Going soft

[Mystery Man]

I'm not speaking from experience here, but perhaps don't rush back in, but do something a bit less for a while like just fingering, one finger first then two, and be sure he's comfortable with that. Try and get him to a state where he really enjoys the anal stimulation of something slightly smaller and is really keen to step back up to the real thing. Then make sure you take it slow, lube up and are really considerate. It seems from the whole tone of your question that you are a considerate guy so that shouldnt be a problem.

One other thought, which both of you would have to be happy with, but how about swapping roles - perhaps you've already done that

yer he started with me first, but then i tried him n it hurt him so i went soft n then he was up for it again another time but i wudnt even stay hard