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this post was submitted on 16 Jan 2026
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Asklemmy
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I don't really cross dress, but I have a pair of heels kicking around for a Halloween costume (Monty Python Lumberjack) and I occasionally trot that costume back out.
I basically went to payless (back when that existed, I guess the modern equivalent in probably mystery Amazon brand shoes) and found a pair that more-or-less fit. Staff was actually pretty helpful, apparently around October a lot of guys wandered into payless looking for heels for a Halloween costume. They pointed me right to where the biggest heels could be found.
I think getting a cheap pair was the right move, because they pretty quickly stretched out to better accommodate my feet. I have fairly wide feet even by male standards, and actually found them to be reasonably comfortable all things considered after they broke in (which didn't take long, those shoes definitely weren't designed for the stresses of a 200-whatever pound man moshing in them at a Halloween concert)
The harder part was trying to find a bra that even remotely fit my frame.