There were several stories about an older aunt that ran him around naked and milked him on schedule. She sent him to a special school for naked young gentlemen in crotch panties
That sounds like "Craig & Irene" by jeffrey214.
The author removed their stories for unknown reasons. That one can be found in the wayback machine though.
Go there and search for www.literotica.com/s/craig-and-irene-ch-01
