A Milf at the Country Club Pt. 19

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 Nineteen

Kimberly learns and enjoys her first formal gangbang

Kimberly had been sexually active for many years before meeting her master, and thought she knew everything about sex that she should or could. This past week taught her there was much more for her to learn than she ever dreamed, and she was looking forward to it. She experienced pain and pleasure beyond any limits she heard of, even porn videos didn't begin to touch on what she enjoyed, and she was sure she would willingly do anything master asked of her. He hadn't told her what was to be her next experienced, but she felt good about it. Dressing up in her new clothes and prancing around in front of her mirror, made her feel pretty and loved. Chas meanwhile moved all his things into one of the girl's rooms and moved them into the same room to share, and he made the guest room for Tabitha as Mr. Raymond ordered him to do. When Tabi showed up it surprised them both, as they hadn't got any instruction from Mr. Raymond or Mrs. Powell, but Kimberly was excited, regardless, this meant master would be coming to get her.

Tabi joined Kimberly in her room and sat down on the bed to talk with her. They discussed her new sexual flowering, her unwavering devotion to master, and her needs to be submissive to whatever he wanted. Next, she had Kimberly strip and started getting her ready for the evening to come. She took dark red lipstick and expertly put it on her areolas and nipples, and the same with her lower lips. She used dark black on her sphincter, then did her makeup and hair. The necklace that attached and pulled her breasts up to pint straight out, and two earing's, one said slut and one said whore. Then she dressed her in a light blue elegantly flowing see -Through dress without any under garments, allowing full view of her pussy when she walked or sat. Kimberly looked at herself in the mirror and couldn't believe how pretty and drastically slutty she appeared, but she liked it, after all walking naked this last week made her not care who saw what.

Master showed up late afternoon to pick her up, and he greeted her with a loving embrace and kiss, then she immediately dropped to her knees to suck his cock as normal. After she pleased him, he had Chas take her to clean up the edges of her mouth where she lost a tiny bit of master's seed, then they left. Master gave her her next instructions inside the car as they were pulling away.

Mr. Raymond: "My sweet slut, you have pleased me in so many ways, and to such lengths, I cannot convey to you how happy I am. But there are some new guidelines for you to live by, first one being I don't want you silent all the time, just during your orgasms. Second you can always whisper in my ear if you have any questions. Third, we need to find out how much stamina you have, and that's what tonight is all about. My son is home from college break, and we're throwing a party at my estate with 100 of his male friends. You are going to be the entertainment for the evening, and I expect you to please them all in any manner they ask. Can you do that for me my precious whore?"

Kimberly just nodded yes and lowered her gaze, but it wasn't embarrassment that made her do that, it was the thought of 100 Young cocks to make her orgasm repeatedly. She knew she was going to enjoy this night immensely and wanted to remember every minute of it forever. She thought to herself, what would Chas think or do if he saw her fucking that many college boys in one night, and she smirked and chuckled. That night being trapped in the brass machine taught her to just go to her sexual happiness place and enjoy the orgasms, even when she didn't have a drop of cum to give, she still felt them even more intensely. When they got to his estate, he just kissed her on the forehead and walked her out back to the pool.

She saw a huge pool, grassy yard next to it, a pool house with bar and living area, and a bed at the perfect height to lay down and be fucked on. There were also cameras set up for still pictures as well as one for videos in front of the bed and behind. She thought it wonderful that this night was going to be recorded for her to watch in the future to relive it over and over. Around the pool were about 50 pool chairs set up for the guests, and another 50 in the grass, each with a marker setting next to them on tables so she knew she would be doing some traveling. She took a seat next to master at the house side of the pool and waited for her next instructions to come.

As she watched the young men file in, she was salivating, one by one, wearing trunks and sandals, their hard bodies just begging her to fuck them. She was already wet when Mr. Raymond addressed all guests in one short speech.

Mr. Raymond: "Gentlemen, I want you to meet my beautiful slut Kimberly, and tonight she will be your entertainment and whore. I wat each of you to leave her with your cum in all three holes, mouth, pussy, and ass. After you have made your three deposits, I would like you to take a marker and write your name somewhere in her body, showing that you have thoroughly used her body. She is yours to do with what you wish for this one night, so enjoy yourselves because she likes to please and is very good at it."

First up was Mr. Raymond's son, well endowed like his father, he was about nine inches and the girth of a polish sausage. He stripped Kimberly and laid her on the bed before taking her pussy for the first time tonight, whispering in her ear that 100 boys are going to fuck her every way possible tonight, and she just smiled. He started slow and gentle and picked up speed and intensity as she responded to his cock. She was pleased with his staying power as he fucked her for 20 minutes before unloading deep inside her, giving her the first of many orgasms for the night. Before she could breathe, the next boy took his place and three more showed up around her head. Being fucked by one, sucking another, and serving two more with her hands she was servicing four at a time, and found she was never happier.

Mr. Raymond was overjoyed to see her performing so well and enjoying herself as she serviced these boys. After ten of the boys gave Kimberly her prize, Mr. Raymond got up and went into the house, and was gone for just a short time before he sat down with a wooden box on his lap. Kimberly looked at him for his approval when she noticed it and started wondering what was in it. He got up and walked to whisper in her ear.

