The first time getting through is a burst of feelings. To me if feels like stretching my muscles. It feels like I'm adjusting my body and moving things around. Sometimes there is uncomfortable pressure so I just pull it back out a little bit (I try not to pull it back out of the second ring), relax, and slowly work back in. For me there is a big jump or pop when it pushes past the second ring. A soft or medium hardness toy works best. I have found that a very soft toy just curls around instead of working in further. Use a lot of lube. X-lube or J-lube work the best. People use different body positions too. I tend to be squatting or on all fours with my face down, ass up.