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Two Weeks at the Playground Ch. 04

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Billy learns the ins and outs of pleasing his mother anally.
9.4k words
4.73
45.2k
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Part 4 of the 6 part series

Updated 06/09/2023
Created 04/06/2020
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JoMaddox
JoMaddox
1,876 Followers

"Harder Billy Harder!"

Young Billy Martino's body was bathed in sweat as he pumped away deep into his luscious mother. It had been a day and a half since Monica Martino and her son had first made love to each other. Yesterday, the incestuous couple had spent the day hanging out together in their cabin, talking and looking at the waves hitting the beach. But most of the time Monica and her 18 year old lover-son had spent the day in bed. Any reservations about committing incest with her boy were far far away in the rear view mirror as Monica and Billy were now more than mother and son. They were lovers in every sense of the word.

The hard body milf mom lay flat on her tummy as her sweat soaked youngster was on top of her, driving his 18 year old cock deep into her hungry hole. Monica loved the feeling of her son's big balls slapping her ass with each thrust of his young prick.

"BILLLYYYY!! YESSS!! GIVE IT TO MOMMYYYY!! HARDER!!"

"MOM, I CAN'T LAST!! I'M GONNA...OH SHIT MOM!! YESSSS!! HERE IT CUMMSSSS!!"

The teenager had remembered the words that the beautiful Miss Helen had told the boys...when you are ready to orgasm...push deep and hold. With one last thrust the youngster pushed his swollen cock as deep into Monica's dripping cunt as he could. The boy grunted in pleasure as his ball sac delivered a huge load of thick incestuous sperm into his screaming mother.

"EEEEEEIIIIIEEEEEEE!! YES!! IN MEEEEE!!" EIIIIIIIIEEEEEEEEEE!"

The lovely 40 year old milf screamed in pleasure as she always did when she orgasmed. Gone was Billy's shyness and awkwardness. He knew he was becoming an expert at making his mother one very very happy woman. A part of him was starting to wonder what was going to happen when this two week fuck fest with his mother was over and when mother and son went back home. Would things go back to the way they were before? Or had the last several days made his mother a cock hungry fuck slut?

"Darling, that was wonderful! Thank you for waking up mommy like that! I want to wake up every day like that from now on."

"Mom, instead of setting your alarm clock every morning, I'll be your alarm clock."

"MMMMMM!! Darling...yes. I'd like that very much. Yes, wake up every morning...with my darling boy's alarm...COCK!"

The two lovers lay there. Monica looked at the clock. Its past 11 in the morning. Mother and son had lost track of time as this morning's fuck fest had lasted over two hours.

"Billy, we better get up. Hurry! We have to be at Miss Helen's cabin at 12."

"Mom, do we...gotta go? I think I'd just like to have out in bed with you all day."

"Darling, we gotta go. Miss Helen has another lesson for everyone today."

The youngster is a bit disappointed, but maybe he'll learn a couple new things. Plus he'll be able to check out Miss Helen, the drop dead 50 year old blond sex bomb. He wonders how that arrogant kid named Julian was able to make that drop dead gorgeous older blonde with the big tits happy in bed. Maybe if he's lucky, he'll be able to see her...naked.

Billy hurriedly showers and puts on some khaki shorts and a nice polo shirt. Monica steps out, dressed in a cute green pair of short shorts. She has left her light green blouse open in front, showing off her cleavage. Billy suddenly feels bad. He can't wait to see the lovely Miss Helen naked and is starting to fantasize about someday fucking the long legged blonde beauty when his sexy mother is there...openly throwing herself at him. He better get all thoughts of Miss Helen out of his mind and concentrate about making his mother happy, in and out of their heart shaped bed.

Monica grabs Billy's hand as they walk up the steps to Miss Helen's cabin at the top of the hill.

"Mom, what do you think we're gonna learn today?"

"Darling, don't know. But I think you'll agree, Miss Helen hasn't steered us wrong so far."

"No mom, she hasn't."

When they get to the door Miss Helen greets them. Billy can't take his eyes off the magnificent older blonde. What Billy's mother now knows is that her darling son has tons of pictures and videos of mature women in their forties and fifties. For awhile now, the youngster had secretly gotten totally into older women Miss Helen's age. Billy would love to somehow get some pics of the striking blonde beauty before he and his mother go back home.

Miss Helen is wearing a very pretty white lace silk robe. Her long blonde hair and make up are impeccable. The blonde beauty has applied some sort of body lotion so that her long perfect tanned legs and big round tits shine in the afternoon sun. She even smells good, like vanilla. Billy's cock starts to stir. He tries to cover it up, not wanting his mother to see he's getting hard for another woman.

