Yours is an unusual story. I think it's safe to say that few here dressed as a cartoonish s**t as a frat-boy Halloween adventure, then something more subdued (but still drawn from a cartoon character; go figure), then took up crossdressing as a more serious pursuit. For most of us, it started in relatively early childhood, no later than adolescence, and originated in something a lot less conscious and deliberate than a Halloween getup or two.

I'm not saying or implying that one can't stumble, as a young adult, onto whatever inner thing draws us to this behavior, just that it's unusual.

I would stop wondering whether your cohort's markedly liberalized view of gender nonconformity, the LGBTQ-is-cool trend, somehow steered you into this. There are lots of people of all ages who grew past traditional prejudices in this area without jumping in to be part of the scene, so if you're taking your CD seriously and studiously and pondering what it means, it's probably not the power of suggestion or a way to seem (or be) hip. What piques my curiosity is the relatively late onset apparently triggered by a couple of WTF costuming experiences.

In that regard, I suppose it's perfectly reasonable to suggest that your innate trigger just never got pulled earlier. Just because a lot of us go back to single-digit ages doesn't mean that such an experience is a universal template, or that a later onset means you're experiencing something different. You wrote about playing the role of being the wild-and-crazy college student with the other guys, and that makes me wonder that you might have been running a standard cultural routine of going along to get along and doing what the other persons-with-penises were doing without really being invested in it as an identity. A possible tell of that is how you describe your relationship with male clothing; it doesn't do anything for you emotionally, just the next shirt in the drawer, don't hate it but don't have a proud identification with looking handsome dressed as a boy, and so on.

That resonates with a lot of us here, as does the contrast of really getting into putting yourself together to present as a woman. I think it's wise to pay attention to the indifference to drab (I'm the same; absolutely no slob in me, but no thrill whatsoever from looking good as a guy) and the attention you pay to the other side. Understanding why you can take or leave the one but work hard at the other is key to finding your way through this. When our wives and girlfriends and others in our lives want and expect us to enjoy presenting as male, but we just don't feel it, there's something important there that we ignore or deny at our emotional peril. It can be slow-drip painful to go through life with that kind of unfulfilling sense of self.

You also need to know that there is a common experience of really coming to terms with cross-gender identifications at about age 30. Not everyone, but a statistical cluster. It seems to be when the defenses start breaking down, when thoughts of career and family and such start to loom big and unanswered questions keep tugging at your sleeve.

You're among friends here, and you'll get a lot of feedback. Don't panic or give up if a particular opinion seems judgmental or dismissive of what you're experiencing. You're asking the right questions, and only you can really answer them.