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Two Weeks at the Playground Ch. 05

Story Info
Monica and Billy spend a day with Miss Helen.
8.8k words
4.76
33.6k
57

Part 5 of the 6 part series

Updated 06/09/2023
Created 04/06/2020
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JoMaddox
JoMaddox
1,870 Followers

Two days later, Monica and Billy Martino were spending the day holding hands just walking the beach. Their lives had changed quite a bit in the last few days. The horny teenager and his sexy brunette mother couldn't get enough of each other. They had fucked in every position that Miss Helen and her son Julian had showed them. They also learned to seduce each other using their eyes. Thay had learned to make love to each other. And they had learned to fuck each other's brains out.

As the warm sun shines and the waves come in from the ocean breeze, the youngster puts his arm around her mother as they walk along the beach.

"Mom, this is perfect isn't it?"

"Yes. Billy I never knew a place like this existed. I'm going to be sorry when this ends."

The teenager suddenly realize that their days at the Playground are numbered. He struggles asking the question.

"Mom, what's going to happen...when we get back home? I mean you're going back to work and I'm going to start going to college, but what about...?"

"Us? You want to know what about us? Billy to be honest I really haven't thought about it yet. I mean I guess we have to decide whether we just go back to the way things were before..."

The teenager's mood drops in an instant. He looks at the sand, thinking that all of this will be over in a few days.

"Or...we could...just continue on the way things are now."

"Mom, if I have a vote I think you know what I want."

"Billy, I'm having the time of my life. And I don't want it to end either. But right now I have to think about it."

"Sure mom."

"Kiss me darling."

"I love you mom."

"I love you too, darling, more than you'll ever know. You know Billy, I have an idea. Lets go up to the botique. Right now I don't want to think about heading back home. I'm in the mood for some shopping. You want to go up there with me and help me pick out some new...naughty things to wear?"

The teenager's mood quickly improves. What horny 18 year old kid wouldn't love to spend the afternoon picking out some new fuck me lingerie with his gorgeous mother?

As they walk into the botique, they see Anaya and Rajeesh, the mother from India and her son. They are over in the corner of the store. The sexy dark skinned beauty holds up a pair of skimpy panties and her son nods yes. Giggling she grabs 6 pair in different colors. The boy and his mother seem to be lost in their own world.

"Mom, the other day, they walked out on our lesson. But it looks like they're doing okay."

"Yes it does."

Monica and Billy walk over to the huge row of ladies intimate playthings. Billy sees one very interesting see thru purple romper that he likes. He holds it up for his mother's approval.

"Mom, I'd love to see you in this. I can see right through it."

"Okay, darling, that's one. Look at this one..."

Just then they hear a familiar vice.

"Monica! I've been looking for you. Hi Billy. How are you two doing?"

The two lovers are startled by a voice which seems very familiar. Billy's cock starts to harden when he he realizes that it's the sexy Miss Helen. Just being close to the sultry 50 year old blonde, Monica's cunt starts to moisten, thinking back to the kiss she and the lovely resort owner had shared.

"Uhhh...Hi Miss Helen. Billy and I are definitely having the time of our lives. We were just telling each other that in a few days we have to get back to the real world. Neither of us want this to end."

"I can see that by the looks on your faces how happy you are. In my opinion, you are the best looking couple we've ever had here. It looks like you two were built for each other."

"Helen, did Julian leave? Did he end up going to his soccer camp?"

"Yes. I put him on the plane yesterday. But not before I sent him back with two nights he'll never forget. But truth be told...I'm pretty depressed today."

"I can see why. I don't know what Billy and I would do if we were ever seperated like that."

"Yes, I'm depressed. Plus I'm hornier than hell. My little boy Junior got quite a workout."

As Billy can't take his eyes off the blonde beauty, Miss Helen tells them that little boy Junior is her dildo.

"Monica, I have to tell you, I had the best time the other day, just hanging out with you. It seems like we have a...connection."

Monica never told Billy that she and the older blonde fuck goddess had shared a very intimate kiss.

"Yes, I definitely felt that too."

"Billy, you don't mind if your mother and I...spend some time together?"

"No Miss Helen. Mom and I have already talked about it. I think it's cool she has a friend."

"Hey I have an idea. Monica, put that away. I just got two huge boxes of new bikinis and lingerie, plus a huge box of high heeled shoes. They're actually samples of next year's sexy intimates. They want me to try everything on, see how they fit and want my opinion of which things they should bring out for next year. Why don't you come over? We can spend the day trying on sexy playthings."

