Startropics
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Okay so there is an old Nintendo game called Startropics. If you have never played it is similar in style to the original Legend of Zelda in its play style, only it has better graphics.
Okay so the basis of the game is you play Mike who is a boy on vacation in the pacific Islands. You were supposed to meet up with your uncle only he was kidnapped.
You are then handed a yo-yo and go on an adventure. that's right a yo-yo.

Now you may wonder why I bring this up.
In chapter 3 you have wrecked your ship and the only person to fix it is the chief of Miracola. His daughter is sick and needs the scroll of OBOB. Only to get to this you must cross a bridge, the only person who knows the secret to the bridge is the head warrior of Shecola (a Place only women may enter).
So in order to go on you help the fortunate teller with what she needs and she dresses you up like a girl so you can get in to speak to the head warrior.

The only dissapointment is if you say your not ready to get out of the clothes you cannot leave, and there isn't much to do in Shecola.

If you beat the game you get to see Mike dressed as a girl, along with other scenes from the adcenture.

If you are not big into video games there are a couple of Deviants on this particular part of StarTropics.

Sorry that was really long huns.  
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OopsiePanty
I totally forgot about that part of the game, but do remember it now that you have mentioned it. Oh those wacky Japanese, they totally accept lots of gender bending stuff the USA won't for a century, but the laws in their country for trans people only became friendly like a year ago. If I was a Japanese citizen right now I could be declared legally female on my passport, but in America I cannot :(
A young girl's greatest fear isn't monsters, or magical threats from beyond time and space.
No, a young girl's greatest fear overshadows all of those things.

Her greatest fear is to be alone.


(Still your little Guardian Shadow, now just with wings!)
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