I was the daughter of an English Colonel stationed in the British West Indies. My mother and I were going with him, most likely never to return to Mother England.
Unfortunately, my mother got ill on the voyage, passing away before we arrived. I was a mere child of five and didn't understand why, if there were a God why he'd take her away from us.
My father was to be the commanding officer of the garrison stationed in the Cayman Islands. He knew the army and how to train men, but he knew very little about taking care of a small child, let alone a female one. Fortunately, the ladies of the garrison looked after me in the absence of my mother.
Despite being a girl who was supposed to be interested in girly things, I became fascinated with the military. It was so orderly and neat. The uniforms were crisp and pretty. But what interested me most were the firearms, muskets, pistols, and cannons. Loud and powerful, I delighted in watching the soldiers train. When I was big enough, around seven years old, my father assigned one of his men to teach me how to shoot. That in itself would have been scandalous had I not been his daughter. As I grew, my military knowledge grew along with me.
It was this training that would save my life time and again during my life. The first time this occurred was when pirates overran our ship as my father and I were sailing to Bermuda. The crew was killed or enslaved, and my father was gravely wounded. I stood over him as he lay dying, protecting him from the band of marauders with two pistols and a cutlass. I must have been a sight to those men threatening them with my pistols, the cutlass by my side. I had dressed as a boy when the lookout had first sighted the pirate ship. My hair tied back, dressed in breeches. I was all of twelve years old. The pirate captain and the crew luckily mistook me for a young boy. God only knows what they would have done to me if they'd know I was a girl. The pirate captain was so impressed with my courage; he spared my life. Sadly, my father perished from wounds received soon after. This gave me cause to hate the men who had killed him. I vowed revenge on my father's death someday when the time was right.
The pirate captain appointed me his cabin boy when he felt he could trust that I would not slit his throat in the middle of the night. I guess I was lucky; I'd heard from other captives that 'cabin boys' were nothing but sex slaves, and when used up, the crew tossed overboard as food for the sharks and Barracuda.
As I matured, I hid my physical development in very ingenious ways. It was my good fortune that I was a late bloomer. Bandages over my budding breasts, padding to disguise my curves along with somewhat baggy clothing helped prolong the fact that I was indeed a girl.
Eventually, the crew treated me as one of their own. Refining my skills with weapons and introducing me to navigation. I learned to barter the goods we spirited away from their owners, drink, and when I got older, taking my pleasure from the ladies. I also learned what it took to run a ship, and it's a crew.
It was when I was maybe sixteen that Captain Del Rosa introduced me to Madame Bianca. Captain Del Rosa thought I was old enough to start my sexual education with the ladies. Luckily, I still had the crew fooled regarding my gender. I hoped that I could keep that ruse going with a bribe or two to the whores that serviced the crew. Meeting Madame might have been the end of my deception if she hadn't been as lusty as she was.
Madame Bianca was the proprietor of one of the bordellos in a port we frequented. When I entered, I couldn't believe what I saw. I was accustomed to being in the company of smelly men with no manners what so ever. Madame Bianca had furnished her house in fine silks, tapestries, along with elegant furniture. The women milling around were in various states of undress; each seemed to show off their main attributes, legs, and or breasts.
Madame Bianca looked me over, trying to decide which of her girls would be best for me. She asked me if I had any preferences as they all milled around me, wanting to be my first. I was very nervous, wanting to act enchanted with them. At the same time, I was scared for my life should my true gender be discovered.
Finally, unable to make up my mind, the lovely Bianca took my hand, leading me upstairs to her private boudoir. She closed the door behind her as I stood shaking.
Her voice was calm and assertive as she told me to get undressed. She was going to bathe me before she'd even consider touching me. I nervously swallowed as I sat to remove my boots. She watched to see how far I'd get. She knew I wasn't a boy, patiently waiting until I balked at removing anything other than my shoes and leggings.
She looked at me with sympathetic eyes, "Kelly, it's Kelly, right? I know you're not one of them, physically, sweet child."
I looked up at her, "How can you tell? I haven't undressed."
She grinned, "You haven't an Adam's apple, my little love. Now get undressed; your secret is safe with me."
