This story is copyrighted by me, Shon Richards. Please don't plunder it for your own pleasure. I wrote this story a few years ago and even though I know I can write better, I think it has a certain charm. This is the first part of a FINISHED novella that involves a male sub, one eccentric female Captain and a ship full of sexually adventurous women. Yes, it's that kind of story. There's bondage, domination, spanking, oral sex, anal sex, orgies, pirate lingerie and even a little romance. What there isn't any of are pedophilia, nonconsensual sex, and anything involving former food. Big thanks to Souvie and Pami who always had an interest in this story and bugged me to post it. Big thanks to Alexis who told me I could do better. A big thanks to all the Thigh Vs. Thigh fans who let me know that funny erotica had an audience. I hope this story entertains them as much as Amy and Bethany did. I happily read any e-mail sent me and even manage to respond promptly. "Her Cabin Boy" Part 3 Dr. Allston had called for a lovely blonde to escort me to my quarters. I didn't have time to catch her name because she was soon informing me of my restrictions aboard the ship. I was assured that I would have different privileges once the Captain had approved of them, but it didn't cause me to relax. There was a common bathroom; two doors down from my quarters, and the blonde threatened me with vague dooms if I wondered any farther down the hall. Dinner would be served to me, further limiting my freedom aboard the ship. If it wasn't for the fact that the blonde was tanned, about five feet seven and possessing a husky voice, I might have been worried about my captivity. It also didn't hurt that she was wearing tight black shorts and a white cotton shirt that clung to her body like a second skin. It's very hard to be intimidated by someone when you know the exact location of her nipples, as well as knowing that there was a slight tear in the right cup of her white bra. Maybe that's why the Captain had all her women dressed as rejects from a pirate porno movie, to keep any of them from feeling confidant enough to challenge her. Nah, she's probably just a pervert. I spent my first night aboard Captain Drake's ship in my very own quarters. That's not as luxurious as it sounds. My room was maybe eight feet across, and that wide. Somehow they crammed a hammock in there, probably to make room for the footlocker underneath it. The footlocker contained nothing but I figured it was for my new clothes, if I ever got them. There was another door to my quarters but it was locked. It made me a bit uneasy when I realized it was locked from the other side. I checked the door that opened into the hallway, and was relieved to find it locks from the inside. It was as bare as a cell, but at least it wasn't going to be my prison. A rather harried looking brunette served dinner. After being alone for five hours, I would have talked her to death but her appearance discouraged that. For one thing she was topless, and it's hard to hold a normal conversation with something as stacked as she was. Second, she had the words 'Drudge Duty' written across the top of her head in red letters. Third, except for her tight black shorts, every part of her tanned body was covered in some sort of grime. I recognized flour; ordinary dirt and I could be wrong, some chocolate sauce on various locations of her body. Instead of wearing a bandana like everyone else, her long hair was loose and hanging past her shoulders. That must have been inconvenient and I could already see various knots and tangles. It was pretty easy to figure out that this girl was doing some sort of punishment duty. The scowl on her face kept my mouth shut. Surprisingly, dinner consisted of a beef stew with plenty of meat and vegetables. I think I was expecting oysters or maybe some sort of vegetarian platter. How the hell did these ladies stay in such great shape eating stuff like this? I decided that I didn't care. I was too hungry. Thankfully, the girl had also brought me two pitchers of water to wash the meal down. It was difficult to eat in a room with no furniture, but I placed my plate on the footlocker and did my best. It was even more difficult to not watch the pitchers constantly. The rocking of the ship had me terrified that they would fall over. As you can tell, I was dreadfully bored if falling pitchers kept me occupied. I got to bed early and enjoyed a rather restful night in my new hammock. It didn't take me nearly as long as I thought to get used to being suspended in the air, and I rather enjoyed the gentle rocking motion. I would have easily slept till noon if it weren't for the rather loud banging on my door at eight in the morning. "Get up you lazy scurvy dog!" a voice yelled from outside. I nearly fell out of the hammock; finding out that leaving a hammock was much harder than getting into one. Running to the door, I came face to face with my employer once again. Captain Drake was wearing a far different outfit from the one she was wearing last time. She was wearing a tight white ruffled shirt that came off her shoulders. The top half of the shirt didn't really start until about halfway up her breasts. Her nipples were visible through the sheer whit material, and I wondered if that was going to be standard for the rest