"Hello, Monica...Billy. I can see you two are absolutely glowing! It looks like you two are..connecting."

"Yes, Billy and I are definitely...connecting...!!"

"I'm so happy for you two. I'll say when the two of you arrived a few days ago, I wasn't sure about you two. But the transformation has been amazing. Billy, I can see the signs. You sweetie have gone from an awkward kid...to a young virile man in a couple days."

"Ummmmm THANKS."

The teenager had trouble even getting the words out. He can't believe it! He has become so...confident around sexy older women, but just now, the beautiful Miss Helen, with the long slim tanned legs, big fake tits, and vanilla scent, and huge fuck me smile, has fried the his 18 year old brain.

"Julian is in the shower getting cleaned up. He should be out in 10-15 minutes. The others should be here in a couple minutes. Would you like a bite to eat?"

Helen has set out some sandwiches and drinks. The room has a huge heart shaped bed in the middle, quite a bit larger than the other cabins.

"Yes, I'll take a sandwich. Billy, I know you're hungry."

Billy grabs two of the little sandwiches and a cola. Even after this morning's fuck fest with his mother, the teenager's cock starts to stir. The lovely blonde immediately picks up the vibe.

"Billy and I didn't have time this morning to eat. One thing led to another and we looked at the clock and it was after 11."

Helen gives them a naughty smile. Her eyes travel down trying to get a look at the bulge in the youngster's lap without letting Billy's mother get any ideas.

"Billy...it sounds like you had a case of...morning wood for your mother."

"Uhhhh...yes."

Just then the Thai beauty Jade and her son Panit arrive, holding hands. Soon the others arrive and Miss Helen starts talking to the group.

"Okay, everyone. I'm sure Julian is about done in there. Let's get started."

"Did anything happen to Anaya and Rajeesh?"

The mother and son from India walked out the other day and haven't been seen since.

"Well, I don't want to get into details but Anaya and Rajeesh are doing great. Seems that they had a few problems with mixing their love for one another and their Indian culture. So Julian and I have been over to their cabin several times for some...personal counseling sessions. They're doing great. But they won't be here today."

Miss Helen looks at everyone. The three 18 year old boys can't take their eyes off the older blonde beauty. Miss Helen looks straight at Monica, gives her a wicked smile. Monica shyly looks back and smiles back. She gets immediately aroused. Did they just have...a moment? She can feel a tingle in her cunt. Is she starting to feel a connection with the older blonde?

"Okay everyone, let me go check on Julian."

She goes to the bathroom and knocks.

"Julian, how much longer sweetie?"

"Five more minutes mom.."

"He'll be out in five minutes. So I'll start without him. Boys, I'll just tell you, Julian is just like all of you. Several months ago he was just a regular kid. He's quite a soccer star back at home. He goes on dates with girls but he was a virgin just like you."

Just then Julian walks out. His jet black hair is combed straight back. He is wearing just a pair of maroon jockey shorts.

"Hi darling. You look...incredible. You ready?"

"Mom, I'm always ready."

"I haven't told all of you yet but I have three sons. Julian here is my youngest. Like you boys he just turned 18 a couple months ago. And since his 18th birthday, as you'll see today, Julian is well on his way to becoming quite an accomplished lover."

Julian walks over to his exceptional blonde mother. They wrap their arms around each other and kiss, swapping tongues. Julian has his hands on Miss Helen's ass, running them over her tiny perfectly round globes.

"Mom, are you going to...put on...the...heels?"

"Sorry sweetheart. I just got all excited thinking about today."

"Julian loves to see me in 5 inch heels. He says it makes his...penis hard looking at me in them. I'll just tell you that today...everything were going to perform for you...Julian demands the heels never come off."

Billy looks over at his mother who seems to be ignoring him. She can't take her eyes off the blonde beauty and her handsome 18 year old son. That's fine with Billy. He can stare all he wants at the gorgeous milf Miss Helen.

Julian grabs his sexy blonde mother and picks her up They playfully laugh as he walks over to the bed and almost throws her on the heart shaped bed. The three love seats are arranged at the edge of the bed so that Billy and Monica have a face on view of Helen and her son.

"You going to make love to your mother, sweetheart?"

"No mom, I want to fuck the living shit out of you."

The sexy big titted blonde squeals with delight and puts her arms out. She and her son are locked in an embrace, their hands all over each other.

"Okay everyone, now you just sit there and watch everything we do. We're going to have sex a lot of different ways. We just want to show you that there's a lot of different ways you can have fun. Julian has turned me on to...anal sex so at the end we'll show all of you how we do it."

