>be me, 24m, wage slave >work with milf/cougar >50-ish,

>>39447782
Ask her if she's married. If she says no, try to casually ask her if she's been laid in a while.

>>39447802
She is but he's a dick and I'm pretty sure she's a slut.

>>39447821
Then try to just bring up a sex conversation without trying to sound like a creep. If you have a big dick, and lots of stamina, let her know that.

Just like you would any girl, and you'll probably have to try harder than with a girl your own age. It's a myth that cougars are out looking for young men to fuck. They know their light is fading and have virtually no time to find a stable career man that will save them from the drudgery of work.

>>39447782
Oh yeah and she hates confrontation, so I am not above bullying her into it cos apparently I'm a dick lmao

>>39447847
That is going to take some serious tact, I will have to play the long con.

Damn you, unrelenting immediacy of lust.

File: 1503090599986.jpg (22KB, 320x320px) Image search: [Google]

22KB, 320x320px

>>39447927
Alternatively you can rape her

>>39447972
I said I'm a wage slave, not a college athlete.

>>39447847
What if I have a really small dick and no stamina though?

>>39448041
You will be bad at sex and nobody will fuck you because women talk about that shit to each other

>>39448061
Well then I'm screwed :D isn't it a cruel joke to make me tall and handsome with good facial bone structure but give me 5 inch penis and premature ejaculation?

>>39448179
5-incher ain't that bad. Any lower and I'd say you're pretty screwed but the US average is like 5.5 anyway. It's nothing to look at but below that you're starting to run into "can't actually make good secks due to physical limitations" territory.

The PE is something you can work on, probably by not being a pathetic loser who jizzes his pants when thinking about MLP.

>>39448241
but I'm not from the US I live on Iceland lol

I don't like cartoon ponies, I jizz my pants only when thinking about impregnating girls

which is too often. I don't know how to work on this

>>39448265
>I don't know how to work on this

Leave your parents' basement for an hour a day.

>>39448280
but I don't even live at home :p also feel embarassed because girls expect me to be hung and if they see what's really going on down there maybe they will make fun of me

>>39448370
just fuck em in the ass anon

>>39447782

Start by not fapping before shifts so you keep getting those boners. Make your bantz gradually more and more lewd until you get to the point where you can make some kind of joke about getting a boner and point at it.