Friday, November 3, 2023

Halloween Encounter with a Colleague

By Paula Gaikowski

Last week, while working online with my colleague, a cheerful woman in her 60’s, our conversation took a delightful turn toward Halloween. Little did I know that this discussion would lead to an unforgettable connection and a dash of personal revelation.

As we chatted, my colleague shared stories of her past Halloweens, particularly huge Halloween parties featuring crossdressing contests and drag shows that she attended. In response, I chuckled and mentioned my plans for Halloween were dressing up as a woman. She couldn’t hide her excitement and urged me, “Please get some pictures!”

With a mix of apprehension and a desire to connect, I confessed that I had already taken some snapshots during a costume try-on session the previous weekend. I didn’t mention that I am typically trying on costumes every weekend of the year.

In a brave move, I shared my screen, revealing my three en femme costume choices. One featured me in black pants and a matching top, another in a flowing skirt and sweater with funky boots and the third in a sleek pencil skirt, a black sweater, modest heels and an air of confidence.

Her reaction was the epitome of positivity and support. She not only complimented the outfits, but also candidly told me which one she preferred. It was heartwarming to witness such acceptance and our ensuing conversation was filled with laughter and camaraderie.

After this impromptu and encouraging chat, I couldn’t help but wonder how my revelation might affect our professional relationship. The following Monday as we met online again, her very first question was, “How was your weekend? How did the party go?”

I beamed and told her it went splendidly, though I had opted for a different outfit – a teal skirt suit that had long been a favorite. 

She couldn’t contain her curiosity and asked to see a picture. I obliged and shared details about my days presenting as a woman. I shared a few anecdotes about going out and about as a woman, how I found it exciting and fun to cross boundaries and see life from a different perspective.
In sharing these tales, I subtly dropped hints about my identity, though I hadn’t explicitly mentioned being transgender. However, the descriptive narrative I told was thinly veiled by the cover of Halloween. She was probably expecting a caricature of a woman, the man in a dress prank. My accomplished femulation probably extinguished any doubts about this being my first time to the rodeo.

The conversation was filled with positivity and praise.

“I think it’s great that you did this.”
The feeling of validation was nothing short of exhilarating. It was as though I had found a new friend who appreciated and celebrated this part of me that I’ve kept hidden for decades.

Reflecting on this memorable encounter, I can’t help but smile. It’s incredible how a simple conversation about Halloween can lead to profound connections and understanding. 

While the Good Ship Lollipop might not be everyone’s preferred mode of transport, it’s a wonderful feeling to sail on it, embraced by acceptance and camaraderie. 

Who knew that discussing Halloween costumes could lead to such a heartwarming connection in the midst of the corporate world?

Source: Rue La La
Wearing St. John


  1. Paula, my favorite of those three outfits is the middle one with the black sweater and the flowing skirt. I have that very skirt and just love it with a black sweater, it is one of my absolute favorites. I am always afraid I put it into rotation a little too frequently.

    Your conversation about Halloween with your colleague was heartwarming.


  2. More than 20+ years ago before I retired my female boss mentioned she had dressed her husband in one of her old high school prom dresses, heels, wig and makeup for a Halloween party. All the women begged for pictures of him, but this was before cell phones with cameras. I knew her husband who had the stature of height and body type of easily carry the presentation off. I did wonder what their reaction would be if he was a confirmed cross dresser. I felt envious of him. All my Halloween adventures were solo outings.

    1. When I dressed as an office girl for Halloween at work, I found that the women were fascinated by my "costume." It did not make much difference whether they knew I was trans or just a guy in a costume. My presentation was so good that they loved it.

    2. Those same women would gather in front of the office building to watch the annual "Walk A Mile In Her Shoes" fundraiser trying to guess which male was a cross dresser based on the ability to walk in high heels. They seemed so accepting but I always wondered what would have if their husband came out as a cross dresser. How would it affect their marriage? On another site it always seems like acceptance but "Not in my backyard."

  3. IWASLUCKY,MYWIFETOLDDMETODOWHATEVERineededto be the personyou are