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.Mike's hands found the small firm curves of her ass and held tight as she rocked her pelvis on top of his. He stared up at his sister's tight nubile body while she leaned back and proceeded to grind her hips into his hips. Just as Mike became paranoid about the noise his creaking bed was making, Hillary leaned her mouth next to his ear.

"I want you to come with me. It's ok, I'm on the pill," she whispered as her rocking motion sped up. She buried her face into his meaty shoulder and her mouth was soon humming from the ecstasy of the moment. Mike felt his face flush as his orgasm overtook him and he bucked his hips to fill her tight opening with his seed.

She rolled onto the bed when they had finished and they lay awake in the moonlight for several minutes, studying each other's nude bodies for the first time.

"Thanks. I needed that," she finally said before sitting up and then making her way to the bathroom that connected their bedrooms. As the bathroom door clicked closed, Mike hoped this wouldn't' be the last time she'd sneak into his bed.

There was an electricity in the air when Mike entered the office the next morning.

"Good morning Mike," Maria greeted him with her usual wide smile. "Congratulations, I heard the Princeton's signed their offer. Your dad is going to be so proud."

Mike slipped past the steel reception desk trying to play it cool as he smiled back at Maria and headed to the bullpen where his cube was located. He caught up on his email and then headed to the break room where he ran into his sister and Stacy. Stacy wore a conservative tan suit coat over a white blouse and grey skirt today, nothing like the curve hugging ensemble she wore to the previous day's showing.

"Congrats, killer. Sounds like that Princeton deal is going to close. You must be excited," she chided him with a punch to the shoulder.

"Mike, I need to see you in my office," his father's voice barked over the intercom system.

"Sounds urgent. Catch you later, killer." Stacy slapped Mike's butt with a backhand as he began a slow march out of the breakroom. As he walked through the hallway, he could hear the other employees in the bullpen heckling him. When he reached his father's office, he could tell his father wouldn't have found their jokes funny.

"We've got a serious situation to handle, Mike. You see, one day you might run this company. Unless your sister beats you to it. That means you need to understand that you have keep your employees under your thumb. Just a few rule breakers can ruin this for everything. I'm sorry but I need you to stay in here while I handle this." His father reached for his phone and dialed an extension. "Maria, can you come see me."

His father glared at him while they waited in silence.

Maria leaned in the doorway a few minutes later. "How can I help you, Mr. Emerson?"

"Can you close the door, Maria?" his father flatly requested. "No need to sit down," he added as she began to slip into one of his office chairs after closing the door. "Now, Maria, you know I'm a stickler for rules."

"Of course. The rules exist for a reason," Maria replied with a tremble to her voice.

"I'm glad you understand. Mike, please go stand next to the window behind me. Maria, I'm going to have to ask you to bend over the desk.."

Mike's heart raced. He couldn't believe the words he was hearing from his father's mouth. He complied with the command and stood at the back of the office with statuesque rigidity. Maria slowly lowered her hands to the desk and then slid them forward until they reached the other side. Her mountainous butt cheeks were nearly bursting from her tight red skirt.

"Does he have to stay for this?" She asked, staring up at Mike with big green eyes.

"I'm afraid so. It's the only way he'll learn. Now, please lift up your skirt."

Mike's heart skipped another beat as he looked down at Maria's long straight brown hair that fell across her blushing face. After a long pause, she reached down to the hem of her knee-length skirt and pulled it up to her waist. She wasn't wearing any panties and he could see the tops of her plump tan butt cheeks. He tried to stay calm as the erotic tension in the room skyrocketed.

"Is there something wrong, Mr. Emerson?"

"Mike, come over here."

Rounding the desk, Mike pulled up behind Maria and looked down at her backside with his father. Her brown lower folds were visible from this angle, pinched between her tight tan thighs.

"See, no panties at all," His father said, gesturing toward Maria's backside. "You know there's a dress code, Maria. Administrative staff must wear underwear. Now I'm going to have to show Mike how we punish people who break rules."

"If you must," she replied with a note of resignation.

"Mike, take this key and go open the cabinet in the back corner." His father handed him a small key from his pocket and Mike used it to unlock the double doored metal cabinet and then gasped when he saw its contents. Inside the cabinet hung whips, flogs, canes, and vibrators of various shapes and sizes. "Bring me the wood paddle."

Mike found the square shaped wooden implement with a few wide holes cut into it hanging from the top of the cabinet and retrieved it for his father. He returned to his place at his father's side as his father got into position on the other side of Maria's bottom with the small paddle in hand.

"I don't know why you insist on being such a bad girl, Maria. You could really go places if you shaped up," his father lectured before delivering the first blow to her bare butt cheeks.

"Oooh!" she cooed as the first blow landed. Mike was starting to pick up on the idea that this wasn't the first time these two had played out this scenario. In fact, as another smack landed and rippled through Maria's ass, Mike realized she was definitely enjoying this. She moaned in ecstasy as his father landed another blow and sticky fluids were beginning to drip from her tight lower lips.

"Now, do you understand me this time?" Mike's father asked after landing one more blow.

"Oh, Mr. Emerson, I promise I'll be good," Maria panted. Her ass prominently featured several red squares where his father had struck her. She did not move, remaining bent over the desk while her chest rapidly rose and fell.

"That's enough for now. If you need to relieve yourself, I'll allow it," MIke's father added.

"Thank you, sir," came Maria's reply. While Mike and his father watched from behind, she quickly moved a hand to her swollen vulva and pressed her fingers between her lips and then rubbed herself aggressively until the desk was rocking from her movements. She finished with a quiet shriek and then slumped onto the desk before removing her dripping fingers from her folds. Mike's father crossed around to the back of his desk, opened a drawer, and then produced a singular tissue he offered her for cleanup before she straightened her skirt and headed out the door.

