text: When you start fooling around in a woman's anal area, you must work your way in slowly at first..  You don't just try to push up in her, it hurts too much.  You must first loosen it up (using dildo or whatnot), make sure you have lots of lube and make sure that she is incredibly turned on beforehand (and while you're loosening it up, it helps to continue to stimulate her nether region).  And wait until she is REALLY excited before sticking things back there.  Done right, it can be a mutually satisfying experience.  And then filling up the other hole at the same time...unbelievable!!\n\nAs for double penetration, OUCH.  Good luck with that.