Matchmaker 03: March

Normally when a client contacted me to engage my services, I was responsible for everything, but not this time. My client, Heston Mallard, knew exactly what he was doing and what he wanted. He was taking a working vacation during the month of March to give his new sailboat a shakedown cruise in the Caribbean. I only had to provide his companion.

Heston was different than most of my clients. Like all my clients, he was wealthy, worth just a tick under a billion dollars on paper, but unlike most, he was a little younger, twenty-nine, and a confirmed bachelor. Many of my clients were in their mid to late forties, or older, and were looking for someone special. That was where I came in. I specialized in finding that special someone, arranging a dream getaway, and allowing nature to take its course.

Not this time. Heston claimed he wasn't interested in a relationship. He was only looking for someone to spend a month on his boat with him, someone whose company he could enjoy, and when the month ended, the pair would go their separate ways. I first thought of turning him down as a client. Despite what my critics said about me, I didn't run an escort service, and I didn't provide women as playthings for the wealthy. I hadn't discovered what Heston said he wanted until I was interviewing him. He was very clear he didn't have time for long term relationships, that he was married to his work, and he liked it that way. The only reason I accepted him as a client was because during our interview, I realized he was deluding himself. I didn't have time or the inclination to dig into his emotional baggage, but it was clear he was trying to make himself happy by throwing himself into his work. If he truly wanted nothing more than someone to warm his bed at night for a month, he could have found plenty of takers for that role on his own. By coming to me, he was making a silent plea for help.

I always interviewed the client first to find out his or her likes and dislikes. I had a Ph.D. in psychology from the University of Chicago and had started out as a traditional therapist, helping people deal with life's slings and arrows. Early in my career, I realized what I enjoyed most was fixing troubled relationships. Later I'd become more of a life coach by helping men and women create healthy, rewarding relationships. That led to what I did now. I used my counseling experience to discover what my clients were looking for in a companion and matched them with people seeking what my client offered. The interview process normally took several hours and allowed me to develop a profile that I used when selecting a companion.

Once I had a baseline for my client, I began my search for a companion. I found my companions, both male and female, the same way anyone finds anything these days. I used the internet. I'd hired a company to design a 'dating' app that people could download for free. They filled out some basic personal information, and I used that information to make my selections. The app was only the first step. From there I selected individuals I thought might be a good fit, and after a brief phone interview, if I was still interested, I'd arrange a face to face for a more in-depth interview. I typically narrowed my interview list to between two and four potential companions during the phone interview.

Like with my client, the interviews with potential companions took several hours and allowed me to develop a profile for them. There was no science to what I did, but it should be clear to anyone that an outdoorsy adventuresome type probably wouldn't be a good fit for someone that enjoyed ballet, opera, and quiet evenings at home reading a book. It often took me anywhere from six weeks to three months to find a companion, matching people based on their personality types and my clients' desires and wishes.

Some clients were easier to match than others. Heston was proving to be more of a challenge than most, and I was running out of time. It was already the first week in February and his new boat was scheduled for delivery in the next week. He was pulling up anchor March second, companion or no.

During my interview, I realized the deal breaker for him was he was keenly interested in a woman who had her own career, who would understand the demands of his job, and finally, someone who understood he was a man driven by competition and winning. He measured himself by his financial success and his ability to make hundreds of millions of dollars in a single stock trade. If his companion wasn't equally competitive, I knew he would grind her down and lose respect for her.

What I needed and hadn't yet found was a strong, confident, woman who was at the top of her game in a highly competitive field, and she couldn't be an artist or someone who's successes couldn't be quantified. I needed a lawyer, doctor, businesswoman, or someone similar. I'd thought I'd found a perfect match, a divorce lawyer who specialized in high profile cases, but she'd turned out to be a real ball buster who took only female clients and was driven by the thrill of ruining her clients' husbands. Like Heston, I didn't have the time or desire to get into all her problems, but during the interview I realized that would have been an explosive pairing. Cooped up on a boat, they would have either hate fucked each other to death, or one would have thrown the other overboard in the middle of the ocean.

