The key for hubby is lubing up with silicone lube before sleeping, otherwise the ring pulls painfully hard. With lube it just slips a bit and while not comfortable for the bit his cock is straining, it’s totally manageable.
He’ll keep the lube by the bedside and just squirt a bit on if needed too.
Also with time, your body adjusts, so you will get used to it, yes.
Hope that helps,