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. Even bigger thanks to Alicia who thought it was quite good and gave it one last edit. 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 am also currently storing this story at /files/Authors/ShonRichards/ where you can find every part up to now. I happily read any e-mail sent me and even manage to respond promptly. "Her Cabin Boy" Part 6 By Shon Richards The next morning began uneventfully. The girl who woke me left before I could see who she was. I didn't go the common showers because of my sinful shower the night before. Even Captain Drake's quarters were tame as the lusty Captain slept alone last night. When I woke the Captain up and performed the mundane chore of getting her a glass of water, she climbed out of bed, flipped her computer on and immediately began reading files. I would find out later that the entire ship was wired into a computer network and that the other officers filed daily reports to Ashlyn. The Captain made reading the reports a daily ritual as she searched for something to amuse herself for the day. Ashlyn Drake sat at her desk, still completely nude. Even with her red hair a tangled mess she was still the sexiest woman I had ever seen. The sunlight reflecting off the water bathed her body in an amber glow. She absent- mindedly played with her nipple as she read the reports, twisting and coaxing the red nub until it was hard and flushed. I couldn't tell if she was doing it just to tease me but I enjoyed it nonetheless. "Cabin Boy, help me get dressed," she commanded as she stood up. "We already have two members of the crew in the brig for infractions. I want to spend my morning making sure that they are suitably punished. It'll be a good opportunity for you. We'll see if we can make a proper spanker out of you." Oh my God. My heart was racing as I rushed to get Captain Drake dressed. For once, it looked like I would be the one humiliating someone! I'm ashamed at how excited this made me but I couldn't deny the feeling of impending power I felt. Being the only male on board, I was always conscious of how low in the pecking order I was. When women weren't avoiding me out of fear of Drake, they were usually snickering at me for some reason or another. Captain Drake dressed the part as I helped her. Today she choose to wear a white halter-top in which the full shape of her plentiful breasts was clearly visible. She neglected to wear panties, and decided on a short red skirt that barely came down over her ass. While I laced up her six-inch-heel thigh boots, Captain Drake slipped on a leather jacket that had been torn just enough to give her the 'pirate trash' look she favored. A sword belt was added, and a dagger was slipped into a boot sheath. Once again she looked like a slut from a Pirate Romance novel. She wasn't finished yet. A red and white striped bandana was used to hold her long red hair back. This allowed people to admire the incredibly large gold hoop earrings she wore. Being a woman, she of course had to put make-up on, something that caused me to wait very impatiently. Ruby lipstick for her lips I expected, but then she took out some face paint and did something truly bizarre. She painted a black circle around her right eye, and then filled it in completely. It looked exactly like an eye patch, but being paint she didn't have to keep her eye closed. "What do you think?" My sexy employer asked. Keeping in mind that this woman decided whether I got laid on this ship, I lied. "It looks very sexy," I answered. "Perfect, let's get me some breakfast and then on to the brig," she said. Like an excited puppy I hurried behind her. Captain Drake took her time at breakfast, relishing her meal. I had the distinct feeling she was teasing me. I don't think anyone could take that long to eat. On the other hand, she was using her dagger to eat, so maybe she didn't want to cut herself. Sometimes I think she carries this pirate fetish a bit far, but since this is what gained me the chance to watch naked women all day I wasn't feeling too judgmental. Upon arriving at the brig, I felt a shiver as I stepped into a place created for the sexual bondage of others. The brig is, as you would imagine, a very dark place filled with an assortment of chairs, tables, and odd-looking wooden frames decorated with metal shackles. Light came in only through very small portholes. There were several electric lamps but they were shut off at the moment. Ornate wood paneling covered the walls, and a dark hard wood floor wrapped the room in a smoldering sensuality. I spotted a chest; similar to the one Captain Drake kept in her room. I knew what kinds of toys and chains we would find there. Taking center stage in this room of sensual trials was a nude