mom watching son masturbate story

dannope

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I wonder if someone can help me out. I'm looking for a story where a gorgeous mom watches her 19 yr old son masturbate. It isn't sexual, mom is just watching because she feels bad for her son. The son is pretty much a loser, no school or work and just masturbates all day. Mom is helping out and keeping him company while he does it.

Thanks in advance if anyone can come up with this.
 
I wonder if someone can help me out. I'm looking for a story where a gorgeous mom watches her 19 yr old son masturbate. It isn't sexual, mom is just watching because she feels bad for her son. The son is pretty much a loser, no school or work and just masturbates all day. Mom is helping out and keeping him company while he does it.

Thanks in advance if anyone can come up with this.

More details, please. I mean, when she watches him, does she spy on him ? Or does the boy know that his mom is watching ? Or since you said she is helping him out ... does she takes his cock and masturbate him ?

This would be cool: Mom catches him, masturbating. He is embarrassed, but she tells him that masturbation is ok. Of course, Sex with another person is much better. To prove it, she just wants to show him how it feels when another person touches your private parts (and I mean touching, not masturbating) She grabs his cock and just holds it tight ... but this arouses the son and he starts to move his hips so that you can say he is "fucking her fist". She doesn't do anything, she just holds his cock, the rest is done by the boy. In the end, he comes like never before.

Mom thinks everything is ok now. She thinks he will go out and search for a girl to repeat it.
And yes, the guy wants to repeat it - but why go out and search a girl, when your mother is so open minded ... and then, she is single (or widowed) since quiet some time and she never dates. So the son thinks she needs some cock ... and he is more then willing help her out with his own cock ... so he tries to seduce his Mom
 
More details, please. I mean, when she watches him, does she spy on him ? Or does the boy know that his mom is watching ? Or since you said she is helping him out ... does she takes his cock and masturbate him ?

This would be cool: Mom catches him, masturbating. He is embarrassed, but she tells him that masturbation is ok. Of course, Sex with another person is much better. To prove it, she just wants to show him how it feels when another person touches your private parts (and I mean touching, not masturbating) She grabs his cock and just holds it tight ... but this arouses the son and he starts to move his hips so that you can say he is "fucking her fist". She doesn't do anything, she just holds his cock, the rest is done by the boy. In the end, he comes like never before.

Mom thinks everything is ok now. She thinks he will go out and search for a girl to repeat it.
And yes, the guy wants to repeat it - but why go out and search a girl, when your mother is so open minded ... and then, she is single (or widowed) since quiet some time and she never dates. So the son thinks she needs some cock ... and he is more then willing help her out with his own cock ... so he tries to seduce his Mom

This story's actually a pretty good idea I think. It kind of starts out as helping leading to some boost in confidence in the son, but aimed in the wrong direction. Is a nice twist I think :)
 
Believe it or not, we've had this discussion before, and now there are loads of these stories here! :D
I was thinking why can't it be a school project?
A class in masturbation and hand jobs (all students take part).
This would of course lead right into student/teacher breast message classes.
Then we have parent's day, where the parents (and sibling voyeurs) get a first hand elvoluation of their child's work (all characters 18 and up).

I just thought of something.
If you really haven't masturbated before 18, then these classes are a must! (stupid Lit rules) :rolleyes:
 
another variation with Mom could be: for some reasons, this boy can't masturbate. Maybe his hands are crippled. Or he had a freaky accident, so both his hands are in cast. Since he broke his hands very bad, he has to wear the cast for a few months.

Anyway: he can't masturbate. He really wants to shoot his load, but he can't. After some time, he becomes "wet dreams". So many times in the morning, his bed is full of his cum.
Everytime, Mom changes the sheets, without saying anything. The guy is embarrassed about this. At first he doesn't want to talk about it, but since it is obvious what happened, he starts to talk to Mom about it ...

"I'm so sorry Mom. This all just happens because of my hands. If I could jack off, like a normal guy, you wouldn't have to change the sheets so often."
"Yeah, and I think it would be better for you, if you could jack off yourself. It is totally normal for a guy of your age. If I just knew how I could help you"
"Well Mom, you can help me. You can jack me off"
"No, son, that would be incest. That would be wrong"
"Is it incest if you massage my back ? Is it incest if you rub my leg ? As long as I don't push my dick into you ..."

