524first

Great responses guys! Being a sugar daddy is a bit more complicated than I originally thought... I think I'll stick to being a well tipping client for now.

I was just recently in a situation with a lot of similarities to that. It started out well but after a while, he was frustrated that he wasn't going anywhere, and said he needed someone who would push him more. I'd done a lot to give him a base where he could push himself, but pushing other people as opposed to supporting isn't my style, and he seemed to need that. He's off on his own now, not sure if he's going to live up to his potential or not.

I have been on both sides of this coin. Early in my college career as an impoverished student, I had a wonderful arrangement with a banker with whom I enjoyed frequent weekend trips out of town, all expenses paid by him. He was French and very interested in American culture. In my youthfulness, I taught him a lot about spontaneity and eagerness while he taught me patience, expanded my horizons, and taught me to kiss like the French. Our time together passed far too quickly and I graduated college, but with deep appreciation for him and out time together. He purchased an expensive fragrance for me (that I still wear now some 30 years later) as a thoughtful sentimental gesture of something to remember him by which I do to this day.
 
Now in more recent past, I met a cute young man at a Barnes & Noble who I found was also running an escort ad in a city I frequent on business. He was thoroughly mired in debt and living on a friends sofa. We had initially some great times in bed and out, but all on the clock and tab. Eventually, he initiated wanting to see me whenever I was in town, regardless if it was beyond what I could afford for his escort fee. We settled on a mutual agreed amount for our times together with perks for shows, trips, and gifts that came his way. Less than 90 days into it and following a trip to the Carribean, the sex stopped, his behavior changed, and his resentment at his day to day situation versus when with me drove him to anger and the end of our arrangement. It wasn't healthy for either of us, and I wished him well.
 
Haven't repeated since.

Thanks BaronArtz. I've been having a dialogue with a friend who has a fairly new relationship with a working boy. The boy made comments about looking for a sugar daddy and my friend has been trying to get his head wrapped around that. I suspect (hope) that my friend will read this.

I have. It was fun when it lasted and it inevitably came to an end. As most of these relationships do. Sugar daddy relationships don't really work because of the inherent conflict of interests. The 'son' always worries that the 'dad' can discard him at any time when somebody hotter shows up. The 'dad' worries that the 'son' is just staying in the relationship because of the money. Exclusivity issues can be problematic. Will 'dad' and 'son' live together, or separately? There will be real heart break when one party sees is as a quasi-marriage and the other party sees it as a short term arrangement. My advice: don't do it. Except if you both know/agree it is a short term thing. Or if you are really in love and are getting married.

I always add years to my age. When you shave your age or tell the truth, people say you look like shit. Add seven years, and everyone says you look fabulous for your age.

I'd you rather you just shave your balls.
 
Kevin Slater