I tried on a cockring for the first time. It's made of silicone and I put it around my testicles and penis. And then I jacked off. When I came, it felt like I didn't orgasm as powerfully or with as many contractions as I normally would have. 1. Is that normal? I'm thinking about using the cockring for sex. Usually I find that a little while after the first ejaculation, I can get it up again, but once it's up, it requires constant stimulation, otherwise the erection loses its firmness. 2. Would a cockring help for the second round? 3. Would it make it harder to cum during that second round? I noticed that with the ring around my testicles and penis, it shoves the testicles forward and up so that they are very close to the penis. 4. It seems like having sex with the ring on might cause my balls to get crushed between the woman and the ring if I thrust into a woman to the hilt. Am I worrying about nothing? Do you simply adjust the depth of your stroke to account for the fact that the balls pressed against your penis effectively shortens the insertable length of your penis?