Right or Left? Ch. 04

Thanks once again for your support and votes on my evolving incest saga.

The story continues with Jeff and Wendy (brother and sister) and her girlfriend Kylah preparing for their upcoming spring break vacation.

In this chapter:

Kylah panics

Jeff's sister Wendy provides much-needed relief

Sherry, Jeff's new business associate shares a dark secret with him

Kylah's mom, Jasmine, relives her youth

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're allergic to incest, anal, oral, threesomes, humiliation or sex, in general, please do not go any further.

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Kylah panics

Kylah pulled into Jeff's real estate office lot and was glad to see his car was still there. She didn't know what she would have done if it wasn't. She parked next to his BMW and waited for him to come out. Her heart was beating a million times a minute and her hands were still shaking. After waiting for a bit and when Jeff didn't come out she decided to go inside to see him. The door to the building was locked and Kylah leaned against the building for physical and emotional support. Kylah jumped when a pretty blonde woman opened the door.

"Hi," Kylah said timidly, "is Jeff still inside?"

Sherry gave the young girl the once over and thought she didn't look like a client. She was very short maybe only five feet tall and looked like she was about sixteen. Her baggy jeans and shirt hid any knowledge of her body. The only thing that the clothes couldn't hide was her bubble butt. Sherry could see the girl had been crying and even without any makeup on her skin had a beautiful light coffee color.

"Are you his sister?" asked Sherry.

"No I go to college with his sister, I'm a friend," said Kylah.

"Well, Jeff is still inside he said he had some paperwork to look after so he may be awhile," said Sherry hesitantly, "Would you like me to unlock the door for you?"

Kylah thought about this for a minute. Normally she would never bother Jeff at work but this was an emergency. "Yes please if you don't mind. Thanks."

Sherry looked the girl over once more and up close she really was very pretty, too bad no one has told her about makeup she could be stunning with her bone structure. "My name is Sherry by the way I just started working with Jeff."

"Congratulations," she said, "I'm Kylah." Kylah saw that Sherry didn't seem to have a bra or panties on as her dress clung to her body and her nipples were clearly visible. She was several inches taller than Kylah and her blonde hair was a little messed up.

Jeff was working on the last of his paperwork when Sherry and Kylah walked in. He leaned back in his chair at the unexpected surprise.

"Hi, Jeff, sorry to bug you," said Kylah, "can we talk?"

"Of course," said Jeff surprised to see her. "Why didn't you call me I would have come right down?"

"Well," said Kylah, "I met Sherry coming out of the building and she said you were doing paperwork. She offered to let me in, I hope you don't mind."

"Just give me a minute and I will be right with you," Jeff said as he walked out of the room with Sherry. They walked down the hall and away from his office. "Thanks, Sherry that was nice of you," said Jeff, "Kylah is my sister's friend."

"That's what she told me," Sherry said, "looks like she is a little upset and I didn't want to leave her outside all alone."

"That was nice of you, thanks again," he said. "See you tomorrow."

Jeff watched as Sherry walked down the hall he knew she was nude under her dress and he liked the way her ass wiggled. Jeff knew she was going to be a great real estate assistant and when she promised to do 'whatever' he asked of her, he had let his cock do the thinking for him. He was a sucker for a damsel in distress and hoped this one didn't come back to bite him in the ass. His biggest concern dealt with Sherry's preference for rough sex but this evening he showed her that sex can be loving and satisfying without pain. Jeff had given her a major orgasm as he satisfied her orally and as much as he wanted to fuck her he decided to make tonight all about her.

When Jeff walked back into his office he realized you could still smell the aroma of Sherry's pussy juices in his office. Kylah looked at him when he came in but either didn't notice the smell or didn't want to confront him. She was still standing in the same place as when he left the office and he guided her by the elbow to one of the client chairs then pulled the other one in front of her for himself. Jeff could see Kylah was stressed about something but even in her anxious state she was still a very sexy teenager.

Jeff placed a hand on her knee, "So, what's up?"

"I have a problem," said Kylah with concern, "with my mom."

"I thought they were down south helping out with the relief effort?" said Jeff.

"They came back early and surprised me," Kylah paused, "My mom found the picture on my phone that Wendy sent me of your cock."

Kylah struggled to keep her composure. "I couldn't lie to my mom," she said, "I told her it was yours."

