Two Weeks at the Playground Ch. 03

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Monica and Billy continue their lessons from Miss Helen.
11.5k words
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Part 3 of the 6 part series

Updated 06/09/2023
Created 04/06/2020
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JoMaddox
JoMaddox
1,877 Followers

"BILLY!! GO AHEAD!! SHOOT IT!! ALL OVER ME!!"

The brown haired mother's eyes go from her son's face to the spectacle happening a couple feet from her face. With her dildo buried in her panties, her teenage son is about to let go with his first orgasm of the morning.

"MOM??? WHERE???"

"GET UP HERE DARLING!! CLOSER!!"

The 18 year old boy crawls closer to his beautiful mother's pretty face. The inflamed piss hole is slowly opening, ready to unload on Monica's face.

"ON MY FACE!! DARLING!! ALL OVER MY FACE!! PLEASE!! BILLY...HURRY!!"

"MOM!! I'M GONNA!! SHOOT IT!! OOOHHHH GODDD YES!!"

"MOMMY'S CUMMIN TOO BILLY!! COMON DARLING!! SHOOT IT!!"

The teenager starts to unload. The first rope of cock butter hits his mother's cheekbone and left ear. Another hits her eye and lands on her forehead.

"BILLYYY!! I"M CUMMMIN TOOOOO!! EEEE!! IIIIIIIIIII!! EEEEEEEE!!"

Monica's high pitched scream fills the room as the teenager coats his pretty mother's face with his morning orgasm. She smiles wickedly at her son as the last couple ropes hit her chin and lips. Her flawless face is covered with thick white teenage semen. The sexy mother had just dildoed her horny cunt to another mind blowing orgasm, watching her darling son stroke his virgin cock. Monica Martino, 40 year old undersexed divorcee and mother, has never been happier in her life. Totally consumed with sexual bliss, the horny mother steals a glance at the clock.

"Darling, its after 9! We better hurry. We're supposed to meet everyone for breakfast at 10."

Hand in hand Monica and Billy walk into the dining room where the other three mothers are sitting with their sons. Miss Helen, holding hands with her handsome son Julian, greets the happy couple.

"Well, good morning! Monica, I can tell! The two of you are absolutely...glowing! Someone must have had a good night."

"Well...let's just say we did, didn't we darling? And a good morning too, didn't we?"

"Yea mom...we did."

"Okay everyone we have a long day ahead of us. We have some very important things to cover today. But first of all, why doesn't everyone talk about what happened last night when the two of you got back to your rooms? Penny, why don't you go first?"

The good looking blonde from New Zealand seems a bit embarrassed to tell everyone what actually happened in the privacy of their room. Miss Helen speaks to the group.

"Everyone, trust me, getting things out in the open in a group like this is actually what has to happen if teenage boys are going to get out of their shyness. Everyone here will have a chance to tell the group what happened last night. This way, everyone can learn from each other."

The blonde who looks a bit older than the others looks at her son. In a heavy accent she starts telling the group about last night.

"Well, Danny and I got back to our cabin, and put on some telly. We kissed a little, trying to use the techniques we learned. I spread my legs a little and told Danny it was okay if he felt up my legs a little."

Okay, that's good. Danny, how did your mother's legs feel?

"Well, It felt incredible. Her legs are so soft. I kept going...higher...until I felt the edge of her panties."

"Danny I bet you wished she she wasn't wearing any panties, didn't you?"

"Then she took my hand and let me feel her panties."

"And how did that feel?"

"Her panties were all wet."

"You remember last night I told everyone to please refrain from any genital touching. But there's no right way or wrong way to do this. Today, among other subjects, we well cover genital stimulation. So go ahead. Penny, how did Danny's hands feel? Did he...stimulate your...vagina?"

"Ohhh yes! My panties were absolutely soaking wet."

"Okay everyone lets stop for a minute. When a woman's panties get wet does everyone know what that means?"

Three of the teenagers nodded yes. Rajeesh the all boy from India looked confused.

"Well, if a woman's panties are wet, it means she is what you boys call...turned on. It means your mother is ready for more. So Danny, what happened next?"

"Well, mom took her hand and she looked at my crotch and felt the top of my underwear. I could feel her hand slide back and forth along my...penis. Then...I shot in my underwear."

"Well, it looks like you two are on your way to becoming one with each other. Who's next?"

Monica looked around and said she'd go next.

