There's been a lot of great advice. I'd add to Jamtart's info, that the irritation from nonoxynol-9 also causes "micro-tears" that are thought to increase your chances of contracting an STD. It's believed that the irritation comes from the detergent properties that nonoxynol-9 has.
On the "second ring"... I had a friend teach me about it, in more ways than one.
First, when he was bumping against, mine actually hurt. He explained to me what was going on, and told me to relax, "I don't mean your hole, I mean YOU. Relax your whole body." He worked it VERY slowly through (patience is a big key to anal anyway), and it was hurting a bit, to the point where I almost had him stop, but he kept talking to me, relaxing me. When it finally was through, and he was all the way in me... my toes curled around so far, I think they were scratching my calves.
I was lucky with him, because it really was a case where he knew what he had, and he knew how to use it. He explained everything to me, but also kept assuring me that he wasn't going to hurt me, he wasn't going to just slam it in, and all of this contributed to me not tensing up, and making the whole thing either painful, or just impossible. Some people are into the pain thing, I'm not, so his approach was perfect for me. He really had saintly patience. Now, once you get warmed up, well, in his words (so don't blame me for the cheese), "your tight little bud, is gonna open up like a beautiful flower." Then, you can pretty much take whatever he gives you. In this instance, I went from hearing, "shhh, just relax for me, I'll only put in as much as you can take" in the beginning, to hearing, "See? I told ya that you could take it all. Dude, I was SLAMMIN' you, and you were totally taking it for me." at the end.
Finally, if it's rough, yes, you can do some damage, but from strictly a non-medical point of view, think about this... The sphincter is supposed to loosen and recontract, and if it got permanently stretched every time something went through it, by about age 10, you'd be wearing diapers again. There is the whole arguement that the direction of passage in this case is "unnatural", and thus "different", but really, it's a band of muscles, akin to a swinging door, it only "knows" that it's being opened or closed. So, even with a battering ram, you can slowly and gently push open a swinging door, causing no ill-effect to the door, or you can go through it at full charge, and do some serious damage. Of course, all of this also assumes you aren't taking it 5 times per day, 7 days a week.
P.S. After Mr. Big-n-Deep, I was later with another friend that was on the lower end of average, who, afterwards told me, "Man, I love that you're so tight." OK, OK, it was good, but after the initial tightness, I admit I was wishing he was reaching a bit deeper.
But "ruined" and "spoiled" are two different things. LOL!
