The Mother and Son Club

The Mother and Son Club

By Stephanie Gilbert

Copyright 2021 Stephanie Gilbert

All characters in this story are totally fictional and over the age of eighteen

"What college did you go to?" the man asked when he ordered his next drink.

He was well-dressed, and I noticed him and his partner, a woman I guessed to be a little older than him, the second they walked into the bar. It was a quiet night, and having worked here for years to help Mom pay rent, I knew that these two were new to the area. I liked them immediately and was glad it wasn't busy. We struck up a conversation about trading when I found out that he did it for a living. I was blown away by his knowledge, but I had formulated a new strategy and made a decent amount of change over the past year with Bitcoin.

"Google Tec," I answered, being a bit of a smartass.

"You learned all that off the internet?"

"I mined a bit of Bitcoin then lost most of it day trading like a blind man. I decided I needed to work out how to do it properly. So, I spend about an hour each night after I get home learning what I can. It's really so my mom and I can live more comfortably. I'm a bit of a 'mommy's boy', or so I've been told," I said with a nervous chuckle, serving them another round.

"My name is Bernie Noble, and this is Loise. I would love to talk to you and your mom about trying out this theory of yours and doing it on a larger scale than your few coins. But we will have to come up with a business plan to go before the board," Bernie said, surprising me.

"I'm Troy," I moved to shake his hand. "I'm just amazed that you are even interested, because this is only a very new asset class," I said, really blown away, but realizing this could just be the alcohol talking.

"Here is my card. Ring me tomorrow, but not too early. I may be late getting up after drinking and talking to you for half the night. Loise, let's go back to the hotel," Bernie said and kissed her as they made their way out of the door.

I put the card safely in my wallet, even though I was skeptical. Hopefully Bernie would remember talking to me in the morning. When I got home after midnight, Mom was still awake and made me a snack before bed. I sat watching her walk around the kitchen in her old and very thin nighty. I don't think she realized that I could make out every curve of her body, but I was mesmerized by her breasts swaying unrestrained under the thin cloth. I shook my head, trying to get the unholy thoughts to go away.

"Hi Bernie, it's Troy from last night. You said to ring; I hope it's not too early?" I asked hoping I wasn't making a fool of myself.

"Hi Troy. I rarely give out my card like that, and yes, I was hoping you would call. You already passed my litmus test by ringing when you said you would. We are in town for another two days. When can we have lunch or dinner with you and your mom?" Bernie asked, relieving some of my anxiety.

"Either night," I answered, so happy he remembered our conversation, and I was looking forward to picking his brain over dinner.

"OK, tonight it is. I will send a car for you at seven. It's OK to dress casually. We are in a private dining room, so text me your address," Bernie said, making decisions quickly and decisively; I liked that.

I sent a message to Mom, and she panicked. I think she thought Bernie was joking with me, and I was half on her side. Mom got off a little early and put on some makeup and did her hair. She then dressed in her best dress; it was a black number that only came a few inches below the bottom of her ass. She came out of her room just as the car beeped his horn outside.

"You look stunning, Mom," I said, and I was not lying, not even a bit.

She smiled and took my hand as we made our way to the car. Mom was trying to be lady-like getting in, but her short dress rode up as she had one foot in the car and the other out. I was holding the door for her and got an eyeful of panties. I should have looked away, but her head was inside the car so she couldn't see me looking. And it was such a lovely sight.

When we got to the restaurant, we were guided back to a private room and found Bernie and Loise waiting for us. Bernie introduced Loise and himself to Mom, and I did the same.

"This is my mom, Jenelle. She is responsible for raising me," I said proudly as I'd always been so impressed by my single mom doing it all by herself.

"Hello Jenelle. I'm Bernie and my better half Loise," He gestured toward the petite brunette. "Please, have a seat," Bernie pulled out a chair for Mom.

"Hi Jenelle. I thought Bernie passed the word that this was casual tonight?" Loise said with a smile.

"Sorry, I only have the one going out dress; it was either this or torn jeans and a t-shirt," Mom said, looking a little embarrassed.

"Well, you look beautiful, doesn't she, Troy? I can't believe how young she looks!" Loise said, putting me on the spot.

