📚 charli the poolside cougar Part 2 of 4
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Charli The Poolside Cougar Pt 02

Charli The Poolside Cougar Pt 02

by five_inch_heels
18 min read
4.39 (6400 views)
adultfiction
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Sometimes Mom had a need to take time off from all these encounters for a while. She needed to regroup and recharge herself as a person, a woman and a mother with a family. She'd just stay home doing various hobbies and work from home assignments as a consultant. Her time in our home gym or at a local club was geared for fitness and health rather than toning and trimming for the attention of guys. It was important to her peace of mind. These periods might be weeks at a time where she'd dress as most mothers do wearing little or no makeup and barely doing anything with her hair. Though she didn't really show her age, she knew it was creeping in and she would get more tired, needing more time to rest. Forty wasn't old by most standards, but when you're so sexually active, it wears on you. Now approaching forty five, the various aches and pains were starting to add up.

She began thinking about my idea of adding another mother to the cougar den and wondered why she hadn't thought of it herself long ago. Hell, it would give her more time off. She'd seen Ashley at the gym in her workout clothes and at a few parties in evening wear and agreed with me that she was quite attractive. And yes, she could rock a bikini as well. A plan was forming in her mind as to how to approach Dan's mother as I had asked. There were a few phone calls to gauge the potential. She deliberately tried to get closer as a friend of the type that talked about personal experiences and intimate encounters. They'd go shopping and try on clothes together, then stop for a drink or two. Invariably, the conversation would turn to men and desires. As it progressed, Mom started to pull out bits of information that showed Ashley would be a prime candidate. Her husband, Dan's father was a bit of a cad and didn't really spend much time with her. It had taken the toll and Ashley confessed to Mom that she had taken on a few affairs, some with much younger men.

Without really being sure how it all came together, they got much closer to each other and Mom somehow let the pool story out during drinks at our house one evening. But Ashley had a surprise also and let on that at least one other neighborhood mother was doing the same types of things and that they knew some of what was happening at our house. Workouts at the local fitness club were taking on new meaning as these three forty-somethings shared more and more details. They also began working out at each other's homes and exploring wardrobes. Yes, this seemingly demure mother named Ashley also had a kinky, risque side stashed in her closets.

It had been a few months since my question and it was now taking form. Of course, during that time, we as a family had continued as we were, having poolside sessions with my friends and a few other double dates with my sister. We had all gotten so much closer, and we were bonded almost as one. Mom would go out of the house in the evening dressed in her best and we knew what was going to happen.

Saturday started off pretty normal with breakfast and some household chores. A little after noon, Mom called me and Carly in to the den. She started telling us about her time with Ashley and how things had progressed. Very bluntly and crudely she reminded me of how my friends called her an excellent cocksucker. That brought a chuckle from us all. But her next comment blew our minds.

'Now let me tell you from experience that my new friend Ashley is a masterful pussy licker. And she tastes wonderful too.'

Carly and I looked at each other stunned. Mom had very often talked about sex with men, but had never once mentioned anything about other women.

"Mom, you're Bi?" Carly asked in astonishment.

"Well, I'm not sure I'd put it that way, but yes, I've had some experiences I've never told either of you."

We were almost dying to find out what other things she hadn't told us, but she broke the session off saying she had a couple of things to take care of for later.

Looking directly at me she added, "I've worked it out with Ashley and Dan if you're still interested."

Of course I was.

A few hours later, I was in my room and Mom called me to the Den again. We talked for a few minutes and a scent came over me. A perfume I wasn't familiar with wafted through the air. A hand appeared on my left shoulder from behind, a very feminine hand with professionally done nails and a very large and prominent wedding ring. Another wrapped around my waist and then the unmistakable feel of two firm breasts pressed into my back as a pair of lips began to nibble my ear.

She stepped back and I turned around taking in this vision of a mature blonde woman with exquisite make up and hair, squeezed into a cocktail dress.

Mom chimed in, "Carl, I believe you know Ashley, Dan's mother."

Uh, yes, I sure did, but I'd never seen her like this. I looked at her for a moment, then stepped forward, took her into my arms and kissed her. It was only then that I noticed Dan was also in the room.

We all looked at each other and took in the situation as I held her as close as I could, not wanting to let this magnificent woman go for a second.

Dan wisecracked, "Hey Mom, I think he likes you!"

"You know Dan, I think you just might be right." she replied.

We moved to where we could all sit down, Ashley and I on a couch, my mom and Dan in chairs across from us, watching. She leaned back across my lap and we were making out like a couple of newlyweds as my hand groped her breast while her son watched with a massive smile. Her hemline had pulled up quite a bit, almost inviting my hand to her incredible legs. I accepted and caressed them with care slowly working under the hem. Home! No panties and only a wisp of pubic hair with a definite indication of wetness.

She and Dan stood up and I was thinking something was wrong hoping they weren't leaving. He moved behind her as she stood in front of me.

