Message-ID: <42570asstr$1053547806@assm.asstr-mirror.org> X-Original-Message-ID: <017001c31fa2$dda50b90$6501a8c0@serena> From: "Shon" X-Priority: 3 X-MSMail-Priority: Normal X-MimeOLE: Produced By Microsoft MimeOLE V6.00.2600.0000 X-ASSTR-Original-Date: Wed, 21 May 2003 10:11:25 -0400 Subject: {ASSM} "Her Cabin Boy" (13/21) M/F, Femdom, Bondage, Humiliation, Orgy Date: Wed, 21 May 2003 16:10:06 -0400 Path: assm.asstr-mirror.org!not-for-mail Approved: Newsgroups: alt.sex.stories.moderated,alt.sex.stories Followup-To: alt.sex.stories.d X-Archived-At: X-Moderator-Contact: ASSTR ASSM moderation X-Story-Submission: X-Moderator-ID: RuiJorge, dennyw <1st attachment, "HerCabinBoy13.txt" begin> 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 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 http://www.asstr-mirror.org/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 13 By Shon Richards It was the strangest party I had ever been to. Latesha was strapped over a barrel with very thick chains, a bar was set up on the deck so that the women could drink freely, and Captain Drake had lawn chairs brought out so we could relax while we took turns ravishing our prize. Acquiescing to requests by the crew, Drake even allowed a stereo to be brought up so that the girls could have something to dance to. Kitchen drudges served food on platters, their topless servitude exciting our team members as we anxiously awaited the chance to enjoy our plunder. Captain Drake looked more impressive today than ever. The fury of the deck fight had flushed her tan, making her olive skin even darker and more exotic. She loosened the buttons on her flowing white shirt, giving herself a plunging cleavage. The belt was still cinched around her waist but the shirttails had risen well past her ass due to her exertions. I was still amazed at how she hadn't worn any pants or panties today, but maybe having her pussy flash everyone from underneath her shirttails was a distracting tactic for her fighting. "Good job, William, I knew I could rely on you!" Captain Drake said, giving me a hearty slap on the back. I flushed with pride. "Thank you, Captain. I'm just relieved I could serve you as you wanted," I said. She looked me strangely, in a way I wasn't familiar with from her. It was a look of assessment, and something from the smile she gave me, I felt that I had passed. When I thought back on what I said, I thought that maybe my words sounded insincere. More likely, my words sounded TOO sincere, and she wanted to make sure that I was speaking from my heart. Captain Drake must be more aware of what her crew thought of her than I realized. It left me with some questions though. If she knew how much her crew was untruthful in their declarations of loyalty, then why did she take such delight in pushing them as far as they'll go? "Captain, don't you ever worry that one day you'll piss the crew off, and they'll mutiny?" I asked. "Your concern is sweet, cabin boy," she said with a giggle. "You forget, the terms of a successful mutiny is that I must be captured when the ship comes into a port. We still have three weeks before we reach the closest port. It would be insane to try a mutiny now, keeping me imprisoned for three, two or even one week would be too much trouble." Drake then leaned close to me, her hot breath tickling my ear and her scent of perfume mingled with sweat exciting me. "You can bet on one thing though," she whispered. "Two days before we go to port, I'm going to barricade myself with a few trusted crew members and prepare for the worst." Our small moment of discussion over, Drake returned to her fun. The bottomless Captain walked over to the bound Latesha and raised the black woman's white skirt. She gave an appreciative whistle at her captive's round nude ass. The two halves of her buttocks were perfectly round and inviting. Drake pinched Latesha's ass and nodded with approval at the dark softness of her flesh. Latesha jumped when she was pinched, but was wise enough not to complain. "I'm surprised this slut didn't tempt you with her lovely ass," Drake said as she stroked the ass in question. The stroking was similar to what she does when she's getting someone ready to be spanked. "She did, Captain," I reported. "She tried to get me to hide with her by bribing me with sex." "She did?" Drake said scandalized yet not with any trace of surprise. "What did she do when you turned her down?" "After I turned her down, she masturbated in front of me," I said. Drake's smiling face contorted to a snarl and she spanked Latesha's ass hard. "What?" Drake