I slowly removed my clothes as she kept talking to me. She seemed very friendly with the gentle manner in which she spoke. I placed each piece of clothing I wore in a pile as she watched. When I was down to the band covering my breasts, she told me to leave it in the corner of the room away from my dirty clothes.
Now bare naked, she told me to get in the tub she'd had filled. I complied as she rang for one of her girls to come to get my dirty rags to wash. I hid as best I could in the tub as Madame Bianca told the girl to clean or replace my filthy belongings. She partially hid me from the girl's sight just in case the girl peeked, discovering who I was. When she'd gone, Madame Bianca began undressing.
I watched with fascination as she slowly disrobed for me. I'd never seen a full-grown woman up close and bared. I was enthralled.
I asked, "Why are you undressing, Madame?"
She laughed, "To bathe you silly, I'm not going to get my clothes wet. Plus, you came here to experience your first woman. I get to fulfill that delightful obligation. Your captain will ask you questions about your time with me to be sure he got his money's worth. He's done it before, and I have no desire to cheat him."
I was stunned, "But, you're a woman, that's not right."
She grinned as the last piece of clothing dropped to the floor, "We'll see if that's what you think when you leave here, my young beauty."
I was stunned; her body was like an hourglass. Her breasts large and full much like ripe melons. Much bigger than my small berry sized ones. Her skin was like fine porcelain, smooth and silky. With my eyes fixated on her body, she slowly approached the large tub.
She entered as I looked up at her, "You like what you see, my darling, Kelly?"
I stuttered, "I've never seen a woman bare before, Madame."
She sat down in the warm soapy water, her breasts bobbing just above the surface somewhat like a whale breaching. I couldn't help but stare as they moved closer to me.
She handed me a bar of something, "Here, you soap me, and I'll soap you. Let's get that salty sea odor off of that sweet young body, shall we?"
She handed me something like a small cake. I looked up at her, not knowing where to start. She looked clean to me, so I watched as she softly rubbed her bar over me. Her touch was gentle as she glided over my shoulders then down my front. She slid the bar over my tiny breasts, noticing my nipples swell.
She smiled, "Your turn, my little doll. Wash mine; you've been staring at them enough. Touch them."
I looked up at her, quite unsure; she smiled, taking my hands and placing them on her breasts. I must say they were the softest things I've ever felt. I touched each one as she smiled down at me. She even closed her eyes for a few moments as my rough hands covered every part of them.
She asked if I had any questions about being a girl, wondering how I kept my monthly flow from being discovered. I blushed, pausing my exploration of her breasts. Looking up at her, I told her it scared me the first few times it happened; I thought I was dying. I used some rags I found and was scared that I would bleed to death, then it stopped. My stomach ached too, and I was very irritable. I tossed the bloody rags over the side of the ship when nobody was looking. I asked her if it were normal. It seemed to happen regularly. She grinned and explained it all to me; I never realized there was so much in being a girl.
When she'd finished answering my questions, she made me turn around, my back to her. She washed my hair with some perfumed concoction. I loved how it smelled. She didn't want to use too much for fear the other pirates might find me too frilly. Her hands combed through my short wet hair. They felt very nice, and I'd never been touched so delicately before. Her voice was soft and sweet.
When she'd finished my hair, she told me t lay back. I did as instructed, my head slipping in between her magnificent breasts. She placed one hand on my breast, the other on my flat stomach. Pinching and playing with one nipple, she powered the other hand to touch my sex. Whispering soft words to me, she proceeded to make my little nipples come to life while giving me a strange and wonderful feeling down below. I closed my eyes, relaxing my body, letting her words and touches someplace wonderful. She didn't do this for very long due to the limited time we had together.
When she stopped, I felt like I'd awoken from a dream. She turned me to face her. She cupped my cheeks with her delicate hands. I didn't know what was going on as she leaned in to kiss me. At first, I was scared, but her soft lips against mine felt so natural and sweet. She parted my lips with her tongue. Later she'd explain it as 'French' kissing. My tongue responded to her teasing and exploring her mouth in the same manner.