"Fuck, fuck!" Jeff exclaimed. "Did she tell your dad?"

Kylah looked down at her hands clasped together in her lap. "No, she said she wouldn't tell my dad if you talk to her tomorrow morning." Kylah said, "She said to come over at ten after I go to school and my dad will be gone too. She wants to meet with you alone at our house. "

Jeff was thinking of the consequences, Kylah's mom probably wanted to cancel the upcoming spring break vacation, at least he hoped that was the only thing she would do. If she told her overprotective husband about the picture the results would be much different for him and Kylah.

"Do you have your phone with you?" asked Jeff thinking he could remove the photo.

"No, my mom kept it."

"Fuck," he said, "did she see the photos you sent me as well?"

"Yes," said Kylah, "she asked me if we had sex. I couldn't lie to her, I told her yes."

"What about Wendy and I, does she know that too?" Jeff asked with dread.

"No Jeff!" Kylah exclaimed, "I made a promise to you and Wendy and I would never go back on that."

Jeff gave a sigh of relief as Kylah never disclosed Jeff and his sister were in an incestuous relationship. "So I guess that means you won't be coming on the trip with us," said Jeff.

"Actually mom said once she talks to you about something that she will let me go." said Kylah, "She also wants me to be on birth control and I told her you were looking after that. Did you get me an appointment with your doctor?"

Jeff was totally confused now as he mulled it over in his mind. Her mom wanted to meet with him first then Kylah could still go on the trip with them, something didn't seem right.

"Okay," said Jeff, "I'll meet your mom in the morning and see what's up." Jeff tore out a page from his notebook and wrote down the doctor's address. "I have the doctor's appointment set up for four pm tomorrow. I will meet you there. Okay?"

"Thanks, Jeff," said Kylah, "my mom said when she met you the first time she really liked you but she wants to see you again before she will still let me go on our vacation."

Jeff could see Kylah had relaxed a bit now that he was okay meeting her mom. "What's your mom's name again?" said Jeff.

"It's Jasmine," said Kylah. "Thanks, Jeff, I really appreciate it."

Kylah leaned over to kiss Jeff goodbye and when the kiss ended she looked at him strangely. Jeff guessed Kylah could taste Sherry on his lips. After pleasing Sherry orally and not getting any relief Jeff's cock was straining for release. Jeff kissed Kylah deeply once more as his hands reached under her loose top to massage her firm pert breasts through her bra.

"What do you taste on my lips?" said Jeff to Kylah as he looked into her eyes, he wanted to see if Kylah would say anything.

"I taste another woman," said Kylah shyly.

Jeff looked at Kylah, her brown eyes held steady with his. He felt the need to let Kylah know what she was getting into. "Kylah, I'm not a good man," said Jeff, "I like sex, a lot. That's Sherry's pussy on my lips, I haven't fucked her yet but I may."

Jeff didn't know why he was confessing to Kylah there was just something different about her and he was starting to really care for her.

Kylah looked back at Jeff and nodded. "I understand Jeff," she said, "If that's what you need then I don't care as long as I get you sometimes too."

The young teenager was madly in love with Jeff, so in love, she was willing to look the other way for his indiscretions. Right now she was in Jeff's arms and that's all that mattered to Kylah.

"Oh no!" said Kylah suddenly, "I have to get home right away, my dad is waiting for me. I don't want to leave Jeff but maybe I should."

"Damn," said Jeff, "my cock is ready to bust! No, you're right, we don't want to mess up our vacation plans this close to leaving."

They stood and hugged one last time. "Do you want me to suck you Jeff?" said Kylah, "I will."

"No," he said reluctantly, "you better head home."

Jeff walked Kylah out of the building and watched as she drove away. He sat in his car while he gathered his thoughts. He reviewed the situation in his analytical mind and then it donned on him, Kylah's mom knew they were having sex yet she still agreed to let her daughter go on the trip, that meant she wanted something from him and he was pretty sure he knew what it was.

Jeff thought back to the first time he met Jasmine to get permission for Kylah to go on the vacation with Wendy and him. He was surprised to discover Kylah's mom was African American and her pastor dad was white. He could still remember how Jasmine held his hand in both of hers and brought it to her chest when she said goodbye to him. The mental picture of his hand between her large black breasts was ingrained in his mind. Maybe tomorrow's meeting wouldn't be as bad as he thought.

