Learning the Family Business

Mike looked down at the small dark knobs formed by Stacy's collar bones. He could feel a shift in his loins as she pulled one of her yellow sundress straps down past her shoulder and then reached for the other strap. It was finally happening: she would be his at last. Just as the dress's soft fabric slipped past her cleavage, revealing the deep ridges between the mountains it hid, the earth beneath his feet shook and opened and he felt himself falling away and falling toward a bright light..

"Mike! Dad said you're going back to roofing if you aren't at breakfast in five minutes!"

His eyes slowly opened to look up at his older long limbed step-sister jumping on his bed in her short soccer shorts and black concert shirt. Her long thin thighs were pale and smooth and her athletic calves were covered by a pair of tight black and white striped socks. She had cut open the arm holes in her sleeves for ventilation and he caught a glimpse of the side of her small sloped breast before realizing where he was and who he was looking at.

"I hear you, Hillary," Mike shouted back, trying to hide his morning erection.

While he couldn't help enjoy the view, he knew this was no time reveal his attraction to the step-sister who had grown up just a room away. She kicked his bed covers away from his body. He felt the cool air in the room on his thick bare chest and then sat up quickly when she kicked the covers away from his lap.

"Nice tighty whities, dork," his sister teased as he moved his hands to hide his shame.

"Get the fuck out of my room, Hillary!" he erupted. She put her thin hand to her pouty mouth and giggled as she looked down at her vulnerable brother and then jumped off the bed and slammed the door shut as she left his room.

He felt lucky that his father let him work in the office for the family business during his college summer break but he knew the stern man wouldn't hesitate to put him back on outdoor maintenance jobs if he if he didn't fly straight. He took a quick cold shower in the Jack-and-Jill bathroom he shared with Hillary and tried to calm his nerves after his sensual dream about her best friend.

After dressing in one of his tailored suits, he darted downstairs and wolfed down toast and a mug of coffee. If his freshman year in college had taught him one thing, it was how to get from his bed to a classroom, fully dressed, in a minimal amount of time. He tried to keep his composure when Stacy breezed into the kitchen.

Stacy and Hillary went to a nearby college that rivaled Mike's out of state college in sports and academics and they never failed to give him hell about it. Hillary had invited Stacy to stay with their family for the summer rather than head back home. As a rising senior, Stacy had already worked her way up through Mike's family real estate firm. She had already completed her real estate license and had closed a number of sales since she started working for the business.

She wasn't just smart, she also knew how to look the part. This morning, Stacy was dressed in a tight sleeveless leopard print dress. As she passed Mike he tried to keep his composure but couldn't help stare at the way her thick round butt filled out the back of the dark dress.

"Good morning," she said as she passed. She left a tail of expensive smelling perfume as she walked by.

"Uh, yeah. Good..." Mike awkwardly responded as he continued to stare at her caramel colored skin and long straightened hair that had been treated with blonde highlights. Just as she bent over the table to look at the morning's newspaper, Mike was interrupted by a slap on his back.

"Hey there, champ. Finally decided to get up for work? Good choice," Mike's dad wasn't a morning person and his tone made it clear that work was not optional for his son.

The group grabbed travel mugs for their coffee and then headed out in their individual luxury cars: an Audi SUV for his father, a Lexus sedan for Stacy, and Mike in his handed down BMW. Mike split off from the caravan to stop by a local bakery. As the office do-boy, it was Mike's job to pick up the breakfast order for the agents at his father's office every morning. This was his third year running whatever errands were needed to setup open houses and tidy up luxury homes before showings and he prayed it would be his last.

The front desk receptionist was always a sight for sore eyes after a long spring semester. Maria Gutierrez greeted Mike with a wide smile and hurried to help him carry in the trays of bagels and coffee he carried.

"Welcome back," she cooed. The entire office worked hard to maintain a fit appearance and Maria was no exception. Mike took stock of her thin waist and bubbly behind as he followed her to the conference room.

"Your father needs to see you in his office," she informed Mike with a look of warning.

Maria to attend to the snacks while he wandered off through the chic modern office, past the closed door to his step-mother's office, and finally arrived at his father's heavy wooden door.

"Enter," his father commanded after Mike knocked. He did not rise from his his oversized desk as he offered Mike a seat.

