I don't know if that has to do with my failed love life with women.

But I'm beginning to think that it's less about the penis and more about a masochistic desire to feel inferior to my partner.

It sounds like you're depressed (not medically, I'm not a doctor) and have fallen down a porn rabbit hole. You should take a break from porn for a long while, and work on whatever makes you happier outside of these quite negative thoughts.

It's fine to be sexually interested in being submissive/women's clothing etc, but it is not a reason to transition. Tons of people have healthy sex lives incorporating these elements without being trans. It's also very important work on developing a healthy sex life - one where you aren't thinking about sex and porn all the time.

Finally, try to consider how you'd feel about being a woman if you didn't get to have a woman's body, or a woman's body that you don't find attractive. There's a lot more to being a woman than being pretty.

I hope you do alright. If you take one thing from this, then let it be this; stop watching porn, especially that kind of porn.