Introduction

 

Sometimes you look for one thing, but you find something else and it is far too good to ignore. That was what Carson Thomson thought these days. After a profitable, but relatively short, career as a professional football player, he retired at thirty and lived the good life. He bought a small mansion in a gated community in the always balmy southern area of the country. Initially it was like a prolonged vacation spent golfing, clubbing, and bedding hot women.

Eventually he got to know his neighbors and found his neighborhood was full of wealthy older couples. The men were usually high-level corporate types, most in their fifties or sixties. But several had wives in their late thirties and early forties with their kids now in college. Since they had never worked, and caring for their offspring was no longer necessary, they were bored and had a lot of free time on their hands.

Once the three most sexually deprived ladies of the neighborhood realized that there was a younger unattached hunk living in their purview, they all set their sights on getting to know Carson. Being an affable guy, he welcomed their subtle advances at first. And when each of them got more insistent about what they wanted from him, he obliged and soon found himself sleeping with three different women.

As fun as that was, keeping them from learning that they were all jumping his bones was not easy. He told each of them that if anyone found out about their affair, he would dump them and deny it ever happened, and that worked for a while. But he had a better and more interesting idea, one that could keep them all in the mix, and would give him leverage to keep it that way.

It took him a few weeks to acquire the necessary paraphernalia he needed to make it work. He used some of it to secretly record a tryst with each of them. He knew none of them wanted their husbands to discover they were unfaithful, fearful of losing the wealth or prestige they enjoyed. Two of the three were dumb enough to sign prenups, and adultery was the main way to trigger it and leave them with next to nothing.

Since they were all in some form of unspoken competition with each other, his plan would take that to a whole new level. Carson also liked his women more amenable than these ladies were, and decided a lesson in humility would do them all a world of good. But even as he prepared to initiate his plot, he had no idea how far it would go, or how it would change all the players, himself included.

 

 

Chapter 1: Meet the MILFS

 

Penelope 'Penny' Allworth was a striking redhead who just turned forty, but she looked like she was in her twenties. At five and a half feet, her 120-pound body was distributed in a nice hourglass shape that still turned most male heads. She had set her sights on and bedded Carson first, but as intense as their sexual interludes were, the fact that she was cheating on her husband left her nervous all the time. Not because she felt guilty for cheating on him, she knew he had his own mistress, but because her prenup would screw her if he could prove she cheated on him.

She had decided that she had to end it now, even though the last two months had been the most sexually satisfying of her life. She had married her husband when she was only eighteen, because he knocked her up and back then he was an honorable sort of guy. But he resented it, and though he treated their daughter well, Penny never felt he ever loved her. Since he was forty-five when they married, already wealthy and a confirmed bachelor, she was hoping his drinking and poor diet would end him before she got too old.

Then this young guy shows up and rocks her world, but despite how Carson had sparked a new gusto for life in Penny, she reasoned ending it was the prudent move. The trouble was, she had made this same decision than last four times she hooked up with him, but she chickened out instead. This time she was determined to tell him that it was over, she was just too uptight to deal with it anymore. That did not stop her from bathing, shaving, and dolling herself up before leaving to meet him. Or, for that matter, packing the bag she would need for the week long getaway he wanted her to spend with him.

 

***

 

Stella Armstrong was in a similar situation, her fling with Carson was a bit unnerving for a woman who had always played by the rules. But since her husband was always out of town and, and even when he was around, he had not had sex with her for two years. She was pretty sure he was sleeping with someone else, but she had just ignored it. She was just thankful that her son was grown and in the military with a good career ahead of him.

When Carson came to town, moving in right next door to her house, she could not fail to notice him. She was so interested she did something that she rarely did, she baked cookies and took them over to his house as a welcome basket. Stella found Carson was not only sexy looking, but his charm had her swooning in short order. She was his second MILF conquest, but this one he chose to seduce.

Stella was a stunning blonde ex-surfer girl, and at forty-four she was more voluptuous than Penny. She was a couple of inches taller than the redhead, but she weighed nearly thirty very curvy pounds more than her. But she still exercised daily and every bit of her plentiful body was firm, except of course for her squeezable 38DDD tits. Carson sensed they were real and confirmed it the first time he slept with her. Her anxiety was not based on losing money, as Stella was far more worried about the embarrassment of sleeping with a man more than a decade younger than her. When Carson joked about her being a cougar, Stella became very upset, and that told him how to hook her.

