Hello,
First, let me start off by saying that I am new to this site. I've read some of the forum topics every now and then over the last year (bit more on that in a minute) but I just made my account and this is my first post. That being said, if this is not the correct place for this post, I apologize.
Now a little back story of where I am at: I am currently 29, I'll be 30 in May. In the past, ever since I was very, very young (about 1st grade) I've crossdressed. At first I just tried on my sister's clothes every so often and this is something that kind of came and went from time to time. I grew up with pretty conservative parents and in a relatively conservative area (the school I went to is considered a "farmer" school around here, in that most of the students live out in the country and those who live in town tend to have parents who grew up on a farm, the joys of living in the mid-west I guess).
Just under a year ago now, I finally got to the point where repressing my feminine side just wasn't an option any more. At first I just wanted to be able to crossdress around the house and so I told my wife about my crossdressing and that I wanted to explore it further. She was a little shocked at first, but very supportive and still is, in fact she has given me a few tips for my makeup and we go get our eyebrows waxed together on a fairly regular basis. Over the last year, I've read up on transitioning and I've told almost all of my friends, my sister and her husband and recently told two of my cousins and so far I've gotten nothing but love and support.
I've been seeing a therapist and she recently told me that she would write the referral I need to go to the next city over to start the transitioning processes (not sure how it is everyone else, but around here there are no doctors who actually specialize in transgender issues, so we have to go out of town (about an hour drive away) to see a doctor and get started on HRT). The only thing holding me back from making the first appointment is that I want to tell my parents before I start the process, not really sure why, but I do.
I've searched all over for tips and advice, but I haven't found anything all that helpful. The information I've found has been helpful to an extent, but more covers the idea of telling as many people as possible who you believe will be supportive before telling the people you are nervous/hesitant about telling. While this information is nice, it simply doesn't help my exact situation. Also, most of the information I've found has been geared towards the younger crowd, such as teenagers and early twenty-somethings who still live at home. As I said above, I am currently 29, married and am not financially dependent on my parents at all at this point.
So, my question is this: Is there anyone who is or was in a similar situation of what I've described? My mother is religiously conservative (yay) and my father is more of a social conservative. I know both have negative thoughts towards people like Caitlyn Jenner and one of my cousins (one of the one's I've told) is gay but terrified of telling my mother (nearly our entire family knows, but he hasn't openly talked about it to very many of us, and as you may have guessed, my mother is one of the people he's never mentioned it too, even though she knows). He worries that once he confirms it with her, she will never talk to him again. He confided this in my sister some time ago and she told me that she brought it up to our mother and she said "Oh no, I love *name omitted for obvious reasons*, regardless of his choices". She doesn't seem to understand that it is the fact that she sees it as a "choice" that makes her seem so hostile about it. So this might give you a better idea of how she is. As far as my father goes, when he was helping my wife and I move into our house a few months back, him and I passed a house where someone he and my mother knows from way back lives. This person happens to be a hermaphrodite. I was unaware of any of this (literally never heard either of them mention this person before) and my dad pointed out the house saying something to the extent of, "We know the woman that lives there, but she's really a guy, know what I mean?" I decided to say no and asked him to clarify and this is how I found out she was born with both male and female genitalia and her or her parents (no idea who made the choice or when) decided she was female. So that may give you an insight of how he sees the world.
Does anyone have any advice on HOW to tell them? The idea I have right now is for my wife, sister, brother in-law and I to go to their house. My wife and sister would be there for moral support and all three to help make sure the conversation doesn't derail. I've been thinking of writing a letter and reading the letter to them. Another idea is to just wing it, which is what I've been doing so far and I've gotten... I guess, good (?) at that approach, but I'm not sure if that's the best way of telling my parents.
My sister and I have ruled out the idea of taking them somewhere to tell them, so that they can feel free to have whatever reaction they need to and so that my dad can smoke (he's a heavy cigarette smoker and will unquestionably need to smoke one or two after I tell them). We've talked about telling them separately so they can have their own reactions and not "feed" off each other, but think this would be difficult. So as of right now, the likely scenario will be all of us sitting in their living room, me reading the letter to them with my wife, sister and brother in-law there to help make sure they let me get all the way through the letter.
At this point, I understand it might sound like I have it all figured out, but honestly, I don't. Considering how conservative my parents are, and their age (my mother is nearly 60 and my dad is 72), do I just come right out and tell them or slowly bring it up? Should I consider having only my wife there so they don't feel like we are ganging up on them or would having my sister there as well help? Should I do the letter thing or just wing it?
Any help or advice on this topic would be GREATLY appreciated. I need to tell them soon as I find myself nearly blurting it out whenever I go out to their house to visit and I want to start embracing my new self publicly, but need to tell my parent's first so they don't hear about it from anyone else and such.
Thank you in advance,
Emma