I point up and as far as length goes on the XL it meets my cock on the topside where it touches my body pretty well. On the underside though, there is room between where the condom ends and where my balls start. I always try to tug on the ring and make it go down as far as possible and then suction it on.

The thickness will probably always be a problem for some. This is why I went from regular to XL. Regular always gave me a ring, and XLs are about 50/50 depending on my level of arousal. I actually think I'm more conscience of it now so I try not to get as hard cause I don't want the ring. =P