So I'm guessing there isn't any way of doing it 'automatically' using only CSS?
I think first-letter can still do a lot for you. Span might be easier to do but with a little setup ahead of time, it would be easy to apply first-letter to new entries.
Something like this -
margin: 5px 10px 0;
box-shadow: 0 0 10px -2px #999999;
Your quote marks might work well as an actual background image.