I am just starting to take my first, faltering steps on this journey and, after a lifetime of knowing that I was in the wrong body, am preparing to take the decision about whether to finally do something about it (I am in my 40s) or let sleeping dogs lie.

So, as part of helping me make that decision, I have decided that it is time I tried setting foot outside the door in role.  As I have just discovered that a friend of mine is contemplating the journey, we have decided to both go out in role for our next meeting with our group of mutual friends in two weeks' time.

Now, I am terrified!  I have always dressed in a masculine way and, whilst I no longer wear the shirts and ties as I used to in my teens, I still wear combats and DMs and have short hair.  However, even in that get up, I am unequivocally womanly.  I am petite, have relatively soft features (although becoming progressively less so as I descend into being a hoary old hag) and...well...just look like a woman, and not even a butch one, in spite of my short hair and masculine clothes.

So, how should I approach this?  I am happy to wear my most butch clothes and a binder (just ordered), but I am not sure about going any further than this as there is no way I would make a convincing man.  However, what would be the point of doing this if I am not going to attempt to experience what it might be like going out as a man?  *sigh*

Any suggestion on this would be most gratefully received.

Thanks!

Heres, my two cents. Life is short and precious. Live the way you want to. If you feel like you want to come out already then do so. The age and environment don't matter, if they can't accept that then forget about them. Play it cool and be who you are. I always make it seem so easy but it can be easy if you go easy on yourself 

You are just now starting your journey on a very long road.
You will not be able to present male very well at first, that is ok. Everything takes time and effort to perfect.
Think of it this way, you are like a prepubesent boy. You have alot to learn and adjust to concerning male culture. You socialized female for 40+ years, you have very few if any time in the flight seat as a male. That means you have alot to learn, and that is ok. Everyone starts somewhere.
Hit the books, talk with transmen, and be ok with making early mistakles. Watch natal men talk with late in life MTF. They (we) have alot of combined knowledge of what it is to be male. Many of us did a rather spectacular job of playing the male part.
Good luck and best of wishes
Cynthia Lee

accord03, thanks for your response, but I am not concerned about how my friends will respond, if this is what you meant.  They are absolutely fine with it (lucky me).  However, I guess I am a little self-conscious to be walking out as an obvious woman who is clearly trying to look like a man and failing, miserably.  I think I will have to resign myself that this will be the case for the foreseeable future and resolve to make it not a problem.

Thanks cynthialee for your kind words.  Yes, it feels as though it is likely to be a long, uphill haul.  But I have at least now started the journey (wherever it will lead).

I do have a lot of socialising to undo.  I have only recently come to realise to what extent I have moderated my actions, speech, topics of conversation to be acceptably female.  When I realised this and attempted to drop some of the effort, what a relief!  However, I think it is ironic that I have spent all my life trying hard to act more like a woman and am now trying hard to act more like a man!  Does it ever end, I wonder?

Anyway, has anyone been in the same position as I am, looking unavoidably female, wanting to walk out as male, but not wanting to look frankly ridiculous?  If so, how did you handle it?

Well, it's gonna take awhile to come out looking as a male after 40 years of trying to be something you're not. For now just try and gets tip to look more masculine and it doesn't matter. Go out the way you want it and you'll improve eventually.

If all you do is think about how female you look and convince yourself that no one will ever think you are male, you will never pass. Looking/being "manly" is all about being ridiculously confident.

I am 5'2" skinny and would have had quite a nice female body if I had decided to flaunt it. Everyone used to tell me how gorgeous I would be if I tried to look feminine. Now, the people at my parent's doctors office don't recognize me. They tell my mom that they didn't know she had a son. I use the male bathroom and no one questions it. I get sir at restaurants when I go out with my girlfriend. Now I am about 5 months on T but most of this happened Pre-T.

Exactly what Carson said. 

That's great for you, Carson.  I am really happy that you pass so easily.  For me?  I just don't think it will be so easy.

Yes, I agree, confidence is important.  But it is not sufficient.  I would be more likely to look like a confident lesbian than a confident man.

So, do you think I am going down the right path by thinking about not going the whole hog for my first outing?  Not trying to look like a man, but just being comfortably masculine?  Or should I go all out?  Hm.

I am also facing the problem of not yet knowing what male clothes I would want to wear.  I don't want to be anything other than a physically male version of me.  I am quite happy with that.  But, it will take me a lot of time and effort to figure out what I would need to change to achieve that.  Where do people look for inspiration?  I am not a conventional woman (I am an aging industrial goth, I guess) and do not want to be a conventional man, so mainstream fashion mags probably wont help.  Any other ideas?

Also, would it help to have a quick photo of me?  I will take it down pretty quickly as I am not keen on having my physog on an open forum, but it might give you some idea of what I am battling against.