"Yes, she definitely does," I replied without hesitation. "And well, that's because she is young. She was a teenager when she had me," I looked at Mom's breasts bouncing as she laughed, then I looked back to Loise to find her staring right at me.

Loise just smiled and called over the waiter to take the orders. I was a little worried as the menu didn't have prices listed, but I made a mental list of the highest prices I could think of. We were racking up quite a bill.

"I'm picking up the tab Troy, so order whatever you like," Bernie said when he saw my worried look.

As we sat around after dessert, Bernie put his arm around Loise and started playing with her hair. Mom was giggling at whatever Loise and her were discussing. Bernie straightened up, and his hand disappeared under the table as we continued our conversation. Mom didn't seem to notice, but years of seeing couples do things at the bar, I had a sixth sense about it.

"OK, Troy and Jenelle, we need to get serious here. I have a proposition for you both. I want to try out Troy's theory on a larger scale, and I need someone to run it, acquire the Crypto and secure it, so it doesn't disappear on us. We will pay you a good salary with food and accommodation, and if things work out the way I hope they will, you could be offered a place within the group," Bernie said. I was waiting for him to smile and give the joke away, but he kept a straight face.

"What's the catch?" I asked, knowing this was too good to be true.

"There are a few catches, but the first is this." Bernie pulled out two sets of paperwork and handed it to Mom and me. "This is a confidentiality agreement that you both must sign to know any more about our group."

"What is this to do with me?" Mom said, confused.

"Troy will be working long hours and will need someone to keep house for him and tend to his needs. Also, I think you might find it difficult without Troy's income to help with the bills. So, it would just make sense for you to come along," Loise said, smiling at Mom, then me.

"Read the agreements and if you sign, I will continue explaining," Bernie said as he continued playing with Loise under the table.

I read the paperwork, and it didn't look too worrying. I looked over to Mom, who just nodded, and we both signed and pushed the paperwork back.

"Before I start, the people in the group have the resources to prosecute you if you break the agreement you just signed. Are we clear?" Bernie waited for our response, and we both nodded.

"OK, you will need a passport, and we will arrange for your furniture to be put in storage. You won't need a lot of clothes. Oh, that's one of the catches, the Island is owned by the group and is close to the equator, so clothes are optional. I will need your full attention once we get there to set up the accounts and do the buying of the Bitcoin so that our money doesn't push the market up artificially," Bernie said, throwing in the nudity like it was everyday conversation.

"So, we will have to be naked?" Mom asked, her voice going up an octave.

"Clothes are

optional

. I'm saying that because you are going to see couples naked on the island, but you can keep yours on if you like," Loise said simply, and Mom just stared at her with wide eyes.

"The housing is quite lovely, and a cleaner from a nearby island will come in every few days. All you'll have to do is cook your meals or arrange to pick something up from the restaurants. The Island is convenient because we make our own laws and don't have to pay taxes on our investments, other than what is due in the country they are produced, if any. As for Bitcoin, there shouldn't be any, because it isn't a country's currency that we are trading," Bernie said, looking at me.

"Where is this island, and how do I get off if I decide I've had enough?" I asked, wondering if I would have to swim for it if my theory didn't work out.

"The Island is off the coast of Thailand, and you have a return ticket any time you like. I'm not holding you responsible for any losses from the trading. We know it is experimental and have more than enough to cover any losses for the next few years while we fine-tune your trading theory," Bernie said. He must have read my worried face.

"What's the worst that can happen? We get to spend a winter in a tropical paradise soaking up the sun," Mom said, looking at me brightly.

My father took off soon after I was born. Hell, he was only seventeen and probably scared out of his mind. Mom's parents had kicked her out soon after. This was the first good thing to come her way in a very long time, and I couldn't blame her for being keen.

"I can't turn my back on the chance to try out my ideas, and I'm willing to put my money where my mouth is. Any trade, I will put all my coins on the line," I said, hoping that Burnie would trust me.

"Then let's have a drink to celebrate our new venture together!" Bernie said, holding up a fresh glass of Dom Pérignon 2008 champagne that the waiter brought to our table.

