Executive Mother Ch. 01

It was then that I felt a hand at the top of my ass crack, palm flat against my back. I was ok with the touching, but I was worried about springing another hard-on in public. As the conversation flowed, I turned to look to see who it was with their hand on my ass. Much to my amazement, it turned out to be my own MOTHER! When I looked into her eyes, she gave me a bawdy wink and a smirk. Then she squeezed my ass some.

Mother replaced her now empty glass with a fresh one from a waitress walking around with refills. The entire time her hand never once left my ass. Once she took a healthy swig from her drink, she did something I had never had done to me before and certainly never thought of her doing. She turned her fingers to face down and them damned if she didn't just slowly slide her hand down the crack of my ass, her middle finger burrowed deeply into my crack!

Any pretensions of not growing a hard-on had by now been thrown out the window. The lower Mother's hand and finger went down my ass, the faster my dick grew. Since she was shorter than me, it actually made it easier for her to reach what seemed to be her goal: my asshole. Since it was quite warm there, coupled with the eroticism of the atmosphere, I was sweating a good bit. This only allowed it to lube her finger in my ass crack. When she reached my asshole, she simply allowed it to rest the fingertip on my sphincter. She then began a light, circling motion on it.

Holy shit, was I getting hard! Neither my Mother's actions nor my reactions had gone unnoticed by the other moms. Several of the women simply stared at my dick, now sticking up out of my suit top. The sons were noticing the movement of Mother's arm, probably guessing what was going on based on where her hand seemed to be from the angle they had. Things were heating up and I don't mean the weather!

Then, of all things, Cindy Moore came back on the PA. "Attention, everyone! We have our first contest! There will be a Water Horse battle in the pool. All pairs must be male/female, female on top of course. (This caused tittering from the crowd.) The prize is two weeks paid vacation in Hawaii at the company condo. As an added incentive, I will add two more weeks to it if the female is nude! All contestants have 30 seconds to enter the pool!"

Mother continued to lightly rub my sphincter with her fingertip. "What say, John? Shall we enter?" As soon as she said "enter", she slid her finger INTO my ass! I had never had a girlfriend do this to me before but had often played with things in my own ass. All that paled when compared to having one's own mother with her finger in one's own ass, believe me!

All I could do was manage to squeak out a "Sure, let's do it." She then slid her finger out of my ass and sat her drink down on a nearby table. She then untied her suit and dropped it on the chaise as well. She stood in front of me as nude as nude could be! Wow, was she HOT!

She grabbed me by the hand and pulled me to the pool. there were several others already in, all the mothers nude as well I noticed. I guess four weeks in Hawaii will make one do some goofy things?

Mother pulled me into the pool, somewhere in the 5 feet depth section. She quickly spun around to latch onto my back, her arms around my neck. "John, you need to duck under so I can get on your back."

I took a breath and went to a squatting position under water. Mother climbed up on my shoulders, nestling her pussy right up against my neck. As I rose up, she tucked her shapely legs behind my arms, further causing her pussy to rub against my neck. My dick seemed to add another inch I never thought I had.

I looked around at the other couples in the pool. All of the mothers had used their sons as the bottom support except one. This one had latched onto Cindy Moore's son, Jay as her support. All of the moms were completely nude except for one other.

"Ready? Set! Go!" shouted Cindy Moore. All the couples engaged to much shouting and laughing from those on the sides of the pool. I even heard a few bets being shouted as well. Mother and I went to the closest couple and quickly pulled the woman off of her son as he wasn't the most muscular of builds. We turned to the next one, the woman whom kept her suit on.

Her top lasted about one second as Mother grabbed it and ripped it right off. Since it had little materiel anyway, it didn't take much effort. Mother was able to drop this woman as well as the other woman seemed to be more worried about covering her tits than pulling Mother off of me. The entire time of all this, Mother was grinding her pussy against my neck like there was no tomorrow. Not that this bothered me in any way, of course.

Then it was down to the woman with Jay, the CEO's son, and us. We closed to grapple and pushed, pulled and tugged. All we managed was to exhaust each other. We seemed to be evenly matched. We finally both just latched onto the other and all four of us fell below the water surface.

I knew the water was over Mother's head, so I quickly stood and reached for Mother in order to get her head above water. She was now in front of me and as I pulled her back to me, my dick nestled right into her ass crack. Not only did she not move away, she wiggled her ass against my hard-on! My hands moved up to support those perfect b-cups I had been longing to touch. Not only did she sigh loudly when I pinched her nipples, she placed her hands on top of mine, pulling them tighter against her tits.

People cheered on poolside and Cindy Moore came back on the PA. "Looks like we had a tie. How about we split the time into two weeks for each couple? Sound fair?" Mother gave a "thumbs-up" and the other woman nodded. I noticed the other woman was supported by Jay but instead, she was facing him with her arms around his neck and her legs wrapped around his waist. Since it was pool water, it was clear enough to see exactly how she was.

As conversation picked back up around the pool, Jay and the other woman began to heat things up. They began to passionately kiss each other, all the while the woman was rubbing her body up and down against his. There was no question they were turned on and getting hotter by the second. They had the same effect on Mother an I as well.

