Coming Out to my SO

I just skimmed through a WikiHow about a youngster writing a coming out letter to parents. It is not unheard of and it certainly would help if you are nervous.

If you decide to do this, take enough time to get it right.

I’m probably the wrong person to tell you how to tell her but I am the right person to tell you not to put it off!
I put it off and regret it tremendously! 

Maybe you could write the letter and then sit down with her and read it aloud! 

Hope it goes well for you,

1. Sheryl

Bella. 

Everyone had to come out to their SO in their own way. We may be able to pass on advice to you, but you are the only one than can decide how you want to come out to her. God knows it isn't easy. If you feel a letter is the best approach for you, then write the letter and practice reading it until you feel comfortable enough to  present it. I am thankful that my wife is a very accepting of my dressing. We sometimes shop together. I am there for support in spirit. 

Writing a letter sounds cold and calculated, like a legal procedure. And, you are putting in writing what could be used against you later.

Think about it. Is this the way you would want to hear this if the roles were reversed?

If you already wear some of her things with her knowledge, make it a mutual exploration. "Honey, you know how I've been wearing some of your things to bed? Well, I was wondering if you could maybe loan me some more things and help me try them on. Just to see what it would be like. I'm kind of curious."

If she reacts with disgust and absolutely refuses, you have your answer about telling her. If she goes along with the idea, go freaking slow with adding new dimensions. Go at her pace. She may even be into it, who knows?

I agree with Allie, but want to add one more option. Write such a letter, but do not give it to her or read it to her. Write it and file it, or tear it up. You can use a letter to organize your thoughts and find the best way to express yourself, and when it is very clear and organized in your mind then sit down and talk with her. Mind you, I think the other optiins a valid as well, it just depends on how you as a couple best communicate.

I agree with writing it all down to make sure you have it as clear as you can be,  but i would NOT just hand her a note, even if you stayed while she read it.   Have a discussion with her, be prepared to answer all those typical questions and anticipate what she will ask you and prepare a answer for them as best as you can.

Honesty honesty. Place the two of you someplace quiet and tell her you have something serious to discuss and then pour your heart out. That’s where you start. Wishing you all the best however you decide. 
Robyn 

Thank you everyone for the responses. They were all very helpful to get more input and insight into how to handle this conversation. 

Last night I tried to speak with my SO. It took me a long time to work up the courage to say “can I ask you something?” And she could tell something was up and I was nervous leading up to it for sure. 

But I eventually did, and instead of reading the letter, or handing it to her I ended up using it to help collect my thoughts. I started the conversation by asking “how does it make you feel when I wear leggings or high socks?” 
She replied very calmly and she could tell this was a sensitive subject for me, and said that it definitely threw her off at first, but that she’s used to it now (its been about 3 years that I’ve done this in-front of her at home). I kind of said I haven’t really known why its a thing for me. Which is true, I haven’t, and I’m only just starting to understand and accept the actual reason.

After going back and forth a little bit more I ended up asking ‘did it make you think I might end up transitioning to a women back when I first started?’ 

Now before I continue I want to be very, very clear, I don’t believe there is anything wrong with transitioning, but that subject can be scary for an SO to hear because I know for my wife specifically, her brain probably hears “I want to eventually transition and leave you” and she has expressed that as a concern before, that her biggest fear is me leaving her and our children. That is the absolute opposite of what I want her to feel. She’s always been very accepting of LGBTQ people, but I would imagine hearing that her husband all of a sudden isn’t who she thought she married would be concerning. 

So I asked that question, and she said that at first it was a worry for her, but not so much anymore. I still took the time to assure her I have no plans of ever leaving her. She is my wife and I am her husband. That will never change for me. I also let her know that I don’t personally have any desire to transition, which is the truth, that wasn’t lie to her just to make her feel better in the moment. 

We talked about it some more and the conversation kind of ended with her saying she’s thought that maybe its a ‘sensory’ thing for me to want to wear tight fitting clothing, similar to how people own weighted blankets and that maybe it makes me feel safe. Which I do think I can agree with, but obviously isn’t the full breadth of why I do it and wasn’t fully where I was trying to get the conversation to go. 

She had already communicated earlier that she hadn’t been feeling well yesterday (allergy season in NC is WILD) and she started changing the subject and wanted to go to sleep so I didn’t try to force more out of her. I could tell she was done for the day so I left it alone for the night. 

She definitely didn’t seem upset, frustrated, or confrontational about the conversation, but it was still challenging/awkward to have for sure. 

I think because I didn’t quite express the full extent of what I’ve been feeling, I think I am going to write down what I want to say and read it out loud to her. I definitely see the points some of you shared about a letter being ‘cold’ or insensitive so I definitely don’t want to just hand it to her and let her figure it out. I more so want it written down so I have it all there laid out for myself and I don’t get off topic or chicken out 😬

I do feel very good that the conversation has begun and hopefully the wheels have started turning in her mind. It makes me feel better that once I really do explain the full truth it won’t be totally out of left field for her. 

Bella

Today I finally worked up the courage and did it. I knew I was going to, but I was too terrified to bring it up but she could tell something was going on and asked what I needed to tell her.

Her reaction was honestly surprisingly good. I think she was more relieved that I wasn’t telling her that I had cheated or something like that. I told her that I thinks its been there since I was young but didn’t have any understanding of it and I knew I wouldn’t get support. I told her its been on my mind enough lately that I felt like it was too significant to not share with her, even though I felt very embarrassed at the thought of telling her. She said she doesn’t want me to feel like I need to hide things from her and that she’s glad I told her. 

I was more than relieved, I couldn’t believe it. She even started doing some research on her own about it to learn more. 

Later on this evening I asked if she would want to watch a video of a therapist explaining more about crossdressing and some of the misconceptions, etc. and she agreed. 

This first 30 seconds of this video uses terms like LGBTQ, makeup, wigs, crossdressing, and I could feel the awkwardness and tension rising without even looking at her. I ended up just turning it off and saying we don’t need to watch it and she just apologized.

We stayed silent for a long while. 

I eventually spoke up and apologized for the video being a lot all at once. She said she thinks she needs more time. I told her I don’t want to force her into an uncomfortable situation. She responded with “I don’t know how to be supportive of something I feel very uncomfortable with.” 

I’ll just have to wait and see what she feels. I made it clear I have no desire to leave her as I’m still very in love with her and attracted to her. The bandaid is ripped off now. 

Still not sure if telling her was the best thing. I’m sure it will be in the long run. 

Bella