When it starts to hurt, when it feels uncomfortable, when your dick feels cold to the touch or when it appears bluish or purple in color -- WHATEVER you are using for a cockring is TOO TIGHT.
It is at this point that you should remove it.
Intense restriction such as you described for a short period of time in MOST cases is not going to cause permanent damage -- dudes play around with their dicks and the contents of their "home office" or kitchen junk-drawer all the time. Most of these guys do NOT end up in the ER with ruptured blood vessels or injured testes.
BUT SOME OF THEM DO.
So... it's up to you to determine how far you want to push yourself with this kind of stuff.
I've fiddled with rubber bands before -- and found them to be far too restrictive and uncomfortable. They also yank at hairs in a rather unpleasant manner.
There's literally a good dozen different varieties of cockring you can purchase which allow a user to alter the tension and at the same time provide a "quick release" mechanism for times when it gets to be too much. Velcro, snaps, "Japanese" rings with adjustable sliders... all a good option if you want a REALLY tight ring that is safer than a rubber band and can be removed quickly.
Rubber bands can cause so much swelling sometimes that the skin surrounding them puffs up and it becomes nearly impossible to remove the band -- cutting it off would be required. Sliding a pair of sharp shears under the band and under all that swollen skin... eh... well, I just don't want sharp things near my dick like that!
Someone here once mentioned putting those blue rubber bands from broccoli bunches to use as cockrings. I haven't tried it yet, but the slightly different type of rubber and texture of these bands is probably much more suited to that purpose than an "office" rubber band. They're more flexible, soft and pliant.
Bottom line -- it's unlikely you're going to get seriously injured fucking around like this. But it is NOT out of the question. You do this AT YOUR OWN RISK. I would personally stay away from it.
Purchased cockrings are much safer, if you ask me. They also LOOK better and there's more variety. If you tried them before and didn't get any benefit but yet you enjoy the rubber band -- quite simply you just didn't use a ring that would get as TIGHT as the rubber band. There ARE rings that will get as tight as you want them to be -- you just need to find them.
I USED to like fiddling with a VERY tight cockring but found that after a few repeated erections it became more and more difficult to get hard again with a tight ring. Now I stick to using the medium setting. I like how my dick looks and feels this way more -- and I am never uncomfortable.
There are times, every now and then, when just for the hell of it I feel like fucking around and making my dick outrageously hard, either jerking off or with a partner. So I WILL go for it by tightening the cockring (you can also wear TWO cockrings if you get the right kinds) -- but I only do this for a FEW MINUTES at most. Once I feel that the blood isn't circulating properly -- I ditch the rings.
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