Letting your inner woman out!

I am a very shy and keep-to-myself man.  But when I let Holly out, she’s everything I want to be but not allowed to be by society!  Playful, sexy, cute, girly, silly, loud, daring, etc!  Normally this girl is very much kept in the closet…well, this girl went temporarily running and screaming out of the closet one weekend…terrified the whole time, but I actually did it!

I made a very big step and approached the voodoo topic of my other side with my wife.  For the first time ever, it went well. It was still awkward, but for once I kept going instead of letting it just shut down. We both dumped our feelings on the table and as hard as it was, it was open and honest.  At the end of it all, we both were still smiling, said we loved each other and hugged and kissed. I was empowered by the fact that after a talk with her before leaving for this business trip, she said that she knew I would be dressing up while away. Knowing for once that I wasn’t “sneaking” around was SUCH A RELIEF!

Finding no one to go with me to a club or bar, I went out shopping instead! Granted, I started slow and went to Target…in my knee-high boots to go with my favorite black flowing semi-short but tasteful skirt and a very cute tight red top (can you see me smiling!). This outfit is now the first skirt/dress I’ve ever worn out in public! What a feeling! I’m such a girly girl, but the couple quick times I dared to go outside, I always went out in tight jeans because I was scared.

The last time I was out in California, though, I went to a CD store and had a wonderful time purchasing a lace front wig…what a difference that makes! For once I felt like I didn’t look like a guy in a dress, but rather the fairly attractive, extremely tall blonde woman I’ve always hidden away if I do say so myself 😉 I had so much fun strutting my stuff around Target in the women’s section and then the makeup section that when I left, I decided to keep on shopping!

I went out to a far more adult-themed store looking for a new corset as my last one just bit the dust. Unfortunately, they didn’t have any, but regardless I had a wonderful time browsing and talking with one of the sales girls who was very nice to me. Finally, I went out to Ross to look for new dresses. This was the first time I’ve ever shopped there, or really anywhere, while en femme…what a different experience!  I was able to hold up dresses to my body out in the open without feeling weird! I picked out five dresses and walked to the dressing room.

Now…this is where I have a past. I have taken dresses to the dressing room and had two VERY different experiences.  Ross makes you hang up the items out in the open. The first was wonderful…no judgment, and I confidently took the 3 elegant dresses back to the men’s dressing room. The second time was horrible…far more crowded, but emboldened by the first experience, I took a couple dresses up to the dressing room again. This time, the woman was argumentative, judging, and made me feel horrible! Never the less, I didn’t back down (even though I almost had a heart attack in the process) and after making a huge scene that I swore would go viral on YouTube, I walked back to the men’s dressing room with my dresses…and in the end bought one just to make a point to her!

So, now coming back to this trip, I walked up in my cute outfit on my first semi-confident real night out en femme with my 5 dresses and presented them to the woman at the dressing room. She gave me my tag without issue and I went to turn left into the dressing room because I thought it was the woman’s….well…it wasn’t! To my great surprise, she stopped me! She said, “No miss, this way”, and directed me to the women’s dressing room.  I’m fairly certain she made me out and was a little uncertain about how to handle it, but in the end, she was perfect.  I really can’t fully describe my thoughts as I walked in.  All I could think of was I was accepted!  I tried on all of those dresses, took pictures, and even walked outside of my stall to look at myself in the big 3-way mirror to get a better look…as well as to simply strut my stuff! 🙂  I, unfortunately, didn’t buy any of them, but the experience was amazing.

Fast forward to the next night…I was confident…I was excited…I wanted to go out again…so I decided on the dress that I had targeted as the first dress I would wear out in public! (Seriously, what is going on with me?)  So I did all my makeup, which thankfully I haven’t completely lost my touch after a long hiatus from “Holly time”, put on my dress, and then my wig.  I must say…I adore this outfit and want the world to see me in it! It is just so feminine that I love it!

When I went to open my hotel room door, I paused…again…scared about going out in public in a dress. I couldn’t let this chance pass…I opened the door and left…went to my car…and found a flat tire!  SERIOUSLY!!  Well crap, now what?   There was no way I’m changing a flat in a dress that doesn’t come to my knees!

Ok…back to the room, change into my “manly clothes”, but put a hat on to attempt to cover the fact that my face is completely done up en femme including one of my best sexy lips attempts!  There’s no way I’m wiping that off! I go back out with female face, but male clothes, change the tire, start putting things away when another man comes out to ask if I need any help…PANIC!! “No I just finished!”…”Wow, perfect timing!”…and that was that…in hindsight, I feel like a jerk for not thanking him for the offer, but I was too busy almost climbing into the trunk to hide my “perfect” face!

Ok…swallow heart…alone again…quickly put everything away and walk back inside. Ok, I didn’t go through all this to just cower in my room, so I put my dress, wig, and heels back on and went out!  Granted I only got a takeout salad at a pizza place and then went back to Target to buy a bottle of wine for myself, but still, I was strutting around in my dress and having fun with it!

The priceless point of the evening was when I got carded for the bottle of wine at Target! The girl asked for my ID and I handed her my male ID. I felt sorry for her because she looked so shocked that she wasn’t sure what to say! I just smiled at her and kept talking (in a voice that definitely needs work…remember, never been out in public before!) She was a trooper and finished checking me out.  I then got back to my room and realized I only had plastic cups, so I pressed my luck and walked to the front desk in my dress to ask for a “glass” glass for my wine!  Again, I was amazed that I was completely accepted and treated as a woman.

