This is a story about a woman who thinks her life, and Sex life is slipping away. Unaware that she is in the prime of both, she reaches out to what she perceives as the only options available to her. To make this point clear, I tell you that women in their late 30’s and 40’s are at their most sexy and sexually appealing. This is a story about a woman who discovers pain heightens her experiences, and she likes it.

A Milf at the Country Club

Part Twenty-Six

A special end to a special night, Kimberly’s first threesome with Master

Master proudly walked both of his sluts naked through the house, not that this never happened before, but seldom did he take a pair into his private bedroom, but tonight was not a normal night. As the walked in the foyer Bernard was standing there waiting for them, but more important any instructions master may have had for him.

Bernard: “Good evening, sir. Good evening miss Kimberly. Good evening miss Diane? Will you need anything from the staff this evening sir?”

Mr. Raymond: “Yes Bernard, I will need housekeeping on stand by and please inform Marcus we may need his assistance this night.”

Bernard: “Mr. Marcus had not yet returned from the errand you sent him on tonight.”

Mr. Raymond: “Bernard, how large are you?”

Bernard: “I am a healthy nine inches sir.”

Mr. Raymond: “That will be fine. Please be on standby until Marcus arrives back at the estate.”

Bernard: “As you wish sir and I will get housekeeping ready for you any request or need.”

Mr. Raymond: “Thank you Bernard and send some drinks up to my bedroom.”

Diane whispered to Kimberly that Bernard was one powerful fuck, and nine inches was conservative. They both giggled like little schoolgirls as they walked on master’s arm up to the room. When Bernard showed up with their drinks, Diane patted his Ass and gave him a quirky smile.

Bernard: “May I suggest to sir that your recent hire, Don, is also available. The word on him is that he has been confused with the equine’s down at the stable.”

Mr. Raymond: “That may be useful information for the future, but for tonight either you are Marcus will do just fine if I need you.”

Bernard: “Very well sir, ring if you require anything else sir.”

Kimberly looked at Diane and whispered, “Equine, doesn’t that mean horse?” Diane giggled and told her that it was strictly prohibited to interact with any staff in that manner without the direction of master.

Mr. Raymond: “That’s correct Kimberly, the staff here knows to never touch any slut unless I instruct them to. I’m running a business here and I can’t have my house turning into a slutfest or orgy. Besides your cunts belong to me and nobody touches them unless I say so. Do you understand that Kimberly?”

Kimberly: “Yes master, absolutely.”

Mr. Raymond: “Diane will you get you both cleaned up and ready while I make a few calls?”

They both padded of to the bathroom arm and arm and shut the door behind them to give master his privacy. Diane being more experienced with the workings of master’s house and his individual sexual wants, she proceeded to clean Kimberly and warn her not to break any rules this night. They took the opportunity to kiss, massage and even lick each other but not to completion knowing Master would not have approved, but the did get each other excited for the night to come. Diane gave Kimberly one last warning about violating master’s rules in his bedroom and told her she would take the lead if necessary. Then they just waited to be summoned to master’s bed.

Mr. Raymond: “Sluts, are you ready to continue?”

They both came out smiles and jubilance on their faces when master asked Diane to come stand before him.

Mr. Raymond: “Diane, are you sure you want to join us for the night? You’ve had troubles in the past fulfilling tour role in my bedroom before, and I don’t want to see that happen again.”

Diane: “I have come a long way and wanted another chance to serve you in this way. I also want to be the plaything of you and Miss Kimberly. I am willing to endure and enjoy any situations you wish me to master.”

Mr. Raymond: “As you wish Diane, go to the cabinet, and bring back eight lengths of the red rope. Kimberly, get up on the bed and Diane will teach you your submissive position.”

Kimberly got on the bed on her knees, and Diane positioned her with heels together, knees spread far apart, Ass on her ankles, and her forearms in the small of her back with her head bound. Knowing what master wanted she took the same position next to her and whispered, “Don’t speak until he speaks to you”. Master took two pieces of rope and draped one over each women’s shoulders, hanging between their breasts and down their backs. Kimberly couldn’t dismiss how soft the rope felt, almost like is was made out of expensive silk, then thought of course it’s silk, what else would this man use. He walked behind then and bound their forearms together in the small of their backs and bound their heels together with another length. Then he looped another length from their knee, through the bindings on their arms back to the other knee, effectively binding their legs spread wide open. He then got behind their shoulders and gently laid each woman on their backs. Kimberly was unsure what was to happen next but Diane had been down this road before and knew she was about to be tested, so she whispered to Kimberly, “Do nothing, say nothing”. Master got out a unique set of nipple clamps from the cabinet and attached them to Diane’s nipples. They had allegator teeth on the inside, and a tiny screw sticking up from one side of the clip, right above where it attached to the sensitive nipple above where it clamped on. After installing them on Diane he screwed a small birthday candle to each screw, pointing up directly above the already swollen nipple, and he lit both.

