Right or Left? Ch. 03

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Continued sexual journey of brother and sister and friends.
7.7k words
4.7
42.2k
69

Part 3 of the 8 part series

Updated 06/08/2023
Created 08/21/2017
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Thanks once again for your support and votes on my incest saga. The story continues with brother and sister Jeff and Wendy and her girlfriend Kylah as they are getting prepared for their upcoming spring break vacation. Now that they are sexually intimate with each other the anticipation of having an unencumbered week together is driving them wild with desire. Sherry, a new character, is introduced to the story line.

If you are bothered by grammatical errors to the extent you can't see past them and enjoy the story then perhaps this story is not for you.

This story may contain peanuts so if you are allergic to incest, anal, oral, threesomes, rough sex, humiliation or sex, in general, please do not go any further.

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Reflections

The day was winding down it was six pm and Jeff was sitting in his real estate office thinking for the hundredth time about the dramatic twist his life has taken in such a short time. He shook his head as if that would make it all better and stood up to look out his window. He could see all the cars below going by, strangers going home to their loved ones.

His reflection on the glass showed the figure of a young man in his prime, tall, dark-haired and trim. His expensive clothes representative of his success. But right at this moment, his confident exterior didn't match the frown on his face nor the butterflies in his stomach. Deep inside he knew his whole future hinged on the strength of two women to keep a secret and all it would take is one slip for his life to explode into a million pieces.

It would be nice if he could blame someone else but he accepts the current trappings are all his fault. The night he discovered his sister Wendy masturbating in her bedroom he could have left unnoticed but instead he stayed. What ensued was a weekend of making love, fucking and doing things to each other that no brother and sister are supposed to do.

When the weekend was over and their parents came home he thought their brief affair would be over but neither Jeff or his sister could bear to end it. The sex was too incredible and they kept on getting deeper and deeper into lust and deception.

When Wendy asked her brother to chaperone her and her girlfriend Kylah on their spring break getaway Jeff reluctantly agreed and with Kylah's parent's approval of him their trip was confirmed. The three of them met in a coffee shop to plan the trip and when Kylah showed her submissive side to Jeff he took advantage of her in a swimsuit store while he bought her several tiny red bikinis.

By far the biggest bombshell to fall on Jeff was when Wendy broke her vow of secrecy and disclosed to Kylah that she and her brother are lovers. Kylah swore her secrecy to them but Jeff knew a secret was only a secret if everyone kept it. There was little he could do at that point so he went with the flow and to celebrate their new bond they had an amazing threesome in Jeff's bedroom. The sex was incredible and a good prelude to what they could look forward to on their vacation.

Distracted by the cars again he knew it was time to go home to his loved ones, appointments were done for the day, his parents and sister were waiting for him. His dad had called him earlier in the day to make sure Jeff could be at supper tonight to share some good news.

Before he turned to leave he noticed the reflection in the glass of a woman in the doorway behind him He recognized it was Sherry, one of the office agents, just as she knocked on his door.

"Hi Jeff," said Sherry, "sorry to bug you but I was wondering if you were free for a couple of minutes?"

Jeff turned to face Sherry taking in her unusual business attire. Sherry was known for her outrageous outfits that projected the image of a street prostitute more than a professional real estate agent. Jeff couldn't understand why Glen, his managing broker, never said anything to her but guessed it was because the old guy enjoyed the view.

Today Sherry had on a bright pink tank top and judging from her extended nipples no bra, a short white skirt similar to what a woman would wear on the golf course and white high heel pumps. Her long blonde hair was pulled back into a ponytail and she had twice as much makeup on as was necessary. He guessed she was in her mid-thirties and desperately trying to pass as a twenty-year-old.

Before Jeff could say a word Sherry marched into his office and sat in one of the client chairs flashing her white panties to him when she sat down.

Sherry was one of those agents who didn't do a lot of business and liked to talk with everyone about the reasons why. Rather than sitting in his chair he came around the desk and sat on the desk edge right in front of Sherry. His thoughts were to get inside her comfort zone and maybe just maybe she wouldn't stay long.

He perched his bum on the desk and with his legs spread wide he looked at Sherry, "So, what's up?" he said.

Sherry lost her concentration when Jeff sat on the desk between her and the chair. She could see the shape of his cock down the side of his grey slacks. She never suspected that young Jeff was so well endowed.

