@kyles,
There's no consent on your part, right?
Then that's generally the definition of rape.
What concerns me more is that this has happened in the past and not just with this particular asshole. Who are you spending time with who thinks it's okay to just start penetrating sleeping women? And why are you having so much trouble not telling anyone who does that to **** off?
Also, stop going to this guy's house, drinking with him, smoking with him, etc. If you won't do it for your own self-esteem and well-being, then at least do it as a measure of keeping your job.
You're right; it's messed up. Don't make it any more messed up.