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My Mom’s Hot Friend

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Thread replies: 9
Thread images: 1

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Posted this back in December last year but need more advice.

>28 m here
>Just got out of a long relationship
>Go to my mom’s christmas party
>See her hot cougar friend from work is here
>We start chatting a bit
>She seems tipsy
>She starts getting really close to me
>I put my arm around her and we just continue talking and having a good time
>Mom comes over and I can tell she’s annoyed with her friend
>Cougar starts making jokes how she’s going to be my mom’s new daughter in-law
>Mom is triggered and I just walk away from the situation
>End of the night, about to leave, see cougar by herself
>Go up to her and ask if I could give her a call sometime
>She writes down her number for me and gives me a hug

>Couple days go by
>Get back from bar with friends one night
>Feeling lonely and horny
>Remember I have Cougar’s number
>Text her and ask if she wants to get a drink
>Says she’s tired
>It was kind of late so I understand
>Haven’t texted her since
>>
(Cont.)

About a month ago:

>Go to mom’s office to take her out to lunch
>See Cougar, haven’t seen her since that christmas party
>She’s looking good
>Reminded that I want to fuck her
>Chat to her a bit
>Made her laugh a couple times
>Gives me a hug before I leave

I feel weird just asking her out for a drink sometime, but I would love to be able to have an older woman as a fuck buddy.

This lady has known me since I was about 17 and I used to jerk off to her back then. It would be crazy if I actually got to have sex with her.

She’s a good friend of my mom’s and has been at random family events before in the past. So my question is; how do I engage in casual sex with this woman without making it awkward?
>>
>>18443108

There's no fucking way you can do it and have it not be awkward.

Even worse, is she married?
>>
>>18443106

Oh it's this thread again, only this time OP decided to include details and a story to make it seem like him wanting to bang someone much older than himself is legitimate and has a possibility instead of it being a random request for us to help him figure out a way to get a woman over 50 who is his mother's friend to have sex with him.

>casual sex
>not awkward

By doing it casually.
>>
>>18443108
How was the hug? How long was it? What kind was it? I think you have better chances when the woman is shitfaced like we all do. Anyway pics of this cougar OP? Would really appreciate some.

Back on subject when she hugged you did she lean in a lil extra so her tits are pressing against ya? Did she moan or hum when she did it?
>>
>>18443124
there is, it's called ZFG.

I say go for it, anon.

I have, and I don't look back.
>>
>>18443124
Nah, she's not married.

>>18443126
I guess I'm just going to make it weird anyway.

>>18443153
I mean it was a pretty casual hug, she did press her titties into me though which made me think "hmm?". No pics yet, not going to be a facebook creep.

>>18443173
Thanks. I think I will. Fuck it who cares anyway right?
>>
>>18443108
It's only awkward if you make it. Act casual and treat her as you would before you slayed that cougar puntang
>>
>>18443205
just keep it under wraps; if she's any way smart, she won't let on to your mom, otherwise she knows she loses both the D and her friend.

you've got nothing to lose by sending her some non-committal messages to see how she responds [maintain plausible deniability]. if she bites, you go for the jugular and ask her out for a drink. after that, you know what you're in for.

let it be your little secret, but don't go mushy on her. you're both in it for the ride. you'll learn a lot from this experience.
Thread posts: 9
Thread images: 1


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