Well it depends on how intensely you can contract your pelvic floor muscles and how often you contract them. I personally, have gotten much more in tune with, and much stronger in a little under a month. I can feel noticeable and significant travel of the pelvic floor and intensity moving ever closer to my scrotum and away from my anus. (Although I will admit that I have become almost obsessive in doing them almost all of the time day and night. Call it an addiction

)
As you get stronger, you will feel less and less contraction near the anus and closer to the front of your body. You will feel more and more blood movement within your penis and the "squeeze" near the bulbs of the CC and CS. (See images of pelvic region anatomy to see where I am talking about)
I have also noticed, for me personally anyway, that there is a definite feeling of two-stage contraction. (Now in hindsight I realize that when I first started contracting my pelvic floor muscles, I didn't even feel the second stage of contraction.) The first peaks in intensity when the most stress moves from anus forward to the scrotum, and there seems to be a kind of stop sign or speed bump there

Then if the intensity of the contraction is increased beyond that you will feel almost as if the contraction moves outward along your penis to the glans. (this contraction does not really happen! It is a feeling caused by being able to contract hard enough to push blood forcefully all the way to the end of the glans)
But no one can tell you how long this will take or exactly what it will feel like for you. I was more clueless about kegels than probably anyone, but I just did them anyway, relentlessly. And the strength just keeps getting better.
I would say just do them, do them as much as you can. From my perspective, if it helps, this is what I felt from the beginning:
At first, I almost felt nothing but a "clenching" of the anus.
After about a week of doing them obsessively, I could feel that it became most intense midway between my anus and scrotum.
As I got even stronger, I started noticing that the feeling kept moving forward, and kept moving forward the stronger that I got. And I started noticing a clear feeling of the pelvic floor lifting up.
Where I am at now, about a month in:
The feeling is of significant lifting or raising of the pelvic floor so that when I "relax" or even do a slight "reverse kegel" immediately after doing a kegel, it feels like my pelvic floor drops an inch or so. (It doesn't move that much, but it definitely feels like it falls dramatically)
The first stage of controlled contraction feels like it is most intense right at or in the scrotum itself (or maybe the point where it is attached at), but I actually feel a rise in my testes as well. Then it sort of hits a wall or tough spot.
Then I can contract further and I feel the mass of intensity move out of the scrotum and "slide" along the shaft until it reaches my glans.
Note: the speed bump, hiccup, or whatever at the scrotum only occurs when gradually increasing the contraction. If I do a quick intense contraction it goes all the way out to the glans, but it is not as intense as gradually increasing the intensity.
Maybe from the above you will be able to identify moments when your pelvic floor muscles are getting stronger.