My First Time Out

I am excited to share the story of my first time out in public en femme. I hope that you are encouraged by my story

I am 34, married, father of two, and identify as a crossdresser. I have an interest in the whole gender-spectrum of expression. I’m currently growing my beard back, and glad to do so, as I hate shaving my face. My wife loves me dearly, and though she does not understand nor is comfortable witnessing or participating in my crossdressing, she is however, remarkably supportive. It’s taken some work, y’all. I have never resented her stand or pressured her for more than she is willing to accept. I think of our marriage as a bit of a bait-and-switch, since she had no idea what she was getting into when she married a closeted crossdresser. Seven years into our marriage, it has begun working itself out in some complicated ways.

At the end of last year, we made some concrete progress on my desires. She gave her blessing to me to explore what all of this means, in my head and through experience. As a goal during this past year, I wanted to get out in public at least once. The fact that it took me until November is a testament of how plans can differ from realities when difficult developments have to be circumvented. I’m sure other married CD’s will understand.

Unleash Your Inner Woman

My progress was not linear, and we had some setbacks. My wife and I have learned to over-communicate in order to prevent any misunderstandings. Suffice it to say, my feminine wardrobe was tucked away in the basement a couple times during the year. In the past few months, a couple of very important developments happened that allowed the timing to be right. First; we do communicate—all the time. Every other day or so I ask, “So, how’s it going being married to a crossdresser?”Interestingly, the more I ask, the more nonplussed she is. Secondly; I got my ears pierced back in June on a date with my wife at the same time she had her nose pierced. We called it our “mid-life crisis” date, even though we’re only in our thirties. Thirdly; my hair had reached a point that made it more possible for me to pass. And lastly, I’ve lost 15 lbs over the last few months, which helped to bring it all together.

My wife was out of town for an extended weekend, and I sent our sons to their grandmother’s house for the evening. I made plans to have dinner and then attend a concert with friends in another city. It felt safer to be out of my own city. Just getting out to the car was an adventure; we don’t have a garage, and it was daytime. I was half-dressed and wore a puffy jacket and sunglasses. On the drive to Louisville, I parked somewhere nondescript and changed into the outfit you see in the photo. I put on lipstick and my earrings. When I arrived in Louisville, I stepped out of our family’s minivan, presenting for the first time as Ashley. It was thrilling, terrifying, and fun…so much fun!

Dinner was a blast! My two friends, a straight female and gay male, are my most ardent allies. We chose a local restaurant, where it was widely known that a couple of their service staff was undergoing their own transition. It made sense for us. My girlfriend (using that term in the having a friend that is a girl sense) told me what to expect if I needed to use the restroom. I wasn’t going to use the men’s room. It wasn’t even a big deal. The best chance at me being read was when I ordered food. I hadn’t perfected my feminine voice, and that was probably a dead giveaway into my chromosomal makeup. At that point, I didn’t care; I was having too much fun.

The concert was great. I changed at my girlfriend’s office into skinny jeans and a plaid top with pink chucks. It was girly, but sensible enough for standing a few hours at a concert. I got carded on the way in. The dude with the flashlight didn’t make a big deal about it. In fact, he didn’t even look at me, knowing full well what was going on. I couldn’t resist; in my manliest voice, I said, “Well done, bro.” He then replied, “What ya mean?” I answered, “You know exactly what I mean,” and he chuckled. I thought humor was the best way to diffuse what might have been a mortifying situation. It was also a way for me to take back the power. I am happy with how it all went. The concert was a blast; standing room only, and with it mostly dark it allowed for plenty of anonymity. We left the concert a little early, because I was getting tired and didn’t think I’d last much longer.

As I think back on my experience, the two best meaningful words to describe my adventure are fun and gratitude. I know I am not a transsexual. The night wasn’t any sort of fulfillment for me, to be something other than who I am; it was more about reaching out within my own personal boundaries and enjoying the pure experience. My crossdressing is an indivisible part of me; it lies within the spectrum of what I want to explore. Thus, to be able to put on a dress and some heels was SO MUCH FUN. I am very grateful for my wife. She listened respectfully to me recount my evening after returning from her trip. She asked a few questions and generally seemed interested in hearing about it. I am also thankful for my allies. This experience would not have been possible without them. I leaned heavily on them, and they succeeded in making this experience a wonderful part of my coming out in the world. I don’t know if it’s naturally easy for them, but they made it easy for me.

I want to do this again, without a doubt, but I don’t see it as a frequent thing. As much as I enjoyed myself, I don’t want to devote that much time away from my family. But a couple times a year—I can see that as a distinct possibility. If I do venture out once more; I’ll be excited to share my story once again.

More Articles by The Author

Tags:
25 Comments

Leave a reply

  1. T.J. Byron 1 week ago

    Ashley,
    So much fun to read your story, nicely done. I am 72 years old & dressed in public since the 1960’s, to last weekend! Like you, & most CDERS, we kept parts, meaningful parts of our lives in a garbage bag in the garage….think of it. Fear motivates our actions. Not wanting anyone to know who is in that dress. Not a way to live. Since life is short, & mine, shorter by the days, much shorter than yours. Glad to venture out into this world you have created.
    I have gone out many, many yrs with relatives, gays, lesbians, whom ever wishes to come along. I am never looking for sexual activities, but I do like to look attractive. No one would ever say ” …hey, there’s T.J….”
    You have a long road ahead. Make the best of it. We old Gurls have paved the way.
    ENJOY being you!! T.J.

