Executive Mother Ch 01

While I was in high school my Mother had been working on her MBA. We had lived off of my father's alimony and my child support. Since he had loads of money and my Mom had a damn good divorce lawyer, we were quite comfortable.

Mother had me when she was only 17, so she was only 35 when she got her MBA. She was immediately hired by an unusual company, one that was all-female staffed. Everyone from the Shipping Dept to the CEO was female. Not a single man worked for this company in any position. I wasn't even sure they had a men's room in their entire building either.

After a year of working there, Mom got a huge promotion. She went from being one of the minion assistants to head of an entire department. Along with the position was a requirement to participate in executive events, training and get-aways. What was odd (to me) was that on many of these get-aways the exec's were required to bring along their 18+ year old sons. I had no idea what that was going to add to the gatherings but I agreed to go as it helped Mother make the big bucks. Most of these events took place at well to do resorts, so I thought I'd soak some rays, swim in the pool and maybe check out the other exec's. I'd always had a thing for older women anyway, I had a couple of professor's in college that were in my fantasies.

So the time eventually came for Mother and I to attend one of these gatherings. She explained how it was both a brain storming session as well as a paid R-and-R trip. As long as it had a pool and some older women, I was good to go!

So we packed our bags for a week long visit, headed to the airport and off we went to Jamaica. Once we landed, we saw the signs on the side of the vans with the names of mom's company. There were several other mother/son pairs there, many of the moms were certainly going to be fueling MY fantasies in the next several days. I couldn't wait to see some of them in their bathing suits as well. How little I knew then.

My first surprise was when we got to the resort. they had the name of it on there, "Hedonism II". I had read about this place on the internet and wondered why the CEO would want to bring mother/son groups to a place that emphasized nudity, public sex and debauchery?

My second surprise was when we entered our room. First of all, I had thought we'd have our own room for each of us. I thought, no big deal, save money with one room but have double beds. Only the thing was, there was only ONE bed for the two of us. When Mother and I walked in, we set our bags down and kinda looked at each other with a "WTF?" look on our faces. But, as Mother pointed out, we'd make the best of it and proceeded to unpack her bags. I watched out of the corner of my eye as she unpacked her underwear, bras and (finally!) her bathing suit. I hadn't noticed much difference in what I had seen in the laundry and what she had brought with her. I was kinda disappointed as I had hoped to see that Mom had worked up enough spirit to wear undergarments that were as sexy as she was.

We took turns taking a shower and changed clothes after the long flight and went down for the first mandatory meeting. As we entered, I saw more and more hot moms. My head was on a swivel checking them out. I noticed virtually every other son was doing the same thing. My mother attracted more than her share of looks, many of them lingering.

We went in and took our seats. There were perhaps 50 or so mother/son "couples" there I would guess. Not a single one of the moms were what I would rate below an "8", many were "9+". My fantasies were running rampant, as I'm sure the other sons' were as well.

Things got quiet when the CEO stepped up on the stage and walked to the podium. She was in her early 40's, built like a brick shithouse. She was close to six feet tall, with an athletes build. I guessed her to be a former volleyball or basketball player in college. She clearly kept up her workouts despite what I'm sure was a hectic schedule in running her business. Then she began her speech.

"For those whom have no met me, which are the sons here, my name is Cindy Moore. Welcome to our little gathering. I know some of you have attended these before but many of you are here for the first time. All of you were tightly screened before you were hired and even more checked before you were promoted to executives. All of you are good looking, all of you are single women. All of you have sons." As she said the last line, she got both a gleam in her eye and a smirk on her face.

"I began this company with the intention of giving women positions of power and wealth, free from the glass ceilings that sometimes exist in many other companies. Here we're free to do our jobs, coupled with a company that stresses a balance with family, specifically their sons. First on the agenda is the "meet-n-greet" at the pool. I have taken the liberty to have delivered to all of your rooms new bathing suits for each of you. These outfits are indeed mandatory for the pool party. I'll see everyone there in a bit."

With that, she turned and left. My mother and I turned to look at each other in surprise and wonderment. "Well, I guess we'd better go get changed for the party. I don't want to be late or the last ones there", Mother said. So off we went back to the room to see what Cindy Moore had delivered to our rooms.

