I've come to a point now where I'm beginning to have serious concerns about my identity. I am a teenage male. I suppose I'd like to hear from those who have "come out" as being transsexual to understand if I am overreacting, simply confused about being confused, or truly am transsexual.
My earliest memories of any kind of "abnormal" behavior come from a pretty young age. I can remember frequently trying on my mother's high heeled shoes and walking around in them. I can remember asking my mom/looking forward to putting on her clip on earrings; in fact, I remember one specific time when family was around and she went to show them some of her jewelry and I begged her to let me put on her earrings. More vaguely, I recall her picking me up from kindergarten (or maybe first grade) and me asking if I could wear her earrings when we got home. I also vaguely remember instances of her letting me put them on, and saying something like "don't tell your brother or your father", but it's all is pretty vague in my memory. In one other specific instance, I was playing with my older brother when I put a circular key ring on my toe pretending it was a toe ring because it made me feel like a woman. I then began to act like a woman.
As I got older I discovered masturbation. Eventually I began putting on bras as I masturbated; years later I still conduct the same practices. Sometimes I put on a bra and a dress and jewelry and walk around my house and just sit in the female clothes. More often than not it ends with me masturbating. Many times I look forward to dressing like this; I look forward to leaving school and having the house to myself for a time so I can dress in the clothes. However, after I masturbate I no longer desire to wear the bras and dresses. At that point I simply change back into my regular clothes. There have been a few nights where a sleep with an undershirt stuffed with socks as though I have breasts, and I can even recall doing so once or twice at a pretty young age... On the few nights I have stayed home alone overnight, I would plan on sleeping in a bra; however by that time I would masturbate and never end up sleeping with one on.
Because the strength of my urges dies down after masturbating, I wonder if it's all just some fetish... I also feel like I could be somewhere "in between"; I don't necessarily feel "wrong" in my body, but sometimes I desire to be a woman, and sometimes when I dress as one it feels "right". There have only been a handful of times that I can remember when I have had any kind of real "I need to be a woman." moments... Most of the time I feel okay with myself, and other times I simply wish I could be a woman, or fantasize about being one.
My prom was just a little while ago, and while talking to a female friend of mine she for some forgotten reason asked me if I would wear a dress to prom for her. (Like I said, I can't remember why it was asked now/why it would benefit her..

) Naturally the question was just theoretical, but it felt good/exciting when I answered "Yes, I would.". And when I saw her at prom, I sort of wished I could be a girl and be wearing her dress, and be as pretty as she is. But at the same time I felt okay and like, not-out-of-place in my tuxedo... So yeah... And as a note, this girl and I go back a long ways, and date on and off, and at one point this year I became so stressed about my identity and questions that I almost told her that I am in fact transsexual.
I may be leaving some stuff out, but I feel this is enough to generally describe my current state. I apologize if it's long winded :/ but any input would be greatly appreciated. Thank you

(oh one last thing: I'm not really too "manly" of a man by nature.. You might say I'm a little feminine compared to other boys my age)
thanks again