What an interesting thread! Thanks FA.
My experiences mirror Arch's almost exactly, probably because we're of the same generation. I had several additional problems, such as being forced into stereotypically 'female' subjects at school (e.g. cooking, typing, sewing & knitting) without any option to drop them or choose alternatives, because that's what the government mandated at the time. Good ol' Apartheid South Africa was all about putting people into very specific boxes in more ways than one, and gender roles were very strictly enforced at all levels of society.
When my elder brother graduated High School with distinction, our parents proudly paid for him to study at one of the country's most prestigious universities so that he could have a good career and support his family. Three years later, when I also graduated High School with distinction, my parents refused to pay for me to attend any university or college at all, because like Arch I was expected to get an 'easy' job to tide me over until I could marry Mr Right. My brother's advantage here is undeniable, because he got an excellent tertiary education - at our parents' expense - before settling down and having kids... whereas all of the tertiary qualifications I've earned have been at my own expense and whilst working full-time as my family's main breadwinner. If I'd been MAAB, I would've had the same encouragement and support as my brother and my life would've been very different. Perhaps that's a generational thing? My folks were born just after WWII, and were quite old-fashioned in some of their views.
Granted, if my brother had been trans* and had wanted to express femininity, I don't doubt for a second he would've faced the full wrath of society for doing so; probably moreso than I did for expressing my masculinity. But knowing my family, he still would've been offered the advantages I was denied, because our folks would've believed that he was 'really a boy' and they would've pushed him to succeed accordingly. But for me, whilst I was allowed to be a tomboy for a brief period, my folks were pretty darn convinced that I was 'really a girl' and they certainly treated me accordingly, i.e. like a second-class citizen whose sole purpose was to look pretty so that I could snag a man who would support me. My upbringing as someone presumed to be female demanded that I learn to be submissive, be scared, be defensive, not put my head above the parapet... and that I didn't deserve a good education or a career, because my husband would be expected to provide everything for me. People who are MAAB generally don't get those same lessons growing up. And those lessons can be quite a handicap, if you take them to heart.
I spent the first 20-odd years of my career struggling to be taken seriously as a 'female' professional, because no matter how masculine I felt inside, everyone else saw me as being less than the male equivalent precisely because they perceived me as female. When my male colleagues were assertive they were considered dynamic, effective leaders, but whenever I behaved in the same way I was ridiculed for being 'shrill', 'hysterical', or a 'b*tch'. It was almost impossible to be taken seriously, and it certainly wasn't possible for me to earn as much as my male colleagues doing the same job.
I'm still working to overcome all this.