So Mom starts to think about it ...

I am thinking about it: I guess, if the boy is 17, and Mom gives him his first handjob on his 18th birthday ... this would be against Lit rules, right ? But maybe X-Mas is close and so Mom wants to give him a special X-Mas present ... a XXX-Mas present.
Of course, after a few handjobs, they go further. Mom is tired of holding a handkerchief to catch her sons cum. So at first she gives him a handjob, and when he cums, she opens her mouth, so he can shoot his load into her mouth. Next time, she gives him his first blowjob .... soon after that, his hands are fully healed and the casts comes off, but they keep on having sex ... including vaginal and anal sex ...
 
another variation with Mom could be: for some reasons, this boy can't masturbate. Maybe his hands are crippled. Or he had a freaky accident, so both his hands are in cast. Since he broke his hands very bad, he has to wear the cast for a few months.

Anyway: he can't masturbate. He really wants to shoot his load, but he can't. After some time, he becomes "wet dreams". So many times in the morning, his bed is full of his cum.
Everytime, Mom changes the sheets, without saying anything. The guy is embarrassed about this. At first he doesn't want to talk about it, but since it is obvious what happened, he starts to talk to Mom about it ...

"I'm so sorry Mom. This all just happens because of my hands. If I could jack off, like a normal guy, you wouldn't have to change the sheets so often."
"Yeah, and I think it would be better for you, if you could jack off yourself. It is totally normal for a guy of your age. If I just knew how I could help you"
"Well Mom, you can help me. You can jack me off"
"No, son, that would be incest. That would be wrong"
"Is it incest if you massage my back ? Is it incest if you rub my leg ? As long as I don't push my dick into you ..."

So Mom starts to think about it ...

I am thinking about it: I guess, if the boy is 17, and Mom gives him his first handjob on his 18th birthday ... this would be against Lit rules, right ? But maybe X-Mas is close and so Mom wants to give him a special X-Mas present ... a XXX-Mas present.
Of course, after a few handjobs, they go further. Mom is tired of holding a handkerchief to catch her sons cum. So at first she gives him a handjob, and when he cums, she opens her mouth, so he can shoot his load into her mouth. Next time, she gives him his first blowjob .... soon after that, his hands are fully healed and the casts comes off, but they keep on having sex ... including vaginal and anal sex ...
Not that original (nothing really is in this genre), but it's still a really good story.
I think the X-mas present part is going a little too far though.
It could be she intended to do that for him, but had some last minute Christmas shopping to do (including finding a tree and making Chistmas dinner).

I like the Birthday idea anyway.
Imagine making a Birthday wish to get a hand job from your mom and it came true! :eek:
I hope she's one of these young hot moms who get pregnant very early so she keeps her looks when her child is born.

I like your first idea better, but after a good amount of wriggling, she should get a little horny too.
First she strokes the foreskin up and down (best when circumcised), then twists her hand while cupping his balls in the other hand and gently squeezing his sack.

More sessions will take place while she's topless, as her son watches his mom's nipples get hard.
Next is oral sex, where he gets to feel her saliva on his cock as her tongue swirls around it.
At first he's apologetic for cumming in her mouth, and tries to hold it back until he takes it out, but his mom says it's ok and wants to drink it.

Now his hands are better (if he wasn't faking it to begin with), but his mom just can't help herself, and comes on to her son, showing more and more skin each day.
 
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another story idea could be:

