I like this guy, and I've had sex with him once, but he

>>17785403
I feel you OP. I have a really shallow/generally small vagina. Sex in general is miserable.
The best thing you can do is get a dildo that's in between his fingers and his penis size.
Go from fingers, to dildo, and, once you're all warmed up, the penis.
Also maybe get a vibrator (EVA is a great hands free one) to help loosen you up from the nerves.
And make sure to communicate to him if he's going too deep.

>>17785410
I think my vagina size is relatively normal, the length isn't the issue, it's more the thickness that's the issue...

Use lube.
Seriously I have a friend that has like, a medically tiny vagina or some shit (if she ever has kids she has no choice other than a c-section), and every time she fucks she has to use lube because otherwise its too much.

No dick is ever "too thick" with proper lubrication and arousal. Your vagina is designed to squeeze out kids.

>>17785442
as in like silicon based lube?
We were already using a water based lube...

>>17785403
Maybe try more foreplay? My pain tolerance goes way up when I'm properly aroused, and your vagina will also relax.

>>17785477
You could try silicon based then, since it dries way slower than water based ones