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What am I doing wrong? Following exactly the directions on many YouTube videos, but the rim of the pump digs into my skin and almost feels like it's crushing my bone when I pump for a while. Anyone else experiencing this?

Maybe you are either going too fast, pumping too hard, or using too much vacuum?
Depending on the pump you're using, one of these may help. Works well when I use a VED with rings. Haven't tried it with a regular vacuum pump.

http://uandmetime.com/products/store/#e ... ct=4958534

Does your cylinder have a wide rim that fits over the end of the cylinder like the ones on this web site: https://www.amazon.com/s?k=augusta+medi ... 93m6siad_b

If. Ot, you might want to consider one that does.

AnotherOldMan wrote:Maybe you are either going too fast, pumping too hard, or using too much vacuum?
Depending on the pump you're using, one of these may help. Works well when I use a VED with rings. Haven't tried it with a regular vacuum pump.

http://uandmetime.com/products/store/#e ... ct=4958534

how can one use "too much vacuum"? I just use it as per the instructions. Pump 5 seconds, pause 5 seconds. But with every pump the rim digs in deeper into the skin since that's essentially what removing air does, so it hurts more with every pump.

I agree completely with other commenters.. you can try using one of those collar type things that
help distribute the pressure against the pubic area... and... above all.. reduce the vacuum and time under
vacuum. the 5 second thing is merely a suggestion. 4 or less might very well be appropriate.. especially when
you first start pumping. I've been pumping over 3 years and i can't explain the physiology ,,,,, but,,, some kind of
conditioning has definitely occurred in that i can pump higher vacuums and longer times with comfort now than i could when
first starting.

That should probably be read as: Pump 5 seconds and then release for five seconds. Not pump up for 5 seconds, pause and then pump up another 5 seconds on top of the previous pump up.

how can one use "too much vacuum"?

Unless your pump is vacuum limited it is very easy to over pump, especially when new to using a pump.
Something is wrong when you start your question with, "Pump hurts...".
That said, some cheaper, sex shop, toy pumps are poorly made with little or no quality control.
Some can have sharper edges and need some "cushion" between the pump and the "pumper".

Would help to know which pump you are using.

I'm using Osbon Esteem. I assumed for $300 it would be considered top quality.

I really don't understand why this hurts. I pump only twice very slowly and I automatically feel a discomfort in my pelvic bone around the rim edges. As if it needs cushioning or something. Unfortunately it doesn't come with any cushion and I cannot find any cushions online for these types of devices.

Go here: https://www.erecaidpumps.com/ as linked on the sidebar on this page as a site supporter. Search for "V.E.D. Body Shield". You might also want to look at the "Easy Seal".
I have no personal experience with either product. I have enough of my own padding.

You can also look elsewhere for the "Encore Body Shield" found elsewhere. Looks to be nearly the same as the "V.E.D. Body Shield".

Osbon Esteem

For that price($300) one would reasonably expect the pump to work as well for you as it has for many others.
I "assume" you are using the pump with the insert(s).
Is there a money back warranty time frame?

I hate to think of a man spending that kind of money on a pump and then not being able to at least experiment with it.
Maybe a body shield like bldoink suggested would work? Seems like a small investment next to the cost of the pump.
As I previously mentioned the penile foam sleeve has greatly reduced the discomforts of using a pump and ring(s) for me.
I see they also offer foam washer. http://uandmetime.com/products/store/#e ... ct=4958536