Do whatever you are comfortable with, dress how you want. You shouldn't transition for the sole purpose of achieving complete passable masculinity, yes it helps, its great but the whole point is to be comfortable with yourself.

As for clothes, go to the places you normally get your clothes but instead of buying female clothes, buy male clothes.

Yeah, show us your pic so we got an idea. I was gonna ask you before but didn't know if you wanted to.

ETA: Picture put up and mercilessly taken down again.  Sorry!

WOAH! LOOK at your boots. They must give you alot of height  Firstly, I would like to say is lose the pink/red hair and make up. Go to the same shop you buy your clothes but buy it from the male section and see how different it gets. From what I see in your pic, you jsut need a few adjustments for now Not to worry.

Papillon, I was full on feminine woman before transitioning, and now people who knew me well before (acquaintances) do NOT recognize me and I am seen as male 100%.  Such is the power of testosterone.

OTOH if you're not planning on taking T, then all you can do is be true to yourself.

FWIW I'm also in my 40s.


Jay

LOL!  No, that isn't me trying to pass.  That is me pre any sort of attempt at masculinising myself.  In fact, with many attempts to feminise (see Tinky Winky handbag there?  Lots of makeup?  Yup).

And the boots are man's boots, would you believe, and I tower over everyone with them.

Yes, I am sort of resigned to the fact that I wil have to lose my beloved red hair.  But it is just too girly.  I haven't seen my natural hair colours for many, many years but now might be the time.  BIG step.  *sigh*  Ah well.  It guess it doesn't mean that I have to wear jeans, trainers and a Black Sabbath t-shirt as well...

Jay, thanks so much for that.  I had never thought of myself as feminine (having spent ALL my life being criticised for being butch), but now...  But I do like to dress up and don't see that stopping any time soon.  It is therefore a pretty good job that I identify as a nelly ->-bleeped-<-.

I am planning on taking T, so I am hoping that will help me on my way.  It is just coping with life in the meantime.

It is very difficult in the beginning but once you know you're about to start T, things tend to look up and life isn't that hard. I hope to start T in a few months time
WOO WOO. Been waiting for this moment

QuoteAnyway, has anyone been in the same position as I am, looking unavoidably female, wanting to walk out as male, but not wanting to look frankly ridiculous?  If so, how did you handle it?

I look like a man, I know that I do. It does make me feel like ->-bleeped-<- but I absolutely refuse to let anyone in the cis world see it. I walk like I am proud to be me (which I am), and I never show fear.
Also keeping my sytle in the decidedly female but bordering androgonous.
You have to just say 'damn the torpedos.....!'

FWIW I'm also gay.     So prior to transition, while I was fairly tomboyish, I also presented feminine (long hair, etc).

When I first started transition I looked more like a butch lesbian and had lesbians tripping over themselves to get to me.  It was comical, except that I wasn't ever really female, and definitely never a lesbian!  That was the hardest part for me, going through that period where the world thought I was a lesbian.  Not that I dislike lesbians or anything (I work with quite a few and have many friends who are),  just that I was NOT one.

Jay

P.S.  I don't see why you have to give up your red hair.  True, it won't help you pass in the beginning of transition, but I've seen lots of guys (gay or not!) with brightly colored hair.  Once T kicks in, the color of your hair won't matter.

P.P. S.  Cynthia, you do NOT look like a man!

Yup, yup cynthialee, this is the conclusion that I am starting to arrive at.  I can not hope to become a completely convincing man, but at least I can aim at a totally me me.  Having spent my entire life being considered "freaky" and "not quite right" it would have been nice to be totally accepted in my identified role, but I guess we can't have it all, can we?

Jay, yes, I am fully preparing myself to be taken as lesbian.  And, as I live is the gay capital of the South of England, I guess it wont be a problem in terms of acceptance (yes, I have a huge hang up about that!).  But, yes, I am not at all interested in women so it will be wasted on me!

I think it might be sensible to have a gay guy cut for the minute (Tintin quiff?).  My hair is short and grows quickly.  If I change my mind I can always revert to silly hair.  Yes, it is part of my identity but not one that I am not prepared to jetison, at least temporarily.

oh Jay you are too nice. I only pass at a distance.

A large proportion of people in early transition will tone down their style to assist with passing. There's no shame in that, gotta do what you gotta do. Most revert back either if they are passing well or just feel like expressing themselves again.

Also don't give up hope of looking convincingly male, you might be surprised by how much you change, T is a very powerful hormone.

I'm presuming you live in Brighton? It is generally much harder to pass without hormones in areas with a large lesbian population, since people living there are used to seeing women looking butch. Try not to let it get you down. You could try having a day out in a more conservative area and pass really well.