Charli the Poolside Cougar

It was almost getting mundane. Fun, enjoyable at the time, but little variation. I wanted something different, but with my Mom as more or less of the the head of the Cougar Den, I had to run it by her first. I had to work out how to make my case.

Yesterday afternoon's session had worn my mom out quite a bit and she was sleeping later than usual. Maybe have been because we went longer and the guys stayed later into the evening. That's what I needed to fix. Shorter sessions, but higher level quality. Or at least a different type of session.

She finally woke up and came down to the kitchen, looking rested, but weary and didn't appear ready to talk about anything. I gave her a quick Mom-kiss on her cheek and asked to let me know when she was feeling better, then went on to do other things.

As I was hanging out making some notes for work, she came into the room and made a similar comment. Maybe she was too old for this and it needed to slow down some.

"Well, Mom, when you have five or six guys going at you at the same time, it's got to be hard to keep up, even for a younger woman. I mean that stuff's got to be pretty intense for you."

"You know, I used to be able to orgasm three or four times, take a quick nap and be ready for more. But I don't remember them being so intense back then."

"I think the guys are getting used to how to make it happen for you and they're pushing it a bit too hard. Almost like a competition between them to see who can make you cum hardest."

"Yeah, maybe. I still like it well enough and don't want to stop."

"No Mom, I don't want it to stop either. I love every bit of it. But maybe we can change some things to break up the pattern."

"What do you mean?"

"Well, I've been thinking about turning the tables a bit. Maybe instead of one mom and five guys, maybe one guy and five moms."

Her head tilted towards me. "How would that work?"

"You remember my first time with Ashley, when she was all dolled up?"

"Yeah, I set that all up and helped her pick an outfit."

"Well, it was a great one and helped set the mood. So what if we expand that?"

"Go on."

"Mom, think about a type of women's club similar to the celebrity event we went to where the sons presented their mothers. That's sort of what we do here, but on a different scale. Now think about some of the women's clubs around here that just get together for tea, or cards, or bingo. "

"God those are boring. I went to a couple long ago and left early."

"Yeah, I imagine they are, but do they have to be? What if it was in the late afternoon or early evening and all the women dressed to the hilt and one of them brought her son. Only one."

"This might be about to get interesting."

"Mom, think about you, Ashley and the rest all dressed up. But just one of us attends for the others to play with. Some could even stay dressed if they want to sit out the evening. They could be a lot of the guy playing with the women. Maybe some under skirt action as he fondles her or licks her while the rest go on with their chatter. He's doing all the work rather than the one lady being pounded all afternoon."

"Carl, You may have struck gold here."

"I mean one of more could still go down on him. But maybe only one gets fucked while the others watch. Then maybe he goes home with her, or another, or not at all."

"Shit Carl, I have to go make some phone calls and see how the others feel. We're all getting older and if we can have the guys do the work, wow."

And she was gone to her office.

But I had more on my mind. Now it was off to see my sister and present another perverted idea.

I tapped on her door and opened it when she replied. She was laying on her bed naked, reading something.

"Hey little brother, what's up."

We talked about the pool, stuff and she admitted she'd like to play, but not under the current set up. We figured out that she wanted to be the center of attention at a party like Mom usually was.

"How many of your girlfriends have brothers?"

"Most of them I guess."

"So, how would a brother and sister thing work instead of moms and sons? What could happen?"

"I'm not sure."

"What about a bunch of the girls get together for an old fashioned sorority type sleep over? They do all the things that would normally happen, but one of them brings a brother that has to stay nude the whole time?"

"Could be damn interesting."

"Yeah, it might. I mean, you've watched me with girls a few times. Maybe you could watch me with several at a time. Doing little things like licking them or massaging them. Maybe it would be another brother each time and you could play with them. I like watching a guy fuck my sister like on our double date nights."

"Pervert!"

I didn't really expect this one to take off, but I just wanted to throw it out there. I suggested she think about it and I left her alone to do whatever.

A few days later Mom came into my room and sat on the edge of my bed.

"They LOVE it!!!. They can't wait to get one set up. And one more thing. The last two mothers of the six guys have decided to join in also. They don't want to do the the parties with all the guys, but they're willing to do this."

"Do they know what's going to happen? That they'll probably have sex as well?"

"Of course, that's the whole point. They've wanted to get into the other parties, but aren't ready for so many guys all at once. With just one guy, they jumped at it."

"OK, so when do you think?"

"They'll all be here Friday at 4. Make sure you're here. All six of us insisted you be the first guest."

