Family Business Ch. 04

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He sees another side of his big sister.
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Part 4 of the 6 part series

Updated 10/29/2022
Created 12/09/2004
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jt123
jt123
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The next few weeks passed without anything out of the ordinary happening except for one magnificent night when Mike was able to "finish" his ski weekend with his mom. It was a Saturday at the end of January when they were able to get together.

Leslie had called him a few days earlier asking if he had any plans for Saturday. Mike replied no before he even thought about the coming weekend. Honestly, he didn't care what he might have planned for Saturday. He knew nothing he had already planned would even compare to being with his mom.

Fortunately, it turned out that Mike didn't have anything planned, so he concentrated fully on looking forward to his date with his mom. When Saturday arrived Mike got ready and left to pick her up. He shook his head and laughed as he made the drive thinking of how impossible it seemed that he was driving over to pick up his own mom for a date that was certainly going to end with amazing sex.

He didn't even have to get out of the car when he pulled up to the house where he grew up. He had just turned off the ignition switch and was about to get out, but he saw the door open and her step out. He did get out and open the door for her before starting the car back up and driving to the restaurant where they had reservations.

Dinner was fabulous and they had time to enjoy a couple rounds of drinks before they got back in the car and drove to the theater. They had talked on the phone about a new movie opening that they both wanted to see, so they decided to do a simple dinner and movie date night.

They sat close in the theater and Mike wrapped his arm around her shoulder. As the lights dimmed and the movie started Leslie's hand moved to his knee. Slowly, as the movie progressed, her hand crept higher on his thigh until, just as the movie was reaching its climax, her fingers slipped over his crotch and began caressing him through his pants.

It was hard for Mike to suppress his moan of desire as her fingers played over his hard cock. The simple feeling of her hand sliding up his thigh had given him a rock hard cock, and now her fingers amplified his desire by fondling him teasingly.

Mike was so distracted by her caresses that he had no idea how the movie ended even as the house lights seemed to suddenly come on. Mike looked over at his mom and she looked back at him with a sexy, knowing smile. They ended up as the last two people to leave the theater because Mike needed time to let his hard cock subside a little. Even with waiting he was still glad for his long coat as his excited cock was bulging noticeably in his pants.

In the car Mike felt a wave of excitement when her hand settled on his thigh just over his knee almost as soon as he got settled in his seat. Mike started to drive and her hand immediately slipped up his thigh and straight to his cock again. At a stoplight Mike glanced over at her not believing his mom was acting like this. She simply smiled back and teased, "Eyes on the road, mister."

Mike had to concentrate hard on the task of driving as she teased him relentlessly. He groaned mightily when she opened his zipper and slipped her hand inside so she could continue caressing him through his boxers. She was only satisfied with that for a few moments, however, as her fingers easily found the front opening in his boxers before slipping inside and directly fondling his hard cock. As he approached his apartment building she pulled his cock out of his pants and continued fondling it.

When he pulled into his assigned spot Leslie moved so quickly and smoothly that he barely had time to register what she was doing until she was already leaning across the front seat of his car. She wrapped her lips around his cock with his tip inside her mouth and started to hungrily suck him.

Mike gasped in shock and excitement and leaned back against the seat. He took a quick glance around the parking garage to make sure they wouldn't be interrupted, but he honestly wouldn't have cared if the garage was full of spectators. Her hungry blowjob was so amazing and so unexpected that he could only moan softly and give himself over to her.

She teased and sucked him excitedly without pausing. It was clear she was anxious for him to cum as she sucked at him with a hungry intensity. Mike didn't try to hold himself back and let himself quickly build to his release.

When he came it was with a long moan and she eagerly consumed his cum as soon as it filled her mouth. With seemingly no effort she took and swallowed his cum easily despite the fact he shot many, many thick jets into her mouth.

Finally, when he had completely finished cumming, she let his cock slip out of her mouth and sat up looking at him with a sexy, teasing smile. He marveled that despite the cramped conditions and the intensity and volume of his orgasm that not a single drop of his cum had escaped her lips. Aside from the sexy smile and the gleam of lust in her eyes there was nothing about her appearance that would indicate that she had just taken a huge load of cum in her mouth.