woman bound to some sort of bench. Face down, her wrists and ankles were chained firmly to the legs of the bench. Her back and buttocks were about waist-high to me, allowing easy examination of her sensitive parts. The woman's head lifted up when we came in, revealing a pretty face framed in an oval of short blond hair. At first I thought she might be Jamie, Dr. Allston's assistant, but I saw that I was wrong. This girl had a look of fear on her face that would never appear on the bitch nurse's face. Hanging on the far wall was a table that was slanted at a forty-five degree angle. Chains suspended the table from the ceiling as well as secured the nude struggling woman on the table. She had the dark tan everyone had on board this ship, a golden color that covered her from head to toe. Her dark brown hair was in a ponytail, and it was pulled straight up and tied to post above her head. This prevented her from struggling much, which I thought was a damn shame. She had the largest set of natural breasts that I had seen, two large tanned globes that just begged to bounce around while the girl struggled I resolved to free her hair as soon as possible. "No one keeps an eye on them, Captain?" I asked. "You think I should have some big muscular girl with long blonde hair and a spiked collar keeping an eye on them?" she asked sarcastically. "This is a ship, Cabin Boy, and on a ship, everyone does their job and we don't need to set aside someone to baby-sit the disobedient slackers. First Mate Vogel assigns crewmembers to come by and give the punished a bathroom break, which is all the attention I'm willing to give those who can't follow the rules of the ship." "But Captain," the blonde protested, "Heather and I were only a little bit late to our duties! It'll never happen again!" The Captain quickly slapped the blonde's ass, causing her to squeal at the sting of the blow. "I've read your discipline report, Michelle, and according to crewmember Patton, you and Heather were over two hours late because you both overslept. I can see now that you're the type to lie and whine about your deserved fate." "Cabin Boy, retrieve the gags from the chest and gag these two sluts. I want to work on them in peace," Captain Drake said as she stroked Michelle's welt. "Aye, aye, Captain!" I beamed. Oh yeah, it was easy to get into the spirit of things with two hot babes tied up and at our mercy. I selected two ball gags from the chest and buckled them onto our two captives. This was the first time I had ever done this, and the only mishap was when I had squeezed the straps too tight on the big-breasted woman's head. Her enormous chest distracted me but she began flailing right away. I quickly loosened the stress of the gag, but Captain Drake was already chuckling at me. Great, I was already making an idiot of myself. I had to admit the ball gags looked great. The white balls held their lips open, forming a perfect 'O' of desire. It caused them to look like they were ready to suck down a cock at a moment's notice. Or perhaps they were moaning their pleasures, their lips frozen open. Captain Drake selected a pair of paddles from the chest, and surprised me by handing me one. The paddle was black with a white skull and crossbones pattern etched into it. The grip was leather, and imitated the handle on Drake's sword. Not many paddles came with a wrist guard. Captain Drake then went to Michelle's backside and motioned for me to follow. Standing on the opposite side of Michelle's exposed ass Captain Drake began my education. "If you are ever to gain any respect on this ship, you must learn how to paddle a woman's ass," my thoughtful employer said. "First, you stroke your paddle over the woman's ass like this. It helps to prepare her for the punishment to come as well as to draw her attention to the coming ordeal." She illustrated her point by rubbing her paddle over Michelle's ass, softly as if she were laying icing down on a cake. Goosebumps were rising on Michelle's ass; the tension must have been terrible for her. I helped the Captain, letting my paddle join hers as we fondled Michelle's ripe ass. When the captain was satisfied that Michelle was scared out of her mind, she continued her teaching. "Your problem is that you're too timid," Captain Drake explained. "Never forget that these daughters of dogs are getting paid a lot of money to do their duties. They knew the rules when they signed on yet they still insist on slacking off. Don't show these bitches any mercy, because they are robbing me of my wealth. On the other cheek don't let yourself get angry. If you get angry, then they might get hurt, and if they get hurt I'll lose more money from the lawsuits. Be firm, be ruthless, and be controlled. Are you ready to give her the first