Mr. Raymond: "Don't you worry yourself about what I'm doing, from what see you're doing fantastic, so pay attention to what you're doing."

She was pleased to have him tell her she was doing well, and it loosened her up a little more, so she dove in on the cock in her mouth and got very handsy with the other two. She could hear the boys muttering, "This whore is great" and "She sure can suck a cock". She felt heavenly inside hearing these young boys talking about how well she was doing, "a feather in her cap" so to speak. Then she started to feel that now familiar feeling of someone gripping her of someone squeezing her clit and massaging it up and down. She turned her head as much as she could and saw Master performing his ministrations on her. Now she was 100% into Cumming and she wasn't going to waste that feeling, especially with young boys using her body like they were.

The boys were astonished and stopped when they saw Kimberly's face. She was mouthing "Oh my, oh fuck, I'm going to cum right now", then just making grins and contorted faces. Mr. Raymond calmed the boys by explaining that she doesn't make noise when she Cums, they just shook it off and continued their pleasure assault on her body. Kimberly was in ecstasy knowing she was going to have this all night and going to Cum so many times she wouldn't be able to count. But none of that seemed to matter to the college boys, they just wanted some woman to fuck ruthlessly all night, and she was More than willing to be that woman.

Three orgasms later she was only up to boy #15 Cumming inside her, with each thrust he pushed out the deliveries the last boys left behind. She was enjoying this night as only a true whore and slut could, and she was proud that she was master's whore and slut. After the 15^th how left his deposit along with the others, master stopped the action and took her into the pool house where two pool bays were waiting at a table. He simply handed her over to them and they took her to the shower to clean her out for the next round. They had her bend over with one in front and one behind, the front boy holding her up and the back bot using a hose to flush out her sticky pussy. While bent over she noticed the bulge in the pants of the front boy and waisted no time pulling his cock out and sucking him until he came in her willing mouth, while the boy behind dropped his pants and entered her now clean pussy. The boy in her mouth was quite large and she took him in steps until the boy behind rammed her as he came and forced her throat to accept the others cock. She dutifully swallowed him while the other washed her out once again.

As she returned to the pool, master motioned her over to him, and pushed her heels apart as she stood in front of him. He inspected her piercing and pulled her pussy lips apart to inspect the rest of her. When he was finished, she thought she was done but he had other instructions for her.

Mr. Raymond: "Turn around and Ben over at your waist. I need to put a larger plug inside you to stretch you for tonight's activities."

She did as she was told and she felt significant pain as he pushed and wiggled her new plug in place, realizing it was much larger than anything she has worn so far, and when she stood it made a huge impact on the inside of her ass, stretching her wider than she had felt before. Then he motioned her to go back and continue with the next 35 boys who were waiting naked in a line. As she walked, she could feel the new plug pushing her sphincter open, and she knew master would not have done this unless she needed it. As boy number 16 approached, she could see he was about 8-inches long but very big around. As he entered her already used pussy, she could feel him pushing against her new butt plug. It was a sensation she had not felt before, but she quickly learned to enjoy feeling that full inside. With the new sensations she got to another orgasm quickly and just embraced it as she was being fucked by this strange boy.

By now the boys had a significant amount to drink and they weren't just fucking her anymore, they were ramming their cocks inside her and treating her like a real whore. Being impaled on all these young strong cocks was sending her mind back to that spot where she is just in a state of constant orgasmic pleasure, and she took the next 20 boys happily. They gave her a series of rough and somewhat sadistic fucking, but she enjoyed each one of them orgasming another five times. She heard that she was getting sloppy inside again, but no pool boys came to take care of her so she walked into the pool house to clean herself. She was met by five workers who stared at her like they never saw a naked woman before.

Pool boy #1: "There's the slut I told you about, grab her guys and lets have some fun too."

They took her to a locker room bench and laid her down face up, and in no time, she had one cock in her mouth and one in her well used pussy, plus one in each hand. The fifth boy took a thin leather strap and whipped her from waste to neck while the others used her mercilessly when master walked in. The boys came to a halt and just backed away from her and he picked up the leather strap and beat them ruthlessly. Once he disciplined all five boys he took Kimberly by the hand and helped her up.

Mr. Raymond: "Clean out your stuff and get out. If I ever see anyone of you again you will regret that day. Come Kimberly, you still have work to do."

She took her place where she had been all evening and welcomed the coming cocks like a champion. After she fucked the rest of the boys without cleaning in between, master came over with a strange looking plug. Instead of being solid, it looked more like a flower with folded up petals and it had a dial on the bottom. After he inserted it, master turned the dial and it expanded inside her effectively locking itself in place, and locking the cum of all those boys inside her. Then she was flipped over, and the big plug was removed from her ass, and the boys started over with her. After having worn the large plug, she didn't feel any pain from the anal assault, she just enjoyed feeling these young boy's cocks exploring the depths of her ass.

As the anal portion of this evening continued, the boys had her stand and bent her over pillows, so her head was down, and her ass was up in the air. Along with the party gaining steam, the alcohol content of her cock holders was increasing to the point where her as was just being hate fucked. Ramming their cocks in and out of her rear end along with slapping her ass cheeks and pulling on her clit with the roughness of a bull rider. It was obvious to Kimberly that this part wasn't going to be as the pussy fucking before, and she was tingling with anticipation.