I dont think so, the only thing Dorithy wore more than once was her housecoat.
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Twice.
If he did, how would it ever escape that skin-tight outfit?? I absolutely cringe as I answer this, but yes. I believe it was in one of his 'Dark Knight' comics during the Frank Miller era.
Yes, her wrestling outfit (Fishnet stockings, knee socks, combat boots) and the fact that she wrestles with women.
Pretty sure that yes, he did. It was a limousine.
Yes, Constance Marie was bound and gagged twice in the TV show Cobra.