Has this ever happened to anyone? Your playing chess with someone, you play 20 or so 2 or 5 minute games, kill about 4 or more hours and think, I had such a great time, I am almost tempted to pay this person for a similar session 1 or 2 times a week. Has anyone actually gone ahead and carried out this idea, or do they know of it actually being done on this or maybe even another chess site? Is this too absurd an idea to even consider??

If you want to pay someone; I'd imagine you can 'Google' some 'master' advertising their services, under the googled: chess tutor.
 
- And I found this link {see below.. and one of several}; By having googled: Play {'online'<- optional}, chess for money. -- Ps. My 'advice' is Free; And I wouldn't have it any other way! .. And given my blowing 'hot & cold' chess talent; For myself, that chess $$ option doesn't come into consideration. -
http://www.playe4.com/playing-chess-for-money.html#main1

wow! I never knew such a site existed. I remember playing on Moneygaming.com and you could play just about any game for any sum of money. I know what you mean about playing for cash, but consider playing a player who is not a MASTER, just someone close to you in strength! The people who have the most fun at chess , I have heard, are the ones who are closest to each other in strength. That might be worth cash! Anyway thanks BUZZKILL.

I will gladly supply pay pal info if anyone would like to purchase some points and get a big laugh while taking them from me.
 

ha ha ha , I will consider this RAPTOR, thanks!