Genuine question.
Imagine you get massages at work every Friday. This week, the usual massage lady is unavailable and a replacement has been booked. It transpires that the replacement is a man.
How would YOU feel?
I'd probably ask him to dress as a lady to lessen my semi-fearing anxieties at least. Nothing too formal. A miniskirt with tights, a vest, an arm-shaving session and a serious anti-ball-scent spray fired up the kilt should suffice.
It's actually less awkward with a man
No it wouldn't. I've had plenty in Turkey
Is it a professional/asked for massage, or just some guy coming up behind you on a crowded train?