Connotations of using "boy" by upper-class liberal Britons in beginning of 20th century

Solution 1:

I apologize in advance for not being able to provide a more well-documented answer, or even a whole answer, but I did find this.

From: Eureka Encyclopedia

Boy (Broad boy; Buff boy; Business boy; Call boy; Career boy; Come-on boy; Fag boy; Party boy; Pratt boy) Male prostitute.

it also lists

Rent Boy

and

Baggage Boy

Solution 2:

Sample usage,

http://en.wikipedia.org/wiki/Mad_About_the_Boy

written by Noel Coward (smack in the middle of your demographic), clearly uses 'boy' to mean adult.