They kiss, and Julian unties her robe. Her huge perfectly round silicone melons are finally free. Julian roughly pulls her tiny white silk panties down and Helen spreads her long legs. The aroma of the vanilla body lotion fills the room as everyone gets a close up view of Miss Helen's gushing wet cunt. Monica looks closely at the tiny patch of blonde hair above her wide open love hole. She now knows why Miss Helen wears the tear drop swimsuit and panties. The tiny blonde strip is shaved, perfectly matching the tear drop shape. The sexy brown haired mother's eyes are fixed on the blonde beauty. She has never been sexually aroused by another woman but for the first time in her life she realizes something's happening.

Billy's eyes are also focused on Miss Helen's now open cunt. He can almost see inside the spectacular blonde's pink wetness. His mind tries to burn the image of the 50 year old blonde bomb into his memory bank. What he doesn't know sitting next to him, his mother's cunt is now also dripping wet. Monica wishes that she could get just a little closer look at Helen's snatch.

Julian picks up Helen's tiny butt and hungrily starts to lick her cunt.

Her ass is 2 feel off the ground as the teenager devours his mother's beautiful blonde womanhood.

"JULIAN...EAT IT!! EAT YOUR MOTHER'S..OHHH SHIT YESSSS!! DON'T STOP!! DON'T EVERRRRR STOPPPPP!!"

Helen then quickly turns around, and gets on all fours. Her ass still two feet in the air, Julian gets a close up view of his mother's asshole. She reaches back and pulls her ass cheeks apart. The youngster sticks his tongue out and quickly gives Helen's asshole a quick lick.

"Mates, I'm going to give my mum quite a good fucking before I get down to the main event."

"Julian sweetheart. You want mommy's ass, don't you boy? You want mommy's...asshole?"

The teenager licks her ass cheeks. He doesn't seem embarrassed at all performing in front of a group of other hot mothers and their sons. Billy watches intently, hoping someday he can be an expert like the lucky 18 year old from South Africa who is intent on fucking his exquisite mother's ass in a few minutes.

"Julian!! Yes!! Mommy's asshole is ready for your big cock."

Monica grabs Billy's hand and places it on her thigh. Not daring to take his eyes off the blonde beauty, he runs his hand up his mother's legs. Monica guides the boy's hand inside her panties. Billy can feel the wetness gushing out of his mother's cunt.

"Mom, first I'm going to fuck the shit out of you a lot of different ways. If you're a good mum then I'm going to fuck your tight little ass and shoot my jizz into your little shitter."

"OHHH JULUANNNN... YES!!"

Julian buries his tongue in Helen's tight butt hole as she moans. She suddenly sneaks a look at Monica sitting on the couch. As their eyes meet, she gives her a sexy smile and nods yes. Billy picks up on the fact that his mother and the sexy 50 year old blonde seem to be making a lot of eye contact. Is Lady Helen...performing for his mother?

"Mom, I'm gonna lay on my back. You're going to get on top of me and ride my big cock...really good."

On the couch, Julian lies on his back. The long legged blonde climbs on her son's prone body, facing away from him. She stares right at Monica. Monica lets out a little gasp as she realizes that the lovely Miss Helen is staring right at her. Helen spreads her legs and lowers herself in her son's throbbing fuck stick. In a few seconds she is totally impaled on 10 inches of teenage cock.

"Everyone this is called the reverse cowgirl. This is one way my son's penis can get really deep into me. This is one of my favorite...positions."

"MY GODD...JULIAN!! YOU KNOW MOMMY WANTS IT THIS WAY!!"

The blonde fuck bomb slowly rides the lucky boy's cock. Julian grabs his mother's vanilla scented body and thrusts upwards as mother and son start fucking in earnest. The blonde's big silicone hooters shake as the boy fucks his sexy mother.

"HARDER JULIAN!! YESSSS!! I'M

GOING TO...ORRRRGGGGASSSSMMMMM!! AAAAAAAAAAAAAAAAAA!! AAAAAAAAAAAAAAAA!!"

Billy and Monica, sitting at the side, can't get a great view of the boy's cock thrusting into the sexy blonde. Helen then lays on her back on top of her boy as he grabs her huge firm tits for support and keeps thrusting upwards. Helen's cunt is dripping wet, making a tiny puddle on the bed sheets. Billy looks over and next to them one of the other boys, Danny, is standing up at the side of the bed. His mother has his cock in her mouth and seems to be fingering herself. He puts his hand on his mothers thigh and works up. Billy gets a finger inside Monica's panties and feels a river of wetness oozing out of his mother.