We walked in the room and saw our new bathing suits laid out on the bed. Mother let out a small gasp and said, "She's GOT to be shitting me?!"

Mother's suit was something ordered from the Wicked Weasel. In short, the entire amount of materiel would barely make a Kleenex. My head began to swim with the thought of seeing my sexy mother in such an outfit! I'd seen her around the house in her underwear and such but she had her own bathroom so I never had gotten a chance to see her nude or even topless in all my years. Not that this hadn't slowed my fantasies about her in any way. She was easily one of the "9+" moms in attendance.

When I picked up my suit, it was my turn to gasp. It was basically nothing more than a woman's thong underwear. And a tiny one at that. Unless a guy had a 1" dick, it was either going to poke out the side or the top. Since I was in the 7" range when hard, I knew this was going to be a bad fit.

Mother grabbed her suit up and headed to the bathroom. She told me over her shoulder to change in the bedroom while she tried to somehow make hers fit. She closed the door as she went into the bathroom, leaving me once again with my imagination of her taking off all of her clothes.

I decided what the hell and quickly stripped down. After turning my suit around in my hands I thought there wasn't a better way of dealing with it other than just putting it on. So I slipped it up my legs, aligned the sting in the crack of my ass and attempted to stuff five pounds of genitals into a one pound bag. As I surmised, my ball sack and dick hung out no matter what I tried. Finally I left it alone and sat on the bed, waiting on Mother to come out.

After a moment, the bath door opened but she remained inside. "John, I'm coming out in a second but I wanted to warn you. This is NOT what I would have chosen to wear. I may as well be nude for all the coverage I've got." My mind began spinning with that announcement. Embarrassingly, my dick began to grow with the thought of seeing my mother's private areas for the very first time. Of course, it made my dick stick out of the thong I was wearing as well.

Finally Mother slowly strode out of the bathroom. All I could think was "WOW! Isn't she HOT!" She walked slowly up to me, almost timidly. This was NOT the serious, assertive woman with a MBA that I knew and loved. This was a shy, virginal bride on her wedding night it seemed. Her arms were locked to her sides, her head facing straight ahead, her eyes not focused on anything and a fine blush was creeping up her neck and face.

She walked to where I was sitting and stood only an inch or two in front of my knees. Her nipples looked hard enough to cut glass with, they were sticking out the material like a baseball bat put inside a grocery bag. My eyes wandered down her taut torso, looking at her crotch. I was surprised to see she had completely shaved her pubic hair. Mother had had only two or three dates in the last five or six years, so I knew she hadn't shaved for anyone in particular. I guessed she had done so in thinking she was going to be wearing a bathing suit, just perhaps not this specific one.

When I got to her crotch with my eyes, my first thought was her crotch band could've been covered with my thumb. It basically barely covered her clit, her labia and that was IT. My jaw hung open as I feasted my eyes on what was both a sexual beautiful specimen of a woman as well as the forbidden image that was my own mother. I was simply entranced with the sights and thoughts.

Finally, I saw her body relax and most of the tension go out of her. She even allowed herself a small giggle. "Well, I always wondered what I would look like in one of these things. I guess I don't look terribly bad based on your reaction", she said.

I looked up at her face when she said that, seeing her smile at me. Then I realized she was commenting on my now full fledged boner, sticking up like a flagpole from the top of the suit. It was then my turn to blush, further fueling her giggle into a loud laugh.

Mother stepped back a bit and grabbed my on the outside of my shoulders. "Stand up and let us look at each other. Maybe some of the embarrassment will rub off of us then." She then pulled me up to a standing position, my dick sticking up tight against my stomach. Her eyes were locked on it, with her tongue playing lightly against her lips.

"Well now, John. It seems as if you've grown into a fine specimen of a man. Lord knows there's nothing to hide with what you're wearing, much as what I have on. I don't know that it's a good idea to walk around here with that thing sticking up like that though. What do you think?", she laughed.

I replied, "Uhmmm, probably not. I, uhhhhhh, might need to do something. Take a cold shower maybe?"

