Clothes Maketh The Man – Part 25.

I got up the following morning with a spring in my step, and the happy thoughts that I’d dodged a major disaster with Devina the previous night. With several tons of concrete hardening over her ridiculous chihuahua, and her none the wiser, I felt pretty positive about life.

True my girlfriend was a lying lesbian bitch, and there was the small matter of ongoing blackmail, I had a group of business partners who were using me as a sex object, but other than that, who amongst us is without a cross to bare?

As I left my apartment I was bathed in spring sunshine. I walked along the water by Esplanade Park when my cell rang and Steve started talking excitedly.

“Steve, chill! It’s a lovely spring morning. Relax.”

“What?” he said.

“Steve, it’s a spectacular day. Have you seen the sunshine?”

“Are you on something?” he replied. “It’s not like you to be this relaxed.”

“Oh, Steve,” I replied trying to sound as condescending as possible. “It’s a beautiful world out here. You should take a walk – enjoy the fresh air. I really feel Chicago never looks as good as it does in the spring. Don’t you agree?”

 “Yeah, whatever,” he replied. “You should take a taxi to the airport.”

I stopped and wondered for a moment if it were possible that the gods were taking a dump in my breakfast.

“Why,” I asked cautiously.

“Oh, it’s nothing bad. It’s actually something incredibly good. Spectacularly good. It seems our partners in San Francisco have thrown us a bone. A very big and juicy bone.”

“What on earth are you talking about?” I asked, my curiosity piqued.

“Well, it seems they’ve got a huge account that they can’t accept, but they want us to handle it. They’re going to take a cut, of course, but it’s a lovely piece of business.”

“What’s the account?”

“St Augustine’s Orphans fund. They’re based in Miami, and they’re a huge fundraising operation.  We’re to look after the direct marketing and social media. It’s a large account and we’re in it for three million or so. We get 10% of whatever we raise through the DM and social media side.”

“That’s a pretty sweet deal,” I said. “Why do they want us. I mean, they could go with Ogilvey’s or TBWA. Why choose us?”

“Well, they didn’t. Not really. They chose the San Francisco guys, but they’ve got a competing account, so they’re handing it off to us.”

“You know what this means?” I said.

“Sure I know what this means. We just tripled the size of the company with one account. You’re going to have to sew it up while I take care of things here, but it’s a pretty sweet deal.”

As I sat and soaked up the spring sunshine there was something nagging at the back of my mind. Right at this very moment there was nothing holding me to Chicago. I could jump on that plane to Miami and be unreachable. How perfect, I thought. And why not?


Later that day I stepped out of the taxi and into the foyer of the Miami beach front hotel with nothing but a small overnight bag and my tablet under my arm. I felt a wonderful sense of freedom, unshackled from either cell phone or chastity device. And no one but Steve could reach me.

I’d set up a Gmail account in the airport on the way out and sent Steve the details. He had forwarded all the documents I needed for this little escape, and was the only person in the country that knew where I was. I had even left my cell phone in Chicago. I’d pick up a cheap phone here, with a local number. I felt remarkably liberated.

After checking in to the hotel I took a walk along the strip. I found a mall where I could buy a light shirt, some nice trousers, and then succumbed to the urge to add a pale lemon blouse, with a lace cuff, and a light sand colored skirt. I could sit on the balcony in the hotel and enjoy the warm evening air in comfort. Some strappy sandals and pale pink panties completed the ensemble. With a feeling of excitement and anticipation I left the store and walked along beach in the direction of the hotel.

I was traveling light this trip, but was finding it increasingly easy to slip into femme clothes and looks. A little eye makeup and lipstick, and my hair getting so much longer, made a transformation a simple process. I hardly needed a wig at all.

By eight I’d had a quick bite and was back at the hotel. I responded to an email form Steve in Chicago, but there was little for me to do but relax. I had a morning meeting with the St. Augustine’s client, but other than that I was wide open. I had decided already this trip was a great opportunity to see a bit of Miami and maybe even get a little fishing in.

In my hotel room I laid out the new clothes on the bed. The male clothes I quickly hung up, but the skirt and blouse I looked at with the circumspect eye of someone who was increasingly a connoisseur. The skirt was lightweight, and almost floated in the air. The blouse bright, but not overpowering.

I decided I’d wander down and get a glass of wine and bring it back to my room. Then a seat on the balcony, and that stunning view. How perfect was that. I hurried to the elevator, keen to bring back a glass, and then change into the skirt and blouse. As I entered the bar I glanced around. The guests all seemed to be couples from out of town, with one exception.

Sitting at the bar nursing a long drink was a raven haired women perhaps five years older than myself. She wore a light crocheted cardigan over a pastel summer dress. Very elegant. She glanced at me and got to her feet as I walked to the bar, and held out her hand.

“Margo,” she said, “I thought you weren’t coming.”

“Oh,” I said, surprised. The barman caught my eye and I nodded to him. “Could I have a large glass of white wine,” I said and turned back to the woman.

“I think you’re mistaking me for someone else,” I said gently.

“Oh, I’m so sorry,” she replied, suddenly appearing embarrassed.

“It’s alright,” I said. Then, casting around for something to break the ice, I asked, “is it a date?”

The woman looked a little downcast and nodded. I got the impression this wasn’t the first time she’d been stood up.

“Well,” I said. “Whoever is standing you up is a colossal idiot. Can I buy you a drink?”

It turned out the woman, Margo, had been waiting for the last thirty minutes for an internet date that hadn’t showed. It was made worse by the fact that she’d driven in from Fort Lauderdale, where she lived, to come to this hotel. By the third drink I’d learned that she didn’t like driving generally, and hated travelling on hiways, the I95 being a pet hate of hers. She was unhappily employed in a failing travel agency, but felt she couldn’t quit, because Brett, the owner, had been at school with her and her father had backed over his bicycle when she was at a party at his house, when she was seven, and she’d been trying to make up for it ever since.

She would have quit last year, but he was getting a divorce and would never find anyone willing to work at the rate she was paid. Her mother was in a home for people with dementia and her father had taken off with a woman eight years her junior who worked on the cruise ships out of Miami, and he seemed more concerned with her than he had ever been about Margo.

One more drink and it was pretty clear there was no way she was driving home. I suggested a taxi, and she declined saying she was going to get a room. That was the point that I asked if she wanted to sit on the balcony and have a night cap. We found our way to my room, slid the key card over the reader and we both rolled into the suite on a tide of merriment.

We’d only been in the room a moment when she glanced at the bed, and swiftly looked back at me.

“I thought you said you were here alone?” she said, staring at the skirt and blouse.

“Oh,” I said. “Just some gifts.”

We went and sat outside in the warm night air and slowly drained the last glass. I’m not really sure how much of my life I shared with Margo, but I remembered much of the details of hers.

Now I should point out that in this entire exchange, there was no hint of me being a predator or having an ulterior motive. Margo was a striking woman, to be sure, however we really were just two people enjoying a chance meeting in a very innocent way. By the time she had made her way to the door, we’d exchanged email addresses, and after a light peck on the cheek, we’d said our goodbyes after a very pleasant evening.

It was late, and as I looked longingly at the clothes, I knew it was too late to really enjoy them. Instead I slipped between the crisp sheet and swiftly fell asleep.

And that was all there was to that first night in Miami. Little did I know that my connection with Margo might end up being the one thing in this trip that would prove to be my salvation.


The next episode can be found here.

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