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[ most older women have a fantasy...at least from what i have found...to be with a younger man.
Here's the problem with mixing this situation up with that fantasy:
That fantasy: To have hot sex with a gorgeous (I'm talking Leo Dicaprio) 20-something who can go all night and disappear shortly after.
This situation: Having sex with a cute 20-something who is going to be lurking around your BFFs place, brag to friends which could be overheard by your BFF and essentially guarantee that it will get out to your BFF and your entire social circle and while it's fun when he has no connection to you, doing your BFFs son is kind of like doing your nephew. Gross.
I'd say don't do it. You're looking to open an can of worms and, if the woman has any smarts at all, she won't do it.
Cinnamon
Half naked doesnt cut it...
as for the post, cinnamon did bring up some good points i failed to mention. Trust and maturity...if she thinks for a second your going to go around and tell everyone and your mom (litterlally) that you two are together she will drop you like a tampon after a period. Keeping it a secret only the two of you know...now thats erotic
shes not going to go for any young guy that is going to bring drama, she will go for a young guy that is mature enough to handle a trist.
now as cinnabun said, if things get out...the can of worms you open will do massive dmg, to either you, her, your mom or everyone involved. If you cant handle is, dont go for it. You do the actions be able to handle the reactions.
me personally...i would go for it, but i know i can keep my mouth shut.