I found a deleted conversation my boyfriend had with a really pretty girl?

If everything is like you're making is sound, he was flirting with her, and that he's extremely clingy to you and paranoid of losing you because he has no idea why you'd date a schlub like him. This makes no sense to me and I don't think I'm getting the whole story, even with that wall of text, though him asking her to show him shaking her *** is not good, very bad in fact. Nothing to do with him for 5 days to the vacation is a worse plan though, if he truly doesn't understand, you're leaving him in the dark, and he'll just get confused and angry at you.