Jesus.. countless. I got into escorting in my early 20s. I got in shape for the first time in my life so I had a ton of new confidence, a thin waist, great hair, and a bad fuckin attitude.
But before I lost weight at 21, I spent 2 years letting older guys (men who are my age now, 30s, but up to the 50s) blow me because I just fucking LOVE getting head (especially GREAT head, and older gay men are the best cocksuckers in the universe, and always will be).
And these guys LOVED my cock, and my balls. I was 18-20, not especially large, but it's pretty and thicker than average, with low hanging big balls (which I love having licked and sucked on almost as much as my cock).
And once I realized that I had a cock that guys really wanted to suck, I then only let the best cocksuckers who also provided weed have it.
And then I used craiglist to get paid moderate amounts of cash to let guys I wasn't attracted to blow me, which I had already been doing for years, and so my cock pics were all over the internet and craiglist for years.
I'm still not exactly shy about showing my cock pics.. even to male or female friends if they're curious. I'm proud of it.