Right or Left? Ch. 03

"Thanks, Jeff," said his dad, "that means a lot to me."

"Does this mean you will be selling our home?" said Wendy. "What about my school? I still have three more years at least!"

"It's okay Wendy," said Jeff calmly, "we can work it out."

"Bill, I'm sorry," said Sue, "Jeff's right you have made so many sacrifices over the years I am glad your company has recognized you. Congratulations! Atlanta is a beautiful city and I can't wait to move there with you! I love you!"

"Thanks," said Bill, "that means a lot to me. The company will put us up in a rental house until we want to sell this one. And of course, Jeff will have a new listing!" he laughed.

The rest of the meal was filled with talk of Atlanta and the amenities there. Jeff had never seen his dad so excited and his mom was getting into the mood as well. The only one who was having a problem was Wendy as she sulked throughout the dinner. After the dishes were cleared and his parents relaxed in front of the TV Jeff asked Wendy to come downstairs to talk with him. His dad gave him a thumbs up as he knew Jeff could get Wendy to understand the importance of his promotion.

Wendy entered Jeff's basement suite first and he followed her in locking the door so they wouldn't be accidentally disturbed. As soon as the door shut Wendy turned and threw her arms around her brother hugging him tightly.

"Oh Jeff, what are we going to do?" she said. "I don't want to move to Atlanta!"

"Relax Wendy," said Jeff, "first off no one said we have to move, it will just be mom and dad. Be happy for dad, okay!"

"But where will we live?" Wendy said. "I hate the campus dorms."

"You heard dad, his company is renting a house for them so we don't have to worry about moving," said Jeff. "Besides that means we will have the house all to ourselves!"

Suddenly Wendy's mood shifted from despair to utter joy and happiness. "You're right!" she exclaimed. "I never fucking thought about that! Oh my god I am going to fuck you every night until you scream for mercy!" she laughed.

"Shh, mom and dad will hear you," said Jeff.

Wendy was trying to smother Jeff in kisses but he was too tall to reach instead she knelt down in front of him. "If I can't reach your lips to kiss you maybe this will do instead," she said as she undid his pants and pulled them down. She loved that lately, Jeff had decided to go commando, so much easier to get to his cock.

Wendy's excited mood transferred over to her cock-sucking and Jeff was the beneficiary of the sudden change. She bathed his cock with her tongue, licking, sucking and deep throating him. She tasted his cum on his cock and knew he had recently had sex with someone.

The thought of his sister sucking his cock with their parents right above them was risky and stimulating at the same time. Jeff went with it and enjoyed her efforts. His cock was still a little sore from the blowjob that Sherry had given him but not so sore to stop his sister.

"Did you just have sex with someone?" Wendy asked as she licked his balls. "I can taste your cum on your cock."

Jeff thought about telling Wendy of Sherry but based on her inability to keep a secret he decided against it. "Yes," said Jeff, "and don't ask who with."

"You can't keep a secret from me, Jeff," Wendy laughed, "sooner or later you will tell me!"

Wendy's good mood was contagious and soon Jeff had a big smile on his face as he pumped his cock into his sister's mouth enjoying the moment. He took longer than normal to come but Wendy never once complained as she sucked him until he exploded in her mouth.

"Thanks, Wendy," said Jeff. "You really are a great cock-sucker!" He laughed as Wendy punched his shoulder. "Should we go upstairs so you can tell dad how proud you are of him?"

"Yes!" Wendy exclaimed, "I can't wait until they move out!"

Jeff and Wendy joined their parents upstairs and Wendy celebrated their dad's promotion like it was the best news she ever heard. Their dad looked over at Jeff and winked his thanks.

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

Day 1

Jeff arrived at his office early the next day as he waited to see if he had scared off Sherry.

To pass the time he looked at the album of nude images stored on his computer of his sister and her girlfriend Kylah. He had taken the photos at intimate moments when he had them pose for him and also when they were having sex together. Both girls were of similar height and build with Klyah's breasts slightly fuller. He compared the close-up shots of their pussy's and could almost smell and taste the difference. Wendy had her pussy shaved and waxed while Kylah's black curly hairs were just cut short. He didn't have a preference although his tongue did slide over Wendy's pussy much easier. Maybe he could talk to Kylah about having hers waxed before their joint spring getaway.

The sound of his phone startled Jeff out of his daydream. "Hello, Jeff here," he said.

