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So here is my situation, I'm uncircumcised and when I go pee and stuff I can pull my foreskin pretty far back, not completely off the head but close. When I'm erect however it goes maybe 1/3 or 1/2 the way down and it's tight, it hurts to go any further. In the shower I can't really wash it because my head is very sensitive, I'll let some water drizzle over it and that's it. Smegma build up isn't an issue, I don't see any in there, penis smells clean all that good stuff. My issue, or rather worry, is that a blow job will hurt, or that sex will hurt. Anybody in a similar boat that has received oral/ had intercourse? I don't mind the tight foreskin, I'm just worried of possible pain. The reason I'm asking is because the girl I'm currently seeing wants to take things further and this has always made me back out, but I really like her so I assume I'll have to get over it eventually, I'm 19. Any help/stories appreciated! thanks.

To clarify, I am going to start working on stretching the skin so that it retracts fully, but becoming sexually active is something we both want now so I'm more interested in what to expect in my first sexual encounter in my current state, not so much how to retract it. Thank you again

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Count yourself lucky that the girl has been so understanding. Hope it goes well!
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I have the same issue? What do I do? I mean I thought about getting circumcised but I don't know. My head is pretty sensative during oral sex to the point that it hurts and I can not ejaculate. I can keep hard but I can't ejaculate. What can I do, I guess I'm frustrated at this point.
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It depends on how tight your foreskin is. If it is really tight it won't retract when you penetrate and all will be well.

On the other hand if it is only semi-tight, then it may retract behind the head when you penetrate and that may be painful.

The solution is to widen your foreskin by stretching.

A few men live their entire lives with a non-retractable foreskin. They can masturbate, have penetrative sex, get married, and father children with a foreskin that does not retract. Some believe that a penis with a tight foreskin is more sensitive and that sex is better. However, most men prefer to make their foreskin retractable.

Almost all boys are born with a foreskin that does not retract. This is normal. It takes years for the ability to retract to develop. About ½ of boys have a retractable foreskin by 10.4 years of age. Many adolescents still have foreskins that have tips that are too narrow to pass back over the penis head. These foreskins may be gently stretched over a period of time to cause them to widen.

You are normal for your age. Your foreskin is still developing. You can help it develop by stretching it.

When your penis is erect, gently pull your foreskin back against the head of the penis. As the head attempts to pass through the foreskin it will stretch the skin a little. Do this every day and in a few weeks or months your foreskin will widen and you will be able to retract your foreskin. Do NOT force retraction.

It works by tissue expansion. Stretching skin induces “mitosis” which is a word that means “division of cells”. New skin cells are formed and the skin expands but it takes some time. The increase in size is permanent. Be patient and let mitosis do its work.

The important thing is to put the skin under tension every day so that it will grow wider.
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Hi Dinky123:

The foreskin protects the head of the penis and keeps it moist and sensitive. If it hurts, don't touch it. Keep your foreskin forward to protect the head. It will probably get less tender later.

It is normal for the glans to be sensitive because your foreskin has been protecting it for your whole life.

You do not have to retract your foreskin to receive oral. The foreskin is filled with nerves and loves to be sucked. Just tell your girlfriend to not pull back your foreskin and keep it forward and suck on the foreskin.
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