"Carl, do you remember the day out by the pool when your mom asked you to remove her bikini for us?" Dan asked.

Well, of course I did.

It was his mother's turn to speak, "Well now my son is going to return that act of consent and trust and remove my dress for you."

My mother was just sitting back grinning at all of this as we heard him lowering her zipper. He pulled the dress off her shoulders and let it fall to the floor. Here I was stunned again. She was even better than I had remembered from the neighborhood pool parties years back before all of this started. Simply amazing. The workouts had worked wonders. I sat back and admired the vision standing before me for a minute. A half bra cupped her breasts while showing her nipples. Thigh high stockings stopped at the top of her thighs. Her bare bushed was carefully trimmed.

"Dan darling, would you be so bold as to remove your mother's bra for your friend?"

Gratefully he did without hesitation before moving back to his chair.

"And now it's your turn" she said as she lifted my shirt off and lowered my pants running her hands where ever she wanted to, stopping to take a firm grip of my cock. She was in full on slut mom mode now and everybody knew it. Going to her knees, she went to work on me in full view of her son and my mother, holding nothing back at all.

She had me lay back on the couch, then turned her back to me as she faced the others and straddled me, toying with my cock with her hands, rubbing it against her.

"Danny, I'd like you to watch this, but I'll understand if you don't want to."

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He just smiled knowing how many times I'd watched him enter my mother.

"Mom, I wouldn't miss this for the world."

She raised up a bit and sank down on me, taking my cock fully inside her wet cunt. Though I couldn't see her face, based on the look on his, it was clear they were staring directly into each other's eyes as she worked herself up and down my shaft several times. She leaned back into me and my hands were able to grasp her wonderful breasts. It wasn't long before I erupted into her. She stood up and let everyone see it running down her leg as she wiped it with her finger, brought it to her mouth and licked it lewdly.

"Show's over son. Go on home now and I'll see you in the morning. Come back for breakfast if you want to, I'll still be here."

She took my hand and we headed for my bedroom.

The next morning saw all five of us around the breakfast table in frumpy clothes. Ashley was wearing one of my mom's robes.

Conversation was normal considering what had just happened. Really no mention of it. But plans were taking place for the next pool side cougar party. He hadn't really been sure even as late as yesterday afternoon, but after what he saw last night, Dan had come fully around to agreeing to the whole thing and was ready for the rest of the guys to meet her.

Since I was the one to suggest this, setting it all in motion and the first to have her, he wanted me to walk her out to the gang and introduce her. We started to work on the schedule as to when all six guys could be there and picked a day after a few phone calls.

They left together and we went about our normal daily lives for the next week or so. It was odd how all of this just fell casually into the background. Nobody really dwelled on it as it became a normal as a trip to the grocery store for us. We all saw each other during the week and aside from normal everyday greetings, nothing was said.

The next gathering day arrived and started out calm. Ashley showed up late in the morning and we could see she was a bit tense. Mom took her upstairs for a pep talk, or so they said. An hour layer she seemed a lot more calm... and aroused. Mom licked her lips as if to tell Carly and I what had happened in there.

The plan was to tell the guys Mom wasn't feeling well and couldn't be there today. They'd be disappointed at first and figure they would just start off as a pool party among the guys. Then I'd spring it on them that we had a special guest. None of us would know Mom would be upstairs watching it all from her office window.

The guys arrived and it started out as planned. They all jumped in the pool and played some other yard games, burning off energy from the week, bummed they weren't going to be getting their usual sex from an older woman. I went inside to get a few things. Ashley and Mom were fiddling around picking out a swimsuit. I reached in a pulled out a very tiny white one.

"Really?" Ashley asked.

"Really!" I replied, adding "You're only going to be wearing it for a short time before I take it off you leaving you naked in front of six guys half your age who are about to be doing all sorts of things with you."

"Oh, yes... well when you put it that way!"

Mom handed me a matching pair of white heels. I leaned down and put them on her feet.

"You should do this at home for a while. Get used to being fully naked wearing only heels. You'll be doing it quite a bit."

She strutted over to a full length mirror and admired herself, smiling coyly, running her hands over herself.

"Yes, I see."

"OK, lets get this on and make our entrance."

I slid the white panties up her legs and fit them snugly over her mound and cheeks. Then I fitted the skimpy, barely there bra top over her tits, taking more time that necessary to adjust it.

"Enjoying yourself?" she asked.

"Enjoying you" I replied.

She chuckled, took one last look in the mirror and sighed.

"OK, let's go. I'm as ready and I'll ever be."

Once we got to the back door, I took her hand and we walked out together.

The guys didn't miss the entry at all. Thinking no one would be there for the usual fun, some of them had already dropped their shorts. She had their attention now for sure and they rose to the occasion as we got to the pool hand in hand.

"Hey guys, I think most of you have met Dan's mother Ashley. Since my mom can't be with you today, Dan has graciously offered his mother for your pleasure today."

