Hi Sammy,
Hmmm, I suppose it makes sense. People are going off the past presentation and behaviour. I know for myself that I was a fairly good chameleon but poor enough to be asked growing up by my father whether I was on drugs... LOL... I was teased about being gay. Nope, but when I transition I will make a great lesbian.

So, I think part of it is that I became good at presenting as a regular guy to protect myself with a few softer traits so that I didn't go mad. When you add that presentation with a body that shouts male then how could it be!? Well at least that is what many think because that is what for them was the reality versus what was going on inside us. The funny thing is that barring a tough first week after telling my spouse (needed to process it), she actually agreed. Over time, all the things she liked best about me was my feminine, softer side that I increasingly allowed out. When renting movies with the family I started to select movies that were more female friendly. At first, they saw me as just being accomodating, then as perhaps a little sensitive, etc.... Everytime my wife and I discussed changing the way we live, I began to express that I wanted to be at home, cooking, spending time with the kids, writing, doing photography, cuddling, etc.. etc. The more she saw what I had kept hidden the more she liked what was coming out. So, I suppose that I didn't try to convince her. I just started allowing to those closest to me to see more and more of who I really am and then after a while when the time was right came out to them. So far, it hasn't been an uphill battle with the few people I've told. The bigger challenges are those who see me less.
At work, I'm not out but I've slowly shifted again so that the purchase on their mind isn't as difficult. A few changes in clothes that are more feminine and colourful. I engage them on occassion on more female centred topics as they come up on coffee breaks. I try to be a little less aggressive in meetings and foster listening to the women at work (stunning how easily men get deferred to...). I'm not out at work, but as time goes by I don't think it will be as difficult as would otherwise be the case.
For me, this slow transition has worked. I progress every day and people are slowly changing their perspective of me. The mental leaps for them have been much easier. But I suppose the cost is that it IS SLOW and you may not be able to wait that long. I know that at times, I just want to do it damn it... Sammy, I don't know if this helps or not. I just started with one person at a time and slowly let me out versus the more neutral, protected persona that I played and in a way was for a time. No longer, the world seemed so grey to me.