I decided to explore how old the longer phrase "sweet sixteen and never been kissed" is by doing a Google Books search. The oldest is 1907, and there are about fourteen relevant hits between 1907 and 1930. Interestingly to me, some of them refer to _MEN_. Here are two of them:
1) From the magazine, the Saturday Evening Post, '"Sweet sixteen and never been kissed. Ain't he the cunning little thing, ladies?" Well, that was a goat getter for fair. The kid's face got red clear up into the hair and his ears looked like a couple of rose leaves.' It was used to tease a young man, making him blush!
2) Another: "Johnny looks like Sweet Sixteen and never been kissed, while Fred appears as a man expecting a large inheritance from a wealthy maiden aunt. We can't all be handsome."
A few of the rest:
1926: '"Sweet sixteen and never been kissed." Only that wasn't true. She had been kissed — lots of times. You went to parties and between dances you sat on porches, on the railings, usually.'
1922: from a company newsletter, for employees of the American Woolen Company, next to a yearbook-like picture: "Eleanor Is Some Girl. Sweet sixteen and never been kissed. That's pretty Eleanor Harpring. Besides being a good reeler, and a heart-breaker, Eleanor is an excellent dancer. Eleanor is a prime favorite with all who know her..."
So, the phrase at that time informal, polite, considered a compliment, slightly teasing, and with slight overtones of sexuality.
"Sketches Drawn from Marshall and Vicinity, Past and Present," suggests that "the old phrase 'sweet sixteen and never been kissed' originated in connection with corn shucking parties. (Corn means maize, and chucking means removing the tough green leaves from the ear). "There were red ears of corn and white ears of corn." That is, the kernels were red or white, and you couldn't tell which until the ear was shucked. "If a girl shucked a red ear, her sweetheart could kiss her." And that, unfortunately, is all Google shows us.