Two Wees at the Playground

The unmistakable sounds coming from Billy Martino's bedroom filled the house. Yes, the high school senior was at it again. Tonight for some reason the sound coming from the teenager's bedroom was a little more intense than usual.

"Thump!! Thump!! Thump!!"

The familiar noise from the boy's bedroom had become a nightly happening in their very nice but small two bedroom house. As she lay in her bedroom down the hallway Monica Martino looked at the clock. It was just before 2 am, same time as usual. Her teenage son Billy was in his bed, obviously masturbating.

The soon to be 40 year old divorcee had read all the articles and books about a single mother raising a normal teenage boy and knew that this was just a part of a normal kid growing up. Billy Martino, without a father figure in his life to guide him in the ways of the world, will have to do it with only the help that a single mother could give him.

As Monica lay there she knew there was no way she was getting back to sleep until her son was done in there. A few months ago she realized that the sounds of healthy teenage boy beating his meat every night was starting to have an effect on the undersexed mother. Monica toyed with the idea of some night getting the courage to pry the door open just a bit and watch her son go at it. But she never got the courage to sneak a peek. She knew that invading her son's most private moment would change their relationship forever.

The increasingly intense rhythm of the youngster was starting to make Monica wet. Her horny cunt was dripping from excitement. The brown haired divorcee excitedly grabbed her dildo from the nightstand. As long as there's not going to be any sleep for awhile and as horny as the sounds of her young son was making her, she might as well....yes two can play this game!

Suddenly...from her son's bedroom...

"MOM!!! OHHHH MOMMMM!!! SHIT MOMMMMM!!! OHHHHH!!!"

The cry of her teenage son was too much. Did she hear right? Did her son Billy just cry out for his...MOM? What was happening in there? Is everything okay? Did her darling boy somehow hurt himself and suddenly need her help? Her attention was now on full alert.

"MOM!!! YES MOM!!! GO FOR IT...MOM!!!....SUCK IT!!!.PLEASE!!!..."

The soon to be 40 year old mother heard the headboard hit the wall as her son was really getting into it.

"MOM!!! FUCKKKK ITTT MOM!!! RIDE MY FUCKIN' COCK!!! YES MOM!!! SHIT!! YOUR CUNT IS SO...FUCKIN' TIGHT!!"

The horny divorcee just lay there. The pretty brunette mother could feel the wetness developing in her swollen cunt as she listened to the spectacle happening in her son's bedroom down the hall. Her teenage son was thinking about her as he was jacking off!

"THUMP!! THUMP!! THUMP!!"

The young son was obviously getting into a good rhythm. The now dripping wet divorcee tried to picture in her mind the vision of her teenage son in his bed laying on his back running his hand up and down on his erect cock, the red cock head glistening with precum in the pale light. Monica could picture the inflamed piss hole opening wide, ready to shoot it's teenage load high in the air.

"GONNA FUCK YOU MOM!!! GONNA FUCK YOU GOOD!!! YES MOM!!! YES!!!"

The sound coming from her son's bedroom was too much for Monica. The lonely divorcee licked the rubber cock head, then ran her tongue along the 10 inch shaft of the fake penis. Monica would always make sure her rubber "lover" was coated with her juices before she plunged it in and out of her hungry mommy hole. Her mind then traveled back to the other room. From experience she knew her teenage boy was ready to blow his nuts.

"MOM!! GONNA...CUM MOM!!! GONNA...YES!! IN YOUR...FUCKINNN CUNT!! UHHHHHHHHHHHHHHH!!"

In the playground of her mind, her teenage son Billy was on top of her, pumping away, his sweat dripping off his young virile body as he shuddered and emptied his balls deep into his mother. The fantasy in her mind was becoming more and more real as she plunged the rubber phallus into her hungry mommy hole.

"YES BILLYYY!!! OHH SHITTT YESSSSS!!! FUCK MOMMYYY!! HARDER BILLYYY!!! HARDERRR!!!"

Monica Martino was in her bed flat on her back, her long beautiful legs in the air and spread wide as she thrust the rubber dildo harder, harder into her dripping wet tunnel. The lonely divorcee slowly opened her eyes and suddenly realized something was a bit different this time.