"Let's go inside," she said softly as Mike quickly stuffed his cock back inside his pants and pulled his zipper up. His head was still spinning from the shock of what had just happened as he held open every door for her on the way up to his apartment.

As soon as the door to his apartment was shut behind them Mike immediately set about repaying Leslie for her wonderful surprise in the car. He embraced her in a hungry, lustful kiss and let his hands roam across her back and eventually down onto her soft ass.

They slowly moved beside the couch and Mike began to slide off her clothes. He started with her shoes and then slipped off her silky shirt and her pants. Only the vision of her body in her incredibly sexy bra and panties caused him to pause. If she had been thirty years younger she could have been straight out of the pages of a Victoria's Secret catalog. Even still, she easily looked hotter than most of the models in Victoria's Secret or the recently published SI swimsuit issue.

Mike gazed at her in horny admiration for a few seconds until she softly ordered him to strip. She helped as he pulled off his clothes and then knelt before him as she grasped the waistband of his boxers and slowly pulled them down his legs.

She didn't touch or kiss his cock and instead brought her mouth to his upper thigh near his hip. Mike groaned as she began kissing and licking her way up his hip and then across his stomach as her hands also roamed over his stomach and up his sides.

She teased him like this for a few more moments before Mike grasped her shoulders and pulled her to her feet. He turned her around until her back was facing him and smoothly opened her sexy bra. He pushed the straps forward off her shoulders as she slipped it off her arms and let it drop to the floor in front of her.

Mike pressed in closely behind her and slipped his arms under hers. In the next instant he was holding and caressing her tits as she leaned back onto his shoulder and moaned seductively. His original idea had been to set her on the couch and slowly and teasingly lick her pussy until she was screaming in orgasm. However, the feeling of her body pressed up against his and especially the way his cock felt pressed against her ass was more than he could resist.

He slipped his hands down her stomach and grasped her panties before easing them down her legs. They moved together to the couch and Leslie knelt on the seat facing backwards as she leaned against the back of the couch. This position perfectly placed her ass at the same level as his rock hard cock as he stood next to the couch. He moved behind her and grasped her hips as his cock seemed to guide itself inside her waiting pussy.

Having cum not too much earlier Mike was able to fuck her deeply and firmly without having to worry about keeping himself under control. Leslie reacted strongly and immediately to his fucking and he kept it up until she was teetering on the edge of cumming. She started her orgasm with a loud, long cry and Mike kept fucking her steady as he savored the way her pussy moved and quivered around his cock as she came.

When she finished cumming Mike kept fucking her until she told him to stop. He pulled his cock out of her as she spun around and then easily guided him until he was sitting on the couch. She lowered herself onto his lap, straddling him, with his cock inside her pussy.

She leaned back and looked down at him with lust in her eyes as she first started their fuck not by moving up and down, but instead by flexing the muscles in the walls of her pussy. This created the most incredible, wave-like sensation for Mike and he groaned wildly.

Leslie alternated between fucking him like this and riding up and down on his cock. She draped her arms over his shoulders and they regularly gazed into each other's eyes as she controlled their fuck masterfully for a long, long time.

The fuck finally culminated with Mike groaning wildly as he came deeply inside her pussy. Once he finished cumming he lifted her off him and they moved to the bedroom. Once there Mike finally acted out his original plan of licking and sucking her pussy.

Now it was not only her taste he was able to enjoy, but the deep, heady mixture of his cum and her excited pussy. He was in no hurry as he loved the sensation of being between her spread thighs like this, so he slowly and very deliberately continued his licking and sucking. Aside from the amazing taste and feeling of her pussy the other thing that was driving Mike wild was the sound of her excited moans and gasps of pleasure.

By the time Leslie was on the verge of cumming Mike's jaw and tongue muscles were aching from overuse as he fucked her and explored her pussy with his mouth. Her orgasm started with her body tensing tightly as she moaned deeply. Her pussy danced and trembled all around his tongue and he continued licking and teasing her until she had completely finished cumming.

