Holly’s First Halloween

A dream come true…

I can’t tell you how long I’ve longed to experience what it would be like to be one of the Disney Princesses.  Those elaborate beautiful ball gowns, the petticoats, the beautiful shoes, the layers of hair…elegant, beautiful, breathtaking…

I’ve never been able to dress en femme for Halloween, although like most of us, I’ve ALWAYS wanted to!  My wife and I would often host a costume party, and I usually have one of the more elaborate costumes of the group, but always a male character.  This year, with Covid happening, there would be no gathering at our house. I was, however, invited to go to a Transwomen/CD Halloween Gala for the first time, by an old friend.  I didn’t think this would be possible, although you can imagine my mind racing with possibilities!  I talked to my wife about it and she eventually agreed that I needed to have a group of friends who knew me as Holly (I’m still very much in the closet to those who know me) and who I could socialize with while exploring this side of myself.  She not only said I should go, but she actually tailored my dress to fit me! It was way too short, as things tend to be on a 6’1″ frame, and a little snug in the arms. The petticoat I had bought at Goodwill to go with it was not very full.  She did so much to this dress for me, words can’t describe what it meant. We’re still working on accepting this part of me and she’s never met Holly, but this was such a loving gesture that it made this dress mean so much more to me.  While she worked on the dress all week, I kept my face clean shaven so I could practice my makeup skills to ensure I’d be ready for the night. (Thank God I did this, because the first few attempts showed how out of practice I was!) In a final, loving gesture before I left for the weekend, my wife custom-made a matching mask with gold trim for me to wear in public areas.

As this was my first trip focused entirely around my femme side, I told my wife I’d like to dress at home and leave as Holly to enjoy as much time as possible.  I went downstairs to get ready in private.  I started with my nails because I had peep toe heels and I wouldn’t have gloves on all night.  Obviously, that meant I wanted my nails to look fabulous! This activity added quite a bit of time when I botched first my thumb, and then two fingers while I was fixing my thumb! UGH!! Finally, I moved on to my face and did a decent job with daytime makeup. With my face done, I finally got dressed and started to feel the full rush of what I was about to do. I packed everything up in my car with the garage closed, got in the car, opened the garage door, and slowly pulled out into the world with Holly on full display!  (Heart hammering at this point…)

I started to calm down as I drove further out of town. I stopped along the way a few times, used the ladies room, bought three dresses, and got a snack. Eventually I checked into my hotel where they didn’t even bat an eye that I was dressed en femme, checking in under my male name.  Score! I changed into one of my new dresses and headed to the mall to go shopping and meet my friend for lunch. I walked around a little before lunch, where my friend and I met for the first time as women! She and I had a lovely lunch and talked on and on about everything. We followed lunch with some shopping at a few stores before she headed to get her makeup done for the gala. I stayed a little longer on my own, bought a cute shirt, went back to the hotel, and changed into it along with a pair of leggings to go get a couple things from Walmart. Now this was a body hugging, leave nothing to the imagination outfit that many women wear and I LOVED that I felt like I could pull it off, and I did! I wanted to make sure that small victories were enjoyed and savored all weekend.

With the shopping done, now came the moment of truth…getting ready for the gala.  The butterflies in my stomach started doing backflips. I showered and shaved (electric followed by a razor which really leaves your face very smooth) and started my makeup. I was so nervous that I’d mess it up, but all the practice this week really paid off! Even the stupid eyeliner which is always an issue went well for me that night. Heart really starting to race now…I slip on my 4-3/4″ silver sparkle heels, then step into my petticoat and zip it up. Taking a deep breath as I walk over to the dress itself, I unzip it and take it off the hanger, gather it all up, and drape it over my head before zipping up the back. It now hugs me in soft satin material. Starting to calm down a little, I avoid the mirrors as I walk over to take my wig off the stand, pull the wig on and flip my hair back. Finally, I look in the mirror so I can attach the high ponytail piece to top it all off.

I melt…

My heart just can’t even…emotions…overloading…..

My mouth can’t smile big enough to capture how I feel at that moment. I add my earrings and necklace, and pull on my gloves. I have never felt this beautiful in all my life. The dream I’ve played out so many times of dressing as a princess has, at long last, become reality. And here I am! Words can’t describe how I felt –  and the night was just starting!

I stepped out my door for the first time ever without any hesitation.  Instead, I felt complete, filled with utter confidence and excitement. I went to my friend’s room, and when she opened the door she was stunned. Her friend also stopped down as she told me how much Belle meant to her as well – especially that dress!  That reaction was a theme throughout the evening as we went down to the party and I met, for the first time, a group of transwomen and crossdressers. They were AMAZING!! You could look around the group and see how everyone was so happy to be able to express their feminine side however they wanted – elegant, slutty, silly, super hero, scary, you name it – all were accepted and having a ball just being themselves. For an evening, I was one of the girls and I loved every minute of it. We talked, joked, danced, twirled, sang, drank, joked some more, took thousands of pictures (because that’s what we do!), and just had so much fun. They even had a costume contest and the judges (the hotel staff) chose “our lovely Belle” as the best overall costume! Seriously! My emotional bucket couldn’t take much more tonight…

Eventually, as the night wound down and I headed back to my room, I didn’t want the evening to end. So, of course, I took more pictures and just enjoyed being in that dress, that moment, feeling every bit the woman I looked like. And loving it.

I learned so much from everyone there as we all shared experiences which helped expand and normalize my outlook on so many things.

The next day I got up and went for a run for the first time totally en femme. (That was also quite a learning experience in what you need to do with forms while running!)  Afterwards, I cleaned up and put on another one of my new dresses and went to meet one of my new girlfriends for breakfast. Again, this just felt so normal and wonderful. We talked forever about anything and everything. Since we both had a drive ahead of us, we went our separate ways while a staff member said, “Have a wonderful day, ladies!” on our way out.

I have so many new girlfriends to share this side of my life with, and whom I can lean on when I need a friend.  I’m still processing all of the emotions and love and joy that went into and came out of this experience. But I do know that every time I look at one of my Belle pictures, it all comes roaring back and I’ll cherish that forever!

More Articles by Holly G

• Finally, A Trip Happened for Holly!
• Letting your inner woman out!

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