tagIncest/TabooLearning the Family Business Ch. 04

Learning the Family Business Ch. 04


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?"


"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?"

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