I figured I'd share the story of when I tried to come out to my mother about my gender issues, and how I realized I could never go to her with anything like that again (like my DL interests).
You see, much like my life-long love of diapers, I'd had a desire to wear girls clothing since I was a little boy. I'd fantasize I was a girl, I'd try on my mothers and grandmothers clothes when they were out of the house, and so on. I'm sure many of us have done these things.
Well, by 1998 I had got an apartment off campus with a friend of mine from college. As the year went along, it became increasingly clear that my friend had his own gender issues. Finally, on Halloween of '98 I came out to my friend about my transgender interests/feelings.
I was right in picking up the clues about my roommate, which he said he hadn't indulged in years, but used to crossdress a lot in High School, so he understood where I was coming from when I said I had a lot of issues in that regard. (Moreso actually, as a side-note, that friend came out as transsexual in 2004, and had SRS in '06)
Quietly, over the next few months I'd started to buy up women's clothing and started to wear panties every day, wear a nightie to bed at nights, wear dresses and skirts around the apartment, but never publicly crossdress.
My mother was the sort of mom who tried to be her sons best friend. She would hype up how she was always there for me if I needed to be, how "I know you better than you know yourself", and how there wasn't anything that I couldn't tell her. She'd been telling me these sorts of things since I was little.
To top it off, sometimes I suspected she knew about my trying on her clothes. A few times over the years either lay out a pair of plain white cotton panties for me when she was putting out my clothes (yeah, my mom laid out my clothes), or would put a pair in my wardrobe, or in my laundry when going back to campus. I always figured that was her letting me know it was okay to do that sometimes. (In retrospect, it was that my mother's size was pretty dang close to mine, and in her absent mindedness she was putting her white cotton panties in with my underwear)
So, with all this in mind, I figured I didn't want to hide it all from my mother anymore. I wanted to open up to her, to let it all out and stop hiding. So, one Saturday morning in January of '99, we were going to get out and go to lunch. She was parked in the parking lot of my apartment complex on a cold, rainy morning. I went out to her car a little early, got in, and told her I needed to have a talk with her.
I still remember when I looked at her, and with a ton of courage I told her
"Mom, I'm a crossdresser".
I'll still remember that befuddled look on my face, followed by:
"Are you trying to tell me that you're gay?!?"
Followed by me saying no, that I like girls, I just like to dress like a girl sometimes and sometimes I feel like a girl at heart, but I'm not gay. My mother didn't seem to understand the distinction, to her there was just straight guys, and gay guys, and if you wore women's clothes that meant you were gay and liked men. She couldn't understand what I was saying, like a big "does not compute" coming up.
Then she started to beg me, plead with me to never, EVER tell any other living being about this as long as I live. She said all my friends would abandon me if they found out (my friends didn't care, in fact some of my female friends told me in later years they basically considered me "one of the girls" since I was more girly at heart than some of the more tomboyish girls in our social circle), my best friend started calling me the Japanese term for "Dear Little Sister" as a term of affection, and my girlfriend outright encouraged it since she had crossdressing guys as a turn-on.
However, my mother, at the time thought that no woman would ever have anything to do with a guy who ever wore women's clothing, that nobody would ever be friends with someone like that, that if it ever got out it would mean that I was unhireable and would be forever single and friendless. She also said that it also might mean I would be committed to a mental institution because sane people didn't do that, but she suggested I talk to a psychiatrist anyway since maybe they could "cure" me, even if I would have to spend a few years in a mental hospital (yes, she actually suggested this.)
She told me she didn't want to eat lunch with me now, and asked me to get out of the car. She drove off. I found out later she'd almost got into a wreck twice, and had actually ripped a gas hose out of a pump at a gas station by accident on the way back (she was so confused/distraught that she stopped for gas, didn't put the hose back, drove off). She blamed me.
Over the years, she'd keep asking me if I ever got professional help. I told her I did. . .which was kinda the truth. As a university student, we all had access to complimentary psychological screenings. I'd booked an appointment with the therapist and told him everything, and he told me in no uncertain terms that as long as I was okay with it and it wasn't interfering with my life, there was nothing wrong with it. When I told my mother that, she didn't believe that any mental health professional would ever say such a thing and thought I was making it up.
Meanwhile, I had finally thrown away the last of my men's underwear and was only wearing panties, wearing women's clothes at home rather often, being rather openly feminine around my friends to the point that I was even invited to the "girls night out"
The last time my mother ever brought it up was about 5 or 6 years ago, when my parents were going through a divorce. In the struggle between my parents, my mother tried to turn my father (a career military officer and deeply conservative man) against me by outing me to him. I knew my Dad would never understand, he loves me, but I knew this was too far out of his understanding for him to comprehend. He just ignored what my mother said as insane rantings (which given how many crazy things she'd flat-out made up in the course of that messy divorce, gave a huge amount of deniability to what she said). However, the fact that she tried to use that against me a decade later always stood out as the last betrayal in the whole matter.