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Sherry’s Tipping Point

A great post by Sherry from the old site.

By Sherry Greer

This is a subject I have touched on before. The question… When was enough, enough and I finally ventured out as Sherry? As this whole gender world of exploration goes I don’t think I’m much different than most others. This all started at a very early age trying on my mom’s clothes, experimenting with makeup, wanting to look pretty but acting manly so people wouldn’t know. As I progressed through middle and high school I tried to experiment while home alone but sports took up most of my time.

When I got to college I really concentrated on school and continued to run track and competed in the Decathlon like Bruce Jenner! I was in great shape and even ran 3 miles in 16 minutes and 24 seconds. My life was full of activity for which left little time for Sherry. After graduation I married my high school sweetheart whom I am still married to (30+ years!). I still tried to dress when I could but it was still very limited. We bought a house which needed some fixing up, that kept me busy. My wife got pregnant, that definitely kept me busy. I did tell my wife about Sherry a few months after she got pregnant and even went to a gender specialist to talk about my situation. He told me “if it feels good than do it”, it didn’t feel good so I stopped doing it. My son was in sports and I helped coach on many of his teams, that kept me busy.

Fast forward about 20 years. I did still experiment from time to time but definitely when there was no chance of someone finding out. I was very much in the closet. When I turned about 48 my son was on his own and I had more time to myself. Of course those feelings came rushing back and Sherry had to get out. It took me two years to actually walk out the door. I was home on vacation and finally got the nerve to get ready and visit a beauty supply store about 30 minutes away. I cherished my time getting ready and still do. I love seeing myself in the mirror transform into a princess, it NEVER gets old!

Even though I finally ventured out this was not my tipping point. I was still very secretive and guarded. Kandi has expressed that it is extremely rare for her to see someone she knows when out but my job is very public and I literally saw someone I knew 3 out of the first 5 times I went out! My actual tipping point is twofold. The first part was when my son came to the house unexpectedly and saw me dressed. I will never forget the feeling of complete panic and how I felt my life would never be the same. I was definitely right. My relationship with my son was awkward at first but has gotten better. That event caused me to have conversations with my wife (some good, some really bad). This time was extremely trying for me and I got to the point where I was thinking about ways to not be here anymore. I am amazed on how my wife has accepted/ tolerated Sherry.

The second part came when I was working late and I was alone with a co-worker. I remember staring at my computer and just started to shake and cry. She came to me and asked what was wrong but I couldn’t speak because I was trembling too much. All I could do was get my phone out and show her a picture of Sherry. She assured me everything would be okay and she would help me. We talked a lot during the next few days and she helped me find a therapist. She has been an amazing friend. That day was when I realized that I had to live for me because the alternative was not an option. That was the day Sherry truly came out and I could look in the mirror and be happy with the reflection. I continue to evolve and get comfortable with who I am and where Sherry wants to go. I know I have developed a good support network both in person and online…thank you ladies for that!

As always…

Stay beautiful-Sherry


6 Responses

  1. This was a wonderful post and so well encapsulates the struggles that many of us face just to be ourselves. The secrecy and the constraints it places on us can be crippling but accounts like this just prove that compassion & support can come when it’s needed most.

    I love the outfit too!

    1. Amanda,
      Thanks so much for the comment! Life is hard but with love we can overcome anything ❤️❤️❤️
      Stay beautiful-Sherry

  2. Loved reading your experience. We have all been down some or all of that path. You’re beautiful, so glad you are finding peace.

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