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My glans is engorging, but it is soft, meaning it will buckle when I try to enter. Which makes entering painful and more or less impossible unless the women is very very wet.

Using lube helps but it is still a bit frustrating.

I might try rings next, but they usually worsen the situation bc of restricting blood flow...

Rings work. It's the only thing that works for me. I have a severe leak. Have to be tight though.
I start with a loose ring to allow greater inflow, and then use a tighter ring once I achieve... 70% or there abouts to further restrict outflow.

Lots of trial and error.

Firm glans at the end of it. Worth trying. Combing with oral drugs helps.

I've had very good success with Giddy, a modified ring. It's not round - neither is the penis. It's sort of oval with two nubs at the top which restrict leakage from the dorsal veins. I think the nubs are critical. It;s open at the bottom to allow seamen to escape. The ends are held together by one of two rubber bands.

Sizing is critical. If too tight it cuts blood supply. If too loose it doesn't contain blood. I actually have several. For exercise/health I use a number 3 (C) with the tighter of the two rubber bands supplied.

If I happen to inject Trimix and use the Giddy too, I use the largest ( 4 or D) with an ordinary rubber band so I can take as many loops as needed - but not too many.

Lots of folks have commented they didn't like them, but it works for me. And works well.

It is expensive. I think you can order one and get a one time size exchange.

The problem in sizing is you need a fairly good erection to get an accurate measurement for ordering.