I have a tight foreskin.

It retracts halfway or so.

I have been doing two sessions of stretching a day for a few weeks and it is helping me.

When putting on a condom is it better to retract the foreskin as much as is comfortable and then roll the condom down?

I do notice that when I don't retract it I tend to take ages to orgasm - not necessarily a problem, but not always beneficial either.

Thank you.

Foreskins and condoms can present interesting challenges because they all tend to be somewhat different in how they interact. Some intact men can use condoms with the same ease and success as do circumcised men. Others have nothing but difficulty in fighting off the tendency of the foreskin to bring the open end of the foreskin forward on the shaft during trusting, eventually causing it to come off.

In your present state, it is probably safer for you to leave your foreskin forward, using the condom to lock the foreskin in place. Not lubricating the inside will help. Hopefully, having the skin forward along with the rubber sheath will not insulate your nerves so much that your feelings will not be sufficient to trigger an orgasm and ejaculation. You'll just have to try it.

I'd also recommend trying retracting partially to see how it goes. Please let us know how it goes. With this method, there is some risk the skin will decide to go all the way, possilby causing some distress at a moment when you don't want that to happen. Going easy will help to prevent that. However, in the heat of the moment, getting to the climax is the goal, and once in pursuit of that moment, one will do what is necessary to achieve it, even if getting rough is what does it. That could force the skin back. In addition, there is also risk the condom could be forced forward as the skin returns forward.

Experimenting with different sizes of condoms is also recommended. It is definitely not a one-size-fits-all deal. One which hugs the shaft is probably most desirable. My thought is that the newer varietiies with large head room are ideal for allowing free movement of the foreskin inside the condom. Trojan makes one called Maxum Ecstacy.

Continue on your stretching regime. Use our recommended methods with necessary adjustments to your anatomy and state of tightness.

Condoms do not feel natural. However much well-meaning health promoters try to say that sex (intercourse) is the same with a condom, you can feel the difference and condoms are generally uncomfortable. And this will be the case whether you have a foreskin that retracts, one that partially retracts, or no foreskin at all. On the other hand, if your foreskin will not retract at all, the condom will likely not be particularly noticeable as it is not coming in contact with your glans.

So the reason for the discomfort is the particular unyielding texture of the condom. To the extent that this is a problem, the common recommendation is to put a small dob of lubricant on the inside of the tip of the condom to smooth its contact with the glans. As you proceed with intercourse, your own lubrication will generally serve this function anyway (but even then, the effect is imperfect) and my observation is that you produce much more pre-ejaculatory lubrication ("pre-come") when actually with a young lady, than when masturbating alone.

It is also noticeable that as you ejaculate, the semen is very sticky and the presence of the condom is again felt at that point.

Another consequence of this natural lubrication is that shortly after initiating sex, your foreskin will become freely mobile within the condom and find its own "preferred" position allowing that the condom largely defeats the tendency for thrusting to pull back the foreskin. Therefore it really does not matter much where you place the foreskin before putting the condom on, so the complicated instructions commonly provided for putting a condom on with a foreskin are plainly confusing and counter-productive - most likely written by people (American) who have no experience of a foreskin anyway.

I therefore summarise: Get an erection; roll the condom on; proceed.

What is important - critical in fact - is lubrication on the outside of the condom, hopefully provided in adequate quantity by the young lady, but otherwise supplemented by a commercial lubricant which should always be "on hand".