I hesitate to describe any of my experiences as gender hell, nor even as gender-driven. At best, there have been moments when I have run afoul of a parent's expectations on how I should dress, what I should study, or what career I should pick.
There was the parental shock when I decided at age 17 to have my ear pierced, but I think this generally went along with their disapproval of the way I prefer to dress. (My father almost always wears a dress shirt, slacks and shoes; I'm never entirely at ease unless I'm dressed comfortably, by which I mean jeans, sneakers and a nice nonbuttoned shirt.) That's partly a generational thing, but mostly an area of social expectation. I started wearing an earring in 1987, when it was still linked with gay men. I also wasn't (and still am not) terribly interested in sports nor in competition in general. I don't know if my parents ever worried that I was gay, but I suppose they might have. If they did, they never said anything.
Same reaction to my long hair, whether it was in high school, at college, or after I returned from Haiti and up until I finally had it cut off for good a few years ago because of the cancer. It was more that I was going against their ideas of what was "proper" and was rebelling, rather than a fear that I was not being masculine enough.
And I think that continues to the present day. I'm living against their sense of proper gender roles to this day, being a stay-at-home father while Natasha works and brings home the bacon. My mom has said in the past that this isn't what she imagined I would do with my college degree, and my dad flat-out told me two weeks ago that he considers me to have wasted his money on my college education, and pretty much said that I'm proving to be a big disappointment to him by staying at home with the girls. (He also didn't approve of my major, English, and laughed out loud when he heard I was doing a senior honors thesis on Classic Star Trek and its religious themes.)
So I'd have to say that, as a guy, I've encountered some negative reactions from my parents in particular over gender issues. The hair was a sticking point for a long time, because men aren't supposed to have long hair, but that was largely tolerated because I was working as a newspaper editor, winning professional recognition and moving up the ladder somewhat. (I might have climbed farther if I were more professional, but there you have it.)
But while my parents have voiced anything from ambivalence to disappointment in my choice to be a stay-at-home dad, I can't say that's a reaction I've encountered much elsewhere. I did have one fellow from college presume to give me a lecture about my God-appointed duties to provide for my family, complete with the "Go seek godly counsel and pray about this so you can know what God would want" (i.e., go pray about it until you agree with me), but by and large people have been pretty accepting and open to this. A number of men have told me that they wish they could do what I've done (or wish they had when their kids were younger), and a number of women have been impressed that I'm comfortable enough with myself to jump out of my career in the middle of the stream. One or two gave me the come-hither eyes, but that's another matter.
The only negative reaction I've had from women in general has been at places like preschool or on the playground, where my attempts to make conversation or to ask them if they would be interested in play dates sometimes have been seen as "predatory man hitting on me." But I've also found that after they get to know me, even if it takes a play date or two, they realize that no, I'm not awash in testosterone, I'm not angling to sleep with them, and in fact I have many women I count as friends.
So, gender hell? Not for me, thanks. I'm afraid I've gone no deeper than the First Circle. Let's call it "Gender Heck."