Learning the Family Business Ch. 03

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Mike and his step-sister take an adventure.
2.5k words
4.22
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Part 3 of the 5 part series

Updated 06/08/2023
Created 04/06/2017
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Over the next week, Mike received the cold shoulder from his father and step-mother. They never discussed the failed attempt to land the Diaz deal with him. Instead, Mike was put on the back-burner and delegated small insignificant tasks like reading over contracts and cold-calling vendors. He worried about what his dad and step-mom would think if they ever discovered what happened in his bedroom with his step-sister late at night, but he looked forward to more visits from her all the same.

That all changed on the following Tuesday.

"Psst. Mikey!" Hillary poked her head over the top of his cube from the other side of the divider. Her long dark brown hair spilled over her shoulders and as she leaned over the divider.

"I'm breaking us out." She held a folder up in her hand similar to the ones that had contained the paperwork for the Princeton and Diaz deals the previous week. "Meet me in the parking deck in minutes."

Mike set a timer for ten minutes but, with nine remaining, silenced the alarm and then stood up, told his cube neighbor he was going to get some water, and then made a direct route to the side door that lead to the garage.

On the other side of the door stood Hillary. She looked particularly leggy today in her short tan mini-skirt, white knee high stockings, and black heels. She topped it off with a white golf shirt with the top buttons unbuttoned to tease her small perky cleavage.

"What're you looking at, dork? Let's go," she instructed, pointing to her shiny black BMW 5.

"Answer your emails but don't post anything on Instagram or whatever while we're gone, ok? Our parents will be pissed if they find out I sprung you so soon. You're supposed to be doing shit work but there's something I need your help with."

After a few minutes of turns through one of the city's wealthiest zip codes, Hillary's BMW reached a gated entrance.

"We're the agents that were sent to look over the Smythe house," Hillary flirtily called into the guard station and waved her folder. The security guard smiled back and reached forward to push a large button on his desk. With a buzz, the front gates began to pull open and Hillary drove her car up the cobblestone driveway to the front of the sprawling mansion.

Hillary hopped out of the car after she parked it in front of the front door and threw her car keys to Mike. With a wave of her remote control, the key panel on the front door snapped open and she retrieved the key to the front door.

"Isn't this amazing?" she asked as Mike followed her into the front foyer. "Ever since I was a kid, I dreamed of seeing the inside of this house every time we passed. Now it's in our firm's sales portfolio, so I can check it out as many times as I want until it sells," she squealed as she grabbed the lapels of Mike's jacket and shook him with excitement.

"Who wants' to see the bedrooms?" Hillary asked as she sprinted up the steps before Mike could answer. He enjoyed watching her little athletic booty bounce beneath her skirt as she sprung up the stairs.

Mike paced himself up the stairs. He had watched Hillary turn left at the top step but, when he reached the second floor himself, she was gone. The upper floor was laid out in an oval shape. At the top of the steps, a railing encased the stairwell which was surrounded by a sitting room. In the middle of the room rose a grand white brick fireplace with glass doors on both sides. Two antique armchairs stood guard in front of the fireplace with a small stack of thick books between them. Around the perimeter of the room were doors that led to various bedrooms.

"Hill? Where'd you go?" He called, seemingly to himself.

The small door across from the stairs looked more like a closet than a bedroom. It was locked, so he proceeded to the next door. An oval shaped handle turned and clicked open but Mike discovered the room was a nursery, with an expensive looking antique crib against one wall. He shuffled to the next room. It was decorated with a creepy looking family portrait. Either the portrait was painted to look like an antique, with the family wearing attire that went out of style many decades ago, or the subjects of the photo would be long dead by now. All the same, their eyes seemed to follow Mike as he looked under the four post bed for his mischievous step-sister.

"OK, this is creeping me out, Hil!" Mike shouted into the open sitting room as he exited the bedroom.

