The Yacht Competition
Sly and I were enjoying a peaceful meal at a stylish eatery near my recently acquired flat. He often persuades me for a dinner date about once a week or so. It started as a way for us to unwind and foster a deeper bond; a better location than his place, where cleanliness and organization are secondary to a client's comfort. Despite our contrasting upbringings - him being a street-smart thug while I'm a sheltered "princess," to use his words - we share a deep mutual respect.
When I first proposed the weekly dinners, I was astonished to learn that Sly had never indulged in a formal date! Apparently, in his world, people simply came together, indulged in their preferred activities, and then went their separate ways. I needed to convince him that dinner could be both enjoyable and non-sexual. Much to my surprise, he's progressively adapted to this idea, if reluctantly.
One Sunday morning, over a cup of coffee, Sly enquired about my knowledge of boats.
"What kind of boats? Cruise ships, rowboats?" I asked in confusion.
"No, Princess. You know, sailboats. Yachts is what they're called," Sly replied with a snigger at the extravagance of those who could afford to own yachts.
"I've ridden on some yachts in my family's circles," I said, recalling my experiences with my friends. They’d often host races, social events, and the occasional voyage.
Sly's tone dripped with disdain, "I guess that makes sense. Anyhow, one of my clients owns a yacht. He likes to race every weekend. He wants to outclass other rich folks with these supermodels around on his yacht. While most of them bring their own eye candy, he's having a hard time acquiring a fitting lady. He has the money, though."
Curious, I asked how this was connected to me.
"Well, he wants a gorgeous, sexy woman to represent him. Sure, he's paying enough, but that's not part of the agreement," Sly responded.
I appreciated the compliment - I understood he was referring to my looks objectively, not personally. However, the notion of a fun outing without adhering to any restrictions sparked my interest.
I arrived at the yacht club on the following Sunday at around eleven o'clock. I'd worn an outfit that embraced my long legs and complemented my body. A pair of sleek, white short shorts, Sperry Topsider boat moccasins, a revealing red tie-front halter that highlighted my abs and accentuated my chest. My hair was tied in a ponytail, bound with a matching red ribbon. I'd made subtle touches to my makeup - 'sufficiently sexy' being the aim.
As I approached a table by the waterfront, where four men sat consuming beer, I inquired, "Excuse me, am I able to find Carter Williams here?"
Their conversation came to a standstill. Several pairs of eyes examined my attire intently.
"Um, are you referring to Carter Williams?" one of them asked, disbelief in his voice.
"Yes. I'm here to serve as crew for him later in the day," I answered, growing impatient with their lingering gaze.
They glanced at one another, silently sharing their perceptions.
"Sorry, ma'am. Carter is docked at the A pier. His yacht is called Mistral," one of them finally replied, their curiosity somewhat calmed.
Appreciating their attention, I walked to the A dock. They seemed to be keeping tabs on me, almost tracking my every move. I figured since I was being compensated for being a stunning sight, I'd give them something to gossip about, so I amped up my flirtatious behavior, which was quite natural in those tight shorts. A light murmur of their chatter entered my ears.
Question: What lady doesn't relish making a grand entrance?
Mistral was a stunner, although I couldn't exactly say the same for Carter. She was a stunning Shannon 38 cutter-rigged ketch with a black hull and white superstructure and abundant polished teak. He, on the other hand, seemed unremarkable, even though nothing about him was catastrophic. She was designed to look great but lacked speed. He was made to ... well, I'd learn more about that later. In any case, one person was in charge of the lovely boat if he wanted me to serve as decoration.
"Carter Williams?" I inquired from the dock.
He had been watching me as I got closer. His mouth gaped wider and wider. He must have thought he was witnessing a mirage.
"Um, I...ah, Vicki?"
"Aye, Captain. Permission to board?"
A moment of silence ensued. His gaze was stuck on me.
"Captain Williams, sir?"
"Oh. Oh my! I'm sorry. Yes, please. Board the ship!"
He welcomed me at the midships companionway and held out his hand to assist me aboard.
We settled into the cockpit as he said, "Vicki, dear, you're more stunning than your agent could ever describe. Oh, did you chance upon the clubhouse on your way here? Did anyone see you?"
"I bumping into a few gents. Who knows? I might have left a lasting impression on them, if that's the question."
"Great! If that's the case. You're a keeper!"
He studied me like a scientist examining a specimen.
"I'm guessing you have little experience in sailing. Can you assist?"
I chuckled. "I've crewed before. Help's always welcome. Let me know what you need."
His face had a marveled look. "Incredible! You excel way beyond my expectations. So, let's... oh, we need to reach the starting line by 1:00 PM."
He ignited the diesel, and I hopped back onto the dock to undo the lines. I stood up, bent over while doing so, allowing him to enjoy the view. What can I say? He was paying for this. I hopped back on, and we were underway.
When we sailed in open waters, Carter handed me the helm, accompanied by a quizzical expression. I just smiled and steered us into the wind while he raised the mainsail and mizzen and unfurled the jib and staysail. I brought us about and caught the wind, then handed the helm back to him. Despite not being a speedster, she was still a stunning sight close-hauled. Carter's eyes kept dilating as I navigated, handling ropes confidently, even as the boat tilted roughly a twenty-degree angle, her leeward gunwale nearing flooded.
