Brenda’s heart raced with excitement as her cab pulled up to the charming boutique hotel in Midtown Manhattan. The iconic skyline loomed above her, a perfect backdrop for her one-day escape. She had carefully chosen this hotel for its central location and reputation for discretion and warm hospitality. It was the ideal place for her to embark on a personal journey of self-expression and exploration while on business travel.
The crisp fall air greeted her as the cab door opened and the doorman, a distinguished gentleman in a sharp navy uniform, stepped forward with a warm smile.
“Welcome, Ma’am,” he said smoothly reaching for her luggage. Brenda, still dressed en homme, returned the greeting politely.
The hotel lobby was as elegant as she had imagined—soaring ceilings, polished marble floors and floral arrangements that added a touch of grandeur. The front desk staff were efficient and courteous, handing her the key to a room on the 12th floor with a genuine smile.
Once inside her room, Brenda let out a contented sigh. It was perfect. The plush king-sized bed seemed to beckon her, the floor-to-ceiling windows offered breathtaking views of the city and the bathroom, with its marble vanity and rain shower, promised a luxurious experience. She had two precious hours to prepare herself before venturing out into the city and she intended to savor every moment of the transformation.
Brenda unpacked her essentials with care, arranging her makeup, wig and accessories on the vanity like tools for an artist’s masterpiece. From her suitcase, she retrieved her outfit for the day: a chic black wool poncho, a Ralph Lauren business suit (a thrift-store treasure), black stockings and her favorite pointy toe Italian boots—perfect for navigating the city’s bustling streets.
She began by stepping into the spacious bathroom and turning on the shower. The room quickly filled with steam as she let the hot water cascade over her, washing away any lingering nerves. Wrapped in the hotel’s plush bathrobe afterward, she felt her excitement build as she prepared for the next step.
At the vanity, Brenda started with her makeup, taking her time to create a flawless look. Primer, foundation and concealer created a smooth canvas, while soft autumnal eyeshadow tones highlighted her eyes. A touch of eyeliner and a generous coat of mascara brought them to life. A rosy blush added warmth to her cheeks, and a cherry-berry lipstick provided the finishing touch.
Next, she styled her wig, brushing it carefully so that it framed her face perfectly. She admired how it transformed her reflection in the mirror, boosting her confidence with each stroke.
Finally, she slipped into her outfit. The business suit hugged her figure just right and the red nails and black stockings added an elegant touch. As she stepped into her boots, she felt an empowering click as they met the floor. She draped the poncho over her shoulders, added simple gold earrings, a bracelet and her favorite chunky necklace.
After a final spritz of her favorite perfume, Brenda paused to admire herself in the full-length mirror. The reflection staring back at her was poised, confident and radiant. For the first time in a long while, she felt completely at ease in her own skin.
As Brenda stepped into the hotel lobby, the golden morning sunlight streamed through the glass doors, illuminating the polished marble floors. Her poncho billowed slightly as she walked, the rhythmic click of her heels creating a comforting soundtrack.
The doorman, who had greeted her earlier, was at his post by the door. As he held it open, he offered her a warm smile.
“Good morning, Ma’am,” he said, tipping his hat. “It’s a beautiful fall day—perfect for exploring the city.”
Brenda’s heart fluttered, but she managed a confident smile.
“Thank you,” she replied softly.
Before she could step out, the doorman added, “If you’re looking for a great lunch spot, there’s a café just a few blocks down with lovely autumn specials. And if you’re in the mood for a drink later, Illusions next door is wonderful—very welcoming and inclusive. I think you’d enjoy it. They have a drag show tonight.”
Brenda blushed, feeling both seen and accepted.
“Thank you,” she said, her voice steady despite the nervous emotions welling up inside her.
Brenda thanked him again, her curiosity piqued, and set off on her journey. I guess he read me pretty good as she looked into the reflection from the window. Stubble? Bad lipstick? Man’s voice in a fake falsetto not enough?
The city greeted her with its usual hum of energy—taxi cabs honking, pedestrians rushing by and the din of sirens. Brenda felt an exhilarating mix of nerves and joy as she joined the throng, blending seamlessly into the bustling streets.
She took her time wandering through the iconic Central Park, savoring the vibrant autumn colors that painted the trees and pathways. The crisp air kissed her cheeks and she couldn’t help but smile as she dropped a few dollars into a saxophonist’s case. His soulful tune adding a touch of magic to the moment.
Stopping at the café recommended by the doorman, she treated herself to a delicious lunch of smoked turkey sandwich and spiced chai latte. Sitting by the window, Brenda gazed out at the world, feeling entirely at peace. She realized how freeing it was to simply be herself, without fear or hesitation.
Brenda found herself slowing down in front of a boutique with a particularly striking window display—elegant dresses paired with bold statement necklaces. A good time to look at my reflection.
Across the street, a small vintage store tucked between a florist and a bookstore caught Brenda’s eye. The window displayed an eclectic mix of items—retro handbags, costume jewelry and rows of vintage shoes that seemed to call my name. Intrigued, she stepped inside without hesitation.
The store was cozy and packed with treasures. As she browsed, her gaze landed on a pair of classic black leather flats, lightly worn, but in excellent condition. She slipped off her boots and tried them on. They fit perfectly as though they’d been waiting just for her. At only $20, they were a steal. The store clerk, a friendly woman with a keen eye for style, complimented Brenda’s outfit and wrapped up the flats in a crisp paper bag.
“Perfect for easing your feet after a long day,” the clerk said with a wink. Brenda laughed, already feeling relief at the thought of switching shoes later.
