I just finished replying to your introductory post regarding your relationship with your friend.

I'll just mention here, for reference, that I'm a "senior citizen", as us older folks are frequently referred to. I'm male. But I've waged a life-long struggle with my gender identity. Whether or not I was actually what is now referred to as "transgender", is something I still puzzle over. Sometimes I think I was. But then sometimes I think my gender dysphoria was simply one aspect of a broader mental health problem. (It's a long story. And I won't bore you with the details.) But having spent my whole life struggling with my own gender identity, I do feel I may have one or two thoughts I can offer with regard to this post.

You wrote you lost your job... one at which you were not being successful. You feel down & stupid for not being able to work harder. Then you mentioned you happen to like to wear women's clothes. You fantasize about growing breasts & being transgender. So if you won't be successful establishing a career, getting married & sorting out your relationship with your friend, you feel like turning into a woman "as payback" for what you accidentally did.

I'm not a mental health professional. So anything I say is simply my own personal opinion. But I have to say, in all honesty, you sound very confused. There seem to be at least 4 different concerns that are all twisted together. First of all (perhaps you already know this, but just in case not) there are people (primarily men) who are what is typically called "crossdressers". They're not transgender. They're comfortable being men. But they enjoy wearing women's clothes (which you indicated you do.) Then there are people (both biologically male as well as female) who believe they "should" have been born the opposite gender. How they perceive themselves does not match their physical anatomy. These individuals are included within the term "transgender". So, to me, the first thing you need to do is to figure out whether you are a crossdresser or whether you may actually be transgender. Does that make sense?

In my case, my struggles with my own gender identity go so far back into my childhood that some of my earliest memories of life revolve around it. However I do know that other trans individuals sometimes discover their "transness" later on. However, at least from my perspective, one is either trans or they're not. And one should never, ever attempt to adopt a transgender persona as a way of punishing themselves for failing to achieve things in their lives they had hoped to achieve. If you're not truly transgender it makes absolutely no sense to try to become transgender as a form of self-punishment. That is, I would venture to say, tantamount to self-abuse.

At the end of your post, you asked what you should do. I would have to say that the thing that needs to happen here is for you to find a mental health therapist you can work with over a period of time to untangle all of these threads & figure out what truly is going on. As has sometimes been said, if you're trans, you're trans for life. It never goes away. But if you're not then you're not. And using that as a means of punishing yourself for your perceived failures would, at least to my mind, be a terrible thing to do to yourself. My best wishes to you.