Right or Left? Ch. 02

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Brother and sister continue affair and bring in a friend.
15k words
4.7
80.3k
109

Part 2 of the 8 part series

Updated 06/08/2023
Created 08/21/2017
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This is a continuation of a previous chapter, thank you for your interest, comments, messages and of course your ideas. Thanks and happy reading. Knightfantasies

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This past weekend Wendy and her brother Jeff became new lovers, it was nothing either of them planned to do it just happened.

As the weekend was winding down neither of them wanted the new affair to end, they made love one last time and talked about how they could keep this going. Jeff expressed caution but Wendy, being the more reckless one, was excited to remain lovers.

Monday arrived and Wendy was in her favourite coffee shop having her usual latte before the long drive to college.

A smile spread across Wendy's face as she sat at the tall round table. She recalled how great the sex was with her brother and couldn't count how many orgasms he had given her. Subconsciously she licked her lips as she remembered how good his cock tasted. Nothing her brother did turned her off, he had fucked her mouth and pussy and even her ass. She did everything he asked of her and in turn she had never been so sexually charged and satisfied.

Wendy looked around at all the people beginning their day and almost screamed it out loud to everyone in the coffee shop, 'Jeff and I are lovers! We are fucking lovers!' Luckily for her and Jeff she kept her mouth closed and shouted only in her mind.

Jeff knew Wendy could be a little impetuous and a bad break up with her last boyfriend had made her cautious towards looking for a new relationship. He could see she was now focused entirely on him and knew this could be a potential roadblock.

Being a caring sibling he wanted his sister to explore 'other options' so he downloaded a dating app on her phone to help her find a "new" guy. Wendy reluctantly agreed to give it a try even though she told him the only guy she wanted right now was him.

Wendy was sipping her latte as she was using the dating app. She was going through all the guys posted on the dating app and let out a big sigh as none of the guys interested her. She promised Jeff she would at least give it a try and that is what she was doing.

She froze when the next photo came up. He was perfect, handsome in a very manly way, and exactly what she was looking for. She quickly swiped to the right and waited for his response.

Minutes ticked away as Wendy anxiously waited. Her heart was thumping in her chest with anticipation.

"YES!" Wendy shouted almost spilling her Chai latte.

She gave a fist pump and then looked around as everyone stared at her. At that moment she didn't care what anyone else thought of her, she was excited and feeling on top of the world.

The only picture she had swiped right on was her brother and he accepted her request! She laughed that his suggestion to find a guy had come back full circle to him.

Wendy finished her latte and jumped down off the high stool, being only five feet tall was a challenge but also a blessing. Her tight yoga pants showed off her cute little bubble butt and being smaller meant that her breasts looked that much bigger.

She headed to the washroom for a quick pit stop before the long drive to her college class. As she sat on the toilet she couldn't stop thinking about her brother's hard body. After a quick tinkle and wipe she decided to rub one out. It didn't take long to make her pussy wet and juicy as her fingers found their mark. To thank Jeff for the weekend she took a close up photo of her soaked pussy and texted it to him with an emoji of a big set of red lips. She laughed as she imagined the shocked look on his face when he got it and hoped it would make his day a little more special.

On the long drive to college Wendy was still enjoying the after effects of her quick bathroom orgasm and she was thinking all kinds of sexy thoughts as she imagined places she and Jeff could meet. Private places where no knew who they were or that they were brother and sister. Spring break was coming up and she had talked to her girlfriends about a getaway with them. She decided to talk to Jeff tonight about it and see if he could get time off from his job. Just the thought of spending some quiet time with Jeff made her pussy wet again.

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Jeff was showing a home to some clients and looked at his phone when his sister's text arrived, he decided to open it when he was alone. A half hour later Jeff was glad of that decision. The look of surprize on Jeff's face said it all, he recognized the picture was of his sister's pussy and it brought back memories of their past weekend together. He could feel his cock harden as he looked at her picture and thought back to how many times he had fucked her tight young pussy. The sex had been intense and Wendy was incredible. There was nothing she wouldn't do or try and she even surprized him with a few ideas of her own.

