Family Business Ch 05

For the next several months Mike's life settled into its new rhythm. On the one hand he couldn't believe he was living what was nearly every man's fantasy lifestyle. He was conducting torrid affairs with two very beautiful, sexy, and yet very different women.

One woman, Lily, was close to his age but still a few years older. Lily had a fetish for "controlling" their fucks that Mike really enjoyed. Sometimes she would tie him up and sometimes she would simply use her strong will and actions to direct Mike to do whatever she wanted. Mike was surprised by how much he liked having her take control, but what surprised him even more was how much he thoroughly enjoyed having her fuck his ass with her strap on dildo.

Then there was his other lover, Leslie. Leslie was much older than him and carried herself with an experienced confidence that was very sexy. She wasn't as openly kinky or wild as Lily, but she still had plenty of surprises for Mike and never failed to drive him to new heights of lust.

The fact that Mike's two new lovers were his older sister and mother was enough to make him occasionally question the sanity of what was happening. To make things even more intense, he knew that both Lily and Leslie, not to mention his dad, knew of his affair with the other and that both not only condoned but also approved of it.

Now that he was fully a part of his family's incestuous secret he wondered how he had ever managed to not know what was going on previously. He had yet to actually be with either of his two younger sisters, Mary and Nancy, but he had watched the video of Nancy fucking his dad and he knew that his mom had also slept with her.

Mary didn't seem as involved in the family affair as the rest of the siblings, but Mike knew she was aware of the situation and had been a willing partner before. Lily told him that she and Mary had fucked on a few occasions.

Sometimes Mike fantasized about his younger sisters and wondered if fucking them could possibly be as intense and satisfying as being with Lily and Leslie. Sometimes he fantasized about being with his whole family at once as they engaged in a huge family orgy. He always came very hard after these fantasies and then felt a wave of disbelief wash over him that something as totally forbidden and extreme as a family orgy no longer seemed beyond the realm of possibility.

For the next couple of months Mike continued his wild affairs with both his mother and sister. Neither one became an every night sort of sexual relationship. Sometimes they would only fuck once every couple of weeks and other times they would get together a few times in a week. It often depended on their work and other social schedules.

Through this all they continued their "normal" family gatherings, either in smaller groups or as a whole family. To Mike's disbelief these gatherings still seemed comfortable and not at all awkward despite his simultaneous, open affairs with his mom and sister. The normalcy also remained in spite of the fact that his dad knew of his affairs and had even double fucked his mom with Mike on one occasion.

Things continued in this blissful state until near Mike's birthday. Both Lily and Leslie talked of having a big family party to celebrate. It turned out to be a few days after his birthday, on a Friday night, when they finally decided to try and get everyone together and go out for a family night on the town.

Mike went to the bar where they were going to meet and ordered a drink. Right on time Lily and Leslie entered the bar. Mike waved at them and they joined him at the table.

"Ready for your big night?" Lily asked.

"Sure," Mike answered.

"Well, it looks like it is just the three of us tonight, so what should we do?" Leslie added as Lily ordered them a round of drinks.

Mike asked about the others and Leslie told him that Nancy and Mary each had plans with their respective boyfriends. John had really wanted to come but he had some sort of crisis come up for work that he needed to go to the office to figure out.

Mike was secretly thrilled to have Lily and Leslie to himself. Despite the fact that the three of them had never been together sexually and it had never even really come up as a point of conversation, it was still something that Mike thought about often.

After finishing their drinks they went to a nice restaurant that was one of Mike's favorite places. They enjoyed a great meal together before Lily suggested they visit this new club on the edge of town she had read about. Mike was a little surprised since it seemed like the kind of place Nancy, his youngest and wildest sister, would suggest, but not necessarily the sort of place Lily would frequent.

It was in a part of town that they very rarely went to and that, combined with the dark lighting inside the club, left them feeling pretty anonymous as they danced and mingled. They still weren't overtly sexual with each other just in case there was someone who did recognize them. They knew that it wouldn't be good for the company if word of their family affair were to get out. Still, the relative anonymity allowed them to be just a little more open and free than they might be otherwise.