I looked through the latest applicants. Like most days, many of the applicants were people I couldn't use. My clients weren't likely to interested in a thrice divorced, three hundred-pound, mother of five barely getting by on government assistance, or an unemployed, unshaven, parolee whose idea of a good time was shot gunning beers and watching football on television while his girlfriend or wife waited on him.

After wading through and deleting more than a hundred applications, one person caught my attention. My app intentionally asked for very little information. The details of applicants' lives didn't interest me at this point, and it was natural for people to inflate themselves, so any information they might give was be suspect anyway. All I asked for was some basic information I used to weed out those who would never make the cut.

I looked Chloe up on the internet, searching for more information to give me a better idea of the woman. She was attractive, and working backwards from her credentials and graduation dates, I pegged her age somewhere around thirty. It was hard to believe someone so accomplished would have to resort to using a dating app, even mine, but at first glance she appeared to be perfect for my needs. I booted my version of the application she'd used that brought her to my attention and initiated a contact request. Chloe's phone would alert her that I wished to talk to her and asked for permission to contact her, along with a time and phone number that would be convenient for her. I hoped she would respond soon and agree to contact quickly. I was running out of time.

Chloe had signed up just last night. It wasn't often that the very person I was looking for happened to fall into my lap just when I needed her, but I wasn't going to look this gift horse in the mouth. Chloe and I were in the same time zone, so ten a.m. in Chicago was ten a.m. in Nashville. Even on a Saturday, she should be up by now.

The sounds of bare feet padding across my hardwood floor caught my attention. I looked up from my desk and smiled as my latest conquest appeared. Jacob Lanier was tall and muscled like an athlete. He was twenty-two years my junior, but that hadn't prevented him from fucking me into bliss last night. The fact he'd slept to almost ten o'clock probably meant I'd given as good as I'd gotten.

"Morning, lover," he purred. "Coming back to bed?"

He was still bed tossed and wearing nothing but his tight boxer briefs. I couldn't decide if the most attractive thing about him was his rock-hard abs or his equally hard cock. I wouldn't mind another tumble, but I was working under a tight deadline.

"Sorry, Babe, duty calls. There's orange juice in the 'fridge."

He stepped up behind me, taking my breasts into his big hands as he nuzzled my neck. "The only thing I want for breakfast is you," he rumbled, his voice low and sexy.

I let him continue for a moment. "Stop. I have work to do."

"All work and no play..." he continued in his bedroom voice.

I rose from my desk. He tried to pull me into a kiss, but I blocked him with a hand on his muscular chest. "Be a good boy, let me work now, and maybe tonight you can make me squirm again."

He backed off. "Who works on a Saturday?"

"I do."

He didn't like me giving him the brush-off. "Fine," he growled. "I need to go anyway."

"I had a good time last night," I said softly, trying to soften the blow to his ego. He'd fucked the shit out of me last night, and if he did that to most women, he probably wasn't used to getting turned down for seconds.

He smiled, but I could tell I'd never hear from him again. I was a little disappointed, but it wasn't unexpected. I'd let him pick me up because he looked like a good candidate to scratch an itch, and he hadn't disappointed.

"Okay, lover. I'll call you."

I smiled. He couldn't even remember my name. "Want to shower before you go?"

My computer dinged, and I looked at it. Chloe had accepted my request for contact. I needed Jacob to go.

"Join me?"

"Can't," I replied, nodding at my computer. "Work."

"Then no." He kissed me again, trying to draw me out, but I refused to take the offer. "I'll call," he said as our lips slowly parted. "I'll let myself out."

I didn't know how he was going to call me since I'd never given him my number, but I said nothing. I watched his ass as he walked out of the room before I turned back to my computer, picked up my phone, and dialed, mentally crossing my fingers that Chloe was the person I was looking for.

