First time jelqing - Need some advice

So, I decided yesterday that I would give jelqing a try, and decided to start by this morning.

I measured myself and on tops, meaning my erection is of highest quality I have these measurements:
5.3” BPEL x 4.5”

I have been quite insecure about my dick size ever since I was 15, I am 20 now.
Today, I did a newbie routine, warming myself up for 5 to 7 minutes with a hot/warm washing cloth. I stretched for an additional 5 minutes, which to be honest, I did barely feel. I have tried pulling a bit more while going to the left and right, up and down. I did helicopters and some diagonal stretches. Most of this was done completely flaccid to 40% erection because of safety. Eventually, as I pulled a little harder, during a full stretch I felt it stretch slightly in the base of my shaft.

Then I continued with jelqing, I already had a hard time getting my erection to 50 - 70%, but it got up quite quickly. With lube, I started jelqing with form I saw on instruction videos and applied slight pressures, my strokes took 3 seconds exact as I counted. I immediately noticed I got softer quite fast, so I had to stimulate myself multiple times to stay on a certain level.

After not that many reps (I think around 10 to 20), I felt as I stroked up, a small pressing pain in the top of my penis. This felt as if the blood was actually pushing into the top. I thought to myself, pain is no good, so I started to apply even lighter pressure. I felt the pain 2 or 3 more times, it was really minimal, but feel able and uncomfortable. After this, my mind was really off of it, I went flaccid, and with stimulation I only still got around 30% erection which quickly went soft again.
I stopped and did a warm down. Because it was my first time, I tried to get hard because I was a bit concerned about the small pains. I succeeded in getting a 100% erection, which immediately went down after stimulation stopped.
I do not feel this is because of damage, I was really just not aroused at all, and feeling somewhat worried, which can also carry a lot of effect towards my erection quality and duration.

What could I be doing wrong to have this minor pain occur in the top of my penis? I am really skeptical still with jelqing/PE, but as kegels have proven effective for my premature ejaculation.

For anyone thinking about doing kegels, do not think twice, just start doing it.
I went from a 2 to 3 minutes before orgasm (which I believe was also a bit of a mental thing), to a solid 20 minutes at least. I have even had round of 35+ minutes, if I wanted to keep it that long. This has improved my sex life insanely much as I get to fully satisfy my girl.

Anyway, ideas and thoughts on my jelqing case here?

UPDATE: I have some slight discoloration (reddish) slightly on the right side, under my glans. Is this bad?

What hand positioning you’ve been using for jelqing?

Jelq with an erection level between 40 and 70%. Do not grip too tight, just enough to feel blood moving up the shaft. When stretching, grab your shaft about one inch below the glans and do not pull too hard, just enough to to feel a slight stretch. Let your PIs be your guide as to how hard to pursue your routine.

All of this stuff takes time to learn how to do. I remember when I first started I would freak out at every little thing. What’s that? Can I still get hard?! Omg I’m freaking out and I can’t get hard (because I’m freaking out).

These days I have really learned and continue to learn the instructor and outs of the excercise and I am so confident in what I am doing that my cock live what I do to it and presents itself well ( ecaue I am relaxed)

So best advice is to relax, take it slow. You will learn alot about how the perfect is is built and what you can do to effect change in it.

Mostly just the standard jelqing ‘OK’ grip with my handpalm facing away from me, to get a better grip as close to the base as possible. Is using the grip with palms facing me also a good way to do it? I think I find it a bit more comfortable to jelq straight forward then downward.

Thanks for the tip! So the grip should really be a very firm press instead of a slight pinch with the OK sign? Like a massage? I think that would take away the pressure I feel in the glans, but just want to make sure I am doing it right since doing it for no results at all would suck of course.

Man, I feel you. I was totally freaking out as soon as it went down and I was like “Yep! It happened! I wanted to be careful, but now I have ED. How am I even going to tell my girlfriend.”
Luckily it was up and running as soon as I got myself to calm haha.

Update though: Discoloration was gone within an hour, no idea what it was. My erection 2 - 3 hours later felt somewhat sore, like getting your second erection immediately after your first orgasm. On a side note, it seemed a bit more straight than normal and a little more pumped, is this normal after a jelqing session?

With your palm facing up is underhand jelq and is known to cause pain or light discomfort to the upper portion of the penis, when not executed correctly or with too much grip pressure.

The opposite option is overhand with the palm facing down. Not doing properly can also lead downhill but the chances are more optimistic when we jelq overhanded.

Another clearly advantage from the overhand positioning is the starting stroke. The little, ring and middle fingers are out of the way, allowing us to grip deeper and start the stroke on the very base of the penis.

To be honest with you. This shit works.
I am into PE for less than a year now regularly.
When home for PE without counting till my arms pain then I stop. Whenever I go to pee either at home or outside I do stretching before and after urinating.
Recently my GF told me that it’s fatter than before. This statement gave me more confidence and evidence that it works. When you look at your penis from the top you can’t see any growing ;) but looking at it in a mirror can show you the progress. Depends of the angle you are looking from.

This works if you are patient and doing it wisely.
Believe in it to get resukts. If you have doubt you won’t go that far and you will certainly quit.
Wish you the best in your journey
Before I forget my piece of meat was 5” and something. Currently 6.3”

See if your grip while stretching is right, and also, In my opinion I think that 5 min stretching at the start could be a EQ killer.

Thanks for the advice! I meant I did the overhand at first, I understood already its better since it is easier to grip deeper so I will continue with this.

Shit, that is some real gains there! I have discussed this with my girlfriend, but she has more often told me how I should not do this as she thinks it is dangerous or painful.
Yes, whenever I mention if she would mind if it would be bigger, she thinks for a second before talking me out of it, that’s quite a hint ;)
Luckily with my current size I am able to get her off, she has had quite a lot of sexual experience, and with my smaller than average donger I was able to give her her very first penetrative orgasm (took 5 months though, but hey, need to praise yourself for something)

Thanks for the inspiration though, I have certainly not thought yet about stopping. Only problem would be to try and get my PE done while she is with me, stealth mode. I know she will like the end result though, so it is worth the hussle!

I will certainly do a double check, and you are right, I think I will also lengthen my stretching time a bit! Thanks!