Having two such different and sexy women dancing and hanging out with him made Mike feel very confident and horny. He noticed that more than a few of the other guys in the club were watching him with his two dates and he could practically feel their jealousy. A couple of them even asked if Lily or Leslie wanted to dance with them, but they politely declined every offer making Mike feel even more excited.

Eventually they left the club and decided to go back to Lily's place for a nightcap. On the drive back Mike was left very aroused after the casual contact and touching that comes with dancing together in a crowded club. He thought he could feel a sexual energy and tension filling the car.

Between their dancing and the crowd at the club all three had become quite warm. As they drove both Lily and Leslie had the slightest flush to their cheeks and just a tiny trace of sweat still on their skin. In Mike's eyes this made them both look even more radiant and sexy.

Inside her apartment Lily went to fix them a round of drinks as Mike and Leslie sat on the couch. Lily sat beside Mike so he now had a woman on either side of him as they talked and finished their drinks. Near the end of their drinks Mike and Lily made eye contact and there suddenly appeared a smoldering desire in Lily's eyes. They were quickly drawn toward each other and met in a deep, passionate kiss.

The kiss lingered for several long minutes and Mike became lost in her hungry mouth and the aura of desire he felt radiating off her. When the kiss parted they gazed into each other's eyes before melting together again in another long kiss.

This time when the kiss parted there was something about Lily that was almost even physically different. Her body language had changed and there was something about the set of her face and the look in her eyes that let Mike know right away that she was about to take control.

Instead of saying anything Lily simply stood and took Mike's hand. Mike stood and followed her directly into the bedroom with only a brief glance back at his mom.

Once in the bedroom Mike moved to kiss Lily again but she put her hand on his chest to stop him. "Stop," Lily said. "Strip," she commanded in a tone that let Mike know he didn't have much choice.

Mike quickly stripped and was soon standing completely naked in front of his older sister. Her eyes scanned his naked body as if she was appraising a purchase. "Lay down," she ordered. Mike could already feel himself getting excited in anticipation of what was about to happen.

Just as he expected and hoped, she took his wrists and cuffed them to the headboard so his arms were stretched almost straight up over his head. Once he was restrained Lily stood staring down at him. He couldn't wait to feel her touch, but instead she abruptly turned and left the room.

Mike was alone for far longer than he expected as he strained to hear something, anything, from the other room to figure out what was happening. His mind created wild images of what could be happening in the other room between his mom and sister.

Perhaps they were kissing, or maybe even fucking on the couch. Perhaps Lily had returned to the room and poured a drink for her mom as if nothing out of the ordinary had happened in the bedroom. His cock remained rock hard as he thought about the two of them together.

Finally, Lily returned to the bedroom leading a blindfolded Leslie by the hand. Lily didn't look any different from when she had left the room and, other than the blindfold, Leslie also appeared the same as when Mike left her on the couch. Lily led her mom to the edge of the bed and stopped her by putting her hands on Leslie's shoulders. There wasn't anything about the way Lily was touching her that was overtly sexual, but Mike couldn't help but notice there was something sensual and tender in her touch.

Lily moved behind her mom as she whispered, "What do you want?"

Lily let her hands brush across Leslie's shoulders causing her mom to moan very softly instead of answering Lily's question.

"Do you want to fuck him?" Lily asked.

"Yes," Leslie sighed.

"You want to fuck your little boy, don't you?" Lily asked. Leslie moaned affirmatively. Lily began elaborately describing how Leslie wanted to feel Mike's rock hard cock inside her steaming pussy, fucking her until he filled his mommy with a huge load of cum.

Simply hearing Lily's nasty description was driving Mike wild. His cock was rock hard and throbbing. He began squirming slightly in his heightened lust as he watched his sister continue teasing both him and their mother.

"Suck him," Lily commanded. "Suck your baby boy's cock."

Leslie carefully crawled onto the bed feeling her way toward Mike under the darkness of her blindfold. Her hand first touched his leg near his knee and she settled down beside him as she let her hands slip up his leg very slowly.

