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.
Perhaps it will help if you add your PC muscle in the penetration process.
As soon as any girl masturbates to orgasm by any means, she is automatically sexual in my book.