Even starting off this little post has me a little scared and bamboozled.

In my normal day to day, I'm always super confident in almost everything I do. Often times overconfident or a bit brash. It has been this way for a few years when I kind of came out of my shell after years or rarely even speaking except with those I was extremely close with. But with my whole transitioning plans, I basically hit a brick wall any time I want to do something and I become the quiet, teachers didn't even know my name, kid that I was. Went out with the best friend tonight for a few quiet drinks and a catch up. Wish I could have gone out in a dress and heels or that kind of attire. Although having to shave my legs with how cold it is, no thanks. But the best I could do was girly, kind of androgynous clothing. So basically presenting as a gay male, with only me knowing my clothes from the women's sections. I still haven't taken any steps towards actually wearing proper ladylike clothing. Even in my own room. Dresses, skirts and the like. Partly out of fear and confusion with regards sizes and fits and all that. And I just wish I could get over it. I went out tonight in fluffy Leopard Print High Tops with glitter in my hair. Would probably get less attention in a dress compared to some of my current outfit choices.

Same thing with makeup. First time I went into get some. Clueless kind of and was going to ask the lady. Walked in pretty confident. Got scared, and ran and hid in the men's clothing part of the store basically. Until sheepishly returning to the cosmetics sections and feeling like a fool. Have a friend working in a makeup place now so that helps picking up supplies and things. But even though I got some stuff almost two weeks ago off her, it's still up in my drawer in my room, untouched. Again fear. Just been sticking to BB cream now and then when I'm heading out with good friends who know.

Similar story with the hair. Longest it gets is medium guys. Keep getting it cut. Even though I want it to grow out. And often I'm scared to go shopping in the women's section unless I have a female pal there with me. And I keep putting off organising my voice therapist and trying to make an appointment. Although awfully sick and coughing the last few weeks and waiting for that to clear.

Had similar fears when I was starting my laser. Although I kind of like going in now and get with the girls in there really well. One I had started it was simple really. A lot of the time I kind of feel like I'm going to fail or something so I just avoid it so I technically don't fail?
Even though I should be jumping into these things head on. I'm basically having to wait for formalities to be done. Appointment set for Feb 4th to get second opinion and then allowed go to the Endo. Second opinion is almost a dead cert. And actually doing the above would probably make it even easier. So I'm basically waiting around and doing nothing. And I'm driving myself mad but still not mooching. I just feel very lost in the female world. I know I should belong and revel in it. I can never seem to find a foothold really. Or often if I try, I only seem to fall backwards. I hate the scared, lost little kid feeling. Like I know what I need to do. But I can never actually bring myself to do it. Even though I know once I take the first real steps properly, it will snowball and I'll get it no problems.

It is more than just something new.  In each instance you described it is a leap of faith into the unknown, and even unknowable.  You are stepping  into gender discovery.  In my case that took decades, and it nearly took my life.  I can think of nothing more terrifying than acknowledging that your life to this point has been ruled by a carefully constructed persona that you are now discarding in favor of what?  Authenticity?

From the concrete to the abstract in one step, knowing that there is no lifeboat.  Once in, you're in.  It takes a special kind of courage, and a whole lot of faith.  Give yourself a pat on the back and remember this the next time uncertainty hits, or when fear pushes you into the barber shop.

Fair winds and calm seas,
Julie

The first steps of anything life altering can always be terrifying, no matter how large or small. The fear of failing can certainly be a powerful deterrent to beginning anything, however to borrow a cliché, you miss 100% of the shots you don't take. You've shown great courage and have adapted to many things so far (like Laser), some other parts may take practice and time to get used to, nut it is this time you can use to figure out things you do and don't like.

As for the hair, I know there is a temptation to keep trimming it in the medium guys stage, but as someone who has gone from short to shoulders numerous times I would suggest either letting it go or hitting a style you are comfortable growing.

It is quite silly huh? You put a barrier for yourself as what you see as 'taking it too far'. When you do, you trim your hair, take off the make-up or wear 'proper' clothes. Maybe you can think about changing your rules from within? It can be discouraging to look at men as an example if you want to be a woman, but don't take it wrong. You can look at men with long hair, feminine clothes and often models also wear make-up. They are still men. It really is only the small things that makes people see you as a woman and you yourself have to realize that before you can grow out your hair and try out more things.

I hope I am making any sense at all o.o.

And take things slowly. Do not from one day to another wear heavy make-up or a very feminine top with sparkles in your hair. It isn't weird if you are unsure about your actions that you get insecure when you take it too fast. Take it slowly with steps so small that you expand your limits without even noticing yourself ^^.

Thanks to all of you 

Julie, that was actually so wonderful. And the lifeboat analogy seems se right too. You mentioned a constructed persona, but I'd say I actually have a few of them within different social and professional circles I guess. Only able to relax and be fully me with a few individual friends currently. And with my current sports team, most of them don't even know I kiss dudes. The other circles I am pretty much just an effeminate gay. It's something but not the full freedom and expression that I need.

Erin, I guess it's partly the failing thing but also afraid of looking silly or stupid at the same time. I'd love to grow my hair out or change the colours and things, but I never really have. Could never find something that didn't look silly while I'm still in boy mode. Still rocking the undercut style. Bit heavy on top and I can play around with it and stuff but again it's like a half in half out thing I'm doing.

Kirey, exactly it's the taking it too far thing. I know where I want to go with it yet I'm still scared and stalling. Although with regards to regular clothes as you said, I still generally wear quite effeminate clothing for guys. And my piercings and tattoos that often I use almost like accessories to my outfits are quite effeminate too. When I use makeup it is still very minimal. Nobody really knows I have any on and just thinks my skin is perfect really unless I tell them. I almost always go with sparkles in my hair if I'm heading out. Or wearing a tiara tbh
But again I think my problem is half measures. I want to wear female clothing. Not just effeminate clothing. It does help that most people besides my close friends still just think I'm like a super gay fairy and are used to girly tics and clothes. But I'm still scared to like go all the way with heels or a skirt as I've mentioned.
I do have a sparkly short sleeved kinda of effeminate hoodie sweatshirt that I love. Pair that with glitter hair and one of my pairs of glitter shoes and I'm looking well I'm like a m->-bleeped-<-ie with shiny things. And I adore my glitter.

What would these small things you mentioned include? Maybe I could at least start toppling some of them?