Inside me, it felt like tiny fish were swimming in my stomach. It wasn't a bad feeling; it was rather delightful. Then I felt a warmth between my legs I'd never experienced before. She asked me if I enjoyed her kiss. I blushed, telling her I did along with the touches before. It felt exciting and beautiful all at the same time.
She smiled, "Would you like to feel more, pirate Kelly?"
I excitedly nodded as she stood, offering her hand to me. I rose, and we both stepped out of the tub to dry off. She escorted me to her bed, where she told me to layback against the pillows. I did as instructed, climbing up and adjusting the pillows to lay back on. Her bed felt like I was floating on a cloud; it was so soft. I lay watching as she joined me, her eyes filled with anticipation.
"Kelly, I'm going to do things to you that might shock you at first. I want you to relax and let the feelings in you take over. Most men won't do this to any of my girls. Sweet one, you will do these things to me along with other delights before I send you back to your mangy crew. Remember, your captain will ask you questions about me to make sure I did what I was supposed to do. "
I nodded my head as she continued.
"These things I do, you have to pretend where I place my mouth on you is a male part. Have you seen those?"
I nodded, having seen some of the crew pee into the ocean.
She continued, "Inside ladies have a tiny dick that is covered up. I'll be sucking on yours, so you won't have to lie to your captain when he asked what we did. You tell him your dick was too small to put in me, so I sucked on it instead."
I nodded again, "Yes, ma'am."
"If he asks about my breasts, well. We'll get to that part, my little love."
She lowered her head between my legs, parting them further as she did. I could feel her tongue licking all around the place I pee. I was feeling those little fishes again tickling my insides. I was confused about the feeling, but I was enjoying it. She inserted her tongue in me; I nearly jumped as she swirled it inside. She was looking for my tiny dick, which didn't take long to discover. She played with it as I moaned and tried to roll on the bed. Her hands stopped me from moving as she continued teasing it. She'd play with it, then pause to kiss my thigh or my soft hairs that were growing down there. When I started to relax, she'd get back in me and make me feel like I was going crazy.
I have no idea how long she tormented me like this. Looking back, it was more pleasure than torment. I kept getting closer and closer to screaming out loud. When she placed a finger in me along with her tongue, I had to cover my mouth, it felt so good I had to yell, but I didn't want my voice to give me away.
It was exciting, and I felt like I was going to pass out several times. At those times, Bianca would pause, look up at me as I tried to catch my breath. Then she'd lower her head and take me back to the brink. Eventually, she let my body have what it craved. It felt as if my entire body had been struck by lightning. I bounced and thrashed about the bed while Bianca sat back, massaging my legs with her soft hands. When I calmed down, Bianca moved to me, and we kissed again. I took the lead this time, kissing her, thanking her for making me feel so alive. When I kissed her, I tasted something different on her lips. I asked, and she said it was me, my lady juices she said. I didn't know what to say as I kept licking my lips. It was delightful.
She grinned, kissing me once more. Then she cupped her breasts, offering them to me.
At first, I wasn't sure what to do. She looked at me, her hand behind my head gently pushing me forward.
She said, "Kiss them, haven't you ever seen a young animal at its mother's teats?"
I told her I did. I leaned in and began sucking. Once more, I wasn't sure about what was going on. Bianca moaned like I did when she was 'sucking' my dick. A teat in my mouth, my hand on the other playing with it. It felt strange and exciting. My heart was beating faster as she pressed my face harder to her large soft breast. I was enjoying touching and sucking them.
I kept doing what she wanted; her moans grew louder, and so did my excitement. She moved my free hand between her legs, whispering for me to play with her lady part. I cupped it, touched it; her juices wet my hand. Bianca told me to put my finger in her. She used her hand to guide me, slowly at first, then as her excitement grew, she made my hand go faster. Two fingers, she said, then three. My hand was moving in and out as I sucked her teat.
Suddenly her body stiffened. Her reaction was different than mine, but she later explained the results were still the same. Her juices coated my hand as my fingers moved in her. She grabbed me, kissing me as I sat stunned by her reaction. When she calmed down, she told me I was perfect. She'd say to Captain Del Rosa what he wanted to hear. She made sure I knew what to say when asked about her body and what happened.