"Well, Billy and I knew that we might be sharing a bed on this trip, so, realizing we both have...needs, we came to an agreement. We both agreed that...If either of us had to...masturbate, the other would turn their back to give them a little privacy. So last night when we got back to our cabin I changed into something more...appropriate."

"Monica, let the others know what you mean by appropriate."

"Well, I put on a sexy little black romper, a cute little pair of black panties and some black heels. Then I came out to the veranda and I sort of modeled for him."

"Billy, I hope you realized that your beautiful mother wore that just for you. Did you like what your mother was wearing?"

"God...yes. She looked really hot."

"So Billy and I sat out and looked out at the ocean. We kissed a lot, being careful not to get carried away. Then it was time for bed. I told Billy if he needed to...I would turn away from him in the bed...so he could go ahead and do his thing."

"You mean, it was okay for Billy to go ahead and masturbate. So Billy, you masturbated while your mother laid next to you?"

"Uh no. I tried but there's no way I could do something like that. She's my...mother."

"I knew he was really miserable. I felt bad...teasing him like I did. So I asked him if I could play with my dildo. He could watch me if he wanted to. I laid on my back and dildoed myself while he watched me. I ended up having some really huge orgasms watching him stroke his...penis. He orgasmed once on my...breasts, another time on my black panties and a third time this morning...all over my face."

The other mothers looked at each other in amazement. The lady from San Francisco and her son are really horny for each other!

"Everyone, Monica and Billy are well on their way to becoming one with each other. Good job you two. Okay now how about you Anaya? How did you and Rajeesh get along last night?

The tiny dark skinned lady from India seemed totally uncomfortable with Miss Helen's questions.

"Well, Rajeesh and I talked a lot. I looked down and saw that...inside his pajamas... his...I'm embarrassed...his penis was hard."

"Anaya, so you could tell your his penis was...hard?"

"Yes. I could tell...my God...I'm having trouble telling you this...but I could tell...his penis...was throbbing."

"Did you like...looking at your son's erect penis? Did a part of you wish...he wasn't wearing any...pajama bottoms?"

"Yes. Oh...this is so...embarrassing. But...I really liked looking at his hardness. I...wondered...what it looked like..."

"Good job Anaya. Everyone, we all have different attitudes toward...sexual customs. Anaya, for our first seminar, you are doing great. Trust me, you and Rajeesh might take a little more time than the others, but when you do make a connection, it will be the best experience in both of your lives."

"So finally we kissed each other goodnight. But...nothing happened."

"Okay, nothing happened. That's perfectly fine. As all of you can see each couple that comes here has to approach this in their own way. Now go ahead Jade. How did you and Panit spend your evening?"

Monica has had very little interaction with the pretty black haired temptress from Thailand, except to smile and nod yes a couple of times. The sexy lady has long jet black hair which she wears up all of the time, as to show off her perfect complexion and pretty green eyes. Her son Panit is quite a bit shorter than his mother. He's just a shy skinny kid who looks quite a bit younger than the others.

"Well, Panit and I started kissing on the veranda, like the rest of you. One thing led to another and well...I ended up putting my son's... penis in my... mouth."

Silence from everyone in the room. They can't wait to hear the details of this one!

"Jade, did Panit... end up ejaculating?"

"Yes."

"Jade did you...swallow it?"

"No. I was surprised at how much semen he had and how hard it came out. I didn't know what to do. So I went to the bathroom and spit it out. Then we took a wet towel and cleaned up the rest."

"Panit, how did you feel?"

"Well Miss Helen, I liked it...a lot. I never knew anything could feel that good."

"Miss Helen, his semen tasted...sweet..it was really very...warm and thick. But I wasn't sure if I was supposed to swallow it."

"Panit, did you wish your mother would have swallowed your semen?"

"Do women...mothers...actually swallow it?"

"Okay everyone listen up. Here's an important learning experience. It"s important that you swallow your son's semen. When a boy's penis ejaculates, that's part of your loving son filling your mouth. It's important that you swallow it so that his semen becomes part of your being. We will talk a lot more about this later. l can see it's after 11. We have a lot to cover today. Lets everyone hurry and go back and change into some swimwear. We will all meet out at the west pool at noon."

Monica and Billy walk back to their cabin. The whole interaction with the group has been quite exciting.

"Mom, Miss Jade actually gave her son a blowjob. And now Miss Helen says all the mothers should swallow it."

"Billy, let's hurry and change. We don't have much time to get ready. We can talk about it later."

