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I would say you both have some serious sexual issues
Sounds like the two of you have discovered you have matching turn-ons! Lots of couples would love to be in both pairs of your high heels. There are *so* many dudes who cross-dress who'd love to have an understanding partner like you. You might want to tell him to get his own clothes, though, so he doesn't stretch yours out. Offer to help him shop.
So maybe she is into girls but hasn't realized it yet?
If he looked better than you in the dress & high heels... I would worry ;-))
I probably look better in your dress and heels then you do
Your life sucks, and you deserve it maybe.
Don't feel bad I have an ex boyfriend looks better dressed as a woman than he ever did dressed as a man
Keywords
OP's Boyfriend: I feel pretty, oh so pretty-- OP: *blinks*
Sounds like you know to bring into the bedroom now ;)