The clerk suggested a wonderful leopard print silk scarf and appropriate clip on earrings. Oh my, the scarf really completed my look.
As the day turned to evening, Brenda returned to her hotel room to freshen up. She changed into a more glamorous outfit for her visit to Illusions—a Stana Short black dress, shimmering nylons paired with her new earrings, leopard print silk scarf and leopard print high heels. Brenda looked fantastic and kind of a bit sexy! Bring the flats, don’t forget.
After slipping off her wig and freshening up in the bathroom, she decided to step outside briefly to grab some ice from the machine down the hall. In her haste, she forgot one crucial thing: her room key.
The moment the door clicked shut behind her, Brenda’s heart sank. She patted her crossbody bag, realizing it was still inside along with her phone and backup key. The reality hit her—she was locked out, standing in the hallway in her dress and heels, without a single way to get back into her room.
At first, she considered waiting for a passerby, but the hotel was eerily quiet and the thought of standing in the hall much longer made her even more anxious. Gathering her courage, she walked down towards the elevator to use the service telephone. Each step echoed loudly in the empty corridor, her heels clicking on the polished floor. Brenda felt every inch of her outfit—the hem of her dress brushing her legs, the delicate click clack of her shoes—and it only added to her growing nerves and hysteria. Please do not let me have a panic attack right now.
She called the front desk, she explained her predicament to the receptionist, who responded warmly and reassured her that it wasn’t a big deal.
“We’ll send maintenance up to unlock your door,” she said.
Brenda nodded, relieved, but still felt a flutter of anxiety. While it wasn’t illegal to wear what she was wearing, she was painfully aware of how out-of-place she might seem. Brenda looked in the mirror about to burst into tears as she tried to massage her male hair into a quasi butchy female hairdo.
Minutes later, the maintenance guy arrived. He was in his mid-thirties, wearing a tool belt and a creepy, friendly smile.
“You must be the one locked out,” he said cheerfully.
Brenda nodded keeping her voice steady as she explained which room was hers. The man glanced at her briefly, then did a quick double-take, his eyes lingering just a little too long on her legs and heels. Brenda felt her face flush. She wasn’t sure if it was curiosity or admiration, but his gaze made her self-conscious. Is this what women call ogling?
To his credit, the maintenance guy didn’t make any inappropriate comments. He chatted politely about how common lockouts were as they walked back to her room, but Brenda couldn’t shake the feeling of his eyes occasionally darting toward her outfit. She stayed composed, even though she was inwardly cringing.
“Just let me get back in my room,” she thought.
When they arrived at her door, the maintenance guy made quick work of unlocking it.
“All set,” he said with a grin, handing her a backup key. “You have a good night now.”
Brenda thanked him and quickly stepped back into her room, closing the door firmly behind her.
Leaning against the door, Brenda let out a long sigh of relief. This was a scary WTF moment. It took two glasses of wine to calm her down and stop shaking. The encounter had gone smoothly enough, but the way he kept glancing at her legs and heels had left her feeling vulnerable. She resolved then and there never to leave her room without a backup key again. She put the backup key into her bra cup. Going forward, her purse would always be hanging at the door handle to avoid this again.
After all this, it was no problem taking the elevator down to the lobby and walking next door to Illusions.
The welcoming atmosphere of the bar and the lively drag show made her feel right at home, surrounded by laughter and acceptance. Brenda was invited to sit with a few gurls and spent an hour of chitchat and exchanging dressing tips. It was safe to be with others even after a few men had come to the table to say hello and hope for a chance to ply us with drinks. Well, it was time to head back.
New York City had embraced her in ways she hadn’t expected, offering her not just an adventure, but a profound sense of belonging. As she sipped her cocktail and joined in the applause for the performers, Brenda realized this was a day she would treasure forever—a celebration of courage, confidence and self-expression.
While sitting in a meeting with customers the next day. Brian was dreaming of how enjoyable his day as Brenda was and sadly, how he may not be able to get dressed up again on this trip and hoping for a last minute meeting cancellation, when he was snapped out of his daze.
Hey, Brian, what do you say you seem lost in thought?
“Well, I suggest option 1 as it will save you money and bring the ROI to less than 12 months and it’s a good start to prove out the effectiveness of streaming the delivery process. I would like to sit down with your team tomorrow morning and start white boarding some ideas while Donald gets the procurement stuff sorted out. We can talk about this over dinner this evening”
Brian, I am so sorry,, but this evening will have to be an early one as I have a thing with my daughter tonight and first let me introduce you to my team and we can schedule for tomorrow. Let me go get the girls.
Anita (I loved her color-block dress and she had these wonderful black toe capped studded flats) was very young and Janet the business analyst was a beautiful middle-aged woman who had this wonderful polka dot skirt (below the knee) and luxurious silk blouse. I wanted to dress like them and even be them. I was jealous and I looked forward to working with them.
The best part of the day was when they told me that we are better off meeting the following week, so they had time to prepare for the meeting and give procurement some time to issue the purchase order.
I sorted out my travel plans for next week, found a restaurant with an early reservation nearby, and found two thrift shops to check out between the restaurant and my hotel. My colleague made up some lame excuses about a ton of work to do and I found myself with some free time.
As I looked into the elevator mirror on our way down, I saw Brenda smiling as she tried to plan her free time this evening and a chance to spend a good part of tomorrow out and about in the city all over again. All she could think of was having her own polka dot skirt and silk blouse to wear.
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| Wearing Bebe |
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| World War II Royal Australian Air Force (RAAF) female impersonators |