Mr. Raymond: “You see Kimberly, Diane has promised and failed me twice in the past, and I want to make sure she can meet the commitment she now makes, so we will experiment with a little pain first.”

As the candle burned the Hot wax ran down right in to her nipples causing her to jerk, but not a sound came from her mouth. Once the nipples were covered in wax the pain receded and she continued on without incident, but Kimberly was getting worried about her now found friend.

Kimberly: “Master, don’t I get to play also? Why is Diane getting all your attention?”

Mr. Raymond: “Kimberly Stop! I know what you’re trying to do. Don’t ever interfere with me testing another slut. You know better slut; you’ll only make it worse for this whore.!”

Master turned back to Diane and reached between her legs, and noticed she was wet just from the nipple pain. He turned his attention to her clit, stroking it up and down giving her pleasure, then he headed it between his thumb and forefinger and heard her breathing increase, then started pulling it in and out to really get her juices flowing. She was building to an Orgasm with this action, so master would speed up then slow way down trying to edge her towards a bigger Orgasm. Fast and slow, in and out, rolling it in his fingers, she was being to tremble, but not from pain. Master knew this whore and he knew what made her get excited, and that she didn’t like edging, she would much rather cum again and again. He played with her for fifteen minutes bringing her to the top of her sexual thrill, then stop and allow her to settle then do it again. With her mouth shut and her eyelids clamped tightly, she endured what master was doing to her Pussy.

Mr. Raymond: “Do you want to be my whore, Diane?”

Diane: “Yes master, I want you to do whatever you wish to me and make me cum.”

Mr. Raymond: “Then cum like the slut I know you can be.”

He pulled out on her clit and stretched it straight outwards before letting it snap back, sending her knot her first of many massive orgasms for the night, yet she remained quiet. He then reached between Kimberly’s legs to grab her clit, but he just pinched it sending immense pain through her body and spoke to her.

Mr. Raymond: “Why did you try to interfere with my training of Diane? You know the rules and you know your now going to be punished for you indiscretion.”

Kimberly: “Yes master, Im sorry Master, I will never interfere with you again.”

Kimberly had shown master she didn’t enjoy this type of pinching, but she did enjoy the orgasms it summoned. So, master held her there letting the throbbing be front of mind for her, and when he let go she went into her normal orgasmic state like a rocket taking off. He laid Kimberly on her back and positioned Diane in position to lick her Pussy, head down and Ass up. With her hands bound behind her she could only support herself on Kimberly’s already sensitive Pussy, and she licked and sucked on that throbbing clit for all she was worth. Meanwhile Master got behind her and entered her from that position, playing with her plug pulling it out and pushing it back in, over and over. Then he reached down and untied her hands, allowing her to perform more comfortably on Kimberly, and with her hands Free, the rope on her ankles loosened allowing her to gain a better position for master to use her.

It wasn’t long until both women were getting ready to cum again, and master was waiting for this moment, so he sped up his rhythm and fucked her harder. First Kimberly, then Diane, they both burst into another Orgasm, and master unloaded inside Diane Pussy. He told Diane to remain on all for and he untied Kimberly, then had Diane lay back and Kimberly suck his cum from her pulsing Pussy. Kimberly did a dutiful job cleaning her, but also pleasuring her nub with her tongue, keeping Diane on edge as master knew she would. Then master put Kimberly squaring in Diane’s mouth with her facing him and gave her Diane’s legs to hold up and open while he removed her plug, then replaced it with his cock. This time he was not gentle with his action as he slammed in her Ass, withdrew, and slammed back in over and over. He knew from experience Diane didn’t have Anal orgasms, so this was just a Free Anal fuck for him. He was pleasantly surprised when Diane came from his Anal assault, and she came hard not being able to control her body from shaking and quivering beneath him which made him cum deep inside her.