Bernie and I left the rest of the champagne to the girls, and ordered Mortlach bourbon for us. Although I had never ordered a bottle from the pub I worked in, I knew how much it was and jumped at the chance to try it out. I was definitely not disappointed. I knew this was some sort of pissing competition for Bernie, but I wasn't playing. I didn't have the funds even to start, the bottle of bourbon alone would empty my savings account.

"Just enjoy the drinks. I'm not trying to show you up; I'm enjoying seeing your reactions to the things I'm showing you. When you get to my stage in life, it sometimes takes fresh eyes to let you know what you have achieved. It is difficult to get a thrill out of life after you have had a lot of success. I have seen a friend bet a million dollars on a 20 to 1 outsider in a horse race just for the thrill of the bet, and it ended up losing, and it was only by a nose," Bernie said, sipping his bourbon with one hand still under the table.

"I will try to relax and just enjoy the company," I said, noticing that Loise reacted to Bernie's touch a little.

The night finished with Bernie insisting on his driver taking us home, as we were quite plastered. I had Mom slumped on my shoulder and snuggling into my side. I helped her inside, and when I got her to the couch, she flopped down on it and was out like a light. I couldn't help looking as her short skirt was almost to her waist. If I had been sober, I would have looked away in fear that Mom would open her eyes and catch me, but I was drunk enough to stand between her splayed legs and stare at her pussy covered with only thin lace panties.

Just then, Mom's hand moved, and I shifted sideways to be less evident that I was staring. She scratched her pussy, pushing some of her panties into her cleft. Her hand then returned to her thigh, and now I had an even better view, with one of her outer lips fully uncovered. It was cleanly shaven with only a little hair left right at the top. Mom must keep a V of pubic hair on top of her pussy.

Even in my intoxicated state, I was hard as a rock. In all of the stories I had read about mothers and sons fucking, this would be the point where I would have pulled her panties aside and fucked her. But this was my life, and I would never ruin it for a few minutes of pleasure. After taking one last look, I gently pulled her skirt down, crawled onto the couch beside her, and fell asleep with my head on her chest.

I woke a few hours later with Mom's pussy pressed into my hip and her leg over my cock. I looked, and her eyes were still closed; she was dreaming, and it was a good one if the soft moans indicated anything. This lasted only a few minutes, and she stopped and returned to soft breathing, while I lay awake with my hard-on trying to bust out of my shorts. I must have fallen asleep because when I finally woke up, I was spooning Mom, and I had my morning wood firmly planted between her ass cheeks.

"OK, Troy, time to get up. I need to use the toilet something fierce," Mom said, straightening up and pulling away from my cock like it was going to bite her.

"Sorry, Mom. I couldn't make it to my own bed," I said as I tried to hide my erection.

"I must have had a good dream. It could have something to do with Bernie playing with Loise's honey pot all night under the table," Mom said from the bathroom.

"Yes, in the early hours of the morning, you were making some noises like you were dreaming about something nice," I said to embarrass her.

"Looks like you woke up all excited too," Mom fired back, still in the bathroom.

"It will go away as soon as you let me go to the bathroom," I said, then I heard the shower start and the shower door close.

She had done it on purpose, and I had to go in or wet myself. I opened the bathroom door and could see Mom behind the frosted glass. I stepped up to the toilet in our little bathroom, right beside the frosted shower return. I pulled out my cock, and it pointed straight up in the air. I stood there, trying not to look at Mom's outline through the frosted glass, knowing she was naked inches away from me.

"Still can't go, baby?" Mom asked, giggling.

"Not helping, Mom."

Then, Mom pushed her soppy bottom against the glass, laughing out loud.

"Also not helping."

My cock finally softened a little, and I bent it down to start peeing, the stream making what seemed to be a lot of noise in the small bathroom. I left after taking a last look at her profile, and I made us both breakfast. Mom finally came out in a light robe, her hair wrapped in a towel.

We were both wondering if last night was all make-believe when Bernie texted asking for an email address to send me the itinerary for the flights. He wanted to get going as soon as we could. The buy-in price for Bitcoin was low, and the perfect time to start our trial. I gave notice at the pub, and Mom did the same at her two casual jobs. Bernie said he would find us a tenant for our house, and we could make a decision on that later.