 

***

 

Finally, there was the runt of the litter, Margaret 'Peg' Olsen, a petite woman that stood only five feet tall and weighed just under a hundred pounds. To augment her diminutive stature, she always wore at least four-inch-high heels. She also bought herself a nice pair of tits to add some curves to her body. She was the oldest of the three, but at forty-four, she still looked much younger. She had a pale complexion that was offset by her jet-black hair, but sadly she had to dye it to keep it that way now.

She was a spoiled heiress that had married a man her father chose for her when she was just eighteen. He was twenty-five years older than her and got the naïve girl pregnant before her nineteenth birthday. That was the one saving grace from her marriage, Peg's daughter Anna, who was now twenty-five and had just passed the bar exam. She was now fielding offers to join prestigious law firms.

Peg's affair with Carson started much like the other two MILF's did, as friends first, with the benefits coming a little later. Peg had not had sex in five years, her septuagenarian husband had a bad heart and liver, and was too run down to have sex anymore. Considering he was also fat and bald; she did not consider it a big loss. But, like the other two, it left her ready to fall for the sexually dominant Carson. He made her feel like she was a girl again, the kind that just learned how good sex could be, only thirty years too late.

Since her family was an old and established name in high society, and her daughter was about to start a career as a lawyer, Carson knew exactly what he would use to bring Peg under his sway. All three were vulnerable to having an improper affair with Carson come to light, and after recording some very kinky trysts with all three of them, he had what he needed to start the game he planned to play with them.

He had the goods he needed to make sure the humiliation factor was strong enough to assure him that they would rather die than let anyone find out what they had done with him. He got each of them worked up, and then he convinced them to play a little bondage game. Once they were spread eagled on his four-poster bed, Carson gave them so many orgasms that they screamed and cried out the most perverse things. He made them beg for it when they reached the brink of climaxing, and they all responded like deranged sluts for his hidden cameras.

Once he had damning evidence on all three, and with a few days for them to digest how intense it was when they got a little kinky, he arranged to meet all of them on the same day. He had never attempted that before, nor had he wanted to, doubting he could handle all three at once. But this time he was going to bring them all together, and since they already had a convoluted way of hooking up and not being seen, his plan required careful timing.

Carson was set to pick up Penny at noon, Stella at three, and Peg at six, all of them were expecting to spend a whole week with him. Since they lived only a few miles away from a large airport, they utilized the long-term parking lots to meet without being seen. He would wait a few blocks away from the lot, and once he saw them drive by, he would follow their car into the lot. Each of them would park and he would stop in front of where she parked, while she got into his back seat and hid under a blanket. He would then drive back to his place and park in the garage, so no one would see anyone, other than him, coming or going into his house.

He returned by half past twelve with Penny, as she had already abandoned her idea of ending it, at least until after a week of more great sex. When they entered his house, she tried to tell him how wrong this was, but he answered by kissing her so passionately that she quickly succumbed to him. He was insistent that after the way she responded to being tied up and teased, he wanted to take it a step further.

She tried to resist, but he had already stoked her up and had left her hanging, so she agreed to let him do it again. Penny was too worked up to object when he had her sit on a wooden armchair before securely roping her from her neck to her ankles. Once she was tied to the chair, with her legs parted and bound to the front legs, he wedged a vibrator against her sex and used heavy duty duct tape to glue it to the seat. She almost objected again, but he was too quick when he used the tape to seal her lips shut. After blindfolding her, he looked down at Penny and smiled.

"Well my dear, looks like you are mine for the week. The game we will be playing is simple, I am your Master and you are my sex slave." He smiled again when she shook her head to say no, as it was exactly what he expected. He then added, "Since you seem less than eager at the moment, I will give you some time to relax and consider the possibility," while Penny's head never stopped objecting.

He stepped behind her and said, "Sit still woman or I might have to slap those beautiful tits of yours with a paddle."

That comment made Penny freeze, not sure if he actually said he would harm her, but too stunned to disobey his order. In fact, her pussy actually trembled when he spoke to her in such a stern tone. She convinced herself that he was joking and just decided to play this game, not that she had much of a choice at this point. But she did shiver when he placed his hands on her shoulders, surprised that he had moved behind her and she did not hear him do it.

