Stories of Transitioning Journeys

I never knew how my life would be as a woman, but it has its ups and downs. You are wondering what I am talking about, well let me take you back in time. To understand me completely I need to return to the age of 13. As a young teen boy, I started dressing up in girls' clothes. It was awesome and I got dressed up when ever I could. It started off putting my mom's dresses and shoes on. I would walk around the house until my parents came home and I was so happy. I am not sure how to measure being happy back then, comparing to my life today, but I am 200% happier than I have ever been. Keep one thing in mind when you read this article, I felt as a male before June 2010 I was happy. On October 1, 2010, my life changed forever for me and the journey began.

So, that weekend before October 1, 2010, I got my nails done and brought a new wig. The night before my big day I picked out my outfit to wear. Not to draw to much attention to myself I decided to wear pants, a nice top and one-inch black heels. That morning I got up extra early to get dress, do my make-up and hair. The most important thing I wanted to do was put my make-up on to be nice and subtle, not to heavy. My first week back I drove in because my mind was not ready for Metro transportation. The following week I stated to ride the metro train and making sure I sat properly on the train and caring for my purse in a way that I was not a target to be taken. The one main thing is to remember to take my purse and not to lay it down on the floor or seat. Knowing how to walk over the street crakes and always being aware of my surroundings. Trying to remember to check my car before getting in for safety reason was a must.

I have had some challenges in my life since my transition. For starters, the zipper on pants are on the other side, buttons on women's blouses are on the other side. What use to take me 5 minutes to wash my hair, now takes me 45 minutes to an hour to wash and dry. If I go to the hairdresser, I am there four to five hours. If I go to a sporting, concert or movie event the lady's bathroom line is out the door and down the hall. The one main thing that I never thought about is the cattiness among women on your looks and what you may wear. My first 2 weeks back to work I heard from my old boss is that a couple of the women said that my outfit look like I was going to a night club, which I never wore anything like that. I did not even wear a dress until my second month, it was always pants. A good girlfriend of mine at work said, "Do not worry, "Welcome to the Catty World". I said to myself, "This is what I have to deal with now"! Learning now medical terms and questions I am asked as a woman. Stopping them after I have said no to i.e., being pregnant, had any children or when was my last period. The one thing I hate is my annual mammogram and having my boobs crushed. I had to learn which was genuinely nice, men opening doors for me, letting me go first through the door, and giving up their seat on Metro train. What I have not like is men thinking they know better than women and out speaking to us in meetings. When I was an active soldier as a Corporal, a Colonel tried to oversee what I was doing, but another Colonel advised him right away to say, "Corporal Holmes got this, and things are going great". Later that day the General gave me his Challenge Coin.

After all that I have gone through in the past 10 years, I would not change a thing and I Love My Life as A Woman. You can find my TEDx or TED Talk when you Google my name. If you need to talk about anything, email me at Until next time Shoot for the Moon & Even if You Miss, You'll Be Among The STARS!

