Every time I had to do something similar to this, I used Crystal Reports.

You can create a report with an Image field and read it from a binary column in your db.

Once you have the report object ready, you can export it to PDF and stream it to the client.

You can do it with a web app or with a web service (I'm using the latter to achieve maximum flexibility).

I think you could also do it via CLR, but I don't see the need for such a feature in the database.