The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that bulged everywhere. He towered over every other man I have ever seen and he was not a kind man at any time. He had his way, all the time.

For me Captain Booth had chosen the path of the fuck toy. I was to be dressed at all times in what he had picked out for me to wear. These were the finest feminine garments in the world, the riches of the many ships he had plundered. I dressed in the most beautiful dresses and lingerie the world had to offer. Captain Booth's favorite was a blue and lavender dress with white lace trim with a pearl-white corset with garters that hooked to my sheer stockings underneath. I always had to wear at least two-inch high heels yet I still had to stretch up on my tiptoes to kiss my captor. I had makeup that I wore to make myself even prettier. I had some perfumes that I dabbed about my body to drive my master wild with lust and I kept myself clean and ready for my master’s fingers, tongue and cock. I also had some erotic oil that I used inside me that served as a lubricant, masked unpleasant odors and also heated up my rectum with an aching burn, making me crazy for cock. I also made sure my own tiny cock was tied up and out of the way, as Captain Booth did not like it and had threatened to remove it numerous times.

Captain Booth had been away on one of his lieutenant’s ships, the Sabre, for several weeks plundering the high seas. After months of this he finally made his way back to the Black Bess. I heard the shouts of the crewmen that he was back and knew I only had a few minutes before he would be inside me. I quickly removed my gown so I was down to just my corset and stockings and added a light squirt of pleasure oil, then went to stand near his bed to await his arrival.

After boarding, he shouted a few quick orders to his first mate, a huge African named Mumbaso. Then the door to his cabin opened and my lover was back. He saw me, framed against the windows of his cabin in the moonlight, with nothing on but my pretty lingerie and he growled. He was on me in two strides and grabbed me into his massive arms to roughly plant his mouth over mine. His tongue drilled into my mouth, to the back of my throat and I was suddenly overcome by his overpowering scent. The smell of his manliness weakened my knees and I collapsed into his embrace. His fingers found my pussy and he pushed his probing digits inside me, even as we kissed. He picked me up effortlessly and threw me upon his bunk. He was removing his shirt as I caught site of his throbbing erection and gasped. Although I had had the captain inside me many times before, I never ceased to be amazed at the length and girth of his impressive cock, especially in light of how horny I was and how long it had been since our last time together. In seconds his clothes were removed and he was back on top of me, crushing me between his muscled body and the mattress.

His hands ran up and down my legs and I knew from his response that he found my choice of my silkiest silk stockings perfect. I moaned into his mouth as he continued his forceful kissing. Captain Booth normally enjoys eating my pussy for a while before he takes me, but I could tell that this time there would be little foreplay. He hooked my knees up over his shoulders, exposing my hungry hole. With one mighty thrust he was in me to the hilt and I felt my insides trying to adjust. I put my hands on his chiseled, tattooed chest and he settled into his fuck. I stared up at my lover as he closed his eyes, threw his head back and hammer-fucked me, desperate with need after weeks of absence. I started to cry out in short, high-pitched squeals, begging for my master to fuck me harder as I buried my finely manicured fingernails into the muscles of his back and wrapped my thighs around his hips. His big rough hands alternated between cupping my round buttocks and running up and down my stocking-clad thighs and calves, all the while continuing his reckless, forceful attack into my tight boy pussy. My own cock was pressed between our bodies, the friction building a pressure in my balls. It was impossible to ignore even with my prick tied with a silk ribbon. I was going to explode. I became acutely aware that my tiny nipples, having been released from my corset, were rock hard as well and were rubbing against Booth's hard muscle-bound chest every time he thrust into me.

The arousal proved too much for my 18-year old body and I came hard. My cum splashed upon my tummy and splattered Booth’s already sweat-soaked torso.I screamed out in pleasure, digging my nails deeper into his muscled back. At the same time my hole clamped down on the captain’s powerful cock, trying to milk the spunk from his balls.

I felt his hands slide from my cheeks and take a tight grip on the sheets on either side of us. He was fighting against cumming quicker than he wanted but he soon let loose with a loud roar as he slammed forward one last time filling me completely with his seed.