Thankfully, Monica had successfully changed the subject. Suddenly the brunette divorcee became edgy. Does her 18 year old boy expect her to give him...a blowjob? Some playful fun, mutual masturbation, with her now adult age son was one thing, but sucking his teenage penis and swallowing his sperm was another. Monica starts changing into one of her new bikinis with mixed feelings. One part of her wished now she had brought a bikini a bit more conservative so not as to give her horny 18 year old youngster any ideas, but another part of her starts to get excited. She can feel her legs start to get wobbly and her pussy start to moisten.

The stunning milf mom looks in the mirror and likes what she sees. All of her hard work at the gym and her strict diet the last few months has definitely paid off. Monica Martino knows she certainly has the looks and the body to give any 18 year old boy an instant hard on. As long as she's doing this she might as well go through with it. She wonders what the sexy Miss Helen has in store for her and Billy. She anxiously walks out to the living room where her teenage son is standing there.

"Mom, you're absolutely...incredible."

"You like darling? You like your mother's new bod, I take it."

"Mom, by now you know I do. Just looking at you, I can't even think straight."

Monica checks out her 18 year old son. He has definitely turned out into quite a hunk. And she knows first hand that young Billy Martino has quite a cock and a big set of balls in those swim trunks.

"Billy, mama likes what she sees too. You are definitely quite a hunk. Someday you're going to make some lucky lady very very happy."

Billy looks at the clock.

"Mom, we have to be up at the pool in 5 minutes. We better not be late."

"So yesterday, you thought these seminars were stupid. Now it seems you've changed your tune. You don't want us to miss anything, do you?"

Hand in hand mother and son head up to the west pool where the other three couples are waiting for Miss Helen and her son Julian. There are four loungers in a row and one at the head of the arrangement. Just then the captivating Miss Helen, holding hands with her son Julian, walks into the pool area.

Young Billy is speechless. The smoking hot Miss Helen may be a bit older than his mother but she is definitely a blonde goddess. She has put her long blonde hair up for this afternoon's class. Monica can't believe the beautiful blonde bomb. At close to 50, her tanned skin is flawless, her slim legs are a mile long, and her beautiful fake boobs are almost falling out of the confinement of the tiny hot pink swimsuit. Monica has never been into women, but instantly her pussy starts to moisten at the sight of the exquisite blonde milf.

In fact, all four boys are absolutely speechless by the older blonde beauty. She is wearing a hot pink one piece string suit with a tiny tear drop in the crotch. Billy can even see the edge of her shaved pussy. Her long tanned legs travel upwards to the junction where they meet at her tiny round ass. The clip clop of her hot pink heels is the only sound in the otherwise quiet pool area. The exquisite blonde greets everyone with a huge smile.

"Well, everyone, are we ready to get started? I thought it would be best that Julian and I talk you through today's session. But also we will be playing along right with you so that if there are any questions, you can watch us to make sure you are doing things correctly."

Everyone looks around and seems fine with it.

"Okay, first of all let's talk about touching. To reach the ultimate goal of mother and son joining and becoming one with each other it is important that there be a lot of touching. Since we are out here and it is such a nice sunny day, maybe we all better start with some sunscreen. Mothers, why don't you go ahead and lay face down on a lounger? Great. Now boys, grab the bottle of lotion and start by putting a big gob on your mothers back. Yes, like that. Rajeesh make sure you are rubbing it in good."

The four mothers start to squirm on the loungers while their sons are rubbing oil on their backs.

"Boys, feel how soft your mother's skin is. Its a good time boys to whisper a little something in her ear like how good she looks in her bikini."

Billy reaches over.

"Mom, you look so...damn hot...I can't stand it."

"Billy, I never realized how good...your hands feel on my body."

"Now boys go down to her feet and put some oil on the back of each leg. Yes, squeeze the tube and a big long gob on each leg. Now boys slowly work the oil up the back of one leg. Now make sure you stop when you reach her buttocks."

"Billy, be careful. I know you want to touch my butt, but listen to Miss Helen."

"Now again slowly work your hands up her other leg. Make sure you get the insides of her thighs. Mothers you might have to spread your legs a little so that your son can get the insides of your thighs. Okay everyone stop for a minute and look at me. See how Julian is slowly working the oil up my legs? See how Julian just whispered something in my ear? My beautiful boy just told me how long and pretty my legs are. The result is that I am getting more than a little aroused."

"Mom, your legs are so fine. I want more than anything to put some oil on your beautiful butt."

"Not yet darling. Better wait and see if Miss Helen says it's okay."

