Well, while my experience with street-harassment hasn't been as bad as yours, I have indeed had guys asking me to smile for them, randomly stalking me for a block or so, and saying "hey" to me in a creepy way. And it almost always happens while I'm walking through lower-income sections of a city. There was this one group of guys who seriously wouldn't leave me alone while I was visiting Washington DC last month, and it was only when my mom finally walked with me that they stopped.
In my case I'm still not sure whether it's because they actually find me attractive or whether it's because they're clocking me as trans, I've been getting really mixed signals there, but yeah... as my ex Jenny said, "welcome to the world of women."
I guess what makes it scary for me is just knowing that I have almost no upper-body strength and no self-defense skills whatsoever, so if I ran into the wrong person, I'd be up s*** creek without a paddle. It's not easy feeling subordinate in terms of strength and social status. I do get afraid every time I'm walking somewhere alone.
But on the other hand, there's also the trade-off where people don't automatically perceive me as a threat anymore. That is like the #1 thing that I hated pre-transition socially, was that people, women especially, seemed scared of me for absolutely no reason. They were always quick to get defensive, unpersonable, almost as if they were automatically scared of me and emotionally closed-off just because I was male. Where now, people automatically treat me nicely, automatically perceive me as being friendly and personable.
So it's a trade-off. Being female is, by its nature, being more open and vulnerable. People just assume they can do anything to you. And while it's definitely a bit of a curse because this means that people don't respect you, and guys think they automatically own you and can say whatever they want, it's also nice to have people be more willing to be emotionally open back. And while the former definitely sucks, the later still makes it worth it for me. Every time a cashier gives me that warm welcoming smile, and doesn't immediately get defensive when I ask them a question, actually talks to me instead of just assuming that I just want to check out and be done with it, it reminds me that it's worth it.