Get your taxes done using TurboTax

If you are asking about the theory I can't help you. If the question is how to make the entries, there are sections for 1099-OID under Interest and Dividends for the OID and Stocks, Mutual Funds, etc under Investment Income for the 1099-B. Just transcribe from the forms into the corresponding boxes and, in my experience, TurboTax does the right thing.