I wish I had an answer for you.
I have mostly been blocked by distraction, until the last decade, where the woman got in the way. (She knew before she moved in.)
It's there every day, but usually I'm too busy to notice. Got a job to handle, got housework to do (even in the apartment, the woman seems incapable of doing anything on her own... slight exaggeration, but only slight. Sometimes she cooks dinner on her own, most nights I help. Ditto dishes. Ditto house keeping. Shopping. Etc. She's a "yellow" in the Hartman Color codes, I'm a Blue... Wonder where others here fit in, but that should be a different thread. I believe she sees having others around as "entertainment" ...)
Anyway - I've been "very successful" in my corporate career, though I've probably seemed immature and childish at times, and I can be silly, and I have a pretty good sense of humor, but sometimes snarky, sarcastic, dark...
You know, a lot of things we tend to associate with "feminine" individuals. This indicates to me it's ALWAYS there... Just submerged most of the time.
But what sets it off, I can't tell you, beyond a few overarching things.
1. Dad was a cue ball (bald). He also almost died on the operating table during prostate surgery, it was the size of a football. The doctor came out of surgery looking like a slaughterhouse butcher. I also disliked dad as a bully. Put it together, there's a disinterest in being or becoming male.
2. Grew up in the era of "GRRL POWER!" and "anything a man can do, women can do better." Seeing it on TV, it goes into the brain without a filter. HEARING a story doesn't work that way, nor does reading. SEEING a human do things, that makes it "real" and it bypasses logical thought. E.G., Teenage Mutant Ninja turtles, they had to NOT show the sewers in the sequels, because idiot kids went looking for mutant turtles and got injured in the sewers. (Mediocre example, I'm afraid, but the Darwin Awards will suffice for further examples.)
3. Women were ALWAYS gorgeous to me. I never had that "division" situation, where boys go play one way, and girls the other. (Happens about 7.) I was "one of the boys," but didn't see girls as "The Other." Besides, they were nice, and friendly, and talked to me (and the boys in school, at that time, were imbeciles looking for trouble. Rugby on a rock-filled, tree-stump filled, no-grass stretch of ground? No thank you! I preferred the monkey bars, doing flips, stretching my body, building strength - not running around, risking a concussion, knocked-out teeth, torn clothes - all of which happened, BTW, it's not just irrational fears.)
So, I wanted to BE one of them, and patterned my behavior on them. (there's a certain parallel to "Song of the south," I think it was, where mommy sent the boy out in a lace collared velvet Jumper, I think it's called... Not dissimilar to my first day of 8th grade, a bow tie, pullover sweater, button-down shirt... :-P)
Positive and negative reinforcement together, nature versus nurture, and the ultimate question is: Was it one, or both?
I've been thinking this over since I was 7. And I have competing issues, too - I want to be STRONG. The strong can take what they want; the weak suffer what they must. (you can hedge the bets, minimize risk, but the law of the jungle still holds true.)
And strength (e.G., "70s big", "Lift Big Eat big", etc.; it was also the era of Arnold...) is diametrically opposed to being small, yielding, graceful, feminine. It was sort of a way asserting I was a man. But I don't seem to relate to "men" too well, unless they actually like relationships. (friendship counts, as you discuss the world and your thoughts, history, women, whatever.) It's a "chemistry" thing.
By the time I was 10, I was crossdressing. Just "felt good." I was also putting on weight, so pseudogynecomastia made me look chesty. I underdressed a few times in high school (an all-boys Prep school, to make sure I got a proper christian education, with no "distractions")... I started stealing my mom's herbal hormone stuff then, and finally got my own. (change O Life, as it happens.)
Went to college, found the "adult" book stores, found forced Womanhood and Petticoat Tales, I think it was...
And had to hide these things all the time, too.
You do NOT want to stick out in the late 90s, in a Catholic education facility, though I probably could've managed, and might even have thrived, in some ways...
But it was always there, always echoing in my ears, like mental tinnitus.
I think the "flip-flop" effect is just due to how much distraction vs. dissociation we have at the time. Like a dig wagging its tail, hitting a wall or chair: the dog doesn't care then, but if you step on the tail? THEN they hurt.
Not enough distraction, or actions to correct the dissociation; or, too much dissociation; and you're right back in the soup, trying to find a way out. The easiest way out is through, so out comes the lingerie, the dresses, skirts, makeup, whatever will calm the storm within.
Some men quilt; some do cross-stitch; some arrange flowers (E.G., Samurai). They don't necessarily have any desire to transgress gender, it's just a hobby.
How is that particularly different from us?
Our work of art is ourselves, really, and we need that time and license to be ourselves - and it is denied by a masculine structure, which has gotten EVEN MORE rigid since the Sexual Liberation of the 60s.
I think this sort of introspection is useful, but not really essential. We all have a different path to get "here," and many a different final destination. So while it's all good to reflect and analyze, ultimately, it's just a "course correction" mechanism, and we might as well not overdo our self-analysis. It would be like taking a PM pill, then measuring your chest... Then taking another pill, and re-measuring.... Sort of, "I went to the gym three times, why am I not skinny yet?"
Useful on a quarterly basis; less so on a daily one.
BTW, the "Flip-Flop" mechanism you seem to be getting at, is straight out of Maxwell Maltz's "Psychocybernetics." You've defined the cybernetic mechanism of course-correction. ;-)