said. "Such audacity! You'll pay for this, bitch! If you tried this with one of the women, I would expect it, but to try to fuck my cabin boy is too much! He's mine, and mine alone. You'll pay for this with your hide. Jeanette, step forward!" A long-haired brunette stepped forward, clad in tight leather pants with various holes cut into them. She was topless and her small breasts were shiny with sweat. Jeanette was as sexy as the rest of the women on this vessel, small breasted or not. Her hair was woven into a braid that came halfway down her back, and with her hair pulled back from her face, she reminded me of the no nonsense teachers I had last semester. If it wasn't for her lack of a bra or shirt, I would have expected her to start a lecture. I wondered if there was a memo I missed encouraging everyone to either go topless or bottomless. "I'll give you a choice, Latesha," Drake said as she pulled hard on the bound woman's head. "You can back out now, or later by yelling the word 'shark' and we'll stop any punishment or other activity and let you go. The only catch is, you'll forfeit the prize money you earned today. Understand?" When Latesha nodded, Drake turned to Jeanette and said, "Give her 20 lashes, Jeanette," Drake said, taking off her belt. She handed Jeanette the belt, and Jeanette took a few practice swings with an expertise I certainly didn't possess. "Isn't Jeanette something?" Drake said walking over to me. She took a mug from a kitchen drudge and drank down the contents in one gulp. "I found her working as a dominatrix at an S&M club. I wanted to make her an officer, but she told me she had no interest in being in charge of something as mundane as running a ship. Jeanette was more than happy to work on a lesbian ship, but she didn't want any leadership roles. Who would have thought that a dominatrix would avoid responsibilities? She was too sexy to pass up, so I hired her anyway." I joined Drake as she sat down on some of the lawn chairs she had brought up. We're sitting more than ten feet away from Latesha's exposed ass. Jeanette was finished with her warming up, and stepped back to give her better access to her job. The former dominatrix's body moved smoothly as she pulled her arm back and then swung with precision at Latesha's ass. She even had a follow-through, which was quite amazing to watch. I had no idea a woman whipping someone could appear so sexy. CRACK! The first lash smacked loudly into Latesha's ass, followed immediately by Latesha's scream. I jumped in my chair, and even Drake jumped at the volume of that scream, but Jeanette didn't even flinch. The stern woman just pulled back for a second swing. When the second lash fell heavily on Latesha's ass, half the crew turned away as Latesha's shriek drowned out the roar of the wind. I couldn't turn away although I wanted to. There was an intensity that Jeanette had for her job that was fascinating to watch. There was no brutality or malice on her face, she was just focused on doing her job as best she could. By the time the third lash fell on Latesha, her ass was turning a bright pink despite the dark color of her skin. I'm not sure if I could have kept whipping at that point because the color change was so dramatic. If I kept working for Drake, would I possess the same level of professional detachment over time? Jeanette's aim was perfect as evidenced by the wide red stripes on the displayed black ass. Her lines were parallel to each other, running left to right over both of Latesha's buttocks. The bound Latesha screamed with each new stripe, and her legs pulled at the cuffs that were around her ankles. Her ass was clenching, a very erotic sight considering how full and round her ass was. "Shameful," Drake said as Latesha screamed again. Jeanette had covered her ass with stripes, and was now going back over her work with diagonal lashes. "Shameful? What do you mean?" I said as I drank from an offered mug. I wasn't sure what it was, it tasted like beer, only sweeter. "The way she's screaming," Drake said with contempt. "The whole crew thinks I'm murdering her." "Well, her ass is red, and that's a pretty big belt you were wearing," I said before I could stop myself. Damn, I wasn't willing to criticize my Captain for that trouble-maker. I still remember the painful teasing she gave me. Luckily, Drake didn't take offence. "Don't even talk about the belt. Tell me William, did your parents ever spank you? Did they use a belt? Was it the most horrible thing you ever felt? Or are some of the whips and paddles you clean every day more