What does it mean when your boyfriend has a dream about you pleasuring him as a girl?

Most dreams are messages from the subconscious mind. You are just processing daily thoughts, feelings and events in the dream. Ask him what it means psychologically.

Okay, your boyfriend may be having these dreams for completely different reasons from what I did so do not panic when I say this, this is just from my own experience of these sorts of dreams:

Anyway, I knew I should be a girl from 9 years old and I repressed it, repressed it for a long time. Anyway, when I started dating and stuff and hanging with the girls more I started having dreams where I was a girl dating these girls or that I was just another one of the girls in my friendship circle. When I started hanging with girls at 14 my feelings of wanting to be a girl started seeping into my subconscious and when involved in girl talk, up into my consciousness. I believe I had these dreams as they were telling me I needed to come out as female and to be myself and to be truly accepted into society. Often when I was in these little dream worlds my friends were far closer to me before, which wasn't too different from the reality of it when I came out, I became really popular and I was accepted even more than I was before with the girls.

Now this is what these dreams meant for me, there could be a completely different explanation to what this particular dream meant for your boyfriend, however the fact he told you about the dream, could be a sign that he is trying to hint something to you. Again I could be completely wrong, he could have just felt the need to share his weird dream with you. Just giving my opinion though.

Discuss it with him though, ask him what he thinks it means, or ask him what the dream means to him. None of us can get inside your boyfriend's head better than your boyfriend.

"To dream about sex refers to the integration and merging of contrasting aspects of yourself. It represents psychological completion. You need to be more receptive and incorporate aspects of your dream sex partner into your own character."

And being the opposite sex can mean that you need to incorporate other qualities into your life. So perhaps he feels he needs to be more sensitive?