On the bed, Helen is now on her side facing Julian. They kiss, the boy's cock still in his mother. She then turns over on her side facing away from her boy. Helen puts one long leg in the air as Julian grabs her and fucks her from behind. Both Monica and Billy are surprised at the boy's staying power. Billy know he couldn't have lasted more than a minute inside the 50 year old fuck goddess. Billy figures he probably would have cum at least twice by now.

"Mom, I'm going to get my cock between your big fake tits. I want to show my mates here how I fuck your big fake tits."

Helen then gets on her back and points to her huge fake boobs, Julian knows what to to. He quickly straddles the blonde, crawls up and places his cock in the valley between her tits. She pushes her tit mounds together and the boy moans as his throbbing cock is happily trapped between the two mountains of silicone tit flesh. Julian starts thrusting, the youngster's cock head suddenly pointed at his mother's flawless face. Her hot steel blue eyes can't look away from the beautiful sight of her own son's pink cock head.

"Mates, are you watching this? See how my's cock is all excited. Boys if you play your cards right your mother's gonna let you fuck her titties just like this, aren't you mothers?"

The four mothers and sons look at each other and nod yes. Monica and Billy make eye contact, his hand still fingering his soaking wet mom.

"Billy, would you...fuck my tits like that? I'd love it if you did..."

"Mom...hell yes I'd like it."

"And... shoot your sperm all over my face? Or in my mouth?"

"Yes mom...all over your face...then a second time in your mouth..."

On the bed, Julian and his mother's bodies by now are totally bathed in perspiration. Her long beautiful blonde hair is a mess but she doesn't care. She is totally getting off having three other women and their sons, especially Monica and Billy, seeing how sexy she is. For a second her mind again wanders off, wondering how it would be with Billy's teenage cock in her while she feasted on Monica's little cunt.

As the three teenagers and their mothers watch, everyone realizes that Julian has fucked his mother for almost an hour nonstop, changing positions and pacing himself so he doesn't orgasm until he is good and ready. In several months his sexy mother has taught him well. His sexy milf mom has had three mind blowing orgasms as her prize 18 year old stud-son is ready to finally get what he wants. He straddles his gorgeous blonde mother and points his throbbing cock at her mouth. Helen knows what the boy wants. Julian speaks to the three boys sitting at the side of the bed.

"Mates...don't you think it's time my mum got a big load of my jizz in her belly? Mum...go ahead. You know what to do..."

The teenager gets on his tummy, puts a pillow under him so as to raise his ass in the air. He spreads his legs.

"Mum, why don't you tell everyone how much you love to lick my ass...?"

It is very clear that the 50 year old blonde beauty has totally switched gears. It is very apparent that her son is now the one in charge.

"Everyone...Julian is right. I mean moms, look at that ass on my boy. I absolutely love to love to lick Julian's anus.

"Okay mom...you want it. Get it..."

"The lovely Miss Helen gives a squeal of delight as she goes down on the youngster. The three mothers on the bed try to get in for a closeup. Billy can't resist asking his mother the question.

"Mom, are you going to...? I mean...to me..?"

"Billy!! Quiet darling. Mommy doesn't want to miss any of this."

The blonde beauty, grabs her son's hips and pushes her tongue as far as she can into the boy's ass.

"Come on mum!! Lick it...! Lick your boy...ahhhhh shit yes mom!! You are a great ass licker...mum..."

Julian then looks at the three boys watching intently at the side of the bed.

"I mean...look at my pretty, high class mum! Look at how much she LOVES my 18 year old ass..."

After quite awhile, Julian tells his mom...

"Okay mom...Its finally time. Tell me what you want."

"Julian...PLEASE!! Don't tease me anymore..."

"COMON MOM!! TELL ME!! TELL ME WHAT YOU WANT!!"

"Julian...please stick your cock in my ass and fuck me..."

"Mum...its your turn...get on your back...spread your gorgeous long legs wide for me...and pull those little ass cheeks apart. Let the boys see way inside..."

Helen, the prim and proper beauty, the gorgeous, classy, flawless beauty is now a sweat soaked mess. She reaches behind her and spreads her ass cheeks apart.

"Mates...get in here and take a good look at my beautiful mum. Look at her. She's all spread wide open for me. I mean mates, look. You can actually see inside her high class asshole. What normal 18 year old kid can say no to THAT??"

Billy Martino would give anything to have his camera there to take a picture of the beautiful blonde milf.

"Mum...tell me what you want..."

"Please Julian, don't make mummy wait any longer..."

"Come on mum, you can do better than that. You want my big teenage dick in your high class asshole? Then mum...BEG me for it...!"

"PLEASE!! JULIAN!! PLEASE!! MUMMY...IS SO HORNY!! MUMMY NEEDS YOUR BIG TEENAGE COCK!!"

JoMaddox
JoMaddox
1,876 Followers


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