Does Liking Crossdressers Make You Gay?
This is a question I've seen asked before online, and in person, and I have even pondered it before in regards to myself. If you (presumably, your being a straight guy) are attracted to a physically male cross-dresser, does that make you gay?
This question can be taken a step further and applied to transwomen, ladyboys, and any other number of male-bodied, female-presenting individuals. (The thing with crossdressers, specifically, though, as opposed to the various kinds of transwomen, is that many cross-dressers identify as male and simply like to dress like women, whereas a transwoman by definition identifies as female. But more on that later.)
This subject can even cause anxiety in some people, making them frantically question their sexuality because they happened to find a given woman attractive, then realized somehow that she was not physically female. Some guys fear that this reflects badly on them or automatically makes them gay. (Actually, many transwomen and cross-dressers have unfortunately been beat up precisely for these kinds of reasons, but that's another story entirely.)
To me, that seems like assigning too much importance to the external world and society's views, and it's a failure to take into account what is really going on. A person's preferences come from within, so they can't be judged by some outside standard. Whether you're gay or straight has nothing to do with whether someone you like is a man or a woman. As a rule, nothing external can "make you" of any particular orientation.
Let me explain:
So does it make you gay?
There's no universal answer to this, as far as I can tell, because it largely depends on perception. Any kind of orientation ultimately depends on perception. What you think of someone is ultimately more telling that what they actually are.
The thing which first must be understood here is that gayness or straightness has nothing to do with the object of your attraction, and only has anything to do with you. It's easy to treat it as some sort of two-way interaction, as it commonly is treated, but it really is a private state of mind. Though a person you're attracted to might trigger a reaction in you, ultimately, everything you feel comes from inside you and is of you. This is something you have to take up with yourself first.
Being gay or straight is something very internally-based, something very much about what is going on in your head, more that what's going on externally. So, really, whether you're gay or not for liking a cross-dresser or a drag queen isn't really so much about whether a given person is a woman or not, it is more about whether you perceive that person as a woman or not.
So the real question is, do you see the cross-dresser you're attracted to as a woman or a man? Do you feel like she is a woman or a man when you look at her? Are you responding to her femaleness or her maleness? Does being attracted to her feel gay, or do you respond to her the same way you respond to any other sort of female?
If you look hard enough in yourself, you should hopefully be able to find answers to these questions.
What's going on with her
Now, a cross-dresser or drag queen may identify as either a woman or a man. Some so-called cross-dressers are transwomen, meaning that they are women who were born in male bodies, and such individuals would probably argue that you are not at all gay for finding them attractive because they are, after all, women. (I would tend to agree.)
However, some cross-dressers are not transwomen and are, rather, (sometimes completely straight) men who simply like to dress like women for a multitude of possible reasons. If you find such a person attractive, you are indeed technically attracted to a male, but, again, it hardly matters what is happening externally, as the only thing that counts in something so personal as ones orientation is how one perceives the object of affection. The question still is: Does he appeal to you like a man or a woman? Are you attracted to him because he is a man or because you feel he is a woman, in spite of the fact that he is not? (Still, be forewarned that such individuals are not women full-time, and lose their temporary womanhood the moment the fancy clothes come off.)
Bringing it together
When bringing all of this into consideration, it does become a little more clear-cut: If you perceive a cross-dresser as a female, and are attracted to her, this is a sign of your straightness. If you perceive a cross-dresser as male and are attracted to him as a male, you are most likely attracted to males to some degree (Though you're not necessarily gay because, after all, if you're still attracted to females, it may just be that you're bisexual to some degree).
So, ultimately, I guess the short answer is: Just liking someone doesn't make you gay or straight; it is how and why you like them that is the deciding factor in this regard.
So how do you like this person? Think about it at length, and you will know because, really, no one can tell you what your orientation is; only you know for sure.