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Wendy the best sister ever

By the time Jeff got home it was late and his parents were already in bed. He found Wendy at the kitchen counter making a cup of sleepy-time tea. She had her bedtime sweats on, a college tee shirt and no bra.

"Hey bro," said Wendy, "another day another dollar? Want a cup of tea?"

"Sure Wendy, thanks," said Jeff, "Did you talk to Kylah today?" he asked.

"No, why?"

"Maybe we should go downstairs then," said Jeff, "I have some news to share with you."

The brother and sister went down the stairs to Jeff's self-contained suite and Jeff locked the door once they were inside just in case his parents came down.

Jeff filled Wendy in on the conversation he had tonight with Kylah. At first, Wendy was pissed but when she found out Kylah could still join them she was elated.

"That's great news! Good luck with Kylah's mom in the morning," said Wendy as she let out a big yawn and kissed Jeff good night on the mouth. "Hey!" she said, "Is that Kylah I smell on your face? Naughty boy!" she laughed as she headed towards the door leading upstairs to her bedroom.

Jeff laughed along with Wendy but he wasn't about to tell her the smell was from Sherry his new assistant. He had wanted to fuck Sherry so bad but decided tonight he would just give pleasure and not receive it. And then when Kylah met him in his office he was so horny he wished he could have accepted her offer of a quick blowjob. Right now his cock was aching for release.

He looked at his sister and the urge to fuck her took over. "One more kiss?" he said as he picked up her small five-foot body in his arms. Wendy and Kylah were almost the same height and had very similar bodies. Wendy wrapped her legs around her brother and he could feel her pussy rub against his body. They kissed deeply as Jeff held her in the air. "I need you, Wendy," Jeff whispered, "you would not believe how fucking horny I am."

"Sorry," said Wendy, "it's that time of the month." As she looked at his sad eyes he got the best of her. "Okay, okay," she laughed, "do you want my ass or my mouth?" She loved her brother and if he needed a quickie she wanted to please him.

"Yes!" said Jeff, "you're the best sister in the world!" Jeff carried Wendy into his bedroom with her legs wrapped around him. "Can you be quiet Wendy?" Jeff asked as he set her on his bed, "I don't want mom and dad to hear us." Wendy had a tendency to be very vocal when they were having sex, very vocal.

Jeff pulled down Wendy's sweats and panties and flipped her onto her tummy. "I want your ass," he said, "your firm little ass."

Jeff placed a pillow under his sister's belly and gave her the other one to rest her head on and hopefully muffle any screams. He opened his nightstand and found the lube, as he squeezed some onto Wendy's ass she jumped at the coldness. He massaged it into her puckered star and watched as her ass relaxed giving his finger full access. "Oh fuck Jeff," said Wendy, "you do that so nice!"

Wendy continued to moan as her brother fingered her ass, she felt him add another finger and pushed back against his hand. She loved anal sex, the feeling was so different so erotic. When Jeff pulled his fingers out she knew his cock would be the next thing to enter her ass. She heard him undress but didn't turn around to watch she wanted to feel him not see him, she closed her eyes and hugged the pillow under her head. The anticipation built as she waited for his touch again.

Jeff was hard, so hard from his time pleasing Sherry with no release for himself and then turning down Kylah's offer of a quick blowjob. Wendy's ass swayed as she waited for her brother to fuck her. Jeff knew he was lucky his sister liked anal sex as it was one of his favorites too. He held his hard cock in his hand as he rubbed it between her ass cheeks, coating it in lube. Wendy moaned into the pillow as the mushroom head of his cock entered her ass.

"Fuck," said Jeff, "I love your tight ass."

"Do it, Jeff," said Wendy, "stick your big cock up my ass."

He pushed his cock in slowly as he felt the unique sensation that only comes with anal sex. His hands were on his sister's hips as he watched his cock slide in and out, holding her in place so he could fuck her at his pace. "Do you like this Wendy?" Jeff asked. "Do you like my cock in your ass?"

"Oh fuck Jeff it feels so good," said Wendy, "I could do this all night with you."

"Hmm, that would be nice," said Jeff, "fucking your tight little hole all night."

Jeff increased the pace thrusting harder now, he didn't want to come too quickly but her ass was so tight. "God that feels so good!" Jeff moaned, "I love watching my cock go in and out of you."

"Harder Jeff, fuck me harder!" Wendy begged.

