Confused

I don't blame you for being a little freaked out. It can be some scary business at first.
There's nothing wrong with being transgender--I know some MTF people who do it quite well, and love their lives. Or, maybe you aren't trans--you might be genderqueer, depending on how strong that inclination towards being a woman is. My honest advice is to start small. Maybe wear slightly more effeminate clothing, shave your face and legs/arms, maybe let your hair grow out a little. Things that can be reversed easily. See how you feel while wearing them. Then, if you decide you want to transition, you can go on to the next step, and the next, and the next. Start small, live happily.

 

Rin's nailed it. Don't rush into anything, just experiment and see what happens!

 

For cute effeminate clothing that you would feel comfortable in if you're self-conscious, try fitted dress shirts and tighter jeans, maybe with flare legs. There are lots of cute women's clothes that you can feel comfortable in--just take $20 or so and go to Goodwill. Pick out things that make you feel confident and comfortable. You'll look beautiful in anything you choose to wear.
((I love otaku culture too, wow. Just finished watching SNK))

 

I started with underwear. Then a skirt in my bedroom when nobody was home!

 

For me trying all kinds of female clothing that caught my eye in the privacy of my bedroom was the first step to processing what my gender identity was.

I would look around stores online and order in things, then keep them in a locked filing cabinet and whenever i wanted I'd put the doorstop under my door so it was "locked" and I would try those items on and see how I felt about it all. Trying it all out in the safety of your own room in my opinion is a great first step.

Combined with shaving everything and having long hair, how feminine I looked the first time I saw myself in a dress blew my mind, was amazing to me how good i Iooked. Was a huge help towards figuring it all out.

From there I decided to take the next step and I ordered some female neutral looking t-shirts that show off my shape and started wearing them normally, it was a huge confidence booster for me, very liberating.

I feel a slow gradual shift is the best way to deal with it all, as it gives your mind time to process It all and figure it all out, and if you decide to eventually go for a major change and come out, the slow process of subtle changes has a way of giving you the confidence to be proud of who you are and it also gently hints to those around you that something may be up, so when the time comes to tell them their subconscious offers all these tiny signs they didn't really pay much attention to, opening their minds up to the idea of it all.

Also a bit too far ahead for you currently, but I find when explaining things to people, it helps you if you avoid using labels to explain. As usually what happens when someone associates a label or movement to you, they immediately assume they know everything there is to know about you and don't listen to you any further. That really isn't how to have a conversation, id much rather explore each others ideas in real time. So for me, when it comes to explaining who I am to those I'm not fully open and close to, I intend to avoid loaded words and labels to decrease the chances of them making assumptions that don't apply to me.

Also, I find that times of stress and suffering have a way of wearing down our guards against problems were avoiding, so it ends up that these periods are actually the best time to start learning about ourselves and sorting out our problems, so with that in mind, I advise that you listen to your thoughts and feelings, and begin exploring what you find.

 

DON'T EVER SAY THAT! NEVER EVER EVER EVER EVER!

If that's how you want it, you make it work! I want more than anything for someone to look me in the eyes and tell me honestly that I look really cute today! I'm 6'4 and built like a small whale! It's hard work but you can make it work, even if it seems like it might go wrong! (Sorry, I worry when people say things like 'it won't look right' and I panic that it might not happen for me!) :3

Also tomboyish styles are comfy and really great. However if you want to mix it up a bit, try adding a shorter skirt and leggings instead of trousers to your tomboy look!

EDIT: BTW, I assume your username means that you are thinking of using the name Katie if you ever need to...how do you feel when somebody calls you Katie (which is a really cute name btw!)

 

Then I'm going to call you Katie now, K?

Self concious can be OK because it shows you things you need to work on. If I sat here and said 'Well I didn't shave this morning but I can probably wing it!' I'm not going to get out the front door before someone realises I'm not a 'real girl' (GRRRR).

The first time I went out, the illusion was completely blown by the fact that my socks and shoes didn't go with the rest of my outfit at all, afterwards I felt like a complete idiot and I hated it! But because I was self concious I got myself some shoes that DO work and now my clothes look OK...I mean I'm still not as cute as I want to be but I'll get there.

Point is Katie, use your self conciousness to your advantage but don't let it stop you! If you want to dress like a goth-loli maid then you go right ahead and do it! (Also post pic 'cause I want to see it :3 )

 

Tell me about it!

I have always hated clothes shopping, mainly because mens clothes are basically crap. In the last 10 years, i think I've owned about 10 pairs of identical trousers and shorts, and worn them with an alternate t-shirt and shirt combo every day.

Now I LOVE shopping, because there are so many cute things I could wear, and I can actually see things I might look good in...it's a disaster!


Embarrassing, eh? I'm intrigued, why is it embarrassing?

 

Ah, that's exactly how I felt when people started calling me Holly!

I don't take too long if I went in for something specific...there's only so long you can spend looking at socks y'know? But sometimes if I'm browsing I'm a disaster! Every time I turn around 'oooh that's cute' "woah I'd look good in that" 'Why don't I already own these!?' I'm so poor now!

 

You lucky thing! *jealous*

 

At least you can enjoy it for a little while...I have to try and force myself to stop eating nice things so I can get thinner! It suuuuuuucks! Stupid brain. I never wanted a boyfriend before (or a partner in general) and now all I can think about is how I want someone to tell me I'm cute and snuggle me on the bed!