I have gone through kinda the same phase as you iSnare, but at a slightly different route.
My small penis self esteem actually began within my family. I have heard through all of my childhood and beyond, that big penises runs in the family. My father has one, my brother has one, and a few scattered back the bloodline has them. So, when I went into my teen years with “only” 6.5 inches, which didn’t grow, I knew that it wasn’t enough. Why would my family been so proud of big penises if it wasn’t something to it? To add to it, I connected my brother and my fathers popularity among women with big penises.
The insecurity grew further when I started to join sexual communities at 18-19 years of age. EVERY SINGLE WOMAN and couple wanted to meet guys with a minimium of 8 inch, preferably larger. The gathered insecurity was impossible to fight, the evidence was too strong. My insecurities didn’t really go away before I reached my first goal at 7.5 inch.
with the right approach of therapy, I might have snapped out of it. But I choose to terminate the problem instead of accepting it, (As I still today see the perks of a bigger unit) and I haven’t looked back since.