The way he is approaching it, there could well be problems. It's a big step from watching a movie and getting nailed by a BBC. It's hard to believe now, but my wife was very shy when we first started playing with sex alternative ideas over 20 years ago. We started going to bars and couples clubs until she was sure she was wanted by other men. Then, when she was comfortable dancing suggestively with men, the next step was a lot smaller. She now has been exclusively a black man's slut for years and lives for the next time her guys come over. The guy should also make sure he is ready for it.