All in The Family Madison

Chapter 1 The Beginning

Oakton, a small, quaint little town in the north-east of America. Many would say picturesque with its century's old town-hall compete with a working clock tower and central park with an ornate band shelter at it's center.

The town's people love its quiet and unassuming nature. It is a town where everyone knows each other yet have enough sense to know when not to pry or dwell into their neighbor's business.

On the outskirts of town, the local community college is the community's pride. The Oakton Eagles are three time state football champions, and it's prestigious cheerleading program is the envy of the neighboring schools. The school is as old as the century old town. Looking as though it had been taken from the frames of a nineteen forties Capra film, the two-story building is "home" to Tim Miller, an assistant coach to the college football team.

Tim Miller moved to Oakton a decade earlier. Following a lengthy career teaching upstate in one of the larger cities, Tim had little difficulty adjusting to the more laid back style teaching at Oakton College. As much as he missed the hustle and bustle of the big city, he wanted to give his now teenage children a quieter, more relaxed upbringing.

After divorcing his first wife, and marrying his second, Tim knew he needed a change and Oakton was the perfect place for the four.

Tim's second wife Samantha is a guidance councilor at the college, much to the chagrin of her daughter and Tim's son. Samantha is a stunning blonde, often mistaken for being her daughter Madison's older sister. Despite her natural good looks, Samantha is quite shy and reserved. Often disappearing in the school library when not working in her smallish office. Tim is very different from his wife. Tim is stocky and muscular, when entering a room, his mere presence demands attention. Very much an extrovert, Tim is often the life of the party. It certainly wasn't uncommon for the women of Oakton, both single and not to fantasize about the football coach.

Chapter 2 The Cheerleader

It was a late Friday night and the football stadium which was up to about an hour ago filled with raucous students cheering their team on was now all but empty. His college alma mater had easily crushed their cross-town rival. Tim loved the game of football and missed playing the game. His love of the team and his impressive college career allowed him to take an assistant coaching position. The stadium lights slowly began to shut off leaving the field shrouded in darkness. Tim stepped off the playing field, walking through the bleachers towards the stadium exit.

Tim could hear voices echoing from below the bleachers. They were loud, but he couldn't make out what they were saying. There was something else. Was it crying? Or maybe grunting? Probably just the players fucking about after the game he thought. They played well and deserved some time to be boys.

"Hey Ryan, I can't believe how tight this cunt is. How come you didn't bring her around earlier?" One voice said.

"What?" another deeper voice responded.

"I said" the first man breathed deep to catch his breath before continuing. "The bitch's snatch is tight."

Tim, now realizing what was happening decided he needed a closer look. He walked the bleachers trying to pinpoint where the noise was coming from. As he got closer, he heard the slapping sound of thighs on thighs. Whoever she was, she was taking the fucking from these two players like a champ. When he started to feel the vibrations through the steel benches he knew he was in the right place. Tim moved down onto his hands and knees to see if he could find a way to see the show.

There she was. His step-daughter Madison. The team's starting quarterback was driving his cock in deep while she was bent over a picnic table beneath the bleachers. He was fucking her hard from behind. Her cheerleader outfit was still on from the game but with the skirt flipped up onto her back. She was up on her toes to make up for the height difference. Clearly and enthusiastically taking what the kid had on offer.

Madison was his wife's eighteen-year-old daughter from her first marriage. Maddie, as her close friends and family called her, was far from being your typical teenager and college student.

Maddie was busty but petite blue-eyed blond with incredibly toned abs and a firm ass. Her uniform top barely concealing her 36" c cup breasts. Her hard nipples pressed against the thin material. While she couldn't afford the scandal of going pantie-less at a game, she rarely wore a bra beneath her uniform top. At that moment, Tim could see her discarded silk red panties laying on the picnic table beside her. They weren't hard for him to recognize as he had in the past held them in his hand as he would often fold her laundry.

Although he had never seen his step-daughter exposed like this before, he had seen her around the house on several occasions in nothing more than a skimpy two piece bikinis or a short t-shirt and panties.