I couldn't help but giggle with pride. Guys seem to be thunderstruck when they discover that attractive women can prove skilled as well. I find immense gratification in shattering their shortsighted assumptions.
On a "downwind stretch," I sauntered towards the galley and prepared dark and stormies for us both (he did, indeed, have Goslings rum and Goslings ginger beer and an ample stock of lemons. Dweeb he might be, but he stocked a well-stocked bar.). We settled into the cockpit and simply enjoyed the peaceful waters. I had to remind myself that I was on the payroll.
Carter turned out to be a fellow of decent character. His pedigree had instilled in him the belief that women were seeking his fortune, leading to limited exposure to them. He could unwind around me, though, since our deal was strictly business. And so, we conversed as we prepared for the race. I'm a good listener: an asset in my occupation. I discovered I was taking a liking to the guy.
Though we didn't win the race, we managed not to disgrace ourselves.
Upon arriving at the dock, I couldn't resist demonstrating my sailing abilities. I jumped to the pier, tied the boat up using a one-handed looping and tying off of the ropes to the cleats, all while remaining standing, a technique I'd learned as a teen from a dockworker anxious to charm me (he did.).
After docking, I decided to embellish Carter's ego a little; after all, I was in a delightful mood. I jumped back onto the Mistral.
"We should head towards the clubhouse," Carter said. "We should applaud the victors and listen to their gloating." [2]
1: The context of these lines is that she didn't win the race, and she walked down to the clubhouse to hear everyone talking about the winners.
[2]: The context of these lines is that he's asking her to accompany him to the clubhouse, where they can mingle with others and celebrate the end of the race.
"Carter," I said, "I didn't really have a chance to explore down below on the ship. Mistral is stunning above deck, and I'm sure she's just as impressive below. Can you show me around? You've got all the time in the world. They'll be arguing over adjustments for PHRFs and reenacting every single maneuver twice. The nonsense will still be there when we return."
He looked at me questioningly and said, "Sure."
He led the way down the stairs to the lower deck. I hadn't had a chance to properly observe before. The cabin was stunning. Masterfully crafted with lots of teak, mahogany, and brass.
"Wow," I exclaimed. "But I'm more interested in checking out the V-birth."
He eyes scanned my face for a clue, but I'm quite good at acting. He turned and led the way forward.
As soon as he got through the door to the V-birth, I moved close behind him, grabbed his belt buckle.
He turned to face me.
"Vicki, I didn't... I mean, we had an agreement..."
"Hush," I said calmly. "Looks like you've got a rebellion on your hands, Captain."
I unbuckled his belt, backing him up into the berth. He fell backward. I pulled his shorts down and off his legs, leaving him only in his underwear. To give him a helping hand, I untied the front of my blouse and pulled it off. Next, I unsnapped my bra and tossed it away. His eyes were glued on my chest. His erection was growing rapidly. I took off my shorts and thong.
I leaned down and stroked the outline of his cock. He gasped.
"Very nice," I praised. "Are you feeling good?"
"Oh, God, yes," he panted out softly. "You know, you aren't supposed..."
"Shh, my love. This mutiny might be enjoyable for you. Just relax and enjoy it."
I took hold of his shorts at the waistband and pulled. With some hesitation, he lifted up his hips, and I pulled his pants off his legs. His cock stood at full attention. I stroked it gently with my fingertips and it throbbed and produced a drop of pre-cum. His breathing was noticeably quickening.
I bent over him, taking his pre-cum with my tongue. I kissed the head of his cock and then took it into my mouth, sucking on it a couple of times. He tasted fantastic. His breathing was getting faster.
I rolled onto my back, inviting him into the berth. He moved up, so that my breasts were aligned with his head. Without hesitation, he began to kiss my breasts. My nipples responded, hardening instantly. Poor guy seemed expecting more resistance, but I didn't really care.
I guided him to my pussy with my legs spread open. His warm fingers caressed my pussy, making me wetter still. I felt his hand moving slowly, teasing me more.
He mounted up, his cock pressing against my awaiting entrance. I spread my legs wider, to indicate that I was ready. He slowly pushed into me, giving me the pleasurable feeling of being full. Reveling in the warmth and rhythm of his cock, I turned my face to meet his, kissing him fiercely.
He began to fuck me, slowly and smoothly. He didn't rush. He took his time, presenting me with long and gentle strokes. His rhythm picked up, but not too quickly. This gentle pace made our breaths heavy.
I could feel his cock get harder, and knew he was getting close to climax. He thrust deep inside me, held there, and shot his load into me. I climaxed a short while later, my back arching and moans of pleasure escaping my lips.
We lay there, sweaty and spent, exhausted from our intense lovemaking. Eventually, he moved away, and pulled out of my wet vagina. In a moment of afterthought, I gripped his softening penis with my hand. [End of text.]
"Wow, Vicki, that was amazing," he exclaimed in awe. "You're so smart, beautiful, sensual, an outstanding sailor, and a fantastic partner. Will you marry me, please?"
I grinned.
"Shouldn't we head back to the clubhouse?" I inquired. "They're likely to be concerned about our whereabouts."
"Nah, I highly doubt they'll be too preoccupied. They've probably already discussed our whereabouts in great detail. Perfect! Watch me revel in their jealous stares for a while."
We got dressed and returned to the clubhouse. I savored the reactions of the men as they greeted Carter. I felt content, knowing I'd earned my money while having a fantastic day.
I love this work!
