I used to be really penis shy. I'm not sure when the transition started to happen, but at some point I really began to appreciate my size and have better orgasms. Actually, now that I think of it, it was when my partner started to travel a lot, so I had much more quality alone time.
I'm also lucky enough to be a shower and a grower. Browsing tumblr (cry) helped me develop a taste for bulges, freeballing, and showing off a bit. So, I started my own play in that area. I'd go out for my hikes wearing UA shorts, and the combination of sun on my cock, it flopping around in a semi state, and looks of appreciation from passersby, really made me enjoy what I had. It was empowering on a level, and great for self esteem.
I'm 7x5, which I'm told is a great size. Not too big, but largish. I also have a nice plump head, and decent sized balls. When I'm out wearing shorts at a coffee shop, I can opt to be conservative, or let it hang to a side to give someone a good show.