I've come out to my dad and his girlfriend as well as my sister and her husband.
I dress like a guy but im not on hormones and my hair is still girly.

At what point do you start insisting they call you your male/female name and using the correct pronouns, not just that but how on earth do you do it ? 

I have a feeling if i say to my dad now 'please start calling me male pronouns and Thomas' he will reply with 'but your not even sure yet and you havent been to see the therapist'. I am sure he seems to think the therapist will cure me though. 

I started to ask nicely for male pronouns right after I came out and then started to somewhat insist after a couple of visits with a gender therapist.

Mainly when I went full time. Until then I felt I had to put up with being called a he because that is how I was dressing and working.

After about 3 months on T when I started passing, and my name change was legal.  That was also about the time I came out at work (maybe a month later).

I have a militantly suportive wife. I have not had to insist on female pronouns. Sevan insists for me.

I haven't out right asked anyone to refer to me by male pronouns yet considering I do not pass at all and I'm still pretty much locked in the closet. However, some of my friends refer to me by male pronouns out of respect. But they know to switch over to female pronouns when other people are around because I'm not ready to be fully out yet.

As for how my friends started calling me by male pronouns, they were the ones who asked me.

I remember around the six month mark of hormones when I was passing a bit better I had a rush of confidence and mentioned the whole pronoun thing to my parents. My parents are very supportive of everything so far and they did well with the name change.
After a few conversations about it they tried their little hearts out to get it right but it quickly dissolved into "he I mean she.." which was just worse... it was obvious they didn't feel it was time. I ended up chatting again with them about it and telling them to not worry so much and just call me whatever you feel like at the time and that it was better to not "correct it" which just draws attention to it.
I'd rather they wait until it feels more natural (with how ever much time they need) to go 'full time' with the pronouns. They are getting better with time and like they say it's hard to unlearn something such as this when they've been using male pronouns for so many years. I know that sounds weak but if they feel that way then that is just how they are. It's more than fine I'm in no huge rush!

When I first came out, I just asked that people refer to me with proper pronouns. Some people were good about it right away, and some people still have problems with it and use the excuse... "I've known Shawn as a 'she' for years, you can't just expect me to change the words I use".
My sensitivity regarding proper pronoun usage changes, so sometimes it doesn't bother me that much to be called 'she' but other times I will flip out and absolutely demand to be referred to as a man.

I've come out to certain people and they all call me 'he' without me having to bug them.  A few will forget and they'll get a reminder of "I'm a he, not a 'she'."  And I'll repeat that until they get it right, I don't care if it makes them mad that I keep reminding them.

However, offline and with people I know, I don't insist because I know I don't pass. 

I find it really obnoxious that my friends get that my name is Kyle blah blah blah but still think I'm a she, but I'm often too embarrased to correct people, but I do insist now.

after coming out I was very easy with pronouns and tried to remind them that I was a 'she' and then after 9 months of them not really trying I said

"hey, I have given you nine months, and well.. its time for you to try now"

and they did. I get called he probably 50 % of the time now

Problem was, I never even asked anyone for the correct pronouns.  I arrived in the city that was going to be my home for the next 15 years of my life, dressed appropriately, hence, if anyone spoke to me, I was addressed correctly.  But then again I was to nervous to worry about pronouns.

After 3 months of preparation, doctors, name change and finally getting a job, I was too busy worrying about these things to even consider if pronouns were being used.  Vaguely, once in awhile I was aware of others using the correct pronouns and I was aware of using the correct pronouns myself in regards to others that were changing.

I never came out to anyone, my uncle only new some things about me, but not everything and in a sense I will never come out to anyone. Then my uncle spilled the beans.  Eventually when I caught up with individual members of my family, I said I will only answer to my name and totally ignore my previous one.  As far as I know I never even mentioned pronouns.

If I ever did mention to anyone in the correct use of pronoun, it would have been very rare event indeed.

So what can one make of all this.  I suppose it depends on how you want people to address you and only you can decide how it is done.  In my case I was just a female and of course people responded with the correct pronouns.  Therefore I never insisted on people using the correct pronouns with me.  They automatically corrected themselves.

Take care and all the best.

Kind regards
Sarah B

once my name was changed I went full time that is when i would ask the she is the proper pronoun

but you have to remember "how are you guys doing" is a saying use all the time with no gender
implied and there is a lot of slip ups, and one cant be so senstive about it .  but it does bother me when it happens welcome to life
Bethany

I've stopped worrying about it.

Close friends have said 'we are going to make mistakes, sorry' And that really doesn't matter that much to me.

I'm not (often) referred to as a he in public by people who do not know me. If they are shop assistants I have complained to management, with great success. If they are individuals being insulting I have no problems with that. They are so irrelevant to my life I cannot think of a single reason to respond to them.

I think, and this may seem stupid. Why is it insulting to you?
They are just ignorant

Cindy

To be honest I never really have. It just doesn't seem that important.

At the same time I can't actually think of a time in the last 25 years or so when someone really got them wrong, but if they did, as long as I didn't feel they were trying to be clever or funny with me I'd just let it go.

For me life just seems way to short to worry or lose friends over such things.

As soon as I started dressing full time outside of work I insisted upon it people around me except coworkers because they still didn't know yet. When I went full time, it was just expected and encouraged.

Mind you, my ignorant hateful parents still call me by my old name and "son" and with male pronouns.

Now that I've come entirely out, wear women's attire exclusively and makeup routinely, I've noticed I'm pressing the matter a bit more.

At work, I simply stress that in order for me to really do RLE, I can't go to men-only places, do men-only things, and must socially transition as thoroughly as is reasonably possible.

But my sister chose to stop going by her given name in favor of a variant that she felt suited her better when she was in college. After many years, I still frequently call her by her given name. I try to remind myself of this when I press people to re-gender me and switch to Sydney.

The only people I don't ask to call me He is my family, and old, old friends.
I feel that since I've waited forever to tell them who I really am (which most were accepting), then they can if they wish wait to call me by the proper pronoun, and call me He when there ready. Whenever that is (getting slightly impatiant) But everyone else, I tell them right off the bat that i won't respond to anything but my name and he.

hmm well i haven't told anyone yet to refer to me as 'he' but i am getting a little frustrated with the girly pet names. Take for example my dad, throughout my life he constantly called me masculine nicknames such as 'timothy' and 'tiger' . As soon as i told him i wanted to be a boy he started called me his 'little girl' and 'love'. Annoying

At work: 2 weeks after everyone knew STILL have to correct the OLD people ever now and then. 1 week after told dad (last person to know) Didn't have to with Phoenix (Best Friend) nor Zataku, still explaining to Hyate (2 years now) and have to rarly correct Reiko and Advent (those two are brothers)