Two Weeks at the Playground Ch. 02

"Ladies and gentlemen, we are now on our final approach. The weather is currently 28 degrees celsius and the current time is 2:30 pm. We want to thank you all for flying with us today. And by the way, for the 4 couples who are headed for the Playground Resort please make your way to concourse D, gate 12. Your water taxi has just pulled up to the dock and is waiting for you."

Monica Martino and her teenage son look at each other and take one last drink out of their cocktails. The sexy mother, wearing a short skirt, blue silk top and matching heels has spent most of the flight holding onto her son's arm for support as the jumbo jet has encountered quite a bit of turbulence. As the plane finally touched down the passengers cheered, glad that the rough flight was finally over.

"Darling, thank you for letting me hold onto you. I'm usually a pretty good flyer but I'm just glad I had my big strong hunk to grab onto."

As mother and son finally set foot on the ground, mother and son looked at each other.

"Kiss me darling. We made it. We're here."

The youngster opened his mouth and Monica kissed her son like never before. She held her slim sexy body against the teenager and kissed him squarely on the lips.

"Mom, we gotta hurry. Don't want to miss our water taxi."

Holding hands, mother and son hurry through the airport and finally see the sign for the water taxi. Billy notices there are 3 other women at the gate along with 3 young males, who all look under 20 years old. Monica smiles at the other women.

"I guess this is the water taxi for the Playground Resort?"

Monica reaches out and shakes hands with a good looking blonde who looks to be in her forties. Her son looks around 20.

"Yes. My name is Penny. This is my son Danny. Where are you from?"

"Just outside of San Francisco."

"Oh, you are from America. It looks like in our little group here you two are the only Americans. Danny and I are from New Zealand."

One by one the other couples introduce themselves. Looking at the others, one couple stands out. There is a very pretty tall dark skinned woman and her young son who can't be 5 feet tall. The kid looks very nervous.

"Hi. I'm Anaya. This is my son Rajeesh. Were from Mumbai."

"Hi. Monica and Billy, from San Francisco."

The last couple is a strikingly beautiful tall Asian woman dressed in black boots and a very short black miniskirt. Monica thought it strange that she was wearing sexy black boots on such a hot day.

"Hi, Jade from Bangcock and my son Panit."

As Monica stuck her hand out to meet the couple Billy noticed that the Asian boy's hands were shaking. He is having trouble making eye contact with anyone.

As the four couples took the water taxi out to the resort, Monica holds onto her son in the choppy water. Finally at the entrance of the Playground Resort the 4 couples are greeted by a stunning older blond woman and a young male who looks quite a bit younger than 20.

"Hello everyone. Welcome to the Playground. My name is Lady Helen. I'm the owner and will be your host for the next two weeks. This is my son Julian. We're so glad you all finally made it. Understand the plane ride was rough and the water taxi wasn't much better."

Everyone looks at each other and nods.

"I know everyone is tired from the long trip you all have made to get here, so we will walk up the hill to the main resort and I will show you a lot of our amenities."

As they walk into the main desk they notice that most of the mothers and sons are holding hands. They walk over to the main pool. The huge area is full of women mostly in their 30s and 40s, each with a young boy. Some of the women are playing in the pool with their sons, while others are just laying out enjoying the hot sunshine. One couple is kissing while several other mothers are laying on loungers while their sons are rubbing lotion on their sweaty bodies.

"Here is the main pool. In this pool, bathing suits are required. We do have another pool which is clothing optional."

Monica quickly looks at Billy, smiles, and shakes her head no. Billy smiles back and nods yes! The teenager ended up going to a clothing optional resort after all!

"We do have another entirely private pool that we will be using for your seminars starting tomorrow."

"Our amenities include have a hiking trail for anyone interested. All of the hikes feature a lot of private coves so the two of you can enjoy some quality alone time. All trails lead back to the resort so it's impossible to get lost. Also, tennis courts and a mini putt putt. Our ocean beachfront is totally private. We schedule it so that on mondays, wednesdays, and fridays, swimsuits are mandatory. The other days are clothing optional. And every evening after dark, the beach is clothing optional."

Billy Martino, two weeks after his 18th birthday, realizes that he has hit the jackpot! Two weeks at this swanky place with his smoking hot mother? Hopefully he can talk her into some of the options that are clothing optional.

