My (28 f) partner (30 m- according to them they still ID as male as of now) have been together for 9 years. I’m going to organize this as best I can but my thoughts are all over the place. They started cross dressing and claimed it was kink, but I noticed more and more things that indicated that it wasn’t just for kink. Such as having a lot of questions about the Trans community that I’m very unqualified to answer, but I always answered them as best as I could. Watching Finnster and Ashley on YouTube and having a bunch of questions. Preferring to wear my clothes (mind you I have a very NB wardrobe to begin with like jeans and tee shirts). I’ve asked them numerous times if they want to transition and if they want to be a girl and they got upset for me asking so much, but finally admitted they just want to look a certain way but would have no problem being called a man the rest of their lives. I think they are struggling with their identity of trying to be a manly man but also wanting to be feminine.

I’ve told them in the past that if they wanted to be a female that I would still love them. I myself have always had questions about my own sexuality because I find both men and women attractive but don’t know if I’d actually like being with a woman because I’ve only been with one person and that’s my partner as a male. They have always encouraged me to try with a female but I wonder now if it was them trying to see if I really would be okay with them being a female.

Another thing that has confused this whole situation for me is the fact that they saw the success of the YouTuber Finnster who was a lad who just started getting paid to dress like a girl and that’s what really ignited something in my partner. Like maybe they thought they found a way they could be themselves and get paid for it instead of working in a very male dominated industry? So I thought okay, so this is a hobby then? I’m confused.

I was always supportive of the things that they bought for themselves like makeup and fetish clothing and taking pictures for them to post on NSFW websites. But things got complicated for us and I’ll admit that a conversation was had that might have ruined my partner’s ability to be open with me and I feel awful about that. Basically, we had a conversation that lead to us breaking up at some point (we stayed friends for about a month then got back together) because they said they didn’t know if we were compatible anymore and it really hurt because I love this person. While we were on a break (and looking back, I feel awful about this and wish I never said it) I said, “I’m worried that this whole girl thing is just another escapism thing for you and something you see as a “get rich quick idea.” So basically they started to open up to me a little bit and I said “Are you sure you want to be a girl or are you just trying to escape societal responsibilities of being a man?” Obviously I realize how shitty that was but a recent conversation between us has made me realize how much that damaged their ability to open up to me further and I hate that because I thought I was doing my best to be supportive but apparently the way I act around them when they dress up just makes them feel judged and I feel awful about that. The only times they dress up though are for kinky times or NSFW pictures to post. it’s been very confusing because I think they are just as confused so they don’t have any clear cut answers for me so it’s hard to process.

Another thing is, I might be a bit jealous to be honest because I have PCOS and have always struggled with my own femininity and feeling pretty because I have very broad shoulders and get hair on my chin, chest and upper lip and they just look so pretty when they get all dressed up and make me a little sad. And I know I’m not their type aesthetically because they like the femme-fatal types and I very much am a plain Jane that wishes I was more. I know this is a lot to dump into one post but I’m really trying to process the guilt I feel for not being as supportive as I thought and having a partner that has changed in the past 3 years.