"Thanks for your assistance, Mike. You can go back to your cube."

His father made a line for the open cabinet and carefully stored the paddle. Mike stumbled out the door, his hormones still racing from watching Maria's paddling. He found his throat parched and turned to head back to the break room for relief.

"There's our little closer," he heard his step-mother say as he passed her office door. He stood stiff in the hallway, hoping she didn't notice the bulge in his pants. He wondered if she had heard Maria through the wall dividing her office from his father's.

"All these years we've lived under the same roof and I didn't know you had it in you," she said as he rigidly turned to face her office.

Mike's step-mother, Tamara reclined in her chair behind her large wooden desk while Stacy sat in front. Tamara's long blonde hair fell across the shoulders of her black suit jacket. Her white blouse covered her melon sized breasts.

"Come in here, stud," she requested and he drifted through her office door in a daze. "Close the door and take a seat.

Stacy smiled at Mike as he passed her to grab the other chair in front of his step-mother's desk.

"What a team! I've got another home and, this time, I think it'll take both of you to close the deal. You think you're up for it?

"Now that I've got this ace up my sleeve, I'm ready for anything," Stacy gave Mike's arm an enthusiastic squeeze. She lingered for a moment, giving her fingers time to explore the contours of his bicep.

"That's what I like to hear." Tamara grabbed a folder and opened it for Stacy and Mike to see. On the first page of the file was a color photo of a Latin American couple embracing each other from the side with bright smiles on their faces. "Gloria and Santiago Diaz are moving into town from Columbia. Mike's dad and I met them at a... function and they've all but finalized their decision. Do you think you two can give them a very special welcome for me?"

Stacy and Mike stared down at the photo. They stood in front of a golf cart. Santiago wore a green and white striped golf shirt tucked into his green slacks and had his arm wrapped around Gloria's narrow waist. Her pink golf dress hugged her small breasts and curvy hips.

"Don't worry about us, Tamara. It's in the bag," Stacy assured his mother.

"Great," Tamara closed the folder and slid it to the side of the desktop. "You're meeting them after lunch at the beach, so I bought some new trunks for you to try on, Mike. I hope you don't mind." She pulled open a desk drawer and produced a pair of very short grey trunks.

Mike blushed. His face felt like it was on fire.

"Here?" he nearly swallowed his question.

"Quality control is one of my specialities," Tamara answered. "Don't worry, I'm just here for support," she added as she rolled backward from her desk. "Now, I'm sure Stacy wants to see what she's working with. Can you stand up for us?"

Mike slowly complied, rising from his chair while staring at the zig zag patterns in the carpet.

"That's good. Go ahead and get that suit off. It's ok, we don't judge."

Mike slowly pulled off his jacket and tossed it on the chair. He loosened his shirt and tie and swallowed hard as he noticed Stacy had turned to look up at him. He pulled the shirt over his head and felt a hand on his belt buckle as he wrestled to pull his head free. He looked down to watch Stacy open his buckle, unzip his fly, and then throw his pants to the floor.

"You'll need the get the rest off if you're going to fit into the trunks, silly," his step-mother pointed out. He looked at Tamara and she held a pen to her lips, as though she was taking mental notes while he stripped for her.

The moment of truth had arrived. He could still chicken out - grab his pants, and run out of the room. Or he could see how far this activity was going to go. Mike inserted his thumbs into the elastic of his tight black briefs and tossed them to the floor. Stacy sat back in her chair and her eyes opened wide.

"He is a sight to see, isn't he, Stacy? All that soccer and swimming did his body good. And he's got a beautiful penis, just like his father." There was something about hearing his step-mother compare his dick to his father's that made him feel so wrong and, yet, so turned on at the same time.

Mike mentally fought off an erection as he pulled up the trunks. They left little room for his slightly engorged penis and hugged his ass in the back.

"They're kind of European. I think they'll do. Wouldn't you, Stacy?" Stacy nodded and snickered.

"But we have another matter to attend to. You see, Mike, your father is someone who keeps people on a short leash and is quick to use the lash to motivate them. I, on the other hand, prefer the carrot for motivation. I think you two have something to attend to?"

"You know it," Stacy responded. She smiled up at Mike, flashing her wide white toothed grin and pulled his trunks down his thighs before he had a chance to protest. "I always wanted to know what you felt like," she said, running her fingers down his limp meaty shaft.

Stacy stood up and slipped out of her jacket, tossing it to the desk. She stretched upward, arching her back to give Mike a nice view of her bubbly cleavage and then leaned into him. She planted a kiss on his lips with her smooth full lips and then lowered to his neck where she kissed him again. The trail of kisses descended his sternum to his toned abs and then just above the small patch of blonde pubic hair above the base of his rising penis.

She took his pulsing shaft in her hand and stroked it gently while she kissed around the base.

"Don't forget his balls," his step-mother urged from behind the desk. He felt ashamed and thrilled at the same time as the busty woman who helped raise him watched her daughter's best friend deliver his reward.

Stacy pulled his trunks down past his knees and went to town on the base of his plum sized balls. She pulled at his smooth scrotum with her lips and he felt her tongue dance across the bumpy surface. Her hand continued to stroke his throbbing shaft. After he reached full mast and his balls were dripping with her sticky saliva, she leaned back and pulled her blouse straps down her arms, reached to the neckline, and then pulled her blouse and bra forward in one motion. Her milk chocolate colored missile-like breasts popped free from her bra and fell in front of her chest and she teased her dark nipples for him with her fingers.

Stacy rose from her knees and then turned around and leaned over her chair back, offering her tight round backside to him as she pulled her dress up to her hips. He pulled the stringy white thong between her cheeks to the side with a finger, pressed her dark lower lips apart, and eased into her eagerly awaiting slippery hole.

She moaned as Mike pressed the heart shaped tip of his penis inside her.