"Hi Jeff, it's Kylah. Hope you are not too busy to talk? Sorry, I am calling so early but I am just heading to school."

"Hey Kylah, what's up? I was just thinking about you," he said with a big smile on his face. "Well, actually I was just looking at some of the photos I took of you and Wendy. You know the nude ones."

"Oh," said Kylah with a big pause, "I hope you are not showing them to anyone." Kylah knew her dad would have fit if he learned about the nude photos and she had no idea what he would do if he found out she was having sex with both Jeff and Wendy. The fact they were brother and sister would even make it worse.

"No, just me," Jeff laughed, "and my horny cock. So, how can I help you?"

"Well," she said hesitantly, "you said you would take me to a doctor for birth control pills. Our vacation is coming up soon and I want to be ready for you."

Jeff quickly checked his schedule and his afternoons were not too busy for the next couple of days. "Let me give the Doctor a call and see when he can fit us in," said Jeff. "Are you okay with short notice?"

"I guess so," Kylah said, "I am out of school early tomorrow if that works, anytime after two pm."

"Okay," said Jeff, " let me see what I can arrange. Say, what are you doing right now?"

"Um, just getting ready to drive to school," said Kylah. "Why?"

"Send me a picture," said Jeff, "a really sexy one that I can add to my collection."

At that moment Sherry walked into his office. "Okay thanks," said Jeff, "I have someone in my office now but look forward to receiving your message. Talk to you later."

Jeff closed the file on his computer and looked at Sherry. The transformation was amazing, the metamorphosis from a slut into a stunningly beautiful woman surprised and delighted him. She had the complete look from her chic dress to her flowing blonde hair and subtle make-up.

"Well done Sherry," said Jeff, "you look amazing! You are sexier in that outfit than anything you have ever worn to the office."

Sherry basked in the compliment and felt her cheeks redden. "Thanks, Jeff, I really want to make this workout."

"Come closer," said Jeff, "let me get a good look. Turn around."

Sherry turned her back to him and Jeff could see the outline of her bra straps and what appeared to be full panties. He would have to talk to her about that, there was nothing sexier than a woman in a thong. Jeff walked over to his door, closed it and locked it. Sherry watched Jeff with a puzzled expression.

"Even though we are the only ones in the office," said Jeff, "I don't want anyone to witness what I am about to do."

Sherry felt her heart race at the thought of what Jeff might have in mind, especially after what he did to her yesterday. As he approached the butterflies in her stomach took flight and she felt faint. Jeff stopped in front of Sherry and cupped her face in his hands then kissed her full on her lips, gently and sensually. "There are two sides to a coin," said Jeff, "yesterday was the rough one and today you get to experience the other side. Thank you for doing what I asked of you. Our relationship will be built on trust and loyalty and you have just taken your first step to show me you really will do whatever I ask of you."

At that moment Sherry was an emotional mess, no one, no one had ever reached inside her mind and body like Jeff. "Thank you, Jeff," said Sherry, "I promise I will always be here for you."

"Okay!" said an excited Jeff, "Let's plan our day!"

Jeff and Sherry spent the morning reviewing all his files, current listing, pending sales and all the completions coming up. He explained his file system to her and added her to his online client management program so she could enter data as well. He sent an email to Glen, the managing broker, to order a second desk for his office.

Halfway through the morning, Jeff received a text message and Sherry wondered why he had such a big smile on his face.

By the time noon rolled around they were caught up on all his current clients. The nosy agents in the office were having a field day wondering what was going on behind Jeff's closed door as they could hear laughter from him and a woman. When Jeff and Sherry walked out the silence from the agents was thick with confusion.

Jeff and Sherry ignored the other agents as they headed to his car. "Okay," said Jeff, "let's get a quick bite to eat and then introduce you to some of my sellers. I just have one stop to make on the way but it won't take long."

Sherry felt like she was in a whirlwind, she had learned more in one morning on client management with Jeff than she had in the two years prior. Jeff was very organized and efficient but still, she didn't know how he could take care of so many clients at one time. Sherry thought he must be exhausted at the end of each day.

Jeff pulled into the medical office of one of his favorite clients, Dr. Thomas Low. He was a general practitioner who specialized in family care. "I'll be right back," said Jeff to Sherry.