All of this has shown me that I may not pass if people look closely, but even when I don’t, people accept me for who I want to be or who I decide to present at the time.  It was a horrible travel weekend full of flight issues, lost bags, feeling ill, no sleep, etc, but it had been one of the most amazing trips! For the first time ever, I let Holly truly out in public dressed as the girl she was meant to be and I had no issues…other than my boots being too tight after 3 hours of walking around, but what’s a girl to do? 😉

The world may not fully accept us or understand us…heck most of us don’t understand us…I know I don’t fully yet, but I was accepted, treated wonderfully, and I couldn’t have asked for anything more.  I wish the same for every other girl looking for their first opportunity to let their true selves out to play!

 

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54 Comments
  1. Chrysta Minot 6 days ago

    Thank you, Holly!

    Love your writing style, your candor, and your courage! I will be following you in your footsteps! Yikes!! Woo Hoo! Life is scary and exciting! Love to you!

    And thank you from my heart!

    Sincerely, Chrysta

  2. Melissa Milano 1 week ago

    Thank you Holly. That is a wonderful account of they types of experiences a crossdresser may face. I am not at the point that I can go out in public yet and my wife is not as understanding at least at this point. I hope I can continue to move forward like you did!
    Melissa

  3. Shannon Fox 2 weeks ago

    Love the story holly you sure had a good time. I haven’t been as brave as you and went dress yet but I will. Also would love to dress up as a Disney princess to. I would love to be Snow White. Hugs and kisses

    • Author
      Holly G 1 week ago

      Thanks Shannon! I’d totally have to be in one of the more traditional princess ball gowns like Belle’s or Cinderella’s. I just love the old billowing dresses that are no longer around. I guess since I’m a blonde these days, I’d have to go with Cinderella 🙂

  4. Angie Walker 2 weeks ago

    Thank you for such an inspirational story Holly, especially how you were able to discuss things with your wife. I am still working on the courage to do that.

    Angie

    • Author
      Holly G 1 week ago

      Thanks Angie. Just beware with approaching your wife on all of this. Now mine wishes that she never knew and it definitely has caused changes in our relationship. Some strike gold and their partners are completely understanding. Others can never recover. I’m somewhere in the middle right now and dealing the best I can.

  5. Amaia Mercado 3 weeks ago

    Oh ..my ….lord, whew! I know that day took some real courage there! Thank you for sharing your experience to give me the courage to keep pressing on. Oh girl, my heart was beating so fast as I read your story, because I have been in a similar experience: challenge after challenge and not giving up on the end. So thank you for sharing your experience!

    • Author
      Holly G 3 weeks ago

      Thanks Amaia! It was definitely a heart pounding experience, but I was smiling from ear to ear with my perfect lips 🙂

  6. Rebecca Leeann Allen 3 weeks ago

    Great story i enjoyed it.
    Every time i have been to Ross they treat me like the lady i am

    • Author
      Holly G 3 weeks ago

      Like I said, the first time I went was wonderful, but the second time was simply awful! But both of those times were in male mode and trying on lovely evening gowns…this time was WAY more fun and excepting!

  7. Elise Michelle 3 weeks ago

    Wow. Thank you for such an inspirational story. I’m so glad you had such a lovely trip and were accepted for being you! Why is that so hard for some people to do?

    Kudos to be you!

    Hugs, Elise

  8. Cris White 3 weeks ago

    what a story. I’ve just started going out myself with my wife on the weekends. Shopping. The wig issue is the one I’m struggling with to, cover my forehead . Also my nose. Your story inspired me to be more courageous . I starting to believe that a positive attitude helps a lot to pass. Cris

    • Author
      Holly G 3 weeks ago

      I had the best time buying a wig at a CD store out in San Jose last year…it was so much fun and I LOVE my wig! The lace front style is a must. It cost me a fortune, but that really got me over the hump of feeling confident and beautiful.

  9. Anastasia Irish 3 weeks ago

    Great read Holly
    I hope to someday have that kind of experience, without the flat tire of course. Your bravery with your wife and the outside works is truly inspirational.
    Thank you for sharing.
    Hugs
    Anastasia

  10. Janine 3 weeks ago

    Thanks for sharing your first time out with us
    Especially when you got ready to leave and found that flat tire.
    What a horrible way to start your leaving dressed en.femme.
    It reminds me of the time when I was on a toll road in Florida and I was wearing a skirt and blouse coming back from being at the Florida Mall.
    My car started shaking and I knew that I was getting a flat tire.
    I moved to the shoulder and put my hazard lights on when I got stopped.
    I was sitting there wondering what I was going to do when a State Farm courtesy truck stopped behind me.
    The driver came up to my side window and asked me if I needed him to put my spare tire on for me
    In my best feminine voice I told him yes and popped open the trunk so that he could get my spare tire.
    I started to get out of my car and he told me to stay in the car for safety reasons with all of the traffic on the road.
    In a matter of minutes he had changed the tire and closed the trunk.
    He came up to the side window and told me that I was alright to go.
    I gave him twenty dollars and thanked him for helping me.
    If it wasn’t for him stopping to help me I don’t know what I’d have done.
    Like you I didn’t want to change a flat tire wearing a skirt and heels.
    It taught me that I should carry a change of male clothes with me when I go out dressed en.femme because you never know what might happen.

    • Author
      Holly G 3 weeks ago

      Wow…I at least had a chance to go back inside and change…I’m not sure what I would have done. I guess just sucked it up or hoped that someone would stop to help me. At least while I was en femme this time, I felt like I looked good enough for someone to stop to help 😉

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