Shit! Her bedroom door was open halfway, and standing there...watching her...was...Billy! The teenage boy was speechless, just standing there, stroking his big young cock . The horny brunette divorcee tried to block the reality of the moment out of her mind, hoping perhaps this is just all a dream. Monica Martino, 39 year old single mom, only knew one thing....she had to cum...now! Right now the need in her neglected cunt was just too much. She didn't care if her son watched her or not. She'll just have to deal with this episode later.

The dark haired beauty's brain was losing the battle with the need in her swollen cunt. If he is there watching me, might as well give my darling son a good show.

The lovely mother gave her son a sexy smile and not saying anything, continued her assault on her neglected gash. The undersexed brown haired milf's legs flew apart giving her teenage son a great view of the dildo thrusting in and out of his sexy mother's dripping wet tunnel. Monica's legs started shaking as she was nearing her orgasm.

"FUCK ME BILLYYYY!!! FUCK YOUR MOMMYYY!!! SHIT BILLY IT'S SO...FUCKIN'...GOOD!!! YOUR FUCKINNN COCK...IS SO FUCKINNN BIGGG!!! MOMMY'S CUMMIN!!! CUMMIN REAL GOOD!!! GO AHEAD!!! CUM!! IN YOUR MOMMMYYYYY!!"

Monica drove her dildo all the way into her hungry cunt then held it there as her whole body shook and shuddered.

"CUMMMINNNN!!!! AAAAAAIIIIIEEEEEEEEE!!!! AAAAIIIIEEEEEEEE!!!!"

A couple minutes later the horny divorcee caught her breath. She looked at the door and no one was there. Did her young son see her spread wide, fucking herself senseless with the rubber dildo, screaming his name as she had the best orgasm of her life? Or was it just a dream? In the intensity of the last few minutes Monica wasn't quite sure exactly what happened.

The next morning Monica stood in front of the stove wearing a navy pantsuit as her teenager bounded down the stairs. The divorced mother was nervous as hell, not knowing how to handle what had happened last night. From now on things were going to be very very different around the Martino home.

"Morning mom."

"Morning darling. You better hurry and eat your breakfast. Don't want to be late for school."

As her son wolfed down his eggs and toast, the embarrassed mother tried to best to see any sign that maybe this morning things were going to be any different. Mother and son chatted about Billy's big history test and how Monica was taking her car in for an oil change after work. Thank God nothing seemed any different this morning. Maybe, just maybe, the sight of her teenage son in the doorway was just a dream.

"Billy you better hurry. Have a good day darling."

"Bye mom. I love you."

"Love you too darling."

The 39 year old divorcee looked in the mirror as she started getting ready for work. Monica put on her make up, and fixed her hair she thought for a minute about her life. She once striking Italian beauty started to think about coming to the realization that at 39, maybe her best days are behind her. She has been so busy with her successful law career that she has let herself go the last few years. Monica Martino has worked herself up the ladder at her law firm so that now she has become one of the premier young attorneys in the country specializing in corporate mergers and buyouts. She has spent the last three years dealing with a huge multi billion dollar mega merger. And she has done it without sleeping with any of the corporate executives or horny clients.

For some reason today the olive skinned beauty realizes that she is starting to become a bit overweight. Her thousands of hours dealing with the merger has left her with very little time for herself. She realizes that with only one parent her only child has suffered as well. Yes, she'll have to start going to the gym and go on a diet and do something about her weight. The relationship with her son hopefully will sort itself out when the merger is finally put to bed in the next few months.

Things at home the next couple weeks were totally normal between her and her teenage son. There has been no mention of that night that Billy had watched his sexy lush mother fucking herself senseless with her dildo. The clumsy teenager has even been a little more willing to help around the house. His grades at school have actually improved and he has even applied for several colleges. Just a couple months away from 40, the divorced mother knows that she's pretty lucky to have a son who seems pretty well adjusted, although he never seems to mention any girls at school. Monica just wished that her shy boy was a little better with the opposite sex. The youngster has inherited her ex husband's rugged dark good looks, slowly turning from a young boy into a young man who some day will be worthy of his father's nickname "Italian stallion."

The week before Christmas Monica had gotten a huge folder at work. Inside the folder was all of the paperwork from the merger. After a couple years of intense negotiating the other company had agreed to all the terms and was ready to sign as soon as possible. All of her hard work was going to pay off.

