I didn't know what cuckolding actually was until the advent of the internet but the first sign would have been when as a teen I read an article in one of my ......'s 1990s women's magazines about the 'Hung Jury', a dating service for women exclusively made up of men 8 inches and over.
One of the members was quoted as saying "I'm not sure of my exact measurements but mine is the same size as two Coke cans on top of each other". I compared my little pencil to that and was amazingly turned on to think how much smaller I was than him. From there, my masturbation fantasies revolved around SPH and cuckold scenarios - helped by the fact my best friend at the time's cock was well above average.