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Charli The Poolside Cougar

Charli The Poolside Cougar

by five_inch_heels
20 min read
4.17 (25200 views)
adultfiction
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We had the house where everybody hang. Ask all my friends, they'll tell you the same. Was it the house or was it the gang. Or a phenomenon no one can explain? Lots of music, lots of games. Weekend parties we kids attended with our friends. And weekend parties we kids didn't attend. Parents only they said. Then Parent only. Dad had gone to work one day and never returned. Two years of grief turned up nothing. Mom went back to work at a cosmetics counter and doing some side sales work. That's all we were told. We'd visit the store sometimes while she was there in all her finest, but the side sales work was more of a mystery. On the road or so she said. But she was home nights and weekends doing what Moms do. Overall a great mom. She kept going to the parties though.

We were one of those families with similar sounding names. Mom was Charlene, but everyone called her Charli. Sis was named Carly after a famous singer. I was Carl, Jr.

Funny thing was, everywhere we went, strangers seemed to flock to Mom. Then I saw an actress on TV and knew why. Mom bore a striking resemblance to this actress, Joan Severance. I now understood why people would ask her for her autograph. Confused as to why this world famous actress and model would be in our midwest suburban town, they jumped at the chance to speak to her. Mom never told them the truth as she didn't want to dash their dreams tell them how wrong they were. But she made it clear she loved the attention and strived to dress as similar as possible, even styling her hair the same. She'd happily sign Joan's name as close to the original as she could.

Once me and my sister Carli were old enough to take care of ourselves if left alone, Mom would start taking business trips over night and every once in a while she'd be gone for a weekend. She would always leave dressed to the nines and with a huge smile on her face, but come home looking very tired and worn out. We attributed it to the travel and work sessions. We never knew just what those work sessions involved.

She never really said much about her early life, but hinted at having done some modeling and showed us a couple of catalogs with her in various dresses. But little else was ever said about how far into it she'd gotten.

Carli was a year older than me and we both went away to different colleges. Turns out neither of us liked it and had had more than enough as soon as we got degrees. We'd come home during breaks, or maybe travel some. Mom was always there and we all did the usual family things. But there were times when Mom and Carli went off on their own for a while. They said she was learning the business so she could work on her own. I guess for some reason I never really noticed the changes at first, but Carli began to dress a lot more like Mom. And mom dressed a lot more like a much younger lady, always focused on getting as much attention as possible. It started to feel strange when I went somewhere with Carli as she was always the center of attention too. When we all went together, it was even more interesting with so many eyes following us..

After our final college term, we both came home to what was supposed to be a Homecoming Party. It turned out to be a lot more in so many ways. More like a Coming Out party. The first couple of days home were setting up for the party, getting things arranged around the pool. Getting food and drink in. A small catering company was handling a lot of the details.

Our house is just a bit secluded at the end of a Cul DeSac, with a large yard. A hedge surrounds the entire yard and is at least six feet tall and several feet thick. No one can see through or over it and it deadens a lot of sound.

On the morning of the party, the catering company staff began to show up. Mom gave them some final instructions, then gave me a list of things to make sure they did. Then she and Carli disappeared into the house, telling me to handle everything and not disturb them. She said they had some things to do to get ready and they'd be back out after noon when the guests had arrived.

People began to arrive and though I knew some of them from school, most were unfamiliar. Really nobody from the neighborhood for some reason. Most everyone was in pool outfits, swimwear of various types. A few girls were in bikinis, other were in other suits or just shorts and tees. Some were in and out of the pool playing various games. Others just milled around and socialized.

There was a sudden quietness and everybody turned to looked towards the house. I followed their eyes and saw Mom and Carli walking out the house. My jaw dropped. Carli appeared first wearing a shocking pink string bikini that didn't really cover much and heels that seemed way too high.