Once the paperwork was signed, one of the largest corporate buyouts in history was done. The president of the law firm had summoned her to his office. He gave his best employee a big manila envelope.

"Monica, I can't tell you how happy we are with your work. I must tell you that you are well on your way to becoming a full partner. For all of your work on this case we have decided to double your personal commission."

As she stood there Monica did the math in her head...a million and a half, just her cut of the legal fees.

"Why thank you, Mr Baxter."

The president handed Monica a manila envelope.

"Monica, the partners know how hard you have worked on this merger. I have here a two week all expenses paid trip for two to any resort in this envelope. There's over 20 to choose from. We all know how hard you have worked to make all this happen so please take this so you and your husband can get away from everything here at work and can reconnect."

"Well, Mr Baxter, I don't have..."

"Monica, I don't want to hear it. You two get away for awhile. And by the way this two weeks will not count towards your annual vacation. This is just a special gift from corporate in New York."

That night, young Billy is sitting in front of the television waiting for his mother. Friday night at the Martino house was movie night. It was Billy's turn to pick out tonight's movie. The teenager had chosen the new one with the black ex cop who ends up killing the local gang leader. Not one of Monica's favorites but she really doesn't care. Just the fact that she's spending the evening cuddled up on the couch with her young hunk of a son is more than enough for her.

The lonely divorcee comes into the room wearing a pair of sweat pants, sweatshirt and carrying the big envelope. Billy's mother had a huge smile on her face. She seems to be in a particularly good mood.

"Mom. what's up? Have you made the popcorn yet?"

"Not yet darling. I want to tell you something. I know that with all of this merger business I have neglected you. I haven't been the parent I should have been. But now that all of this is over I plan to make it up to you."

"Mom, I know how all of this has been a stress on you. I'm okay. But I do really look forward to maybe spending more time with you."

"Well darling. I had a really great day at work. First of all the president just doubled my commission on the merger. It means that you and I are going out this weekend and start shopping for new cars. Maybe a new Mercedes sedan for me and a new sports car for you. I can't wait to see my darling son driving around in a sexy new...chick magnet."

"Mom, I don't know about that. I'm not really too good around girls. But it would be cool to tool around town with my beautiful mom."

"Billy, the president also gave me something that I want to show you."

Monica opens the envelope and a couple brochures come out.

"Darling, the president also gave me a two week vacation for two....to any resort in this envelope. There's over 20 to pick from."

"Mom, that's cool! I know how hard you work, but mom, a trip for two? You going to bring one of your girlfriends or...?"

"No way silly. It's a trip for two and I'm definitely gonna take my favorite guy. That is if you're cool with hanging out at a five star sunny resort with your old mom for a couple weeks. I was figuring we could go...the week after your graduation. That way it would be sort of a graduation present."

"Mom, I mean, you're going so some high class Caribbean resort and you're gonna take your...kid?"

"Darling, I figured...I mean...you just turned 18 and we never really celebrated your special day. I know in most of those places 18 year olds can legally drink alcohol. Maybe we can find some clubs and go dancing. Maybe we can even get drunk together..."

"I mean, shit mom, you're hotter than hell. What if you meet a guy in the next couple months? Mom, maybe you'd better start going out to bars and find yourself someone."

"Darling, bars aren't really my thing. No way. I've already decided. I'm taking my hunk of a son. That is, if you're okay...."

Just then Billy's cock starts to harden. The idea of hanging out with his sexy mom at a sunny resort for a couple weeks....maybe, he'll be able to see her in a bikini! The teenager already starts to wonder about the sleeping arrangements. Shit, if he is stuck sharing a hotel room with his sexy hot mom, how will he be able to...take care of his...business?

"Okay then, its decided. You and your mom are going away for two weeks after your graduation. That way we can spend some quality time together before you go off to college. Let's go through these brochures and figure where we want to go."

One by one Monica and son her teenage son look at the different brochures.

"Mom...this one is a two week stay in a sex resort. Look at the brochure. It says that it's for couples who want to explore complete sexuality."

"Well, we certainly don't want to go there Billy."

"Mom! You sure? Maybe you'd meet someone and maybe I'd meet someone."

"Or, maybe you'd end up getting stuck with your old mom for two weeks at a sex resort."