Jeff was only a few years older than Wendy and rather than go to college he decided to choose a different career path and became a real estate agent. He knew his age would be a challenge but his enthusiasm more than made up for it and after three years in the biz he was consistently in the top ten in the city for sales. His parents were very proud of him and his dedication and supported him wholeheartedly.

Life was good for Jeff and other than a new car he was very smart with his money. He still lived at home in his parent's basement suite, it wasn't fancy but it served a purpose. He could enter through a separate basement door but most times he just came in the back door. He loved that he had his privacy but also the advantage of still being part of the family.

With all his hard work and success he would have a very healthy down payment by the end of the year. His dream of buying a home of his own would soon become a reality because of his frugal lifestyle. All he wanted was a modest home, maybe one with a basement suite so the income could offset any slow periods in real estate. He knew his buddies could only dream about owning their own home at this time.

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Throughout the day both Wendy and Jeff relived memories of the past weekend in their minds. Wendy had no regrets other than the weekend ended too quickly but Jeff felt some remorse in being a little too aggressive with his sister. He liked to be in control and right from the start he had ordered his sister to follow his instructions. She had hesitated at first but soon fell into a semi-submissive role. He found it interesting that half way through the weekend Wendy also became a little aggressive and they alternated back and forth.

At supper that night their parents talked about their trip to her mom's sister place and quizzed Wendy and Jeff on their weekend. With a straight face Jeff said they spent some time together watching movies and just laying around. His mom expressed surprize as usually on weekends Jeff was tied up with clients showing and selling homes. Jeff said he was feeling guilty about being such a workaholic and Wendy was the perfect stress relief. He said it was one of the best weekends of his life and he felt energized again. Jeff's dad said it was about time he took a break and enjoyed himself; both Wendy and Jeff smiled and agreed with him.

Wendy looked down with a frown on her face and her mom asked her if there was a problem. Jeff felt his heart pound as he thought she was going to disclose what they had really been up to all weekend.

Wendy raised her head and thought this was the perfect time as she looked at her parents. "Do you think it would be alright to go on a road trip for spring break with my girlfriends?"

Both of her parents raised their eyebrows and expressed concerns. "Wendy you know how we feel about what could happen to young women at those kinds of gatherings," said her dad.

She knew they loved her and were just being protective. "Maybe Jeff could drive us and be our chaperone," said Wendy.

Jeff looked and felt like he had just been sideswiped. "Um who would be going with you?" he stammered. "With us?"

"You already know them, Ginny and Kylah," said Wendy.

"I don't know Wendy," said Jeff. "How long would it be for?".

"Well," said an excited Wendy. "We were thinking about ten days but even a week would be fantastic!"

Jeff looked at his mom and dad, "what do you think?"

"I know you haven't had a holiday in almost three years," said his mom. "But with three girls to look after I am not sure that qualifies as a holiday."

"Dad?"

"If you agree to keep a close eye on the girls then I am okay with it," said his dad.

After some hesitation Jeff agreed to be a chaperone. He looked from Wendy to his parents. "Okay" he said, "I am in but only for a week, and, only if I can get one of the office agents to cover for me."

Wendy was ecstatic and punched Jeff in the shoulder. "Thanks big brother we will have a great time!"

Jeff smiled back and wondered what he had gotten himself into.

When everyone had gone to bed Wendy sent Jeff a text message from her upstairs bedroom. She thanked him for agreeing to be a chaperone then asked him to sneak up to her room so she could thank him personally.

With Jeff in the basement and their parents master bedroom being on the main floor the risk of either of them getting caught sneaking upstairs or downstairs was too big.

After Jeff texted her it would be too risky going to her room Wendy wanted to continue texting. Soon messages were flying back and forth with promises of what they would do to each other when the opportunity arose. Wendy wanted a picture of Jeff's cock and he reluctantly agreed. He sent one to her with his cock at full mast and told her he was hard after watching the video from this past weekend of her masturbating. Not to be outdone Wendy pulled her purple dildo out of the nightstand and sent him several pictures of it in her pussy. Eventually both of them called it a night and turned off their phones.

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The next morning Jeff missed his regular routine of getting up early and going for a run, he was dragging a bit as his sister had kept him up until almost 1 am. Even though he was tired he decided to take the long route for his run, the fresh air was just what he needed to clear out the cobwebs. When he returned home he was surprized to see Wendy in the kitchen having some cereal, usually she was on her way to school by now as her drive took over an hour.

