Pirates!!

Sly was suffering stoically from a miserable cold.

Of course he, being a big, tough, raised-in-the-streets male, it was impossible for him to admit it. So he sat amid a crumpled mess of Kleenexes, staring at me through red, watery eyes.

"Are you taking anything for that?" I asked, knowing full well what the answer would be.

"What, this? Fuck no. It'll go away by itself. I just gotta outlast it."

"Can I get you some Coricidin, or maybe make you some tea with lemon?"

"Ain't got no tea. Don't need no medicine."

"Fine. More Kleenexes, then." I really felt sorry for the big guy.

"Princess, will you for Christ's sake just shut the fuck up! Let it go, for God's sake."

I shut up. Thing is, I really did want to help him. I mean, he's been good to me ever since we became partners. I know, that'll sound strange if I've never told you the back story. After all, he mocked my upper-class background, sarcastically calling me a princess, and then blackmailed me into having sex with him and later with several strangers. But when I had paid off my debt we both realized that I was damned good at it, and, after he made me face up to that fact and that I rather enjoyed it, he offered to partner up, with him getting clients and me satisfying them. Yeah, I know there's a word for that, but I insist that we always refer to him as my 'agent' and our clients as 'clients.'

I consider myself a professional, after all. And I I've kept my job as a copy editor for a very respectable law firm in the city. I love the secrecy and adventure of my night job; it makes the tedium of the day one more bearable.

Oh, and he still calls me Princess, but I've earned his rarely given respect, so it's just a name, now. I like it.

"All right, all right," I reluctantly said. "Suffer, then."

"Better. Look, I ain't just been sittin' here, Princess. I got somethin' lined up for you that I'm bettin' you're gonna like. It'll appeal to your screwball sense of adventure. Plus, it's worth a nice chunk of change, and things have been a little lean lately."

Sly knows me pretty well. Having been involved in the sex trade before, he has a remarkably practical empirical sense of women. He can tell when I'm getting a little stale. He's exceptionally good at handling me, and I don't really mind it, so long as I'm aware of it. Besides, I know his concern is genuine and for me, not just for what I can do for him.

There was a pause while he blew his nose.

"Pirates," he said when he'd recovered.

"Pirates," I dumbly repeated. "What about pirates? There's all kinds of pirates. Remember, I work for a law firm."

"Jesus," he said in exasperation. "What do ya think I mean. Sex-mad software pirates? Horny music pirates? C'mon, Princess."

"OH-kay, enlighten me then, agent mine. What's this between me and pirates?"

"Bunch of spoiled rich bastards, wanna spice up their tired little sex lives. They pretend to be pirates. Like little kids, but with sex."

"Which is where I come in," I said. "Sounds intriguing. Do go on."

"Not much more to tell. They need women to dress up like pirate wenches and be accessible."

"Hmm. I haven't been a wench since the opera job. That was fun. Okay, I'll do it. Set it up."

"Yeah. That's my girl."

"You're supposed to say 'Aye, me pretty.'"

"Fuck."

Hopeless.

I love the city. You can find anything, including sexy pirate wench outfits. I went with a frilly white low-cut peasant blouse, cinched at the waist with a red sash and broad black leather belt that uplifted my breasts and deepened my cleavage. Over that I wore a long, open black leather vest that hugged my waist and flared out over my hips. The short red skirt had a slit up to my thigh on the right, giving tantalizing views of my long legs, which I sheathed in dark stockings and knee-high, high-heeled, shiny black boots. I topped it all off with a broad-brimmed hat with a big feather stuck in it, and wore my long hair down. Heavy on the eye makeup and red lipstick, too, and I was ready to go a-buccaneering for fun and profit.

I was able to get Peter, my favorite Uber driver. Peter has seen me in all manner of outfits and going to strange addresses, so he no longer expresses any surprise when he picks me up. We usually chat about his family. I also like that he's never made a pass at me or expressed any judgement about what I'm sure he realizes that I do. Nice guy, Peter.

He delivered me to the address Sly had given me. I took the elevator up and knocked on the appropriate door. The peephole opened and an eye checked me out.

"Am I at the right place?" I asked in all innocence.

"Aye, me pretty," came the voice from within.

Take that, Sly.

The door opened. I don't know if the original pirates knew about pot, but this place reeked of it. It was dimly lit, but I could make out a dozen or so people, both men and women. They were all dressed as pirates; no surprise there. I had to admire some of the costumes. They were pretty elegant. I doubt that real pirates could have afforded most of them unless they'd just sacked a Spanish galleon full of gold. There were a few eye patches and a parrot or two. A couple of the swords looked all too real for my taste. Screwing up my courage, and burnishing my accent, I entered.

I was immediately greeted by two guys. One took me by my shoulder and turned me to face him.

"Arrr," he said. "What have we here? 'Tis a comely wench, I'll warrant. By what are ye called, me darlin'?"

I smiled. "In Port Royal them as has gold calls me Mistress Vicki. With an i. Them as doesn't have gold I don't talk to. Them as bothers me don't talk any more." I had done my research on pirate havens, you see.

"I be Cap'n Mark. I be the gatekeeper here. By the looks of ye, ye are of the brethren and are welcome. So, Mistress Vicki, 'tis gold you like? Well then, 'tis gold you'll have, me darlin'. Welcome aboard!"

They were quite good looking and quite dashing in their pirate outfits. I have to say, guys in the nineteenth century really knew how to dress romantically. This was already beginning to look promising.

It didn't take long after that. Several men approached me and gathered around me.

