I'm a small fry and I do it all the time by myself -- and my bike ain't exactly light (~500lbs. wet).
here's what I do with my PITBULL swingarm stand (not the spool type):
First thing, put bike IN GEAR so it doesn't roll away; then put it on sidestand.:leghump
Roll the rear stand behind rear tire and line up the left side support nubbin on the stand under the left side swingarm.
Position self on left side of bike (facing it), lean left thigh/hip into the bike tail section to straighten it up, keep left hand on grab handle/tail to pull back onto sidestand in case you lean it over too far. Peak around the other side to make sure the right side nubbin is lined up good (you may have to shift/angle the stand a bit), then push down a little on the stand handle to seat it firmly under BOTH SIDES of the swingarm.
Then, keeping downward pressure on stand handle with right hand (to keep the stand seated) and keeping left hand on bike handle for stability, I pivot on my left foot to reposition myself behind the rear tire (so you're looking straight at the tail light). Then, simultaneously push right hand down on stand handle and push up with left hand on grab handle or tail. Easy, though it might take a couple tries to get it smooth and automatic.
Taking bike off stand, I stand behind rear tire, left hand on left handle, pull up on rear stand handle with right hand and ease her to the ground. Gently lean it on the kickstand.
Hope this helps!