"I am going to put headphones over your ears in a moment Penny, they will play sounds that will relax you if you let them. I know you can feel the nice big vibrator pressing against your pussy. I will be giving you short doses of it at random, and if you are lucky, you will have a few orgasms. But you will need to let it happen, resist it and you will just get frustrated. Now just sit back and relax," Carson said. Then he covered her ears with the large headphones that cut her off from the world.

Penny heard the sounds of waves crashing on the beach, and at first, she hated it. But after a few minutes the vibrator turned on and she shuddered from the sheer intensity of it, it was so strong that damn thing felt like it was rattling her bones. She instinctively tried to back away from it, but she could only lessen the pressure, not avoid the potent vibrations that lit her sex up like a Christmas tree. But now that she tried to avoid it, as he said, the vibrator stopped and she was left panting like a dog.

It took a quite a while for Penny to calm down, and given her situation, she had no idea that she was alone in the house with Carson already on his way to collect Stella. It took even longer for the vibrator to start up again, but after the first assault, she had found the sounds in her ears helped to keep her calm. But she also resolved to go for it if it started again, and when it did, she did.

But what she did not know was that Carson was not only monitoring her, he was controlling the vibrator. There was nothing random about what he was doing to her. He watched her on the screen of his smart phone, which also activated the vibrator. So, when he saw a much different reaction to the second round, he stopped it after a much shorter time, right when she was getting close to coming of course.

Since he was ahead of schedule, he had almost an hour to tease her like that, driving her to edge four more times before he had to leave her dangling so he could procure MILF number two. Stella was far less reticent than Penny, and within an hour he had her bound the same way to a chair of her own, in a room adjacent to where Penny was now desperately trying to have an orgasm. He was making such good time that he had more than an hour to toy with both of them. Just before he left for his final pick up, he activated both their vibrators at once, and moved Stella into the same room as Penny before cutting them off again.

Stella was loving this game and she was close to finally coming when she felt her chair tilted backward and dragged for a short distance. She was too busy trying to grind her sex into the vibrator to think anything of it, but once she stopped moving, so did her chance to come and she groaned in frustration. This was an exciting game for her, but she thought that it might drive her crazy if he did not let her come sometime soon. She could tell how soaked the seat was under her rump with her sex feeling wetter than she ever remembered.

Carson now had the two of them facing each other from just a few feet apart, but made blind and deaf, neither could tell whether anyone else was there. They were both trapped inside their own private worlds, and the sounds of the surf calmed them down after every frustrating go around with the evil machines taped between their legs. Neither knew that there was a subliminal message under those sounds, simply the words relax and submit repeated over and over. He had used a similar technique in his playing days that helped him relax and focus for games. His intention for these women was a little darker. They were too strong willed and he hoped he could erode that enough to keep the advantage, especially with three women to manage at once.

Once he had acquired the final piece of his erotic puzzle, and had Peg as naked and helpless as the other two, he realized there was no turning back now. In order to get Peg up to speed, he took a slightly different approach to getting her into a similar state of mind as Penny and Stella. Instead of starting in the playroom he built in the basement, Carson took Peg to his bedroom and bound her wrists to the tops of his bedposts.

Peg was the most adventurous of the three, as she was also the one that had the most dismal sex life before she met Carson. She gave him no trouble as he bound her ankles apart and then blindfolded her, offering no resistance at all when he taped her lips shut. When he put the headphones on her after explaining the game he was playing, she was so into it that she slowly gyrated to the sounds of the sea.

He let her get into it while he checked in on his other two MILFs. He remained with the oblivious Peg, and used his phone to toy with Penny and Stella again. He saw that both of them had their heads bowed, clearly exhausted from the hours of teasing and frustration they had already endured. He gave them another jolt that brought them around and left them fruitlessly struggling against the tight ropes when they were left on the brink and unsatisfied once again.

Then he turned his attention to Peg, her lithe little body with the big fake tits looked better than ever to Carson. Though he was frustrating the other two before setting their sexes on fire, he was planning the opposite approach for Peg. She would be inundated by orgasmic intensity. He would keep it up until she was so spent that when he took her down to meet her friends, she would be in the right state of mind.

As he collected the toys that he was going to use on her, Carson felt a thrill that he could only compare to the feeling of playing in a big game. This was not much different, but it was a bold choice, given he had many moving parts to manage once he got his plan rolling. He felt confident though, as he prepared to rock Peg's world with an erotic adventure like nothing she ever experienced.