I have actually worn a regular on my hand pulled down to my wrist, whether or not it stretches was not my problem. The regular was a bitch to put on (always got stuck going down, was painful, sometimes popped during sex if the lube wasn't adequate).

My current gf was the one who informed me that I was above average and may want to try a larger size. When you see MAGNUM on a black and gold box etc., you're intimidated by it, and so I didn't think I could possibly fit in it. I put it on and it was an improvement, but still constricting and it left a painful ring around the base of my penis. I put on the magnum XL and it was very comfortable in comparison and stayed on well. It still leaves a ring around the base but the slight tightness doesn't offset the comfort when compared to the regular or even the magnum. Like I said, the magnums are intimidating market items. If it were up to me, it'd all be called "Condoms" in nice, bland print with the measurements at the bottom. I hate the stares from people in the store when I buy the XL's.

Your dick sounds pretty similar to mine. Have you tried the XL? The larger size condoms don't compress your dick so it feels more natural to her. If you can ignore the stares and the hype, it's really a comfortable rubber.

Sorry about jumping to conclusions about your comment. I have had a few girls and more than a few guys make me feel like shit about my penis. And I'm not completely secure about it now either.