I'm 36, and inside I've always been female (albeit a tough one). I'm still male, but I've arrived a point that I don't believe I can live as a man any longer. I'm afraid though that the years have significantly reduced my pass-ability. When I was in my twenties I was immersed in Goth culture. My makeup was so skillful I was often mistaken for a woman: I felt cute, wanted, desired. Now that I'm older and have lived a life of faking masculinity, I'm worried. I don't yet have a specializing therapist. I have an appointment with my analyst (yes, a real psychiatric practitioner, not a psycho-pharmacologist). She does know that I have had ongoing gender issues my entire life. What she does not yet know is that I very much want to take the first steps along the path. Of course I don't know how she'll react. She may believe that my stability must questioned, which I can definitely understand. I'm hoping she can make a recommendation for trans-gender counseling.

Here though; I'm not interested in total gender reassignment. To put it bluntly (and please pardon my French) I want to be a chick-with-a-dick. That means HRT and some other less extreme surgeries if I so choose.

How in the hell do I begin to tell any of the people in my life about this. It's going to be a serious bomb-drop. Any suggestions?

If your therapist is a psychiatrist you won't shock her. 
As for HRT, that will put downstairs out of action within a few weeks, and remove male sex drive if it is doing a proper job.  Sounds like you don't want that, so I'd be doing a lot more research before making any decisions.
First thing is to talk to your therapist and if necessary get her to refer you to a Gender specialist.

Karen.