"Suck him now," Lily ordered as she grasped the sides of Leslie's head and guided her mouth directly toward Mike's cock.

Leslie parted her lips and hungrily sucked his cock into her mouth causing him to moan wildly and thrust his hips upward. Lily kept her hands on the sides of Leslie's head and guided her movements up and down on Mike's cock. Mike gasped and stared at the incredibly kinky sight of his sister using his mom's head like a sex toy to play with his cock while his blindfolded mom enthusiastically licked and sucked at him.

Lily kept this up for several minutes before she released her mom's head and sat beside them for a moment. She watched approvingly as Leslie continued her wild sucking on Mike's cock before she stood up and moved behind Leslie.

Leslie continued to suck on Mike with increasing intensity and lust as Lily began to pull off her mother's clothes. Leslie occasionally shifted her position to allow Lily to strip her and before long Leslie was completely naked. Lily stood back for a moment staring at the two naked bodies in front of her with an excited gleam in her eye.

Leslie continued to frantically suck on Mike. He was already close to cumming and seeing the combination of his mom's naked body and the way Lily stood staring down at the incestuous situation that she created quickly pushed Mike beyond his control. He groaned loudly and pushed his cock up frantically as he started spurting heavy blasts of cum into Leslie's waiting mouth.

Leslie hungrily sucked down his cum and kept her lips firmly wrapped around his shaft throughout his entire orgasm. As soon as he stopped cumming Leslie lowered her head all the way until her lips were pressed against the curly hair at the base of his shaft. Mike let out a long groan when he felt the tip of his cock entering her throat and marveled at how easily and quickly she had deep throated him.

Mike stared at Leslie while she continued to expertly suck and lick at his cock even as it started to loose some of its stiffness. He had become so engrossed in her blowjob and how intense her mouth felt around his cock that he had completely lost track of Lily. He glanced up briefly and noticed that Lily was no longer standing there watching them, but he had no idea how long she had been gone or where she went.

A few minutes later Lily suddenly reappeared beside the bed. Lily was also now completely naked and she was wearing the now familiar strap on dildo that she had fucked Mike with on several occasions. The vision of her standing with her fake cock pointing directly out in front of her sent a rush of lust through Mike both from the way Lily looked and from the flood of memories that came back to him thinking about how it felt to be fucked by her.

Mike wondered briefly what Lily planned to do, but it soon became clear when he saw what she had in her left hand. She had also brought back a second set of cuffs, which she easily locked around Leslie's wrist as soon as she pulled Leslie away from Mike's cock and positioned her mom on her back beside Mike on the king sized bed.

Before locking the second cuff Lily passed the leather strap holding the cuffs together through the headboard of the bed leaving Leslie still blindfolded and now tied to the bed with her hands together above her head in virtually the same position as Mike.

Mike stared in wild lust as Lily crawled between her mother's legs and easily guided the strap on inside Leslie's waiting pussy. Leslie let out a long groan and Lily immediately settled into a steady tempo of thrusts.

Of all that Mike had now done and seen, this image was likely the hottest, most wanton thing he had ever witnessed. Their soft, excited bodies pressed together erotically during their deep fuck. The sight of their bodies reacting to each other and to their growing lust was wildly arousing.

Despite having Leslie tied up and completely at her mercy, Lily didn't pay any attention to Leslie's tempting tits, either with her mouth or her hands. Instead, Lily focused all of her energy on fucking Leslie.

Most of the time she kept her hands on the bed on either side of Leslie to hold herself up, but occasionally she leaned down and let her body lay directly on Leslie. When she did this their tits and stomachs rubbed together erotically under Lily's constant thrusting and Mike tried to memorize exactly how their bodies looked.

Lily expertly fucked her mom like this for a long while. This was the first time Mike had seen Lily using the strap on with someone other than him, and his "outsider" perspective allowed him to notice several things about his sister. It was clear, if he hadn't already known from the times Lily had fucked his ass, that Lily was very experienced fucking like this. She moved confidently and easily in what was usually the man's role, and her movements definitely suggested she had done this many times before.