capable of harm?" As soon as she mentioned my parents, I saw that she had a point. My father used his belt quite often when I was a kid, and let's face it, he didn't have any of the skills that Jeanette and Drake had. My father would just wail on my ass, while a true expert of spanking knows that you need to move the point of impact around the body in order to dilute the pain. The more I thought about it, the more I agreed with Captain Drake that Latesha had it easy. "Think about this," Drake added. "If you were getting spanked, and it was so painful that you had to scream that loudly, wouldn't you say anything to make it stop? Like the safeword I gave her? Even if it meant giving up your money?" "Hit her harder!" I yelled out. Drake laughed while some of the crew gasped. Unfortunately, Jeanette only had three more lashes to go, but she did put some extra swing into them. Latesha pulled hard at the restraints around her ankles and wrists, but escape was futile. Jeanette finished her lashings with pinpoint precision, covering the last few inches of Latesha's large buttocks with red stripes. A strong wind picked up, and Latesha writhed with real discomfort as the salty wind touched her tender ass. "Bring the swing to Latesha's face. I am ready to claim the Captain's share of our prize," Drake announced. Two of Drake's crew scurried and brought around a swing stand that I hadn't noticed before. It was a simple device, made of two poles that were joined at the top by a single bar. A rope swing hung down, with a seat shaped like the hammock I sleep in. The two women brought the swing to Latesha's barrel, and slipped it into slots bolted into the ground. I marveled at how much planning went into this. The deck had been ready since we left port for someone to be strapped onto a barrel, and for a swing to go in front. My Captain had all of this ready, long before she knew the circumstances that would cause Latesha to be in this predicament. The tanned Captain smiled as she settled into the swing. It didn't surprise me that Drake's crotch was level with Latesha's face. The black captive lifted her head up and groaned as she saw Drake's crotch inches away. Drake opened her legs widely and the swing accommodated her easily. My Captain reached down and grabbed a handful of Latesha's braids, causing her prize to lift her head up high to see her. "Want to back out?" Drake asked simply. Latesha shook her head. "Then eat my pussy well, and I'll spare you more spankings." Drake gripped Latesha's hair in her hands and pulled her crotch over to the captive's mouth. The swing moved slightly as the ship rocked back and forth but the Captain held onto the long braids, keeping the bottom of the swing always at Latesha's mouth. Latesha buried her face in the Captain's sex, her mouth eager to please the domineering Drake. Ashlyn's body convulsed as Latesha's mouth lapped at her pussy, but she held her grip tightly on Latesha's hair. I couldn't imagine how painful it must have been for Latesha to have Drake support herself with the dark beauty's hair, but Latesha didn't voice any complaint. The only noises coming from Latesha were the wet, slurping sounds of a frenzied pussy licking. "Yesss!" Drake hissed with the black woman's face between her tanned thighs. "William, open my shirt and suck on my tits." I instantly obeyed as soon as Drake commanded me. Watching Latesha's tongue worship had pushed the last bit of self control I had left. Drake's open shirt was easy to push aside and I cupped one of her lovely, tanned breasts. I sucked her nipple into my mouth, and it only took three swipes of my tongue to get nipple as hard as my cock. With Drake's hands holding onto Latesha, I realized this was the closet I would get to Drake being in bondage. This excited me, and I mauled her firm breast with more abandon than I would normally use. My teeth pulled at her taunt nipple and my hand squeezed her round breast with a passion I was surprised I had. "Harder!" Drake commanded, and I wasn't sure which of us she was talking to. I bit down harder, my tongue flickering as fast as I could over her nipple. Drake moaned and her body jerked, so one of us must have done well. Eager to touch more of my usually untouchable Captain, my hand strayed over to her other breast. I cupped that breast firmly, relishing the soft jiggly touch of a good, large breast. I trapped her nipple between my middle and second finger as I cupped her, and my fingers squeezed around that stiff nub of flesh. While my hand was busy, my mouth continued to suck hard at Ashlyn's first