one?" "Aye, aye, Captain," I said, my cock throbbing from the excitement I felt. Lifting my paddle up, I remembered everything she told me. Then with as much force as I could control, I brought the paddle down on Michelle's waiting ass. Smack! The sounded exploded in the room, followed by Michelle's muffled shriek. Michelle jumped in her chains, but she was too secure to move much. I was quite proud of myself. "No, no, no," my unimpressed captain said. "Like this," she said and then SMACK! The paddle came down, flattening Michelle's left buttock. Instantly, a welt appeared in the shape of the skull and crossbones. Michelle flailed for a good three seconds from that blow. "Try again," Captain Drake said. "And remember to move your paddle around. Striking the same place repeatedly is too painful for anyone to endure, even these scurvy sluts." That was how I learned to spank a woman. I would bring my paddle down, and then Captain Drake would critique me and bring her paddle down to show me how to improve. One, two; one, two; our spanks rained down on Michelle's ever-moving ass. Red welts covered her ass as Ashlyn Drake taught me the finer points of spanking. Watching Michelle's ass bouncing from every paddle spank, I noticed for the first time how sexy an ass could be. I just didn't know that it needed to be covered in the red heat of a good spanking to be truly beautiful. Oh how her ass moved! The red buttocks would clench after every spank and often her hips would shift lewdly as she tried to comfort herself. Captain Drake would spank the lower side of her buttocks and it would cause Michelle to bounce forward, almost as if she was humping the bench. Between the two of us, we made Michelle dance on that bench as she tried to avoid the stinging spanks we gave her. "Enough, my eager cabin Boy," Captain Drake said, and I reluctantly obeyed. "It is always a sure sign to stop when the victim's tears are flowing this freely." I walked around to Michelle's head, and to my shock, Captain Drake was right. Michelle was sobbing, still twisting in her bonds as she tried to comfort herself on the hard bench. I felt like shit. While I was getting my kicks, this poor girl was crying her eyes out. Captain Drake must have read my expression, because she grabbed my hand. "Here, feel this," Captain Drake, placing my hand directly on Michelle's sex. To my surprise, she was wet - exceedingly so. I gently pushed, and my finger slid right into the slippery opening. Michelle moaned through her gag as I pulled my finger out. "Some tears are for pain, but some are also for desire," Captain Drake said. "Just make sure you know which are which." It was good advice; invaluable actually. I trusted this older woman completely and was grateful that she saw something worthwhile in me to teach. I just wished I wasn't receiving sex advice from a woman who had painted herself an eye patch. "Cabin Boy, bring me the small cat-o-nine tails from the box. Heather shall be your next study partner," Captain Drake commanded. I selected the tool she required and took the time to admire it. It was an intimidating toy. Just like the paddles, the handle was leather and shaped like a sword hilt. Tapering from the hilt were nine separate leather lashes. The lashes were a foot long and about a quarter inch wide. A little fearful of this new device, I handed it to Captain Drake with respect. "You use the same technique as you would a paddle, my Cabin Boy," Captain Drake said. She slowly trailed the rod of the whip over Heather's heavy breasts, and I bit my bottom lip as I watched. She passed the lashes softly over Heather's nipples, and already the red buds were hardening. Drake laughed but kept passing the whip over Heather's breasts. Heather stared at Drake, tensing for the lashings that couldn't be avoided. Drake knew this of course, and took her time as she toyed with her victim. Her crimson lips formed a sneer as she lazily passed the lashes over her victim. "Take your weapon, Cabin Boy," Captain Drake said, passing me the cat-o- nine tails. Heather's brown eyes relaxed when she saw me take the whip. This really pissed me off. I was used to not getting respect out in the hallways, but getting this total disregard when I was armed was just too insulting. Gripping the cat-of-nine tails tightly, I planned to do my best to wipe the relief off her face. I stepped back, and held my arm back so that I could lash her across the breasts, from right to left. SWISH! The lashes swished right across her large right breast, creating a very satisfying cutting noise as the lashes bit into her smooth skin. My first swipe totally missed her left breast, so I swung the whip backhanded. SWISH! That time I lashed her left breast perfectly, causing her whole body to shift