of the crew. The shirt covered her arms, ending in feminine black studded gloves. She was wearing very short pair of black shorts that looked painstakingly torn at the edges. These shorts only came down halfway her lovely pale thighs. The majority of her legs were covered in black shiny boots that came up just shy of knee. The heel appeared to be four inches at least, but Captain Drake didn't bother with a point on her heel. She was much more sensible, both of her heels were wide and gave her plenty of support while she towered over her crew. The accessories really caught my eye. She had a scabbard tied around her waist and her hand always rested on the jeweled hilt of her rapier. A red wide- brimmed hat held her long red hair back, exposing her forehead in a sexy, almost tomboyish manner. A large gold hoop earring hung from her right ear and she tilted her head towards me so I had to notice it. A black velvet choker encased her neck, adorned with a silver skull on her throat. "Well, do I look the part of a Captain about to engage in debauchery on the High Seas?" she asked. "Yes," I said simply. I didn't know what else to say. She looked like she would win first prize at a Halloween costume and she was certainly extremely sexy. I just didn't know how seriously I could take going through a whole voyage with her. How was I going to keep from laughing? Captain Drake's gray eyes darkened, and she said "Turn around please, Mr. Rosen. Remove your pants." I did as she said, thinking she wanted to inspect me again. It was easier to pull my pants down this time since I wasn't looking at her. Almost immediately I felt her hand lash down and deliver a barehanded slap onto my ass. I was stunned, both by the unexpectedness of the blow, and by how powerful it was. My underwear gave me little protection against her leather-clad hands. I felt that blow, and my cheeks were stinging beneath. Of course I cried out. "That was your first lesson, William," Captain Drake said. "Always address me by my title of 'Captain', or you shall have a very difficult voyage. Leave your pants off today as a reminder of your disobedience. Am I understood?" "Yes, Captain," I said. Now that I had my pants off and my ass was burning, I found it much easier to not laugh at my employer. "Very good then," she said. "Let us go to my quarters, and I'll instruct you on your duties. Then we can tour the ship and give it a good inspection." "You've already seen your room, and today we'll equip you with your wardrobe. We don't have much of a dress code here, although you will find it easier the less you wear. That way you don't have to track down your clothes at the end of the day when you've been forced to strip." "What is the other door for, Captain?" I asked. "That leads into my quarters and it is only lockable from my side," she answered. "It'll be rare that I'll lock the door. I prefer to have you ready to assist me as soon as I call. Be sure you are prompt when I do call, or I'll have you sleeping at the foot of my bed." "Yes, Captain," I answered. Something told me she wasn't kidding. My thoughts of her sanity were replaced with sheer awe when she revealed her room by going through the doors in the hallway. It was huge, easily forty square feet. The far wall was completely made of windows, and I could see out onto the ocean's horizon. Heavy red curtains hung on the wall yet I had a feeling that Captain Drake rarely ever closed them. That certainly didn't seem her style. Paintings hung on the other walls. A quick glance saw that they were all actual paintings and not just posters or prints. The art style was interesting though. They were all in the same bold colors and subject matters of cheap romance novels. Tall muscle men with long blond hair and swooning damsels with enormous breasts were depicted in every painting. What made these paintings unique was that no romance novel cover was ever this pornographic. On romance covers, no man ever dipped the damsel so that he could stick his cock between her legs. There were also nipples, cum shots and bite marks depicted, which made my underwear very tight. There was plenty of furniture, almost every kind you can imagine, and all of it appeared to be in gothic style wood. Chairs were everywhere and all of them had manacles on the legs and arms. Three huge wardrobes dominated one wall. They were large enough to clothe a small army or one wealthy psycho woman. A large desk was in the corner with a suspicious rug and chains underneath where the legs went. A dinning table was toward the center of the room and it had seats for eight. Like the desk, it too had a large number of chains and collars underneath it. I had the feeling that Captain Drake kept her servants very close on hand, or leg as the case may be. A good ten feet from the windows was the true center of the room: the bed. Four-posters with an impressive red canopy, the bed could easily accommodate eight people if it had to. The frame was very solid and was decorated with various metal hooks and rings. The pillows faced the window. I envied Captain Drake for having such an impressive view to wake up to every morning. The sheets were satin, which did not surprise me in the least. A chest was open at the foot of the bed with sextoys and chains spilling out of it. My legs shifted uncomfortably