Brief Answer:
You can undergo a partial Circumcision. It wont be very painful

Detailed Answer:
Hi, the way you explain it you do have Phimosis.
You might get pain or bleeding due to tear of prepuceal skin during forceful sexual activity.
You can start massaging it front and back action with some oil. This might help but other than that there is not much you can do to cure it.
I suggest you go in for a partial circumcision. It is a minor surgery and since you have six months to marriage it will heal up well by then. In partial circumcision we dont remove the entire foreskin but only the tight band part of it. As a result, The normal penis head(Glans) is covered by skin but in erect condition the skin automatically goes back without pain. The scar is also not bad. You can consult a Plastic Surgeon or a Urologist or even an experienced Surgeon can perform it for you. All the best.
If you do not want to get operated that would also be fine.
Probably with time it might loosen up a little bit but not as good as a partial circumcision.
Do let me know if I can advice you any further.
Take care,
Dr Rishi, New XXXXXXX XXXXXXX

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Brief Answer:
Foreskin getting loose is not very common.

Detailed Answer:
Hi, Thanks for the reply.
Without examining you it is extremely difficult to say whether it will improve with time. But I have seen in some cases that if there is no tight band around the corona then over time and with repeated sex the foreskin can get loosened. But in your case I doubt that as you are already 27 and if it had to loosen it probably would have. But the final word can be given only by examining you and ruling out a tight constricting band. Therefore, you could examined by a Surgeon who would be able to tell you about it. If I could examine you I would tell you in a minute whether it will improve or not.
As for sex with condoms, it is possible that if the condom is fitting well it might not retract the skin and you could have comfortable sex. But if the skin retracts even with the condom then it could be painful for you. Second problem with a forceful retraction is a condition called Paraphimosis. This happens if the prepuceal skin retracts forcefully and then cannot be retracted back in front due to the tight or large glans. This can lead to painful swelling of the prepuceal skin and then an emergency forward traction has to be done or emergency circumcision or there could be gangrene of the glans. Therefore, keeping all things in mind you should consult an experienced Surgeon.
Take care,
Dr Rishi, New XXXXXXX XXXXXXX

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