Ever since I could remember I wanted to be fat. I was discouraged from doing it from my parents.
When I moved out on my own, I tried gaining a bit of weight - about 30 lbs, but the experience was pretty negative. Part of it was my fault - I was eating a bad diet in order to help me gain. Lost the weight, figuring that the reality was too different from the fantasy I had in my head.
About a decade later, I was presented with the opportunity to try it again - and gained slower and with my health more in mind. The funny thing was, when I got up to 300 lbs, I didn't really feel that big. So, decided to let myself gain more.
Got to 350, still felt small, and kept going up in increments.