Taking you back prior to my transition in 2010, my love life was average. I did good at dating when I was not in a relationship. I was married twice before and engaged to be married again for the third time. My first marriage only lasted six months, because she said she really was not ready for marriage. The second lasted before it was all over 19 years. I felt like it was a good marriage, but with issues here and there. During my 19 years of marriage I was still crossdressing all through that time, denying to my wife I was not for all those years. She never found my clothes except for when I left a pair of panties a couple of times in the washing machine or dryer. No matter of my crossdressing I still loved my wife and her children from her previous marriage. Later I met a beautiful woman again who live in Seattle, Washington online, which later I propose to her. All during that time with her I was still crossdressing. Whenever I was going to Seattle or she was flying in I would grow my mustache back. After our first year she called off the engagement, which I had crashed and burned over the breakup. A month later she wanted to get back together, which I was still crossdressing, and still did not know I was. A year later she called off the engagement again, but this time for good. After the second time she called it off, I knew it was meant to be. At that time, I said to myself I was going to crossdress all the time, still not knowing I was Transgender. In June of 2010 at a conference in Philadelphia I realized who I really was, I was Transgender. I went back home ready to transition, to live full time as a woman. On October 1, 2010, I transition living as aa woman 24/7, being 150% happier than I had ever been. After my transition I decided not to date anyone for five to six years, because I knew I needed to concentrate on myself and my new life as a woman. During those five years I had men and women interested in me, but I still did not want to be in a relationship yet. After my first five years, I started thinking I was ready to start dating and wanted someone to be a part of my life. Well later I joined a dating site called Black People Meet, then Plenty of Fish, then Match.Com. None of them worked out for me on response, which was a bummer. I have to say on Black People Meet, I wanted to test the water to see how responses I would get with men. Oh, I forgot to say I am still interested in women, but I wanted to see how men would react. In three weeks, I had around 150 men respond. I narrowed it down to 100 men. Then I told those men I was Transgender, and 75 men told me they did not care. I never followed up going out with any of them. I later dropped off the internet and thought I would try the old fashion way at the LGBTQ bars or clubs. I came close a couple of times meeting someone, but they fell through. So, over the next few years, I have been looking, but no one has had interesting in me. In the last couple of days, I decided to get back on Black People Meet again to see if I will have better luck this time. So far again there are no catches. Maybe I should just give up on love or just give it some more time. You can find me at or visit my personal website at In my next article I'll talk about "My TEDx Talk Experience". Until then Shoot for the Moon and even if You Miss, You'll Be Among the STARS!
It started two weeks before "D Day", when I told my family I was going to transition on October 1, 2010, as a woman. I had no idea the response I was going to get from them, with their full support. I told my mother that my name would be Karen. Something she never told me before, that when she was pregnant with me if I were a girl, she would have name me Karen. She never told me that and I totally lost it with tears. What was good my family was accepting me for who I was deep inside. Within the two weeks my mom told my aunts, uncles, and cousins that I would be transitioning full time as a woman. What really surprised me is that all of them understood it was a lifesaving moment, except for a couple of uncles. I really did not understand how much it bothered me losing my favorite uncles. Leading up to my first day as a woman, my mother studied and learned what my transition was all about. She read every information I gave her, getting a bird's eye view what my life would be all about in the future. I even gave her a book to read and that I would give her another one afterwards. When she finished the first book, she loaned it to a neighbor friend. I asked her why she loan it out because I had not read it yet. Her response was, "I thought you had read it already because everything you are doing was inside the book". When ever my brother would come over for a visit and he heard my mother use the wrong gender, he would nicely slap her hand as a reminder to call me with the correct gender. Later I had to go easy on my mom because of her age, which was hard for me to understand. My dad and sister were good at supporting me in every way. Now my mom has not only been supportive of me, but she has been immensely proud of me going to a lot of my talking events, like my TEDx Talk in Ashbury Park and awards. Telling me how much she loves me, sending me birthday and holiday cards that say, my daughter on them. My brother would call me and hang out with me when he comes to visit. When we talked on the phone, he would tell me afterwards, saying, "I love you" each time. He also gives me cards that say to my sister on them. My sister is such a wonderful sweetheart towards me and the love between us is great. Sometimes we would hang out at home, going shopping, or going to get something to eat. With my dad, he calls me often to see how things are going with me and what I have been up too. Due to his age I go up to see him when I can, but he understands how busy I have become. No matter how busy I am when we talk on the phone, he always tells me, "I love you". His cards to me also have to my daughter on them. All my cousin loves me to death for who I am and the things I do to help the transgender community. We hang out, go with me to dinner, clubs, movies, picnics, and a lot more. Their support and love have been awesome and so real. All my aunts love me and accept me for who I am, except for one due to how her husband, my uncle, being Transgender. My uncle has written me off, not speaking to me and talking to my cousins to turn their backs on me, which none of them have. My mother and cousins do know how I feel about my uncle now, even after I try to build the bridge between him and I. For what he has done to me trying to turn my cousins against me, that bridge now has been burned. My family is awesome. You can find me at or visit my personal website at In my next article I'll talk about "My Keystone Experience". Until then Shoot for the Moon and even if You Miss, You'll Be Among the STARS!
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.
When I transition 10 years ago, I knew I might lose a couple of friends, but never the ones that were so close and family members to me in my life. This article will be among the ones that will be the hardest ones to write about, because I have lost a couple of wonderful family members and friends. The hardest thing is to have friendship that went to family, but then later lose them in your life. To them and I somewhat understand they have told me it was like I had died, and they lost a good friend. The one thing I tell them all you did not lose me who died, you still have me, just the better part of me who wanted to live. The hardest thing for me and other Transgender people is to be ourselves and to live the life we were meant to be and to be happy. But because the way society treats us, we lose our spouse or partner, family, home, friends, and job and commit suicide. To start things off after my mom told my family, all my aunts were ok with my transition, but a couple of uncles on my mom side of the family did not go so well. Now one out of the three is ok with me and another still has not and does not even look at me as part of the family. I was having a hard time with it when we were close before, but now I do not care anymore. The hardest issue I have with a family member treating me this way is that I have not brought any shame to the family in anyway. Then there are my friends whom I worked with, played softball with, and volunteered with. One of my friends who was like a brother to me whom I worked with and being around his family for years are not that close now. When I told him over the phone, I was Transgender and I was going to transition he said, “I’ll be right over”, and hung up. When he got there and I open the door the first thing out of his mouth was, “Are You “F”ing Crazy”. I will never forget those words from him. I tried to explain how and why I was going to transition. He was honest with me that he did not think things would be same between us anymore. It did change right away, and it hurt. Then there was another friend whom I played softball with from church. I played Short Stop and he was my 2nd Baseman, and we were awesome together up the middle. Not much got passed us and turning double plays were out of site. We were two peas in a pot sticking together on the field and in church. He has not returned my phone call yet in the 10 years after my transition. Finally, was a dear friend who I volunteered with the Park Police Volunteer Association (PPVA). Every two weeks on my Friday off we would meet up for lunch and just go over ideas for PPVA and where we wanted it to go. He would email me after my transition every so often to see how I was doing and the struggles he was going through losing a good friend in Tony and getting use to my transition. In his emails he would apologize that he felt he was not much of a supportive friend, but I told him that keeping in touch, and I understood. Finally, 4 ½ years later I was going to Dallas, TX to speak and I was looking for donations to go. We finally met up for lunch and it was great and later he told me how easy I made him feel meeting for the first time since my transition. I did not ask him, but he wanted to donate money for my trip. Things got so much better between us that he was even willing to take me for my Surgical Reconstruction Surgery (SRS) back on April 8, 2016, and yes, my five-year anniversary is coming up. Now every so often get together for Chinese food and watch a movie. Earlier I said since my transition, has never brought shame to my family and friends. I have done a TEDx Talk which is now on the main TED website. I speak around the country as a leader and advocate for the Transgender community. Provide Transgender training to the police and fire departments and the military. Meeting with politicians and speak with them on Transgender issues. Most of all doing TV, radio, podcast interviews and most of hosting a radio show and writing these articles. Keep one thing in mind as I close is when we transition our family and friends transition too. They have this sense of lost in their lives. But for you, understand this and that when we transition, we are doing it so we can live. You can find my TEDx or TED Talk “40 Years and Wandering No More”, when you Google my name. If you need to talk about anything, please email me at or visit my personal website at Until next time Shoot for the Moon and Even if You Miss, You’ll Be Among the STARS!
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