Googling this brings up some answers. Anyone know more?

Wilson writes: “A ‘peg-boy’ is a young male who prostitutes himself to homosexuals; ‘peg-house’, a homosexual brothel. There is an unsubstantiated story that boys in East Indian peg-houses were required to sit on pegs between customers, giving them permanently dilated anuses.” Whatever you say, Bob.

http://www.straightdope.com/columns/read/2794/rum-sodomy-and-the-lash

Dave (12018) -- 06.20.2001

According to folklore, there was a position in Her Majesty's Navy called "Peg Boy." Peg-Boy's demeaning role was to be there for the pleasure of the sailors during long, lonely voyages. In order to remain, err, loose, Peg Boys were forced to sit on pegs to, err, keep loose. I imagine they were kept on a particular deck on the boat... and due to their, err, unconstricted status, I imagine they were prone to leakage. Hence, Poop Deck

http://www.poopreport.com/Ask/Content/poopdeck.html

Googling this brings up some answers. Anyone know more?

Wilson writes: “A ‘peg-boy’ is a young male who prostitutes himself to homosexuals; ‘peg-house’, a homosexual brothel. There is an unsubstantiated story that boys in East Indian peg-houses were required to sit on pegs between customers, giving them permanently dilated anuses.”

I have heard this version many times. I tend to give it some credibility as the articles I have read also refer to East Indian guys. No other backgrounds or countries.

btw what brought this up? Are you thinking of opening a "peg-house"

They used to have whipping boys too. The deal was you could never physically hurt a young prince, so what could you do when he was bad and deserved a spanking?

Simple you raised him with another boy his age who would be his best friend. Then, whenever the price behaved badly he'd have to watch his friend get whipped.

They used to have whipping boys too. The deal was you could never physically hurt a young prince, so what could you do when he was bad and deserved a spanking?

Simple you raised him with another boy his age who would be his best friend. Then, whenever the price behaved badly he'd have to watch his friend get whipped.

if that's not some fucked-up homoerotic shit, I don't know what is.

In order to remain, err, loose, Peg Boys were forced to sit on pegs to, err, keep loose.

This seems counter-productive. In my experience, whether I am being top or bottom at the moment, the top wants the bottom to be tight, not loose and sloppy.

What am I missing?

What am I missing?

That peg is slang for fuck. The rest is best classified as urban myth.

The rest is best classified as urban myth.

Aha! Thank you. So that the governors of the East India Company would not catch on to what they were, in the main, funding?

Aha! Thank you. So that the governors of the East India Company would not catch on to what they were, in the main, funding?

As long as their dividend was secure, I doubt the governors much cared to inquire over closely into the antics going on below decks. Besides, a happy crew is a productive crew.

Besides, a happy crew is a productive crew.

To a point. But then viz., as you know, Confessions of an English Opium Eater. Distractions.

Wonder what they'd do with a peg leg?