Then Mom. There was a very audible sigh as she walked though the door and into the sunlight, stepping in time to the song Mustang Sally playing on the sound system. A powder blue bikini almost smaller than her daughter's only barely contained her breasts and the side strings of the miniscule bottom stretched high over her hip bones making her legs look even longer. Essentially she was almost nude in front of all these people masterfully strolling towards them in heels similar to Carli's. Her dark brown mane was blowing wildly behind her in the breeze. At 40, she didn't show her age even a small bit. Taut, toned and dynamite. The mile wide grin on her face told everyone how thrilled she was with the attention.

I wasn't sure whether to be proud or ashamed, or aroused at my mother and sister being so fully on display and commanding the attention of everyone there, young, old, male, female, friend, acquaintance or hired help.

The afternoon passed with little drama, but Mom and Carli made the rounds openly, getting very, very close to many of the guests. Even dancing close with several. When their bikinis needed some kind of adjustment, they did it right there with all watching.

After a few hours, many of the guests had left and the only ones remaining were a few younger guys. Mom mentioned something to Carli about her shoulders looking a bit sunburned. Opening a bottle of oil, she began to apply it to her daughter's bare skin. Of course that caused quite a stir and soon she handed to bottle off to a couple of the guys to take over. And take over they did, oiling down a lot more of my sister than just her shoulders. Carli laid face down on a lounger and soon hands were oiling her back and legs and everything in between.

Not to be left out, Mom mentioned some about needing some oil too and laid down on another lounger face up, spreading her feet just slightly. In no time at all, three guys were on her oiling every exposed inch of her body. By this time Carli had rolled over and was now also face up with hands everywhere.

They looked over at each other and almost in unison lifted their small triangular bikini tops up and over their heads, then reached down and untied the sides of the bottoms. My mother and sister were now fully nude and being oiled down by several young men who were essentially fondling them at will as I watched from a short distance. I expected it to be over soon and the two of them would come to their senses and go back in the house, leaving me to send the guys away.

I was wrong.

Mom effortlessly stood up on those insane heels and faced the guys. Her breasts never dropped at all. They stood out as firm and proud as any half her age. Carli rose and stood beside her. Their bikini bottoms remained on the loungers.

"You know guys, I'm not sure it's fair for my daughter and I to be standing here naked in front of all of you while you're still dressed. Let's see what you've got in those shorts. Carli, dear, why don't you help them?"

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"OK, Mom."

My sister went to them one by one, hugged them pressing her naked body against them, kissed them with a full open mouth kiss, then knelt down in front of them and slid their shorts down. And then took each one of their stiff cocks into her mouth briefly before moving to the next one.

Why didn't I do anything? Why didn't I leave? Would you? Hell I think I was enjoying the show as much as any of them knowing why I couldn't be included. I just wished one of the other girls had remained also, but they hadn't. I had no one to do anything similar with.

Mom then started down the line, doing the same full body hug and open mouthed kiss. Rather then using her mouth though, she just took each cock in her hand for a moment, then rubbed it along the inside of her naked thigh. You could see the expression the the guy's eyes, hurting and hoping for more.

"I think you'll do just fine" she said to one as she held on to his cock and led him back to the lounger.

"Carli, have you made you choice?"

"I sure have" she replied as she pointed to one and used a hooked finger to summon him to follow her.

My mother and my sister then laid back on the loungers again and opened their legs wide. They used their hands and fingers on themselves as their selected mates moved closer to watch. Mom made it very clear she had inserted her finger into herself as deep as she could. Pulling it out, she offered it to her guy who who eagerly took it in his mouth and sucked on it for all he was worth.

Carli on the other hand had taken a more direct approach and her guy's face was now firmly against her cunt, his tongue lapping away at her. Mom was now sitting up in her lounger with her lips working the head and shaft of the cock that was certain to soon be thrusting into her. But first, she took it into her mouth and made a show of working it all the way in. My mother seemed to be a fairly accomplished cocksucker.

I can't even begin to effectively relate the feelings rushing through me as I watched my mother and sister lean back, open their legs and let these two guys they didn't really even know plunge deep into them and begin to stroke in and out slowly at first, then more rapid.

