There is this girl that I work with that I really want to tell about my "feminine side." The only thing is that it's a scary place to be if she is not supportive or understanding. I'm not sure if she would be cool with it or weirded out by it. I was thinking of asking if I could share something with her, and depending on how she reacts, take it the next step and tell her. Maybe build it up a little by asking if she can keep this a secret and if she really doesn't want to help me then please don't feel obligated, and ask her if she would help me try on girls clothes. I'm not sure if that would be easier than coming right out and saying I'm trans. Any thoughts on how to proceed?
Maybe try bringing up the topic of gender and see how she reacts so you have a gauge. It will give you at least some kind of idea about how she may react.
It can start in a variety of ways. 1. If you talk politics, you could talk about Trump's running mate, Mike Pence. He is known for his anti-transgender and anti-LGBT stances and policies. You could talk about Pence and bring up his stances on these issues and see what she thinks. 2. You could talk about North Carolina's law that prevents transgender people from using the bathroom of their gender identity and ask her opinion. 3. Caitlyn Jenner's national exposure could be used to bridge the topic. 4. You could say, "I don't understand all this fuss over a trans female using the restroom. Have you ever even noticed a trans person in the restroom?" or something similar. 5. You could fictitiously make up a "trans person that you met the other day" and ask if she's ever met someone who is transgender. 6. The current estimate of transgender Americans is about 1.4 million people. You could say that you just read an article that told you that, and "wow, I didn't know there were that many trans people." Or some other fact that you "just learned." Do any of these ideas appeal to you? No matter how you do it, it will be scary for you until you get some response from her. The more of a big deal you make the conversation, the greater likelihood she will wonder why the topic is being brought up, so try for low key. I hope these help. Take care. ride:
Well, I did it! As I was leaving work today, I told her that I wanted to ask her something later on. She texted me after she got off work saying that I can call her and talk if I wanted. So later on this evening I texted her and asked if she was alone and able to talk. She replied yes. So with that, I told her that this is very hard for me and im not really sure how to say this but here it goes... Can you help me dress up like a girl? I think I may be borderline transgender. Please feel free to say no, I will understand. You just seem like a very outgoing girl that I feel like I could share this with you. And please don't tell anyone. She responded that my privacy is important and she would keep this a secret. She said it must be very hard for me and that she can help with finding clothes. She also told me that when and if I was interested, she can introduce me to some of her male friends that cross dress. I feel like I hit the jackpot! We are going shopping together later in the week. She seems so supportive and I was surprised to hear she had friends that cross dressed. She told me she was honored that I can trust her with this. I am floating right now. Way too awesome of a feeling!
Congratulations! You judged her character really well and handled the whole thing expertly. Good luck!