Sitting on the other side of the desk, Mike saw his broad shoulders, steel blue eyes, and wavy blonde hair reflected back at him while he waited for his father to finish an email.

"Today's a big day, Mike. I'm really proud of how hard you've worked so I'm bumping you up. No more errands. I just want you to close some deals and make me proud."

Mike sighed in relief while his father reached for a button on his office phone. "Stacy, come on over," his father barked into the speaker.

After a few seconds, Stacy pushed her way into Mike's father's office. She smiled from ear-to-ear and gripped Mike's muscular shoulder through his suit coat. His muscles tensed at the energy she sent with her touch.

"You ready for this?" she asked rhetorically.

"Mike, you're not licensed so I can't just cut you loose, but I asked Stacy to hold your hand while she shows you the tougher... more intimate side of our business," Mike's father said.

"Don't worry, I'll take really good care of your boy," Stacy responded, rubbing a caring hand across the back of his neck. Mike shifted in his seat as he felt his manhood swell at Stacy's touch. She had always shown Mike kindness but he was excited to finally get closer to his step-sister's friend.

Stacy drove Mike to their first appointment in her sleek Lexus. They certainly could not show up to a multi-million dollar home in his well worn BMW. When they arrived, an attractive couple in business attire waited for them on the column-lined porch of the expansive home.

"Mike, this is Chelsea and Royce Princeton. We've been working on this deal for a while and I think I've almost convinced them to go for it."

The blonde haired thin framed woman offered a gentle handshake. Mike tried not to let his eyes drift down the front of her scooped white blouse to her small pert breasts as he looked down into her pale blue eyes. Royce was dressed in a striped suit that fit snugly on his tall frame. He gripped Mike's hand tightly.

"Are you all a couple?" Royce asked as he released Mike from his strangling grip.

"Oh, I'm flattered but little Mike is just my mentoree today," Stacy replied. She reached up to his carefully sculpted hair and and gave it a flirty toss.

"That's too bad. You're such stunning kids," Chelsea added.

Mike was taken aback by the beautiful couple's upfront demeanor. He'd gotten used to being hit on by his step-mother's friends as he filled into his six foot two frame but this was the first time a woman in her thirties showed him this kind of attention.

A short tour of the house followed, as Chelsea and Royce just wanted one last look around for their final questions. Stacy led them across marble floors to the massive home theater and indoor pool. It seemed to Mike that the couple wanted to show off their new digs as much they wanted to give it one more inspection.

When the group reached the top of the stairs to the bedroom level of the home, Royce hung back with Mike.

"She's a dream, isn't she?" Royce asked. He stared down the hall toward his wife whose thin waist and athletic butt were covered by a tight black skirt.

"Yeah, and she's all yours," Mike replied, not sure if Royce was referring to the home or his wife.

"Well, I think you'll find we're very welcoming people. We like to keep an... open door policy, if you know what I mean," Royce said with a pat on Mike's shoulder.

Mike stood stiff as a board in the hallway while Royce continued after his wife and Stacy. He had always heard about the free swinging couples that lived in homes like these but never imagined he would end up feeling propositioned. The very thought of walking down the hallway and lifting Chelsea's tight skirt and ravaging her from behind made his head spin, so he tried to block out the thought while they wrapped up the tour.

After the tour, Stacy made her final pitch before the two couples split off in the front foyer. Back in Stacy's car, Mike settled into his black leather passenger seat while Stacy checked her messages on her phone.

"So, Mike..." Stacy turned her full attention to him. She looked up at him with her unblinking hazel eyes, commanding his attention in return.

"I don't know how much you know about the inner workings of your family's company but we have a way of rewarding success." Stacy moved her hand to Mike's knee and traced a finger up the seam of his trousers until she was brushing her fingers across the mound between his legs.

"Are you ready to do whatever it takes to close this deal so I can give you a reward, Mikey?" She asked as she reached to the hem of her skirt and pulled it up to her hips. She wasn't wearing any underwear and let him gaze down at her bare chocolate colored lower lips. Her fingers danced between her legs while he watched.

"Uh... yeah. Whatever it takes," Mike stammered as he reached for her smooth brown leg.