One of them put his arm around my waist. He cupped my chin and lifted my face to him.

"Ye are a rare beauty," he said, his face close to mine. "By what are ye called?"

Hmm. This dialog was beginning to sound familiar.

"Ye may call me Vicki," I said. "With an i."

"Well then, Mistress Vicki, I would bed thee."

No beating around the bush here!

"Oh? And what pray tell would ye have to offer me for my favors?" I figured, what the hell, I'd play the game. I was getting well paid for it.

He was taken aback only for a second.

"Come with me and I'll show ye," he said. "I warrant ye'll not regret it."

I liked this guy! He was handsome in his outfit and certainly had self-confidence. I smiled and took his hand. He led me to a separate room. It was decked out like the captain's cabin on an old sailing ship, complete with a span of fake windows that appeared to look out on an eighteenth-century harbor somewhere in the Caribbean. The illusion was excellent, but neither of us spent time admiring it.

The captain's bunk, however, was thoroughly modern and comfortable looking.

We wasted no time. We were barely through the door when he lifted my hat off, threw it aside, and ran his fingers through my hair, loosening it around my shoulders. He had the door closed and was at the buttons of my blouse before I'd finished looking around the cabin. I'm always flattered by guys' urgency, but sometimes I do wish they'd practice a little patience.

He was obviously pleased to find that I wasn't wearing a bra, in keeping with the period costume. His eyes lit up when my breasts were exposed. My nipples responded by standing up at attention for his inspection. He leaned down and kissed each one, taking his time, running his tongue gently over the areolas and nipping them playfully. My breath caught. His hands explored under my skirt and cupped my ass. I put my own hands behind his head and encouraged his exploration of my breasts. This was getting better by the minute.

He slipped my vest off and then my blouse. I unsnapped my skirt and let it fall. At that he lifted me with his arms behind my shoulders and knees and carried me to the bed, kissing my mouth and breasts as he did. God, I wanted to yield to him!

He set me down gently on the bed and pushed my shoulders back until I was lying there, clad only in panties, stockings and boots. I gave him my most inviting look and reached for him with my arms.

His pirate costume came off easily, parts of it thrown carelessly to the floor. His shorts were beautifully tented and showed a promising dark spot where his pre-cum had soaked through.

The shorts came off and revealed a lovely big cock, fully inflated and throbbing with life. Lord, I wanted it in me. My hips began to sway involuntarily. I could feel my pussy milking. My swollen breasts ached in a very erotic way.

"Take me, my captain!" I breathed. "I am your wench to do with as you please."

He grasped the elastic band of my panties and had them off over my boots in one smooth motion. He gently spread my legs and knelt between them, and then I felt that warm blunt cock pressing against my vaginal lips, parting them. We were both so lubricated that my lips yielded easily to his pressure, and he probed into me. We both sighed with relief once he was safely inside me.

He kept on penetrating me, deeper and deeper until I could feel the tip of his cock press against my cervix and our hips met.

I moaned.

"Oh my God, you feel so good!" he breathed. All pretense of the pirate accent was gone, now. He was now a thoroughly modern man fucking a thoroughly modern woman for all both of them were worth.

His strong hands pinned my shoulders, and he rose up on his hands and knees, taking the pressure off my chest and allowing him to rise and plunge. With each stroke his marvelous cock slid deep into me and withdrew with a wonderful sucking feeling in my highly sensitive vagina. I used all my perineal muscles to grasp that great instrument as tightly as I could.

I really liked the way he varied his rhythm and depth. Sometimes he would just keep a few inches into me and rock back and forth, concentrating on rubbing my clit. Then he might move just a little in and out at a rapid pace. A moment later he'd go much deeper and slower. It was raising me to new heights! He was playing me like a fine Stradivarius, and I responded with pleasure.

Both of us were moaning and gasping in our mutual passion. I wanted it to last forever, but my body had other ideas. I felt that magical fire start in my loins and begin to spread over my belly, up into my breasts and down my legs. I think I cried out. My eyes were closed, and my head was rocking from side to side. The world outside my body disappeared in a pleasant pink haze. I felt myself spurting and heard him groan and then felt him go deeper than ever into me. Our hips locked and he held me close while he released into me, again and again. It was wonderful! His cock took on a new life, throbbing and spurting, filling me with his warm semen. I could feel our mixed fluids running down my inner thighs.

After an eternity spent in a faraway place I reluctantly returned and opened my eyes. I looked up at him. He was smiling from ear to ear.

"Jesus, Vicki," he said quietly. "If this pirate stuff were real I swear I'd make you the toast of the Caribbean. You are one amazing wench."

"'tis me pleasure, Cap'n," I said, returning to the scenario. We both smiled. "But perhaps you'd best take your leave now."

"Oh God. Sorry," he said. "I just was enjoying the feel of you."

He gradually withdrew his deflating cock. Even wet and partially shrunk it looked rather good. I was tempted to invite a rematch. But I was getting paid to be a lascivious wench and there were other pirates around.

Before he left, though, he reached for his wallet and took out a hefty wad of bills. He turned to me.

"I know you've already been taken care of," he said, "but please, take this from me. You've made this an evening I'll never forget."

"Thank you," I said, taking the extra money. Hey, a girl always enjoys a compliment, and if it's accompanied by something more tangible, so much the better.

He hesitated.

"And.... Maybe I could see you again?" He had the cutest appealing smile.

"Yes," I said. I'd like that." And I meant it. "You'll know where to find me."

A quick kiss and he was gone.

God, I love this job!! Arrrr!