Yeah, I do think that’s a good idea. Exploring penetration on your own is a great way to prepare to be penetrated by a partner. I’d recommend you get a Tantus Compact or Small Silk if you can, or even a dilator set; any of these could help you get used to penetration. (Make sure you’re always very turned on, well-lubed, and stimulating your clit while you try this stuff.)
There’s also a possibility that you might have a legitimate problem, like vaginismus. It’s more common than you’d think. It might be worth talking to your doctor/gyno about your tightness and pelvic pain.