i just first want to say that a while back i diagnosed myself with phimosis after noticing that the pictures i've seen here and there around the internet didn't resemble my manhood. i soon realized that the foreskin was supposed to be able to retract behind the glans and that eventually led me to here. i've learned a lot about phimosis and stretching techniques were a lot more comfortable than the other method of simply pulling it back consistently.

it's been a while but i have recently been able to retract the foreskin while flaccid rather far back but im a little bit too scared to go all the way behind the glans. i realized how sensitive my glans are though almost to the point of pain when i touch it. will this sensitivity improve later on? also, i can't retract my foreskin while erect. am i supposed to continue the stretching techniques of pulling the phimotic ring laterally? i feel that putting the foreskin behind the gland provides a more uniform stretching but im not too sure how to continue from here.

One other contributor has found that a warm bath relaxes his foreskin and makes it easier to retract. You might try that. Don't be alarmed if it appears to get stuck. Just use the same diligence to get it back over.

Using the lateral stretch is the most effective way to enlarge the opening. It sounds as if this has worked well for you, so keep doing it.

You are making a cardinal mistake.

You are saying the glans is sensitive when you touch it with a dry finger.

Your glans is not supposed to be touched with a dry finger. Had you any experience with a young lady, you would (presumably) have found out in no uncertain terms that her glans - the tip of her clitoris - is not supposed to be touched either - without lubrication.

Lubrication is perhaps the most important thing about having sex.

Your glans will become a little less sensitive as you progress with the retraction, but keep in mind that this sensitivity has not stopped you masturbating effectively in the past, so there is clearly nothing "wrong" with it. On this basis, if something makes the glans hurt, then you are doing something wrong. If you specifically wish to touch it, then use some lubrication - the very same rule that applies to pleasuring a woman.

Since you have observed that stretching as we explain here - pulling the foreskin outward with the fingers - is both immeasurably more effective, and more comfortable than simply retracting, then that is what your should continue to do. Note that you must be getting your fingers fully inside the foreskin, beside the glans (but avoiding touching it as far as possible) to stretch. This will provide a quite uniform tension. Try up-and-down as well as side to side (and do the frænulum stretch in advance of discovering whether it is necessary in your case - it probably is).

The sensativity that I had seems to be getting better.
I started in the tub retracting while flaccid in very warm water.
Got to the scary part (for me) of getting a semi errection while retracted and it was fine.
Progressed with that for a bit in the tub and got to a point where I could get a pretty decent errection while retracted.

What I do now is what I did in the tub but now I do it out of the tub (getting a errection retracted)
First I retract in the tub, then I'll work on getting an errection/letting the sensative inner skin dry out. I find that putting the skin back forward is what causes the most discomfort but it's getting easier everyday. What I have done is put oil (I use extra virgin olive oil, lol.. but Jim said salad oil heh) on my inner sensative (pink) foreskin and head before I pull it forward.

Then I'll pull it back again to expose it to the air again, oiled.
I've found that in a few days it's gone from literally a drop of water feeling like the worst thing in the world to being able to have my retracted penis under a stream of water without too much discomfort.

Even able to touch that inner foreskin with a oiled or wet finger O_O that was not possible without an insta-flinch before.
So yeah moral of the story is it seems to get less sensative with exposure so far.

I still need to work on increasing the opening and I think the frenulum is tight because I noticed when I pull the foreskin back further it starts to pull the head down lol. But I think you're expressing what I was at the time... the sensativity was a bigger concern at the moment... because I was like what's the point of retracting if you can't even put a drop of water on it without pain? :P

Off topic question for anyone who knows.
When I checked out my frenulum and the ring it seems like they are connected, is that usual?
What I mean is it seems like the frenulum's area of attachment into the foreskin is the tight ring. So it makes it hard to determine which is tighter lol. I can see the frenulum pulled sometimes but I feel it more like it's the ring that is getting stretched with an errection.

Is there a different sensation when the frenulum is stretched vs the ring? Because it feels like it's still the ring but once I felt more of a warmness to burning sensation that seemed focused under the head and I think that was the frenulum being stretched?

I am afraid that you still seem to be thinking in terms of retraction - and the sensitivity.

My suggestion was the you focus on the stretching exercises we deal with here. Clearly the foreskin opening and the frænulum are part of the same structure, both need to be stretched but retracting is merely the test for progress, not the means.

You are quite on topic with your question. Yes, they are attached, and yes, they both need work. I think you should be able to distinguish what is getting stretched while doing it. However, there will be some distortion of that feeling because of the attachment.