How can I hit on an older woman?

[CodeBreaker]

Tell her. She'll let you know immediately whether she's dtf or not. Older women are great. Ditch the games.

What if I offend her when I tell her?

 

[CodeBreaker]

How old are you talking about. 50, 60 or older?

Lol. 30-45

 

[ralphc1]

I have this fetish for milfs or cougars. How can I get one?

There's this supervisor in our office that likes me, but treats me like her son. So I don't know if I should do something about it.

Lot's of alcohol is the key.

Candy is dandy but liquor is quicker. - Ogden Nash

 

[squeezewax]

Well, many years ago when i fancied a particular older female, i simply said, ' i was wondering if you'd like to have sex?' She didn't hesitate in the slightest, she said 'sure.' And we did it!
She was, and possibly still is, Spanish.

Around a decade or so earlier, i asked my auntie the same thing. We ended up having a 9mth relationship. I was 17 and she was 36.

 

[CodeBreaker]

Well, many years ago when i fancied a particular older female, i simply said, ' i was wondering if you'd like to have sex?' She didn't hesitate in the slightest, she said 'sure.' And we did it!
She was, and possibly still is, Spanish.

Around a decade or so earlier, i asked my auntie the same thing. We ended up having a 9mth relationship. I was 17 and she was 36.

Lucky ass. Wish I could get one

 

[Strychnine]

Not bragging but in terms of looks and charm, I think I have it. People often compliment my looks, and I do modelling

You're on Sherdog, bro.. We all do modeling, bench press 400+, and nail supermodels on the reg.

 

[tonysmasseuse]

So, what happened CodeBreaker - did you make any progress yet?

 

[Dusty Rhodes]

Here's the key to picking up a Gen-X chick. Turn your hat around and sag you oversized pants then walk up to her and say "Bawitdaba da bang a dang diggy diggy diggy said the boogy said up jump the boogy" say this six times (6x). This puts them in a trance. Then say "My name is KIIIIIIIID, Kid Code Breaker."

Lmao had to go back to the first page to see if TS' user name was Code Breaker - and it was. Thank you for that

 

[mrln242]

I have this fetish for milfs or cougars. How can I get one?

There's this supervisor in our office that likes me, but treats me like her son. So I don't know if I should do something about it.

Its pretty easy, older hoes are into younger good looking dudes. If you are good looking just be smooth and bang!

 

[CodeBreaker]

So, what happened CodeBreaker - did you make any progress yet?

There is. We are now talking even at night, chatting on Viber


Before, we only speak to each other in the office

 

[pinger]

Around a decade or so earlier, i asked my auntie the same thing. We ended up having a 9mth relationship. I was 17 and she was 36.

Wait Wut?

 

[breadfighter]

Wait Wut?

 

[Phlog]

What if I offend her when I tell her?

She's in a position of power so it's unlikely that she would feel threatened. The only way it becomes awkward is if you let it. You could just start complimenting her, ask if she has a boyfriend, that is pretty obvious and gives her an out if she wants it without you actually asking outright.

 

[Twelve75]

I can co sign all of this, I had some really good experiences with older women in my 20's..

how old are you know ? the whole MILF & Cougar labels weren't invented when I was in my mid 20's and to be honest, I really never hung around anyone that was interested in older women, to be fair, for the most part, a 40 year old woman in 1995, had a far different attitude and outlook compared to one today.

 

[squeezewax]

She was my auntie by marriage, not by blood.

I've always found that if you can make a female laugh a lot, then you are just about certain that you're gonna have sex with her.

 

[lowlife]

how old are you know ? the whole MILF & Cougar labels weren't invented when I was in my mid 20's and to be honest, I really never hung around anyone that was interested in older women, to be fair, for the most part, a 40 year old woman in 1995, had a far different attitude and outlook compared to one today.

I'm 38 now, was in my 20's in the 2000's. As far as I know the term cougar has been around forever, but indeed women mature much differently, on the whole, than they did 30 years ago.

 

[Twelve75]

I'm 38 now, was in my 20's in the 2000's. As far as I know the term cougar has been around forever, but indeed women mature much differently, on the whole, than they did 30 years ago.

I have almost 10 on you bud, but for drunk women at office parties at Christmas, the older chick/younger guy thing was never something my friends or I really every encountered,or desired, looking back though, jesus, ''Big Lynne'' would've been a memory I would have took to my grave, if it went as far as clothes on a bedroom floor, still what I remember to this day, is hearing my voice say...''fuck off lynne, you're annoying me''......{big as in tall}

 

[CodeBreaker]

Update:

She just brought me breakfast this morning

 

[Sir Galahad]

Lol. 30-45

One of my first sexual experience was an older black woman who gave me a blowjob. I didn't get to fuck her but when she swallowed me whole I came too fast.

 

[CodeBreaker]

One of my first sexual experience was an older black woman who gave me a blowjob. I didn't get to fuck her but when she swallowed me whole I came too fast.

How long? Like 2 minutes?