Mom wants to walk into her sons room, when she hears a strange sound - someone is moaning and breathing heavily. So before she walks in, she wants to look whats going on inside. Maybe the door is not fully closed (probably Mom came home earlier then usual) or she looks through the keyhole. She sees her son sitting naked on his bed, masturbating while he looks at a porn mag. She keeps on watching him, until he is finished. Then he puts the mag back into a drawer and puts his clothes back on. Mom quickly leaves the house. Her son doesn't need to know that she came home earlier.
She drives to a remote parking lot to think about what she has seen. She notices that she becomes horny - so she masturbates, too.
Later, she arrives at home at a normal time. When her son is out of the house, she walks into the room. She is curious about the porn mag that he hides. What kind of porn does her son prefer ? Big boobs ? Small boobs ? Shaved ? Hairy ? Anal ? Asian ? Or maybe even gay ?
She is surprised to see that the porn mag is about mature women. She flips through the porn mag. Some of them are shown solo. But there are also others that are having hardcore sex - with youngs guys. Judging by the age, they could be mother and son.
Some pages later, there is chapter where readers can request special pictures. Like this one guy called Harry. There is even a small photo of Harry included. He wrote "I want to see a mature lady being sandwiched by identical twins that could be her sons." Next to this request, there is a picture, of a mature lady having sex with twin guys.
She turns the page - and is shocked. There is a small photo of her son. She reads what stands next to the photo: "Hello. I love your mag and whenever I look at this mature ladys I become horny. I wish my Mom would pose like that. But I know she never will. So can you please show me a picture of a redhead curly woman in her mid 40s, with big boobs and a shaved pussy ? She should be wearing only stockings, a garter belt and high heels. That way I could imagine she would be my mother.
Next to this request is a photo of a redheaded woman in lingerie. It is obvious that her son jacked off while watching it, because there are cumstains on the paper.
However, the woman looks very different then her. Her boobs are too small and the hair is straight - not curly, like her own.
But still, the idea that her son masturbates while he thinks about her makes her horny again. And she decides: why shouldn't she do him the favour. Instead of jacking off to a photo, he should get to see the real thing. So she goes out to buy stockings, a garter belt and high heels.

The next day, she knocks at her sons door - wearing only stockings, a garter belt and high heels ...
 
<snip>
But still, the idea that her son masturbates while he thinks about her makes her horny again. And she decides: why shouldn't she do him the favour. Instead of jacking off to a photo, he should get to see the real thing. So she goes out to buy stockings, a garter belt and high heels.

The next day, she knocks at her sons door - wearing only stockings, a garter belt and high heels ...

Another way...
One night after dinner, she loads the dishwasher as the son watches TV in the living room. When she's finished with the dishwasher, she goes to her room. She comes out wearing a thick, oversized robe.

She yells down the hallway that she needs to talk to him in his room. When he gets there, she gets out the magazine. "So you like looking at old ladies?"

"Not old, Mom. Mature. Real women," the son replies nervously.

"Turn to page 69," she instructs him. He turns to the page and sees that she's circled his request in red magic marker. She's also written "I love you" on it.

She drops the robe, revealing the garter and hose. She looks down at her fiery red bush and asks, "would you like to jack off while I shave it for you?"
 
thats also an interesting one. Another idea could be:

Mom sees that he has more then one magazine. It seems he buys them regular, every month. In this mag, there are also some pages for reader submitted photos. She has no problem with being seen nude. So she dresses up in hot lingerie and takes some photos of herself (with an automatic shutter).

Mom sends the photos to the magazine and adds a note "please release them, soon, I want to surprise someone that I really love, his name is Tom" (Maybe it's a birthday present)

When the next magazine comes out, Mom rushes over to a store early in the morning. She buys it and unwraps it. Then she flips through the mag and - yes, there is an entire double page showing her photos. The photos are titled "This is a special surprise for Tom".

Today she has a day off, so she spies on her son ... in the afternoon, he goes to the shop and comes out with a wrapped magazine. It's obvious what kind of magazine it is. The son goes home, into his room. He believes he is alone, so he is getting naked and unwraps the magazine ... while his Mom watches him through the keyhole. Quickly, she drops her clothes - underneath, she wears the hot lingerie from the photo shoot.
The son is slowly massaging his cock while he is flipping through the magazine. He is not jerking off yet, he wants to see all the ladies and jack off to the best. Suddenly, he freezes. He stares at the page and suddenly he starts to massage his cock like mad. It is obvious - he found the pictures .... Then, Mom opens the door (I guess she didn't knock before opening). She smiles at him and says "no more jerking off - now it is time for the real thing" ....
 
not sure if this is waht you're looking for, but i wrote Masturbating With Mother quite some time ago.

