Faggot ejaculation

Hi Sam.
Im a faggot in chastity. I want to get to the point of being able to cum from just my ass being used. At least in my experience that is easier said than done. My idea is to just keep locked and eventually I will cum while being fucked or have a wet dream or something. I know from experience that I will have to stay locked for over a month. (My current chastity lock up record is a month). I think I am just scared I will never cum again. It’s not necessarily a problem if I don’t cum again but I do worry about any potential health issues. I think I am looking for reassurance and if you had any advice or similar issues.