"That looks like fun," his step-mother chirped as he pressed deeper inside Stacy until her meaty ass was banging up against his pelvis.

"That's right, Mike, give it to her," Tamara continued to urge him on as his thrusts took him progressively deeper inside Stacy's warm wet opening. He could feel her juices building up on his cock and spilling out onto his legs.

He stood over Tamara's ass, watching it ripple with every thrust. She turned her head and watched him banging her for all she was worth.

"Give me that big hard cock, Mike. I'm going to come soon. Don't stop," she begged. Finally, she bit down on her fingers and tensed her face, clearly holding back a wail. Mike slowed hips as he felt her stop grinding on his dick.

"OK, now I want to see how much cum Mike has stored up in those huge balls," his step-mother requested.

"Sure thing. Come over here," Stacy instructed. She turned and sat in one of the metal office chairs and paced her hands under her tits and offered them up to him. Mike knew just what to do and he slid his pale slippery cock between her dark soft breasts and bucked.

"Don't let us down, Mike. I want you to dump all your cum on my big tits, ok?" Mike did his best to hold off but he eventually couldn't take the overwhelming sensations running through his body and finally let out a fountain of hot white cum that cascaded down the sides of his erection and across Stacy's breasts.

"Oh my god, Mikey!" she exclaimed with another wide-eyed look as another pulse in his penis sent a shot of semen into the air and onto her chin. As the rest of the semen oozed down his shaft and joined the rest of his ejaculate pooling on her breasts, Stacy leaned forward and sucked hard at the tip of his dick. His knees buckled for a moment as he felt the suction empty his aching penis.

"Well done," his mother complimented from behind her desk. She reached into another drawer and pulled out a box of wet wipes that she offered Stacy across the desk. Mike tried to catch his breath while Stacy cleaned up his creamy gift from her breasts and face.

"I'd say you two are ready for this afternoon."

***

The sun beat down on Stacy and Mike as they stepped out of her car and onto the quiet sandy beach entrance that afternoon. They each carried a backpack with their towels and swimsuits inside.

"Hello, Mr. and Mrs. Diaz?" Stacy greeted the beautiful light tan skinned couple standing at the base of the stairway that led to the beach.

"Please, call us Gloria and Santiago. Otherwise you'll make us feel old," Gloria laughed as she pecked Stacy and then Mike on each side of their cheeks.

"Definitely. Well, I'm Stacy and this shy young man is Mike and we just thought we'd hang out a bit and see if we can convince you to buy that house."

"Sure, let's just see where things go, shall we? I think there are changing rooms just up the hill," Santiago offered as the group began their short climb. Mike could nearly see up the back of Gloria's short yellow sundress as he climbed behind her. Every few steps, one of her thick bouncy ass cheeks would escape the bottom for a moment, only to slide back out of view.

The men and women split up when they reached the changing houses. Mike followed Santiago into the men's side. Santiago dropped his small bag onto a bench that ran around the wall and then stripped off his khaki shorts and t-shirt. He wasn't shy about parading through the room with his low hanging uncircumcized penis dangling between his legs as he headed to the urinal so Mike decided now wasn't the time to be modest, either.

After Stacy and Mike escaped the office for the day, Mike used the opportunity to ditch his tie and coat. That meant he only had to pull of his pants, briefs and shirt before he was standing naked in the changing room.

"You must work out," Santiago remarked with a nod to Mike's ripped abs as he returned to his bag to pull on his small blue speedo. "Say, you ever, uh, with her?" Santiago motioned with his hands, giving a clear indication of his meaning.

Mike couldn't help but blush as he pulled up the small trunks his step-mother had picked out for him.

"Ah, you dog. Tell me her tits look as thick and juicy as I think they do," Santiago said as he continued to carve up the air with his hands.

Mike laughed. "If he only knew the truth of it," Mike thought.

Santiago whistled when they caught sight of their companions outside the changing rooms. Stacy wore a throwback bikini with cheetah print bottoms that covered her bubble but, extended up over her curvy hips and stopped just below her belly button. Gloria had changed from her sundress into a white monokini whose straps barely covered her small pointed breasts

Mike and Santiago followed the women down the path to the beach, watching the women's asses bounce and sag as they walked. When they reached a smooth patch of sand with a wide view of the roaring surf, Santiago pulled a blanket from his bag and spread it on the ground.

"You know, there's no one else here, I don't think I need this," he explained as he reached one hand to his waist and stripped off the small speedo, unleashing his manhood to Stacy's delight.

"Now you," Gloria said, looking at Mike as she ran her arm around her husband's waist. Mike knew this would be expected of him at some point, just not so soon, but he dropped his trunks and let Gloria and Santiago take measure of his thick penis which was resting on top of his bulging testicles.

"How nice," Gloria complimented him. "You're not bisexual are you?" Mike froze for a moment.

"Not that I know of," he said, trying to play it cool.

"That's too bad. I think you and my husband would look so beautiful together. But, this will do. Sorry, I wasn't sure what to think when you're mother offered you to us at that party. Your father seemed so open."

Mike's head was suddenly spinning at the idea that his father had a wild side under that stiff exterior. He'd already seen him paddle Maria today and now he had discovered he might not just play with women. The sight of Gloria pulling her straps away from her small perky nipples was enough of a distraction for now, though. She stripped her unikini away from her body and let Mike take a good look at her dark brown nipples, thin waist, and wide hips. She turned around, letting him stare at her smooth thick ass as she swayed back and forth. Her long curly brown hair flowed with the breeze.

"My turn," Stacy announced. She reached to her back and unhooked her white strapless top and let it slip down over her breasts. It fell to the blanket at her feet and she reached for the bottoms. When she was finished, she threw her arms in the air and spun in a circle so their companions could get a look at her bare body.