She stepped over to her son and gave him a motherly hug and kiss on the cheek.

"Can you all thank my son for letting me be here for you today?"

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A sheepish chorus of "Thank you Dan" followed.

She moved to put herself between me and her son, placing her arms around our waists and pulling us close.

"Now, it's only fair to tell you that Carl and I have already spent some time together and have become well acquainted. Isn't that right son?"

"Yeah guys, it sure is. They got along great too and even let me watch a bit before going to his room."

Another mass sigh emerged form the guys almost drooling by this time. In fact, a couple of their cocks were drooling precum, something she didn't miss.

"Mmmm, looks like a couple of you are more than ready for me."

Then she said something that made us aware of just how much my mother had shared with Dan's.

"Dan sweetie, which one of your friends would you like to see with your mother first?"

She was fitting the mold perfectly by taunting us all the same way my mom usually did.

He called a name. She looked at the guy, dropped her arms away from us and strutted to him, stopping with her breasts less than an inch from touching his chest.

"My son would like you to fuck me first. Are you OK with that? Would you like to fuck me?"

Well of course he said yes. She put her arms around his neck, pulled him close to her, mashing her chest into his and kissed him passionately. Kneeling in front of him she made a spectacle of handling his drooling cock and licking the head of it. She kissed it a few times and opened her mouth enough to place her lips over the head.

"OH, I'm sorry, I think I got some of my lipstick on your cock."

He did not object at all.

She moved back to her son and stood in front of him, facing the guys. He got the hint and unhooked and removed her bra, then slid her panties down her legs.

"Thank you darling" she said as she walked over to one of the loungers and laid on her back, opening her lags. She motioned to the one guy that had been selected and directed him to eat her cunt. Somehow she managed to look at her son while this was happening as if seeking his approval and consent. After a few minutes, she had him move up her magnificent body and nuzzle her tits.

Then she looked him square in the face and said simply, but bluntly, "Fuck me!"

It was almost more of a command than a request. He moved up a bit more, positioning his cock at her cunt. Working it around her opening, he pushed in a bit to get started, then worked slowly but steadily into her. She wasn't looking anywhere but into his eyes

as he pumped and pumped until he lost control and flooded her. They laid still for a moment caressing and convulsing before he pulled out, their combined juices clearly evident.

Without moving a bit, she looked at the guys and said "Next?"

She had told us earlier that she wasn't sure how it would all go and would just play it by ear. She promised to let one guy have her, making sure we all understood that she fully intended to do that much. But she wasn't sure how much farther she'd be willing to go on her first time. By the end of the afternoon however, all five of us had been in her at least once. Poor Dan was the one who had to sit it out this time.

The others left and we went back in the house. Ashley came to my room and Dan went to my mother's for the night. At breakfast we recounted the whole day and that was when my mom told us that she had watched it all.

This was also when the told us something we didn't know and hadn't anticipated. It seemed there were other sex starved mothers among the group of friends and at least two had expressed interest in taking part. Over the next few weeks, that's exactly what happened and now there were four mothers of the group of friends involved, doing exactly what the first two had done. The son of the featured guest always sat it out and watched his mother entertain the rest.

Dan and at least one of the other guys had said something about Carly joining us. I'd never seen Mom get so firm and direct. That was a flat and stringent no, not on any terms. She'd end the whole thing if it was ever mentioned again. They got the message, but I had to bring it up again later between the just the three of us to try and understand why she got so mad.

"Carl, it's just not what we normally do. We go out a lot together and have similar encounters, but we never share that. We double date, we're often nude together and having sex in the same room, but that's it."

Then she explained two exceptions.

"Only three men have ever had both of us. One was by accident in that we didn't know until we compared notes. The other was a special arrangement where we double dated a man and his son for a weekend on their yacht. I was the son's date and Carly was the father's date. Over the course of the weekend, some how it just all came together in a way that we were OK switching dates and by the time it was over it had happened a few times. There was one point where were side by side and the men pulled out and swapped mid stroke. After we talked later, Carly and I weren't comfortable with that and promised we'd never do it again."

"Now, Carly, I do have to let you in on something. I have someone who is very interested in fucking a mother and her daughter, but only one at a time. I've told him we won't participate together, and he's OK with that. I just haven't decided whether to accept or not, so I want you to think about it a bit and let me know how you feel about it."

"But Carl, I'll say it again, your pool friends are not welcome to Carly at all. She and I have talked and she's watched a few times, but aside from that first Homecoming Party she won't go for it. "

My sister chimed in, "Carl, it's more about connection for me. The younger guys I date are just that, dates. I may end up getting serious with one of them. And I'm not interested in any of your friends from the neighborhood around here that might want to go further. The older men are just fuck buddies. I meet them, we fuck, we go our separate ways, no strings."

"Mom, I'm don't know. It might be OK, but we'll talk more later."

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