Tim flushed with an anger he didn't understand himself. Was it anger or was it something else. Tim quietly stepped away as to not be heard. Once far enough for them not to hear, he reached for his pocket and pulled out his phone. He found the contact labelled "Maddie" and hit the call button.

"Oh shit it's my Mom's guy... fuck, I have to answer this." With a cock still buried deep in her pussy, Madison answers her cellphone. "Hi Tim, I'm a little busy now can I call you ba..." she said.

"You know you can call me Dad. Forget it. I need you home now. Your mom is in trouble." Tim lied to his stepdaughter.

Madison began to panic as she pushed the player off of her, pulling down her short cheerleader skirt before running out from under the bleachers to the lit street as she began to sprint home. As quick as Madison was, she was no match for Tim's navy blue corvette, and he knew he could easily beat her home.

Tim could hear the front door open as he patiently waited for her in the living room sitting on a large tan sofa. Madison entered the room glistening and breathing heavily.

"Where's Mom?" She asked out of breath, now standing before him in her cheerleading uniform.

"Mom's fine, she's with your aunt." Tim paused to give her a moment to relax. "I saw what you were doing with those boys tonight."

"You saw me? Were you fucking stalking me Tim?" Madison shouted both surprised and angry.

"It's Dad you..." Pausing for a moment to choose his next words wisely, "slut!....and no. You knew I was coaching at tonight's game and I stayed back give you a ride home. It looked like you were finding yourself a ride though."

"I bet you loved that, perv. I'm basically Mom but younger and tighter." Madison spat back assuming he had watched her get fucked the entire time under the bleachers.

Tighter.

The word made Tim flush a bit.

"You're still only half the woman your mother is, and she's plenty tight. Trust me." Tim responded back, not letting the eighteen-year-old get the best of him.

Madison had taken that as a challenge. She jumped into his lap and his instincts made him catch her. She was lighter than her mother and Tim's hand felt that her body was firmer too.

"You know Tim. I never did have time to put my panties back on." She pauses for just a moment, "Oh sorry, you like being called Dad right?" she whispered into his ear as she leaned back against him and giggled.

Tim was only a man and despite the relationship he has with her, It took him less than a minute to have his belt undone and his pants pushed down around his knees. There would be consequences for sure but at that moment all he could think was that no one gets to their deathbed and wishes they'd fucked fewer teen cheerleaders.

"Let's see if you can work that pussy like your mother."

Madison's bare pussy was already flooded in the way only a girl her age could be. She needed no coaxing as it swallowed Tim's cock. All her cheerleading has made her thighs thick and strong. Tim could see them flexing as she bounced in his lap, and he couldn't help put touch, running his hand down her smooth thigh.

"Come on Daddy, let's see what you've got. There's no way you're keeping Mom happy like this." Tim's cock plunged deep into his step-daughter's pussy.

With that, young Madison rode Tim's hard cock, bouncing up and down on her step-father. Her pussy is like a vice around his cock, but he is determined to remind her who is in control.

Tim rolled her over and dropped her to the floor. He laid her head and chest into the sofa he had been sitting on. Her knees touched the ground, and she spread her legs to give him the perfect view.

"Ass up and face down just like your mother." Tim commanded.

"What the fuck did you say?" Madison turned sharply to face her step-father as he moved up behind her, now completely naked. She glances back at his erect member.

Without saying another word, Tim moved in closer. She feels the head of his cock brush against her ass before he drives himself deep inside her. Madison had started to respond but was now finding herself completely overwhelmed. The boys she was with may have had youth on their side, but they didn't have half Tim's power or technique. She screamed into the pillows as her legs shook from the pounding. Tim continued to drive his cock deeper and deeper into her pussy as he lifted up her top revealing her perfect breast, holding one firm in his hand.

"I can't take it...I can't...I can't... Daddy please." Madison soon begged to him.

"Please what?" Tim asked with a devilish grin.

"I need you to cum." she pleaded.

"You want it? Why should I give it to you?" as he continued to pound her pussy with his thick dick.

Tim knew he had her now. She would do anything to get it. She had probably never been with a real man before this he thought.

"You really are a little slut you know that?"

"Yes" Madison moaned.

"You want me to cum inside you?" Tim asked, although he had no intention of giving her a choice.