The removal people packed us up in no time and put it in storage until we found out if we would be able to stay on the Island or not. I think I was ready to move on from the city anyway, and if we came back, we would find something else and rent our small house permanently. Bernie had arranged for us to stay at a hotel for a few days until our flights. It was beautiful with views of the city, but it only had a king bed. We were his guest, so I couldn't really ask for an extra room, and it was only two nights, so we decided to just deal with it.

We said our last goodbyes to the few friends we worked with and headed out to dinner together in the hotel restaurant. It was a strange feeling, almost like a new start. Mom sat across from me smiling. I could see she was happy to go off on the adventure, anything other than the sixty-hour weeks that had dominated her life for the last twenty years.

"So, you are ready for this, then?" I asked, reaching out my hand to her.

"When you have been at the bottom for this long, you know to take any chance that comes your way. Let's make a pact to give this our all, not look back, and make the best of whatever comes our way," Mom said, taking my hand and squeezing.

"Agreed. To our new adventure," and held up my glass.

"A refill, sir?" the waiter asked, as he held a bottle of the champagne from the other night. "Complements of Mr. Noble."

This happened every time our glass was even close to empty all evening. I also got dragged up onto the dance floor by Mom, and we danced and drank into the wee hours of the morning. I had to hold Mom up in the lift as we headed to our room, where Mom flopped down onto the bed, fully clothed, and promptly fell asleep. It looked like a good idea in my drunken state, so I stripped to my jocks and passed out beside her.

A few hours later, I woke up as the morning sun started to peek through the window. I was probably still quite drunk as the hangover hadn't started yet. I lifted myself out of bed to pee and got some water to stave off some of the headache that was surely coming. That's when I saw the sun's rays casting across Mom's body. Sometime in the night, she had shed her clothes and was lying on her back. The sun's light touched every hill and left a shadow in every valley of her beautiful naked form.

Even in my drunken state, I could see her beauty. Her breasts were still firm but falling a little to her sides with beautiful pink areolas and nipples the size of a pencil eraser. Her pussy was right next to my face. The hair above her slit was a wide V of black short-cropped hair, and her large outer lips had stubble that meant she probably hadn't shaved since the dinner with Bernie and Loise. Her inner lips were hidden. I looked at her for a long while, then with all my willpower, I pulled the sheet up over her and went to the bathroom. I sat on the toilet and jacked off to the memory of Mom's body.

A few hours later, I felt some movement on Mom's side of the bed as Mom got up to go to the bathroom. I opened one eye to see Mom was naked running across the room. She came back covered by a hotel robe and sat in a chair next to the window looking at me 'sleeping.'

"Morning," I said after faking sleep for as long as I could stand.

"It's already past ten, the mornings almost over," Mom said, setting off alarm bells in my head.

"Shit, the flight's in two hours! We are going to miss it; the bus will take over an hour," I said as I flung the sheets off my body.

We rushed around the room, repacking our bags, and throwing on clothes like crazy people. We got down to the lobby to check out, only to find Bernie had arranged a car to take us to the airport. We both breathed a little easier, although we would still be pushing it to catch the flight. We did get there in time, and the good thing about having a hangover was that we both slept most of the trip to Thailand. We changed to a private plane for the two-hour flight to an island near our destination with an airport, then another hour on a boat to the Island, where Bernie stood on the dock waiting for us.

"Welcome to our Island! I will take you straight to your house to unpack and rest for the afternoon. I will come and get you to take you out to dinner. I find it better to stay up late on the day of the flight, to force your body to sleep at the right times," Bernie said, leading us to a waiting golf cart.

"I will be glad to see the mattress tonight, but I'm willing to hold out as long as possible if it makes the jet lag better tomorrow," I could feel the day's traveling wearing on me.

Bernie took us past houses that seemed to be built into the undulations of the Island. From the front, they were mostly glass, but once you went past, all you could see was grassy mounds where the building's roof should be. As we went up the slope, I realized why this was so important. The view was spectacular over the coastline of the Island and out to the enclosed coral cay. It was a large area that looked like it might be a mile across and was almost fully enclosed from the sea with the waves crashing on the outer rim, but the water inside was calm as a teacup.