After this they lay together on the bed holding and caressing each other for a long time until their caresses became more intense and excited and soon led to long and slow foreplay. The foreplay eventually led to a slow, teasing fuck in the traditional missionary position. They teased each other easily all through their fuck and finally brought each other to deep, intense orgasms at the same time.

After their long, powerful mutual orgasms they collapsed into each other's arms and fell into a deep, sound sleep. The next morning started with one more slow, perfect fuck. This time the fuck ended up with Mike lying on his back and Leslie sitting over him riding his cock. The sensations were beyond anything Mike could have dreamed. Nobody had ever so masterfully fucked him like this and Mike simply let the pleasure wash over him as he periodically reached up and caressed her tits. Again, they ended with an intense mutual orgasm that left them wonderfully exhausted as they held each other tenderly.

Following such a powerful, intense fuck to start the day Mike could imagine nothing better than a slow, lingering shower with his lover. His mom felt exactly the same way and, after lounging in bed for a while longer, they moved to the bathroom and climbed in the shower together.

They didn't fuck again, but they did stay in the shower slowly and lavishly washing each other for a long, long time. Mike washed her tits, pussy, and ass for many long minutes and made sure he didn't neglect any other part of her body as he lovingly washed and rinsed her. Leslie repaid the favor and let her soapy hands explore his entire body before she focused her "washing" on his cock, balls, and ass. His cock slowly grew hard under her soft and wonderful caresses, but both were happy to simply continue their shared shower as it was without advancing toward another fuck.

Reluctantly, they climbed out of the shower when the hot water supply in Mike's apartment started running out and the water started getting cold. After drying off they got dressed and decided to head out to a restaurant for lunch.

After lunch Mike drove his mom back to her house and dropped her off. She gave him a soft goodbye kiss, but she couldn't let the kiss linger too long or become too deep and risk having one of the neighbors see them doing something inappropriate. "I had a great night," she said in a soft, sexy voice before she got out of the car and walked to the front door. She gave Mike one final wave before she stepped inside and shut the door behind her.

Mike started to drive away and just a few houses later he saw Ms. Everhart coming down the path from her front door. She waved and smiled widely when she recognized Mike and he returned her wave with a quick beep of the car horn. Ms. Everhart had lived just two doors down from his parents as long as Mike could remember. She used to baby-sit Mike and his sisters when they were younger and remained friendly with his parents to this day.

He smiled devilishly as he glanced at Ms. Everhart in the rear view mirror. He imagined her utter shock and horror at finding out what Mike and his mom had just done the previous night and that morning. Surely, Ms. Everhart thought his parents were fine, upstanding people who would never be so depraved and "twisted" as to fuck their own children. Mike laughed and thought again how funny it was that just a couple of months earlier he had known nothing more than Ms. Everhart.

A few minutes later another thought entered Mike's mind. He knew that his dad was home because he saw his car in the garage when he dropped his mom off, and now he wondered what his mom was telling him. Surely, based on everything his mom had told him, she would tell his dad everything.

Mike wondered how his dad would react to hearing about how his only son had fucked his wife so eagerly and wantonly. He realized that his mom had probably told his dad all about the ski weekend and even about how she had felt Mike's hard cock when he was playing Santa, but still Mike felt somehow nervous about his dad knowing.

The next couple of weeks passed quickly and the next thing Mike knew it was nearly Valentine's Day. This year for Valentine's Day Mike had plans unlike any he had made before. Instead of his usual routine of setting up a fabulous date with his girlfriend or, if he didn't currently have a girlfriend, trying to set a date with someone from work or an old friend from college, he made plans to go out with his sister.

Under normal circumstances a date with your sister on Valentine's Day would be very bad news, but as soon as Lily had suggested they go out together he had eagerly agreed. He had told her he would take care of all the plans for the evening and he made reservations at a very secluded and romantic restaurant. For after dinner he purchased a couple of bottles of very expensive champagne, which he carried with him to Lily's door.