"Um, well, um," Sherry stammered with a beat red face, "Glen said you were going on a vacation and looking for someone to cover your business."

Jeff could see Sherry was staring at his crotch and her nipples had gotten even bigger than when she came in.

"What makes you think you're qualified?" said Jeff as he looked from her eyes to her breasts letting her know he was sizing her up too. "From what I see on the deal board you haven't made very many sales this year."

"I know! It's not my fault the market is just crazy!" Sherry said. "I was hoping I could sell some of your listings while you were gone."

"Sherry do you want the truth?" said Jeff, when Sherry nodded he continued, "it's not the market, it's you."

Sherry looked at Jeff and her bottom lip started to tremble, tears welled up in her eyes, she tried to speak but all the came out was a small squeak.

Jeff hated to see a woman cry and he walked over to his door closed it for privacy then returned to sit on the desk in front of Sherry. He watched as her unencumbered breasts bounced up and down with her sobbing.

He waited until she semi-composed herself. "Sherry stand up in front of me," Jeff said abruptly.

He wasn't normally so rude but right now his mind was full of confusion over his own situation and he found his patience lacking. Sherry stood in front of Jeff wiping the tears away and in the process spreading mascara all over her face.

"When I look at you I don't see a real estate agent," said Jeff, "What I do see is a woman trying to look younger and flaunting her assets to everyone. I mean really, look at your nipples they are clearly visible and your skirt barely covers your ass. Perception is everything in our business and you are clearly sending the wrong message."

Sherry was in shock no one had ever talked to her like this before. Jeff was the number one agent in the office and his words hit home hard. She thought her outfits gave her an 'edge' in the business and her male clients seemed to like it although she did have to fight off some of them.

"Jeff," pleaded Sherry, "will you help me? I want to be as successful as you but I don't know what to do. Please! I will do whatever it takes!"

"Are you sure?" said Jeff as he stared hard into her eyes and then down her body. He knew he was letting his cock do the talking for him but he had to see if she really would do whatever it took, she really was a very beautiful woman. "Go lock my door and come back to me."

Sherry wasn't sure what Jeff had in mind but could guess it had to do with her body and sex. She could see there was no compassion in his eyes as he waited for her to make a decision.

The lure of success won out and Sherry turned and locked the office door and made her way back to Jeff. She stopped a few feet in front of Jeff. "Now what?" she said.

Jeff placed his hands on Sherry's shoulders, "are you sure you want this?" he said. "It's not too late to change your mind."

"I do Jeff," said Sherry, "I want it more than anything else in the world."

Jeff slowly squeezed her shoulders. "Opportunities come up when you least expect them and right now this is your chance. I am going to ask you some questions to see if you really are ready to do whatever I ask of you. If I think you are lying I will kick your ass out of my office. Okay?"

Sherry didn't hesitate, "yes, okay."

"Are you married?"

"No, I got divorced four years ago."

"Any kids?"

"No, just some nieces and nephews."

"Do you have a boyfriend?"

"No."

"Are you into girls?"

Sherry hesitated, "I tried it once in college but I like guys better."

"Why do you dress like a slut?"

Jeff watched another big teardrop slide down Sherry's cheek."I wanted to be different," said Sherry, "and it makes me feel sexy."

"Have you ever fucked any of the agents in the office?"

"No."

"Not even a blowjob?"

"No, Glen is always after me but I just laugh it off."

Jeff slowly puts pressure on her shoulders forcing her down. Sherry let Jeff guide her down and she presumed he wanted her to suck his cock. With a quick push backward she landed in the chair. She was both surprised and a little disappointed at the same time.

"Did you think you had to suck my cock?" said Jeff with a smile on his face. "Maybe later if you agree to my terms."

Sherry nodded her head as she looked up at Jeff waiting to hear his proposal.

"I need an assistant," said Jeff, "a buyer's agent who will work just for me. I will train you, give you all the leads and be your mentor. In return, all your commissions will be shared 50/50 and I will pay your office desk fee." Jeff waited for this to sink into Sherry's mind.

"You want me to be your partner?" said a surprised Sherry.

"No," said Jeff, "you will work for me and trust me if I think you are not committed I will fire your ass out the door. However, if you listen to me there is no reason at all why you can't make $100,000 or more your first year."

