Hi everyone. Been browsing these forums looking for basic answers to the complicated questions that have been rumbling around in my head.

First things first, I just recently came out to myself as being a transwoman. I told my best friend and the therapist I'm seeing (just one session down, but I like her). My goal is to one day fully transition into the woman I know is inside me.

My first question is being a transgender in the military. I've been in for about 7yrs now, 4 active and 3 reserve. I've already come to the conclusion that I'm getting out, but I still have a year left. Should I wait to transition until after I get out, or start things slow now and pick up right after.

My second question is about a relationship. My fiance and me have been together for a long time. She's had a very rough past with men and has major trust issues. We love each other, that much I know. The question is at what point do I tell her? When I think its the right time, or right before I start to really transition? I've been dropping little hints every now and again, but I don't think she's picked up on them.

Well, those are the only two questions I have for now. If any of you have any insight into these I would absolutely love to hear from you. Thank you!!

I would recommend not "dropping hints" but instead to tell your fiancée directly.  You may not feel comfortable telling her now, but you want to tell her as soon as you feel ready.  You have an obligation to tell her well before your wedding becomes imminent, because if she is a cut-and-dry heterosexual, then it wouldn't make sense for her (a woman) to marry a woman (you).  She may also have life plans that involve you being male, perhaps with the prospect of having kids, although it is possible for you to have some of your sperm saved later for insemination (you'll want to do this *before* you start messing with your hormones) or to go through adoption.  There are also legal issues to consider, as same-sex marriage may not be legal in your area.  Your psychologist should be advising you about this issue as well, if not right now, then very soon.

You should tell her as soon as possible.  Trust me the longer you wait the harder it will be and the more it will feel like you've been keeping a secret from her.

It's up to you.  You could get started.  See a therapist do some little things but one year is not that long to wait till your out of the military. 

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My first question is being a transgender in the military. I've been in for about 7yrs now, 4 active and 3 reserve. I've already come to the conclusion that I'm getting out, but I still have a year left. Should I wait to transition until after I get out, or start things slow now and pick up right after.

I personally would wait because transition can sometimes complicate things. Although you can do some things to transition partially (change of clothing style, slight change of voice, mannerisms etc.) it's really up to you what you think you should do.

You may also want to try changing small things to see how you feel about it, and you can take it as far as you want. Transition doesn't have to be all or nothing.

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My second question is about a relationship. My fiance and me have been together for a long time. She's had a very rough past with men and has major trust issues. We love each other, that much I know. The question is at what point do I tell her? When I think its the right time, or right before I start to really transition? I've been dropping little hints every now and again, but I don't think she's picked up on them.

It's really touch and go, on one hand she could be upset for awhile and then accept it. Or she could freak out and just outright leave you. I think you should try doing small things to transition and see how she reacts; it might give you a heads up. Also, I would advise that you should tell her quite far in advance before you start major transitioning changes.

Part of it is also how you explain it to her and what information you provide. If you outright tell her you plan on changing blah blah blah etc. she might feel threatened. Whereas if you tell her that you feel female inside and wish to express that, she may ask you questions as opposed to blowing up. It's all in the way that you talk to her; make sure she feels cared about by telling her everything your thinking: about how you're afraid she might leave you so you'd rather be honest with her than keep secrets. Appeal to her emotionally, and above all ask her to clarify something when you don't understand.

You can only come out once, so make sure you're prepared. Trust me, when I came out it was a train-wreck.

Warm Regards
-Sky

If you're really planning on transitioning and can stand to wait. I'd personally finish out the final year. There are things you can do to prepare for a transition during that year that won't require outing yourself, like your voice, building a wardrobe if you have a safe place for it, and finding your own personal style.

I am a civillian, but I work around and with a lot of military. My advice, if you think you can stand it, is told hold off on "coming out" or any notably visible transitional changes until after your last year is up. Transition can be hard enough on its own without bringing an active military career into the mix as well. I'm sure it can be done if you simply cannot stand it any longer, but you may find it more difficult than waiting until your term is up. It's certainly not too early to start discretely gathering information, thinking about things, and building up a "roadmap for the future" in your mind, knowing that your roadmap will probably change hundreds of times as your situation evolves.

In any event, may the road under your boots always bring you safely home again.

Hey,

I just got out of the military last year. I would say wait, if you feel that is an option. Do all the little things you can do in private, and just gut it out.

About your fiance though...you really need to tell them. As long as you are pretty certain these feelings are going to play a pretty major part in your life (which they most likely are), your fiance really needs to know this. Sooner rather than later. This isn't one of those secrets that hurts someone less if they find out later on. And if they feel you haven't been keeping it a secret for a long time, they might be more willing to work with you and keep things going. There are relationships around here that have survived transition. Best to start early in the process though, before marriage and kids or anything is probably wise.

I'll start with the easy one first since my wife again rehashed her 'Trust' & 'Betrayal' issues with me this weekend. You need to tell your fiancee ASAP. Oh, I know finding the right time is hard. As a former boss of mine once told me. "There is never a good time" (A real PHB. He also said "My door is always open, just make an appointment")

I also sure would not start anything transition related, other than therapy and seeking out a TG support group, before telling her. BTW-if her sticking around is an important go-forward consideration... Choose wisely young Skywalker. The odds are not in your favor.

My wife, who knew of me being a TG from about day 1 some 30 years ago and was mostly supportive and VERY understanding of the issue, has her doubts about sticking around. Her rational "I like men! I married a man, not a woman. If I wanted to marry a woman, I had my chance to". BTW - she is 25+ years post op.

There are things you can do transition related that take lots of time and money. Voice training, facial hair removal, even HRT (remember YMMV. But that is likely months away before you get cleared anyway). Oh.. and clothes! And makeup. And lots of time practicing your skills and developing a style that works for you. Hair, maybe, if you got it and can let it grow out.

Honestly, there will never be a good time to come out to your fiance. It's going to be difficult and nerve wracking no matter what. It's just a matter of a finding a space where you and she will fill comfortable and safe (No coming out at McDonalds!) and have plenty of time to talk about it afterwards, and screwing up the courage to do it. I agree with those that recommend that the sooner you come out the better. Any good relationship is based on trust and honesty, and this is a major thing that will affect both your and her life. If you hide it, you're not being honest with her, and keeping secrets is a betrayal of trust. This is going to be one of the more difficult things for you to do, but it has the potential of creating a great ally in your journey.