"Shall we swim?" Gloria asked. The foursome jogged to the water's edge. The ocean water was cool on this early spring afternoon and Mike felt genitals sting as they sank into the surf.

They waded out into the waves then swam a short distance until they reached the sand bar. Santiago reached the bar first, popping up and throwing his arms up triumphantly. Stacy was just behind him, grabbing him by the waist and spinning him around as their feet splashed in the surf. The tide was moving out so they found themselves only shin deep in water at this distance from the beach.

"Refreshing, no?" Santiago asked as the group caught their breath.

"Not as refreshing as this," Stacy replied. She slowly bent to her knees and ran her hands down his thighs while she began to tease his dripping penis head with her tongue.

"Do you mind?" Gloria asked as she ran a hand down Mike's slippery chest.

"Of course not."

She crouched, sliding her hands around his back and cupping his butt with her hands while she used her lips to suck at the tender skin inside his thigh. Her mouth drifted up and around his undercarriage, finally finding the soft skin at the base of his hairless testicles. Mike sighed and looked downward to meet her eyes.

Gloria continued her oral assault on Mike's balls while he let his attention drift over to Stacy and Santiago. The couple had shifted into a doggystyle position facing Mike. Santiago was pumping his hips into Stacy's ripping behind while her hefty breasts hung below her chest and her nipples kissed the top of the water with each drive from Santiago's hips.

Suddenly, a wave crashed into the sand bar. A small wall of water crested over Stacy and Gloria and into Mike's side. It only fed Santiago's vigor as he sped up when the water subsided. Stacy let out a roar and Gloria laughed as she wiped the salty water from her eyes.

"Let's try something else," Gloria suggested. She stood, turned her back to Mike and then bent into a downward dog position. Mike grabbed his stiff manhood with one hand and used his height advantage to drive himself into her dripping wet opening.

"No. The other one," Gloria said, turning her head to smile devilishly up at Mike.

After pulling himself from Gloria's pink folds, Mike slowly pressed the tip of his flushed penis head into her light brown opening. His shaft was lubricated by Gloria's vaginal fluids and easily slid inside her until the base of his shaft found a home between her butt cheeks.

While Gloria raised one hand to her folds and pleasured herself, Mike thrust himself into her tight asshole. Her plump bottom bobbed and rippled with each thrust.

"Faster... deeper..." she begged just as Mike felt his legs cramping from an extended period of driving his hard shaft down into her tight opening. He pressed up to his tip toes and used his weight to drive even deeper into her anus and felt his full shaft engulfed by her opening.

"That's it!" Gloria cried out as he continued his thrusts and felt her rectum tighten at the base of his shaft. She trembled and cried out again before her body softened and she gently pressed his thigh away from her bottom with one hand.

Stacy and Santiago were still splashing away in the shallow water in front of Mike and Gloria. It looked like Stacy was on the edge of an orgasm, as her face began to contort and her eyes clenched.

"Give it to me, you Latin fox!" Stacy begged and Santiago redoubled his efforts behind her. Finally, Stacy bucked and wailed as her orgasm overtook her body until she slumped to the top of the surf.

"Now it's your turn," Gloria smiled up at Mike. She beckoned for Santiago and Stacy to join them and helped Stacy ease down into the water on her knees.

"I want to watch both of you cum onto these magnificent breasts," Gloria requested.

Santiago wasted no time coaxing his manhood back to full mast and then stroked it aggressively in Stacy's direction. Mike clenched his fist around his hard pole and stared down at Stacy's massive tits for the second time that day. Santiago went first, pumping a rope of semen across her chest and then on top of each of her dripping wet mammories. Mike followed with an explosive shot that passed overtop of Stacy's breasts and onto her shoulder before draining the rest of his semen on top of the creamy white base laid down by Santiago. Gloria lapped away their gifts with her tongue and then swallowed. What she couldn't finish, she cleaned away with the salty ocean water.

"Yay," Stacy applauded from her knees after the group had finished. The foursome swam back to the beach where they dried off with towels from the bag Santiago left behind.

"You two are amazing. Thanks for that. Should we go sign some papers?" Stacy asked after the group was dry.

"Well, that was fun. But I think we are still trying to keep our options open," Gloria sheepishly responded.

"What does that mean?" Mike naively asked.

"You're just going to screw us and then screw us over on the house?" Stacy followed up.

"I'll tell you what, don't call us, we'll call you. OK?" Gloria called back over her shoulder as she and Santiago grabbed their belongings and then scampered off toward the changing houses.

"What the fuck!" Stacy yelled with a shrill timbre to her voice. "This is bullshit!" She crossed her arms across her bare chest. Her nude body trembled while she fumed.

"What do we do now?" Mike asked.

"We fucking get the fuck out of here. I can tell you that much."

The pair dressed and returned to Stacy's car. They stopped at a drive-through for lunch and ate in silence on the long ride back to the office.

"Don't say anything to your step-mom when we get back, ok? I'll handle this. I'll try to make it right." Stacy's orders couldn't be clearer to Mike. She was still fuming mad and he knew her well enough to understand she didn't want any suggestions from her best friend's little brother.

***

Mike hid out in the basement after work, playing video games and eating dinner from the basement kitchen to avoid the rest of his family. He felt confused and a little disappointed about how things ended with the Diazes. Hadn't he done his part? Were they disappointed in Stacy and his performances or were they just using them to get off in the first place?

He headed to bed early so he could sleep off the anxiety about what his step-mom or dad would say about his failure. The expectations for him were always set high, whether in the classroom or on a soccer pitch. They wouldn't be happy that he let this deal slip through his fingers.

Thoughts of Gloria's body bent over in front of him continued to dance through his head as he tried to sleep. He recalled the feeling of her tight asshole gripping his shaft as it dove into her time and time again. His body responded to the memory and he could feel his manhood pressing up against his boxers.