"That sounds like a lot of fun. Billy, are you okay with that? Maybe I'll come back later with some things that will rock your world."

"Hey, you know, maybe its better if Billy came too. That way we can model this stuff and we can get an expert opinion from a normal teenage boy. Billy, what do you think? Would you like spending the day with me and your mom modeling sexy lingerie?"

The 18 year old boy can't believe that he's going to spend the day with his sexy brunette mother and the drop dead 50 year old blonde. They are going to model all kinds of nightgowns and stuff...for him?

"I'm sure Billy would love it, wouldn't you darling?"

"Billy, you're going to be okay spending the day with two incredibly horny older women...parading around in sexy clothes. Are you sure you're okay with that?"

"Yes...Miss Helen. Definitely...yes."

Monica gives her son a huge smile. She has a feeling that the sexy older blonde is coming onto her son. Maybe it would be good for her son to be around another woman, especially one so beautiful and sophisticated.

"I'll have some wine delivered to my cabin. Billy do you drink wine?"

"Yes, I'll probably have a glass or two."

"Then we're out of here. Lets go."

The blonde sex bomb leads Monica and Billy back to Helen's huge cottage. Both mother and son are starting to get aroused by the sight of Miss Helen's incredibly toned legs and ass as they follow her up the trail to her cabin at the top of the hill. Once inside her cottage they walk into the second bedroom where three big cardboard boxes have been opened.

"Helen, you weren't kidding. Three boxes stuffed with..."

"Fuck me clothes, Monica. Call them what they are...fuck me clothes."

Just then a good looking young boy room service comes with a case of white wine.

"Thank you Ricardo. Ricardo, I want you to meet my friends Monica and Billy, from the US."

"Nice to meet you."

"Ricardo's mother was actually a chef at a five star restaurant. She's in charge of our kitchen at the resort."

After the boy leaves Monica has a question.

"Uh...Helen, so Ricardo's mother...works here?"

"Yes. You should see his mother Olivie.. all dressed up. She's definitely a Latin..sex goddess."

"Oh, so Ricardo...and his mom...?"

"Oh God yes. I mean look at that boy. You saw him. He's just a spectacular...latin hunk. His mother is one...very lucky lady to be getting that every night."

"Helen, are all your employees...??"

"I know what ypu're going to ask me and the answer is definitely yes. All of our employees are mothers who are sleeping with their sons."

"Billy, put the wine over there. This ought to last us all afternoon...or whatever. Before we get started are you two interested in a little...weed?"

Monica looks at her son who is carrying the case of wine to the kitchen.

"You mean...?"

"Just a couple puffs each. Trust me, you two will enjoy it. It will help the three of us get into a little more...playful mood."

"Well, if you think so. What about you Billy? You game?"

"Uh...sure mom."

The beautiful blonde milf rolls a joint and hands the lighter to Billy. He lights the joint and Miss Helen takes a couple drags, deeply inhales then slowly lets it out. She hands the joint to Monica.

"Am I supposed to inhale?"

"Yes."

"You know, I've never done this before. I've never even smoked a cigarette, but here goes."

Monica takes a drag then tries to inhale. She coughs, her lungs full of acrid smoke.

"ACK!! ACKKK!!"

"Monica, thats okay. You just inhaled a little too much. Next time just take a little puff. Billy, here, go ahead and try it."

The teenager nervously takes a puff, inhales a bit, and lets it out. Not coughing like his mother, the teenager has a smile on his face.

"Billy, you inhaled it like a pro! Are you sure you never smoked weed before?"

"No maam."

"Billy, please don't call me maam. Maam makes me sound like an old lady."

"Okay Miss Helen, sorry."

The joint is passed around several times. Monica and her son are slowly starting to get totally relaxed.

"Billy, why don't you open a bottle of our wine."

By now Monica's 18 year old son has become an expert with a wine bottle opener.

"You know Helen, Billy had no idea how to open a bottle of wine before we got here. He's become quite good at...a lot of things, haven't you darling?"

Billy seems a bit embarrassed. But the few puffs from the joint has made him quite relaxed.

"Helen, thanks to your lessons, Billy's becoming quite a good...lover.

He told me he wants to become as good as Julian."

Helen smiles. The weed has made Monica a little high.