"You would do that?" said Sherry in shock. "For me?"

"Yes, but no more dressing like a slut," said Jeff, "you are a professional and you should act and dress like one. Are you good with that?"

"Oh Jeff, yes, yes, I will do whatever you want," said Sherry as she once more looked at the bulge in his pants.

"Stand up," said Jeff, "now put your hands on my shoulders."

Sherry stood up and placed her hands on Jeff's shoulders, she could feel the firm muscles under his shirt and blushed when she thought about the outline of his cock.

"Now, ask me to play with your nipples," said Jeff. He knew this was the turning point in their new relationship if she agreed then she would do whatever.

Sherry looked at Jeff and could feel her pussy getting wet. He was in control, she knew it and she loved it. He ex-husband had been such a wuss and that was part of the reason for their divorce. The sex was terrible and left her wanting more.

"Please Jeff," said Sherry, " pinch my nipples."

Jeff cupped her breasts in both hands, lightly rubbing her nipples with his thumbs through her top. Her hard nipples responded to his touch as he flicked them. He pulled her top up over her breasts and viewed them for the first time. They were round and full with big puffy nipples. He was going to enjoy playing with these whenever the urge took him. He rolled Sherry's nipples between his thumbs and forefingers squeezing them hard. He waited for Sherry to complain and when she didn't he squeezed even harder.

"Oh fuck," said Sherry, "that feels so good!"

Sherry was having a hard time standing still while Jeff pinched her nipples. Jeff had found her most sensitive area with his first touch. She was losing control of her legs and could feel herself leaning heavily on Jeff as he pinched and pulled on her nipples. She knew her panties were soaked.

Jeff twisted and pulled on Sherry's nipples, pinching them as hard as he could. Sherry's body was gyrating with her hips fucking an imaginary lover. Her head was now resting on Jeff's chest and her tits hung straight down. Jeff used her nipples as anchor points and lifted them up forcing Sherry to stand upright, he pulled even higher until Sherry was on her tiptoes. They were eye to eye now and Jeff could see the lust in hers.

"What will you do for me?" said Jeff.

"Anything!" said Sherry, "I'm your slut. Oh fuck I'm going to come!"

Jeff held tight to her nipples pulling and twisting them as Sherry's orgasm hit, when her legs gave out Jeff guided her to the chair behind her giving her nipples one final squeeze.

Sherry watched as Jeff undid the zipper on his pants freeing his hard cock. Her first thoughts were it looked perfect, just like Jeff.

"So, you like it rough," said Jeff.

"Yes," said Sherry, "my ex-husband was a pussy and wouldn't hurt me. He said I was sick."

"You're not sick, you just appreciate different things," said Jeff. "Now show me how a good you are at sucking a cock."

There was no foreplay, Sherry opened her mouth and sucked Jeff's cock in as far as she could. She gagged and moaned each time he reached into her throat. What little mascara that was left on her eyes joined the rest of her streaked face. She looked and acted like a true slut. Jeff had a hand on the top of her head but he didn't need to force Sherry she was doing it to herself.

She pulled her mouth off and looked up at Jeff. "Slap my face Jeff," she said, "slap me hard!"

Jeff grabbed her ponytail and held her head still, Sherry watched as he drew his hand back slowly, teasing her. The blow to her cheek was just what she wanted and needed.

"Harder!" she said, "Please!"

Three more hard slaps found their mark. Sherry had both hands in her panties fingering her pussy when Jeff thrust his cock back into her open mouth. He pushed in hard until he bottomed out using her ponytail as a handle he fucked her mouth. With no limits, he took his time as he didn't want to come too quickly. He used his cock to slap her face and smear her saliva around.

"Thank you, Jeff," said Sherry softly, "thank you."

Jeff would have never guessed Sherry's secret to be controlled and used roughly. She loved it. The harder he used her the more thanks he got from Sherry.

"Look at me," said Jeff, "look at me as I come in your mouth."

Sherry had her mouth open as Jeff stroked his cock, her tongue licking the underside. Her brown eyes were fixed on his blue ones when his cock erupted, the first load caused Sherry to choke until she swallowed, the second and third shot lay on top of her tongue. She waited with her mouth open, waiting for instructions.