Mr. Raymond: “Wow slut, where did you learn to do that?”

As she shook, she brought Kimberly to another Orgasm, and she fell back against the headboard. Huffing and panting trying to catch her breath, she answered master’s question.

Diane: “I’ve been practicing with vibrators and dildo’s but that the first time I even orgasmed from it.”

Mr. Raymond: “You two go in the bathroom and clean yourselves up. Don’t forget the lube and plugs, the ones with tails this time, then wait for me here on the bed.”

Master went into a room just off the bedroom marked “Private” and closed the door behind him. The women went and cleaned up in the Shower, lubed each other, chose plugs for each other, installed their plugs, and went back to the bed to wait for master’s return. They played with each rubbing and kissing and hugging they were enjoying each other’s company and bodies. Master returned and instructed them to put on their heels and go out onto the rear patio, and he followed them down. When they arrived, they saw seven staff members assembled, four Men and three women waiting for them. Master stood them in front of the small crowd to make an announcement.

Mr. Raymond: “Everyone here knows Diane and the attempts she made to become my whore in the past, and you’re also aware that even though she tried, she could not accel in that position. Tonight, I announce to you that Diane has made the successful journey from part time slut to a full-fledged whore. She will also be promoted to my personal assistant and oversee running my activities and help with the planning of my Sex parties.”

The group applauded Diane and her promotion, then dispersed to go back to their duties leaving Master Diane and Kimberly. Master led Kimberly to the pool, removed her plug and they both got in where the water was at three feet in depth, where he put her hands on the edge of the pool with himself behind her. He had Diane sit directly in front of her with her legs spread wide, signaling to Kimberly what he wanted her to do, and she started licking her Pussy while he entered her Ass in the water. He slowly fucked her while she sucked on Diane’s Pussy and clit, and he grabbed her nipple piercings to pull and stretch her nipples. They continued in this manner for what seemed a half an hour before master filled Kimberly’s Ass with his seed, and Diane was close to exploding. Master pulled out and left the pool while Kimberly still worked in Diane. When Diane did finally cum, she squirted all over Kimberly’s face which had a huge smile on it. Kimberly got out of the pool and went to master to clean him up once again, and Diane got in the pool to wash off, then joined them.

They all got up and went back upstairs for a night of sensual three-way gratification between them, and they fell asleep on either side of master massaging his body. Master woke to Kimberly lightly kissing him on the lips and Diane gently sucking on his cock until he came in her mouth, and she shared her reward with Kimberly’s mouth. They all started to get up when master called to Diane.

Mr. Raymond: “Diane, you may now dress in any manner you wish, but you must always be lubed and plugged just like Kimberly. Bernard is setting up an office for you close to mine, and he will provide anything you may need to tend to your new responsibilities. I will see you downstairs and we will go over your ides in my office later this morning.

Kimberly wiggled her way to the bathroom with a smile on her face and blew a kiss towards Master. He went into the room marked private and got showered and dressed for the day. Both women felt good about the new arrangement, but Kimberly felt more like a meaningful companion than just his slut and whore. She didn’t know what the day was to hold so she didn’t dress, she just waited to see what was asked of her.

Bernard entered the room with a small young woman behind him, who he introduced as Kathy, her new lady. She was dressed in a short flowered flared skirt and a light blue button up top which showed off her cleavage. She asked Kimberly if she wanted to dress and was told that she would rather remain naked until she found if she was needed.

Kimberly: “Bernard, who do I speak with about obtaining more tailed plugs for master.”

Bernard: “You have a driver and car and a lady to accompany you if you need her. Your driver has a card to cover any purchases and he will carry any items you buy, and he knows where to go for anything you might want. Your lady is your companion if you wish her to accompany you while shopping or any other activity.”

Kimberly: “Kathy, are you ready to go shopping with me while naked?”

Kathy: “Your state of dress or undress does not bother me here or in public, and if you want me to join you, I will do that also ma’am.”

Kimberly: “You will strip and go shopping with me naked?”

Kathy: “Yes ma’am, I prefer not to wear clothes whenever possible. I wear clothes only because I have not been told what you or master Raymond wish of me.”

Kimberly: “Well then, call down for the car, lose those clothes and lets go shopping then.”

Kimberly felt a little excited to have a new playmate, so she wasn’t the only one walking around town naked. And this shopping trip was hound to be exciting considering what she was shopping for.