A Pirate Looks at Forty

by Cynthia Trusscot

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© Copyright 2014 - Cynthia Trusscot - Used by permission

Storycodes: M/f; bond; rope; gag; captive; strip; exhib; tease; sex; climax; cons; X

NB: For those that might not know, the title is a song by Jimmy Buffett

“I’m forty,” she said, taking a sip from her martini. I doubted it--I thought fifty was a better estimate. But she had a nice smile, a lot of dark hair, a good figure displayed by a low cut, skintight dress, a friendly attitude, and we’d had some pleasant conversation, so it didn’t matter.

“Well,” I said, “It’s a good thing I’m a pirate.”

“You are? Why is it good thing?”

“A Pirate Looks At Forty.” She laughed. Nice laugh. “Do you have a pirate ship?”

“Yes, I do, actually,” I said. “D’you want to see it?”

“Only if I can be a captive on it,” she said, giving me A Look. I paused for a minute, then decided to take her at her word and see what happened.

“All right. Turn around, and put your hands behind you.”

“Why?” she asked, suspiciously.

“So I can make you my captive,” I said. I took a piece of line I happened to have from my jacket pocket. With a sexy little smile, she did as I asked. I tied her hands behind her back.

“How’s that? Not too tight?”

“Err, no,” she said. “What is this for?”

“You’re my captive, and I’m not taking any chances with you,” I said. “Besides, the barman has seen you acquiesce to being tied, so he knows you’re OK with it.” Suddenly the bartop needed considerable polishing. She smiled, and turned to him.

“Oh, barkeeper, dear – Do you have a clean bar towel?” He did, and handed it to me.

“What’s that for?” I asked.

“Do you put up with loud-mouthed women?” she asked sweetly. I tore a strip off the towel and tied it through her pretty mouth.

We left the Yacht Club bar. I led my pretty captive, gagged, her hands tied, down the harbor side path. Her high heels sounded on the planks as we went down the pier. It was a bit awkward maneuvering a woman in a tight dress and high heels onto my dingy, then up into my boat, especially with her hands tied, but we managed it. Shortly I had her sitting on my quarter berth. Sailors always have line available, and in a moment I had her ankles and legs bound. Then I took out the gag.

“This is very nice!” she said, looking around the saloon of my boat. Tip: Always complement a sailor’s boat. “Piracy must pay pretty well.” I explained that I was one of those finance people who makes a living by pillaging companies and calling it ‘reorganization’.

“So you really are a pirate!” she exclaimed.

“Yes,” I said, “And you really are my captive.” I sat next to her on the settee, and pulled her to me. “You can’t push me away, or fend off my advances, “ I said as I gave her a thorough kiss, then gently cupped her breast. She purred. “And,” I added archly, “There’s no escaping for you. You’ll never see England again, my pretty, Arrr!”

“That’s all right, I’m Italian,” she said. “I wasn’t planning on escaping, but you should probably keep me tied, in any case.” She extended her bound legs and moved her feet up and down a bit, showing off her pumps. It was a nice sight, white rope, sheer dark nylon and shiny black leather. “I’m enjoying the feel of this—of being tied up. It’s quite – erotic. Wouldn't it be more authentic if I were tied to the mast?”

“That sounds like a good idea,” I replied. Helping her up, I maneuvered her over to where the mast came through the saloon. In a moment I had her tightly bound to it. She looked wonderful, her short dress riding up her thighs, white ropes encircling her body and legs.

“Are you fond of this dress?” I asked.

“N-not particularly,” she answered, “Why?” Her eyes widened when I opened my knife and pointed it towards her throat, but she relaxed when I only cut the shoulder straps. The loosened dress fell to the deck. Black lace bras are replaceable, so I had no compunction about cutting hers off. It added verisimilitude to the pirate act. Pretty breasts glowed in my cabin lights. I kissed each one, then her throat, her eyes, her full lips. She made little pleasurable noises.

I stepped back, and began to remove my clothing. She stood, tied and helpless, watching each revelation. When I was down to my skivvies, her eyes widened. “I see that this isn't the only mast on this boat.”

“It is a ketch.”

“That isn’t what I meant.”

“I know. Maybe I should blindfold you.”

“Not in your life,” she said, “But I think you should put the gag back.” I did, then squeezed her breasts again. She moaned, and twisted against the ropes binding her. I bent down and untied her legs, which she obediently spread wide for me. Wearing heels, she was the perfect height.

When morning came, we were in the master cabin. She was still tied, loosely, her hands in front of her. I kissed her. “Good Morning, captive.”

“Good morning, Captain,” she answered contentedly. “Do I get to walk the plank this morning?”

“Sorry, what?”

“Don't ruthless pirates make their captives walk the plank?”

“I hadn’t thought of it but I suppose yes, they do.”

“Goody. Lead me to your plank, you cruel pirate.”

After breakfast I rigged a plank I had out over the side of my boat that faced the beach. She stood watching, wearing her panties, stockings and heels, her hands re-tied behind her. “Are you sure you want to do this?” I asked.

“Oh, yes. It’s only a couple hundred meters, and that's my cabana right there,” she indicated with a nod of her head, unable to point with tied hands.

When all was ready, I gave her a long, sweet kiss good bye, tied a blindfold over her gorgeous eyes, and helped her up onto the plank.

“Now walk, my pretty! Arrr!” I snarled. Blindfold, her hands tied, she inched her way out onto the plank. Giggling, she swayed a couple of times as the boat moved under her, struggling to maintain balance in high heels with her hands tied behind her back. She managed to make it a meter and a half before she lurched, staggered, then toppled off the side of the plank.


I was only a moment later when she surfaced, laughing, Her hands had only been loosely bound, and she freed herself, removed the blindfold and threw them at me. Then she turned and swam energetically towards the beach, emerging from the water like a goddess and running through the sand. She turned and blew me a kiss, then sprinted, half nude, to her room, giving some old geezer a heart attack as she flew by.

Later, I returned her mended dress, purse, and a new black bra to her cabana. In return, I received a pretty souvenir: A skull-and-crossbones flag. I flew it from my starboard shroud when I cleared the harbor that afternoon.

The End

NOTE: The author, who is a sailor, wants it understood that this story is fantasy, and that almost everything, from taking a strange lady captive in public to making her walk the plank is too dangerous to do for real.

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