Not sure if this is appropriate, but it's a legit question about this activity. I've been seeing someone every week, very awesome person. So this weekend is his birthday and he wants to celebrate with me, and I wanted to make it special, so for a couple of weeks I've been inquiring about his fantasies. He told me his biggest fantasy is to be raped. How does one do that when obviously physical strength isn't overpowering? Not much in the porn department research because most of it is geared towards men. Besides some satin straps and blindfolds, maybe handcuffs, I'm out of ideas.

Hit GaG up for some rope. He has plenty to spare. When your "date" walks in the door have a booby trap set so he trips upon entry. Cover his mouth with your hand and tell him if he screams out you will (insert threat).  
This will only work if you assert yourself in the very beginning. Forget the satin shit.  

He doesn't expect you to physically overpower him because he knows you can't.  So just start pushing him around, shove him down, be very aggressive verbally and then tie him down.  After that, just play it by ear.

just invite some of the homeboy ex-cons over..they love to full-fill...

I know of many here in ChiTown that could easily direct you...maybe even participate in this fantasy.

re a male prostitute to rape him.

Is it that he wants to be surprised and out of control, or does he want you to be more aggressive and abusive, or does he want to be restrained, or what?  Many of the suggestions seem pretty good.  What about tying him to the bed and then doing him with a strap on.  Just get a safe word before you start.

I've been reading Jay Wiseman's book "SM101".  He discusses rape fantasies and more importantly, safety.  I have it on my iPad.  Also recommend the BDSM board and checking out Sabrina Morgan on Facebook.  Another possible resource is the Art of Submission web site.

Thanks for the helpful comments about aggressiveness, rope, tie ups, covering mouth, threats, etc.

Also tell him to see other girls , the clingy ones can become an issue !  

Well, you could marry him, have him buy you a house and then rape him in  divorce court.