When I was about 8 years old and my brother was 3, he received a pretend shaving kit for his birthday. It was just a can of shaving foam and a plastic "blade" on the razor, which just gently scraped the shaving foam off the skin making it look like you're shaving.
I was so immensely jealous that my 3 year old little brother got to "shave" and I didn't. I asked my mom if it would be okay if I tried it just once, and she said "okay, go put some shorts on and you can sit on the edge of the bathtub". I was like "why do I need shorts on, and also, I won't be able to see in the mirror from there!" And of course my mom is like "well girls shave their legs, not their faces". I was ashamed and felt like it was wrong that I wanted to shave my face, and I also felt that it seemed wrong that I was "a girl" but my mom said I was, so she must be right, it must be *me* who was wrong.
I can't remember what I said, but I know I didn't shave my legs with the toy razor. I just let it be. I remember the whole rest of the time that he had that toy (pretty much just until the can of shaving foam ran out) every time I saw it sitting on the edge of the tub I felt jealous, ashamed, and angry. I often thought "maybe I'll just shave my face with it and not tell anyone, I'll just try it once" and I'd get all excited, but every single time, I chickened out before I even picked up the can of foam. I didn't want to get in trouble, but even worse, I didn't want to be "weird" for being a "girl" and getting caught shaving my face.
In junior high I started shaving my legs and pits because I was desperate to fit in and I was already really hairy by then. I didn't necessarily enjoy shaving (I kind of resented it actually), but I wanted to "do well" at being a "girl", and fit in. By the time I was an adult I absolutely hated shaving, and would rather wear pants in summer than to have to shave. When it would get really bad, I'd break down and shave, usually at the prodding of my significant other at the time.
In the past year or so, I gave up shaving my legs pretty much entirely. I even wore shorts with unshaven legs, because I'd finally gotten to a point where I just didn't give a flip what people thought. I still shaved my pits "for hygiene", but I was finally *free* from the pressure to shave my legs.
When I came out to myself (and my current partner) as trans, I at first said "I don't want to shave my legs, but I'll still shave my pits. It might not be forever, but I'm still comfortable doing it for now". A couple months later, I just stopped shaving them. I didn't really think it out or announce that I'm not shaving them anymore, I just kind of "forgot" to shave them, and then just figured "yeah, I think I'm done with that".
Shortly thereafter I started shaving my face. I tell ya, the first time I shaved my face, I got teary after. It was such a fulfilling moment, to watch as I dragged the razor over my foam-covered face, to wash the residue off and feel the smoothness of the skin without peach fuzz all over it, to put on aftershave that feels soothing and smells masculine. And then a couple of days later to feel that "baby stubble" feeling of the peach fuzz growing back... It was amazing. I know it's not going to give me more/thicker/darker facial hair. I know that it's hard on my skin which hasn't been toughened by T like when men (and transmen on T) shave. But the act of shaving my face, the feeling afterwards and the resulting "baby stubble" are all TOTALLY worth it.