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I tried a pump and ring in 2018. Didn't seem to do much and a hassle. Threw it all out once I started on Sildenafil . Now that the Sildenafil seems to have lost effectiveness for me, what about Cialis and a ring?
With any of the drugs you have to have stimulation/arousal, but assuming you "handle" that, the ring mainly helps sustain the erection?
Once I'm stiff enough to begin intercourse there are no further problems, but don't want to lose it between the bathroom and the bed.

As a supplement boost to injections I use novelty (sex shop) rings. When using a VED to achieve an erection I use medical grade constriction rings. Pills alone won't give me any erection so I don't have experience with that.

Yes a ring will help you maintain an erection. I used to use one when I was injecting Trimix. Two things about that, #1 is make sure you trim or cut hair because pulling a ring off tangled in pubes is painful. #2 If you inject move further up so the ring doesn't end up on the injection site. That's quite painful too.
My favorite was a silicone ring that wrapped around my sack and penis. Sometimes I'd place 2 rings on, a smaller one mid shaft. The wife liked that!