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You at already admittedly in an emotional affair and headed right to a full blown physical affair. I hope you are ready for the consequences because eventually the odds say you will get caught.
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You seem to have some trust issues in general. You say you trust her and want her to be happy in one breath, but that you can't trust her in the next. Obviously, the fact that you were cheated on before leads to a general mistrust in relationships which can't help. Now reflect on this: if your girlfriend is willing to tell you honestly that she doesn't know how she would react in a particular situation than maybe that is something you just need to accept until she has been "battle-tested." At least she's not making empty promises and swearing to something she can't possibly understand. You were obviously sexually experienced while entering this relationship. She obviously wasn't. Imagine your only sexually experienced being a brutal rape as a child and then a long-term completely committed relationship (with one very mild flirtation), I daresay that it is hard to imagine. I also daresay that it is hard for her to promise with any assurity what will happen when things change and presumably she is in more positions to be with men. Imagine how intimidated she is by men in general or at least sexually (if I'm reading too much into the fact that she needs to mentally prepare herself to have sex with you, let me know), and how daunting it will be to be thrown headfirst into an environment of partying, flings, and fast and loose sex. Will she cheat? Only you can know in your heart, because you probably know that better than she.
Me personally, I try to avoid creating / putting myself into situations where my intentions, my motives, my character, my integrity, my honor are up for question.
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This will take some work.
It's different for everybody. Some people do it in their 20s. Others don't settle down until much later in life. Stop trying to figure you this out by looking at a calendar.
Lately I've been feeling like I'm just "netflix and chilling" at his place. This past sunday he invited me over to watch football with his friends since he just got back from vacation with his friends. It was fine but he whole time he was so into his fantasy football league.