.

“It’s ok. Enough of that, dead meat or a leash?” Madison said.

“I vote dead meat; pets are an annoyance.” Fireball said.

“You just want to cast incinerate. How about we open the door slowly and see how it reacts?” Herby said.

“You have my vote, great leader. Sounds like a plan, but if it makes a move towards any of us it’s toast.” Fireball said.

“My hero.” Madison said. She heard more laughter.

“Herby, introduce me.” Madison heard a voice and turned to see a woman with big blonde hair and a lot of jewelry.

“Mom, we’re in the middle of an encounter.” Herby whined.

“Well pause it.” The lady said. Herby hit a button and groaned.

“Fine, Mom, this is Madison. Madison, my mom.” He said. The lady laughed and walked up to her.

“You are adorable.” The lady said and picked up a handful of her hair.

“Mom, she’s not a puppy.” Herby said.

“Oh stop. Honey, your hair is gorgeous, and you are cute as a button.” The lady said.

“Thank you.” Madison said.

“Herby, where are you going for dinner?” The lady said.

“Frenchy’s.” Herby said as he was looking at the screen and typing.

“Oh wow, darling you have to let me help you. Frenchy’s is very exclusive, you are pretty, but I can help make you stunning. Stunning fits in much better than pretty at Frenchy’s.” She said and Madison looked at Herby. He frowned.

“Might as well humor her, she will harass you until you agree.” Herby said and Madison looked at the lady. The lady clapped her hands and hopped.

“Goodie, this will be fun. I will come to get you at 6:15, that should give us enough time. I will go pick some things out.” She said and left the room.

“Sorry about that, she’s a lot.” Herby said.

“It’s ok, she’s just excited. Does she do that with all your dates?” Madison said and Herby got a weird expression on his face. He turned back to the screen.

“Yeah.” He said and she reached over and touched his arm.

“Herby, I’m sorry. I just assumed as cute are you are that you had a lot of dates.” She said and she saw the light come back into his eyes. He nodded and smiled.

“Dead meat or pet?” he said and she laughed. He hit a button, and she heard the guys again.

“Sorry about that guys, we had to fight off an attack from the momster.” Herby said.

“Dude, sorry. Madison, did you use your Bo?” Ballbuster said.

“Yep, knocked her right down the stairs. Now, can we open this damn door already, the thing might have had offspring by now.” She said and she heard laughter.

Madison spent the next hour casting healing and fighting off a small pack of dogs that tried to attack them as she was trying to heal Ballbuster and Herby after they got jumped by a baby dragon. She and Fireball protected them through two more attacks, and she was having a ball. They healed and found a buried staircase that was creepy and dark, but it ended with a ghost guarding a chest that Ballbuster sent back to heaven with his sword. She got some potions and a lot of nice bling. Her character now had a sweet gold necklace of protection that looked awesome with the dark robe. The door opened and they both looked up.

“6:15, honey, you ready for a makeover?” Missy said and Herby groaned.

“Mom, really?” Herby said.

“Quit your whining, you need to take a shower anyway and put on some nicer clothes.” Missy said and grabbed Madison’s hand.

“Sorry.” Herby said and Madison smiled.

Missy drug her down the hall and into a bedroom. Madison saw a dress on the bed. It was gold and sparkly with small spaghetti straps. She looked at the lady.

“My daughter is off at college, and she was about your size. She never got rid of anything; I think she wore this once. Have a seat, let’s get started.” Missy said and sat Madison in a chair in front of a mirror. Missy got behind her and lifted her hair.

Madison sat as Missy brushed her hair and then curled it. She pulled some of it up in a bun on her head but left quite a bit hanging loose. It looked like a professional hairdo. Madison smiled and then Missy started on the makeup. She sat and watched her face take on a different look. She put on light gold eye shadow to match the dress. She put on mascara and light pink lipstick. She put a little rouge on her cheeks and then stepped back. Madison loved the way she looked. She looked up at the lady.

“Thank you.” She said softly.

“Baby, it was like working with a masterpiece from the start.” Missy said and Madison loved hearing words like that.

“Let’s see how this dress fits. Take everything off.” Missy said and helped her stand.

Missy unbuttoned her black dress and then pulled it over her head. She folded it and placed it on the bed. She pulled off her bra and slipped her panties down her legs. She was left in just her shoes and socks.

“Your body is remarkable. Just precious.” Missy said and touched her breast. Madison flinched.

“Sorry baby, I couldn’t resist. They are beautiful.” Missy said and ran her finger over a small nipple. She pulled her hand back and shook her head.

“Ok, while those sneakers are very cute, they won’t fly at Frenchy’s. Have a seat.” Missy said and sat Madison on the bed.

Missy knelt and started taking off her shoes. Madison saw her eyes move to her pussy a few times and she felt a tingle. Would she be out of control with older ladies as well? She took a deep breath and the lady finished taking off her socks.

