There's the first problem.
Now, it takes some work to get the foreskin completely down, and I can only do it when completely flaccid. And it takes a little work to get it back over again. The problem is when the foreskin is pulled all the way back, trying to get an erection hurts like HELL. Just below the point where the foreskin folds itself over, there's a semi-tight "ring" of skin underneath it. It's fine when flaccid, I don't feel any pressure or constriction. When it grows, however, the "ring" tightens and it feels like it's going to burst, rip and it's just.. impossible to go further. Very painful.
My second problem: The thing is, my girlfriend would like to start getting sexually active with me now. I kinda tried to have intercourse with her before I could retract, and I wasn't even able to sustain an erection long enough to insert it. I'd get an erection (not fully), put the condom on, and it would eventually go limp. I believe it's mainly because I can't really feel anything with the foreskin up. Is it possible to have sex with the foreskin unretracted? Why can't I maintain an erection at this point?
So I'm stuck. Is it possible to have sex with foreskin unretracted? And will my foreskin eventually keep stretching enough so that it doesn't hurt when I try to get an erection while retracted?
More stretching will help you to be able to stretch the foreskin until you can have an erection retraced. Until that point, having sex with phimosis (the term for an unretractable foreskin) usually hurts. I've read people saying that they can do it, with condoms on in particular. However, when I tried it hurt and it wasn't possible to do very much, if you know what I mean. You'll want either a circumcision or stretching in order to be fully sexually functional, I think.
I think you need some more stretching. Get an erection and then pull the tight part of your foreskin back agains the head and that will stretch it. Do that every day and it will permanently widen and become easier to retract.
The foreskin has more nerves than anywhere else on the penis and has the greatest sensation. You should concentrate on the sensations from your penis. I think your problem might be in trying to use a condom. Why not ask your girlfriend to have a IUD inserted or to go on the pill? Getting rid of the condom has to help.
After your girlfriend gets another form of birth control, you can try inserting your foreskin covered penis. Make sure she is turned on and lubricated before you try. Only insert as far as is comfortable for you. That means incomplete retraction.
I have phimosis too and the reason I found out was because I was having sex without a condom for the first time (I was able to maintain an erection!! Woo!!) During this though my foreskin retracted and I couldn't get it back (known as Paraphimosis). After an embarrassing but hilarious hospital trip (while on holidays overseas) I was back to what I thought was normal. As soon as I was able I did a Google search and found out that I was meant to be able to retract. 'Who knew?!?'.
I may have been told this in hospital but I do t speak German and there was a few slight miscommunications while he had my penis in his hands.
Anyway I've been stretching for only two weeks and can now retract reasonably easily. It's still just hard to get it back over. So for the foreseeable future I'm going to be putting my fingers into my penis hole and stretching the "ring" that you spoke of until it glides over the corona and glans like the majestic foreskin it is.
I've also read that your doctor can prescribe a cream to aid in the stretching so I might consider that now that I'm home. I'd suggest you go speak to your doctor if you're worried about it taking a toll on your sexual health/satisfaction.
I've just written all this and now seen it was posted quiet a while ago. So for anyone else having these issues that's my take on the situation.