I really enjoy this sub and I think it’s time for me to contribute one of my own stories. Sorry if some of the grammar doesn’t sound right, as englisch is not my native language.
This all occured around 8 years ago when I was in my early twenties, still studying and single.
As I didn’t have a girlfriend at that time and Tinder wasn’t really a thing at the city I lived in I was hanging around in a lot of chatrooms trying to flirt.
Most of the time I wasn’t looking for a hookup or anything serious but for girls that would skype and masturbate with me.
This wouldn’t work most of the time but sometimes I got lucky.
To start the story I got lucky with a girl, let’s call her Amy, and damn she was hot. Way out of my league as she was only 18 had huge natural breasts, thin hips and cute round butt.
She had lang brown hair and one of those resting bitch faces, which was kind of my kink at that time.
But I could tell she wasn’t quite into masturbating together but really liked the attention she got from me as she showed me her body.
One time when Amy wasn’t online I scrolled through her profile and looking at her pictures I stumbled upon one where she’s next to her mother. Which was kind of uncommon on this site so I didn’t think it was true.
Curious as I am I went to her mom’s, let’s call her Mary, profile and I could confirm it’s her as she didn’t really had a lot of personal information on it but pictures with her daughter and only liked her fanpge. (Yes Amy had a fanpage, don’t ask why I guess because of attention).
To describe Mary, her face looked a little similar to her daughters but she had short blonde hair and I guess she was in her mid 40s, but not that classic milf-look, more like the usual neibourhood mom.
Not thinking too much about it I send her friend request, which she accepted a few days later.
About a week later Amy chats me up to call. She sounded pretty mad so I asked her what’s up.
Amy: So you’re now friends with my mum?
Me: Yeah I saw her on of your pictures.
Amy: So you think she’s hotter than me?
Me: What no? I just was curios if it’s really your mum.
Amy: Well let me remind you how hot I am.
And wow how hot she was. This was the hottest time we ever talked to each other she stripped down completey naked stood infront of a mirror and startet touching herself. All that while telling me how she loves my dick and what she would do to me if I were close to her.
I could clearly tell that she was just jealous of her mom but I didn’t care one bit.
Unfortunatelly this didn’t repeat a lot but as you can imagine I tried to call her up a lot. One time she answered but told me she’s busy because her mom was right next to her.
So there I was lying naked in my bed with my dick in my hand and frustrated that I couldn’t finish with her. When I hear her mom say
Mary: Who are you talking to? IS HE NAKED?
Amy: Yeah that’s the guy that you’re friends with. You wanna see?
Mary: Sure why not. Oh that’s a nice cock.
I was so shocked I froze for a bit. My first reaction was to hide but seeing them together interested in me was quite a turn on.
Looking at their faces I again started to strocke my cock expecting they would turn away or hang up any moment. But they didn’t. They watched me and her mom giggled a lot as Amy gave me her sexy eyes. It dind’t took long for me to finish and I could tell from there faces that both quite enjoyed watching me.
I hope you enjoyed reatind this as it’s one of the most interesting and funny sexstories that has happened to me.
For anyone whondering this never happened again. But I did masturbate with both of them seperatly multiple other times. But I’m not currently in touch with neither of them. Last thing I heard Amy had a baby.
Source: reddit.com/r/gonewildstories/comments/qq38aw/that_time_i_m_masturbated_for_18_year_old_f_and
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You get extra man points for masturbating with Mom!
This is another fantasy of mine