“Ok, stand up, let see how this is going to work.” Missy said and Madison stood.

She picked up the gold dress and slipped it over her head. She pulled it down over her body and straightened it. It was tight but not uncomfortable at all. It came to the middle of her thighs, but it didn’t look slutty short. The lady started fussing with the top.

“Baby girl, I will deny saying this, but this looks better on you than it did on my daughter. These little beauties fill out this top perfectly.” Missy said and ran her finger over the top of the dress, touching the cleavage above the dress.

The lady pulled her over and she looked in the mirror. She did love the dress; the overall look was very nice. She looked like she was going to a dance but maybe these people looked like this all the time. She wanted to take a picture and send it to Sam. She thought about Sam and remembered she wanted to talk to her. She would have to try and call her again.

“It looks awesome, thank you so much.” Madison said.

“Not done yet. Have a seat and put the panties back on.” Missy said.

Madison sat down and picked up her panties. Missy walked out and came back in a minute with a pair of black heels. She knelt and slipped them on Madison’s feet. They were closed toe with two straps going over her foot. They looked very fancy, her other heels had more of a slutty look, but they came from Barr so yeah. She stood and moved her feet around. They were gorgeous. The lady was sitting back on her feet and smiling.

“It’s like having my very own dressup doll. You are beautiful little one.” Missy said and Madison smiled.

The lady stood and took Madison’s hand. She walked her out and then to the top of the stairs. She moved some hair around and rubbed her finger on her cheek a little.

“Perfect, you will wow them at Frenchy’s.” Missy said.

They walked down the stairs and she saw Herby standing next to his dad looking very uncomfortable in a jacket and pants. His hair looked like he ran a wet brush through it once after he got out of the windstorm. He looked up and she saw his eyes open wide and she smiled. His mouth was hanging open and she walked over to him. He looked stunned.

“Wow, Missy.” Anthony said.

“I know, isn’t she gorgeous?” Missy said.

“Yeah.” Anthony said and had to admit she might look better now than she did naked sitting on his cock. He turned to the side to hide his erection.

“Herby, take your lady to dinner.” Missy said and lifted his arm. Herby looked at his mom and Madison slipped her arm over his. He looked at her and she smiled.

“Let’s go see what this place is like, my spells are all charged up.” Madison said and he smiled. She could see his shoulders relax.

They walked out and the moustache man opened the door. His face looked like his underwear was too tight. They slipped into the back seat. Madison took Herby’s hand; it was warm now but still a little sweaty.

“Relax, this will be fun.” She said and he sighed.

“Some of these people are not very nice.” He said.

“That’s ok, I have met some mean people before. We’ll be ok.” She said.

They walked into the restaurant, and it was very fancy. She saw a lot of ladies in shiny dresses and a lot of jewelry. All the men wore suits, and she straightened Herby’s jacket. He looked very nervous. A man walked up and smiled.

“Mr. Tennyson, your table is ready.” The man said and Madison now knew their last name.

They followed the man through the restaurant, and she saw everyone looking at them. The men looked at her specifically and she tried to stay calm. There were a lot of young people their age here as well as older people, but they were all fancy. They made it to their table and the man pulled out her chair. She sat down and thanked him. He smiled at her.

“Mr. Tennyson, Phillippe will be with you tonight. Please let me know if you need anything.” The man said.

“Thank you, Marco.” Herby said. The man looked at her once more and smiled before he left.

“They all know you.” Madison said.

“They know my dad. He likes it here; this is the first time I’ve been here without him.” Herby said and picked up his water glass. She noticed his hand was shaking. This was not his comfort zone.

“It’s very nice.” She said and he nodded. He wiped his forehead with his napkin.

She looked around and there were a lot of people, but it didn’t feel crowded at all. It looked so much different than Jordan’s restaurant. She felt a tingle between her legs when she thought about her girlfriend. She took a sip of water and it even tasted fancy. Herby still looked uncomfortable, and she reached over and took his hand.

“Take a breath, I’m having a good time. This place is nice.” She said and he nodded.

“Herby my man, I guess they let anyone in here.” Madison heard a voice, and she looked up to see three boys standing next to the table. They were all very pretty and dressed very well. They looked to be very comfortable in their clothes. The one in the front was blond with blue eyes. He was very handsome, but she didn’t like his smile. It felt forced and evil. He sniffed the air.

“So, is that a new cologne, it’s nice, what’s it called, Nerd Sweat?” the blond boy said, and the others laughed. She saw Herby shrink and his face looked sad.

“Vince, just leave us alone.” Herby said softly without even raising his head. He was looking down at his napkin.

“Herby, we are just being friendly.” Vince said and his two friends snickered. Madison felt her anger rise.