I admired the sleek lines of the Oyster 575, fifty-seven feet of pure Heaven. She'd been delivered to me only three weeks ago, and last week I'd christened her and given her a name, Trade Winds, in a nod to my occupation. She was a beautiful, capable craft in gleaming white paint and oiled teak decking. The Oyster 575 wasn't the largest sailing yacht, or the fastest, but she was big enough for my needs and was still small enough that two people could handle her with ease. Push button sailing, some called it, with large electric winches doing the heavy lifting that would allow me to sail the boat by myself if I wanted to.

The Winds, as I'd taken to calling her, was a true blue-water yacht, capable of circumnavigating the globe should I care to try. Someday I might sail her from my home base here in Miami to Europe, or if I was feeling frisky, San Diego by sailing East, but I wanted to get some experience with her first by doing some island hopping here my back yard.

I'd been sailing for over half my life. I started out in an eight-foot dingy my parents bought me for my tenth birthday. From there I'd moved up to a sixteen-foot Catalina sloop when I turned seventeen. My next stop had been a twenty-seven-foot Catalina sloop when I turned twenty-three. Hedging My Bet had been my escape, and had served me well, but for my thirtieth birthday I was replacing her with Trade Winds.

The Winds was likely my last boat. She was a beautiful craft built to the highest degree. Anything larger would require a crew to sail, which was something I didn't want. The ocean was where I went to get away from everything, and the last thing I wanted was two or three crewmembers looking to me for direction.

I hefted another of my provision boxes and stepped aboard. Since she was designed to handle the world's oceans, The Winds was a broad, stable craft. Weighing in at over sixty thousand pounds provisioned with a sixteen-foot beam, she shrugged off my added weight without a ripple in the water. I carefully made my way below deck where I lifted the floor in the galley and began to store my supplies. I was provisioning her for a month's sail, though we would likely never spend more than two or three days on the water before making port somewhere. Still, the point of this trip was to learn what The Winds was capable of, and the only way to do that was to actually do it. I'd already loaded all my perishable food. All that was left were the dried and packaged items that would wait patiently for years, if necessary, to be consumed.

I broke down the box and returned to the dock, adding the flattened cardboard to the growing pile waiting on the berth to be tossed to the recycle bin back on shore. I picked up the two cases of dried Ramen Noodles and carried them aboard. The noodles functioned as my emergency meals. They would keep forever and all that was needed to prepare them was hot water, making them perfect for a quick meal in an emergency or when I was battling the elements.

The Winds wasn't my first blue-water craft. I'd learned through experience that Mother Nature was an unforgiving bitch and to be prepared for every conceivable emergency. I carefully packed the packaged noodles into the spot I'd reserved for them, shuffling items around to get the bilge hatch closed.

"Hello?" a woman's voice called from outside.

I made some quick final adjustments to get the hatch closed and hurried out of the cabin, the two empty carboard boxes in my hands.

"May I help you?" I asked as I climbed the ladder-like steps to the deck.

"Yes, I'm looking for berth 13C. Is this it?"

The woman was about my age, a single, large, wheeled suitcase sitting on the dock beside her. She was about average in height, perhaps five-six, with raven black hair cut short in an easy-care style. She was wearing a pair of white shorts that weren't daringly short, but revealed plenty of muscular leg, along with a dark blue men's shirt that she'd tied into a knot that allowed her flat stomach to play peek-a-boo, and white canvas deck shoes. The stylish sunglasses perched on her small nose completed her look.

"You found it."

"Are you Heston?" she asked.

"I am." I stepped onto the dock and extended my hand. "Heston Mallard. You must be Chloe."

She smiled and took my hand. "That's me. Chloe Meyer. Sorry I'm so early. I flew in last night." She shrugged. "Since I was in town, I figured I might as well show up and see if I can do anything to help get ready."

I smiled. I liked her voice. It was pleasantly deep for a woman, and it had the ring of confident authority. This was a woman used to being obeyed without question. I broke down the two boxes and added them to the pile before picking up her suitcase and gesturing to The Winds in welcome.

"I'm still provisioning the boat, but welcome aboard."

