I was in my early 20s and in the military. My foreskin would only partially retract, however that created no problem. While having sex with a young lady the foreskins connective tissue ripped. I was in the US armies European theater at the time and it was done at an army medical installation.
As it was painful and bleeding I was relieved to have it completed. In a way, I wish I could return to the pre-circumcision days so I could make comparison. That, of course, I cannot do. That was all during my free Gay days. I suspect had I been doing men it would have ripped a lot sooner.