if you read it, pleae forgive the attempts at purple prose and the over-use of adjective. i was younger back then.
 
definately some very delictable stories and ideas in this thread. here is another twise

mom and son are quite close, father walked out on them a few years back. the son grows up to be quite handsome, but always a good kid. son goes off to college and in her lonliness the mother starts going to the internet for some much needed relief. she eventually finds a site where people openly share on webcam. she is obviously quite reluctant to show herself but eventually gets the nerv to point the cam towards her ample cleavage. one evening she meets "collegestud" who praises her for her beautiful breasts. they chat a bit and then she watches him masturbate.

after a few sessions of her watching him, she starts fingering herself, repositioning the cam so he can watch. their conversation obviously turns to his desire for an older woman and he confesses how beautiful his own mother is, but she always hides it and never dated since their father had left. he admits that even most of his friends think she is a milf.

winter holidays come and the son returns home for the break. one of the first night she "goes to bed" early, and finds that collegestud is online and they have one of their mutual masturbation sessions. the next day while doing the laundry she recognizes the boxers that collegestud was wearing in her son's dirty clothes pile - along with a cum stain. she is shocked, goes up to his room while he is out and discovers that he has bookmarked that very site.

she is a bit beside herself, not knowing what to do, discovering that she has been getting off watching her son masturbate for the past month, without even knowing it. that night, again in her room, she is drawn to the site and sure enough, collegestud is waiting for her. she reluctantly surrenders to a mutual masturbation session. afterwards, in chat, she pushes him a bit about his mother and if he desires her - which he admits to. in signing off she tells him to be sure to be on tomorrow night as she has a special gift for him...
 
sounds cool.

The question is: what is this special gift ? Will she show him her face, so he can decide how to continue ? Or will she confront him directly - like when he logs on, she knows that he is in his room, ready to masturbate ... so she walks into his room (dressed in the hot lingerie that her son always loved during the webcam show) ...
 
i imagine she will be at the cam in some very sexy lingerie that she shows off to him. he shows his appreciation by pulling out is very hard cock. then she messages him that she'll be right back as she has more to show him. then she goes upstairs and walks straight into her son's room. he jumps immediately realizing he's been caught masturbating by his mom until he notices that she is wearing the lingerie he just saw online...
 
I had another idea. Not exactly the same, but ...

what about Mom watching her daughter ? The daughter is in her room, playing with a dildo. Maybe she "borrowed" the dildo from her mother, without asking (she only used it, when Mom was away - before Mom came back, she cleaned it and put it back in it's hidden place in Moms closet)

Or, the other way round: Mom sees how her daughter enjoys the dildo, so she wants to give it a try, too. The next time, the daughter is away, Mom takes the dildo and starts to play with it ...
 
i imagine she will be at the cam in some very sexy lingerie that she shows off to him. he shows his appreciation by pulling out is very hard cock. then she messages him that she'll be right back as she has more to show him. then she goes upstairs and walks straight into her son's room. he jumps immediately realizing he's been caught masturbating by his mom until he notices that she is wearing the lingerie he just saw online...

sounds also very cool.

I once saw a commercial for some internet company. You see a boy watching a girl on a webcam. Both can only see their bodies, but not the faces. Both wear t-shirts with unique, noticeable designs. As far as I can remember the girl showed him her bra, or even more ... but suddenly, the boys Mom calls him, because dinner is served. He sits down on the dinner table and starts to eat. Then he looks up and sees his sister, sitting on the other side of the table. She looks up, too - and suddenly, both recognize the other ones t-shirt .... :D
 
I had another idea. Not exactly the same, but ...

what about Mom watching her daughter ? The daughter is in her room, playing with a dildo. Maybe she "borrowed" the dildo from her mother, without asking (she only used it, when Mom was away - before Mom came back, she cleaned it and put it back in it's hidden place in Moms closet)

Or, the other way round: Mom sees how her daughter enjoys the dildo, so she wants to give it a try, too. The next time, the daughter is away, Mom takes the dildo and starts to play with it ...

mom-daughter stories are always quite enticing!

