Hi stevienicksfan, welcome to the boards!
It's important to pay attention to what your body tells you--if inserting more than one of your fingers (or another item that's larger) hurts, that likely means you need to change an aspect of your insertion. That can look like using water-based or silicone-based lube. (You can learn more about lube here:
Lube 101: A Slick Little Primer). Sometimes, the lubrication from our own bodies alone may not be enough for insertion to feel just right, and that's completely normal. Have you been using lube whenever you're doing insertive sex? Another change you can do is to diversify the way you masturbate; instead of only relying on your figners, for example, you can add clitoral and/or nipple stimulation to the mix. There are lots of ways you can masturbate if insertion isn't currently working for you.
Additionally, there's also a possibility that the "something" you could push on during insertion is your cervix, which is the base of your uterus. You can check out our article about the vulva and vagina here:
Innies & Outies: The Vagina, Clitoris, Uterus and More
Vaginismus is a psychosomatic condition, which means there's an underlying psychological factor that causes vaginal insertion. After reading
this article about vaginismus, would you say any of the things mentioned here apply to you? If you've had some distressing experience related to sex and/or you were taught that sex is taboo/"sinful", you might want to talk to a gynecologist.