"Yes... Please." she moaned louder.

"Fine" as he released his grasp upon her tits.

Tim finally came as he planted both hands firmly on either side of her ass. His cock erupted inside her, filling her with his cum. He left the tip in and spread he cheeks to view his handy work. He pulled out the last bit and watched their mixed juices trickle out to the carpet. Before he let her go he left a dab of his cum on her tight asshole.

He stood over the now cum drunk girl as she moaned into the cushions and her eyes rolled in her head. Tim put his pants back on he made himself very clear to his step-daughter.

"Put your clothes and get cleaned up before your mother gets home. And clean the cum stains out of your uniform. You're going to need to wear that again tomorrow after your mom leaves for work."

"Yes Dad."

Chapter 3 The Garage

Not a moment had passed where Tim's mind wasn't distracted by his stepdaughter Madison.

An incredibly tight pussy like that changes a man's priorities. He was completely distracted at work and the night after his first encounter with Madison, as he was laying in bed thrusting hard into his wife, he was still thinking of her. Tighter, he remembered her saying that. She was right too, but he wasn't going to give her the satisfaction of knowing it. He could see the smug look on her cute face. She'd have that devilish sparkle in her blue eyes. He hadn't noticed them before but now he got the feeling they were always on him.

"Dad I'm heading out with the boys. I think we're going to catch a movie or something." Nathan said.

Nathan was Tim's twenty-year-old son from his first marriage. He was his spitting image or at least an image from two decades ago.

"Alright, be back by midnight and don't forget your inhaler. I don't want to have to come looking for you again. Last time it was date night with your mother and it spoiled the whole thing." Tim said.

Nathan grinned at his father.

"Watch it." was Tim's only response.

Tim had the house to himself now. His wife had finished several glasses of rather expensive red wine and crawled into bed just over an hour ago. He didn't begrudge the drinking, but he had hoped that it would have loosened her up. But that was not the case.

He needed relief as his only thoughts were on the vice-like grip wrapped around his cock now several days ago. He contemplated sneaking into his stepdaughter's room to retrieve a pair of black lace panties he has seen in the wash sometime before.. He still had a few hours until Nathan was going to be home and Madison was staying at a friend's. He was giving serious thought to relieving himself into a tiny pair of her panties when he heard a noise in the garage.

He opened the door from the house to the garage to find the one person he didn't need to be thinking about right now.

"What the hell are you doing here? You are supposed spending the night at Stacie's."

"Well, I am not welcome there anymore." Madison said with a stumble and sway to her step. She leaned on the family mini-van for support.

"Are you fucking drunk!" Tim started to yell but caught himself fearing he would wake his wife.

"I had a few drinks from Stacie's dad's liquor cabinet. Big wooden one, very fancy office, probably expensive stuff." She stopped to steady herself. "Anyway he was not happy when he found me so I showed him my tits. I think he might be gay because he kicked me out, and now I'm here."

That night, Madison had been wearing a tight navy crop top and tight spandex shorts.

"Madison. You can't be doing that with married men."

"You're married."

Tim stopped. What could he say?

"That's different." was all Tim could muster.

"Why, cause were family?" Madison stared her stepfather directly in the eye.

Tim didn't like where she was going with this. Not so much that he didn't like as he was suddenly feeling very uncomfortable. He moved passed her, opening the van door. He needed to keep her somewhere safe until she sobered up.

"Get in." he said while giving her a little push, and he slammed the door behind them. She crawled in on her hands and knees. Her round ass was in his face. He wasn't sure if she was trying to start something or just unaware. She lay on her back to entice him to get on top of her, and it became clear, but Tim had other ideas.

"Do you know how to suck cock?"

"Mmmmmm" she smiled as she hummed to him.

"Well then? I want you tits out. I'm not going to let Stacie's dad get more out of my daughter than me." Tim commanded.

She dropped her top and let her breasts lay on display for his hungry eyes. They were bigger than her mother's even though she was few inches shorter. He cupped them briefly before pulling her by the blond hair and pushing her into his lap.

