I had exactly the same problem you had, Marine. Do a search for 'phimosis' or 'foreskin' and I'm sure you'll find some posts on this.
My personal advice is to get a doctor to look at it, just to be on the safe side. Don't agree to anything, just get a doctor's opinion.
I had your exact same problem up until two years ago. I first started having sex at age eighteen (at the time she was the right woman) and I didn't enjoy it at all because it hurt when I entered her. The foreskin doesn't retract properly and when it's pulled back it's so tight it hurts.
After that relationship ended and another one began I eventually went to a doctor and he gave me a cream to put on my foreskin twice a day for a week or so. He also said to try and retract it a little more every day. Literally, to stretch it. That, coupled with the cream (if you do a Google or TFP search on 'phimosis' you'll find the name, it's escaped me right now) was all needed. And I'll bet it's all you need, too. Mine doesn't retract by utself when I'm hard, but when I'm hard I can do it myself and everything's fine.
If you don't want to see a doctor then from now on just retract your foreskin as far as it can go without being too painful, hold it there for a few seconds and then leave it. If you do this a number of times it'll stretch properly. If you do want to see a doctor (and I recommend this) then he or she will give you some more specific medical advice.
The most important thing to remember when it comes to sensitive issues like this is that you are almost never alone. I'd never heard of an issue like mine before, and the doctor reassured me that that sort of thing is actually very common.
Just a note: I know some people believe that if it ain't broke, don't fix it, and also that if you can get erect, ejaculate, etc., then there's nothing wrong. In my personal experience (and I stress that this may not be your case), when I had sex my foreskin was forced back and stretched so much that it was unbearably painful. Obviously before I'd had sex this wasn't a problem since we're in total control when we masturbate. But the stretching when I had sex was unbearable and led me to see a doctor, who, in turn, helped me find the solution.
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