"Swallow it," said Jeff, "then clean my cock."

"Thank you, Jeff," said Sherry, "you taste so good."

"That's a good start," said Jeff, "tomorrow I want to see you here at eight am sharp and you better be wearing the right clothes."

Jeff reached into his desk and took out the box of facial tissues. Sherry cleaned up her face as best she could and Jeff did the rest. She adjusted her clothes and kissed him. "Thank you Jeff," Sherry said, "I wont let you down."

When Sherry left, Jeff looked around his office, it was large enough for another small desk and he would order one tomorrow. He didn't think his life could get any more fucked up but he was wrong.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

The News

Jeff joined the throng of cars and headed home. He drove on autopilot and pulled his BMW into the driveway. The lights were on in the house and he could see his sister walking from the kitchen to the dining room, setting up the plates and dishes. Wendy noticed his headlights and waved at Jeff and blew him a kiss. He loved his sister and she proved to be one of the most skilled, animate lovers he had ever been with. Just watching her stirred him and he could picture her naked in his arms.

As Wendy looked out the window and waved to her brother she could sense something was wrong when he just sat in his car watching her. Leaving the plates on the dining room she opened the front door and walked to his car in her bare feet. The dress she was wearing was new and it was important to her that he liked it. As she arrived Jeff stepped out of his car, he towered over her five feet frame by over thirteen inches and she tilted her head up to look into his eyes. Her first thoughts were something bad happened at work.

"You okay bro?" Wendy asked with deep concern. "You don't look so good."

"Yeah I'm fine," said Jeff as he tried to put on a happy face. "So what's the good news dad wants to tell us? Did he say anything to you?"

"Not yet," said Wendy, "he said we have to wait until you are here, even mom doesn't know what is going on."

"Well let's go see what's up," said Jeff as he put an arm around his sister's shoulder and walked with her to the front door. "By the way Wendy you look stunning in that dress. Is it new?"

"Yes," said a pleased Wendy, "I bought it today just for you!"

Jeff couldn't help but smile at her infectious laughter as he watched her spin around on the sidewalk, admiring how the dress highlighted her tight body.

"Hey you two," said their mom from the open front door, "supper is being served." She loved how close her kids were and how they always supported each other. "Dad's waiting for us."

"Hi mom," said Jeff as he tickled Wendy while she ran into the house laughing. "Hmm, smells like a roast," Jeff announced as he entered, "this must be a real special night if you're making dad's favorite meal."

"He wouldn't tell me," she said, "all I know is he said to be prepared for a major event and that it deserved a roast dinner."

They all gathered around the dining room table surrounded by the steaming dishes prepared by his mom to celebrate the coming good news. The smell of roast beef and roasted potatoes filled the room and reminded Jeff of good memories from past family meals.

As Jeff sat down he looked at the walls lined with family pictures of happy events. The latest one being a plaque given to their parents by Jeff and Wendy on their parents 25th wedding anniversary. At the bottom was the inscription: To Bill and Sue Knight on this momentous day, may the next 25 years be just as blessed, Love your children Jeff and Wendy. He remembered their mom had cried a lot when they presented the plaque to them at the family gathering.

When everyone was seated they joined hands and their dad said grace. It was only in the last few years they had taken to this ritual at the insistence of their mom. Her beliefs had gotten stronger over the years and especially after the death of her own parents.

Soon the dishes were being shuffled around the table and when their plates were full their dad tapped his glass. "I know you are all wondering what the good news is I want to share with you," said their dad. "First I just want to say I have the best wife in the world and the best kids and I hope you will all support me."

They all looked at him with anticipation as he drew out the moment.

"Today I was offered the vice president's position at our main office, it would mean a move from Jacksonville to Atlanta." said their dad. "I told them it's a big decision and I needed to talk to my family before I could accept."

Jeff looked at his mom and her mouth was open in shock. "Move to Atlanta?" she said obviously surprised. "Atlanta? When do you have to let them know by? "

Wendy and Jeff looked at each other just as surprised as their mom. "Well, we don't have to rush," he said, "but they would like an answer by the end of the week."

There was an uncomfortable silence in the room as everyone digested the news.

"Dad let me be the first to say congratulations!" said Jeff. "I know how hard you worked for this promotion. You have always been the man I look up to and emulate."