A faint giggle emerged from the far side of the floor and Mike followed it to a cracked bedroom door on the front half of the home. He had wandered into the master suite. On the wall to the right rested another ornate brick fireplace with bookshelves on both sides. Against the far wall was a king sized four post bed covered by a thick frilly duvet and a pile of decorative pillows propped up against the intricately carved headboard. To the left of the bed, double glass doors were cracked open and a slight breeze caused the long white curtains to flutter.

"I guess you found me," sang Hillary's voice from the open doorway farther left of the bed. From his angle, it looked like the door led to a bathroom. Out stepped Hillary. She had shed the skirt, golf shirt, and her panties. She wore only the knee-high white stockings and a lacy white bra. Mike watched her hips sway as she approached.

"Just to be honest, it wasn't just visiting the house that I'd always fantasized about..." She said while playing with Mike's tie. "You said you'd repay me for last week when I helped you get off, so it's time for me to collect."

She slung his coat sleeves down his arms, pinning them in place and planted a slow wet kiss on his lips. He could feel the underwire from her bra press into his sternum. After pulling the coat to the floor, she seductively sauntered to the large bed and bent over the mattress. Mike followed, falling to his knees and lifting his mouth to Hillary's puffy folds.

Mike could feel his cock rising from the excitement of finally getting to be alone with Hillary in the daylight. The dim moonlight that normally shone down on their late night encounters did not do her long slim legs justice, nor her high perky breasts. The moans that escaped Hillary's mouth would have been loud enough for anyone inside the residence to hear.

"Yeah, Mikey. Right fucking there. Don't stop until I come," Hillary begged, reaching a hand down between her legs to clutch a handful of Mike's hair and pull his head closer until her lower lips swallowed his lips.

He flicked his tongue across the small pink nub between her lower lips time and time again until, finally, he felt a rush of fluid down his tongue and across his chin. Hillary bucked her hips into his face, gripped his hair so tightly he thought she was going to rip out a tuft, and let out a wail that echoed off the room's high ceiling.

And then he heard only her panting and watched her belly rise and fall as she tried to catch her breath.

"That will do, Mike," Hillary said and patted the top of his head. He lapped up the fluids running down her thighs and then she scooted off to the bathroom to clean up while he wiped his mouth on the inside edge of the bed comforter. He thought it would be long dry before anyone looked under there.

***

"Please come to your father's office when you get back," the email from his step-mother read. "And bring your sister."

"Well, I guess our cover is blown," Mike said to Hillary after reading the email from his phone.

"Just be cool. I'm sure it's nothing," she replied.

They pulled into the spot Hillary's car had left vacant and slipped back into the office through the garage entry. They ran into Maria in the hallway.

"Tamara said..." She started in before Hillary interrupted.

"...We know. Thanks."

Mike followed Hillary down the hallway toward his father's office. It felt like something was caught in his throat. He didn't share Hillary's optimism about their pending meeting. There was something very curt and dry in Tamara's email that made him nervous.

"Here they are. Did you enjoy your little outing?" Tamara asked after they passed through the door to Mike's father's office. She was dressed in a black dress with a high neckline but it only served to highlight the natural curve of her ample bosom..

"I mean, it was just to get some fresh air and coffee," Hillary replied, putting on a calm facade for their parents.

"Really? Tell me, Mike, was the coffee before or after you all trespassed in our client's home?" Tamara shot back.

Mike froze. He looked to his father whose tight lipped face bore a stern look.

"Ah..."

"You know, we don't own these homes. You get that, right?" Tamara's tone implied this wasn't a joke. Mike looked around and realized there were no chairs in front of the desk. On the desk, sat a small dark monitor with a tail of cables running into the desk through a hole. "Did you think we wouldn't keep an eye on one of our most prized clients?"

She grabbed a small remote from the top of the desk, pointed it to the monitor and pushed a button. The screen lit up with four quadrants showing various security camera footage from the house Mike and Hillary had just visited. He watched one corner which captured Hillary leading him in through the front door. On another camera, some moments later, Hillary crossed the large sitting room on the second floor of the house and then transitioned to the section that captured the bedroom where she had seduced him. Tamara pressed another button and the footage fast forwarded until Mike appeared in the bedroom and then Hillary re-appeared from the bathroom door. Tamara pushed pause and the screen froze on a blurry image of Hillary standing in front of Mike, bottomless in only her bra and stockings.

