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.
I too had an older sister who caught me wearing her clothes. She was totally cool and allowed me to wear whatever I wanted as long as I washed it afterwards. After I left home, I would often go out with her and her friends dressed as Gina. In fact she and her roommate enjoyed doing my makeup and picking out my outfits. She was even pretty cool with me when I briefly dated one of her male friends, only admonishing me to be smart and safe. She even caught me “in the act" with one of her male friends… Read more »
So it sounds like you were blessed as well, awesome Gina. As for the part about her male friend my sister found out I had been with one of her friends friends and freaked out, not on me so much but him instead haha. I’m spoiled like that.
That is such a beautiful story and a dream come true for any of us as we blossom and look for a supportive arm.
I finally have two like sisters whom support me and always have an open ear for the days that i need to talk.
God bless you Elaine.
Yvonne thank u, means allot to me.
Great story of support and inspiration. I am out to my 3 sisters all younger than me. However it is the youngest by 18 years who really is supportive. I have been dressed and out shopping with her, suppers in restraunts and she is open to discuss all with me. I am out to my wife and my two children and only daughter-in-law. They are having problems with acceptance and understanding and it has now taken 10 years to get to my wife to accept the underdressing and daily wearing of androgynous clothing and silk PJ’s to bed. I have… Read more »
One day at a time, one foot in front of the other. You are already a courageous person. Many wish they held your courage and devotion. How awesome that you have so much support. I wish you nourishment and prosperity in your endeavor.
VERY INSPIRING TO READ THIS ARTICLE AND FOR MYSELF I DO CROSSDRESS AND WEAR A BRA AND AMUSE IN THE MIRROR I ALWAYS KEPT IT SECRET THAT I WAER THE INNER GARMENTS AND MY DREAM IS TO WEAR BANGLES, ANKLETS AND MINI SKIRTS WITH TIGHT UPPER JACKET TO BE MORE OF A WOMAN SHAPING MY EYEBROWS ETC.
Hi Jackie, I really love your story. If this were made into a film, it would be a major chick flick (which I just love by the way). Your writing is full of emotion and passion. Thank You so much for sharing. I wish I had a sister like Elaine. Lucky Gurl!!!!
Hugs, Krista
Thank you Krista that was so nice for you to say. I wonder who they would pick to play the parts, Dolly Parton and Alexis Arquette?
Very beautiful story, beautifully told. Those of us that have people in our lives who support us are very lucky.
Great piece hon.
April
Thank you so much for the kind words.
Love this article because I also had a sister who is amazing. When I was about 3 or 4 and she was 7 or 8 she started dressing me up in her old princess costumes for her “tea parties" which was her, myself, and a number of select stuffed animals, lol. I can still remember how the flowing dresses and skirts felt on me as I twirled around. Eventually my dad made her stop and I didn’t know why. Many years later she was the only one who ever caught me cross dressing. I was 13 and she was 17.… Read more »
Thank you for your awesome comment and sharing this adventure with your sister and wife. It is an adventurous journey and for some lived by everyday. Your supports speaks volumes, I truly wish everyone had the same support as you and I. I think the world would be a better place if everyone was allowed to be who they really and truly are with no BS, intolerance, judgements and so on! I loved your little short but to the point you shared, thank you Bridget.
Jackie, thank you for posting your story. I loved reading it and made me think of my teenage years and how alone I felt. I was the oldest of 3 children and we lived in a very small apartment. I remember trying on my mother’s clothes and using her makeup on the rare times I was home alone. Reading your story made me wonder if I had been the youngest and I tried on my sisters clothes.
Thank you again for sharing your story.
Yours Terri
Glad you enjoyed it Terrim, it brought back many wonderful memories writing it. Take care hun.
Thank you Lissa, I believe you could be right hun.
Jackie this brings my emotions out so much and i wanted to cry just reading this article. This was so touching and loving?
Nikki
I’m glad you liked it Nikki, I wrote from the heart but was only able to tell some because I didn’t want the article to be long and drawn out. My sister is amazing and she has been a loyal loyal supporter and best friend. Thank you for sharing with us/me. Take care hun, Jackie.