A Milf at the Country Club Pt. 11 by SearchingDOM,SearchingDOM

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. Here’s a woman who discovers that some pain heightens her experiences and starts to like it.

A Milf at the Country Club

Part Eleven

Kimberly transitions from whore and slut to pain slave and likes it also.

Kimberly had spent the entire night having this man pinch, twist, and otherwise abuse her most sensitive clitoris and nipples. She knew she could take that again gladly to experience the massive full body orgasm that followed. She also knew that every time he did something to her, she couldn’t have even suspected it, all he had done was beyond her possibility of predicting, her experience base was just not expansive enough. Now she was informed with that word again, Learn, that she was to experience something different.

Mr. Raymond: “Marcus, put the head of your cock in her mouth and have her suck on it until its full and rigid. If she makes one moan, grunt, squeal, cry in pain or ecstasy, shove it all the way down her throat in one movement. She will either learn to breath around it, or she will pass out from lack of air. Under no circumstances are you to let her wiggle loose of you in her throat. If she passes out, we will just wake her up again and try it over and over until she learns how to take it.”

Kimberly had been slowly fucked the entire time this was playing out and could feel the sensations starting to build. She felt him reach down and gently pull almost out and Shove back in, causing her body to jerk, but no sound came from her mouth. Then she felt the plug pulled out, so the widest portion was holding her anus open, while he bent it from side to side like a lever prying her open even more. Now she knew she was in uncharted waters for her, but also knew he was perfectly comfortable sailing here.

She felt her plug being removed, and she could only suspect that his cock would replace it, as that’s the way it happened in every porn video she ever saw. But this wasn’t to be any cheap porn movie, this man was going to not only own her body, but her mind, her free will and heart. She felt that her plug was now being replaced by a finger that went slowly into her without stopping until it hit the third knuckle, then it withdrew and entered with a second finger all the way to the knuckle, and then it came back with a third, and finally four fingers entered her but this time only up to the second. He held steady pressure, forcing her to take them as far up inside her as she could, while twisting them back and forth. Then he spoke and revealed something to her that she hadn’t yet begun to think of.

Mr. Raymond: “Marcus, pleas pull out of Kimberly’s mouth, but stand at the ready to perform your duties should she make any sound other than answering my questions. Kimberly, I am going to ask you a series of questions and I want you to answer loud enough for everyone to hear you, do you understand?

Kimberly knew not to voice her answer yet, so she looked him in the eyes and nodded yes.

Mr. Raymond: “Tell our guests what I am doing right now my slut.”

Kimberly: “You have four fingers in my ass all the way up to your hand sir.”

Mr. Raymond: “And why would I be doing that Kimberly?”

Kimberly: “You want my ass stretched out enough to take your cock or anything else you wish to out up there sir.”

Mr. Raymond: “And do you want me to do this Kimberly?”

Kimberly: “Yes, yes sir I do.”

Mr. Raymond: “And why would you want me to do this slut?”

Kimberly: “I want you to be able to use my body for any purpose you wish Sir, and I want my body to please you while you use it sir. I want to become your full-service whore without any limitations sir.”

Mr. Raymond: “You please me whore, but there is much yet for you to learn. If I asked you to sit and take Marcus up your ass, and then asked you to take one of his friends in your ass at the same time, what would you say?”

Kimberly: “I would say I will do my best to perform any act for you, sexually or not, no matter how deviant or embarrassing or painful it might be to me sir.”

Mr. Raymond: “You are going to be a good full-service whore Kimberly. Now you’re going to try some new sensations to eventually pleasure yourself, and please me at the same time.”

Kimberly just nodded yes and laid her head back over the table, looking directly at Marcus’s cock. Mr. Raymond twisted and removed his fingers from inside of her and replaced them with his cock. Then she felt two fingers in her pussy invading all the way up to his hand. Then three fingers and then four invaded her womanhood as far as he could push them in. Then a sensation she had not felt before he curled his fingers and started rubbing her from the inside. She had heard about this but never had the nerve to ask Chad to do it to her, but this man was not finished, he was far from it. As he curled his fingers up and outwards, he used his thumb to put pressure on her swollen nub. So now he had his fingers inside her bent that his fingertips rubbed her, and his thumb bent so its tip rubbed her. This sensation was forcing her in a direction she had not considered yet, it was stimulating, strange, and she was in a position that she could never get away even if he was killing her with pain.