  2. cardigangirl 1 week ago

    Love the story. My wife also knows, but is not supportive. She knew from the start, but I think she underestimated it’s importance in my life. To keep the marriage together I had to get my clothes and stuff out of the house. I didn’t purge, because I know that doesn’t work, but they’re in storage, which is costly and not nearby. It’s been that way for a few years and is fairly ridiculous, but then life often is. So you are very lucky. Enjoy. I also love the outfit, I much prefer pretty and feminine than sexy/slutty. Huge congrats.

  3. Yanira Delgado 1 week ago

    Thanks for sharing your story. I’ve been trying to build the courage to go out of town for a concert dressed up in fem. I always bail at the last minute. I don’t have the support and I haven’t told any friends. I’m trying to read who I can tell that would be supportive that can be a part of my journey. This was very encouraging and I hope you have more milestones.

  4. Tiffany Flowers 1 week ago

    Thank you so much for sharing your experience.

  5. April Serrano 1 week ago

    Thanks for sharing and glad you had fun. I totally understand your points about challenges having a family, and also about not having a garage!

  6. Paula1 2 weeks ago

    Hi Ashley
    Great read I’m so happy for you that all worked out and you had a great night, I’m hopping to get out over the Xmas break if all goes well

  7. Marianne 2 weeks ago

    Hi Ashley,

    Thank you very much for sharing that wonderful description of your first time out with us. It seems you did everything right and had a marvellous time. You certainly look the part and I could borrow that cute outfit anytime girlfriend. Love the hair also.

    Marianne Tornander

  8. Gina Fuller 2 weeks ago

    Love your write up. Some of the things I have gone through. My wife hated me being feminine until she met another woman who is not living with us and mainly her. Her friend Diane keeps me in the feminine mode instructing how I dress and behave. My wife no longer wants to sleep with me. The moment I knew I was going to be a woman for ever I got rid of all my male clothing and set up a new wardrobe. I go out shopping with my wife and her female friend and enjoy it all the time, especially shopping for clothes and shoes. I meet a similar tg and we meet and drink in a pub frequently, so nice to be with a similar person. No sex as yet, that is to be decided on. My wife always asks when I return have you had sex. No is always the answer at present. Quiet open to questions from others.

  9. Laura Lovett 2 weeks ago

    Thank you so much for sharing this, Ashley – it’s a wonderful story made better by the fact it’s real and attentive to detail.

    Keep them coming!

    Love

    Laura

  10. Lisa watson 2 weeks ago

    You look great, love the natural look..
    Lisa

  11. Roxanne Lanyon 2 weeks ago

    I love your adventure! I do not have that situation, being divorced for over 2 and a half years, but I did go to Atlanta once toattend the SIGMA EPSILON meeting, a group of dressers there. I got lost, trying to find a restaurant, and had to go into a couple of gas stations and a furniture store to find directions. The scary part was, I was dressed en femme! Boy was I nervous! But no one said anything, and I got through it, and finally walked into the restaurant, met the girls, and had a wonderful dinner! Oh, I was so ecstatic! So happy! Roxanne found a new life, so to speak. The rest of the weekend, I just stayed as a girl, and met some wonderful friends, and had a very, very exciting time! How I adore being Roxanne now! I am soi happy when I get to put on a pretty skirt or dress! Now, if I only had someone to share it all with! Every day!
    Roxanne Lanyon, “A Girl for All Ages”

  12. Joanna Graham 2 weeks ago

    Wow, Ashley thanks so much for sharing. I relate a LOT to your family situation. We don’t have any kids but we’re around y’all’s age and my wife sounds like she has a lot in common with yours. Very encouraging for me to read this in thinking of our future. Also your outfit in the pic is super cute!

    Jo

  13. Janelle Washington 2 weeks ago

    Good on ya, girl! What a nice little adventure. You write well, I enjoyed the vicarious experience.

  14. Caroline Lau 2 weeks ago

    I like your story very much.As I myself planning to go public.Really need a lot of practice and courage.Just as you said at least once in a lifetime to cd public.

  15. Jessica 2 weeks ago

    I love your story.

  16. *skippy1965(Cynthia) 2 weeks ago

    Thanks for sharing your story, Ashley! Your outfit in the pic is just what the average woman wears-tunic over leggings with boots/booties. Glad you had a good experience-it gets even easier the more you do it!
    Cyn

  17. Julie 2 weeks ago

    Love this Ashley!

  18. Gabriela Romani 2 weeks ago

    Hi Ashley!

    You certainly jumped into the water all at once! And I’m glad it was a good experience! You did well by going out away from home for your first time, as it minimizes the chances of being recognized, so you were able to relax a bit more than if you were closer to home and more likely to run into somebody who may know you.

    And you are able to tell how you had a great time instead of just being wondering “How would it be?” That is something that helps being more at peace. Hope that makes sense!

    Gaby

  19. Katherine Jones 2 weeks ago

    Ashley,

    What a wonderful article! Being a closet cross dresser myself, it is amazing that you had the courage to go out! The night sounded like everything fell in place for a great experience. I am excited for you to have a good wife and great friends to help fulfill your dream.

    Regards,
    Katherine

  20. Kara Kelly 2 weeks ago

    A very good article. You are so lucky to have such a supportive wife and friends.

Log in with your credentials

or    

Forgot your details?

Create Account