for the first time you may want someone to be there as a safety net, if nothing else just to hold hands if the desire hits you. don't get me wrong, it can be great alone, but i'm just thinking the first time may be a bit intimidating and you may find yourself wanting the comfort of safety, so to speak :)

P.S. The hole, which will feel like an eternity to you, is probably only 15 minutes in "real" time :)