"Good," she responded, slapping away his hand and returning her skirt hem to its rightful place. "Then there's something you need to do for us tonight."

***

Later that night, Mike clutched a heavy folder in his hand as he made his way to room 511 of an intown luxury hotel. The envelope was thick with the documents for the offer that the Princetons would need to sign for their new home. His nerves were a wreck, hoping that he would not make a fool of himself with the elegant couple.

He found the couple's room and knocked.

"There he is," Royce greeted Mike with an enthusiastic handshake and gave him a firm pat on the back as he ushered him into the spacious suite. Mike walked out of the entryway and into a living room that would have fit into his family's own spacious home. "I'll take those," Royce offered, removing the files from Mike's hand and leading him through another door into a posh bedroom with a four post bed and floor to ceiling windows on one side. The twinkling cityscape in the distance was breathtaking.

"Can I get you a drink?" Royce asked, not bothering to learn that Mike was still only twenty as he made his way to the bar and poured two fingers of brown liquor into three tumblers. Royce handed one glass to Mike who sat in a leather trimmed chair against the window, sipped, and tried to choke back tears from the smoky scotch. Royce flipped through the documents laid out on top of the bar while he drank from his glass.

"Is Chelsea here, too?" Mike asked, wondering what Royce intended to do with the third glass.

"Oh, of course. She was just freshening up. Honey, we're all here," Royce called toward the opposite side of the room.

A door opened and Chelsea's long pale leg extended through the threshold. She sauntered into the room in a sheer black fully body chemise and and a sparkling diamond necklace. Mike nearly dropped his glass in shock as he stared at the outline of the full round globes formed by the base of her breasts..

"Here's the thing, Mike," Royce started as Chelsea crossed in front of the bed to receive her glass from her husband. "The house is great and these documents look fine but I think Chelsea needs just a little more convincing."

Chelsea leaned into Royce's chest and sipped from her glass while she stared into Mike's eyes.

"Stacy said you were committed to whatever we need to get us to finalize the offer. You're in luck, Mike, because my wife has very specific needs and a tall handsome young man such as yourself is always on the list. Turn around, honey, give him the full tour," Royce held Chelsea's delicate hand over her head and she twirled a half circle and paused so Mike could look at how the chemise cut into a thong between her tight round butt cheeks.

"Do you like looking at Chelsea's ass, Mike? I thought so..." Royce placed his scotch on the bar and slid his free hand down Chelsea's side and cupped one of her cheeks.

Chelsea turned her head to look at Mike while he watched her husband fondle her ass. She smiled and then whispered something to Royce.

"She wants to see what you're hiding under that suit, Mike. Don't be rude..."

The tumbler shook in Mike's hand as he lowered it to a glass table next to the bed. His legs felt weak as he started to rise. Chelsea turned and crossed what felt like an expansive distance between them. Mike could make out her small pokey nipples beneath the chemise and a tuft of blonde hair between her legs.

"Don't be shy, I'll only bite if you ask nicely," Chelsea purred into Mike's ear and then pushed his coat off his shoulders and ran her hand down his chest to pull off his belt. Mike clumsily pulled his shoes and socks off and then tossed his slacks to the floor. Chelsea slowly rubbed the the bulge in his black briefs, encouraging its growth.

"That feels nice, doesn't it?" Royce asked. "Chelsea, why don't you go sit on the bed with Mike and see where things go while I get more comfortable," he said and then began unbuttoning his shirt.

Chelsea led Mike to the bed and the two sat side-by-side on the edge as they began to share a long wet kiss. She sat between Mike and Royce and Mike could see Royce pull off his shirt and then trousers before dropping his boxers to the floor. Royce presented a fairly intimidating figure for a man in his thirties. His chest and abs were tanned and muscular from what looked like years of work in the gym. Below the waist, Royce's length and girth rivaled Mike's own impressive manhood.

Mike began to feel bold now that the ice was beyond broken and he reached a hand underneath Chelsea's chemise to fondle her breasts. They were enhanced but still less than a handful. He cupped each round breast in turn as he lowered his lips to her responsive chest.

After Mike got his chance to explore Chelsea's chest, she pulled away from his mouth and slid back onto the bed, pulling the fabric between her legs to the side. She beckoned to him, inviting him to explore her smooth pink lower lips.

