From Secret to Spotlight: My First Halloween Public Outing as Amanda

The Courage to Step Out: A New Beginning

I am taking this opportunity to share one of my first public experiences in a group setting as “Amanda,” my female persona, when I cross-dressed. Full-transformation cross-dressing had become a hobby of mine when I was home alone. My ex-wife traveled for work, which allowed me the time to explore my character and the freedom to experiment with make-up and dressing styles.

About eight years ago, I was invited to a Halloween party with my men’s softball team and their dates/spouses. The team captain hosts this annual event at his home. I’ve been invited to this party for several years but never attended because my ex-wife was not a fan of making the long, distant drive to the host location.

Since we had recently separated, this was my opportunity to convince myself to attend as “Amanda.” My ex-wife had discovered my propensity to indulge myself in crossdressing and was not happy or understanding. She didn’t believe the discovery and my explanations about my crossdressing in our home. She was convinced I was cheating on her and/or engaging in homosexual activities.

My ex-wife continued to disbelieve me and then took it upon herself to announce to the world and everyone we knew through social media that I was crossdressing, lying, and cheating on her. She even claimed that I was living a double life. I was repeatedly accused and called a liar, even when I promised her I was being honest. She then decided to tell all of our families and close friends about this very private part of our marriage and personal lives.

This sparked my curiosity to discover how people I knew would react if they saw me as “Amanda.” So, I started to create a plan to showcase myself crossdressing as “Amanda.” My heart and ego would be on full display for the public to see in this daring step out in public.

The Story Behind the Costume: “Caitlyn” Jenner

First, I needed to secure a date, someone I could go with who could provide cover if needed, and someone to support “Amanda” in this terrifying and anxious experience. Next, I had to choose what character I would decide a character and costume for Halloween.

This is where my creativity took shape and gave me a superb idea. “Amanda” was going to go as the amazing Bruce “Caitlin” Jenner! A transgender and former Olympic athlete, spokesperson, and member of the popular reality TV show of the blended Kardashian and Jenner family.

Finally, I had to secure a costume that would be passable, awe-inspiring, and beautiful enough to “trick” my friends into thinking what a “treat” it would be to see Amanda as the woman I had fantasized about expressing when crossdressing.

Creating the Look: From Head to Toe

Starting with my costume, I chose a black jumpsuit that was already in “Amanda’s” wardrobe. I then paired the jumpsuit with matching black heels and a beautiful, longer brunette wig. At the time, I was still using homemade breast enhancements. The final steps were to apply proper makeup, a necklace, earrings, and a small handbag. The overall results were convincing, and I was excited for the Halloween party.

My date for the evening was super excited to join me for the event. She and I met earlier that year at a bar that my teammates visited after our games. Many of my teammates sing Karaoke and she happened to be singing one evening. I introduced myself to her that night and offered to give her a ride home.

My new friend is a stunning female vocalist with ample bust, hip, and buttock curves. As a Karaoke performer, she exudes confidence both on and off the stage. She is known for her powerful vocals, curvy body features, and really long, curly jet black hair.

The date for the Halloween party had arrived, and the weather forecast was ideal for Fall. Our costumes for the party looked fantastic, flattering, and very feminine. This beautiful female duo would be on full display at the party and ready to steal the show.

The Big Reveal: Entering the Party as Amanda

Upon arrival at the party, we were greeted by the host. He had no idea who we were. My transformation had everyone guessing who I was and what my character was. I replied, I’m Caitlin Jenner, which created a great deal of laughs. They were all in shock and awe, with questions flying at me frantically and with disbelief.

Who are you again, who did your make-up, are those breasts real, and how can you walk in those heels? After making the rounds at the party, I promptly found a quiet space outside in the backyard, which I thought would shield me from too much more attention.

As the night continued, I was constantly sought out for more questions about my “costume,” shoes, wig, and makeup, along with the reason behind choosing my character.

Everyone seemed to enjoy the effort put into my costume choice, and I was happy to receive many compliments as the night went on. The entire experience was very positive and put me at ease among my teammates, friends, and new fans.

As the costume contest votes were being cast, more and more people wanted to confirm my identity, and my teammates were sending their spouses and dates over to ask who I was on the team; I told them all my team nickname, “Popeye,” and they were all mesmerized.

I even had one teammate ask me to go across the street to his house to show my wife and older kids my costume, which blew them away. It was all great fun, and I’m proud that I chose to dare myself and take this chance to share my hobby.

The Moment of Truth: Winning the Contest as Amanda

Finally, the entire team gathered for the costume contest prize announcements and the voting results. Every attendee had submitted votes, and I ended up winning a tie for first place! This made my initial public experience in a group setting very rewarding! “Amanda” has been going out in public and is liberated ever since, building confidence each time.

In the near future, I will have many more stories to share with you. This hobby has allowed me to be expressive in so many different ways, whether I’m home alone or out in public. I look forward to sharing these stories and many more topics with you.

Thank you so much for this wonderful platform and the opportunity to share my experiences. Please feel free to comment and stay tuned for my next post.