I lost track of time as the rest of the guys stroked them selves and let go on the faces and breasts of the two women in heat. Before the evening was over, each of them had let more than one guy take the place of the first. It wasn't long though before everyone was sitting up in regular chairs, drinking and chatting as though nothing had happened. Well aside from the fact they were all still nude and openly touching each other.

But then it was done, the guys were gone and it was just us three again. Oddly, it wasn't awkward at all. It felt great and we were all smiles, yet we knew there would be a lot to talk about tomorrow. For now, we all went inside and to bed. Our own separate beds.

Tomorrow came as did the cleaning crew to haul away whatever was left. Not surprisingly, Mom and Carli slept in quite late. When they came outside they were dressed sort of frumpy in jeans and sweats. Not much was said, only that we'd all talk later. They day went by with mundane tasks and errands.

There was a brief dinner meal of sorts before we got together in the den. Mom began by showing me a book she had put together over the years. There were a number of pictures of the kind I had seen before, catalog shots and general modeling shots. Some of her as an auto show model from when she was around 20.

The next few pages were a bit more of a shock. Clearly from a major men's magazine with her in various outfits or skimpy lingerie and then fully undressed. A few shots were quite over the top with her legs spread wide and the camera focused between her legs. There was one session with her posing with a male model, also nude and in very erotic and explicit shots, their hands all over each other. In one she was holding the guy's erect cock while looking into his eyes. In another, they were laying in bed and it seemed pretty clear the guy was deep inside her. She smiled coyly explaining that he wasn't supposed to do that, but she didn't stop him and loved how kinky it made her feel knowing men all over the world would see that picture.

She went on to explain how she had also stripped some over the years, did a few adult films and some other things she wasn't quite ready to discuss yet. She said a lot of this happened before Dad disappeared, but he knew about it all and supported her all the way.

The discussion went on for quite a long time and got into how Carli had become so open about it all and willing to participate, even in front of me. They explained that some of the trips they took together were for erotic events at clubs and other situations where both of them had sexual encounters. They then showed me a similar book of hers and told me how she had been dancing nude in clubs for the last couple of years at college. They had both gotten so far into sex and nudity that they no longer felt any shame and wanted to include me to whatever extent the could. The whole party thing had been a set up to see how I would react with so many other people around. They wanted to do it that way in case I reacted badly. They were prepared to go back in the house and call the whole thing off if necessary, but really didn't want to. They wanted me to see it all. They wanted the shock factor rather than just telling me about it first. They made it clear there would be many more gatherings and I would be free to attend... and watch... at will, but no more. They drew the line at certain things that might be illegal. I'd even be able to help my sister primp and get ready if I wished, but probably wouldn't go any further. Probably? Interesting phrasing

Mom would be off limits in all ways other than to watch her in action and drive to parties if she needed a ride. She implied there would be a lot of things I hadn't seen yet and that it might seem she was treating me badly in front of others but that it would be an act for their benefit.. a show or performance of sorts, but that she would always make it up to me later. They both also made it clear that my darling sister Carli was actively dating several men of various ages and that I might need to work with her on some occasions. I still wasn't sure what to expect.

Part of that became clear the next Saturday afternoon. I was informed that I was to be there and that Carli would be away so only Mom would be handling whatever came up. It turned out there was a lot more to it than that.

There were no caterers this time as the group was to be only a few people and that I would be serving them all. As the guests began to arrive, my stomach began to knot up. These were all guys from high school. All guys my age and that I knew, some of them were close friends. It seemed like a normal pool party we'd had many times. This time there wasn't a lot of attention like before when Mom came out in her bikini and slipped into the pool. It was obvious this was not the first time they'd been here. as they all swam together, playing with each other openly. There was no hesitation at all about physical contact between her and them.

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The bit about playing along and she'd make it up to me later started to come into focus as six of my friends and my mother, twice their age, all but ignored me while freely touching, hugging and fondling each other. They only time they talked to me was to say they needed another drink or more snacks and send me into the house to get whatever else. Or to make other requests.

