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.

Exceptional Voice

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.

More Articles by The Author

The following two tabs change content below.


Jewelry Artisan, cocktail waitress, part time escort. at Emerald Club, Shuckeys Club
Very simple yet at times complicated but I always prevail. I have been out since the young young age of 17, both CD, Drag and sexual orientation. My mother kind of figured out allot of it before I came clean one morning. I love drag, I don't really perform like so many queens do, I guess unless you piss me off I'm pretty silent. Been in only two serious relationships and loved them both with all my heart (this is the area I mentioned in the beginning where it get's complicated). I am a strong supporter of LGBTQ and gay rights. Why can't we all just get through this world together? Life is short so I try to live each day like there will be no tomorrow, because there may not. I am so easy to get along with it's crazy. However, there are some people who bring out the worst in me. When that happens go the other way!

Latest posts by Jackie (see all)

0 0 vote
Article Rating
Notify of
Inline Feedbacks
View all comments
Manager Codille
Managing Ambassador
Manager Codille (@managercodille)
3 years 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!

Dame Veronica Graunwolf
Active Member
3 years ago

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… Read more »

skippy1965 Cynthia
Trusted Member
skippy1965 Cynthia (@skippy1965)
3 years 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… Read more »

3 years 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

Stephanie Stanek
3 years 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… Read more »

Meili (@meili)
3 years 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… Read more »

3 years ago

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

Nina Je t'aime
3 years 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.

3 years 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

Rachel Rose
3 years ago

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

3 years 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

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account