She kissed me again as we lay together talking. Sadly, we didn't have much time left. I wanted to lay there and touch her and feel like I did earlier. We heard a knock on the door. It was the girl with my new clothes. We lay together while she entered and set them on a table. She grinned as Bianca partially hid me under the covers while I suckled once again. We got dressed after she left, I wanted to stay and learn more, but I had to get back with the rest of the crew.
That was my first time with Madame Bianca. My captain asked me questions just like she said, and I didn't lie about anything. I visited Bianca many more times. She taught me all about making love with a woman. At times she'd have one or two of her girls whom she trusted help further my education. I enjoyed telling and showing them how to please me.
Madame Bianca was my first experience with anyone sexually, but she wouldn't be the last. I discovered and enjoyed a new lover with each new port, always female, after a bit of discrete searching. Some were more interesting than others, which is normal. Spanish ladies were full of fire, the French, sultry, and sensual; the English were a bit kinky and liked things a little differently. Some of the Indigenous girls and former African slaves had some different and lovely ways of pleasing, which I enjoyed as well.
I enjoyed them all, learning and doing some teaching too, if I don't mind saying so.
I grew stronger and smarter as time passed. I fine-tuned my skills as a pirate, navigator, and seller of stolen goods. I made friends, allies, and lovers of the women that served the crews at the various brothels we visited. Some hated men, despising them for what they made them do. Many wanted a life where they were beholden to no one. Those were the ones I trusted the most taking a few into my inner circle.
I catered to those desires of a free life, creating a network of spies and lovers to aid me in my ultimate goal, a ship and a crew of my own. Taking advantage of that secretly, I showed them how to use pistols and knives. When I felt I had enough backing, I put my plan into place.
My breasts had enlarged quite a bit around the time I turned eighteen. It was becoming challenging to hide them. That's when I decided I needed to act. I took control of the ship during a visit to Martinique. Yes, it was mutiny. I considered it retribution for the killing of my father.
Before arriving in port, I suggested to Captain Del Rosa that we allow the local whores to mingle and drink with the crew for a change. Little did he know they were all my trained allies. When most of the men were drunk or asleep, the ladies and I bound those loyal to Captain Del Rosa.
Some of the crew sided with us, helping secure the remainder of the crew and Captain Del Rosa. We let the crew go before sailing out to sea and our new lives.
Each of the ladies was assigned one of the remaining crew members to watch. Captain Del Rosa, I held under lock and key. I had mixed feelings about what to do with the man responsible for killing my father because he also saved my life and took care of me. But, if it hadn't been for him, I wouldn't have needed saving. After much debate, I decided to let him loose on one of the less inhabited islands in the Caribbean. I knew I'd probably regret it someday. However, I couldn't bring myself to killing him outright.
We set him adrift in one of the ship's yawls near land. With his threats echoing in my ears, we set sail for parts unknown, looking for treasure and a new life. It didn't take long before my new 'crew' began squawking. The ladies had never worked so hard in their lives. Freedom comes with a price, and they were now paying that each day.
I couldn't and wouldn't silence the whiners while at sea. That would lead to another mutiny. So we set sail for a friendly port to offload the excess baggage. On the way, we happened upon a Spanish merchant ship loaded with treasures bound for Spain. We pretended to be disabled, getting close enough that the captain of the ill-fated ship pulled alongside us, unaware he'd fallen into my trap.
There wasn't much of a struggle as we boarded and took control. The whiners quickly changed their tunes after we'd plundered the unlucky vessel. Sadly, the most vocal handful didn't survive the brief skirmish due to poor marksmanship from their shipmates.
We took our bounty, buried our dead at sea, then continued on our way. I took myself a sweet captive, making her my cabin girl. She was reluctant at first but, with a little persuasion on my part, soon realized that serving me was much better than swimming in the Caribbean alone or letting the crew have their way with her.
She was a feisty young thing, dark-eyed, olive-skinned, with coal-black hair that hung to her waist. Her body young and ripe, she was built for pleasure, and I was going to make her mine.