If you're NOT traveling in male mode, using an outdated photo isn't really a good fight to fight or smart game to play. And it has nothing to do with transequality, etc. It's simply an issue that a traveler's government-issued photo (i.e. passport, GlobalEntry, SENTRY, etc) must accurately reflect their current state of appearance, presentation, etc. At university, I studied for two semesters abroad (non-consecutive), my photos were outdated (both male) and didn't physically match my then-current appearance (still male, but grown-up) - I ran into many issues at various passport checkpoints (airports, Eurailing through countries, etc).
At the very least, the person represented in the government photo is the person they will be looking for should something ever happen - they need to know who they're looking for. An outdated photo or photo that doesn't match your current presentation helps nobody. A new passport is $60 USD and lasts 10 years...my nails costs more and last 3 weeks...