Mother laughed even louder with that. "A cold shower? Seriously, John? Boys your age get boners when the wind blows. The only way to ensure it goes down at all is with an orgasm. How about we go that route?"

My blush had turned even deeper with that. My mother and I had never really discussed intimate sexual thoughts or feelings. One of us might comment on an actor that they were hot looking or something, but that was about it with us. Now my own mother was talking about MY orgasms like it was the weather!

Mother then pushed me back gently onto the bed. My dick still was rock hard, still sticking out of the suit. Mother stepped up between my legs, to the edge of the bed. She looked down at me, right into my eyes.

"John, I think it might be best for you if you simply masturbated. I doubt you'll last long and we can get down to the pool quicker."

All I could do was process what she just told me. MY mother wants ME to masturbate right here? In front of HER? Say WHAT? Meanwhile, I'd swear my dick got even harder with the thought of doing that very thing. It began to leak pre-cum out the tip, almost as if I were peeing. I knew right then she was right about one thing: I wasn't going to last long!

But even as all this ran thru my mind, I had another thought: maybe I could get HER to do something for ME?

"Mom, do you think you could do me a favor? Obviously since time is critical, can you help me along a bit?"

Mother looked me right in the eyes and asked, "What did you have in mind, John?"

Mustering ever ounce of bravery I had, I blurted out, "Can you show me your breasts?"

Both surprising me and pleasing me, she was reaching behind her back for her top string even before she laughed and said, "Sure, why not? It looks like we're going to be experiencing a lot of new things this week."

Mother untied her top string & flipped up her op off of her head. My eyes bugged wide open as her breasts came into view. They were what I would describe as perfect b-cups. Just a perfect mouthful! Now free of the materiel, her nipples seemed to grow even as my dick had. My hand snaked down to my dick, I began to lightly stroke it.

"No John, you can't do it properly with the suit on. Let's make things a bit better and easier for you." With that she bent over and grabbed the sides of my thong suit, tugging them down. I raised my ass off the bed enough for her to get them down to mid-thigh, where she left them. What she didn't do, though, was raise back up. She continued to lean over me, still looking me right in the eyes. He breasts dangled down, over my stomach. Mother placed both hands to either side of me, supporting herself on the bed.

"How's this, John? Is this enough to get you going, you think?" All I could do was nod, I was intoxicated with both the sights and the erotic moment. I grabbed my hard dick and began to stroke. It was then that Mother surprised me once again as her eyes left mine and she fixated on my dick. I took the opportunity to stare at her perfect breasts, wondering how her nipples would taste, what sounds she would make as I nibbled and licked them? I began to stroke my dick in earnest now.

Just as Mother had predicted, I didn't last long. What couldn't have been more than a moment or two and I felt my balls boiling. Mother continued her eye-lock on my dick. She again licked her lips, this time with more fervor and intensity than when she saw my dick for the first time.

I began to shout, "I'm going to cum!" With that, huge gobs began to shoot from my dick. Rope after rope shot from my dick, pooling on my stomach. Eventually, the eruptions ceased, my hand milking the last remnants from my balls and dick. My breath and heart rate felt like I had ran a marathon.

Mother raised up off of me, still topless. She walked into the bathroom and returned with a bath towel. "I'll clean you off. I decided we'd need a bigger towel instead of a hand towel" she giggled. She began to mop all of the semen off of me, quickly making it a complete job. She went off to the bathroom to deposit the now dirty towel when I saw her do something that amazed me again. She had a small dab of my cum on the back of her hand. Rather than wiping it off, she raised to her mouth and licked it clean! Holy shit! That was THE most erotic thing I think I had ever seen in my life!

As Mother came back out of the bathroom, she clapped her hands and said, "C'mon! Let's get dressed and get down to the pool. Pull that lame excuse of a suit back up and let's get going." She again had that smirk on her face that I had never seen before today.

I raised off of the bed, pulling back up my suit. Mother slipped her top back on, once again covering those perfectly looking b-cup breasts I had just jacked-off to. We slipped on out sandals and headed out, both of us self-conscience of how little our suits covered.

