FYI, you can still get someone pregnant even if you don’t cum. Pre-cum often contains a small amount of semen and that can definitely be enough to do the job. Not to mention the fact that STIs are a potential concern.
I wouldn’t be having sex without a condom unless one or both of you has some other form of prevention, and you’ve both been tested since the last time you had unprotected sex, or relatively recently.
You don’t want to fuck around when it comes to potentially having a kid you’re not ready for, or getting an STI.
I would say I do that at least once every couple of weeks. It used to be several times a week, but I’ve gotten better at getting to sleep in general.
It’s still my go-to if I can’t get to sleep.