What the hell did I get myself into?

Friday got here faster than expected. By two, the patio was set up for an afternoon tea, drinks and food ready. By three Mom was gone into her room to get ready. I stayed in casual clothes at first until I had a chance to go over some things, but would change later. At four they began to arrive.

There were only two of them, the two that lived farther away had to drive. I could see the others walking down the street from their homes. I greeted these two with casual hugs and showed them to the outdoor sitting area, telling them to get comfortable. By then the others had arrived, including the two who had never been involved. They were wearing walking shoes and carrying their dress shoes. I gave them a minute to change, they led them in with the others.

I poured some drinks and waited for Mom to appear.

They were all fantastic. They were all in slinky, frilly summer dresses. Some were very short, some knee length and two were almost floor length. Big floppy hats and summery sandals completed the Stepford Wives look.

Me? Well, I had on a smile. Nothing else. None of them had said at anything at all, but I noticed them watching my cock bounce as I moved around.

Mom's heels on the tile floor announced her arrival and shes didn't disappoint either in a flowery almost see through dress that fell mid thigh.

Lots of greeting and small talk at first, admiring each other's choices.

"Four of you wonderful ladies have participated in many of our events out by the pool. They know how grueling it can get at times servicing so many young guys at once. These evening events will change the entire pace and scope. Even if you're here, you do not have to participate in any sexual, or even sensual action of you choose not to. You are more than welcome to just sit back and watch, but you should let that wish be known so it can be respected. The entire atmosphere will be more relaxed and casual."

And that was that. As I made the rounds among them, their hands were very busy. Many just felt my balls or stroked my cock openly while they talked with the others. Some hugged me close for a deep, intimate kiss. I'd run my hand along their back and under their dresses. One asked me to sit on the floor in front of her and watch as she raised her dress and ran her fingers over herself. She inserted finger into her cunt, then withdrew it and ran placed it in my mouth for me to taste her.

Brooke was one of the new ones. She's was a bot shorter and more petite with a face that was just super cute. A real doll, but what got me most was the short black hair done in a sort of Marlo Thomas 'That Girl!' flip. She slid forward on her chair as far as she could, raised her dress to her waist and opened her legs. She took a bottle honey that I'd set out for the tea and biscuits and dribbled some over her mound.

"Oh dear, I seemed to have spilled some honey on myself. Carl, might I trouble you to help me clean it up?"

My tongue went to work and I made damn sure not to miss a spot.

Bella then called me in front of her as she went to work on my cock, licking and kissing her way along it. My first load of the evening went down her throat. Not a drop spilled out of her mouth.

As I stood up, Tawny, the other had never been here before walked up to me, took me in her arms and began one of the deepest and most intimate kisses I'd ever had. Just wildly intense was the only way to describe it. My hands explored her back down to her cheeks. Hers was one of the short dresses, so I was under her panties in no time rubbing her bare ass. She turned around and ground her backside into me grinding to the music. This let one of my hands explore her tits while the other lifted the front of her dress and get back to her panties. This time it just so happened we were standing directly in front of my mother, who now had a ring side seat of my fingers working this lady's lower lips. She broke away pulled a small bow at her side that let her wrap style dress fall open. A quick move and it fell off her shoulders. Hooking her fingers into the sides of her lace panties dropped them to the ground almost as fast and sauterned seductively to a spot where she got down on all fours inviting me to take her from behind. As I mounted her and began to thrust I could swear she growled, just like a cougar.

We all took a break as I refreshed their drinks and the snack trays. I noticed a couple of them dancing together in a rather intimate way, one of them being my mother who was not shy about kissing her dance partner.

The lady who had me lick honey off her cunt was back seeking more. Her eyes sort of told me what she wanted. Mom had broken off the dance and was standing at one of the tables getting a snack. Brooke led me to my mother's side, her hand was squeezing my cock as she spoke.

"Charli, I've never done this kind of thing before. Would you mind terribly if I had sex here with your son over there on the bench?"

"Honey, you don't have to ask that of me. That's why we're all here."

"I know, but it's who I am. I need to hear you say the words."

"OK Brooke, you can let my son fuck you in front of all of us while we watch."

I could tell the blunt language shocked her, but it also seemed to energize her at the same time.

She turned around so I could remove her dress. She laid back on the furniture and lifted her hips to pull her the wisp of lace that were her panties off.

By eight, the sun was setting and we decided to call it a day. Another successful day that was repeated for each of the sons in the coming weeks.