Well I finally did it. Maybe my hole is smaller than average but it took several tries. How did I do it? Determination? LOL. Today I took the plug with me into the shower. Got my cockhead nice and hot under the warm water,then I soaped up the plug with some shower soap (no-fragrance kind, I thought that might irritate. Then I just started applying steady pressure, yeah it kind of hurt but not as much as before, and suddenly it just slipped in. Its always something...then I started thinking about pulling it out. Its definitely "in" when it in...no danger of it falling out, at least not out of mine. A slight tug did nothing! It took a pretty firm pull and it did hurt a little coming out and I think tore my hole a tiny bit, there were a couple of teeny droplets of blood and that was it. 2 hrs later and I feel fine...maybe ready to go again.
It feels pretty hot when its in.
Good luck with yours.