You've got some good suggestions so far (and some pretty crappy answers too).  \n\n1.  Make sure that there is a long round of foreplay.  The more excited and relaxed he is, the easier it will be.  \n\n2.  Use plenty of lube. Infact, I would say, that you cannot use too much lube.\n\n3.  Try (gently) opening up the area with something smaller than what you're currently using:  for example if you're trying to use your penis right now, start with a finger first.  It's smaller and will go in easier.  After awhile of that, he should be reader for bigger objects.\n\n4.  Make sure that you're relaxed also.  If he can sense that you're getting frustrated or impatient, that will carry over to him and make the experience difficult for you both, physically and emotionally.\n\n5.  Check into literature and instructional references about this. The only one I've ever heard of is "Bend Over Boyfriend," but I'm sure there are many others.  Look into this together, it will be a unifying activity and give him confidence and reassurance, which will translate into being more relaxed during sex. \n\n6. Make sure to make these experiences enjoyable, even if you don't reach your "goal" right away make sure that the experience is not a waste.\n\nHope this helps.  Have fun!\n\nFR