as I thought about the hedonistic acts that must have occurred in this room. It was hard enough trying to appear calm with my erection so obvious in my underwear. I swore to myself to never forget to call her Captain again. The embarrassment was just too much to bear. "Let me explain your duties, William," Captain Drake said as she sat in a regal looking armchair. "In the morning you will be awaken by the servant girl who will bring your breakfast. You'll have twenty minutes to wake up and eat. Then you may use the shower in the common bathroom down the hall so that you can clean up." "The common showers, Captain?" I said. "I looked at them last night, and there's no stalls or anything. Are we the only ones who uses them?" She laughed and said "Of course not! I have my own private bath and shower. You and the rest of the crew will just learn to share. Be warned though. You're the only man on this ship and I will not tolerate you having sex with the other crew. You're my status symbol and a constant reminder of my power. Maybe they can fuck you with my permission, but never without. If any one of those sluts approaches you for sex, report them and you will be rewarded. Disobey me and you'll be severely punished." She said it so casually. It wasn't the casual manner of one appearing to intimidate, but the manner of one who was stating the facts. In fact it was almost as if she was daring me, curious if I was smart enough to elude her. She didn't have to worry. The only one planning head games in this room was she. Captain Drake played with her earring for a minute, twirling it in her gloved fingers. We waited each other out. "You'll have an hour total to prepare for your day," she continued, apparently satisfied with me. "Then you'll come in here and wake me up. There's no telling what I'll have you do when I first wake up but I suggest you obey me. Most likely I'll have you dispose of whoever was entertaining me last night. Once I have awakened, had my breakfast and taken my shower, then your duties begin in earnest." The next hour was spent on my duties. It came as a relief to discover that my role wasn't completely as a sex slave to this woman. My chores included polishing her dozens of various leather articles of clothing, cleaning the windows to her bedroom, and general dusting duties of the room. I also was responsible for the maintenance of her chains, leather bonds and sex toys. Keeping her toys stocked with fresh batteries was perhaps my most important job. I had no idea how to clean a chain or fix a vibrator motor before I started working for Captain Drake, but after two hours, I knew enough to open a hardware store. I had to give her credit; she wasn't a wimpy rich snob who didn't know how to get her hands dirty. She personally taught everything I learned. It was weird sometimes receiving instructions on cleaning from a woman who was carrying a sword and had her breasts an inch away from falling out. As weird as it was my erection never went away. "I have almost forgotten about your clothes," she said as she snapped my underwear band. My face turned red, but I didn't protest. I was just glad to be finally getting some clothes on. Captain Drake went to a chest that was sitting by her door, and tossed me some clothes. It consisted of a loose red and white striped shirt, a pair of black shoes and a bandana. That was it. No underwear or pants to speak off. When I didn't get dressed right away, Captain Drake fixed me a meaningful glare and fingered the pommel of her sword. I got the hint and slipped on the shoes and shirt. "Place the bandana on your head, like this," she offered as she adjusted herself. Captain Drake came really close to me at this point and I could smell the salt of the sea on her hair. This close to me, I found myself stuck on where to look at her. The valley of her cleavage was so blatant and arousing, I couldn't bear to look down. Her face on the other hand was just as sexy with her wet scarlet red lips and bright gray eyes. No matter where I looked my erection just kept growing. "Fuck me for a horny slut, but I can't wait any longer," Captain Drake said, echoing the thoughts in my own mind. She reached down, and held my underwear with one hand. With her free hand, she drew her sword; the rapier making a hissing noise as it left the scabbard. I closed my eyes involuntarily as the sword came down and then breathed a sigh of relief as she sliced my underwear open at the waistband. The remains of my underwear fell to the ground, landing at her black boots. Deftly, she stepped behind me, sheathing her sword at the same time. Grabbing my wrists in her gloves, she held my hands behind my back as she snapped on the handcuffs that she had just taught me to clean. My hands behind my back and my underwear in shreds on the floor, I felt a panic attack as a sense of helplessness came over me. How well did I know this woman, and could I trust her? I heard the sound of her shorts and scabbard joining my underwear on the floor, and I decided I didn't care. She stepped in front of me, her ass nude and inviting as she walked away to the bed. She sat down and spread her long legs, keeping her boot-clad feet squarely on the floor. I could see right between her legs and at her nicely trimmed public hair. Her hair was shaven into