A dick rag can either be a rag that you use to wash or clean your tiny dick. The term "dick rag" my also be used in reference to the rag that you blow you huge load of cum into. This may be after ejaculation while jacking off, or when ur pussy ass girlfriend makes you pull out and cum into one of those dick rags.
Emily- "Honey you need to pull out now! Do you have that dick rag? Jeff- "Oh shit I forgot it honey, I guess I have to cum inside you!"