Some of this I cannot give you any advice (the part about you making others happy) because I don't agree with the behavior or think it is even possible to do as you will always piss someone off no matter what you do. So I will mostly address the last half of this. You need to go to a therapist. that is your "next step" that you are looking for. You are simply going to sit in this limbo without that. It doesn't matter what you try to do from here, without doing that you won't find anything to help you other than maybe someone to listen. Anyone can claim that they have x or y thing going on, but without the evidence...... So therapist for evidence period. Far as affording it, you neglected to give any indication where you are from, but in a lot of countries (the USA included) transcare is now part of insurance. So aside from some co-pays and treatment limits per year, that is really not much of a thing. If you are in one of those countries that is horribly trans and homophobic then I recommend keeping it quiet in general as in most of them they kill you for it. Next is that fantasy of some rich person and so on. That sort of life would not be safe nor healthy for anyone. Being completely dependent on others is never a wise choice. People come and go, relationships are built and crumble, you listed 2 past marriages so you know this. Being dependent on them for everything and such is not a safe path in any sense of imagination. It puts you in chains. The dreams of having money, fine, the dreams of someone doing it all for you is dangerous and will lead you to situations that could be very hazardous to your health. So be very cautious of that. Abuse, both physical and mental, in relationships is not an uncommon situation for trans people as is homelessness from such situations. So therapist, and seeing what you can do. The fact is that there is an entire spectrum to gender and there is no set place to get to, you do it as you are comfortable. I have been at it for 8.5 years now, I am scheduled for my surgical consult and all. But 8.5 years! why did it take me so long? The first 3 years I spent going to therapy, getting on hormones and all the things I could do without having to let anyone know but keep my sanity. Eventually I felt the push to come out and did and I have gone from there slowly. Some jump right in, some never have surgery, heck some never decide they want hormones. That will be between you and medical professionals, but the first step is that therapy. Beyond that I can just say stay grounded and keep your wits about you. There's no race, there's no time limit, there is just getting to where you are content. It takes strength and determination to get there, others have done it and so can you. You just need to get yourself a roadmap and plan your route best you can.

Robkin69, although it's not funny, I could have written a lot of what you wrote. I knew a girl was inside me and I'd been born wrong. I've known this since about the age of 9 also. Most girls I've read about seem to know well before that but you and I are just late in finding out. You're very lucky in a way in that you seem to have discovered your inner self without therapy. I, on the other hand, needed a bit more assistance. Like you, I'm experienced. 45 years of marriage, kids and grand-kids and finally I am able to accept the woman that I am. Like the "WyndWytch" says, you gotta find a therapist. Could be a Clinical Physchologist, like I did, or a Psycariast that you trust and confide in them who you are and where you've been. they'll direct you from there. I, on the other hand, told my personal physician, who referred me to an endocrinologist, who told me I needed a letter from someone working in the mental health field before I could begin HRT. Since I was already seeing one it wasn't a problem for me to get the letter. .... I also fight with my concience about my obligations to my wife, children, grand-children, friends, etc., etc.. In the end, when you are finally done arguing all the people you are inconviencing, the number one person being inconvienced is you! let that sink in a minute. You are important, you are entitled to happiness as much as all those that are obstacles and how much more can you give to them each when you are finally free from inner turmoil. I can give a 100 reasons, very good reasons why I shouldn't transisition, but I can also give one good reason why I should. Because I am tired of living a lie. I'm not the person you think I am, but someone much better. My transisition isn't about other's, it's about me. Other than my therapist, my wife is mostly supportive and I have one friend that is completely supportive and beyond that I'm walking this journey alone. .... Whatever you do, find a therapist soon and take the first step. --- finances a problem? talk to your physician, inquire if there is a LGBTQ group in your area that can refer you to someone that will see you for little or no money. ..I agree with WyndWytch that depending on what country you are in, it could be hazardous to bring it up, but if you are in the USA, as I am, than not so much. -- good luck. :)

I could not have stated this better and it made me feel better too!

I really appreciate the responses to what I posted. I will address some of the things I left out or was vague about. I am in the US and insurance will cover quite a bit, but I am in a financial situation right now where I can barely afford to pay utilities and rent. I am waiting for a decision on SSDI and I am unable to work. Also, I live in an area where not too many people would be accepting and supportive, including family. As far as the fantasy of a rich benefactor, it is exactly that, a fantasy. Don't get me wrong, if I could be granted the wish of meeting the man, or woman, of my dreams, falling in love, and them offering to help cover the expenses of my transition, I would have a hard time saying no. On the other hand, if I could be granted a wish, I'd most likely just wish to be a GG. I know what I need to do, get a psychiatrist/psychologist, get on hormones, etc. I'm just scared to get started while I feel this alone and without any support. I can't say that I feel depressed, but I am sad, afraid, and lonely a lot. Until I get approved for SSDI, I am living with family and rely on them for transportation to doctor appointments. If I came out to these family members, I am afraid I would lose their support. I just feel trapped. Sadly, all the reasons I feel trapped come back to the genetics of the body I was born in.

So with the family and the people around you... there are a couple things that may or may not help you. First is that there is nothing you can do in the immediate that is going to give them pause. Now what I mean by that is, you have the ability right now (assuming you do your own laundry) to have women's underclothes and all. Over clothes it is not uncommon for women to wear men's clothing and in some cases you can get women's cuts that look like men's. That could help some in that you are basically hiding in plain sight. The other part is that hormones and all that take time to cause physical changes that will be obvious and impossible to disguise.
The second thing that might help is that you don't have to tell them what he appointments are for or you can tell them something generic. You list here you have depression, tell them you are going to therapy for depression. Depending on your insurance and what it covers, its possible that at least the therapy would be covered fully. If that is the case then it will just be getting to the appointments.
In the long run this journey we will call it, is not about changing the body nor the mind so much as becoming comfortable with ourselves. So you need to find what will make you happy and go with it, if that means hiding in plain sight then do so, if it means hiding then that is fine too. You are on a path with the SSDI that will take time, so will the trans thing and neither is really completely dependent on the other. That said, it will cause stress having them combined and coordination is a pain, but you do not have a stamp on your head or a big sign over it. Most people will ignore minor anomalies so you can get by with subtle changes for your own comfort in the short term at least.