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Background Pony #335B
I would say that it’s less that she’s questioning his masculinity so much as insulting it outright.
Star Cavalcade

If Celestia hadn’t outlawed pre-marital sex, then this wouldn’t have been an issue.
 
Of course, there wouldn’t have been a wedding episode either.
WM-R
Speaking Fancy - For helping with translations

“That’s…that’s a pretty specific sense, sir. I can’t imagine many situations you’d need it.”
 
“You’d be surprised.”