About two months ago, I met someone (let’s just call him Chris for now) at a friend’s house.  I showed up in my daily apparel — makeup, jeans, shirt, heels, and a bag draped over my shoulder.  My gurlfriend introduced us and we began talking.  Chris asked if I dressed everyday like I was, and I said yes.  I will not even go outside to check the mail without makeup.  The question of how I deal with anyone who stares or whispers to the side about how I am obviously not a real girl or woman or how I am dressed.  My response was simple.  I do not even see them; I do not care how they look at or feel about it.  I got over that a long time ago — sometimes I just stare back and they look away.

“See I am a cross dresser and gay,” Chris told me, “and wish I had your courage.”  He went on to explain that he was married with a daughter, and was scared to death about how they would feel regarding this.  Yes, he was miserable and full of fear, I could tell.  He was afraid of losing them, his family and current friends, which is normal and alarming for anyone.  I explained that all of us know from where he was coming.  It is a scary thing, no doubt, for anyone who has feelings.  Chris appeared to relax – just knowing that you are not alone has the unimaginable ability to calm.

The three of us kept talking and sharing for awhile.  My gurlfriend suggested that we move the conversation elsewhere and said let’s go get a latte.  Of course, I was all for it.  To paint a clear picture, you need to know that my gurlfriend, too, dresses in what society deems women’s apparel daily.  In fact, she and I are much alike; we each do not own one thread of men’s clothing, if we wanted to wear any.  We stood to leave and Chris spoke up.  He said he better not join us, and he had some things to do.  We both said “Come on and get a latte with us.  It won’t be that long.”  Chris was clearly apprehensive and torn between feelings.  At that point, my gurlfriend asked if he was scared or embarrassed of being seen with us.  Chris said nothing personal, but yes, he did have concerns.  I explained it is just a small coffee shop and no one will know you, nor you them.  Nonetheless, Chris chose to not go with us.

Later that evening, my gurlfriend called to ask if it was okay to give Chris my phone number.  He wanted to talk to me.  I told her absolutely.  Five minutes later, Chris called and began telling me how much he admired my courage and that he would like to talk with me some more.  I explained that it was no problem and he asked when was a good time for me.  “Tonight is good, or if you can’t do tonight, let’s plan it for tomorrow.”  Chris agreed to come over tomorrow morning.

When we sat down to talk, I noticed Chris’ eyes filling up with tears.  He was quick to apologize, but I said it was no problem, explaining that crying can do miracles for us.  We began where we had left off the day before.  As I sat and listened, I could feel my own eyes watering up.  I could feel the fear, the hurt and even the anger in every word he said.  After listening for some time, I asked Chris what exactly is it that he want in his life?  He wanted to be free of all the lies, the deceit, and the pain in his heart.  Chris was in pain every time he dressed in his wife’s clothes and makeup, and especially every time he was unfaithful to her.  How could I help other than to share more of my own experiences, I asked?  Chris wanted to come out, but needed my and others’ support, and to hear that everything would be okay.  I assured him that he had my support and blessing and I was willing to help in anyway that I could.  We talked for several hours.  Unsurprisingly, Chris had many questions and concerns – some may have been trivial or unrealistic, but most were to be expected.  I did my best to address each one.  Though his journey was only beginning, Chris left my home with a greater understanding of his situation and generally feeling better.

That was two months ago and I have not heard from Chris in that time.  Recently, he called me again.  He just could not handle it anymore; he was ready.

Part 2 is forthcoming.  Be sure to check back in the days to come.

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  1. Melinda 3 months ago

    Wow that was very nice of you and im the same just told my cousin how i fill as well but still iside personal but thank you for the advise

  2. Rachel Rose 3 months ago

    I really liked this story and want to hear part two!

    • Author
      Jackie Wild 3 months ago

      Hi Rachel long time. Part two is here and I believe there will be a part three. I am being encouraged to to keep everyone here posted so what better way is there. Thank you for liking her story. Stay strong girl and hope to talk with u again soon. I haven’t forgotten that you were one of the first that welcomed me to CDH with such open arms and we talked like we had known one another for years and for that I am truly honored to have u as a friend.

  3. ELAINEA 3 months ago

    I would love to have a girlfriend like you JACKIE. I WOULD LIKE TO HAVE YOU TEACH ME HOW TO FIND MY FEMALE SIDE

    • Author
      Jackie Wild 3 months ago

      Elainea I would be more than willing to talk to you anytime. PM me whenever and we will talk okay hun. I don’t know what I could teach you that you don’t already know but we will come up with something haha & giggles. Be strong for what you believe in and never let ’em see you sweat!

  4. Nina Je t'aime 3 months ago

    Hi Jackie, I enjoyed reading your story & would like to ask u on your first time sex encounter dressed. I am coming out & curious on how 2 enjoy my first time encounter 2 B more specific when being entered. & being relaxed.

  5. shaun 4 months ago

    Would really love a nice girl to crossdress me in the durban area, would perhaps have any leads?

  6. Meili 5 months ago

    Interesting, guys attracted to us, have the very same fears we have at the opposite spectrum. Because of the stigmatized society those men are often the one who may turn on us in violence. I am not speaking form experiences, just observations of all the reading and research it have done. I have been who I am from 4 or 5, and never connected with men or women but was more attractived to women being married twice. Being married to my second wife, the love of my life is not about male or female, lesbian or gay, it is about who I love and thus my wife is my sexual orientation. Know you and you will connect with the one who will respect and accept you for you.

    Meili

    • Author
      Jackie Wild 4 months ago

      Thanks Melli, your right on and I appreciate your input. It’s not about being gay, straight or bi but how one treats whatever sexual orientation they are. Too many people take for granted.

