Oh, I already am. ...Anybody ever watch Robin Williams Live on Broadway? There you go. Like a midget in a diving suit.
Have her help put it on. The masterbating with a condom idea is a good one too, I've done that one a couple of times myself. Try the warming sensations condoms or the tingling sensations condoms, Those seem to help for both people and might just help you get back up once on.
I had that with one of my guys, and what we ended up working out was having me just pretty much being naked around him, stripping, whatever. it pretty much ended up working Perhaps a different kind of condom? they must be uncomfortable. That sounds SO painful O.O