"Here is the gift shop. With your mother son package each couple has $1000 credit for clothes in our gift shop. Buy yourselves a couple new dresses for our once a week dances...maybe a couple new bikinis for the beach. Boys get yourselves some new pants and some nice shirts. We want all of you boys to look your best for your mothers."

"The main dining room is what we call semi casual. Boys must wear a nice ironed shirt and slacks and mothers must wear a dress. Short sundresses are perfect. Bermuda shorts for boys are fine but no gym shorts or workout clothes. And no pantsuits for you mothers."

"Now one thing. Displays of affection like kissing and some affectionate touching are not only permitted but encouraged. But if mother and son desire something more...intimate, we ask that you go back to your own cottage. Except on the beach after dark, more intimate activity is not permitted."

Monica Martino knew from looking a the brochure that this might be something new for herself and her shy inexperienced teenage son. She just hopes that her 18 year old boy doesn't expect...sex. That isn't going to happen. The stunning blonde resort owner Miss Helen goes on.

"I know that you have traveled a long way at great expense to be here, so trust me when I tell you that each of you that you and your son will have a very unique wonderful time here. We have made this resort one of a kind and want you to come back often."

"I'm sure you'd like to get to your cottages and unwind for a little while. Follow Julian and myself. All the cottages are exactly alike so we will show you around then assign each one of you to your own cottage."

Billy and his mother hold hands as they follow the group down the hill to one of the cottages. Billy's cock starts to harden as he checks out the owner Miss Helen from behind. She looks a little older but she has definitely taken good care of herself. She looks better than any of the milfs he has downloaded on the internet. Her face has absolutely no wrinkles, and her steel blue eyes seem to be able to look right through you. The slim long legged blond is wearing a white open backed sun dress along with some white heels which make her long tanned legs go on forever. The 50 something milf is dripping with gold jewelry.

Even though this lady might be 50 she's still smoking hot. Monica can sense that her young son seems to dote on her every word. Miss Helen opens the first cottage and the group goes inside.

In the middle of the living room is a huge heart shaped bed. Monica notices right away there are mirror on the ceiling.

"Here's the bed. They're all going to be the same. Each room has it's own refrigerator, and huge bathroom with a small hot tub as well as a traditional bathtub and huge shower. Each cottage opens up to the ocean so you can look out and check out the waves every evening as well as the great sunsets we have here at the playground."

Miss Helen assigns the first cottage to Anaya and her son Rajeesh.

"Okay everyone. it's just past 4 pm. Let's give everyone a couple hours to get situated and we can all meet in the dining room at say 6 p.m. We will have our first seminar along with your dinner."

One by one each couple was assigned their own cottage. Finally Monica and Billy are assigned their own cottage.

"Monica, Billy, I forgot to tell the others that each cottage is entirely soundproofed in case you two want some loud music, or something else."

"Thanks Miss Helen. Thank you too Julian. We'll be there at 6."

Finally alone in their own private cottage Billy asks his smoking hot mother.

"Mom, is this...some kind of sex resort? Sure sounds like it."

"Billy, I'm not quite sure what we've gotten into, but it kind of looks that way. I guess we're stuck here for two weeks. Might as well make the best of it."

"Mom, remember on my birthday back home you said we just might have some...naughty fun. What did you mean?"

"Well, I really am not sure. Let's go to this first seminar and at least see what happens. Are okay with that?"

"Sure mom, but a seminar? I mean, here we are at this beautiful place and they want us to go to seminars?"

"I know. I saw your eyes light up when you heard about all of the clothing optional stuff. I saw you checking out Miss Helen. She looks to be the age of all those porn models you have on your computer. But none of them can hold a candle to her. I bet you'd like to see her all naked."

"Yea mom, but I'd rather look at you naked for two whole weeks..."

Monica pretends not to hear her 18 year old son telling her he'd like to spend two weeks looking at her naked body.

"We better get cleaned up and get ready for our first lesson, whatever that is. You go ahead and jump in the shower. Comb your hair and put on your new black slacks and gray shirt."

As Billy walks into the living room the teenager was greeted with a huge smile from his adoring mother.

"Billy, MMMMM!! YES!! I LIKE!! I like the way you look darling."

"Thanks mom."