Jeff pulled his sister's hips back with each hard thrust as he drove into her. He was filled with a deep passion, wanting release but not wanting it to end at the same time.

Wendy had her face buried into the pillow as her brother slammed into her again and again, she fought to keep her screams down and had to bite hard on the pillow. Her hand was between her legs playing with her pussy and clit as her brother fucked her ass.

"Oh fuck Wendy," Jeff moaned, "I'm so close."

"Not yet Jeff," said Wendy, "hold out a little longer." She was so close to her own orgasm and wanted to come with him.

Jeff used all the willpower he had to hold out as he slowed down his pace. The sensual feeling was incredible and it didn't help that sister's ass had clamped down onto his cock. It was overpowering and he knew it was useless to resist.

"Ah fuck here it comes!" Jeff shot his load deep, all his pent-up sexual energy released into his sister's ass as his cock pulsated again and again. Wendy sighed with relief as her orgasm hit just before his.

Spent Jeff fell forward onto her body-hugging her into him. "Thank you, Wendy," Jeff whispered as he kissed her back and neck, "you don't know how badly I needed that."

They laid on the bed together until Jeff's cock went soft and slowly slide out. Jeff wasn't ready to let his sister go and spooned her while absently playing with her nipples.

"I wish I could spend the night with you," Wendy said.

"Me too," said Jeff, "I can't wait until next week and our trip."

Eventually, Wendy got up and dressed, she looked at her brother as he slept on the bed. He had fallen asleep, she kissed him goodnight as she covered him with a blanket then made her way upstairs quietly to her own bedroom.

That night Jeff had the strangest dream of being naked and surrounded by women who all wanted him.

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Sherry's dark secret

Jeff was in his real estate office refreshed and eager to start the day. His morning run allowed him time to think about his upcoming meeting with Kylah's mom and he came up with several options.

Sherry arrived bright and early as well and when Jeff complimented her on her nice outfit she beamed in response. Together they reviewed all the upcoming business and arranged for Sherry to show properties to one of his clients in the afternoon, some cash buyers, and Sherry was super excited to prove herself to him. Jeff told Sherry he had a personal appointment to attend to this morning and would be unavailable for a few hours.

"Jeff," said Sherry, "before you leave can I talk to you about a personal issue?"

"Of course," said Jeff, "but are you sure I'm the right guy to talk to?"

"Well," she said, "you are the only guy I can talk to."

Sherry looked at Jeff and wondered if this was the right time or not. She didn't want to jeopardize her new position with him but after what he had done to her sexually in the last few days it weighed heavy on her mind.

"It's about sex," said Sherry, "actually it is more about sex with you. I need to share a dark secret with you."

Jeff could see the change in her demeanor as she fought to keep her emotions under control. He got up and closed the door to his office and locked it so they wouldn't be bothered.

"Take your time," said Jeff, "and just know I won't judge you."

"Well," Sherry said, "you already know I like rough sex and that is the only way I can get off or have an orgasm. But last night...you made me come harder than I ever have and you did it without hitting me or any pain. And that was just with your mouth, I can't imagine what you can do with your cock," she laughed.

Sherry hesitated and Jeff held his voice to let her continue when she was ready.

"I need to tell you why I like rough sex," said Sherry, "it started when I was in college. I had a boyfriend who treated me badly and abused me. Every time we had sex he would hurt me and tell me I was his whore to use any way he wanted. I'm not proud of this time in my life but it happened."

Sherry stopped and Jeff could see this was bringing back some very dark memories. He wanted to reach out and take her hand but wisely let her be.

"I know I should have left him," said Sherry, "but I was young and impressionable. He convinced me I was worthless and the only way he allowed me to orgasm was with pain. I was with him for 2 years and at the end, he had brainwashed me. I know that now but I couldn't break the cycle."

He saw the torment in Sherry's eyes and wanted to find this son of a bitch and beat the shit out of him. But mostly Jeff was severely disappointed in himself, he knew he could be an asshole sometimes but he was devastated that he had inadvertently perpetuated the cycle of abuse against Sherry.

Sherry watched Jeff lower his head unable to look at her and foolishly worried she had disappointed him.

"When I met my husband he was the exact opposite of my boyfriend and I thought he was what I needed to cure me," said Sherry. "But it didn't work, he never gave me an orgasm for our entire marriage. I thought it was my fault and after we divorced I went back to my old ways."