It's been kinda interesting watching you guys go back and forth on this ... (your curiosty to know WHAT he wants to do far outweighs your ability to brainstorm WAYS to get him to be able to do it.)
jmf, as strange as it may seem, why not just try asking?
If this is someone that you've been in a relationship with for some time, have a solid base with, you'll at least generate some discussion, you may end up with the experience you hope for, and may open avenues for a variety of other, well, varieties.
There is still a struggle, incidentally, for women as far as being the sexual initiator in a relationship, particularly if you are dealing with a woman who's a bit older, since the cultural mores changed midstream and you end up fighting between the 'liberated women as sexual being', and the 'nice girl' your mommy trained you to be. This is extra-hard if you grew up catholic, by the way, no matter what the current religious viewpoint or lack there of may be.