Way back in 2001, when sex columnist Dan Savage ushered "pegging" into the cultural vocabulary, one of his readers wrote in with the following tidbit: "Peg boy was a position in Her Majesty's Navy: He was the boy available for the after-hours pleasure of the sailors on those long nights at sea. To keep loose for his hard nights' work, he would sit on a peg during the day."
So were there really peg boys? What do we know about them? How did their, uh, position accord with the prevailing sexual mores of (unspecified earlier era(s) in England)?
I know this will probably get removed as too short but: no.
More? OK. Sigh.
The letter to Dan Savage's column seems to be the sole source of the "fact".
The story plays directly on the word "peg" and more generally on the extensive popular idea that sodomy was rampant in the Royal Navy. See also, the improperly attributed (to Churchill) quote:
“Don’t talk to me about naval tradition. It’s nothing but rum, sodomy and the lash.”
So, as a joke it's well-grounded.
But.
The idea that it was an official rating or station is absurd. Sodomy, which was a bit broad in its definition, was illegal in the Royal Navy. See also "Buggery Act of 1533". While it is as likely that homosexual acts occurred in the Royal Navy as at any other time in human history, it would not have had official sanction. Sodomy was a capital offence in the Royal Navy until 1861.
My expertise doesn't extend to historical practices or best practices for anal sex, but the idea of sitting on a peg to "keep loose" seems dubious. Perhaps somebody with knowledge could weigh in. I'm not being snarky here, I really don't know, and I'm also not judging.
tl;dr The content of story and its provenance point towards a cute tidbit invented to suit the column, by Dan or by a reader The specific idea of "a position" for providing same-sex sexual gratification is contrary to Royal Navy regulations for pretty much its entire existence.