After a wonderful shower Monica dried herself off and opted for a burgandy sundress with matching heels. She put on her favorite gold necklace along with a pair of tiny hoop ear rings. Some make up and lipstick and she is ready. She nervously steps out of the bathroom hoping that her darling son likes what he sees.

"MOM!! SHIT!! YOU'RE JUST...SO...HOT!"

"So you like your old mom, all dressed up like this?"

Mom, you put all of those others to shame."

"Even Miss Helen? I saw the way you looked at her. Billy, I see all the stuff on your computer. I know for a fact you are into older women. "

"Mom, honestly. You definitely put all of them to shame. I'm so glad you and I are here."

"Me too darling. You know, I promised you that I brought some...fun things to wear."

"Yes mom, and when can I see your, like you call them, your fun things?"

"If you play your cards right, you just might see me in a very very...fun outfit later on. But right now lets head up to the dining room. I'm famished."

Monica and her son walk into the dining room and is escorted to another room, where the other three couples from today were sitting at a table. The gorgeous Miss Helen and her son were there chatting with Jade from Thailand and her son. The slim Asian beauty was wearing a very sexy black skirt, a silk black top and patent leather black stilettos. Even though she was talking to the beautiful Miss Helen, Jade's teenage boy couldn't keep his eyes off of his sexy long haired mother.

"Okay everyone. Lets get started. First of all I'd like to know a little about everyone. Remember that Julian and I are going to be your guides through all of this. So everyone go ahead and lets get started."

"Hi. I'm Anaya and this is my son Rajeesh,from Mumbai India. We're so excited to be here."

"Anaya please tell us a little about yourselves."

"Well, my husband died a couple of years ago so I'm left at home being a single mom. Rajeesh is a wonderful son. We are here to help Rajeesh become a more confident around girls."

"Rajeesh, do you have a girlfriend?"

"No. I've been too busy getting ready for college. I did have a girlfriend but not any more."

"Rajeesh, are you...a virgin?"

The teenager is obviously embarrassed.

"Rajeesh darling. Don't be shy. I'm going to ask all of you boys if you are virgins. So go ahead."

"Uh...yes."

"Anaya now look at your darling boy. You'd like to learn how to become one with your son, wouldn't you?"

"Yes, I'd like that very much."

"Everyone, our motto here at the Playground Resort is two become one. Our goal is that mother and son come to our resort as two and by the time you leave you'll become one..."

The other two couples introduced themselves to the group. Finally it was Billy and Monica's turn.

"I'm Monica from San Francisco and this is Billy. I actually was given a trip from my boss at work. I checked it out and thought it would be perfect for me and Billy. Billy's father left us years ago and like all of you I'm a single mom."

"Billy, are you a virgin?"

"MMMMM...yes. I'm not too good around girls. Mom says I'm just too shy."

"That's fine Billy. We are going to help you with your shyness. Is there a certain girl at school that you like?"

"Uh,not really. Maybe someday..."

"So Billy, are you maybe interested...in...older women?"

"Uh...yes."

Miss Helen knows most teenagers at the resort are into their mothers. She knows that she has struck a nerve with the clumsy teenager. Not wanting to embarrass the youngster she backs off.

"So all four of you boys are virgins. Billy, Monica, would the two of you like to learn how to become one with each other?"

"Yes. Billy and I would like to learn the techniques to do that, wouldn't we Billy?"

The youngster wonders what this is all about. Billy Martino wants nothing more than to get out to the beach and see his smoking hot mother in a string bikini. He wonders what the smoking hot classy Miss Helen looks like naked. The teenager's hormones are going a mile a minute and he has to sit through some stupid seminar about becoming one with his mother.

"Great job everyone. Now let me tell you a little about me. I'm Helen from South Africa. Like you I'm a single mom, but I've raised three boys. Jonathan my oldest is 24. Jason the middle boy just turned 22, and Julian here is 18."

The young boy named Julian smiles and all the mothers say hello to the somewhat shy youngster.

I started this resort with my oldest son Jonathan 6 years ago when he was 18. After Jonathan went off to college it was Jason's turn. Now it's Julian's turn. Several months ago Julian was a total beginner at this but he and I are well on our way to becoming one. Lets just say the two of us are having the time of our lives together, aren't we darling?

"Yes mom. It's been great. Mom tells me I'm well on my way to becoming one with her."

