I've never actually hated my equipment, but -- I did not know what gender I was or that gender was a thing until I was about five years old. I spent a lot of time trying to tuck it when I was between 10 and 15 years old, I think.
When I was a teenager, becoming a girl was in the realm of science fiction and fantasy. I did not learn that transitioning was possible until I saw Renee Richards on the TV news, that must have been 1980 or 1981, and I was 18 or 19 at the time.
By then, my equipment had become a source of solitary pleasure, if you know what I mean, one that I used a lot to escape the dismal reality of my life.
My feelings now? Let me put it this way. A few years ago I saw this Filipino guy on TV who had two extra legs growing out of his stomach, and part of a skull with hair on it. It was an undeveloped siamese twin, and because he had it on him, the extra burden on his heart was slowly killing him through congestive heart failure. Yet he did not want to undergo surgical removal of the twin, because it had been a part of him his whole life and he thought of it as his brother.
I kind of feel the same way about my equipment, now that I've lived with it for 52 years. I'm ambivalent. I don't like it getting in the way when I wear panties, and tucking it in order to wear a bikini is a pain, but it's a part of me, and an important one at that.
At the same time, I don't like being a man, and I only feel "right" when I am wearing women's clothing. So I am transgender. But how far am I going to transition, and what I'm going to do with my dingaling, I don't know. I'm not in a hurry to figure it out, though.