You may want to go online and look for yourself, in front of him. You may tell him you want to look at some porn w/ him. I look a porn w/ my lady friend and we discuss some scenes, too.
If you really want to rock his socks, go to "google" and search for "shemales". This is a sight that shows half female and male.
Obviously, he feel embarrassed, but you can make him feel more comfortable by watching w/ him.
Some of it is funny to me and some is gross. I don't like anal sex.....
I hope this helps and doesn't offend you.