You are asking this question on a board populated by men and women who use money as a conduit in order to AVOID exactly the trouble that you are asking for...

My best advice would be to just dive in and have your fun...just plan ahead and have the number of a good divorce lawyer ready!

You could wear your ring on your dick, and if you still have the money, everything will be fine.

I'm not entirely comfortable with that statement, but it's pretty damn true!   Well said!  Just the way the world works...

Charlie Sheen was once asked why he paid women for sex. He replied, "I don't pay them for sex, I pay them to leave." The wisdom there is that hiring an escort for your extramarital or recreational affairs is easy, clean, simple, and has a finite beginning and end. Once you remove the business nature of that relationship, it has the potential to get really messy. What if she falls in love with you? And you with her? Are you prepared for that? All the complications of a relationship, but treated with your part-time attention because of your wife and family will simply end with her hurt feelings or your resentment towards your current partner. IMHO, simply not worth it.

my advice only having done this a few times is that it's best to be honest with the gf - though of course not with the wife - the gf has to be cool with stealing you away from another woman - some girls love it. the girls who are not into it can destroy you if they find out you're lying to them. so show your balls, wear the ring, and play the way you feel it - you both know you're cheating, but you prefer her over what you have at home.

second tip - keep it short unfortunately. the longer you go the more she'll feel like she's wasting time with you - or will feel like she deserves you more than your other girl - it's just gotta stay as two people having fun. it's hard, but after a few months or so, you just have to cut it off - yeah i know cutting off free sex - but know that you got game and you can find another one - or another one can find you - soon enough.

t/c