My Amazing Sister

When I was around the age of five or so, one of my sister’s best friends came to to live with us.  I didn’t know all the reasons why until I was older.  My mother actually went ahead and adopted her legally.  I won’t go into all the reasons for what seemed then to be such a crucial and important situation.  Talking with my sister last night, I explained that I had become a member of what I believe to be a very elite social club for Crossdressers, Transgender, and even me, a Crossdressing Drag Queen.  I explained the forums, the articles, and the many other qualities of Crossdresser Heaven.  I even gave her the URL so she could check it out and read some of the articles and things for herself.  Asking her if she would mind if I wrote this article today, she told me to go for it as long as I left some parts out.  (Us ladies must have our secrets.)

My sister has always been a huge support to me and someone in whom I always have been able to trust and confide.  Even before she moved in with us, she was always on my side.  Every time I got angry with one of my other sisters (I have four), she would jump in and defend me.  It was only afterward that she would tell me to straighten up.  Anyway, as one can imagine, she quickly became my favorite and later my inspiration and in some ways mentor.

I was getting into everything of my sister’s by the age of nine or ten.  By twelve, I think that I may have tried on and worn practically everything she owned including her makeup.  In fact, there were a few things I believe I wore more than her.  Elaine would come into my room and ask me if I had been into her makeup, clothes, perfumes, and other things.  No I would say, why would I get into those things?  My other sisters believed wholeheartedly that I was the culprit for missing things like eyeliner, mascara, foundation, eye shadow and so much more.  I think every one of them had asked me if I was wearing makeup more times than I could count, usually because I had not gotten it all off.  You know how eyeliner and mascara have a way of mysteriously reappearing on your eyes, even when you were sure you got it all off.  She was always so mellow about it whereas my other sisters became raging maniacs about it.  Elaine would always stick up for me though, even when she knew I had done something wrong.  She spoiled the crap out of me is what she did, and I could not help but love it and take advantage of it.  She would take me with her a lot of the time to places like her friends’ houses, the salon (which for some reason I loved), shopping (which I also loved doing), and even cruising downtown in my mom’s car a few times.

It was mainly Elaine who finally convinced my mother to stop having my hair cut after more arguing and yelling than I care to remember.  It was the 70’s and long hair on guys was the cool norm.  I think it had been growing for around two years when one day while at the salon with Elaine, I pointed to a hairstyle on the wall and leaned over to say “I want my hair like that.”  After some whining and fake almost-ready-to-cry signs, she said “Okay, are you sure?”.  I told her I was more than sure, and she agreed to pay have my hair styled for the very first time.  As expected, my mother freaked out when she saw my hair.  It was still long, but layered, feathered, stacked, and had highlights which were pretty much called a frost back then.  She asked me who did it?  I told her.  How much?  I told her.  When?  I told her.  Then she asked if Elaine had any say in it.  I told my mother no, and that I had went and had it done on my own with my own money.  I asked her to quit freaking out.  She thought I would get harassed and picked on by other kids because of my appearance.  She was convinced that I was was doing whatever it took to look like a girl, which in truth I was.  If only she could have seen me when I was wearing makeup, a skirt, heels, and other accessories.  She would have really freaked out.  But once more, I defused the situation and conversation and went on about my way.

My whole reason and point in writing this article are to express my love and respect for my sister, Elaine.  I love my other sisters as well, but I have never bonded with them as I have with Elaine.  The day I chose to confide in her and tell her all there was to tell was one of the most frightful days of my whole fifteen years of being alive.  And tell all is what I did.  Even though I trusted her and knew she would not tell anyone unless I consented, I was scared and nervous as all hell.  I decided that I would not go crazy with the makeup or get dressed like a raging queen, but I was going to be apparent and obvious.

When I walked into Elaine’s room, she looked up at me and said, “What’s up, Cricket (my nickname growing up)?”  I walked over to a chair and sat down waiting for her to say something about the way I looked.  After all, I was wearing makeup, a woman’s pullover shirt, a pair of “her” heels, jewelry, and earrings.  Instead she sat there looking at me, and asked again what was up as though I was not dressed the way I was.  I finally started spewing out everything.  And I do mean everything including that I was convinced I was gay, and that I had somewhat of a boyfriend whom I was seeing on a regular basis.  After about twenty to thirty minutes of non-stop confessions, I finally came to a stop.  Elaine sat looking at me for what seemed to be the longest few seconds I had ever experienced, then finally put her arms around me as tight as could be.  When she finally leaned back and came face to face with me, she said, “I know,” and “It’s okay.”  She shared that she had known for a long time, but would not bring any of it up until I stepped up and told her.  How fortunate I was to have her in my life.  She stood right beside me when I began telling my mother and my other sisters.

That was forty-two years ago, but Elaine and I still remain closer than my other sisters.  She lives in Seattle now which seems so far away.  We talk all the time, but just don’t see one another very much.  My other sisters live somewhere else as well so it seems like I am the only one still here.  I have always been a little more sensitive and sentimental than your average All-American boy next door, and today is no exception.  I feel the tears running down my cheeks whenever we come to the end of our conversations and say goodbye.  I miss being close to her, and not being able to get in the car and drive a mile or two to visit.  She has chosen a couple of professions with which not many people agree.  But I do because it is who she is.  I accept and respect her choices as she has so openly and lovingly accepted mine.  I think my sister knows how much I deeply love and admire her, but I want to tell her again anyway. My sister, I love you with all my heart, and I am truly grateful that you made your way into our lives, especially mine.  Thank you for just being you and letting me be me.




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  1. Profile photo of nancy
    nancy 2 weeks ago

    I wish all the sisters should be helpful to their crossdresser brothers

  2. Profile photo of Michelle Brown
    Michelle Brown 2 weeks ago

    I,too,have a special sister.We live in different states and after much internal debate lasting over a few years I finally told her that I was a crossdresser,Her answer to me was “If it makes you happy,go for it”.She has seen a few pictures of me fully dressed as Michelle and plans to visit when her business permits later this summer,maybe finally for some sister and sister time.

    • Profile photo of Jackie Wild Author
      Jackie Wild 2 weeks ago

      Michelle it’s so cool and a true blessing when we know we have that special bond and acceptance from other’s especially our family. My mother wasn’t that accepting at all, in fact she cried more than once always asking where she went wrong raising me and I would tell her she didn’t at all raise me to be a cross dresser or a drag queen or even being gay. I told her and other’s it’s just simply who I am and even if I didn’t want to be I was/am end of story. Thank you for leaving your comment. It’s comment like yours that inspire so many struggling with acceptance and fear of coming out. Your sister is awesome!

  3. Profile photo of VickieJ
    VickieJ 2 weeks ago

    That’s a beautiful and touching story Jackie. I have not been logging into this site much lately as I have been preparing my life for a full transition.

    Your touching story reminded me of why I love logging in.

    Thank you for sharing


    • Profile photo of Jackie Wild Author
      Jackie Wild 2 weeks ago

      Oh thank u Vickie. I wish you all the best travels in your journey. Lot’s of courage and belief in yourself to go all the way to transition. All the best to you and may the high heel God’s shine upon you. Please keep us informed of things go k.

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