She offered him a glass of orange juice. "Freshly squeezed big guy, just the way you like it," she laughed. Wendy gave him the once over as she eyed him from top to bottom. "Hmm, I don't think I have seen you this sweaty since the weekend!"

Jeff looked around guiltily. "Shush Wendy, mom and dad will hear you," Jeff whispered urgently.

Wendy debated teasing her brother some more but decided to come clean. "Actually mom and dad just left, something about one of the vehicles having to go in for service," she said. "Looks like we have the house to ourselves. Hmm, anything you want to do?" Wendy asked teasingly.

In two steps she was in front of her brother and reached for his running shorts. Just like that Wendy had Jeff's shorts down to his ankles and knelt on the tiled floor staring at his cock as it hung down. "What no underwear?" she teased. "And why aren't glad to see me? Maybe you just need some on my special attention!"

Jeff wasn't sure if his parents were really gone or not but knew Wendy would never purposely lie to him and expose him like this. He allowed himself to relax and soon Wendy's expert sucking had him fully hard. With two hands in her blonde hair he gently took control, guiding her mouth deeper and deeper on his cock. Holding her for a count of three then slowly releasing her off when she started to gag.

"You're getting much better at this," said Jeff with pride. "Pretty soon you won't gag at all."

Wendy was pissed at herself, she wanted to show Jeff she could take all of him in her throat and not gag. She had practiced over and over again last night on her dildo but her brother was just a little thicker and longer.

"Really?" said Wendy accepting his challenge. "Well watch this!"

"Hey I wasn't disappointed," he laughed. "I was giving you a complement. You are amazing!"

Wendy lifted his cock up and licked the sensitive underside from his balls to the tip. "Do you want to come in my mouth?" Wendy asked shyly.

"Only if you will come in mine after," said Jeff.

Jeff could see the mischief in his sister's eyes and he pulled her back into his crotch. She licked his balls, not minding his sweaty body, she was actually getting turned on by the pheromones he was giving off. She loved her brother so much and would do anything he asked of her, anything.

Jeff was still being cautious, "let's go downstairs to my room," he said.

"Ah, do we have to?" Wendy pouted. "It's kind of sexy here in the kitchen."

Jeff pulled his shorts up and together hand in hand they made their way down to his basement suite. The door at the bottom did have a privacy lock and just to be safe Jeff made sure he locked it. The last thing he wanted was for either of his parents to discover what they were doing.

"Do you want me to shower?" he asked when they entered his bedroom.

"No, I like you all sweaty and slippery," she said.

Wendy started to get undressed and Jeff watched his sister. Even though she was small she was certainly put together in one sexy package. He loved her tight little body with curves in all the right places. Her breasts were perfect with no sag and very small areolas. Her tight ass jutted out from her body; all those years of gymnastics had given her a real hard body.

In one easy motion Jeff lifted his naked sister up in the air and held her there. "Now what should I do with a beautiful naked young woman in my bedroom?" he laughed. "Any ideas?"

"Jeff, stop it you're tickling under my arms!" Wendy laughed as Jeff threw her onto his bed.

Before she could say another word he had his hands under his sister's knees. He drew her body to him, spreading her legs, "hmm, now that is a nice looking pussy!" Jeff said.

The first touch of his tongue on her folds revealed a hard clit, she smelled clean and fresh even though she was already wet. He loved the smell of her pussy, drawing in a deep breath and then blowing across her nether lips. It was so easy to get lost in pleasing her as he explored all of her layers and finally drove his tongue deep inside her.

Wendy had her legs clamped around her brother's head, "oh, you nasty boy you like licking my cunt don't you?" Her body was arched into the sky with only her shoulders and head on the bed. "Oh god, that feels so good! Fuck me Jeff, fuck my juicy wet cunt with your tongue!"

Jeff had both hands squeezing her ass cheeks holding her in the air, her small frame almost making her weightless. Wendy participated by humping his face as he sucked and licked her pussy.

"Oh fuck, you're good! Too good! My cunt is on fire! Don't you dare stop I'm almost there!"