"Okay everyone, tonight's lesson will be a lesson in dining room behavior. Everyone go to one of the booths. First everyone order a cocktail, something to get started."

The waiter goes around, gets everyone's order and quickly comes back with drinks for everyone. Billy wants to get out on the beach and stare at his mother in her bikini and maybe rub tanning oil on her back and he has to sit through some stupid seminar on dining room etiquette.

"Okay everyone, first, everyone is sitting all wrong. When you go out to a fancy restaurant with your mother, never ever sit across from her. Everyone, now sit next to your partner. Good, now boys, sit real close to your mother, close enough so that your legs are touching. Now mothers, boys, each of raise your glass and share a toast with your mother...something...private...something that makes her happy. Tell her how beautiful she is and how lucky you are to be her special boy."

Billy's cock starts to harden as he looks at his beautiful sexy mother. Not quite a string bikini but the teenager realizes that his hardbody mother does look pretty hot. Her diet and gym workouts have certainly paid off. The teenager decides to go ahead and get with the program if it makes his mother happy.

"Mom, you are absolutely beautiful. I am so looking forward to sharing the best two weeks of my life with my favorite girl."

"Thank you darling. You know how much I love you. You are the only guy in the world that I'd want to be here with. I can't wait to become one with my wonderful guy."

"Mom, now I'm supposed to say something private, right. Hows this? Mom, I can't wait to see you in your...fun stuff."

"I have a feeling were gonna get to the fun stuff later on, darling."

Lady Helen speaks up.

Now boys look at your mothers, look at each other, Try to look into the windows of your mother's eyes. Once you get inside those windows she's all yours. Moms, look into your son's eyes. I want the two of you just to look at each other for the next 5-10 minutes. Don't say a word to each other. Just look into each other's eyes and try to penetrate the barriers that each of us has created. Tonight is about breaking down the barriers so that you and your son can start to become one with each other."

The teenager looks into his mother's gorgeous big brown eyes. Monica gives her boy a huge smile. The sexy mother is starting to feel her panties starting to get wet. Billy's cock is starting to harden. He can't believe how turned on he's becoming just looking into her dark brown eyes. Mother and son cannot believe how sensual this is!

"Now everyone, take a drink, and we'll go on. Now as well as looking at your mom, take your hand and gently graze her cheek. Now run your hand down her chin. Mothers, now its your turn to respond to your son. Gently slowly open your mouth just a little and run your lips across his cheek. Now gently...gently now, kiss his cheek. Now the other cheek. Good. Its important that the two of you never lose eye contact. Remember the eyes are the most sensual organ in the body. Okay good job everyone! Now lets go ahead and order some dinner. We have a lot more to get to after dinner."

"Billy, I can't believe what I'm feeling. Yes, you are definitely going to see me in my...fun stuff."

As the waiter goes around to each table, Miss Helen speaks up.

"Boys it's important that you are in charge here. It's okay to ask your mother what she'll have for dinner but its important that you tell the waiter what the lady will have. Remember boys, you are the male. When you were younger your mothers were in charge. But now, you are to be the dominant one. And your mother will respond to your sudden dominance."

"If anyone needs another cocktail its a good time to get that out of the way before you get your meal."

Monica tells Billy to order a second glass of wine for her. Billy quickly downs his wine and orders a second one as well. The teenager has never had two glasses of wine at a time, so he hopes he doesn't get drunk. He certainly doesn't want to miss out on any of this. His hard body mother is getting pretty touchy feely. Maybe he'll get to see her in her panties and bra!

"Okay, everyone doing okay so far? Good, now it's a good time to talk about trivial things. Maybe your plane flight, maybe the trip to the airport, anything."

"Well, Billy how are you doing so far?"

"Just fine mom. I never realized that just looking into your eyes like that...was..so...hot."

"Billy I have a confession. When we looked at each other like that, and you felt my cheek...you know I could feel my panties start to get wet."

"Mom...might as well tell you. My...I mean...I got all...hard just looking at you like that."

Monica starts to wonder about the next two weeks in a private

oceanfront cabin with her 18 year old hunk, sharing the same bed.

"The lady will have the medallions of tenderloin, medium, with the bearnaise sauce on the side. I'll have the t-bone rare with baked potato and everything on it."