Based on their previous night together, Mike wasn't really sure what to expect from Lily even as he pulled up to her place. She had so surprised him with her strap on and had so completely controlled and dominated their fuck before that a part of him wouldn't have been surprised to find her in a full dominatrix outfit.

He knocked and only had a wait a few seconds before she opened the door for him. He was immediately floored by her appearance. It was both incredibly sexy and completely not what he had been expecting.

Her dress was very sexy and flattering. It really showed off her body and a perfect amount of her cleavage. Her shoes had tall heels that made her look sexy as hell as she led him into her apartment. Her make up was very soft and feminine and she was a complete knock out. She was definitely dressed a little more revealing than she usually felt comfortable and Mike appreciated her effort.

Mike complimented her often and when she was ready with her final touches she did a playful little twirl for him and said, "I'm glad you like it, little brother." Her eyes then flashed with a hint of mischief and she stepped close to him as she added in a sexy voice, "You don't look so bad yourself." As she spoke these last words her hand grazed over his crotch with a touch so feather soft Mike could barely feel yet still left him wildly excited when it was done.

Their evening out together was wonderful and romantic. They shared a couple of rounds of drinks together while waiting for their reservation and then continued with more drinks during dinner. The food was fabulous and Mike very much enjoyed talking and flirting with this soft, sexy version of his sister. They lingered at their table after dinner with both clearly enjoying their time together before finally going back to Lily's place.

All through their date Lily had been nothing but sweet, sexy, and even perhaps a little shy. She was nothing like the dominant figure that had so confidently tied him up and fucked his ass. This stark contrast of being with someone who was outwardly so sweet and sexy but who Mike knew was willing and capable of being such a kinky, forceful fuck was very exciting. He could feel himself being drawn even closer to his sister on a much deeper and more intimate level than he had ever felt for her before.

Back at Lily's place Mike popped open one of the bottles of champagne while Lily retreated to her bedroom. Mike grabbed a couple of glasses and went to join her, not sure what he would find when he arrived. Would she be waiting for him with the handcuffs and her strap on or would she have some other kinky game in mind for tonight?

Instead, Mike was only surprised by the soft, romantic beauty of her bedroom. She had placed dozens of candles around the room and had lit them all as Mike opened the champagne in the kitchen. The glow from the candles gave the room a wonderfully sexy feeling even without Lily's presence in the room.

This was such a stark contrast to how she had been the last time they were together and Mike was again struck by the complexity and diversity of desires of his sister. That she was capable of such polar extremes of behavior was something that really appealed to Mike.

Mike poured the champagne and set the glasses on the bedside table. He looked around wondering briefly where Lily had gone before he noticed the door to her huge, walk in closet was slightly ajar. It was hard to see with the soft glow of the candles as the only light, but he was sure he picked up some shadows of movement coming from inside the closet.

He turned away from the closet and looked at a new painting that Lily had hung on her wall. She always had great taste in art and Mike admired her latest print even if it was hard to see in the candlelight.

"Hmmm, champagne," she hummed softly from behind him. Mike turned and smiled excitedly at Lily as he picked up her glass of champagne and brought it to her.

When she stepped out of her closet she had definitely slipped into something more comfortable. She wore a silky robe that barely came down to the middle of her thighs. If she was wearing something under her robe it had a deep neckline because her robe was open well down to between her tits and he could see her cleavage and the inner swell of her tits.

Other than the robe the only obvious thing she wore was a pair of sandal type shoes with tall, spiked heels that gave her body a very sexy and seductive sway as she walked with Mike over to the bed.

This was the first time they had been together since Lily had tied Mike up and introduced him to the pleasures of being fucked in the ass with her strap on. It was already clear from their date that this night was going to be very different, and her look and behavior now only confirmed that.

They lounged on her bed sipping champagne and gently touching each other as they softly talked. After they had each finished a couple of glasses Mike was feeling very horny and more than a little intoxicated. The latter may have been as much from Lily's beauty and raw sexuality as she lounged in her silky robe and sultry high heels as it was from the alcohol.

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