Well,
last night I had a dream I was about to have intercourse with my best friend (whom I have a crush on). Anyway, for some reason I was the one with the penis, putting on a condom. And I'm the girl. What in the world?

I have had this dream before but with a friend not a best friend. I am a butch lesbian but I am of often trap between two sexes... I am just telling my view so this wouldn't be yours..

Maybe she is just more femme then you? This is the only reason I can think.. But i wouldn't read into it too much. We are always surrounded by a male and female view of things.. well i think so anyway. Cultures way of looking at 'love'

My best friend is a boy, actually. I think that was unclear...

Maybe it has to do with the roles you play in your friendship. Maybe you feel that you have to take charge more, make more of the decisions or that you are the one with common sense. (Traditionally masculine.)

Assertiveness is also a traditional masculine trait, so the dream could be about the need to be assertive and tell him how you feel about him

Putting the condom on could have something to do with protection/being vulnerable.

The dream could also be about a desire for each of you to be able to look at things from the other's point of view.