From a miserable life to a much happier life

I came from a miserable life to a much happier life. I remember at the age of 8 feeling something wasn’t right with me, and I didn’t know what it was. In my teen years, I finally realized I was born as the wrong gender. I couldn’t come as I felt I wasn’t ready to do the next step. My parents saw changes in me; questioned me what was wrong. I denied it and told them nothing was wrong. Mom knew I was keeping a secret.

I remember going to family events, my mom and younger sister walking out wearing dresses and heels. I wanted to be like them instead of wearing a boy’s suit and tie. At 17, I would go through my mom’s closet and try on her dresses, skirts, nylons, tops, and heels. I loved it. I didn’t get caught, and luckily I put them back in place. I even tried on in a few of my sister’s dresses with the same results. I did shake off the feelings, and I thought they wouldn’t come back.

During my college years, I went out crossdressing sometimes; my family didn’t know I did this. It hurt the relationships with ex-girlfriends. I didn’t want to say it at, got all angry about it. I did feel guilty, and I knew I’d hurt them by not telling the truth.


My first pro job was as a math and algebra teacher at a middle school. My co-workers were concerned about me, asking what was bothering me, and I told them nothing. I did crossdress; I went out at night and was never caught. I hated my life as a guy. Finally in November of 2017, I knew I had to come out. I had hurdles in my life to get through. One of them was coming out to my wife, and I didn’t know how she would react. She saw I was hurting inside somehow, and she cared about me a lot.

Finally on January 4th, 2019 I came out to her. I shared my feelings about being born the wrong gender; how I’d felt all my life and tearing up. We hugged, and she told me that she was going to stay with me no matter what happened. I then prepared to come out to my family. Finally, I was ready. On January 5th, 2019 my dad, older brother, and sister took it well. My mom, she took it hard at first. She thought it was completely her fault and began to cry. I gave her time and told her it wasn’t her fault and comforted her.

At work, I wrote a coming out letter. I was going to starting working as a woman. The changes took time. My co-workers and boss could see that I was much happier. The students had mixed feelings, some at first missed my old self, but I taught them that you need to live your life the way you want. They adjusted very well and learned about what it is to be transgendered. The first time walking into work as Debra, I wore a dark navy dress with 3 inch heels. It felt great knowing that I was living as my true self.

The next step was to see a therapist. My wife was there with me as I was diagnosed with gender dysphoria. We worked things out as we tried to figure me out. She saw how much I loved shoes and shopping for clothing. My therapist, she sees that I am doing well, and my progress is going great. I decided not to transition by going on the HRT. I felt it would be a huge regret. In June, I had my first surgery, which was the breast augmentation. I love the results, (a 34D.) Thus far, my family has been great about the changes.

I did tell my mom that I’d tried on her dresses, skirts, tops, and nylons when I was 17. She took it well and said that she’d never noticed anything out of place. My sister did too after I told her I tried on a couple of her dresses. They call me, Debra now, including using she and her around me. I don’t miss my old life since coming out. That old life is dead to me. I hated my old life and have future plans to have the FFS and trachea shave in June of 2020. My voice, it is slowly becoming more feminine, and I’m seeing a specialist to help me. My friends say I am a much better person; they also comment that I have my life and confidence back. They were relieved and proud of me for finally coming out.

En Femme Style

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    3 years ago

    Wonderful story Debra! Thank you for sharing!

    Dee Pelau
    Dee Pelau(@deepelau)
    3 years ago

    Congratulations Debra! It’s so wonderful to hear that you are living as you were meant to. XO

    Darla Darling
    Darla Darling(@darlad)
    4 years ago

    Hi Debra. Nice to hear your story. I am 63 with a loving wife. I have gender dysphoria. I have been cross dressing for more than 50 years. I have raised my family and love my grandchildren. I think I am very lucky but can’t help but wonder what else is possible.

    Angela Booth
    Angela Booth(@ab123)
    4 years ago

    All the fears and trepidation’s of your secret. You knew the truth and when you decided to let yourself out you realised that you were surrounded by people that love and respect you for who you are.
    I wonder if you thought that you should have done it sooner. Some of us think like that. The answer is simple – you did it at the right time even though it was a long and painful wait.
    Enjoy the rest of your life Debra

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