Bravo! Congrats!

I've been having my guy tell the children stories since I don't have enough housing for him to be able to kiss but his skill level hasn't gone up... how many times does he need to tell a story before he gains any skills for it?

Good for you!

I've been having the same problem. Is it a bug?

They don't succeed to tell a story every time but only if they go on the podium (or they say "no") and they gain parenting skills each time. But they must tell a lot of stories before you can see something changing in the skills' bar.

Oh, okay. My villager had been successfully telling stories for a while, and I was wondering about that.

You might want to look at this, which explains a lot about getting masters.

When I was trying to get Jack of All Skills Award, and my villager had mastered all skills except parenting, I just kept putting my soon-to-be jack of all skills on an elderly villager, and since older villagers can't have kids, my soon-to-be Jack of All Skills mastered parenting in several minutes without making any babies.