to the right. Her ponytail went tight as she accidentally jerked so violently it pulled at her bound hair. Faint pink stripes were already appearing on her right breast, so I lashed it again. SWISH! I added to the nine marks already there with another distinct set. Again she shifted away from my whip, turning as much as she could in her bonds to the left. The ponytail jerked again, and I wondered if the tears beginning to spill from her eyes were from my lashes or the pain of her hair being pulled. SWISH! I changed my angle this time, bringing the whip down at a diagonal angle starting from higher up. This way I was able to lash the inside of her cleavage, coloring her left breast with red trails. I tried to do the right side of her cleavage the same way, but the angle was too difficult to do easily. It didn't matter to Heather; she still tried to dodge, no matter how impractical it was. Left to right, right to left, and inside her cleavage, I covered Heather's chest with red stripes. The noise was terrible and exciting at the same time. With every swing, the sound of the air being sliced was punctuated by the sound of stinging flesh and Heather's muted screams. Her nipples were bright crimson, the blood rushing as I brought the lashes straight down on her large aureoles. When I struck her nipples just right, her whole body would arch against her bonds, lifting her back and ass towards me. When my arms began to be as heavy as a cannonball, Captain Drake stopped me with a simple raising of her hand. I stopped, and realized just how exhausted I was. My arm and wrist were aching, but it was worth it. Heather's body was dripping with sweat and trembling all over from the punishment I gave her. Her heaving breasts were a dark red color with small spots of white where my lashes had somehow missed her. It was strange; I don't think I was as turned on by her generous breasts as much as I was turned on by the knowledge that I was the one who made them look so beautiful. "Check the color of her tears, Cabin Boy," Captain Drake commanded, and I knew exactly what she meant. I placed my hand over Heather's sex, which shocked her clenched eyes into opening. After pausing for a count of five seconds, I slipped my middle finger right into Heather's sex. I felt her pussy clench my finger and there was a load moan from under her ballgag. My finger fucked her wet sex for a few thrusts, and then I pulled out. My heart was racing, but I was trying to emulate Captain Drake's steel nerves by being as outwardly calm as possible. "I'd say those are tears of arousal," I said smugly as I held up my glistening middle finger. Maybe I was a little too smug. Maybe Captain Drake was just really horny. Whatever the reason, the gorgeous redhead smiled and took my hand in hers. Locking those gray eyes on me, Ashlyn stuck her tongue out and moved my finger to her mouth. Inch by inch, she sucked my finger in and I nearly whimpered from the sight. I had been daydreaming about placing something in her mouth for days now and to see my finger go where my cock could only dream nearly made me beg for sex right there. "Yes, I would say you're right," captain Drake said when she removed my finger from her mouth. Her tongue made sure there wasn't a drop of Heather on my finger when it left her mouth. I merely stood there dumbly while she talked. "Release them from their shackles, and handcuff their wrists behind their backs," Drake commanded. I did as she said; eager to do anything to take my mind off of the fingerjob she'd given me. While I released the grateful victims, Captain Drake was preparing for their next ordeal. She stepped onto a pedestal that was a foot off the ground. Opening a bottle she retrieved from the toy chest, she squirted some sort of brown substance onto her tall thigh high boots. It was distracting to watch Captain Drake make a mess of her boots and I was dreading polishing them later. When I had both Heather and Michelle down on the ground and their wrists tightly handcuffed, Captain Drake instructed me further. "Remove their gags, Cabin Boy," she commanded from her perch. "Listen my lazy wenches. I'm giving you a chance to earn back the work you stole from me. I've just poured a particularly sticky syrup on my boots, and it is your job to clean them. Heather, you have my right boot to clean, Michelle, you shall take the left. I don't want to step down from her until you have removed every lick of this syrup from my boots. I don't need to tell you two that you are not to use your hands, do I?" "No, Captain," Heather said weakly. Michelle merely stared at the tall length of the Captain's boots. I can't say I blamed her. "Well, get to it!" Captain Drake snarled. The girls immediately crawled over to the Captain, hobbling on