As Jeff walked into the office he saw the waiting room was full, Dr. Low was a very busy man. "Hi," Jeff said to the front desk receptionist, "I was wondering if I could speak with Dr. Low for a moment."

"I'm sorry sir," said the receptionist with a perfected smile, "as you can see he is very busy today. May I ask what it is in regards to?"

"I'm a personal friend, please let him know Jeff Knight is here and I only need a minute of his time."

The girl took in Jeff's professional appearance and decided maybe she should bother the Doctor if this was a personal friend of his. She was lucky to find this job last month and didn't want to make the Doctor mad and get fired.

"Of course sir," said the girl, "just give me one moment."

She came back quickly and ushered Jeff into the Doctor's personal office. "He will be right with you," she said.

Jeff looked around the office at all the diplomas and awards for community service, Dr. Low was well respected in the city by the general public and his peers.

"Jeff!" said Dr. Low, "how the heck is everything! Nothing wrong I hope?"

Jeff had assisted Dr. Low and his wife in the purchase of a home on the water and through their time together found they had a lot in common. They had participated in several marathons and were planning others in the future.

"I'm fine," said Jeff, " but I do have a favor to ask of you and it is a bit delicate, to say the least."

"How can I help?" said Dr. Low.

"Well," said Jeff, "I have a female acquaintance who is of legal age that needs to get a prescription for birth control but her parents can't know about it."

"That's it?", Dr. Low laughed, "Well I'm happy to hear you are taking in some extracurricular activities besides work."

"Yeah, I do work better hard," Jeff laughed along with the Doctor, "The other hiccup is we are leaving for vacation next week and she would like to be safe. Would you be able to see her tomorrow afternoon she is free after two pm?"

"Hmm, normally the wait time is about one month right now for appointments but I do owe you one for spurring me on to finish that last marathon," he said. "My office closes at four pm can she make it at that time?"

"Consider it done!" said a grateful Jeff, "I will personally make sure she is here at that time. I really appreciate this!" The men shook hands and Jeff walked out with a sense of relief.

Sherry watched as Jeff came out of the doctor's office with a spring in his step but she couldn't help but hope there was nothing medically wrong with him.

Jeff and Sherry spent the afternoon visiting his clients and introducing Sherry as his new business associate. He let everyone know of his upcoming vacation and promised Sherry would be there for any concerns they may have. Sherry basked in his confidence in her and once more thought how lucky she was to be by his side.

When they drove back to the office it was just close to seven pm, the parking lot was empty except for Sherry's car. "Let's go up to the office for a bit," said Jeff, "I want to go over a few things with you."

"Sounds good," said Sherry. She thought the day went well but now she was having second thoughts. Did she make a mistake along the way?

Once more Jeff closed and locked the door behind them as they entered his office. "First off I would like to say that you presented yourself in a very professional manner today," said Jeff, "I am very proud of you. But there is one thing you need to change."

"Oh," said Sherry, "what did I do?"

"I know I told you not to dress like a slut anymore," said Jeff. "But after watching you all day in those "granny" panties they just have to go," he laughed.

Sherry smiled at Jeff as she lifted up her dress revealing her full-size panties. "You don't like them?" she laughed.

Jeff reached for his phone, "I need a picture of this," he laughed. "Pose for me, show me your sexy granny panties."

Sherry lifted her dress up for Jeff and he took a series of pictures front and back as they both laughed.

"Now pull them down to your knees," said Jeff, "I want to see what your hiding."

Sherry did as Jeff asked, lifting the front edge of her dress up and exposing her pussy to him. She felt Jeff's fingers trace between her lips as he reached to her rosebud and back again. "From now on I want you to wear thongs," said Jeff, "and I like a smooth pussy so make sure you keep yourself shaved."

"Yes Jeff," said Sherry.

Jeff inserted a finger into her and slowly worked it back and forth. Sherry put her arms around Jeff's neck for support as she spread her legs wider to give Jeff more access. It didn't take long and Sherry's juices were flowing and her smell radiated upwards. "Are you always this wet," said Jeff.

"No," said Sherry, "you do this to me."

"I want to see the rest of your body, take your dress off," said Jeff, "and your bra."

Sherry slipped her dress off and undid her bra. She stood naked in front of Jeff as he admired her body. "Turn around," said Jeff as he continued to take pictures. "You are so fucking beautiful, bend over and open your ass cheeks for me."

The humiliation Jeff was putting her through stirred sexual feelings just as strong as rough sex and the fact he was taking pictures of her heightened the experience.

