You now have two files: 'my-font-italic.otf' and 'my-font-bold.otf'. The first is obviously italic and the second is bold. Connect both to your CSS and assign one to .container and the other to .small.
Unfortunately, you won't see the changes of the result after you connect the font. But this is still good practice (and a nice quote from Jamie Zawinski).
Tip: For the first font, font-weight is normal and font-style is italic. For the second font, font-style is normal and font-weight is bold.