Every woman should penetrate her own vagina for the first time. Clitoral stimulation with vaginal penetration - the combination orgasm - is orgasmic bliss.
When some aspect of penetration sex is painful, don't do it.
You're using sex to torture yourself. Become a celibate priestess for a week or two.
You have to masturbate daily and move through pain, discomfort, and numbness before you get to pleasure.