their knees with her hands cuffed behind them. Soon they were both licking the Captain's boots, although you could see them hesitate, as their tongues tasted the salty leather under the sweet syrup. Michelle was the worst, she kept trying to lick Drake's boots in a way that didn't get blonde hair into the syrup. Drake was not amused. "Cabin Boy, get the paddle and motivate whichever one you think is the slowest." By the time I returned from the toy box, both of them were working pretty fast on her boots. I knew my redheaded captain wouldn't be impressed, no matter how much faster they were. Plus I was eager to please my demanding Captain. Rubbing my paddle over Heather's bouncing ass, I looked to my Captain for confirmation. A nodding smile was all I needed. A single spank motivated Heather wonderfully. Her entire body undulated as she tried to lick the sticky syrup faster. Since that was the first spank her bottom had received that day, I felt confident in raining a few more blows to her buttocks. Heather's round ass jerked from every blow, which was erotic enough, but Drake's sensual smile of approval was even more of a turn-on. Michelle was slowing down in my opinion, so I gave her a wake-up spank as well. She cried out as soon as the black paddle collided with her already crimson ass. Michelle was even more encouraged by my spanks than Heather was due to the tender state of her lovely tight ass. I was careful not to spank her more than twice before switching to Heather. There was no sense over doing it. Especially since Heather's ass wasn't even half as red as Michelle's. Captain Drake stood quietly as the two lovely ladies licked her boots. She stood tall and proud, her hands on her hips and her smile never losing any of it's wickedness. Captain Drake could have been posing for a painting with the commanding presence she projected. The girls, on the other hand, looked like worshipping island slaves with their dark tans and lovely nude bodies. The two women were upright on their knees, still licking the boots like their life depended on it. As sexy as they were bent over, the two of them were even sexier upright. Their breasts would hang down as they leaned forward and I had to resist the urge to reach out and cup the soft hanging tits. I didn't think Drake would approve if I copped a feel, so I stuck to spanking the two gals. Eventually I managed to get both of their asses to be the same shade of red. When the girls had finally, franticly cleaned Drake's boots, the captain raised her hands for me to stop my paddling. Hands still on her hips, she spoke down to the guilty gals. "Remember this punishment the next time you shirk your duties," Captain Drake said. "Ask yourself, would you rather clean your assigned areas with a brush, or would you rather clean my boots with your tongue?" "We'll be good, Captain, I swear it!" Heather said. Michelle tried to profuse her loyalty as well, but Drake silenced her with a raised hand. "Silence, you two aren't done yet," Captain Drake declared. "You have one more cleaning job left." Captain Drake stepped down from the pedestal, and sat down before her frightened crew. She lifted her red skirt to her hips, and leaned back on the pedestal grabbing the chair behind her to lean on. Her nude pussy on the pedestal and her body stretching back with her elbows resting comfortably on the chair seat, Captain Drake merely waited for them to get the message. Since they were slow to understand, I took the initiative to give each of them a loud, unexpected spank. "Very good, Cabin Boy," Captain Drake purred as the two girls bent down to lap at her pussy. Their hands bound, the two girls fought to keep their balance as they were both bent over. Since there was nothing for me to do except watch two pretty women lick an even prettier woman, I kept giving the two gals occasional spanks. Captain Drake didn't object. Both of her hands were grabbing the heads of her two slaves, holding them down as they licked their Captain. Drake's eyes were closed shut and her chest was breathing hard as the two girls cleaned her pussy furiously. I was jealous of the oral delights my Captain was enjoying, but I was smart enough not to interrupt her pleasure with my desires. After a few minutes of watching her enjoy herself, I noticed the Captain suck her lower lip in hard as she reached her first orgasm. Her eyes popped open and looked me straight in the face as I gave Michelle's sore ass another punishing spank. "You have learned very quickly, my Cabin Boy," Captain Drake said as she shifted her pussy closer to the two girls. "In return for your good services this morning, I give you permission to pick a mouth and fuck it." "Yes ma'am!" I snapped, and I think I even saluted her. The paddle was