5950GTS - If you follow my posts you will see that I have given a lot of advice to guys who can't retract their foreskins. The problem is due either to a too tight foreskin, or a short fremulum (the stringy thing on the underside of the foreskin, attaching it to the shaft). The remedies are: 1. Gently stretching the foreskin, for a month or so, several times a day, using hydrocortizone cream on the head and foreskin, or even olive oil. 2. Getting a frenuloplasty, the lengthening of the frenulum. 3. A circumcision, which can be done with a "loose cut", leaving much of the foreskin remaining, but retracted behind the glans. 4. Do nothing, but you will have much better sex if you take care of this problem, which affects about 15% of uncut guys. PM me if you want to discuss this issue personally. I am a lay sex therapist, and could certainly help you resolve this problem.
Well i doubt it`s the fremulum. I don`t know why but i doubt it`s that. The problem is that the top part of my foreskin the one that goes over the head is too tight. I was able to retract it when i was young but it was still tight.The foreskin itself moves over the head and all but that too tight part prevents it from going down. If i pull harder..well i never did because it probably hurts. And hey i don`t have any sex so for the moment there`s nothing to improve. (joke)
Try the gentle stretching exercises several times a day using hydrocortizone cream on the foreskin and head. Many guys have found that a month of this stretches the foreskin enough to be able to move it past the head during intercourse. Some guys find they can do this but it is still too tight around the shaft after retracting it. You might also try olive oil, which is often used for skin massages and is good on the skin. Be sure to wash afterwards, although much of the olive oil is absorbed into the skin. Consult a doctor and go over your problem with him, and see if he recommends circumcision. There is nothing like a personal examination by a urologist or other physician to determine how to address the problem. Internet help can only go so far.
If it gets hard and sorta straight, it'll go in ok - make sure she's good and wet, or use lottsa lube. The vagina is wonderfully accomodating, making room for all comers (pun intended.) But by all means take Cutted's advice about stretching with oil. I got it back when I was younger and masturbation with a full stroke kept it flexible enough for life. If you've been able to orgasm from masturbation, you'll get lottsa jollies from sex, but still, a fully retractable 4skin is better. g'luck, mate!
If you cannot retract your foreskin during intercourse, there is nothing to keep you from inserting it covered. The only problem is lessened sensitivity on the head if it is not directly (or through a condom) contacting and frictioning with the walls fo the vagina. Fastswitch's advice is good - he has been where you are.