She stepped onto the deck, moving carefully until she realized the boat wasn't going to wallow or move under her. "Nice boat."

I smiled to myself. She either didn't know boats or she was the master of understatement. An Oyster yacht was the Rolex of sailboats. "You sail?" I asked as I led her down the steps to belowdecks.

"No. Never been on a... Wow!" she said, her voice becoming hushed as she pushed her sunglasses up onto her head.

Her subtle exclamation of surprise and appreciation pleased me. After three weeks I was no longer in awe of The Winds, but hearing the hushed reverence in her voice reminded me of how I felt the first time I stepped aboard. I'd toured a 575 before I bought mine, of course, but it was different when it was my boat.

"This is some boat!" she gushed, looking around, taking it all in.

"Not bad. Let's get you squared away and I'll give you the tour."

I led her down the two steps to the fore cabin, placing her suitcase on the bed. "This is your berth." I began opening doors and panels, showing her where everything was. "This is your closet, with more storage down here," I said, raising the floor to access the bilge. "All doors and cabinets are locked, so you'll have to release the catch to open them," I explained, showing her how to release the locks that prevented items from flying around in heavy seas. "Don't leave anything unsecured, ever. Not only is it bad seamanship, you'll spend all your time looking for your stuff if we get into heavy seas."

She nodded in understanding as I opened another door. "Your head, with shower." I squeezed past her after she looked into the small room and opened another door in the hall opposite her head. "Stowage," I explained, stepping aside so she could peek inside.

The stowage room normally functioned as a small cabin, but I'd had the boat outfitted for maximum seakeeping and was using the room for storing spare parts and other emergency supplies, which meant The Winds had only the main and guest cabins fore and aft with the two small crew cabins refitted to serve other purposes. I led her back to the main cabin.

"Hand holds," I said, grabbing one of two chrome bars that ran along the ceiling and throughout the boat, and pulled my feet off the floor to show her they were plenty strong to use. "This is the common area," I said, sweeping my hand around, taking in the room.

The common area was the width of the boat and occupied about a third of her length. I led Chloe around a wall. "Galley with all the amenities."

She looked around, her eyes wide. She probably thought she was signing up for a trip in a dark, dank, windowless ship like she saw in pirate movies, not the bright and sunny cabin with air conditioning, television, engineered stone countertops, dishwasher, refrigerator, microwave, and windows everywhere.

We stepped out of the galley and paused at a small desk with a large GPS screen, redundant radios, satellite phone, a couple of monitors, and large panel of buttons and switches mounted in a wall that controlled the functions of the boat. "Chart table. Behind there is my office," I said, opening the door on one side of the steps into what was once the second, smaller, crew berth that now served as my office.

I allowed her to look. Inside the small room was a narrow desk, with a laptop securely attached, a duplicate of the satellite phone found at the chart table, and a chair. After she turned away, I led her around the steps that led to the deck, down two steps, and along a short hall.

"Finally, the master suite."

I stepped aside so she could look around. While the common area was in the widest part of the boat, the space was shared by the galley and the relaxation area, but here, in aft of the boat, the entire width was devoted to the suite. The room had a large closet with a private head opposite. With only two cabins, the forward head was for all purposes private, but it was intended as the public head for the entire boat.

"This is amazing!" she whispered.

"I like it. I still have some things to do before we're ready to get underway, if you'd like to unpack. Please, make yourself at home."

I followed her out of my suite as she made her way forward. I watched a moment, admiring the way her ass moved, before climbing the steps back to the deck. On the dock, I picked up the old wine case piled with spices and carried them aboard. I was still putting the spices away when Chloe appeared.

"Anything I can do to help?"

"There's one more box of supplies on the dock, if you want to get that."

She nodded and disappeared up the steps. "God... damn!" I muttered softly as I watched her ass disappear through the hatch. A moment later she appeared again, moving carefully down the steps, the box in her hands. "Just set it on the counter," I said with a nod. This was my boat and I wanted to put stuff away where I wanted it.