OP here.
I am repulsed by it because:
1) it is rather sickening for a woman to be paying for a man. Out of pity, I did it with most of the men I dealt with in my life, but it went against my nature as a woman. I've done it too many times with men (whether they be friends or boyfriend) and it has now come to nauseate me - because the man is supposed to be paying for the woman, not the other way around.
2) the money I give my friend is usually me cleaning up the messes he gets himself into. For instance, if he had not procrastinated about paying the registration on his RV, he wouldn't be in this mess. If he had listened to my advice by distancing himself from the bounty hunter friend, he wouldn't be owing him (instead of distancing like I told him, he goes and borrows money from him).
3) the money I give my friend sometimes goes to waste either because another problem arises right after (because of his incompetence) and or because he does not keep the promise I made him take on the condition that I give him the money.
For instance, a few months ago, I gave him $700 to get dentures (since the dentist pulled out all his teeth). Well, he never asked the doctor the right questions, so he thought it was $700 for the whole set. But it was only $700 for the upper dentures. So now my friend can't even wear the top dentures I bought him because he doesn't have bottom ones. And if he had gone to the dentist all those years I was harrassing him to take care of his teeth, then he wouldn't have even needed to get his teeth pulled out in the first place and I wouldn't have needed to pay for the dentures (but he was afraid to go to the dentist). On another occassion, I gave him $6000 for downpayment of a car on the condition that he promise me something. Come to find out that he succuмbed to weakness and did not keep his promise (which I wouldn't have given him money if I knew he wouldn't have fulfilled his promise). On top of that, he was eventually unable to make payments on the car and they repossessed it. So there went my money down the drain.
But mostly, it is #1 that is a reason I am repulsed. Considering the fact that I have paid for most men I've had interaction with, I've come to be repulsed by men who let a woman pay most of the time.