small V-shape of hair, and I was relieved that this crazy woman didn't have it in the shape of a skull or something else equally ludicrous. I started to move toward her, and she held up her hand. "No, no, my dear cabin boy," Captain Drake said. "Approach me on your knees, or approach me not at all." "Captain?" I said, my voice almost slipping into a whine. "Do as I say, or else I'll just masturbate and make you watch," she threatened, and her hand dipped down between her legs. Stunned by how easily she was able to touch herself with me in to room, I almost just stood there. It took me a second to clear my head and I reluctantly fell to my knees. She laughed at me, and I felt my face flush further with embarrassment. Now that I was on my knees, there was no going back. I began the long crawl to her, my journey made awkward by my hands behind my back. My cock swung heavily between my legs, bouncing with my need and from my humiliating crawling. Somehow I made it to her, and as I tried to rise, she placed one of her boots on my shoulder. Her boot forced me back down to a kneeling position. I looked at her, and she was shaking her head mockingly. "Not so fast, my cabin boy. You haven't swabbed the decks yet," she said. Swabbed the decks? What was that, some kinky new word for oral sex? I looked at her confused, and she simply smiled that infuriating smile at me. "Clean my boots, Cabin Boy, with your tongue, and then we can play," she said. I looked at her, torn between being offended and being aroused. Licking her boots? I couldn't even imagine that level of humiliation. I imagined how I looked already, with my hands bound and my cock waggling between my legs. There was no way I was going to add to that degradation! But, my willpower weakened as I knelt between Captain Drake's open legs. There her pussy was, literally a boot away from my face. The sunlight reflected off of the little bit of moisture that was leaking from her sex. Even when I tried not to look at her aroused pussy, my eyes kept seeing her explicit paintings around the room. There was no denying how turned on I was and there was also no denying that she possessed the wealth needed to pay my salary. Closing my eyes, I slowly bent my head, and extended my tongue. The leather tasted like salt but I licked a few inches anyway. I didn't know how much licking Captain Drake expected of me but I continued anyway. Her other boot was planted firmly on my chest, holding me back while I licked her other boot. Pinned by her heel, the only way I could reach certain spots of the boot I was licking was by extending my neck, and sometimes reaching far out with my tongue. Sometimes she would laugh at me as I tried to reach her boot, and the shame I would feel would just be terrible. I felt so degraded, and yet I didn't care if it meant I would be able to fuck that pretty pussy again. When her boot was shiny from my licking, she released her other boot from my chest. I was relieved when she placed both boots back on the floor. To my embarrassment, my cock was still as large as ever. It was a reminder that no matter how degraded I felt, she still turned me on. I hated her for it and yet, I still wanted her. "Not bad for your first time, my pretty cabin boy," she said, and a small piece of my shame faded. She called me pretty? That wasn't something I was used to hearing from a woman. "Now, I wanted you to bring that mouth over here," she said, taping her sex with her gloved finger. I nearly stumbled as I crawled between her legs on my knees. She laughed again, but I ignored her as I dived between her thighs. The soreness of my tongue was forgotten as I clove her pussy lips with my tongue. The salt of her boots was replaced with the salt of her juices flowing onto my chin. God, she was so wet! I felt a surge of pride to know it was for me. My tongue found new life as it lapped at the never-ending wetness that was pouring from her sex. "Oh, yes!" Captain Drake growled, and her gloved hands grabbed the hair on my head. Tangling my hair in her fingers, she pulled me deeper between her legs. The boots were still firmly on the ground and I realized my captain had more self-control than I ever would. My tongue found her clit easily. It was very engorged. Stroking her clit with my tongue, Captain Drake shivered and dug her fingers tighter into my hair. This was my revenge, for as I sucked her clit between my lips, I would flick it savagely. Her moans escalated as I bit lightly on her clit. When I could tell her breathing was getting too fast, I released her clit from my lips, and began licking her pussy with wide strokes of my tongue. This time I was laughing, as Captain Drake moaned her frustration at how I cheated her orgasm. "You did that on purpose," I heard her say, without any resentment. "I'll just have to find a chore for you that you can't cheat so easily. Stand up!" I did as she said and she removed something small from her nightstand. It was a small leather ring, which she then slid onto my cock. She wrapped it down onto my base, right where my cock emerged from my balls. My cock throbbed in her gloved hands and she snapped the ring tight, very tight around my cock. "There you go. Now you are ready to serve me," Captain Drake said as she grabbed a handful of my shirt collar. She pulled me down onto