tossed to the ground as I quickly removed my shorts and underwear. I knew exactly whom I wanted and I grabbed big-breasted Heather by the ponytail and led her away from her cleaning chores. Following me on her knees, I took Heather to a nearby bench and sat down. This time, her eyes were full of fear instead of the cold disregard she gave me earlier. Still sitting upright, I used my grip on her ponytail to direct her to my erect cock. Without a word of command from me, Heather used her lips to lift my cock and swallowed me in. "Ohhhhh" I moaned as Heather's lips engulfed my cock, all the way down to my base. I squeezed my thighs around her, crushing her sore breasts between my thighs. It was such a turn-on to feel the heat still rising off her tits from the lashing I gave them. Heather moaned in complaint to my squeezing, but I ignored her. It's a credit to Captain Drake's lack of mercy that I was able to treat a beautiful woman as coldly as I did. With all that I had suffered on this ship, I felt hostile to Heather for shirking her duties. What right did she have to goof off when I've had to endure public humiliation? That Heather was obligated to satisfy me was a logical assumption, and one that I fully expected to see completed. What was really weird was that I think Heather agreed with me. Her big brown eyes were full of submission as she looked at me, and she never broke her pace for a moment. I knew she had to be exhausted, but still she kept bobbing her lips over my cock. Her head bounced up and down the full length of my shaft, my hand still gripping her ponytail tightly. Somehow, after all she had gone through, Heather still managed to suck me tightly. Even her tongue showed no sign of slowing as it completed swirl after swirl on the tip of my cock. Across from me, Captain Drake was enjoying the show. She was staring at Heather between my legs as Michelle licked between hers. Drake had opened her shirt and was playing with her full breasts. From my vantage spot, I could see the dew gathering on Michelle's pussy and I knew how badly she was enjoying this. Drake saw what I was looking at and she blew me a kiss. Watching that mouth pucker up almost made me ejaculate right there. It was when Drake clutched Michelle's head with both hands and started climaxing loudly that my nerve finally broke. I answered her loud moan with a moan of my own. Heather stiffened when my cock exploded in her mouth, but my grip on her ponytail prevented her from leaving. Keeping her pinned, I emptied my cum into her mouth. Heather gave in and moved her head very slowly up and down my cock, milking the final spurts from my member. Only when my cock began to shrink in her lips did I let go of her, and she was quick to collapse on the ground. Heather lay there gasping, shifting her legs back and forth. I knew she desired her own relief, but I also knew it wasn't mine to give. Besides, my toes were still clenched from the force of my orgasm; I could care less about her problems at that moment. Later, when Captain Drake was finally as sated as I was, she pushed Michelle's head away and gave me further orders. "Cabin Boy, shackle these two to those chains hanging from the ceiling," she commanded. The girls groaned briefly in disappointment, but didn't say anything. I was relieved; I didn't think I had the strength to do any more paddling. The girls were heavy to pull up, but they didn't resist. I released their wrists from the handcuffs, and then lifted their arms high above their heads and shackled them to the ceiling. It was a terrible temptation to fondle them, especially Heather with her breasts just standing there unprotected. Captain Drake came up to inspect my work, and probably also to ease my temptation to get a last lick of their tits. "I know you two sluts are dying for some sort of sexual release," Drake said as she buttoned her shirt. "Well, that's too bad! To complete your punishment, both of you will be left here for six hours to reflect upon your laziness. You'll receive a lunch break, but there will be strict orders for you not to masturbate until your punishment is over. Am I understood?" "Yes, Captain," they both said miserably. "Good," Drake said simply. "William, after you report to Second Mate Theresa for your exercises, you have the rest of the day off. You've earned it." "Thank you, Captain," I said, quite surprised that I was being rewarded for receiving a blowjob. "Don't thank me," Captain Drake said with her usual wicked smile. "I just want you rested for your duties tonight." Then she left. I stood there, a little worried. Michelle said "uh oh." I have to admit, I agreed with her. To be continued, If you enjoyed this part, or the story as a whole, please drop me a line at shonrichardshsd@earthlink.net