Jay and the other woman (we later learned her name was Claire) we only a couple of feet from Mother and I. We were close enough to hear Claire clearly tell Jay to "fuck me and fuck me NOW!" Once Mother heard those words, she ground her perfect ass against my dick like there was no tomorrow.

Claire had dropped one hand down into the water, grasping Jay's dick and guiding it into her. Once it was in her, she began to ride him like a bronco rider on a wild horse. Once Claire's movements and moans became more intense, Mother moved one of my hands from her nipple down to her pussy.

I took the opportunity to step closer to Claire and Jay, both still fucking in the water like rabbits on speed. Mother now took my hand and rubbed it against her clit, using me as a means of pleasure. She timed my hand movements going up and down with Claire's up and down movements. Both women were moaning loudly in pleasure.

People around the pool had become quieter, watching intensely at the performance before them. Many of the women were wrapped in the arms of their sons, a few had chosen the sons of other women. All seemed to be in the motions of some sort of foreplay, rubbing, probing or plain old dry humping.

Claire then began to announce her impending orgasm and moaned even louder. Finally she began to scream like her hair was on fire. Mother intensified my rubbing on her clit, screaming coming from her as well. As Claire's screaming reached a climax, so did she. Mother was right there with her, screaming her orgasm too. Jay wrapped Claire tightly as he erupted with his own.

After a few minutes of cuddling, stroking and rubbing, we four began our way to the steps out of the pool. As Jay and Claire exited, they were met with mild applause. Jay just grinned while Claire smiled awkwardly. I think she just realized she just had public sex in front of her son. Her son handed her her bathing suit as she exited the pool, standing there awkwardly, unsure of what to do. Mother and I exited the pool as well, her in a fine grace, me with a hard dick sticking up out of my suit.

Then Cindy Moore came strolling up to all four of us. "Thank you all for the nice competition as well as the show. Claire, won't you introduce me to your son?" Claire did the introductions and Cindy seemed to have a relaxing effect of the guy. She touched him on the arm and chest as she talked to him, making him feel like one of the gang.

Then Cindy turned to Mother and said, "Jane, how about introducing me to your son?" Mother did the same and Cindy touched me just as she did Claire's son while talking to me. I noticed she had held Claire's sons' hand the entire time she spoke and touched me. He stood there with a deer in the headlights look. I stood there with my dick peeking out of my suit.

Apparently Cindy noticed as well. "Jane, how about you and John visiting with me for a bit while Jay and Claire grab a bite and something to drink?" Cindy still had Claire's sons' hand in hers the whole time. Well, when your CEO suggests something, one usually agrees.

"Sure thing", said Mom. Cindy had to notice Mother's nipples sticking out like bullets. While I had rubbed her to an orgasm, it was clear there were plenty more waiting in that sexy body of hers. "I do need to pee first though. Those drinks need to be recycled."

"I have just the thing", said Cindy. "Come with me. Stan, you're coming with us." Stan was, I learned then, was Claire's son. So we all four ambled down to a semi-private cabana tent that Cindy had allotted herself as a CEO privilege. There were two chaise lounges inside, along with a private bar.

"Jane, you and John are clearly comfortable with each other. You two take that chaise and Stan and I will share the other one." As Mother and I made our way onto the chaise, I only then noticed she was still completely nude. She never put her suit back on! Stan was sneaking peeks at her well but it was difficult as Cindy was giving him attention.

I laid back on the chaise and Mother got in front of me and laid back against me. "Cindy, I really DO need to pee!", said Mother.

"What a coincidence, I need to as well. How about we have some fun with the boys while we do it, ok?"

My ears perked up as this was also one of my fantasies, having a woman pee with, around or on me. Was this finally going to come to fruition? With my own Mother doing the honors?????

Cindy by now had gotten Stan to lie down on the chaise, lowering the chair so it was completely flat. She came over and helped get our chair in the same position and went back to Stan. Turning to us, she said, "Jane, I find it's extremely fun to play with young men, teaching them new things. Not to mention teaching them that older women are to be desired, obeyed and pleased. How about I urge you to follow what I do?"

Mother only nodded her head, watching Cindy, wondering what was next.

Cindy then hopped up on Stan's lap, allowing her legs to dangle off the sides of the chair. She was straddling him, for all intents and purposes. By now, Stan too had managed to grow himself into a hard-on with all the excitement and contact. His dick had popped out of the side of his suit, not escaping Cindy's notice as she gently rubbed the head of it with her fingertips.

"Jane, your turn."

Mother raised up and straddled me just as Cindy straddled Stan. I looked down at her beautiful ass, placing my hands on her hips to help balance her so as to not fall. Mother then looked over at Cindy after she got settled. I noticed she positioned herself with my dick laying right in the crack of her pussy. I thought I could detect a slight rocking motion as well.

"Ready?", said Cindy. "Stan, honey, just relax. I promise you will enjoy it and you will be rewarded for it as well. Jane, let it rip whenever you're ready. Piss on your son."

