Living a double life for 40 years wasn’t easy. I thought after all those years I was like Superman. Any chance I had, I was dressing like a female. To help you understand, I’ll start from the beginning when I was 13 years old, when I first started dressing.

I started exploring in my mother’s closet looking at all the hot and wonderful clothes she wore, from medium-length dresses and skirts to mini dresses and skirts. My mom was smoking hot in her younger days. Okay, she still is at her young age of 83. Although my mother had some awesome clothes, I really liked the style and look of my Aunt Harriet. I would take the clothes my mother had and styled them up to what I believed my aunt would wear. So, around the house whenever I had the chance I would dress up. After school (and most of all when school was out), I would dress all day long until I thought my mom would be coming home. She never knew when I called and asked her when she was leaving that that it gave me that much time to stay dressed. Even if I didn’t know when she was coming home, I had my male clothes ready to jump into like a fireman when I heard her coming in.

Later when I got older and started to shop at the store, I had hiding places in my house that no one could find. I would hide my women’s clothes in my bedroom in the drop ceiling, footlocker, and in even the trunk of my car. Sometimes, depending on the clothes, I could mix them in with my male clothes in the drawer or closet. I was good at hiding things.

When I would go somewhere in my car, I would change somewhere nearby the house, such as in the car at the park or the gas station. Then when I got near to where I was going, I would park somewhere and change back into my male clothes. I got so good at changing, I could from male to female in about ten minutes, makeup and all. I would always carry a jug of water to wipe off my makeup.

I believe the hardest thing for me to do when being out at a club was remembering which name I was at the time. When I had an email account, I had to remember in my writing who I was at the time and not to slip up, mostly when I was on my work email. There were many times that my mind was in the mode of Karen and I didn’t know why. Sometimes I wish I could come to work dressed as Karen and work all day that way. I even would imagine myself taking the metro to work and walking down the street as Karen. All these times in the past I wondered what it would be like to go to work as Karen, never knowing why I felt that way so deep down inside.

Years later I got married, and the hardest thing was for me to come to terms with living this way and being married to someone you loved and not hurting her. While I was married for 18 years, I knew it was wrong, but I didn’t understand it myself. After my divorce and I realized that I was transgender I tried to call my ex to say, “I’m sorry.” I tried multiple times to tell her I was sorry, but she never returned my calls. My stepkids knew I wanted to say those words, “I’m sorry,” but she still didn’t call, however I did apologize to the kids. Maybe one day she will see and read this article and know deep down inside of me, I am so sorry, and that I never meant to hurt her. Now, I can truly understand who I am, and that I am 200% happier than I have ever been.

My next article will be titled “Staying Safe as A Woman Now.” Visit my personal website at, or for comments write to me at Remember one thing … Shoot for the moon and even if you miss, you’ll be among the stars.

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Author Profile

Karen Kendra Holmes
Karen Kendra Holmes
Karen Kendra Holmes works for the Federal Government as a Safety Officer. Besides her full- time job with the Federal Government she is a part-time radio host on WPFW 89.3 FM on the “Inside Out LGBTQ Show” on WPFW 89.3 FM. She also writes a column for Baltimore OUTloud under the column called “Trans Lives”. Karen received the Engendered Spirit Award from Capital Pride on June 7, 2018. She also was a TEDx Speaker with TEDx Asbury Park, NJ on May 19, 2018. In April 2017 she received the “2017 Monica Roberts Advocacy Award”. She was selected in January 2017 by LGBTQ Nation as one of the “Top 50 Successful Transgender Americans You Need to Know”. In May of 2015, she was honored in a special edition among 41 other women from around the world in The Platform Magazine, for up and inspiring females who have made a difference with their platform and inspired others with their positive values towards others. In April 2014 she received the “Willis Greene Community Service Award” and the “Unsung Hero Award-Team” by the Corporation for National & Community Service. In October 2013 she received “Soldier of the Year”, out of the country, by the State Guard Association of the United States out of 24 states and 23 thousand soldiers. In December 2012 she received “NCO Soldier of the Year” by the Maryland State Guard Association and The Maryland Defense Force. She was selected in August 2012 by The International Women’s Leadership Association, "A Woman of Outstanding Leadership in the Business Owner Division".

With the Maryland Defense Force under the Maryland National Guards she was a Staff Sergeant with Force Protection, the Chaplain’s Unit as a Chaplain’s Assistance, Honor Guard, and MWR. She has been doing volunteer work with the American Red Cross for the National Capital Region since 2009 on the Disaster Action Team. For several years, she has been volunteering with Community Emergency Response Team (CERTs) in Prince George's County, MD, and also with the Medical Reserve Corps. She sits on the board for the Retired Senior Volunteer Program (RSVP) in Prince George's County, MD. Karen also use to sit on the board for DC Metro PFLAG working with the Transgender Community. She is now the chapter president of the Transgender Veterans Support Group (TVSG) for Maryland. Before Karen’s transitioned, she previously volunteered with the Maryland National Capital Park and Planning Commission Park Police Prince George's County Division for 7 years, 5 of them as their President, and received several awards for her service, such as two Commander’s Awards and two Volunteer of the Year Awards. In December 2005 she received the Governor’s Crime Prevention Award for her outstanding work and leadership with Park Police Volunteer Association. She has her own side business called SafetyFirst DMV and is certified as an instructor through the National Safety Council (NSC). Karen believes whole heartedly in the importance of and Giving Back to her Community.