Yeah i don't know what to say....you're kinda in a pickle of your own making and clearly got some conflicting emotions going on...which are clouding your judgement because you've already engaged in some carnal interaction with this woman.
I'll offer the below thoughts, not in judgement, just my own opinion and hope you're able to have the discernment to do the best with what you've got.
Raped 4 x by 4 different dudes...
Lord have mercy.
That's a lot of drama and baggage. I mean, I would want to wonder how she was in the situation where that happened not 1x or even 2x... but 4 x.
This sounds like a very broken situation.
I certainly have had succumbed to a lot of temptation in my life, especially after I got divorced and was a single guy exiting the military.... so I dont cast judgement on your situation, merely hope that you'll recognize if you keep engaging in this sort of transactions in your attempt toward "courtship" youll keep attracting women who are not providing the sort of chastitity you want.
For me, once I got out of my whoring phase post divorce I had a rule with someone I would be willing to date....or court (ideally, which means no sexual contact) ... if you will.... They had to be able to count their partners on one hand. It was of course hypocritical for me to expect that of a woman given the multitude of my own sins.... but that was what I was willing to tolerate. Whatever that condition is, it needs to be something you can live with where you know you can trust the person... otherwise you'll always wonder what if. With my wife now, she had kids from her first marriage, was very recently divorced and. when I met her, and we were introduced through family and I could trust her when I did have that conversation with her later... Also by the time that conversation occured, we were both in the process of inquiring into Orthodoxy and had made that the center of the relationship... from the moment we began speaking to each other I had zero doubts about trust, her sincerity in everything, and no concerns. So there's that compared to the circumstances you're describing.
I "dated" a couple of girls, if you will, in my periods before really focusing on my faith and always found that when the women had circumstances anywhere near what you are describing it was both too much for me to handle mentally, and when I asked myself "Is this someone I would be willing to bring a life into this world with?" the answer was an overwhelmingly strong "NO WAY".... once you realize that, your mind should say "OK time to cut if off"
I am sorry this woman has these issues, but as this information was presented to you, frankly I would wonder how much of it was done to manipulate you into the "savior" complex. Excuse my cynicism.... but this sort of tactic happens A LOT with BPD women who try and manipulate you through telling you how they've overcome adversity in their life ect.... its a ploy to get you to put them on a pedestal and then disassociate them from the agency that they rightfully have in their own circumstances and decision making.
I mean raped 4x by 4 different men? That truly is terrible, and I really mean I feel sorry for that woman.... but I would not put myself in a situation where YOU are responsible for helping this person get through the pain and anguish they must know and go through because of this. I don't say any of that to belittle or blame the person for that.... but you get to choose what you will and won't entertain as a potential mate.
You've said it yourself, you need to get out of it. So do this before it gets worse. Once there is doubt in a relationship... there is NO doubt it's time to move on. Trust me, you do not want to do what I did which is marry a young beautiful crazy woman with a high round count who winds up having a secular hypergamous moment and pooping all in your cornflakes by filing for divorce. Better to try and remove yourself from that situation in a tactful/respectful/kind way.
Next time, seriously try and prevent things from getting physically intimate. It may happen that you indeed wind up falling into that temptation, but the better you do to avoid this, the clearer your mind will be in assessing the person's mental state and fitness to be a spouse.
Also, just to go one step further to make you realize where you are based off what you've said.... I would get yourself tested for STD's. Not to sound ugly, but if her history is what you describe, you likely have something and don't know it (Trichomoniasis being one you probably havent been tested for but probably have). I've seen a lot of this with the Marines I knew who had wives/girlfriends with more loose pasts.
Clearly living in sin with this woman is a contradiction to your faith and values. Stop doing this, as the wages of sin are death.... and you clearly are bothered by what youre doing, as you should be.
As far as chastity during courtship..... I cant really say. The below may be TMI, and I almost didn't type it, but I'll level with you just from my own experience with the hope this helps. I don't say this to make excuses or justify, merely show the complexity of life and the reality we live in now with sexual immorality being so prevalent in our culutre.
It's hard once one has bitten of the fruit not to take another bite.... but not impossible. When I met my now wife, I told her after the first "date" that if she wanted to continue to see me, we needed to pursue Orthodoxy and inquire. Covid happened as we were inquiring and due to life circumstances we were civilly married. Before the churches opened up and we became catechumens we had inquired at a chruch and the priest at least knew our genuine desire to become Orthodox and we had spoken a couple times about how to proceed as best we could while respacing the sanctity of the Church's process and the reality of life circumstances we were in with children from previous marriages, being engaged then civilly married ect... needless to say it was a very non-standard courtship. Obviously the church didn't bless the civil ceremony and any physcial itimacy we had pre babtism and crowning ceremony was considered fornication. Our priest worked with us to understand the constraints we were dealing with regarding the children we both had from previous marriages, and the sincerity of our pursuits to become Orthodox and with time we became catechumens once the Churches opend back up. Once catechumens, we did the best we could to be abstemious over the course of the year before baptism, and once baptized we repented of our past sins during our pre-Orthodox life having been civilly married and then intimate ect....and did remain chaste until our wedding ceremony after baptism.... My circumstances are a little bit different than the traditional Orthodox process, and maybe some on here whom were able to do the correct and right thing in the traditional way. None the less... I don't make excuses for the life choices I made, I've dealt with them through confession and ultimately brought my wife now, our 5 kinds that we've blended together into a new family unit, and the baby that is soon to be born into the Church.... so God worked that out for me and my family ultimately, and though we didn't do everything in a 100% perfect way, we got there eventually to making things right in the eyes of the Church and did so in earnest the best we could. I'm not saying the above is what anyone SHOULD Do... merely what happened to me in my case.
The above may not provide you any complete answers, but show that there is always complexity to these sorts of situations when living in a fallen world. If you are doing the best you can to avoid temptation of conjugal interaction, chances are you'll be able to judge the sincerity of the person whom you're dating and ascertain their genuine level of repentance. For this girl.... I dont know how I would ever overcome the trauma of raped 4x by 4 differend dudes. I have a cop friend who's wife was abused as a young girl. Its really a sad sad scene when she goes through her swings... and he has no control over his household because of it.
I would move on and get over the fear of being alone, as you're mentality shows me that you've gotten more concern with your insecurities than you do your strenghts as a man and your faith.
