I've had this discussion and considered the logistics of the operation :-) here's the list of necessities.
1) the girl willing to do it, that you're willing to do it with :-)
2) A tandem rig, and rating if you want to keep it even mildly justifiable (not to mention survivable)
3) a small plane where you can buy all the slots
4) a DZO you can bribe with beer to not notice
5) a "blind" pilot... not totally blind... just selectively
if you have all this we figured the best bet would be to start in the plane and when you're ready jump, then you have ~45 seconds to chute :-)
I appreciate there's more freefall time than that, but I figured the chance of loosing altitude awareness might be a little increased under such circumstances...
on a slightly different note, I errr "found" a vid of a few porn stars jumping while innocently browsing the net... looks like it's at Elisnore in Cali... don't know if I can post the link here but will pm it to anyone that wants. is pretty funny stuff, lucky tandem master.