Will it hurt?

So i haven’t had sex in over a year. My last boyfriend and I only had sex once and it was my first time (which hurt obv). He passed away 10 months ago when we were broken up. I haven’t been comfortable sexually with anyone since tho just cause I haven’t been ready. I’ve finally been kinda talking to this one new guy now and I’m ready but I’ve turned him down twice cause I’m scared it’s gonna hurt. Any tips?