"Mike, are you asleep?" came a whisper from behind the door. The knob slowly turned as Mike sat up and pulled the covers up to his chest. Hillary's eyes shone in the darkened room as she pressed the door open and then quietly closed it behind her. The combination of streetlights and moonlight allowed Mike to see she was wearing short shorts and a tank top as she crossed the room to slip under his sheets.

"I heard the bad news," she whispered. "I hope you know this isn't the end of the world.

Mike sighed and hung his head.

"Look, maybe I can cheer you up," she offered and her hand slid up his knee and across his thigh. "I heard mom was in the room when Stacy gave you your little bonus from the Princeton job. That's her trick: 'quality control.' I think she gets off on it"

Mike's shaft jumped at the mention of his step-mother. He pictured her massive breasts being held back by her blouse earlier in the day and remembered the way she egged him on with Stacy. It really turned him on to have her watching while they fucked.

"Oh, my. You really liked that, didn't you, you dirty boy?" He could feel Hillary's hand make his penis harden through his boxers and she pulled the waistband down and gripped his manhood tightly.

"I think maybe you want to fuck my mom, is that what you want? After all these years, now you're all grown up and you want to see those big titties?" Hillary whispered in his ear as her hand rhythmically pumped on his thick shaft. "Do you want to slide this big dick inside her wet pussy? Is that what you want, brother?"

Mike couldn't lie to himself: Hillary had hit a sweet spot, both with the slow long strokes of her hand and with the soft dirty talk she whispered into his ear. He slipped a hand under her tank top and cupped her dainty breast. It wasn't anything close to what he imagined her mother's breasts felt like but it would do.

"You know what I think?" HIllary continued, "I think I'd like to watch you and your dad fuck my mom. Maybe at the same time? Would that turn you on?" At this point, he would agree to anything Hillary said so long as her hand was riding his hard dick. He closed his eyes and pictured her mom riding his dad's thick hard meat and felt pre-cum dribbling from the tip of his throbbing penis.

"Oh, that pre-cum feels so slick and warm in my hand, Mikey. Why don't you slide that big dick inside me?" She pulled her shorts off and climbed on top of Mike and he felt him inside her slick opening.

"Yeah, you're so big. Just like your daddy. I want to see this big cock and his big cock sliding inside my mom's juicy pussy at the same time," Mike could feel his step-sister constrict her opening around his shaft and he was pumping for all he was worth. The thought of sharing his stepmother with his dad all while feeling Hillary bouncing on his aching erection was too much for him.

"I want to watch those big wet cocks rubbing up against each other while they slide in and out of her hole. Then I want both of you to pull out and cum all over her hairy pussy. Can you do that for me Mikey?" She almost didn't need to ask, Mike couldn't contain himself after letting Hillary's imagery wash over him. He flipped his step-sister's long slender body to the bed, pulled his dripping cock from her slick opening, and pumped his shaft in his hand until he coated her soft pink folds with a stream of his watery white semen. He fell into her arms with exhaustion. After everything he'd experienced that day, suddenly his step-sister's embrace was the only thing that made sense.

"Feeling better?" She asked after he lay with his chest pressing up against her small breasts for several minutes.

"Definitely. Thank you for this. I owe you one."

"Oh, I intend to collect. Trust me."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.Over the three nights that followed, Mike no longer received late night visits from Hillary. He found himself persona non grata around the house as he ate breakfast alone and spent as much time as possible in the basement avoiding the rest of his housemates. He felt like he had flown to high too quickly - that he had failed his crash course into the family business and would spend the rest of the summer and next year at school mulling over his failures.

When Friday finally rolled around, he was just thankful that the work week was finally ending. Thankfully, his father had not relegated him all the way back to office errand boy but he certainly was not invited to anymore private meetings in his father's corner office. Hillary never came by to spring him from his boredom and the only contact he had with Stacy was bumping into her in the hall at home. She gave him pity looks as they passed. He wasn't sure if they were apologies for failing him or if she felt he had let her down on the Diaz deal.

"Michael, please come to my office," came his step-mother's voice over the intercom. He was startled after finally settling into his work. The last time she requested a meeting, he left turned on, frustrated, and pretty confused.

The office workers cat-called and hollered after Mike from their cubes as he strolled past the bullpen to his step-mother's office.

"Ooooh... somebody's been a bad boy," teased one voice. He wasn't sure if they had any idea about what had transpired between Hillary and him but he felt shame all the same.

"Close the door and have a seat... if you can," Tamara teased him when he appeared at her open office door. He had recovered from the discipline and made a point to flop into one of the metallic chairs in front of her desk to demonstrate his recovery.

"I think we've been a little hard on you, Michael," She said, using his family name. "I think your father and I believed you were ready for action. You're a strapping young man, and I've seen the women you run around with on your Instagram posts so I know you know your way around the ladies. But, here's the thing: what our clients really need is a custom experience, you know? They're looking for something they aren't already getting. Do you understand me?"

"Sure."

"Good. I know my daughter is a trouble-maker but I didn't expect she'd drag you into such a clear violation of our trust. What I'd like to do is give you a second chance. Maybe this wasn't your fault at all. Maybe we threw you into the fire a little too quickly. Correct me if I'm wrong, but I think our little discipline session the other day actually excited you a little?"

He stared at his lap silently for a moment, trying to find the correct answer. "Uh, I guess so," he finally muttered.

"That's fine. We can work with that. You're just young. You have a lot to learn. I'm kind of glad you and Hillary are experimenting together. You're not related, after all, and you can keep it safe that way. You know? On that note, do you think you're willing to... keep learning. To find out more about yourself and how your father and I cultivate our clients?"

"Of course. Whatever you need," his eyes perked up to look Tamara in the eyes, hopeful that she was about to present him with an opportunity to regain his standing in the business.