nipple. The angle of the swing and Latesha's bound body made it awkward for me to ravish Drake's impressive chest, but I could care less. Latesha's temptation from earlier had aroused me to near madness, and Drake's body was the best substitute to actual sex I could get. The salt of the sea was on her breast, mixed with the salt of her sweat from today's war. I craved the taste of her on my tongue and the softness of her breast on my lips. "Enough William," Drake said, pushing me away. "Undo your pants and get behind me." My pants were off in a flash and I didn't even mind the stares of the female crew looking at me. Pure desire had replaced any possible thoughts of shame. Ashlyn leaned back in the swing while still holding on to Latesha's hair. By leaning completely back, her mouth became level with my cock, her breasts heaving in all their splendor. I didn't need a command to place my cock at her lips. As my cock sank into her mouth, I moaned loudly on the crowded deck. My knees were trembling from standing there, watching Drake suck me while Latesha licked her. I would have climaxed in a few seconds, but Drake used one hand to grip the base of my cock tightly. Once again Drake delayed my pleasure with her expert knowledge of my body, giving me the most intense blowjob I had ever experienced. I must admit, I was also immensely turned on by the group of women watching us. True, I was embarrassed by all the staring eyes, and the inevitable catcalls, but I was also aroused to be the center of attention. As Drake gave me the messiest oral sex I had ever received, I knew that anyone of those women watching would have loved to be in her place. "Have you ever fucked someone up the ass before, William?" Drake asked, her lips shiny with saliva. "No, Captain," I gasped. "Great! As your reward for being the one to capture our prize, you shall have the honor of violating her ass," Drake announced. Before I could answer, Drake released her hold on Latesha's hair and my cock. She climbed out of the swing, and replaced her grip on my cock with a stronger grip, and led me around to Latesha's ass. Drake waved Jeanette over to the swing, and the leggy brunette treated us to a show as she stripped off her long leather pants. Jeanette climbed into the swing and cruelly twisted Latesha's hair to make the damsel start licking. Meanwhile, Drake and I were standing at Latesha's red ass, her skirt still lifted over her hips. My pulse was racing. I was terrified and yet excited to be embarking on this new sexual position. As afraid as I was, I was soothed to know that Drake would be with me every step of the way. "Listen carefully, William," Drake instructed. "A woman's ass doesn't have the same lubrication that a pussy has. That is why I slicked your cock with my spit. Also, the ass isn't designed to allow anything to enter, so don't go in there humping your cock off. Go slow, be careful, and let me know as soon as your cock goes dry and needs more lubrication. Any questions?" "None, Captain," I answered. She released her grip on my cock, and I noticed that my near orgasm had gone away. It was no wonder. I was incredibly tense and nervous, conscious of trying not to make an ass of myself as I fucked Latesha's ass. Latesha's ass was a mixture of red welts and her own natural dark coloring. I hesitated as I tried to figure out how to put my cock in her, but Drake took over instantly. She spread Latesha's buttocks, revealing the chocolate colored anus. I held my cock and guided it into Latesha's tight ass. The sensation was incredible. Latesha's grip on my cock was stronger even than Drake's hand, but I had the advantage of being able to thrust. Drake hands moved to my ass and stomach, guiding the speed in which I entered the seductive ass. The heat from Latesha's welts felt hot, adding their heat to my thighs and crotch as I sunk into her plump ass. After an exquisite eternity, my balls met her cheeks and my cock was completely encased in her tight ass. Latesha's body shivered and she lifted her head away from Jeanette's pussy. "He's too big!" Latesha moaned. Drake wasn't convinced. "Do you want to use your safeword?" "No," Latesha said, and Drake slapped her on the ass, hard. I felt the impact as her ass tightened around my cock. "Then shut up!" Drake snapped. Jeanette twisted Latesha's braids in her hand and the complaining black beauty returned to her task of licking. I returned my attention down to the dark, plump ass gripping my cock so erotically. My cock had never been gripped so completely and tightly before, and I found myself