i really need advice ladies!

So, kind of recently, me and my bf have been a little irresponsible when it comes to safe sex, every once in a while became more frequent. He would always pull out before he was remotely close. Recently we tried to use a condom and he was unable to get off whatsoever, we tried to get him to finish for about 20 mins. He wasn’t able to, i was eventually able to finish him by jerking him off any advice as to what we can do to get him back to being able to finish with a condom on? it was never an issue until the unprotected sex became more frequent.