  7. Stephanie Stanek 5 months ago

    What a great story Jackie and love how inspirational, helpful and truly extending an olive branch to Chris. You were unwavering with your support, understanding and confidence you displayed. I applaud you for being true to yourself as Jackie and how comfortable you are as a woman and it translated to Chris reaching out to you. I admire you for being en femme and have always enjoyed your pics. I hope that someday I can do the same for someone and am always encouraging some of the women at CDH to stay the course but it can sometimes present a challenge if someone is in a relationship. I am always open to meeting fellow CDH members and discuss where their path is heading but unfortunately, I have only been able to meet one member and we had a wonderful time!

    I look foward to hearing about your next chapter with Chris.

    • Author
      Jackie Wild 5 months ago

      Thank you Stephanie it’s been a real tough time for her but she knows that she is doing what she is meant to do regardless. I wholeheartedly believe we are who we are and were born this way. As I have told her and myself for that matter I don’t believe we just one day woke up and gee today I think I will use my sister’s makeup, clothes and heels and see how the world treats me. I believe every cross dresser, drag queen, transgender, transvestite, she male and the likes are just wired this way and we have a unique way of knowing we are to do what we do. Not every boy in America or anywhere else puts on makeup, a dress and heels and becomes her or becomes a member of a society like CDH. I truly define us as unique. Thank you for leaving the perfect comment. With permission I will keep every one informed of her progress.

  8. skippy1965(Cynthia) 5 months ago

    Jackie,
    What an inspiring story of how the simple act of friendship can make a huge difference in someone’s life. I’m this case, you are fortunate enough to see and be aware of the person you are helping. But you also never know how many other lives you touch just by loving your life on your own terms and providing a loving example of what self -actuaized person is and the power it provides. I am striving myself to figure out who I truly am and hope that it will be done rather than later before I too feel free to show all of myself to the world on a more regular basis.

    Thanks again for sharing and I can’t wait to read part two!

    Cyn

    • Author
      Jackie Wild 5 months ago

      Thank you Cynthia I appreciate the kind words. I think the Creator has a plan for each of us and I think we are to follow our instincts and be who we were born to be. Too many suffer trying to keep another image than who they really are. Fear is a thing none of us should face when we need to be ourselves to be happy. Some live lives that they believe everyone they know especially family want for them to live and they are miserable just like my friend this article was wrote for. Life is short and we are only here for a minute, we need to be ourselves now and not tomorrow, because as we know tomorrow never comes.

    • Melinda 3 months ago

      Yup your right and im first time to scare but im just starting to open up little by little love to crossdress and love female cloths i keep in doors not out yet but slowly i will thank you for the support

  9. Hi Jackie! Thank you for sharing your concern and your friends anquish. I am not one to cry………that
    trait was driven out of me by what I have seen and experienced during Vietnam, and things I have seen in my travels. “Master…..why is there such ugliness in the word??? So that we may know beauty when we see it grasshopper”. Your story is beautiful as well as your actions. I did not cry at my daughters funeral but your story brought tears to my eyes for the 1st time in over 40 years.

    “Chris” needs friends badly. You and yours are there for her. She will be OK. A Lot of times we need friends to talk to, to help us with our sorrows and to share the path thru the storm……..a wingman/woman so to speak, to have our back. I am here for support and advice and encouragement. I am Wolf. I watch my pack and lend a paw to help, to defend, to console and to heal when necessary. PLEASE, let me know what is needed to help. “Chris” can contact me anytime, as can you, for an ear to listen and perhaps assist to help her. Ask and Ye shall receive. I shall send the Spirit of Strength to help you along. “Chris”………step back, take a couple of deep breaths and to your demons and Negative Neds….say….”It don’t mean nothin”, “It don’t mean nothin” as a mantra.
    Do keep in touch, all the best to you and “Chris”. I am watching and ready to help. May the Force be with You both. PS. If you like….I have a necklace (Talisman) of a sacred stone with a howling wolf upon it to send to you for Chris to wear as a constant reminder that she is not alone………”The Strength of the Pack is always with her”. Lady Veronica

  10. Manager Codille 5 months ago

    So proud of my girl. This is what we are about Jackie and this is what I have always seen in your heart. Can’t wait to read part two!

    • Author
      Jackie Wild 5 months ago

      Thank you Mother Codille. Coming from you that means the world to me. Good thing I don’t have my eye’s done yet for the day because my liner and mascara would have had to been done over, it short you made my eye’s water. I am going to share her progress with CDH (with her permission of course). She remains to be a little down emotionally and mentally but coming along very fine. K well stay tuned lady cuz it can only get better as progress is made. Luv ya, Jackie (wild child)….

    • Author
      Jackie Wild 5 months ago

      Lady Veronica, such passion you have. Ironic thing is is that I myself love wolves and the kindred spirit they possess. Along with courage, stamina, bravery and intelligence they, like us are the victims of a cruel society that hunts them down for they’re own selfish reasons. I think it’s like that with who we are. People stare, people whisper, people judge who I am and the fact is is that most of them have insecurities within themselves and need to point me out to feel better themselves for insane reasons of they’re own. Chris has chosen to be herself at all cost which is more than I can say about millions of others in this world. Yes she is heart broken for the space it has cost her between her family but we all know that gets better over time. It is time for her true journey to have begun and be who she is meant to be. I went through some hell myself when I was younger with my family but time and perseverance ruled out and took care of it. Thank you for your kind reply and just know this; You have a kind spirit and with that comes kind feelings and words of inspiration to others. Thank you for your service by the way, it’s courage and bravery like you possess that keeps America what she is.

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