Just have your birth control in place then feel free to use him for your first experiment with "going all the way."
As for veggie dildos, a zucchini or carrot can be carved down to size.
It’s difficult to be a true sexual black belt without empathy for your partner.
While you are practicing penetration, be sure to have your orgasms in place.
Nearly all vaginal entrances are small and/or partially hidden.
First off, this requires a discussion between you and your BF before you are in the throes of sexual passion.
If you've had an orgasm with yourself, you're not a virgin.
Learn about your own body by exploring masturbation including vaginal penetration.
My answer is YES, take your own virginity.
It sounds to me as though you might be dealing with a stubborn hymen that might be especially thick.