How do I set myself up to get over my fear of penetration?
Context:
I,18F, have never really fingered myself. I grew up in a religious household where it's looked down upon to masturbate, but I purchased a vibrator and I've been using it for a few years; however, I've always been too scared to finger myself.
I remember a couple years ago I was able to stick a finger or 2 in and it went all the way in, but now I can't even fully stick a finger in and I think it's mainly due to fear. I never really ventured outside of clitoral stimulation. I think my fear got worse after a past partner tried penetrating me but there was no prep (i.e. no lube and no stimulation beforehand) and it really hurt so after that I stopped trying to finger myself
This was just now, but I tried using a vibrator and then slipping a finger in. I was wet for sure,and the finger was going in but then it felt weird and I guess I got scared and then I felt resistance and it hurt so I took it out and then afterwards I got a bunch of anxiety and was met with more resistance so I gave up.'
I was with a guy (we've met up multiple times for this purpose) and we were dry humping and I felt the tip go in and there wasn't any resistance, maybe because I didn't expect it to go in.
Actual question:
All in all, how do I progressively overcome being scared of penetration? How can I ease myself into letting a finger in and so? I want to go to a gynecologist but because of my religious household I can't. I really want to be sexually active but I can't because of this. I see so many women inserting tampons easily and being able to masturbate and have sex easily and I want to be able to do that. Should I ask the guy I've been seeing to help me out a bit?