I have a tight-to-relatively tight foreskin (I can open it pretty wide, but can't retract much. The picture on the Wikipedia "Phimosis" page is actually eerily similar to mine haha).

I have started nightly stretching very recently, and I will persist with determinating and patience. This weekend, I have an almost-sure oppurtunity to have sex with a girl (score!). I am 19, have had sex once before, but it wasn't a proper experience. Ironically, the girl was so tight (as she was a virgin, also) that she was the one scared of pain. Whilst there was vaginal contact, there wasn't eally penetration or any significant movement (any time I moved at all she was almost in tears, she was so tight).

What is your advice? Is there strong chance of injury, that will cause me a major setback?

Is there a reason you didn't mention condoms? Any idea of the risk in not using one?

A condom will be your best friend in this case is it comes to fruition. Leave the foreskin forward, put on the condom, and you'll find your foreskin's tendency to retract will be greatly restricted. Liberal lubrication will help with the penetration problem, and that is easily produced during your warmup act. Spend more time warming up!

What are you doing to stretch the opening?

Yes, I will be using a condom. So if I take it gently there is little to no chance of injury?

I'm using the exercise in the instructions, pulling the tips forward, as if holding open a bag

Well, at least that lowers the odds on hearing, "Guess what Honey!"

The condom should restrict the movement somewhat. Don't lubricate the inside. If you produce much pre-ejaculate, the foreskin may start gliding. Just take it slowly and you should be alright.

As Jim cites, the absolute priority in the situation you describe with the possibility of gratuitous sex, is contraception and protection - as far as possible - from sexually transmitted infection. Like it or not, you are "playing the field" and the rules of that game are that you do not acquire anything that will cause embarrassment when(ever) you eventually decide to "settle down" to a commitment. The two obvious such things that could cause such trouble, are child support responsibilities, and passing on to the "serious" partner, a STI which you did not even realise you had caught (because that is how many if not most STIs work).

And the point is, that a condom will - if used correctly with adequate lubrication - negate any such severe friction on entering her, as to force your foreskin back. While there may be some advantage to having your foreskin retract, it is absolutely not necessary for intercourse, so a condom is not only essential, but it is actually advantageous if your foreskin does not retract as your glans will not be irritated by the condom. (See also my reply to the discussion following this one.)

Now that matter of lubrication. If the young lady is actually enthusiastic about having sex, we might presume she will be nice and "wet" by the time that she permits it. So wet that it coats her whole vulva. Given the possibility that she is not sufficiently lubricated (enthusiastic), it is advisable to have some commercial lubricant on hand (or more precisely, kept in an inner pocket of your jacket at body temperature) to apply (on the condom or in her).

Clearly your previous endeavour was characterised by complete absence of lubrication which is the "magic" ingredient to successful intercourse (with or without a condom). She could not lubricate if she was in any way anxious about the situation - and you dramatically describe just that she was. And I fancy, the anxiety had many components and with excellent reason if you on that occasion were not employing a condom.

I even wonder - when you say she was "tight" - to what did that amount in terms of you inserting your fingers beforehand? (Trick question! )

I tried to have sex with condom and I've put it over retracted and non retracted foreskin over the glans .

With non-retracted foreskin and condom over that it looked silly and I could probably penetrate her without problems of hurting and others .

With foreskin retracted over glans and condom over that ,foreskin would always tend to retract and **** everything up (condom would lose it's position and it would stay unstable ).

I wonder can I put a condom normally without it falling of or being unstable .

I wanted to have sex with my glans uncovered because of the pleasure and the girl itself aimed for that ,cause it seemed logical and normal ...

Would I feel pleasure with non-retracted foreskin ?When I put the condom over non-retracted foreskin ,the skin of the tip of foreskin was improperly compressed and packed at the tip of the condom and I doubt my glans would come out inside her and during penetration .

I didn't have an intercourse because when I would put a condom my dick couldn't get hard enough to enter her .


Do you have any advice on how to put a condom properly and what to do with skin that retracts back ?

I didn't entirely stretched the foreskin and frenulum (which is still short ) and my opening isn't wide enough for retraction to be smooth .

This is something you'll need to figure out. Every intact men is different in degrees. Some have no issues with retracting and using condoms. Some complain as you do. The secret is getting a condom which will not ride forward as your foreskin glides. There are some condoms made with bigger headroom. If the part which covers the shaft is tight enough, that might work, but only your attempts at using will tell the true story. You could also try leaving the skin forward to see how the sensitivity really is. The deal with losing the erection is purely psychological.

- irrespective of whether your foreskin retracts or not - and even if you have no foreskin in the first place, so the concept of "logical and normal" loses any real meaning. Logical is that the condom is a must until you are married, and anyone who convinces themselves otherwise, need not get so fussy about how their foreskin functions.

Similarly, "it looked silly" really means nothing when it comes to a condom-covered penis.

Our standard advice for putting on a condom is - you get an erection, and you roll the condom on. That's it, that's all the instructions. No mucking about trying to pull your foreskin back, forwards, up, down or sideways, however it is when you get the erection, that's how it is. In almost all cases, when you are actually with a young lady (or might I say, even an older one ), you will be producing "pre-come" or "pre-ejaculatory fluid" (even if you do not at any other time) which makes the inside of the condom very slippery so that your foreskin will in short time move to whatever position - or range of movement - naturally suits it.

If the glans is sensitive and only the tip is showing, then that may feel uncomfortable against the end of the condom though almost all now have a "teat" on the end which should be clear of the tip of the glans at that point. It may be more comfortable to put a small drop of commercial lubricant into the tip just in case the glans is that sensitive.

The presence of the condom prevents much "drag" tending to push the foreskin back. There is always a risk that if the condom is insufficiently lubricated on the outside, it will either get pulled off the penis, or the vagina will resist its entry so that all the pressure of a thrust will be applied on the very end of the condom and it will burst. Either of these situations and particularly the latter, given just how tough condoms actually are, indicates a severe lack of lubrication.

A large part of the pleasure of intercourse is that you are having it with the girl. This is why fellows complain of "premature ejaculation" - it's not the physical stimulation, simply the excitement of being with her and being allowed to have sex, is the most exciting part, so in general, a little less sensation because the glans is covered will barely be noticed.

In your case, losing your erection when you prepare to have intercourse demonstrates another related effect - you are too anxious about actually having intercourse. This relates to an attitude that intercourse is the important part, and the badly mis-informed supposition that it is to the girl, even that important anyway (other than from eagerness to please you) as in actuality, she is not even particularly likely to have an orgasm from intercourse on its own. If instead, you concentrate on pleasuring her and let her put on the condom and direct you into her when she feels she is ready and only if she feels that way (which means she will not be overly "tight" as you enter), you are likely to have much more success. If at that point you do lose the erection, it does not matter; you simply keep your concentration on pleasuring her.