So I recently had my girlfriend break up with me and move on very quickly to another guy. Reasons being is because she's young, immature (when she wants to be), insecure (hence her need for male attention and validation), and her habitual nature of being unfaithful.

Other very important reasons were due to me not spending enough time with her, buying the relationship (gifts, food), giving in to her demands, not asserting myself, making myself too available (driving her, cooking for her, etc.), AND most importantly... chasing her in her last relationship to the point where she cheated on him with me. My greed, selfishness, and entitlement got the best of me. I paid for it in the end.

The thing is I very much like strong willed women like she was but are often very spiteful and unforgiving when crossed. The way I handled things at the end wasn't the most tasteful but still mild in comparison to what I could have done. I realized that had I other women around me it might have kept her in place. She on the other hand can have any guy she wants. Not just because of her looks (she's an but because the ratio of men to women at the school is ridiculous in terms of the male population. She's given a lot of attention unless people know she's in a relationship, which pisses her off but when she's not taken her sexual appetite will seek out guys that she can kill time with. Basically she chases infatuation until something new comes along.

My question here is how can I better handle these girls to make sure they stay faithful and with me. Yes, it does depend on them but it does take male assertion to make sure they understand boundaries, uncompromiseable principles, consequences, and so on. Please advise.

I think there is an old Chinese Proverb..."Can't turn a ho into a housewife"

What you're wanting to do is change who she is and it's beyond your control. You can let her know what you want, but it's up to her to make the decision to be faithful.

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At the moment I read "school", I made this little facepalm gesture.

I, personally, cannot understand why the hell a schoolboy would want an LTR. Do you know why?
Because you are fucking kids. You don't have a relationship, you just play pretend. Neither you not her have the mental resources for a relationship. Schoolboys and girls are still larvae of human beings, they have no distinct personality yet, they still follow trends to look "cool", and they cannot possibly be completely responsible for their actions. So, as a rule of thumb: if mama and dada still pay for your life, "relationship" is a forbidden word. Leave the grown-ups to deal with it. Yes, I'm blunt, kill me.

Now, with that said:
First of all, don't attach yourself too much. As I mentioned earlier, you have a lot of growing up to do, and there is a solid chance your hook-up will disintegrate sooner than you think.
Second, don't beat yourself (or her) too much if cheating occurs. You are not truly committed.
Third: In school, it's all about being cool and being desirable by the others. So, if you don't want to be "cheated" on, you just elevate your social status to the point where whoever she fucks next would be a downgrade. There are many ways to do that; my brother, for example, has a rock group and plays both guitar and keyboard. Or become a dancer, or get a fancy car, or whatever shallow little thing you decide to come up with.
Fourth: Contrary to PUA belief, you can make romantic gestures, as long as they are "cool", and they are PUBLIC. If you get a red rose and toss it in the air for her to grab if front of her mates, that's cool. Don't do it when tote-a-tette.
Fifth. Don't invest in her financially. It's not your money, even if you earned it on your own - its your parents', until you leave their house.
Sixth. State clear what will make you go. Keep it short and sweet. Cheating should be one; gossip behind your back - too. Don't make it unreasonable for your age - the more demands you put on, the more likely she is to rebel.
Seventh. If she decides to be vindictive, don't be afraid to go to a war. It gets ugly, if I remember correctly from my schooldays, but makes a great show. If, however, she keeps it civil, you are obliged to do so too.
Eighth: BE AWARE THAT THIS SHIT IS TEMPORARY.

Girls this age chase infatuation, not relationships. So give her that. And you take my honest advice - don't play with relationships, just hook up, until you decide you're ready for a family. No need to waste your heart on chicks.

You cannot make an unstable girl, stable. You cannot change people. If you meet a girl who likes to sleep around, she will not stop sleeping around for you. And in any case, snatching another guy's girlfriend wasn't exactly an indication of your own maturity, either. Maybe you are just attracting girls who are like yourself.