I hoped, wished, and dreamed I wasn't TG for a good 50 years. Add in 7 more after deciding to take on the trans-beast for real this time. Most of us will tell you No one WANTS to be TG.
I grew up in the shadow of NYC in a city filled with first and second generation of European immigrants. Men worked, they drank, they ate, oft time a lot. They hollered, sometimes fought. Most of what you see in the movie epic "On the Waterfront" was my world, besides taking place one city or so over. Most of the Soprano's was filmed within a 20 mile radius of my world.
Men also don't "share their feelings", nor eat quiche. My wife, on the other hand, is a world class sharer, usually going into TMI. She self describes as Pathologically Honest. Her favorite question to ask others is "What are your hopes, wishes, and dreams?" She got an I don't know. No way was I going to fess up to the one hope, the one big wish, the one almost dead dream all but stuffed away forever.
After dropping the T-Bomb I needed to come up to speed quickly on this "Sharing" stuff. Besides having lived with a pro for ages, I got some training by going to a TG support group. When you don't fall victim to the Earth opening up to swallow you, or not so random bolts of lightning landing on your head, you aren't so hesitant to try it out for real with someone you love and are afraid to loose.
Another big problem early on after coming out is all the inner turmoil as you realize more and more how totally overwhelmed but not knowing. Not having a clear idea of who you are anymore. You start out thinking that after the better part of a lifetime you have some sort of a handle on this. But the reality of dealing with the reality makes you question yourself and look at things in so many different ways.
Especially the "I can really beat it this time" way.
You can try, like my wife and I do, "scheduling" a time and place for a serious grown up talk. Then have a top question or two. The answers to which my be an I don't know, some non-sensical stream of consciousness babbling. Your questions may not have even been thought about before by him, or too scary to.
Also expect some raw totally unfiltered reptilian emotions to be voiced, by both parties. Even a reminder/warning before the start that it may happen but keep in mind it's said out of love and not meant to hurt. Simply unfiltered. And try not to get sidetracked by the words themselves, rather hear the message.
And then, I've seen it help for SO's, go to a TG support meeting together. How that can play out depends on the group. They all have different personalities