I'm sorry to say this, but it sounds to me like the guy's not worth worrying about.
*onto the personal opinion, fueled by four years of seeing sweet young girls duped into doing things they'll regret later.*
If you have doubts, you're probably not ready to have sex, and that is ok.
You should NEVER feel pressured to have sex, period, It should be something that you want. If it is not something you feel comfortable doing, and he keeps pressuring you, he is not respecting you.
Telling you about the girls he could be having sex with is a pretty sleazy thing to do. More than likely, he's trying to make you feel lucky to be with him, and feel guilty that you are not pleasing him, which leads to a personal conquest: Your Virginity. If he's caught up on who he could be having sex with, he's not thinking of you.
As far as the crying goes, I'd say it's probably an act. He's trying to make you feel like he really really cares about you (which in his defense, he might, but he sounds like a complete ass so I kind of doubt it) in the hopes that you will get back together with him and give it up.
I think you did the right thing by breaking it off with him. Through my years at school, I've had countless lady friends in your situation who weren't smart enough to break it off, and they all ended up regretting it. Stick to your values, listen to your heart, and when the time is right, you will know it.
The bottom line of the game he is playing is as follows: He wants you to feel like you need him, like you can't do better, and you should feel fortunate and greatful to be with him. This is complete and utter bullshit. Someone who tries to make you feel this way can easily turn into a control freak, which is not a good situation to be in.
Sorry if I wrote too much or too bluntly. I absolutely despise it when people try to take advantage of others in this way, and I have seen it happen with more people I care about than I would like to think of. Good luck with everything. It sounds like you are a sweet young woman and deserve to find that "special someone."
p.s. For your own sake, if you drink, please don't go out drinking with this guy. He sounds like a date rapist waiting to happen.
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I've got the love of my life and a job that I enjoy most of the time. Life is good.
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