Miss Helen talks to her son Julian loud enough so that everyone can hear them.

"Julian sweetheart, does rubbing mommy's legs like that make your cock hard? See how he smiles at me and nods yes. Okay boys, now continue on. Go ahead and put a nice gob of lotion on each of your mother's buttocks. Now here's the fun part. Boys, go ahead and rub the oil all over your mother's buttocks. This is important, make sure you do this slow. You both want this to last don't you?"

Billy has finally reached his goal of rubbing the slippery tanning oil on his aroused mother's rock hard ass. Monica squirms on the lounger, now totally into it.

"Mothers do you like your son running his oily hands all over your buttocks? Now boys watch how Julian runs his hand on my buttocks...MMMMM!! Yes...! See how my son just run his hand over my tiny...anus? Boys now go ahead and run your oily hands over your mother's anus. The result ladies is that my son, my darling boy is going to make his mother...oh GOD I'm going to...ORGASM!! UUUUUHHHHHHHH YESSSS!!"

Young Billy Martino, his hands literally shaking with excitement, runs his hand on Monica's ass. He slowly gently puts his finger on the edge of his mother's tiny brown ring. Its Monica's turn to scream...

"OH GODDDDD BILLLYYYY!! MOMMY'S CUMMINNNNN!!

EEIIIEEEEEEEE!"

Next to them the sexy black haired Jade howled in ecstasy while her son Panit played with his mother's tiny asshole.

"Now Moms, turn around now. Now for this part moms you have a choice. You can leave your bikini tops on or take them off. I suggest you take them off, otherwise you'll get tanning oil all over your swimsuit."

Monica smiled at her teenage son and let Billy untie her bikini top. Her gorgeous tits sprang free from the confining top. Billy stole a glance at lady Helen and couldn't believe what he saw.

Lady Helen's tits are fake! The spectacular perfectly round circular orbs screamed to be let out of the tiny swimsuit. The teenager has tons of porno back home with milfs in their 40s and 50s with big fake tits. The youngster has never seen anything remotely like the feast belonging to the 50 year old milf. For a minute he became jealous of Helen's son Julian.

All of the mothers had their tops off except the dark skinned Anaya from India. Her and her son seemed to be enjoying themselves even though Billy thought that her son Rajeesh seemed very clumsy around his sexy Indian mother.

"Okay boys...now this time start at your mothers feet...and work slowly up each leg. Nice and slow. Make it last. Boys remember you don't want to rush this. You have all day to play with your mother. Now mothers, spread your legs so your son can rub the lotion on the insides of your thighs. Be careful not to touch your mother's private area. We'll get to that one later."

Monica spreads her legs and gives Billy a huge wicked smile. Monica never knew anything could be so much fun. She looks at her teenage boy and can see how his big hard cock is straining in his swimsuit. Monica knows she and Billy will have a lot fun tonight masturbating for each other.

"Billy, your hands...feel so good on me. We're going to have to do this more often."

"A lot more often...mom."

"Yes...definitely a lot more often."

"Now boys go ahead and put some lotion on each of your mother's beautiful breasts. Boys remember, you suckled on your mother's breasts when you were infants. So boys, go ahead and make sure you rub your mother's tits really good. Again don't hurry this. If you look over here see how Julian is rubbing my breasts. Julian sweetheart, you love mommy's big titties don't you? MMMMM!! That's my good boy..."

Billy finally has an opening to stare at the big titted blonde beauty who is getting her big fake tits massaged by her lucky 18 year old son. Monica's pussy starts to moisten at the sight of the Miss Helen's spectacular silicone melons and long sculptured tanned legs. She tries to get the blonde beauty out of her mind. For a second she wonders if she is sexually attracted to the older blonde milf.

"Mothers, look down at your sons and see how his penis is straining to be let out of his swim trunks. That means that both of you are totally aroused. Now its your turn to apply oil on your son. Boys turn over. Mothers, put lotion on your sweet young boy, maybe whisper something into his ear.

Monica reaches over so that her tits brush against Billy's back.

"Billy darling, you have some nice big cums for mommy later on? Gonna shoot it all over my titties...and my panties like last night? God I hope so! Cause I 'm gonna give you a really naughty show later on. Mommy will have some nice cums for you."

"Now mothers rub the oil on your son's chest. Good job everyone. Penny, it looks like you have your hand inside Danny's swimsuit. Is his penis nice and hard, Penny? Good. Your son's penis is nice and hard for you Penny."

JoMaddox
JoMaddox
1,877 Followers