Mr. Raymond: “Are you ready my sweet little slut?

Kimberly: “I’m ready for you to do anything you wish sir. I am yours to use as you please.”

Kimberly was doing her best to be as good a slut as she could be, but she knew she had to pull every bit of determination she could muster to get through the next few hours. Between his cock in her ass, and four fingers in her pussy, no it’s just a cunt now…his cunt, has made her fuller than she has ever been, even with trying two dildos in her at home. To add to that feeling, this man is doing things with his fingers she hadn’t even dreamt of. Now he was using her body in strange ways, penetrating her in a perverted manner, in front of everyone she previously thought of as friends and acquaintances, and she was enjoying it.

Mr. Raymond: “Kimberly, I want you to describe everything you feel me doing for our friends here tonight.

Kimberly once again just nodded in agreement, as she felt his thumb go up and over her clit.

Kimberly: “You’re rubbing my clit from the outside and the inside, clamping down on it almost pulling it to you with your fingers.”

Then he really pinched it between his thumb on the outside and his fingers on the inside, rolling it back and forth causing her a pain she couldn’t describe to herself, let alone anyone else.

Mr. Raymond: “Does this hurt my dear, does it hurt your cunt? Tell us Kimberly.”

Kimberly: “Yes, it hurts beyond belief in a way I can’t even put into words.”

Mr. Raymond: “Do you want me to stop my slut, or should I go further?”

Kimberly: “I want you to continue until you think I deserve to cum.”

Mr. Raymond: “Very good Kimberly, there isn’t a woman here tonight that doesn’t know what you’re feeling right now slut. They are all my whores and I’ve used them just as I’m using you right now.”

That revelation sent her into a state of confusion. Trying to think as this pain shot through her, she wondered how he owned all these people. And their husbands Must know, or he wouldn’t have advertised that fact. What the hell was going on? What did she get herself into? This can’t be a one-night thing, can it? Her mind raced with questions until he brought her attention back to him by using his thumbnail over her clit, scraping it causing her unbelievable pain and agony. Then with one last hard compression, he roughly pulled his fingers and thumb off her clit without lessening his grip. She thought he was going to rip it off her cunt altogether but instead the release sent her full on into another body quaking orgasm she didn’t expect. Just as she opened her mouth to vocalize her feelings, Marcus shoved the entire length of his cock through her lips and down her throat.

With her body convulsing from her orgasm, her struggling to get a breath, Marcus not allowing her to pull off his cock, and Mr. Raymond fully in her ass she just kept quaking and jerking and bouncing up off the table until she lost consciousness and just laid there motionless. Her jerking and spasming had milked Marcus empty, and Mr. Raymond enjoyed her ass clinching down on his cock just as much.

Mr. Raymond: “Shaw, wake her back up, and make it quick.”

Mr. Shaw came over and snapped open a tube of smelling salts and she jerked back into motion. She choked and coughed sending Marcus’s cum flying in the air and landing all over her body. Heaving for each breath, all she could do is “Grrrrr” on every exhale, causing her ass to clamp down in pulsing manner upon his cock, which put him in a euphoric state. When he regained his hold on reality, Mr. Raymond gave out his next instructions.

Mr. Raymond: “Mrs. Powell, get Marcus and another helper to help you get her back in the suite, clean her up, dress her, and have her put in the front seat of her car. Shaw, get things ready for tomorrow night, we’ll be here with her Husband and make sure Marcus is working.”

Marcus and another man picked her up and took her to room 101, laid her in the shower and proceeded to scrub her clean inside and out. When done they dried her and dressed her and took her out to her car as instructed.” Mr. Raymond joined her and drove her home, helping her in the house to the bedroom, and sat her on the bed. She wasn’t 100% but she was aware enough to understand what was going on.

Mr. Raymond: “Strip and get on the bed face down and ass up. From now in you are always naked in front of me unless I tell you otherwise.

She did as she was ordered without a thought that she was making herself available to him in the bed her and her husband slept and conceived her two daughters. She heard him undressing behind her but didn’t move to see. She felt him climb up on the bed and stick his finger in her ass.

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