"That's nice to hear. Listen, there's an event later tonight. Hillary usually helps out with it. It's a charity auction, of sorts, at one of our biggest client's estate. We told her we'd help her find eligible singles to auction off." Mike's heart started pounding. What was Tamara getting him into, now? "It's all in good fun, everything's above boards. Unless you're ok with it getting a little naughty? I think I know you well enough to know you like bending some rules, no?"

Mike swallowed hard. "I don't see why I'd stop now?"

"That's my boy." Tamara replied. She stood up and circled around the desk and leaned back into the desk. She tossed her long dark hair behind her, and let him get a good look at the thick round mounds that formed underneath her blouse and vest. "Here's what I need from you," she said and began to run her toes up the inside of his slacks. "Go on home and get some rest and a snack. Then get good and cleaned up. I mean all over," she said, stressing the "all". "Then put on the most stunning suit you've got in your closet and we'll have a car pick you up at 8:30."

"Sure. I can handle that," Mike replied. He closed his eyes and nearly melted as her toes danced up closer to his crotch.

"Oh, and don't get too attached to the suit," Tamara said as she tapped him on the head of his dick and then spun back around to slip her feet into her shoes. She stood, checked her blouse and skirt to make everything was in place, and then opened the door.

"So I'd like you to go home and chew on that," she announced with some gusto so the rest of the office could her as Mike exited the door and didn't look back.

Mike did as instructed: returning home to take a long nap, grab some food, and then shower up. He found one of his sister's razors and used it to trim up the pubic hair on his testicles and shaft of his penis. He always thought women's razors were so much softer on his sensitive areas. After he exited the shower, he made sure to inspect himself in the mirror, looking for any hair growing in any inconvenient locations and then toweled off.

It was hard to keep his hands off his cleanly shaven cock. He started to get hard everytime he even thought about his step mother's overflowing cleavage and the chance to use his own physical gifts to make her happy. He wondered what she had meant when she told him not to get "too attached" to his suit.

Around that time, he heard some clamoring in the hallway. He wasn't alone in the house anymore.

"Yeah, I thought she did a great job with my hair," he heard his step-sister tell someone down the hallway.

Mike took his time dressing, making sure each button was just in the right place and that he picked cufflinks that were just right for this suit. The whole process took until around 8 pm, so he headed downstairs and helped himself to a finger of whiskey from his father's liquor cabinet. No one was around and, in any case, he didn't think his father would object after everything he knew about his son at this point.

The sun was just starting its descent over the hills in the backyard when Mike heard the sound of heels making their way downstairs. He turned to the doorway to see Stacy saunter into the room. His mouth hung open at the sight of her black lacy gown that hugged her hips and showed off her full chocolatey cleavage. Her nipples and areolas were covered by black and white fabric that zig zagged across her chest. Behind Stacy, his sister strutted into the room in a black leather bodice that was cinched up tightly around her apple shaped breasts and a mini-skirt that showed off her long tone legs.

"You got enough of an eyeful yet, friend?" Stacy asked.

"Oh, I just didn't know you all were going, too." Mike responded

"You think I'm missing out on the event of the year? I'd be crazy. Especially since I made enough off your family's name to do some bidding for myself this year, " Stacy explained.

"What about you?" Mike asked his sister.

"Nope. I'm back on the block, just like you. It's more fun this way anyway," she said as she helped herself to a handful of Stacy's plump ass. Stacy smacked her hand away and they laughed at each other.

There was a honk in the driveway.

"That's us. You coming?" Stacy asked as the women walked away holding their small hand bags. Mike downed his whiskey and then tried to look confident as he followed her bouncy ass out the doorway.

In the limo on their way to the destination, the ladies tried to give Mike a pep-talk.

"Just have a good time, little brother. Don't let all the money people are paying to ogle you intimidate you," she said, balancing a martini she made from the limo bar in one hand.

"Straight couples pay a ton to bid on some time with women but a lot of the men usually get picked up by gay couples who just want to flirt and have some drinks. Just be cool," Stacy coached him. Mike hadn't considered that idea but at least he had the head's up so he could draw boundaries, if needed.

When the limo arrived at its destination, Mike looked through his window and recognized it immediately as the estate owned by one of the fast rising biotech venture capitalists in the area, Meg Tillery. The car pulled through the arched gateway up front but, instead of veering off to the roundabout in front of the massive home, it continued past the mansion. Stacy and Hillary exchanged an excited look as the car pulled down a hill next to the mansion and then turned into a service entrance at the back.

Mike jumped a little when a masked face appeared in the window of the limo. He didn't expect this to be a costume function. It turned out, the man in the window was just an attendant. He opened the door and helped Hillary and then Stacy step out. Mike followed, slipping the man a ten dollar bill as he stepped out of the car but the masked man simply stared at the bill in his gloved hand.

"Right this way," a smokey female voice called. Mike turned to see a tall stunning woman standing the doorway to the house. She wore a tight black mini skirt that hugged her shapely hips at the top and extended into some frills at the bottom. A tight corset hugged her ribs just above her belly button and showed off her tan abdomen and teased her big round breasts. She held a masquerade mask up to her face but he was pretty sure this was Meg's Filipina trans wife, Jasmine.

"Welcome back, ladies," Jasmine greeted Stacy and Hillary with intimate hugs and kisses for each. Mike liked watching her large cleavage press up against Stacy's. "And who do we have here?"

"This is HIllary's little brother, well step-brother, Mike," Stacy explained.

"Jasmine," the tall woman introduced herself by holding her hand out, palm down.

"Enchante," Mike said, getting into the spirit of the party, with a peck the the soft skin on the back of her hand.

"Oh, I like this one. Can I keep him?" Jasmine playfully asked.

"Not if I outbid you," Stacy joked. The group had a laugh and then Jasmine led them in through the doorway.

