Most of all, I hope you're doing something to protect yourself and your partner every time. In either case, that doesn't tell us, all by itself, anything about you, your value as a person, the state of your virginity or your sexual experience. To understand why people think the way they do about this, it's helpful to consider history. Ideally, it's also an experience that everyone involved enjoys and feels good about, and where no one is coming to it with the kinds of ideas many have through history. This is the reason people tend to most commonly think is why vaginal bleeding with intercourse happens: If you do or did have bleeding, you'll also want to chill with intercourse for a few days so that whatever that injury was has a chance to heal. Because this tissue wears away over time, the younger a woman or girl is when she has intercourse the more likely it is that there's more of the corona to wear away, and the more likely it is there will be some bleeding.
It should be something that you only choose to do when a given relationship feels ready for it, including you and a partner having engaged in other kinds of sex or masturbation together before so that you both have a good idea of when you are and are not aroused, what gets you there, and have developed some skills and comfort openly and honestly communicating about sex together, which certainly includes speaking up if something hurts or doesn't feel good, not just quietly suffering in silence or pretending sex feels good when it doesn't.
Will I Bleed the First Time?
No need to be shy! So, plenty of women through history wound up not bleeding at all, absolutely including women who truly had not had any kind of sexual partnership before that time. The idea that women needed to prove a male partner or spouse got what they paid for through most of history, marriage involved financial exchanges and benefits when they married a virgin was the norm for most of history in many cultures, most certainly including Western culture. The "tokens" they're talking about are something like a sheet or wedding garment with a bloodstain, to "prove" she was, indeed, a virgin. Because of all of those kinds of ideas and cultural precedents, bleeding was usually seen as something that better well happen, and because sometimes "proof" needed to be shown that a woman was, in fact, a virgin as she said she was. So, I'm going to dig in here.