I hope it's okay to reblog with some of my personal thoughts! (I am Catholic as well as Presbyterian if you want to know my background, anon. I am also currently extremly happily married and polyamorous i.e. have a second partner. Also my now-wife and I had sex long before we were married!)
As someone who does not abide rigidly by every point in the Catholic Catechism (given that I'm trans and queer / "same-sex" married and all that), I definitely believe that how we understand chastity can be reframed.
The Catholic defintion of chastity at its most basic involves moderation in sexual "appetites." In the most stringent application of the Catechism, this involves only having sex within marriage with the aim of procreation.
Obviously, a lot of Catholic married couples use birth control / have sex just for the fun and intimacy of it! Given that reality, along with the reality of a lot of extramarital sex and queer sex, etc., this might be a place you decide you are willing to reframe to something more expansive than the Catechism strictly instructs.
Does chastity have to mean total sexual abstinence? Or can it mean being thoughtful and intentional about how you have sex?
Because it combines Catholicism with a potentially more expansive understanding of sexual ethics, I believe you might get a lot out of Sister Margaret Farley's 2008 book Just Love: A Framework for Christian Sexual Ethics.
Farley’s framework is centered around seven points that help determine whether sex is “just” (i.e., it gives to each person their due, and everyone’s autonomy and relationality is respected):
To briefly clarify a few of these:
Mutuality refers to “mutuality of participation” – there should not be this idea of one “active” and one “passive” partner; both should be engaged.
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Equality refers to avoiding to great an imbalance in power dynamic – a teacher and student is one such example of imbalanced power.
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Fruitfulness does not refer solely to procreation, but a production of interpersonal love. Love should overflow into the world! The experiences you gain through sexual activity can generate increased understanding, energy, etc. you can share more broadly.
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Social justice is about sex on a wider sphere – fighting against domestic violence, etc.
Various kinds of sexual relationships may well fit into Farley’s sexual ethic: sex before/outside of marriage, sex among LGBTQIA+ persons, polyamorous sex…examples of all these kinds of relationships can be found in which all of her seven points are met.
For more, read Farley's whole book or check out my #Margaret Farley tag.
I also want to name that the concepts of chastity and virginity are often used as a means of control over vulnerable people.
For example, virginity is expounded as a virtue for girls and women far more often than for boys and men!
In my Presbyterian denomination, we had an old clause called the "chastity and fidelity clause" that required ordained ministers to be "faithful in marriage and chaste [read: sexually abstinent] in singleness [read: outside marriage]."
But "shockingly," that clause was only ever enforced against women and queer people! (And because this was before same-sex marriage was legal across the USA, it meant that queer people could never have sex, even with a life partner.) It was an open secret that plenty of cishet ministers / seminary students looking to get ordained were having extramarital sex, but they were never the ones kicked out of the system for it.
Sexuality as a whole is a very effective weapon of control. If you can convince people that most sexual activity (even masturbation) is a grave sin; while being aware that most people at least occasionally "fail" to live up to those sexual standards; then congrats — you have a population steeped in deep and often secret shame and self-loathing.
And a person full of shame is much easier to control; to some extent they may even believe they "deserve" any harm done to them.
...Okay sorry anon, that meandered on past what you were actually asking, but it's one other layer that may or may not help you as you unpack things around virginity and chastity! Figuring out where the concept of chastity is actually holy, versus where it is a product of human powers attempting control over others, may be part of the process.