Whoa! My fantasy WAS going to come true! Mother gave a bit of snuggle of her pussy against my hard-on, leaned forward just a bit and then gave a sigh. The next thing I knew was a super warm feeling spreading all over my crotch. Mother had gone from a gentle rocking to a noticeable one. I figured she was rubbing her clit against my hard-on.

Cindy and Stan watched in rapt attention. Stan's eyes were as big as saucers, certainly this was sensory overload for him. Cindy kept her eyes on Mother's pussy and the puddle forming directly under the chair.

Mother kept up her rocking motion, leaning forward just a bit more to get stronger pressure on her clit. when she did that, I was able to see her asshole for the first time! Thinking turnabout was fair play, I took my thumb and placed it on her sphincter and slowly but firmly pressed against it. After a few seconds, the tip of it popped in. As soon as it did, Mother gave load moan, announcing her second orgasm of the day.

As Mother recovered, I slowly pulled my thumb out of her ass. I couldn't wait for the opportunity to slide my tongue there, or even my dick!

"Jane, John. Watch!" said Cindy. She pulled aside her skimpy bottoms and placed her pussy right on Stan's dick, just as Mother had mine. Cindy didn't rock, however. All she did was piss all over Stan's dick and balls. Stan grabbed Cindy's hips and ground his dick against her pussy as hard as he could, moaning loudly as well.

Finally Cindy was empty. She stood up and quickly shed her bathing suit, dropping it where she stood.

"I just realized something. Neither Stan nor John have come yet. Both of their mom's have, as has my son. Seems like we should even the score a bit, yes?" Cindy said.

With that, Cindy grabbed Stan's skimpy suit and yanked it off of his ass, down and off of his legs, leaving him nude with a hard-on. Mother stood and turned to me, eyes twinkling as she too reached for my suit. I again raised my ass to help her get my suit down, only this time taking it completely off.

"Jane, mind if I have both of them? I do love a threeway" said Cindy.

Mother just shrugged her shoulders, and stuck out her hand, helping me up off the chaise. Cindy moved around to the bottom of hers, spreading Stan's legs to further expose his crotch. She crawled up on her hands and knees until her face was directly above Stan's dick. She spread her legs as far as they would go but still be on the chaise pad.

"John, feel free to enter me anytime. I'm going to give Stan here the blowjob of a lifetime."

Mother moved out of the way as I lined up behind Cindy. Like Mother, she too had shaved her pussy. I could see the wetness glistening off of her pussy lips despite her never being in the pool, so I knew it was excitement that and not water. I stepped closer, allowing my dick to slide up her ass crack, eliciting a moan from Cindy as well as an ass shake against it.

I moved close enough to rest my dick against her pussy entrance, held her hips and sank my dick into her wonderfully hot, tight pussy. Cindy had already began to suck Stan's dick, her head bobbing up and down. Stan had his eyes rolled back into his head, moaning with intense pleasure.

Not to be left out, Mother came and stood next to me. She again took her hand and slid it down the crack of my ass. Again, her fingertip found my sphincter, rubbing it a bit more forcefully this time. I lost myself in the feelings of pleasure and excitement, knowing my own mother was not only watching me fuck her CEO, she was playing with my ass while I did it!

Of course, with all this excitement I knew I wouldn't last long. Mother must've sensed when I was getting close and she had another trick to play.

"Cindy! Slide your finger up Stan's ass while I do the same to John", said Mother. Mother leaned over my shoulder to watch as Cindy did take her middle finger and burrowed it under Stan's ball sack. Stan helped by raising his ass up off the chaise pad and spread his legs even wider.

As soon as Mother saw Cindy's middle finger enter Stan's ass all the way to the hilt, she then pushed hers into my own. My knees buckled with the intensity of pleasure as Mother rotated her finger around inside my ass. I moaned loudly every time Mother rubbed against my prostate, giving her a hint of where to keep rubbing.

I too leaned over Cindy's should, watching her work her finger in and out of Stan's ass like a piston. I knew neither of us was going to last much longer, especially me. With a roar, I announced I was going to cum. Mother responded by driving her finger deep enough in my ass that I thought she'd reach my belly button and just held it there.

I shot even more gobs of cum that I had that morning, jacking off to Mother's tits. Stan too was shooting into Cindy's mouth, setting her off on her own orgasm. She was getting hosed on both ends and had her finger in a young man's ass. She had to have been happy.

As both my and Stan's spurts slowed and ended, Mother and Cindy slowly withdrew their fingers from our asses with excruciating slowness. The post orgasmic sensitivity I had only multiplied the sensation of Mother's finger leaving my ass. I rubbed my groin against Cindy's pussy, wanting her to know how much this moment had meant to me.

Finally, I pulled out of Cindy and stood up, cum and pussy juice dripping off of my dick. Mother reached around and gently rubbed the length of my dick, sending shivers up and down my body.

Cindy slowly licked Stan's dick clean of all cum, humming a soft tune while doing so. I backed up a bit, giving Cindy room to stand up. As I did so, Mother got under my arm, snuggling in tight against me, wrapping both of her arms around me. She gently nipped my nipple with her teeth.

End of Part 1.