When younger, crying infuriated me. It would happen sometimes out of sheer frustration and the fact it didn't do anything to help me fix a problem made it an utterly useless biological response to whatever the problem was, in my opinion. I mastered the stone face; I desensitized myself to plenty of things so that they wouldn't shock or bother me. That also worked. Self-control has always been important to me.
I think right from the get-go, little boys learn that when they cry their parents probably don't come running and fuss over them to the extent they do with little girls. One of the interesting things about my childhood was that I didn't cry much. Even as a baby. And if I did, my parents did not really know how to do the comfort thing. I expect much like any boy I learned it wasn't generally helpful for me to cry. I remember my father actually telling me on one occasion when he was giving me a chewing out that crying wouldn't help me out of it. My mother was much the same. Strangely with my female siblings, they were the opposite. The behavior was not reinforced in me by any positive outcomes. That's not to say I didn't have my moments - but unlike women saying crying makes them feel better ("have a good cry"), it never made me feel better, only worse. I do not like my body having salty outbursts without my permission.
Since HRT I now understand it's very much the influence of female hormones in the absence of testosterone that makes emotional outbursts so easy. I've not had any since starting testosterone and believe me, the stresses and problems I've been dealing with since would absolutely have caused some tear shedding before it. The difference is remarkable; you can still feel the various emotions of a stressed-out state but the body's reaction of crying is - for me - nonexistent. Nothing will cause crying unless I choose to (one of my hobbies is a drama group, no problem there, I can switch the emotions on at will there if I want to) but the sort of knee-jerk biological response of crying is gone. I expect you'll experience the same when you go on HRT.
And you're right - people don't know what to do when men cry. They don't expect it. So they have no idea how to handle it. When a woman cries, it tends to stimulate an urge in other people (male and female) to help them. For women, crying isn't a bad thing, it doesn't invite ridicule and it does tend to cause people to care for you and find out what is the matter - or, if you're in a situation under threat for someone threatening to assume because you're crying that you're no threat, and to stop attacking you (or so you hope). For men, it's probably not going to have people flocking to see if you're all right. Though people recognize that fundamentally crying by anyone is a sign of distress, I think we're programmed biologically to worry far more about the wellbeing of women and therefore to respond the way we do when a woman starts crying.
I've seen grown men cry; they always had a good reason, and it's rare, in my experience, so when it happens I know they're really torn up about something and it's serious. They tended to cry only if a significant part of their life had just gone downhill - someone had been killed, especially a good friend or family member, or a long time spouse was leaving them and they didn't know what else to do to prevent it. Things like that.
But the fact that I saw them do it meant that I was a trusted friend or equivalent - they don't do it in front of just anyone usually, so when it has happened, I've been there as the support and my response was never to join in feeling miserable but to provide the foil for it. Frankly I've had lots of experience with people in states of duress and trauma, so it doesn't surprise me to see it. I know men are human and have emotions, it just takes a lot more usually to put them over the edge into crying about them. When it happens, I know they aren't feeling good about something, and not great about the fact they're crying, and they'd typically rather just stop and get it together than go on crying. When you're talking to a guy crying I think you have to assume he's on the edge, and they'd rather not have attention drawn to the fact they are. That's normal behavior in men, from what I see, and not just some social construct because bravado, or whatever. Most men literally don't delight in crying in front of people most of the time, myself no exception.
So for my part, I do not cry in response to things... instead I will quietly experience a bunch of unpleasant emotions internally, untangle them, and put them away. If something can be DONE about the situation, I will go and do it, which is 1000% more helpful. If not, I figure a way to move on rationally. Which is what I used to do as well, only now I save myself an hour's headache and constricted sinuses. It's not part of my life now.
How I feel about the guys crying? Anyone crying with a damn good reason for it is fine with me. The only time I get frustrated is with people who cry at the drop of a hat about what is essentially trivial problems, and to be honest I don't know any males who do this.
I'd never say crying felt empowering. Perhaps being in a fubar situation at rock bottom and realizing you can only go up from there kind of is, but the act of crying itself... no, I kind of see crying as like shivering when you're cold, a response to a state. Maybe it empowers females, but for me it never had the same effect as it maybe does for them.
I've also seen people complaining men should cry more and the fact they don't much is somehow some self-conscious play at hypermasculinity. Not true. Testosterone literally makes it much harder to cry and men have a whole lot more of it. It's a biological trait... and a fact for most with male T levels. Not much we can do about it. Personally I find it very comfortable to feel less highly-strung emotionally. I don't feel robotic or heartless in the least, but I do feel more in control which is the position I prefer to be in.
