Really good idea, but implementation... Looking at MC constantly whining, self-reproaching and self-doubting, a quote from "The Office" came to my mind. Todd Packer to Michael: "Hike up your skirt, pull out your tampon and borrow some balls". Seriously Cap, we already have Kelly for the infinite wailing.
Look Cap, I've came up with an amazing idea for another one ending, quite a dramatic one! All girls break up with Jack saying something like "Oh my poor thing. A man with only a huge dick this is not enough for real woman, go get some brain and balls first... Bla-bla-blah... Good luck and so long.". Girls go to a date with twins. Dusk has fallen, Jack sits on the bed, cries and jerks off all alone.
It's a gift. You may not mention me in credits ;-)
I wouldn't say that dislike your game in general. I bought it and high rated it.
This is only my opinion, I think MC shouldn't be that alpha or badass, you're right, it would be a kind of cliche. In routes that include LOVE relations with Cassie, pretty strong and confident girl, MC should be more confident with her. I don't believe in Cassie's love completely now, but if I'm wrong and she really fell to him, this connection shouldn't last long.
Please Cap, give MC just a bit more masculinity in upcoming game days.