Being trans in the 1700s?

So I'm a writer and I'm working on a story about a man who, long story short, becomes a pirate, him being trans becoming my only writing issue so far. Now, I'm a trans man so im applying my experience where I can but I didn't live back then.

He lives in England at the beginning before a series on events leads him to sea, what would life on land have looked like for a trans man at that time? What about binding? Would he have had to live as a woman while on land and in regular society before being able to express himself as a pirate?

I get that I probably have a little leeway here but I love accuracy as close as I can get it