"Beautiful," said Jeff, "sit in the chair and spread your legs wide."

Sherry sat in the same office chair where this roller coaster ride started the day before. She placed each leg over the arms of the chair leaving her fully exposed to Jeff. She watched as he took close-up photos of her pussy and could see by the bulge in his pants that he was enjoying the show. She felt like a porn star and this was her debut.

"Do you like this Jeff?" Sherry asked, "Am I slutty enough for you?"

"Fantastic!" said Jeff, "finger your cunt while I take a video."

"Like this Jeff?" said Sherry as she pushed two fingers up inside, "Look how wet you made me, fuck that feels so good. Are you going to stick your big cock in my cunt? In my slutty cunt!"

Sherry pulled on her nipple with one hand as her fingers slid in and out of her pussy. "Fuck," moaned Sherry, "I need it bad."

"Don't stop," said Jeff as he leaned forward and pinched her other nipple and leaned down to kiss her. Their tongues swirled around each other in a hard kiss. Jeff reached down and pulled her fingers to his mouth, "Hmm, so good!" he said, "Let me know when you are close."

Sherry was ramming her fingers in now, her head was thrown back and Jeff was sucking on her nipple. He could hear the sounds of her wet pussy as she fucked herself. "Oh fuck Jeff," said Sherry as she pulled his head harder into her breast, "this is incredible!"

Jeff reached down and covered her hand in his as he slipped a finger in under hers. He slowed her rhythm down and pushed on her hand so her clit was being rubbed. "Look at me," said Jeff, "see it doesn't always have to be rough. Feel the pleasure in your body. Let yourself go."

Sherry's brown eyes were welling up as she looked at Jeff. He had reached into her soul so easily that it scared her to death. "Kiss me Jeff," said Sherry, "please, I need you so bad, I'm so close!"

The reaction was immediate as his lips met hers, she found his tongue and in her mind, she was sucking his cock. Jeff's hand had replaced hers and he was slowly fucking her with his fingers. When he pulled his fingers out completely she let out a moan of frustration then one of surprise as he pushed a finger against her puckered star. The lube from her pussy gave him easy entry and he pushed in her tight ass.

"Yes," said Sherry, "finger my ass, it feels so good."

Jeff's finger was going all the way in and out of her ass. Her position in the chair left her completely vulnerable to him. His palm was rubbing on her clit and he could tell she was close to coming as she thrust her hips up to meet his finger.

"Pinch your nipples," said Jeff, "I want to see your eyes when you come."

Sherry's body was covered in sweat as Jeff fingered her ass. She had never come this way before and just looking into his eyes gave her another surge of lust that drove her over the edge. "Oh fuck, oh fuck, right now!" she screamed as her orgasm hit. Jeff ground his palm against her clit, moving in a circle to draw out her pleasure. Her face said it all as she came, her mouth was wide open and she was gasping for breath.

As she came down from her high Jeff left his finger in her ass. "Did you like that Sherry?" he asked, "Your ass is so tight I can't wait to feel it on my cock."

"Whatever Jeff," said Sherry, "you can do whatever you want to me." She looked at Jeff in awe, how could such a young man know the right buttons to push. She could feel herself falling hard for him and it scared the fuck out of her.

"Do you want to fuck me?" said Sherry, "Anything Jeff, just tell me what you want and I will do it."

Jeff pulled his finger out of Sherry's ass and used her granny panties to clean his finger. "Right now," Jeff said, "I want you on my desk so I can taste your pussy." He helped Sherry stand on her wobbly legs and lifted her up so was sitting on the edge of the desk. He sat in her chair and moved it closer to the desk. "Put your legs over my shoulders," Jeff said.

Sherry's pussy was super sensitive and when Jeff's tongue touched her clit she almost fell off the desk. "Holy fuck!" said Sherry, "I don't know how much I can take."

Jeff pulled her forward a bit and Sherry had to lay down in order to stay on the desk. He had his head buried in her pussy as she wrapped her legs around him with her heels digging into his back. Her ex-husband never went down on her and it had been years since she anyone had. Jeff's magic tongue snaked its way through her folds concentrating on her clit. He teased her with light touches then hard suction as he tasted her juices. He could feel her ass clench and release as he supported her from underneath. Jeff wanted her to experience sex without pain and show her there was an alternative.