sticking with the internet scenerio, what if the mom, on borrowing her daughter's computer one day discovers a bunch of explicit pics of her. She is shocked and going to confront and punish her daughter. she checks the computer a bit more and is even more shocked to discover her daughter has her own amateur website. in searching around she discovers all kinds of pics - her with other girls, her sucking cock, her with a big black dildo. she then checks her drawers, and sure enough, there is the dildo.

she leaves everything as is, shocked. but she also begins to recognize that her prudish facade is shaken and realizes that she is dripping wet. she can't help but masturbate. back on her own computer she finds her daughter's site and sends her a message asking if she is into older women and how come she doesn't have any pics of her with an older woman. the daughter replies that she is, only she hasn't found any willing participants yet...
 
mom-daughter stories are always quite enticing!

sticking with the internet scenerio, what if the mom, on borrowing her daughter's computer one day discovers a bunch of explicit pics of her. She is shocked and going to confront and punish her daughter. she checks the computer a bit more and is even more shocked to discover her daughter has her own amateur website. in searching around she discovers all kinds of pics - her with other girls, her sucking cock, her with a big black dildo. she then checks her drawers, and sure enough, there is the dildo.

she leaves everything as is, shocked. but she also begins to recognize that her prudish facade is shaken and realizes that she is dripping wet. she can't help but masturbate. back on her own computer she finds her daughter's site and sends her a message asking if she is into older women and how come she doesn't have any pics of her with an older woman. the daughter replies that she is, only she hasn't found any willing participants yet...

the idea of the borrowed computer is very cool. Especially the part with the amateur website. Nowadays, many amateur girls have their own porn website. It could be like: Mom knows that her daughter is interested in taking photos - so she asks, if she could take some pictures of her. At first the photos are normal, but then, Mom says she also wants to pose in lingerie. Daughter is surprised but gives in. Suddenly Mom asks her daughter if she knows someone who knows how to code html, because she wants to do her own website - with erotic pictures of herself ...


Another idea could be: Moms computer broke, so for a few days, the daughter gave hers to her mother. She told her: In case someone sends me instant messages through ICQ, you can reply them. You can tell them that you are my Mom, or you can make fun of them by pretending that you are me. This would be funny.

So some time later, Mom is online, when suddenly an instant message comes in from a guy ... Mom wants to make fun of him, so she pretends she is her own daughter. It is obvious that the guy is familiar with her daughter ... but after some time, the chatting becomes more and more erotic.
Mom becomes really hot and finally she masturbates. The next day, this happens again. Mom becomes more and more curious about this guy - but also she would love to have real sex with him.
She asks him for a date ...

The interesting twist in this would be: who is this guy ? Just a normal friend of her daughter ? Maybe a relative of her daughter (like her own brother - at first he has a sexchat with his own sister and then with his own mom ? No, forget that, too unrealistic) Or maybe it ain't a guy at all - it is her own daughter who wanted to make fun of her ... but now, the daughter also became horny
 
well, we have definately expanded the topic of this thread!

woman with a son marries man with a daughter. the girl is spoiled, beautiful, and quite the bitch. she is also intensly jealous of her stepmother and stepbrother who her father is bending over backwards to be a father to. she hatches a plan to ruin them and have her father kick them out of the house.

She knows from time to time her stepmother goes online and chats with some of her friends. one afternoon, pretending to be a young guy she starts chatting with her - very casual, very friendly. she also starts chatting with her stepbrother, pretending to be an older woman. he obviously gets quite turned on and starts chatting her up.

things heat up between the stepmother and her supposed online young guy friend, who is really the stepdaughter. the "guy" says he wants to get on cam for her. simultaneously the stepdaughter is chatting up her stepbrother, in the guise of an older woman, and asks that he goes on cam and shows her his cock. which of course he gladly does. in some technical way, that i have absolutely no idea about, the stepdaughter has the sons cam show on the mothers computer. she immediately recognizes his room and stops, shocked.

not knowing what to do she walks down the hall into his room. the original plan of the stepdaughter was to expose their incestuous relationship. however, in seeing her stepbrother's cock she starts to get a turned on. she then decides to go across the way to her stepbrother's room and in she barges finding the mother and son half naked kissing. they freeze seeing her. rather than walk away to tell her father, she joins them... or does she?
 
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