her, and slid my cock right into her treasured love chest. With my hands tied behind my back, there was no way to support myself so my upper body simply collapsed on top of Captain Drake. My Captain grabbed a few pillows and placed them under herself, which at least gave us an angle to work with. I was still trying to find a way to be comfortable when I felt her hand slap down on my ass. "Fuck me Cabin Boy!" she commanded. Her slap made me jump but her command made me move. As awkward as my body was, I made the most of my hip motion. My cock plunged into her pussy, sinking deeply into her liquid heat. Pulling out was harder but somehow my hips managed to pull back enough to allow myself a decent thrust back into her. It was difficult work but it was also fun. Squirming on top of my captain, I could feel her breasts pressing against her shirt as they pressed against me. Her hands were firmly on my ass and pushing me to fuck her harder. It was when she started spanking my ass with her leather-gloved hands that I got pissed. My hands were bound and my mouth was sore, and she still wanted more from me! Angry, humiliated and frustrated, I gave her all I had. My hips crashed into her hips. I pumped as fast as I could into her pussy. Her moans turned to grunts as the force of my cock rammed her. With my thrusts, I spanked her pussy as hard as she had spanked my ass. It was petty of me, but it made me feel good to replace her knowing smile with groans of shock. Watching her lips part and cry out, I felt my cock begin to surge with cum. I pumped faster as my orgasm approached, but something strange happened. The familiar tension I felt when I was about to ejaculate stopped, and stayed at the same level. Still thrusting away at my Captain furiously, I soon figured out the source of my problem. It was the damn ring around my cock! Somehow it was too tight to allow my cum to travel up my cock. In this perpetual state of near ejaculation, the pleasure of sex was attaining a new level that blew my mind. My cock was alive with sensation and I could feel every tiny fold of her pussy as it gripped me with every thrust. Faster and faster I pumped, trying to overcome that leather ring and reach the orgasm I deserved. While my body was on top of Captain Drake, trying to fuck her with no hands, her body was squirming with the approach of her first orgasm. I felt her fingernails dig deeply into my ass, causing me to cry out. She cried out too as I felt her hips buck with her climax. It was amazing; I'd never felt a woman twitch so powerfully. It was like she was being electrocuted- the way her hips shook and undulated almost threw me from the bed. That's why her nails were so imbedded in my buttocks; I wasn't going anywhere but deeper. "Oh yes!" she cried out. "Fuck me, fuck me, fuck me!" she commanded. I obliged her, stabbing her repeatedly with my cock. The bed was shaking with my impacts as I tried to throw myself between her legs. From the twitching of her hips, I could tell when she climaxed. Six orgasms I counted while I still hungered for just one. "You're starting to slow down, Cabin Boy," Captain Drake said. I looked into her gray eyes and could only moan as answer. She was so sexy, even crushed under me with her red hair spilling from her bandana. The damn ring around my cock prevented me from climaxing and I was ready to do anything to finally cum. "Does my cabin Boy want to spurt all inside me?" she asked as she rolled me onto my back. "Yes, my Captain," I answered. My heart was racing as I lay there. My hands were underneath me but she was climbing onto my legs, facing me. My cock was red with lust and glistening with her juices. Captain Drake held my cock with her gloved hands and I thought I was going to cum right then. I didn't though, the damn ring made sure of that. "So you want your hard cock, in my pussy, and you want to fire all of your cum into me?" she asked, smiling because she knew the answer. "Please, my Captain," I moaned. I was embarrassed by how badly I wanted her after all she had done. Worse, my hips betrayed me and lifted the lovely Captain slightly. She laughed and said, "I do love a Cabin Boy who knows what he wants." This shamed me further but then she released the snap on the leather ring. I gasped as my cock immediately felt as it was ready to climax. With a single fluid motion Captain Drake mounted me, sliding my cock right up into her sex. As soon as her bush came down on my balls, I ejaculated. The orgasm was so fucking powerful. I sat up with the force of it, and Captain Drake grabbed my hair and kissed me fully. Sitting up, with this wonderful woman sitting on my cock, I shot myself into her as I kissed those hungry lips. Lost in her kissing, I don't think I even moved as my cock simply drained itself of its burden. It felt like I came for an hour though I know that at best it could only have been a few seconds. When my cock finally began to wilt inside Captain Drake, she broke our kiss. My hostility for this woman was gone. She had taken me to a higher plane of sex and I was willing to follow her through Hell if it meant repeating that magic again. Turns out, she had other places for me to go first. "Now that you have served your Captain," she said as she unfastened my cuffs, "it is time you learned how to clean your Captain."