"Well, I thought we'd start with the two of us modeling some of the new things for Billy. I want to see how a lot of these thinks look like on you, Monica. With your brown hair and your...hard body, some colors will look better on you than they do on me and vice versa. Billy, you're going to be the expert, so we don't want you getting drunk, okay?"

"Sure, Miss Helen."

"Billy your mother and I are going to go into the bedroom and put on a couple things, okay? We'll be back in a couple of minutes."

The teenager sits on the couch as the two women head off to the second bedroom. Monica and her new friend start going through the merchandise. Each box has been sorted and labeled.

"Look at this robe. Its absolutely beautiful."

"Monica yes. The look is...elegant. Let's start with this one. Give me the pink one and why don't you go with the red one?"

The two milfs quickly get out of their clothes and put on the silk robes.

"Let's find a pair of panties what matches the robe. We don't want to show our teenage fashion critic all our goodies...at least not yet."

"Helen, the material feels so good. Is it pure silk?"

"Yes. It's got a pretty hefty price tag but most of our guests don't care. They only care about what kind of reaction it will have on their son's cock."

As they rummage through the assorted panties they start giggling like two schoolgirls. Many of them are just a string and a tiny crotch. Monica holds up a pair of tiny black ones that catches her eye.

"How about these? I have a feeling Billy will like them. I know they'll get his cock nice and hard. I know I like them a lot."

"Monica, not yet. Let's put on something a little more conservative to start. Then one by one we'll get to the good stuff."

"I like that idea. I think Billy will like that too."

"Monica, let's have some fun with Billy. Let's start out slow but then we'll drive him crazy. After all he's spending the day with two horny older women. Monica, today, just play along with me, okay?"

The weed has made Monica agreeable to anything.

"Okay. What about these panties?"

Helen agrees that the more conservative panties are perfect. The blonde fuck goddess quickly puts on a pair of the sexy pink panties and hands the red ones to Monica.

"Well, how do I look?"

"Helen, you are absolutely stunning."

"I hope Billy likes what he sees."

"I know he will. I have noticed the reaction he has whenever he sees you. Helen, that horny boy of mine would like you in anything."

"And Monica I hope you like what you see too. Because I'm getting horny already, just looking at you."

"Yes... I am too. Helen, you are absolutely...stunning."

The 40 year old mother and her 50 year old friend walk out in their silk robes. The teenager can't believe his luck. Two hot older women are giving him a private lingerie show! This is way better than anything he has ever seen on the internet.

"Billy, what do you think?"

The women have tied the robes so that they are partly open in front. Billy can see the mouth watering cleavage between Helen's prefectly round silicone melons. As his eyes travel downward he gets a partial view of her matching pink panties.

"Billy, look at your mother's red panties. Does your mother look good in these red ones, or is there another color you like?"

"Nnnnn...no. I like...red...and the pink ones on you, Miss Helen."

Helen walks over to the boy. The weed and a half a glass of wine has already started to take effect. Monica knows that she's to play along with whatever Helen has in mind.

"Billy, go ahead and feel the material of my panties. Thats not satin, its pure silk."

Billy is a bit nervous as he runs his hand on Miss Helen's pink panties. He doesn't want his mother to get mad if he accidently gets a feel of the gorgeous blonde bomb.

"Billy, now go ahead. Feel the material in the crotch."

The youngster's cock is hard as he feels the tiny crotch of Miss Helen's tiny pink panties.

"Billy, isn't the silk...soft?"

"Uh...yes...it...is..."

"I can't tell you how good they feel...down there. And I can see you're hard. So, Billy, I guess these silk panties...are keepers?"

Uh...yes..."

Back in the bedroom, the two milfs have another drink of their wine.

"Well, that went well, so far. Billy seems to be getting into it. Let's pick out something a bit more...racy."

Helen picks out a short white romper that's open in front, along with a tiny pair of white satin panties. The crotch isn't the normal triangle, but rather one called a tear drop. She hands the matching black outfit to Monica. As Monica puts on the tiny tear drop, she notices that some of her pubic fuzz sticks out of the side.

"Helen, look. I guess to wear these you need to...shave down there."

"Yes, I see that. I try to keep my vagina shaved in a long narrow strip. But if you look I have a bit sticking out of my panties too. I like to have just a tiny pube or two sticking out so that he gets a tiny taste of what he's getting."

"Helen, are these panties just too...revealing?"

"No dear. Maybe later today we better both ...shave just a bit down there. I'll show you how to shave my vagina like I do."

"Okay."

