So. I am a 15 year old boy who goes to an all boys boarding school. I have previously tried on girls clothes and kinda liked it, both sexually and in a more general sense. Sometimes the idea of doing this bears no attraction to me, other times I really feel an urge to do this. Sometimes i feel like I want to be a girl, other times i feel kinda happy as I am. I don't really get much of an opportunity to find out how much I like cross dressing, but i feel like coming out to my parents as maybe transvestite, maybe transgender, maybe cisgender would be a good idea, so that I could get a good idea of what I like. They are both understanding and there would be no problem with coming out, I just don't know if I actually am transvestite, and whether coming out and then turning out to be just plain cisgender would turn out for the worse. I don't know whether I should come out to my parents, and I don't know what my gender identity is, although i am reasonably confident I am either transvestite or transgender. Any advice? Thanks in advance.
Well first off, I would still recommend trying stuff out, and waiting until you have a more concrete feeling over what you like. I also recommend going toa gender therapist to try an examine this; as far as I can tell, you may be gender-fluid, as you seem to switch between wanting to be a boy and a girl, but the best thing I can recommend is to avoid labels for a bit.
It seems like going to a gender therapist would be quite hard without first telling parents about the way I feel, so would it be good idea to tell my parents about all this? Also I feel like it would help me get a better feeling of what I like if I were to be able to try on clothes, and that would be easier if I could be open with my parents about it.
That's true, it would be difficult to hide what you're doing without a friend to take you there; if you really know you're parents will be okay with it, than it would definitely be a good idea to tell them. Just be careful, as parents can have unexpected reactions sometimes. Once they know, and feel accepting, you may still wish to wear clothes out of the public's eye at first; you probably know why, but it also helps if your parents could buy clothes for you considering how people would react if they saw a guy buying girl's clothes. It sounds like you know where you're going though, so I wish you luck on finding out who you are, and never let anyone tell try to steer you away from who you know you are.
I agree with MrRedFox, she has some very good advise. If your parents are cool you should come out to them so they can support and help you. I feel gender identity can be fluid for some people. I'm a lot like that myself and try not to put labels on myself. I do know I am a male, I like being a male and I am attracted to other males, so yeah I'm gay. However, I also have a feminine side that I enjoy and for the past few years similar to you I enjoy wearing girls cloths. When I wear girls cloths I feel like a girl and enjoy the feeling and being in touch with my feminine side a lot. However, I can also boy it up pretty good too and enjoy looking and feeling like a boy equally the same. It depends on my mood and it changes from time to time. I've bought more girls cloths over the past few years and found a style that I like and feels good for me. I do go out publicly dressed as a girl or sometimes just androgynous. I'm also lucky I have BF who supports that side of me. My suggestion is to not worry about what label you put on yourself, and perhaps a gender therapist would help if your considering living as a girl full time. Otherwise, just enjoy being in touch with both your masculine and feminine side of your identity. And yeah girls cloths, especially dresses and skirts are so comfortable, it's too bad guys can't wear them cause I think they would love how comfortable they are and not want to wear pants again.
