I have to say I sure had the pucker factor going when I showed up with my wife on pillion last year at the wonderful gathering Mayberry Days. The place we stayed was on the Blue Ridge Parkway, and the property spanned a small divide, and it was gravel to the main building, and then a gravel road that went down one side of the divide, and up the other side to where it met grass and reasonably decent parking.
As I arrived that day, I stopped at the top of the hill, and just made the decision, "screw it -- this *should* work".
I kept it in second gear, and treated it like snow going up the other side, trying to maintain traction and forward progress without wheel spin.
The pucker factor was high, and I was fighting it (the folks on the porch saw me fighting it and said later they were surprised I made it). About half way up the hill though it seemed the bike knew what to do, and made it to the top. While the rest of the stay was not a sleep walk, and each time I went down the hill it felt like a commitment with no turning back -- but it all turned out o.k., and now I have that experience. And the best part, my lovely spouse has greater confidence in going with me as a welcome activity.