With that, Madison took control. Unzipping Tim's jeans and pulled out his rapidly hardening cock. With little hesitation, she guided his thick member between her lips into her mouth. Her tongue swirling around his shaft as she took him deeper. Madison sucked Tim's cock like she had been a seasoned professional. Randomly releasing his cock to suck on her smooth balls. Tim moaned in approval.

"Who knew you were such a good little cocksucker?

She looked up grinning. "Do you want a list?"

"Fucking whore." Tim teased his stepdaughter.

Tim could hold back no longer as he pulled his cock out from Maddy's hungry mouth, moving himself down so that his cock rested between her two firm, big tits. Madison squeezed her tits around her step-fathers cock. With that, Tim thrust between them, his climax rapidly approaching.

"Cum on me daddy." Madison commanded her stepdad.

With no further encouragement, Tim's cock erupted shooting thick ribbons of white cum across her chest and neck.

Outside Nathan was returning to the house. His Dad was right, and he had forgotten his inhaler again. He hoped he could sneak in through the garage and not be noticed. He didn't want to give his Dad the satisfaction. Instead of his inhaler though, he found his step-sister. With her tits around his dads cock while he glazed her from her nipples to her chin.

The van's windows stopped Tim from hearing is son come in. He had no idea that someone was watching him feed Madison the cum from her chest with his fingers.

Chapter 4 The Babysitter

Madison was happy for the opportunity to make some money. Tonight she'd be babysitting for a family friend down the street. His wife was out of town, and he had to work. They needed someone to watch their younger son. They had an older son named Colt too, but he would be out all night with Madison's brother Nathan. Nathan had been the one to set the whole thing up. She didn't know why he suddenly believed in her, but the chance was appreciated.

Madison was also excited to see Dan. He was the father of the household and despite her teasing him with a flirtatious swerve every time she walked by the house, she hadn't yet been able to get his attention. He was older, maybe even older than her step-dad, but he must have worked out more. Madison had to admit to herself, she did have a type.

"Alright so Connor will want to play games all night, but you have to make sure he's in bed by nine. It's important so don't forget nine o'clock." Dan said as he walked Madison around the house.

"Help yourself to the fridge if you'd like. Stay out of the liquor cabinet. I'll be back late. Call if you need me." He continued as he grabbed a heavy black bag.

Madison noticed that Dan was acting funny. He was rushing and wouldn't make eye contact with her. Hungry for attention she put her body in front of him before he could make it out the door. Sandwiched between Dan and his exit she took the chance to get him talking.

"Where are you going tonight?"

"Local gig" he said holding up the bag.

"What's in there?"

"Just some standard gear. Extra lenses and SD cards."

"Like photography? Maybe you could take my picture sometime?" She leaned into him pretending to reach for the bag.

"I got to go." Dan said and he rushed out.

Madison smiled at how flustered he had become. She knew that was wearing him down. If she could set up a few more babysitting nights she'd have him in no time. For now though she was going to have to take care of Connor.

The night was pretty uneventful as far was Madison was concerned. It was quarter after nine and the boy had gone down easy. Now she just had to relax and wait for Dan to come home. He hadn't really said when he was going to be back and Madison got a devilish idea.

Cocktail in hand, she wandered up to the master bedroom. The bed had been made neat and tidy. She wondered if Dan or his wife had made it. Dan was definitely the neat and tidy type, so she guessed it was him.

She had come over wearing her classic "totally innocent" look. Tight sweatpants and a v-neck that was maybe just a bit to short. It wouldn't show off her tummy unless she stretched or bent. It was the kind of outfit that grabbed attention but no one could fault her for it. It was just the way it fit her body after all.

Madison pulled her sweatpants down around her knees and got up on the bed. On all fours she reached around to snap a picture of her backside with her phone. She sat up to examine the picture. It was perfect except it needed one more change. She cropped her face from it and then sent it to Tim. She loved the idea of him seeing his phone and then frantically trying to hide it before her mother saw. She hoped he had been smart enough to change her contact number. Oh, well she thought.

"Taking some pictures?" Dan said.

Madison nearly jumped right off the bed. She hadn't even heard him come in.

"I'm sorry it was for my boyfriend. He put me up to it." She replied.

It was only when she saw him scanning her body that she realized she still hadn't pulled her pants back up.