I definitely think it’s a vulgar double-meaning but I think it’s less “women walk over over him” and more “he’s gay”. It’s practically lifted right from The Miller’s Tale where the “dandy” and feminine male boarder is repeatedly described as “handy” and is both clever and literally very handy with his landlady in the “locker room talk” sense. The story ends with the dandy boarder taking a hot iron rod to the butt and the cuckholded landlord, a carpenter who you would expect to be stereotypically “handy”, breaking his hand.