"Carl, be a dear and come over here for a minute" she directed.

"I'd like you to untie my bikini top and remove it."

I sort of half whispered to her "Mom, I thought I wasn't supposed to..."

She cut me off sharply. "Carl, I'm not asking to to do anything other than undress me so your friends can see me naked... again", making it even more clear this wasn't a first.

Continuing, "Honey, it's an important step. It tells me, and all of us standing here that you're OK with all of this. It says you're not angry or upset in any way and are willing for us to continue. Now please, I'd really appreciate it if you'd show us all that you think this is OK by removing my bikini for your friends."

I did as she asked, untying her top and removing it to expose her perfect breasts.

Then, as she took a step with one foot to spread her stance, "Thank you dear, Now untie the sides of my bottom and pull it away so you friends can see my pussy."

I know I probably turned a few shades of red as I did what she asked.

"Thank you again dear, now take that away as I won't be needing it any more today," motioning me to take her now discarded bikini back into the house.

When I returned is when things started to get even more awkward than they had been. My friends from High School had all removed their shorts and the seven of them were all nude standing in a line facing me. Mom was in the middle with three guys on each side, her arms around the waists of the two next to her. Each of those two were holding one of her breasts.

"Now, Carl, I told you a number of things the other night, but now it's time for a bit more. Since your Dad left, I couldn't bring myself to try to get too close to anyone else. But I've still needed attention, affection and sex. A lot of sex. This body isn't really an accident. I work hard to keep it looking like this so men will like seeing me and wanting to be near me. For the last two years, while you were at college, your friends have been helping me with that. At first it was workouts on the gym equipment, then some things out here by the pool. Sex wasn't involved at first. Whenever they came home on break, one of more of them would visit with me and help me train."

"The sex came about almost by accident one day. It just happened. But once it did, there was no going back. Boys talk you know and the tale got around. Then I just couldn't say no and it went from there. Before long, all of them had been with me more than once. We'd fulfill each other's needs for sex. And it's always been just pure sex. Fucking and sucking. Twenty year old guys fucking the forty year old neighbor and mother of their friend.. No strings. It makes me happy and it makes them happy. And I hope somehow it will make you happy knowing your mom feels so free and easy doing these things and enjoying it so much."

Trying to take it all in, watching them all trying to decide how I was going to react.

"Now, you can stay out here and watch, or you can go back inside. That choice is yours, but we're going to do what we've done so many times before. Most, if not all of your friends here are going to fuck me this afternoon. You watched last week and you've seen pictures so you know I mean it will happen. As for me, I hope you stay and watch. It will mean a great deal to me knowing you care enough and trust me."

One of them had moved around behind her. His arm was now wrapped around her from behind and his hand was between her legs stroking her neatly trimmed pussy hair.

"The next move is yours and you are free to do whatever you wish. You can go back in the house, or you can call the name of of one of your friends here. That's the guy whose cock you want me to take into my mouth first."

I thought for a minute. I was stunned at her blunt language and demeanor. She was right of course. I'd seen it all. I'd seen both her and my older sister get fucked by more than one man. But none of them were guys I knew and it wasn't quite as direct as this was playing out. It was a party and it happened. Here's she's asking me to pick one of my friends so she could suck his cock. First. Knowing full well she'd take others and then have them fuck her. No matter what I did.

I stammered out the name of the guy standing behind her stroking her cunt.

"Thank you Son. Now go over and have a seat and watch me suck his cock close up."

Close up, it was. She led him over in front of the chair I was sitting in, knelt down not more than a few feet in front of my face and began to work on him. First with her fingers, lips and tongue. She expertly ran her bright red nails along the underside of his shaft and caressed his balls. Her mouth opened and she took just the head at first then worked her way down the length without stopping. As her lips got to his hair, she looked up with her piercing ice blue eyes first at him, and then at me. She backed off and took him again, then again and again.

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