I was trembling and moaning quietly with passion as he unhooked my legs from around his waist and slowly withdrew his length from my gaping hole. My stretched rectum was filled with his cum as he pulled free. We were both gasping for breath, the musky tang of sex hanging in the air as we unwound. I knew it will only be a matter of minutes before the captain was ready for another go. He pulled me in to spoon and I felt his limp manhood lying behind my rear, just inches from my now well-lubed hole. He murmured in my ear sweet nothings about missing me and how pretty I looked. His hands were roving over me, touching me in places where only he has been. Behind me, I felt the beast stirring, coming back to arousal. I had but a few minutes before he would be penetrating me again, but I was so tired I drifted into a light doze.

I snapped awake to the feeling of the captain tweaking my nipples. It was intensely erotic and sent shivers up and down my spine. I could also feel the captain’s once-again throbbing erection poking into my boy-pussy from behind. My own boner jumped up immediately. I loved being taken in this position, because my captain could pull my pussy lips apart and really thrust in deep, hitting all the spots that push me into orgasm. He did just that. As one hand pulled my ass open, the fingers on his other hand were busy pushing into me, delving into me deeply. I shifted myself to push back on his hand, letting him know that I was very awake. I heard him chuckle in the darkness; he always loved the reaction he got from me. He once told me that there was no greater pleasure in the world than taking a young lad who thinks he’s a ladies man and turning him into a cock-craving, pussy-boy whore. That certainly described me.

I groaned lustfully as I felt the nudge of his cock head on my beckoning cunt lips, the captain’s strong, calloused hands holding my buttocks open, allowing him access to my body’s most intimate region. With one of my hands gripping his wrist and the other grabbing the sweat-soaked sheets, he thrust forward with a mighty push, his shaft sliding into my guts, deep, deeper than I could ever have imagined it was possible for someone to go and I let loose a scream. A scream that was equal parts pain, pleasure, and pure lust for my black lover to once again stake his claim to my body. I pushed back hard as he pounded forward and I felt his hands running up and down my garters sliding a finger inside the top of my stocking and feeling my smooth skin underneath. He loved me clad in lingerie and it turned him into a raging sex brute when I modeled the expensive hosiery, garter belts, bras, corsets, gowns and panties his crew has plundered from captured vessels. But I loved it as well, loved becoming his sissy and surrendering to his desires.

He was hammering into me so hard it was all I could do to gasp out little mewls of pleasure, begging him to fuck me harder, faster, deeper. He complied and I felt him going even deeper. I heard him grunting, growling as he approached orgasm. If the crew did not already have a clue what was going on, now they would. Our screams and groans of ecstasy were echoing off the walls of the tiny cabin. Soon he rolled over on me so my buns were sticking straight up in the air and he could get total leverage to power fuck me, to dominate his sissy boy. And dominate me he did. I looked around on either side of me, and could see nothing but sweat-covered, well- muscled ebony arms with hands gripping tightly the silk sheets beneath us. I prepared for my master’s fuck. He started with a slow, deep, sexy rhythm that graduated to a hard, fierce, shallow stabbing as he hit my pleasure nub multiple times. I shot my boy load below me, filled with sexual delight, a feeling that can only be known by those who have been fucked by a dominating black stud. My pussy muscles tightened around my lover’s tool, trying desperately to milk all of the cum from his balls. With one final plunge, my hard, black brute blasted another huge, creamy load deep inside me. I let loose with a girlish scream feeling him first pump several shots into my boy womb and then feeling the scalding heat of yet more of his cum hitting my round, upturned buttocks as he pulled out of me completely, his glistening erection still spraying molten sperm.

He was breathing hard, practically gasping to draw a breath as he collapsed next to me on the crumpled sheets, which were now drenched with sweat and cum and the musky scent of sex. He reached out to cover my butt cheeks with his free hand and I felt a finger gently poking in, swirling around in the remnants of his sticky man juice that slowly bubbled out of my wide-open quim. I was Sissy and I belonged to Captain Booth.