Mike looked to Royce who winked approvingly as he gently fondled his balls and shaft with his hand. Mike dropped to his knees and bent over between Chelsea's still youthful legs. His tongue played across the surface of her smooth lips and then his fingers parted her so that he could tickle her bud with the tip of his tongue. Chelsea sighed and bucked while Mike's tongue explored her folds and openings.

He could hear the bare skin-on-skin sound of Royce pleasuring himself in the background while he watched this college kid pleasure his wife. "You like how his tongue feels inside you, baby? You look so fucking hot laying there with him between your legs," he said, breathlessly, as he encouraged the pair.

Soon, Chelsea's cries were echoing off the room's tall windows as Mike brought her to climax. After her shuddering stopped, she sat up on the bed and smiled down at Mike.

"Sounds like you're as good as she hoped. I think she's got something for us, don't you honey," Royce said as he approached the bed.

Chelsea summoned Mike to his feet and then pulled his briefs to the floor. His erection shot straight up in the air as it escaped the waistband and Chelsea wasted no time gripping it with her left hand. In her right hand, she took hold of her husband's pulsing shaft and took turns placing her lips over top of each man's swollen head.

Royce reached to his wife's shoulders and lowered her straps to uncover her breasts. They watched her breasts bounce while her head bobbed in front of their waists. At one point, Chelsea pressed her mouth down to the base of Royce's mammoth shaft and Mike realized he couldn't hold back any longer. Chelsea's tight grip was sliding across his pre-cum lubricated shaft and he sent a fountain of white semen across Chelsea's cheek and down to her sparkling necklace.

"Oh fuck," Royce grunted and then leaned back and moaned as he emptied his own load into Chelsea's eagerly awaiting cheeks. She showed her husband his milky gift, swallowed, and then turned to suck the last drops from Mike's trembling head.

***

On the drive home from the hotel, Mike could feel his legs tremble with exhaustion. He stumbled up the stairs in his family's four car garage that led into the house and then tore into dinner leftovers he found in the fridge.

When he reached his bedroom, moonlight from the window revealed Hillary asleep under his covers. He could see her pale bare shoulders poking out of the top of the sheets. It wasn't unusual for his step-sister to find solace in his bed after a long work day but he was surprised to find her here after her day off from the family firm. He could hear his heart beating in his head as she looked at her thin graceful face and wondered what she was hiding under the covers.

Mike quietly slipped out of his shoes and suit, leaving only his briefs on as he left his clothes in a bunch on the floor. As many times as Hillary had slept beside him, he knew she wouldn't mind that he made himself comfortable.

He tried not to disturb his sleeping sister as he crept under the covers but she rolled into his arms. Goosebumps rose on his arms when he felt her warm breath against his sternum and she reached forward to explore the reason for her disturbance.

"Oh, I didn't think you'd be home tonight," she said with a sly smile a her brown saucer shaped eyes opened. "Stacy told me she was initiating you into the family business. I guess you know all about our little secret now, huh?"

Mike was silent while Hillary ran her fingers over his stomach and up his chest. There were too many questions on his mind to know where to begin.

"The thing is, I'm just a little jealous. If I had worked today, maybe I could reward you for a job well done instead of Stacy. I'm having some trouble accepting that she gets to go first," Hillary whispered as her fingers continued to explore his abdomen and tease at the top of his waistband. "Don't you want me, Mike?"

He took the hint and placed a slow soft kiss on her pouty lips. Last summer, on their family vacation, Mike managed to spy on Stacy, Hillary, and his step-mother when they ditched Mike and his father to hit a clothing optional beach. That view from a distance did not compare to tonight, though, as Mike pulled back the covers and looked down at Hillary's slim perky breasts laying against her bare chest in the moonlight.

Hillary's hand slid under his waistband and played with his rising erection while his tongue traced the bumpy outline of her nipples. His hand found its way down her flat stomach to the smooth thin folds between her legs and she spread her legs to make room for his long athletic fingers.

"Oh, Mikey, I'm ready for you," she told her little brother between deep sighs and she flipped her hips onto his pelvis and pulled the tip of his penis inside her wet opening.