StudlyScrewRite saidI 'dress' left. It's uncomfortable on the other side.
Actually, Joey's tailor was fitting men's trousers in what was once the standard and acceptable way.
In 1963 I was 14 and about to attend boys prep school. For which I needed some new suits, as we had no uniforms or school blazers. But instead of my Mother taking me to the boys section at a department store to be fitted, my Father unexpectedly took me himself, to his own tailor. Mom stayed home.
I was shocked, but also flattered & honored, a sign I was growing up into an adult. So I stood on a carpeted box while his tailor fitted my pants in a private room, while Dad sat nearby in a large padded armchair overseeing the operation.
Legs crossed, in suit & tie himself and looking rather like the Don from a Godfather movie, except he held a brandy snifter from which he sipped. A rather elegant touch at this establishment, the one thing I was still too young to share with him.
And as Joey 's tailor did, my Father's ran his hand up my trouser inseam, and pressed lightly against my balls, but making definite contact. "On which side do you dress, sir?"
On what side do I WHAT, I thought to myself. Dress? What does that mean? My mind raced, but in mere seconds I guessed it must mean on which side do my dick and balls hang, when wearing boxers.
"Neither," I answered, hoping I understood correctly. "I wear Jockey shorts." "Thank you sir," he replied, and adjusted the trousers accordingly. Otherwise he would have let out the seam of the trouser leg down which I hung, to allow more room.
And my Father sitting there, watching & listening to this, said not a word. It was not exactly the kind of male bonding experience between father & son I had expected that day. Neither was it the last time a tailor would ask me that question, as recently as my tuxedo fitting 8 years ago. Does anyone else still encounter that?