Wow, I thought I was the only one with this problem, as embarrassing as it is to admit it. The first time I had sex, it was... painful. It didn't occur to me that the foreskin had to retract during sex, and in my early years of masturbation, it had never occurred to me to do so. The kind of phimosis I had was the kind where I could retract the foreskin when I wasn't erect, but not when I was. So maybe it wasn't as bad as other cases.
Anyhow, I didn't see a doctor about it. Too embarrassing. So what I did was this: have sex like a madman, everyday, for hours, over and over again, until it stopped hurting. See, by the time it stopped hurting, the foreskin had already stretched enough for it to be no longer painful. It took a few weeks, I'd say, but it was worth the pain! And my then-girlfriend (now my wife) was ecstatic. ;-)
I don't know if I would suggest this to you, but the point of my story is that the foreskin is just skin, so it WILL stretch.
I'd caution you against circumcising this late in life. You may lose a great deal of sensitivity and pleasure. And it's hard to get that back once you cut it. I've known two people who have been circumcised while adults, and neither were that happy about it. It was very painful for several days post-operative. One of them did it because of religious conversion, and I have no idea why the other did it. Just that it hurt like fire when urinating.
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