Hand pumps can be hot but I really like the images of guys being milked while tied down by electric pumping machines that continue to pump to multiple orgasms until it's painfully dry. I'll try and post some pics.
I've seen this one before and it's one of the hottest sleeping guys vids ever - makes me cum every time. It's got everything - a passed out hunk, stripping him, sucking him, reolling him over helpless to get plowed in his sleep by these hunky dudes, and then made to cum without even knowing it...