loving every second of it. Drake sat on Latesha's barrel, watching me enjoy myself with a smile on her face. "Now pull slowly out, about halfway," Drake instructed. I did as she said, placing my hands on Latesha's ass to steady myself. Latesha jumped as soon as I touched the hot spots of her lashing, but she didn't complain this time. Slowly I pulled my cock out, Latesha's ass trying to push me out as I went. Those muscles pushing on my cock caused my eyes to roll with bliss. "Go back in," Drake commanded softly. This time I cried out as I entered Latesha, for her ass fought me every inch of the way. The pressure and resistance against me felt intense. I completely forgot about all of the women watching me as I sank my cock to the hilt. Though I never once forgot about my special Captain. Drake laughed at my shivering, and climbed on top of the barrel. With no regard for Latesha, the Captain sat down on her captive's back, her legs open and her sex a mere six inches from where my cock was entering Latesha. Drake gave no commands as she stuck her fingers into her glorious sex, and I needed none. I began the careful, slow, delightful task of fucking Latesha's ass while Drake played with herself. I wasn't sure who was watching whom, for I was hypnotized by Drake's glistening sex and the fingers that pumped her wet oasis. Drake was enjoying the sight of my white cock being engulfed by the dark ass. Occasionally, she would wipe her wet fingers across my cock as I pulled out. In this manner she kept my cock lubricated with her own excitement. My initial hesitation with anal sex was fading as my desire to orgasm grew. My thrusts grew harder and faster as I pumped the bountiful ass. The force of my thrusts was strong enough to make Drake unsteady on her perch above Latesha, but the Captain simply laughed as she nearly fell off. Latesha was groaning as I pounded her ass, and the way her hips kept undulating told me that she found the experience nearly as pleasurable as I did. My balls were slapping freely against her sex, and it was impossible not to notice how soaked her pussy was becoming. Finally my cock erupted inside Latesha's ass. The surge of cum traveling up through my cock was so intense it was almost an orgasm in itself before my REAL orgasm occurred. When my cum did explode forth, I felt it backwash against my cock, being squeezed out of Latesha's dark ass. I shut my eyes and let out one of the longest moans ever. Once again, my Captain had arranged for an unforgettable orgasm. "Pull your cock out," Drake commanded. "Cover her scurvy ass!" As my Captain rubbed her pussy faster towards her own orgasm, I did as she commanded. I pulled my cock out, and without hesitation, I stroked the remaining cum out of my cock. Latesha's buttocks quivered every time a stream of hot cum landed on her. My shame in front of the crew was forgotten as I tried to please my Captain. Only when Latesha's dark ass was decorated with my seed, did Captain Drake allow herself to climax. Drake doubled over and grabbed a handful of Latesha's dark, welt covered ass. Drake squeezed Latesha's ass, the cum oozing through her fingers. My Captain certainly doesn't mind getting her hands dirty. "Very good William!" Drake complimented. "Let's see how many more of my loyal crew this wench can get off tonight!" I retired back to the deck chair, my cock sore and exhausted. A cute blonde brought me another mug of the fruity punch they were serving. As the sun set on the deck of the "Saucy Wench," I watched as Captain Drake organized more feminine plundering of the captive Latesha. It took a few hours, a few bottles of lube and a lot of ingenuity on the part of Captain Drake, but at the end of the night, not a single member of her crew went unsatisfied. To be continued, <1st attachment end> ----- ASSM Moderation System Notice------ Notice: This post has been modified from its original format. The post was sent as an email attachment and has been converted by ASSTR ASSM moderation software. ----- ASSM Moderation System Notice------ -- Pursuant to the Berne Convention, this work is copyright with all rights reserved by its author unless explicitly indicated. +---------------------------------------------------------------------------+ | alt.sex.stories.moderated ----- send stories to: | | FAQ: Moderator: | +---------------------------------------------------------------------------+ |Discuss this story and others in alt.sex.stories.d, look for subject {ASSD}| |Archive at Hosted by | +---------------------------------------------------------------------------+