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Smile With Confidence!

Lookee who stopped by.....

The Elusive Sherry Greer

I’m sitting on my couch after reading day 2 and the comments of Tina’s experience at the Italian restaurant. Looking at the pictures of her beautiful dress and the radiance of her smile, I can’t help but shed a tear of joy for her 🥲! Having the confidence to go out as we do is not something that happens overnight but a journey of self-assurance. I think of my ongoing journey and where I started, where I’m at presently, and where the future will take me. So many emotions, so many ups and downs, so many tears of self-doubt and so many tears of joy from experiences that I thought were unobtainable just a couple years ago. I have so many people to thank for their support and guidance and the true love for me as a person, at times it is overwhelming to think of how lucky I am for that friendship.

Being in the position that I am, that is, officially retired but then getting rehired to do a similar job has allowed me to have a bit of a different attitude towards being who I am and being seen by others. Please don’t think I’m more reckless now and don’t care about that because I do and it’s something I think about every time I go out. The difference is I am in control, if something would happen I can walk away from that position and be me because I’m “retired”. This has given me more confidence, I tend to wear my natural hair more as opposed to my wig. It is funny how the two sides of me have blended into one! An example of this is I happen to pull beside Kandi while driving in male mode, and she thought I was Sherry. Conversely, I was driving as Sherry and a coworker who works very closely with me pulled up beside me and thought I was my male self!

On January 14th I went out for dinner with Stephanie and Lori, two coworkers for dinner. On the 15th I went to lunch with Amanda and Jen, two more coworkers. Each time I think they were more nervous being seen with me then I was with them because of the negative possibilities. Later that day I went to a store to return an Amazon purchase and to a building supply store to purchase some supplies to fix a shelf for a friend. I walked into those stores with a smile of confidence! After I was done fixing the shelf my friend Laverne took me to dinner. Even when the hostess seated us and made a gender comment that would have, in the past, ruined my night, I had the confidence to correct her and politely tell her that she had it correct the first time when she addressed us as “ladies”. The attached pictures are of the two days.

I guess the moral of the story is allow yourself, and it’s hard, to become the person you deserve to be. Despite setbacks at times it’s worth seeing a smile like Tina displayed in her pictures❤️❤️❤️.

Stay beautiful-Sherry


15 Responses

  1. Sherry,
    This is a wonderful telling of where your journey is today. As you say, confidence is what makes this all happen and feel normal.

    You certainly “ROCK” those jeans and boots. I am so envious of your hair; long, wavy, feminine and encapsulating your big smile.

    Being out with friends is just a simple part of living. It normalizes our CD/TG life.

    I am so happy for you.


    1. Jocelyn,
      Thanks so much, it continues to be a journey, I love the ride so far! Thanks for the compliment ❤️


  2. Sherry,
    Being retired does open the door to have greater freedom to be you .
    You make a very valid point about spending time with GG friends or work colleagues , knowing you at some point as a man places doubts in their minds to how they will accept you as a woman especially when you meet in public places . I know the pressure it can create , you have to get the clothes right , consider how much makeup and then how do you behave with them . Do you remain the guy they knew or do you gently go down a more female route ? I admit we can’t hide the guy completely , from my own experience your initial look and behaviour will set the scene , in those few minutes they subconsciously decide MALE OR FEMALE , any male traits after that are usually overlooked .

    I go out regularly with my daughter and her mother in law , I take my mother to garden centres and buy her lunch , I could go on but the important point is they wouldn’t do it if they didn’t have confidence in you , you won’t embarrass them , but also importantly don’t intentionally out dress them . The one aspect that does take some getting use to is using the same toilets and changing rooms as them .

    1. Teresa,
      My co-workers obviously know my other side but when Sherry is out with them I am their girlfriend and nothing else. They totally except and welcome Sherry into their lives because many have said that Sherry is a nicer person!


      1. Sherry,
        It’s wonderful to receive that comment , I’ve also been told they prefer me as Teresa , they appreciate it makes us a happier person .

  3. Hi Sherry: First of all, I love your hair–I am a bit envious since I don’t have any. You look great in your casual outfit. Love the jeans and boots. As a fellow retiree, I do have more freedom to be Donna, however, since I am not out in my city (my choice) it’s not as often as I like. I like the idea of doing “normal” things when out–it’s not all dress shopping and having lunches or dinners. Although that’s fun too. Thanks for sharing your life with us.

    1. Donna,
      Thank you for the kind words, they are very much appreciated. I used to think I had to do something ultra feminine to feel that way but now the everyday look has just as much feminity ❤️.


  4. Sherry, I was privileged to have a sneak peek of this post, referring to my January outings. I am so happy to see your smile in all these pictures. Your natural hair is lovely (I have none), and I had to laugh at your stories of people mixing up your male side and Sherry.

    1. Tina,
      You did! You were my inspiration for this post. Both of my personalities have merged into one. Right now I am sitting at my desk at work with male but leaning towards androgynous clothing on, my hair curled and a subtle but full face of makeup!



    HAVE BEEN WATCHING_FOLLOWING YOU SINCE YOU FIRST LINKED UP WITH KANDI WAY BACK WHEN. YOU HAVE COME A LONG PAIN STAKING WAY BUT HAVE SUCCEEDED. MANY WOULD HAVE QUIT. You are now the perfect TOMBOY if that title is acceptable recalling that all the TOMGIRLs I have known were cute and Blossomed into a beautiful woman. Congratulations on your success and your persistence.

    Marie Anne

  6. Sherry,
    “Both of my personalities have merged into one. Right now I am sitting at my desk at work with male but leaning towards androgynous clothing on, my hair curled and a subtle but full face of makeup!”
    I love that. And I am jealous! I remember having hair down to my mid-back. Or even having hair at all. Distant memories.
    I’m sitting here in my home office with semi-androgynous female clothing on getting ready for my mani/pedi appointment. Then off to work afterwards. Your statement above reminded me to put a little mascara and eye shadow on before I leave – thanks.

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