"Or I have an idea. Do you think Billy would like to shave us?"

"I bet the poor kid's hands will be shaking so much, that he won't be able to hold the razor steady."

"Look at these. My godd those are sexy!!"

"Yes, those 4 inch stilettos will work just great. The same company has a 5 inch fuck me special model that we'll try on later."

"Miss Helen, I'm having such a wonderful time. You are so...nice..."

The sultry blonde comes closer to her new friend and looks into her eyes.

"Yes...and you girl are so very very sexy."

They kiss, then again a second time. Monica has never in her life fantasized about a woman but she's definitely feeling something she's never felt before. Her cunt is starting to moisten.

"We better go out and model these for Billy."

For a minute Monica completely forgot about her darling 18 year old son in the other room.

"Yes...we better...show these to Billy."

The two horny women walk into the room and the teenager's cock starts to harden again. His smoking hot mother and the gorgeous older blonde are wearing a skimpy little top and some tiny panties which are way more revealing than the first ones.

"Billy, these tops are what they call rompers. Billy, see how the top accentuates...my boobs?"

The teenager's eyes travel back and forth between Helen's big round fake tits and his sexy mother's more natural ones. He sees the edges of four nipples staring him in the face.

"Do you like your mother's black romper, or my white one?"

"Helen, don't put my son on the spot. Don't make him choose. I bet you like both of them, don't you darling? Helen, if you want the answer look at his..."

"Yes, I can see the outline of his hard penis in his shorts. Monica, let Billy get a closer look at our panties."

The two women get close to Billy, giving his a good view. The two women are openly throwing themselves at him.

"Billy, do you think there's just too much pubic hair sticking out? And how about mine? Can you see just a little of my blonde...pubic area?"

"Well..."

"Helen, you're flustering him! He likes them both, don't you darling?"

"Uh...yes..I...do..."

The two milfs show Billy a half dozen more sexy outfits and several string bikinis. By now the three of them are almost through their second bottle of wine.

"Billy, there's only one more your mom and I are going to show you, but maybe we should light up another joint. How about it Monica?"

Monica looks at her son and they nod yes. Both of them are having such a good time neither one of them want this day to end.

"Billy, would you like to light me up?"

They pass the joint around. This time Monica knows what to expect. She can immediately feel her insides getting warm all over. Looking at her darling 18 year old son openly staring at the gorgeous older blonde is making her pussy moisten.

The two milfs go back into the second bedroom and are finally getting to the bottom of the boxes. There is one more outfit for them to model for the horny teenager.

Helen holds up the tiny hot pink see thru teddy and string panties. The matching hot pink 5 inch stilettos make the lovely Miss Helen a complete fuck goddess.

"How about this? If this doesn't get him, trust me, nothing will."

"My godd Helen! I love them! And I know Billy loves to see me in orange. The top feels like it fits perfect."

"Hurry and get your stilettos on, so I can check you out."

Monica quickly puts on the orange see thru teddy and tiny matching panties.

You know hon, orange isn't one of my colors but I must admit, it looks pretty good on your beautiful body. Now look down at the bottom of the box, grab the orange tube and the pink one.

Monica grabs the two tubes of lotion.

"Hon, this is flavored lotion which goes with the corresponding outfit. Let me put some of the orange lotion on you. It's actually orange flavored."

Monica stands there anxiously as the gorgeous blonde expertly rubs the flavored oil over her body.

"Let's get some on your ass...everywhere. Now go ahead hon, and put the strawberry oil on me."

Monica's hands are shaking as she nervously rubs the oil on the gorgeous big boobed blonde.

"You know Helen, this is the first time I have ever touched another woman. Sorry if I'm a bit clumsy."

"No hon, you're doing just great. I'm a bit nervous too. I don't ever do this with anyone, but you are just so sexy I can't stand it. Truth is I've only been with one other woman in my life."

Helen lets out an...OOOHHHH!! YES!! as Monica runs her hand up and down the backs of her long tanned legs. Monica is definitely feeling the buzz from the weed. Completely uninhibited, she has to ask the sexy blonde...

"Helen, are we going...to...have sex? You and me? And Billy?"

"Monica hon, only if you want to...and only if Billy is comfortable with being with two women...incredibly two horny older women. Let's see what happens."

As they stand there in the 5 inch stilettos, Helen can't believe how sexy her new friend Monica is. Her tight little ass is perfection.

JoMaddox
JoMaddox
1,870 Followers


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