To start off, I am by no means a stranger to what it is like to be transgender.
However, I am hoping I can receive some advice on how to best handle this change.
Over the course of the past few months, I had noticed some "red flags", if you will, being thrown up by my s/o.
She always carried herself in a rather effeminate/flamboyant manner, from the very way she would walk, to the gestures she'd use in conversation. It was just very uncharacteristic of general cis men to the extent that her own friends always assumed she was gay (which is stereotypical and rude, but I digress).
I started to pick up on other things as I began to pay more attention to the way she carried herself and the things she'd off-handedly say/do. She's very particular about her appearance and had absolutely no issue with wearing face masks with me/allowing me to pluck her eyebrows if they were getting too unruly/never wanting a hair out of place.
One day, as I was doing my makeup getting ready to go out to dinner together, I jokingly asked her if I could do her makeup. I wasn't expecting her to be so okay with it, but she excitedly agreed. When I told her I was only kidding, she practically insisted that I do it. I raised an eyebrow, but I rolled with it. A half hour later, and she's rocking winged eyeliner, dark lipstick, long lashes, and blushed cheeks. When I offered for her to take it off before we left, she shook her head no. This would not be the first time this happened, but it was the one time that I did it for her.
As time progressed, she would get into my makeup and come out of the bathroom with fire engine red lips and some well-attempted eyeliner. She gave no care in the world what anyone said when we were in public like this. My girlfriend can easily handle herself. She isn't very tall, but she is broadly built/stocky with a lot of rambunctious energy. I think that is what kept anyone from saying anything about her, at least not within earshot.
Noticing these signs, I had quizzed her a bit about how she felt about herself. Her ex before me was a trans girl, so she was by absolutely no means a stranger to the idea of transitioning. I expressed that I would support her no matter what and help her through the process if that was the case. Still, she vehemently denied any gender identity issues, stating she was comfortable with who she was and that she "would make an ugly girl" (this she said while laughing, I'm sure with the intent of warding me away from the topic). I decided to drop it for a bit, but I still continued to observe the signs.
Of course, because she had been getting a taste of feminine expression by me indulging her with sharing makeup and even allowing her to use my perfume/deodorant if she wished, her need to express herself further in that regard increased. I began to come home from work on the days we didn't work together to my clothes in my dresser/closet suspiciously out of place. I pretended to not notice, but it finally got to the extent that my lingerie drawer looked like a small child had been rifling through it. Upon confronting her, she admitted to trying on my clothes when I wasn't around. Although I was admittedly upset with the fact she was wearing my underclothes behind my back, I chalked it up to trying to avoid potential embarrassment and sake of ease of obtainment.
As we laid down to go to sleep that day, I once again asked her. I told her that I didn't want her to end up like the stories I read about people denying their gender identity until it was much later in their lives before finally coming clean, that I didn't want her to continue to live a lie when she didn't have to. I finally broke through her wall, and the tears flowed down her cheeks as she still tried to make excuses for why she shouldn't.
"My family will disown me again. (she'd just gotten on good terms with them again because they disowned her for dating a trans girl) You know it's dangerous with our job. (we work as correctional officers in the biggest prison in our state) I want to be a father our child. You know I had to grow up never truly having one, I don't want that for our baby. (we've been trying for a child for a few months now) You wanted a husband, not a wife."
I reassured her that we could make our own family and that her family would either have to eventually come around or miss out, that she knows how to protect herself and our job would most likely switch her to a safer post, that a child with two mothers would be just as loved and nurtured as a child with a mother and a father, and that I'd take her as she is and be happy regardless of whether I marry a bride or a groom, so long as I got to spend the rest of my life with her.
She finally agreed, so I picked up my phone and scheduled her a therapy appointment with my old gender therapist. She cried into my shoulder and thanked me over and over again as I kissed her head and reassured her that I loved her immensely.
Since this happened, I've went shopping at the store with her and bought her underwear and bras, pretending to be shopping for myself while she played the "unenthused s/o who just wants to escape the lingerie aisle" part so it wouldn't seem suspicious. Soon, dress shopping will happen, as she's begged me to take her to buy a flowy dress for the warmer spring weather. I've been working on teaching her how to properly apply her eye makeup and soon I'll introduce her to the whimsical world of contouring. We've been looking up makeup videos specifically made by trans girls so I can help her make her face look rounder and more full until estrogen can begin to help out in that regard.
I will admit that this has been a bit hard on me. I'm still trying to make the 100% mental transition from viewing her in a masculine manner to feminine, and as much as I love her and want to support her wholeheartedly, I can't help but feel a sense of.. loss? I am losing my spunky, strong fiancé, but I am gaining a beautiful, soft fiancée, so why does it almost hurt?
I also admittedly haven't been able to bring myself to have sex with her. I know that might be TMI, but I'm so afraid of triggering her bottom dysphoria that even though she's told me she's extremely sexually frustrated, she also tells me that she wishes she could just cut "it" off, so I feel stuck between a rock and a hard place. I'm also afraid to be intimate because that just goes back to viewing her in a masculine light.. besides the way she's dressing and her makeup application, there really isn't much difference just yet, so I'm worried about how I'll mentally associate it all. It makes me feel sickeningly paranoid and guilty to feel that way, so I really need some advice in that area if anyone has some.
I'm sorry to end this on a seemingly negative note, but I do love her so much and I have full intentions of staying with her. It would just help to have any sort of input from someone who knows how I feel, either from my own side of the situation or from her side of it all.