The First Time in a Relationship

I just started seeing a new guy and have already decided that I don’t want to have sex with him right away (I’m far from a virgin though, so this isn’t about virginity at all.)

The problem is, I’m not sure what I’m waiting for, and the answers I get are always arbitrary ("wait one month"), not so feminist (wait til you’re married or you’re a whore), or vague… "it’ll feel right to you."

It actually never feels like "the right time" to me. I’m a survivor and I’ve had other bad experiences with men. I still enjoy sex and want to continue having it, but I just need help figuring out what "the right time for me" is because I don’t have much experience with healthy relationships. I think there are conversations that I should have with him to help me decide when the right time is, but I don’t really know what those conversations are.

So does anyone have suggestions of questions and conversations two people should have before first having sex with each other (aside from STDs, birth control, and what we’d do if I got pregnant)?

I heard somewhere that a couple should talk about what each of their expectations for the relationship after the first time are. That’s the kind of thing I’m looking for.

Sorry for being kind of vague and scattered, I’d appreciate any advice anyone has for me!