Thank you for your question. In your situation, and according to your age, it’s hard to say for sure if you are transgender/transsexual or if you are a cross-dresser. Both are definite possibilities!
There are males who simply prefer women’s clothing and enjoy wearing makeup. Some only do it in public, some only in private, and some, both. In any of these 3 cases, it doesn’t necessarily mean that you are
transgendered. A transgendered person usually feels as though they were born into the wrong body. Often they feel uncomfortable in their biological body.
Cross-dressing, for them, usually does not “fix” their gender issue, as underneath their clothes, they still feel somewhat ‘wrong’. Some opt for surgery and hormone treatment, but this is not the solution for everyone.
If you feel most comfortable being around female friends, it doesn’t mean you are ONE of them. Yes, you identify with them more than you do with men, but what you need to figure out is if this is on a biological
level, or more of a socio-psychological level. If it is natural for you to feel connected to females, there are many reasons why this may be. For example, if you have grown up around a lot of women (such as your mother, sisters, cousins, teachers), or lacked a strong male influence in your life, you might feel less comfortable around men, simply because you know less about them.
Also, there IS such a thing as a feminine man! You might feel more in your element being around females and sharing in feminine-oriented activities, but it is still acceptable for you to feel and identify yourself as a man. You might feel that, to be the best person you can be, you want to and need to cross-dress, but you can certainly retain your identity as a male as well.
However, if you find yourself feeling more in tune with girls through your body self-image, then there might be a possibility you are transsexual/transgender. When cross-dressing, did you ever stuff your bra or add ‘parts’ to make you appear more feminine? Do you look at your female friends and think ‘Why don’t I have breasts too?’…or do you feel uneasy with your own biological body?
In either case, seeking council is advisable, as it might ease your mind and help you sort through your feelings. Hopefully I have somewhat clarified the situation for you, but I would recommend seeking professional help as well.
With time, you may figure things out without outside assistance, but an extra ear may give you insight you may not find on your own. Good luck and feel free to contact us again if you have more questions!
Dee, for AlterHeroes