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!

 

The following two tabs change content below.

Holly G

MTF Cross dresser, chatty girl, and high heels addict!! I'm still on my journey to understand who I am and where I am on the beautiful spectrum, but I'm doing much better about releasing the shame and accepting the truth. My inner girl seems to long for a different time. I often fantasize about being a Disney Princess with their beautiful ball gowns! Corsets, petticoats, and elegant ball gowns...why did they ever fall out of style? 🙂

Latest posts by Holly G (see all)

Tags:
58 Comments
  1. Cloé (CC) 1 year ago

    Holly,
    The world in most part has been accepting of Cloe. In many ways our struggle is no different than any other marginalized group. We do risk a lot by being our trues selves wit those who fear what they do not understand and take action against such.
    I know I don’t understand the depth or breadth of Cloe, but she’s amazing and deserving of being alive and the remainder of my lifetime of discovery. This may not be your path and rightly so, but know you have more sisters then I had anticipated close by who understand the struggle utterly.

    Hugs,
    Cloe

  2. Lisa James 1 year ago

    Hi everybody,
    I am a newbie here and I am trying to find someone who will do a custom order for me.I am trying to get a tennis dress (with the knickers!) and a ballerina outfit, is there anyone out there who will make these for me please?

  3. Olivia Livin 11 months ago

    Way to go Holly! That was alot to push through, but you did it, and enjoyed.

  4. Jasmine Jeffries 7 months ago

    Holly loved your story Jasmine XOXO

Leave a reply

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

or    

Forgot your details?

Create Account