Jeff felt like a teenager again as he feasted on his sister's pussy. The taste of her pussy so sweet, he couldn't get enough.

When the moment came and Wendy exploded her brother didn't stop but continued to suck on her and use his tongue on her pussy.

"What are you doing Jeff? Fuck! Oh, fuck!" Wendy screamed. "Are you going to keep sucking my cunt? Yes, just like that! Give it to me!"

Jeff had a hard time holding onto his sister as her body squirmed in his hands. Her screams filled the room and if his parents had been home there is no doubt they would be running down the stairs. When she had a second orgasm it was more powerful than the first. Her body collapsed and she lost all muscle control as Jeff gently lowered her legs.

"Holy fuck Jeff that was fucking amazing!" Wendy gushed. "You really know your way around a pussy!"

"My pleasure and I mean it!" he said.

"My turn, come lie down big boy and let me suck your cock!"

"Let's try something new, do you trust me Wendy?"

"Anything Jeff, anything you want!"

Jeff positioned his sister so was on her back and her head was on the side of his bed, bent back slightly. Wendy knew he was going to fuck her mouth this way, she had seen plenty of porn movies of women doing this and not all of them were pretty.

He rested his balls on her lips, waiting to see what she would do. When he felt her tongue snake out he let her lick and suck on his balls for a bit before stepping back.

Jeff looked at his sister with lust in his eyes. "Are you ready sis? I'm going to fuck your mouth until my cock is in your throat," said Jeff. "If it's too much just tap on my leg,"

Wendy was a little scared but she was also determined to show her brother she could do this. "Okay, but go slow please."

True to his word Jeff started off really slow, only putting the head of his cock into her mouth, letting his sister get used to the position. She licked and sucked on what was offered to her. When he felt she could take more he gradually leaned into her. He placed both hands on her breasts pinching her nipples then looked down towards his sister. He could see his cock going in and out of her mouth, and he felt incredible.

As more of his cock entered her mouth he could feel her tense up. He stopped and allowed her to once more adjust, controlling the depth based on her reactions. "Are you okay?" Jeff asked. "You're doing great!"

"Don't worry Jeff I know you are trying to be gentle but I want to feel your passion, I will let you know if it is too much for me."

"It feels fantastic Wendy!"

Wendy gave Jeff an upside down smile. "Do it Jeff, fuck my mouth," she said as she opened her mouth to give his cock entry.

Jeff lined up his cock and eased it into her mouth pushing until he was half way in. He could feel the resistance in her as his length reached her throat. His hips rocked back and forth and he watched as her throat bulge. The sight and sensation as his cock entered his sister's throat was unbelievable. With only a small portion left out of her mouth he pinched both of her nipples and pushed in. The pain caused his sister to open her throat completely and he bottomed out.

"Fuck! You did it!" Jeff yelled. "I'm all the way in!"

Wendy couldn't believe what Jeff was doing to her mouth and throat. It felt like his cock was driving right into her lungs. Several times she almost tapped on his leg to stop him and when he pinched her nipples the pain opened the last of her throat and she felt his balls on her nose and his cock all the way in. Never in a million years did she think she could swallow a cock this way and she was proud of herself.

Jeff's thrusts were slow now, fully out and fully in, Wendy realized he was making sure she could breathe before pushing back in. Complete trust had been granted by her to her brother and she relaxed a little more.

"Oh god you're fantastic!" he said. "I can see my cock in your throat!"

Wendy needed a distraction, her fingers found their way inside her pussy and she stroked them in and out. She could feel her brother's cock going in and out of her throat and suddenly she had an out of body sensation of watching from above like they were in a porn movie and the thought turned her on even more.

Jeff was in heaven as his cock rocked in and out of his sister's mouth and throat. He marveled at the incredible sight every time her throat bulged out. The tightness that gripped his cock was unlike any sensation he had ever felt before. He watched his cock enter Wendy's throat and slide deeper and deeper.

Jeff was close to coming and he could feel his cock grow even larger when he suddenly felt fast tapping on his leg. Without realizing it he had stopped mesmerized by the sight. Wendy had patiently waited for Jeff to pull out but when she finally ran out of air she panicked and tapped out.