The other thing that Mike could clearly see was how much Lily enjoyed fucking like this. Her face was a mask of pure lust and the look in her eyes was one of near animal intensity and desire. She fucked her mom eagerly and excitedly, undeniably relishing her dominant role.

Many more long minutes passed and both women were clearly reaching the heights of their lust. Leslie groaned and wriggled excitedly and the intensity and tempo of Lily's thrusts increased as she too began groaning from her pleasure. As she lay on top of Leslie, Lily made a long, hard thrust as deeply inside her pussy as possible. Mike could see by the way her ass muscles strained that she was pushing into Leslie's pussy firmly as she began grinding her hips in a side-to-side motion.

Mike guessed Lily was doing this to heighten her own pleasure from the small nub on the inside of the strap on that was designed to tickle her clit. It was also immediately clear that Leslie loved this as she gasped and struggled against her restraints.

Leslie's orgasm started only moments later and her whole body shook powerfully as she cried out with pleasure. Mike wished he could join their union and be a part of the intensity of the orgasm, but he could only feel their legs and hips rubbing against him, as he remained firmly cuffed in place.

Lily continued grinding herself against Leslie all throughout Leslie's orgasm and then for only a few moments longer before she too began a powerful orgasm. When she started cumming she pushed herself up on her hands and continued pushing hard into Leslie as she kept grinding her pussy from side to side.

Lily's moan was almost primal and Mike stared at the way the muscles in her stomach danced and convulsed as she came and bucked her hips against her mom. They stayed like this all through her orgasm.

By the time they finished their wild fuck Mike's cock was standing rock hard and ready for relief. He couldn't wait to see what Lily had in store for them next.

It didn't take Lily long to let him know of her plan. As she softly pulled her dripping wet fake cock out of Leslie, Lily opened her eyes and looked over at Mike. Mike had seen the glint of wild excitement and lust in Lily's eyes before and he knew right away that she wasn't done with her strap on yet.

Lily quickly grabbed a tube of lubricant and, in a manner Mike was now becoming accustomed to, she began working the gel into and around his asshole. When she finished preparing him she leaned over to her mom, who was still lying blindfolded and cuffed on the bed beside Mike, and opened the cuffs around her wrists.

"Don't move until I tell you," Lily commanded. Leslie remained still but Mike could tell by her body language that she was straining to listen to the sounds of Mike and Lily to figure out what was happening. Mike wondered if she would ever guess that her oldest daughter was getting ready to fuck her only son up his ass.

Lily returned to her spot between Mike's legs. She took one leg in each of her hands before spreading them wide and pushing them up towards Mike's face to rotate his asshole into better position. In her excitement Lily hadn't done as complete a job of preparing his asshole for the fuck as she usually did, so when the tip of her fake cock pushed against and finally through the tight ring of his asshole Mike groaned in a combination of discomfort and excitement.

Their mom trembled in excitement as Mike groaned. Mike realized the anticipation must be driving her wild. Lily expertly worked the dildo back and forth and finally had it driven all the way inside Mike's ass as far as it would reach.

"Take off the blindfold," Lily commanded. Leslie quickly reached up and yanked the blindfold off. There was no mistaking the surprise and wild lust in Leslie's eyes as she stared at the scene before her.

"Oh my God!" she gasped in complete shock. The gleam of lust in her eyes, the way her nipples seemed to immediately become rock hard and pointy, and the mask of lust she wore on her face immediately showed that she was as excited as she was surprised by the scene before her.

Lily continued fucking Mike while Leslie stared as if frozen by her emotions. After a while longer Lily touched Leslie's arm as if to break her trance and sternly said, "Sit on his face."

Leslie moved so quickly over Mike's face that it was like she had been coiled and waiting for a command. She brought her pussy down on Mike's face and he immediately reached his tongue inside her and lapped excitedly at her heavy wetness.

Leslie groaned and settled over Mike's face momentarily before he felt her shifting her position again. In the next moment he felt his mom's mouth engulf his cock once again. He groaned wildly into the embracing wetness of her pussy and then hungrily drove his tongue into her pussy as Leslie seemingly tried to force the entire length of his cock into her mouth in one motion.