As we approached the pathway, we began seeing the other company mother/son couples. All were wearing some sort of variation of what Mother and I had on. This time I noticed that not only were the sons openly ogling the other women, the mothers were also checking out the other sons. Some were blatantly staring, not caring they were seen checking out men half their age.

I also noticed different attitudes among the other mother/son couples as well. Some were seemingly comfortable with the situation, even looping their arms with each other. Others were looking everywhere except at each other, almost as if they were forbidden to interact. This was despite the skimpy attire worn by both sexes, never mind the nice bodies on both sexes.

We eventually all arrived in the pool area, which apparently had been reserved for our group only. We all looked for chaises to sit on but noticed that there were way more people than places to sit. This resulted in the doubling up of some mothers & sons. Some sat side by side, some had sons standing next to the chaises with the mother sitting in them. However, a select few had the sons laying back in the chaises with their mothers lying in front of them, lying back against the chests of their own sons. Many of the latter had their sons arms wrapped around their moms, their mothers hands resting comfortably on their son's legs.

Once again Cindy Moore took the podium that was set up. "Welcome again. I see everyone found both their provided suits as well as their way to the pool area. It's nice to see how lovely you all look in them. And I do mean both sexes in how lovely you all look. We'll be setting up some snacks and drinks alongside shortly as well as some musical entertainment. This will be our original get-to-know-another phase. I encourage everyone to cast aside their inhibitions as well as their shyness and enjoy themselves. In case some of you aren't familiar with the rules at this resort, it's simple: there aren't any. As long as all parties are agreeing adults, they're free to act how they please, with whom they please. Many of you will be more comfortable mingling with the opposite sex of another couple, some of you will choose to seek out those of your own sex. Anything is allowed here as well as strongly encouraged.

"Allow me to introduce everyone to my own son, Jay. Jay, stand up so folks can see you, please." It was then some guy whom looked like he belonged on the cover of GQ stood up and waved to everyone. There was a noticeable titter among the mothers in the crowd as they gazed upon his model-like looks and physique. The moms in the back craned for a better look as he sat back down.

Again Cindy Moore spoke. "We'll be having some games around the pool. While we won't be giving such pedestrian prizes as coupons, we will be giving away nice ones such as all-expenses paid trips to the winners. Of course, these trips will all include the mother/son combos. So please, mingle among yourselves and enjoy the evening."

With that, she stepped off the podium and her son stood up as well. They didn't just link arms and walked off, no sir. They wrapped their arms around each other and pulled the other one tight to them. As I looked around the pool at the women, I saw some of the women were smiling, some were still in the "WTF?" look. I did notice that those whom were smiling were the ones whom were leaning back onto their son's bodies in the chaise lounges. Clearly these were the ones whom had been to these events before, I thought.

Mother announced, "I need a drink, I believe. John, let's get something from the bar and we can begin mingling." Since we were among the ones without a chaise, we ambled over to the bar. Mother surprised me by ordering a large drink in some sort of fake pineapple glass. I saw the female bartender pour about four or five different typed of rum in it and they were all long pours. I thought Mother was going to get hammered as she has little tolerance for alcohol.

After we got our drinks, we turned to face the crowd of her coworkers and their sons. Mother pulled me long by the hand up to a couple of them that she already knew. The women all introduced themselves and their sons to the guys as all of the women already knew each other. The sons were all ogling the other women while standing next to their moms. The moms were all doing the same to the others' sons, not even bothering to hide it when they checked out their crotches.

After a couple of minutes, the alcohol had its effect on the women. I had noticed none of the other guys were drinking, as neither was I. Perhaps we thought it would slow down our enjoyment of the scene? But it certainly turned the women into giggly, touchy things. As our conversations grew with each other, I had several of the moms pat me on my chest or arms while they talked. Even my own mom was doing it. I also noticed we had all moved in closer to each other, subconsciously. Eventually it got to where the moms were rubbing more than their hands on the other sons, they had gotten close enough mash their boobs into arms, chest and shoulders of the guys. All of the sons had certainly noticed their behavior as well as the hardening of the nipples that were poking out.