Since Stacy was bidding at the auction, she followed the male attendant down a hallway to their left and out of sight as Jasmine continued to lead Mike and Hillary straight ahead. When they reached a black door, Jasmine knocked and then entered after she didn't hear any objections. Inside the dim room, padded benches lined the walls. All along the benches sat men and women of various ages and body types, chatting or checking their phones. They all wore similar cloaks and feathered masquerade masks. Against the far wall were two tall transparent that screens that were lit up from the other side. The lights allowed people in the room to see the outlines of the bodies of the people changing clothes on the other side. Mike could see there was a rather well hung man changing on the left while the side of a woman's curves were silhouetted against the divider on the right.

"You aren't shy are you?" Jasmine asked when she caught Mike staring at the dividers.

"Not that I know of," he responded.

"Great, then you won't mind if I help you change." Jasmine held Mike's hand and he reached back to grab Hillary's just before Jasmine pulled him away. The man and woman appeared from behind the screens with cloaks falling over their shoulders and down their chests and went to find seats as Jasmine led onward.

When the threesome arrived behind the screen, Jasmine held up a hand for Mike to stay while she turned Hillary around. They stood in profile to the screens while Jasmine untied Hillary's bodice from behind. Jasmine dropped the bodice to the floor and Mike caught a glimpse of the lean muscles in Hillary's pale nude back. Jasmine pressed her pelvis into Hillary's tight butt and spooned the smaller woman as she slowly pulled down Hillary's leather skirt. She pulled back to admire Hillary's tight butt and ran her finger down her thong.

Lastly, Jasmine turned Hillary to face Mike. His older sister chuckled and then shyly placed her arm across her small breasts while Jasmine crouched near the floor. Mike admired the woman's apple bottom that was cupped by her tight dress and watched her slip off Hillary's panties. Her pink folds were a sight for sore eyes but soon she was covering them with her free hand. Jasmine quickly folded up Hillary's clothes, placed them through a slot in the wall behind the screens and then received a cloak in return. She helped Hillary fit the cloak over her shoulders and it fell down to her waist, covering all of her fun parts from view. There was a number pinned to the inside of the cloak so that they could match it to Hillary's clothes when she left. The cloak also came with a white feathery mask that Hillary slipped over her face.

Now it was Mike's turn. He slipped off his jacket and started to loosen his tie as Jasmine approached him and lowered herself to her knees. She pulled his fly zipper down and reached her hand inside and through the opening on his briefs to pull his engorged cock out from its sheath. She let it hang in front of his pants and admired it, smiling up at Mike as she gave it a little tug.

Satisfied with his size, Jasmine removed his pants, starting by unbuckling his belt. She pulled the Italian leather belt off his pants with a zip, unbuttoned his waist, and then let the pants drop to the floor. Mike stood there, cock out in front of his step-sister and this hot stranger while he finished pulling open his shirt. Hillary golf clapped her approval while Jasmine helped him gather all of his clothes and exchange them for a cloak for himself.

The cloak was heavier than it looked but soft on the inside so Mike didn't mind it at all. Hillary helped him find a seat on a bench near a couple that looked older than Mike and his step-sister. The thick and busty woman wore emerald earrings that complimented her blazing red hair and Hillary and Mike traded an "I'll show you mine if you show me yours" moment with the couple. Thankfully, they kept their identities a secret so they didn't have to share how they knew each other.

Slowly, the room thinned out as couples and individuals were led out through a door across the room from where they entered. They were led away by a topless woman in gem studded panties and a an elaborate sparkling headdress and an Adonis-looking male companion in a white thong and gem studded masquerade mask. Finally, she beckoned for Hillary and Mike. They stepped through the doorway but the large dark skinned man stopped them.

"We need to add these before you continue," the woman explained and she attached a studded collar around each of their throats and then clipped a leash to each of them. The man led Hillary while the curvy topless woman pulled on Mike's leash. After passing down several twists and turns in a dimly lit hallway, they arrived at a backstage area. Mike's companion stopped while Hillary and the man continued onward. When Hillary and the man passed through the small opening in the curtain, Mike could hear clapping. It was hard to make out the voice of the auctioneer but it sounded like a woman.

After several minutes passed, Mike heard another round of clapping. The large man and Hillary arrived back through the curtain but peeled off in the opposite direction. Hillary looked back and blew a kiss in Mike's direction before following the man through a door on the other side of the stage.

The topless woman holding Mike's leash pulled him roughly and he felt butterflies in his stomach as he approached the break in the curtain. A warm round of applause greeted Mike when he took his first steps onto the long black catwalk. The hot stage lights beat down on him but he could just make out some of the faces sitting in the darkened room below it. His topless companion pulled up and they waited.

"Up next we have this strapping young man, the youngest companion at auction this evening..." Jasmine was holding a microphone at the far end of the catwalk. She smiled at him as she turned to face him. "Let's see what he's made of, shall we?"

With that prompt, the topless woman turned to Mike and unbuttoned and pulled back his cloak. It fell to the catwalk and he was completely naked in front of a room of strangers. He tried to remain confident, lest his manhood shrink with shame in front of all these people. The topless woman led him forward, to parade him in front of the bidders. He didn't notice anyone being offended as he tried to look at the expressions on the bidders faces in the front row.

"We will open the bidding at ten thousand dollars." Jasmine placed a finger to her ear and Mike realized she was receiving information about the bidding from someone else through an earpiece. It would be pretty hard to see all the bidders in this lighting, but Mike guessed that was part of the point.

"We have twelve thousand, can I get fourteen thousand for the companionship of this former standout athlete?" Jasmine asked the audience. Mike felt his balls drop just a little more at the compliment to his athletic prowess. His thick shaft was bouncing off his thighs as he walked and listened to the auction continue.