Monica and her teenage boy continue going through the brochures.

"Mom, here's a nudist resort. I'd kinda like that one mom."

"Yes, buster! I bet you would! Two weeks of looking at all those naked young girls. I know once you saw some hot young thing you'd leave your old mom all alone for two whole weeks. And how would you ever be able to walk around the resort with your penis sticking out for two whole weeks? You know if we went there, you know I'd have to be naked too."

"I know mom. That's the whole idea. I could really get into...seeing you...naked for two whole weeks."

"Billy, if you saw your old overweight mom for two whole weeks, you'd lose interest. I'm not exactly in the best shape like all of those porn models on your computer."

Billy knows now that his mother has seen "mature women" websites on his computer. He now knows that his mother knows that he in interested in older women. Hopefully he hasn't checked his internet history. Shit! She will see all the mother-son websites he has visited!

Yes, darling, your mother has seen all of those websites you visit. Those...what they call milf sites?"

The teenager now can't make eye contact with his mother. The mood shifts when they continue looking at the brochures.

Billy looks at the next one. It's a swingers resort in the Bahamas.

"Billy let me see. This one's another one...for couples who swing. The brochure says there are orgies every other night. Scratch that one."

One by one mother and son check out every brochure and end up having two to choose from.

"Mom...these are all...like...sex resorts...this one is clothing optional."

"So, buster. You'd like to see your old mom in...nothing at all? Darling.. you know, that naked thing just might work two ways. You ever thought that maybe your mom just might want to see her darling son....naked?"

The teenager just sat there speechless.

"Darling I know. You've already seen everything I have. You know that night you were in the hallway watching me doing....something....to myself. It seemed like you liked watching me."

The lighthearted mood suddenly changes. The teenager just looks at the floor. There's no way he can look at his mother. Monica knows she has suddenly hit a nerve. She takes the last brochure out of the envelope.

"Darling, here's the last one. This place calls itself the Playground. This features a two week trip just for mothers and their sons. Here, let me read it to you. Spend a wonderful two week getaway with your son at our five star Caribbean resort. On your personal journey mother and son will totally connect as your son takes his final steps into manhood. Mother and son can take a walk along our five mile white sand beach, relax in your own private spa, go dancing in our huge lounge, have a private dinner in our 5 star dining room, or just hang out in your room and enjoy the view. Your stay includes many different seminars and activities geared for mothers and sons."

The teenager looks at his mother. Two weeks with his sexy mom? Going to...seminars? And activities? That sounds too much like going to school. The teenager secretly hoped that maybe his mother would change her mind and pick a clothing optional resort.

"Billy, if you're okay with this one? Or ...I bet you want to go to that other one...the clothing optional...?"

The teenager knows that he better speak up right now or he'll end up spending two weeks going to seminars with his mother. But somehow the teenager just doesn't say anything.

"Mom you won the trip. You decide."

"Okay then. We're going for two weeks to the one called the Playground. We'll have the time of our life."

Shit!! Two weeks going to boring seminars. He was this close to spending two whole weeks with his lush naked mother. That would have been at least a couple years worth of jack off fantasies.

"Darling, it's a few months before you graduate. I'm going on a diet and start going to the gym. I want you to be proud of your old mom."

The movie was a pretty good one. Yes, the detective killed the drug kingpin. Tonight for some reason his mother cuddled up against him and actually went to sleep halfway through the movie.

As winter became late spring Billy noticed something was very different with his mother. It seemed every night she would come home from work about an hour later than usual. She stopped eating bread and stayed away from desserts. She seemed to start becoming more and more obsessed with her appearance. The soon to be 40 year old mother also started becoming a lot more touchy feely with her teenage son, sometimes even teasing the horny youngster, flashing him with a peek at her new sexy underwear. The teenager actually started looking forward to spending two whole weeks in a hotel room with his sexy hot mother. Maybe he'll "accidentally" get to see her naked!

As spring became the middle of May late one afternoon Monica came home from work carrying a several packages from the new lingerie store at the mall. Today was Monica's 40th birthday. Her loving teenage son had promised her a special surprise for her special day. Monica walked into the house to the sight of two pieces of salmon, Monica's favorite, sitting next to the barbecue. She could see that Billy had set the dining room table, had dimmed the lights, and had even lit some candles.