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My wife was proud of me the time I told her I stopped for gas in a skirt (to be fair, it was 4AM, but I was also driving around without doors on the Jeep.) She's also been proud of me for wearing leggings in public when travelling and a few other minor things that I've done, all while presenting as the male I am. She does help me not get caught by friends and family, not because she's ashamed, but because she knows I don't want to get caught. Once she bought me a new anklet while in Cherokee and she was upset when I told her I was going to take it off for the party that night. She was quite happy when I left it on, along with the toe ring that I always wear.
So no, she's not ashamed of me.
PS, if you wear a skirt while driving sans doors, be prepared to flirt with indecency. :)
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I'm pretty sure my wife is ashamed of me but it has nothing to do with me wearing woman's clothing.
She says I'm the 7th kid ... lol