"We've got a bid for twenty thousand dollars. A new single bid record. Can anyone top this? Remember folks, all of the proceeds from tonight benefit a great cause. Going once... going twice... sold. OK, I think you know the drill, proceed to the door on my right to take things from here," Jasmine said with a joyful tone. The crowd cheered wildly as Mike followed the topless companion back to the stage curtain. He picked up his cloak and pumped a fist on the way through the curtain to acknowledge the crowd.

He was floating when they reached the dark area behind the curtain.

"Nice haul," his leash-holder commented while she helped him re-attach the cloak. She led him to the backstage door he had watched Hillary exit through but a voice called to them before they could leave.

"Hey, wait up."

It was Jasmine, scurrying after them as best she could in her stiletto heels.

"Don't you have a job to do?" the topless companion asked.

"I handed it off. I've got a special interest in this one," Jasmine commented as she took the leash from the other woman and then pulled Mike through the stage door. "I've got a special destination I need to take you to," she explained.

Mike followed Jasmine, watching her short leather skirt sway just inches below her well developed ass. Her long brown hair was pulled straight back and fell to the middle of her lean but well-defined back. She pulled him into an old timey elevator with a rickety gate serving as a door and a handle Jasmine pulled to indicate their destination.

The elevator slowly descended a level and Jasmine pulled the gate to the side and then pulled him along. "You ready to meet your benefactor?" Jasmine asked before pulling Mike through a set of black curtains

He almost laughed when he saw who was waiting in the dungeon themed room. The three figures sitting on the end of a king sized bed pushed up against the opposite wall removed their masks. They were his father and step-mother with none other than the Meg Tillery seated between them.

His father wore a dapper looking suit while his step-mother wore a gown with a plunging neckline that revealed the tops of her thick tan breasts.

"Hello, Michael," Meg stood as she spoke. She wore a tuxedo with a black bowtie. The jacket's opening neatly framed her small breasts. Mike guessed she stood about five-six in her heels. "I really appreciate you volunteering for our auction." She carried a riding crop in her hand that she patted on the other as she spoke. "You see, once you step mother showed me your photo and told me you'd be here, I knew I had to keep you for myself. Jasmine, shall we inspect the merchandise?""Sounds good," Jasmine said with a small squeal of excitement. She turned to Mike, unclasped his cloak and let it drop to the floor.

"Now help me get comfortable, ok sweetie?" Meg said as she crossed to the space between the bed and Mike.

She held a riding crop in her right hand and leaned it against her leg as she pulled off her tuxedo jacket. Jasmine knelt in front of Meg, helped her get out of her open-toed heels before pulling down her zipper and unbuckling her belt. As Meg unhooked the black studs holding together her tuxedo shirt, Jasmine pulled her pants to the floor.

Soon, Meg's shirt joined her pants on the floor and she was standing in the middle of the room in black stockings that rose to her upper thighs where they were clipped to a garter belt. A pair of lacy black panties covered her mons pubis and a white halter top corset revealed her thin waist while supporting her cute little breasts. She was incredibly petite, with few curves and a boyishly feminine face. The short black hair on her head was coiffed into a wavy part to one side.

Meg picked up the crop and continued her inspection. "I like these big muscular thighs," she commented as she tapped the outside of Mike's left thigh while she circled him. "Strong glutes," she observed and Mike felt the bite of the crop against his left butt cheek. "Good composure, too."

MIke felt the riding crop pull his butt cheeks apart as Meg took a good look. He looked straight forward, while trying not to make direct eye contact with his audience. The crop continued its circle around his lower abdomen and then around to the middle of his stomach.

"And here's the coup de gras, this beefy handsome looking cock. I guess the apple doesn't fall far from the tree," Meg observed. "I'll tell you what, I'm going to have Jasmine take your parents away for a moment, OK?" With that command, Jasmine crossed the room and led his parents out through the opening in the curtains to the left of the bed. Meg grabbed Mike's collar and led him to a large "X" shaped cross to his right. She pressed him back into the wooden boards and then used the clamps attached to secure his wrists and ankles.

"Here's the deal, I promised your step-mother I'd make their event tonight a big hit. But part of the deal was that, if I was going to pay this much for you, I'd want a little more with it."

As Meg stepped back, the curtains on the other side of the room parted. Jasmine led his father and step-mother out by leashes that matched his own. Otherwise, they were both completely naked. His father's burly chest gave way to thick abdominal muscles and a large thick shaft bounced between his thighs. It really did look like Mike's. Mike could feel a shiver run through his body when he looked at his step-mother, though. Her thick dark hair curled across her shoulders and plunged down to her collar bone. Her round fleshy breasts hung partly down her chest and swayed as she walked. At the apex of her tan thighs was a delicious looking bushy tuft of pubic hair.

"Bring them on over," Meg called to Jasmine. She parked the middle-aged couple directly in front of Meg and Mike."What a pair.". She circled Mike's father and step-mother now, riding crop at the ready. "Tamara, why don't you get down and show your husband some appreciation," she ordered with a crack of her riding crop to Tamara's ass.

Mike's step-mother slipped down to her knees and raised a hand to stroke his father's soft pink cock until it began to rise.

"Have you ever watched your step-mom suck a cock?" Meg asked. She circled around behind Jasmine and slipped her hands up under her skirt. Jasmine's lacy thong fell to the floor at her feet and she stepped out of her heels and then out of the leg holes of the panties. "How about two dicks?" Meg asked and then slid Jasmine's short skirt down her thighs and to the floor revealing her massive ochre colored penis.

Jasmine saddled up beside Tamara and Meg continued undressing her wife, unhooking the corset and letting Jasmine's thick bolted on breasts fall from their support. Tamara turned her head and placed her lips around Jasmine's thick cock while she continued to play with her husband's growing penis with an outstretched hand.

"