"Is this how you repay us for all of our hard work and dedication to you all? By fooling around in one of our client's homes?" Tamara looked to Mike's father who exchanged a stern look.

Hillary opened her mouth to speak but was quickly cut-off.

"You think it's ok to risk everything we've worked for?" Tamara continued. "I think we need to learn a lesson here." Tamara stood up and adjusted her tight dress. Her manicured fingers pulled it back into place over her matronly hips. From behind the desk, she produced a small square paddle, similar to the one Mike had watched his father use to discipline Maria.

"I want both of you to bend over this desk," Tamara ordered. Hillary opened her mouth to speak again but was silenced again by her mother. "No excuses. Get over there."

The two step-siblings slowly stepped up to the desk. Mike looked to his right to Hillary and exchanged a look of confusion and terror.

"All the way over," Tamara corrected and Mike joined Hillary in gripping the far side of the desk. He felt the hard wooden top press against his torso and watched as his father pulled a matching paddle from below his seat, stood and followed Tamara to take positions behind their kids.

"I don't think this is going to do it, do you, Peter?" She asked Mike's father.

"Not in the least," he cooly responded.

"Mike, drop your pants," she ordered. "Hillary, lose the skirt. Mike awkwardly reached for his belt without adjusting his position. He unbuckled and unzipped and tossed the pants toward his ankles, feeling the cloth bunch up at his knees. "And your underwear," she continued. Mike looked to his left to see Hillary take a deep breath before reaching to her hips and pulling her white lacy panties down until her pale butt cheeks were exposed. He followed, feeling the cooler air in the room across his glutes and soft shaft and balls.

"Now we can begin," Tamara announced. Mike's head turned to the left as it fell to the wooden desktop. He felt the first blow from his father against his butt and listened as Tamara's paddle slapped against Hillary's behind. Hillary bucked and her eyes grew wide.

He stared at the side of Hillary's cheek for a moment and then she turned to him and flashed a devilish smile.

"This isn't for your amusement, Hillary," Tamara chastised and then Mike heard her paddle smack her daughter's bare behind again and, a moment later, Mike felt the sting of his father's paddle once more.

"Maybe we should switch sides, dear," Tamara suggested. Mike listed to the shuffling of feet as the couple traded places.

He pictured his step-mother staring at his muscular bare butt cheeks and the sight of his penis head dangling between his legs and felt a spark run from his loins up through his abdomen. He felt the sting of her paddle but could not stop himself from picturing her thick round cleavage as she pulled away. He felt his manhood swell but could not make himself feel shame. He wanted her to see it.

"I guess somebody's not getting the message," he heard Tamara say behind him. She spanked him again. The force of her paddle didn't bear the same brute strength as his father's but it stung all the same.

"Your son has a big hard dick over here. I don't know what I'm going to do with him," she said, disappointedly before winding up for another smack.

To his right, Mike saw that his sister was taking her punishment in stride. She looked straight ahead, with a zen like smile on her face as his father delivered another smack to her bare behind.

"I'll tell you two what we're going to do," he heard his father finally say as the spankings halted. "You're both off any house visits or showings until further notice."

"Wait, that's not fair," Hillary protested.

"What your father says goes," Tamara reinforced the boss's edict.

Hillary turned to Mike and mouthed, "What the fuck?" They both knew that, if Tamara was backing Mike's dad, then there would be no wiggle room for them this time.

"Now, why don't you both get dressed, go home, and think about how you're going to make this up to us." Tamara ordered.

Reaching to the floor, MIke quickly pulled his pants back up to his waist. He looked straight down at the desk while he buckled his belt. He thought he was going back to insignificant errands, for sure after this debacle but he had no idea that he would get his opportunity to redeem himself soon enough.

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1 Comments
prop69prop69almost 7 years ago
Gladly take the paddle to eat Hillary's pussy

Please bring

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