Jolly Roger1-4 updated

The Jolly Roger

Chapter 1

In the Caribbean seseaport Port Royal early July of 1687, as the warm trade winds rushed across the southern tip of Jamaica, the privateer ship The Jolly Roger slowly eased into her birth after a six week tour in which she had plundered three spainsh galleons.  Just off the helm stood the captain, a trim, dark haired man, and six feet tall with dark hard eyes.  He was liked by his crew, but they they also knew that crossing Captain John Capshaw could only result in a week in the stocks he kept in a private cabin next to his, where lashings by the large assortment of whips and paddles would be the kinder of the events that took place durring that week. Known throughout the port as a favorite patron of the wenches in the taverns as a big spender and tipper, he preferred the Dog Leg tavern on the main street that led to the port just 2 blocks down. Releasing his crew for a week of leave he gave strict orders that none of them were to return to the ship for the duration of the leave. This was his ship for the next week and he planned on taking full advantage of this week of no crew, alone with his Treasure.

He stepped through the door of the Dog Leg to find a fair number of his crew already getting into the swing of celebrations while the wenches from the brothel upstairs, eager to claim their share of the spoils early, clung to them. The captain was not interested in his crew or the wenches; he walked directly to the bar and ordered a round for everyone, and walked directly to the back room where the proprieter stood at the wash basin running a cool damp cloth around her neck.  Captain Capshaw said in a low pitched voice "It's been a long six weeks and I couldn't imagine a better a better sight to come home to".

She turned around damp cloth resting on her luscious cleavage, she was as beautiful as he remembered as she replied with "I was wondering how long it was going to take you to get here.  Your crew is half way to being three sheets, and I was under the impression that you were in a hurry to get back to me?" She had a petit frame with dark hair and eyes that are the color of a dark whiskey, but that burn with an intensity and passion that pierced his soul.  She was 5’ 4” tall and more beautiful than anything on this world to him. He could not take his eyes off of her, her perfect breasts lifted up to mounds of cleavage blossoming from her corseted torso.

He answered her waiting stare with "My treasure, I was making some arrangements for the next week, during which you will have no work to do as my cook will be minding the tavern, and all you must do is pack your bags while I prepare our livations for the week".

Curious, she asked what she should pack for and his answer that she “Only needed the items required for a week of passion and pleasure”, made her very intrigued.  She had never gone away with him before, even though they had spent every moment they could together over the last year.  He crossed the room to wrap his arms around her, lifted her to him, unable to restrain his mouth from taking hers, his lips touching hers their mouths part, heat built up from the last 3 fortnights finally finding a little release. Their tongues dancing across each other, her body pressed to his, after a few moments he released her and said "go pack my treasure"

She retuned down the stairs 20 minutes later with a large bag and said that she was ready to go. Capshaw had 2 of his men take the bags and they headed out for the Jolly Roger.

As they boarded the Roger, the captain told the guard crew to prepare to take the ship out. They set off 30 minutes later and, after an hour, they weighed anchor just off a small island.  The captain set the remaining crew off in a dingy with instructions to return in a week, with a stern “Not a moment earlier” added for good measure.  His treasure was in for a week she would not soon forget, and he hoped, would take her to places of pleasure that she had never let herself go before.

Finally alone with here, he walked to her and taking he in is strong arms they kissed and caressed each other, his hands on her face and neck, her breasts restrained by her corset; needing to kiss them, he slid his hands down to her hips and turns her around. He reaches around her, kissing the back of her neck, slowly unbuttoning her silk blouse, one button at a time. Taking an excruciatingly long time, he finally reaches the last button, to her agonizing relief.  She needs to touch him as bad as she needs his touch; her hand reaching behind her to find his manhood that she has been aching for since the last morning 6 long weeks ago.  Just as she finds his hardening shaft, she feels his hands at her neck and in a seductive yet commanding tone that he has never used with her before, whispers "No My Treasure, you are to be mine today, you will not reach or take or do anything without my permission.  You are on my ship, and on my ship you do as you are told.  You will only speak when spoken to or after you ask permission to speak or act, and will do neither until I have granted you that permission.  You will not act or assume any prerogatives.  Do you understand my treasure?"

They had been together many times over the last year, but never on his ship, he had always come to her, and had always been very giving and gentle when she wanted, but would take her when she needed it. But today it was different, he was so firm and controlling and a little terrifying, but in the last year he had never hurt her, or given her any reason to fear him. Confused, but excited, she was battling fear and her need for him, both so strong, but after what seemed like an agonizing eternity her need won out, so with a tremble in her voice, she replied with "Yes, My Captain".

As a reward for her obedience he cupped her now corset only clad breasts squeezing the firmly nibbling her ear and neck, his hand sliding down her abdomen to the waist band of her skirt and slipping inside her pettycoat cupping her woman hood through her black silk panties he pulls her back against his pelvis and even through all her layers she could feel his hard shaft against what he considered her perfect and incredibly sexy derrière.  He massaged her sweet mons, his mouth devouring her neck, his other hand kneading her now extremely sensitive breasts through her lace corset.  As she ground herself against his hands, her sweet nectar now covering his fingers through her silk, she started climbing up to her release and was getting closer by the second; and he could tell.  Just as she was about to feel the sweet release fighting her urge to touch him, no matter how bad she needed to, she could tell he was serious about his command to her and she had to obey, but just before the first wave of pleasure hit he stopped his touching and only kissed her. She didn't realize she had done it, but a whimper of frustration slipped from her throat, and that's when she found out what the rules really meant for this day...

Chapter 2

He didn't hurt her, or even appear angry in the least, but grabbed her wrist and led her to the hatch leading to his side cabin with the stocks and with a terrified voice said "What are you...”

But he cut her off and said "You are mine on this ship, you will not utter sighs of displeasure with what I choose to do with you today, and my rules stand. If you want to speak you will ask my permission. Do you understand me Treasure?"

Now completely unsure what was going to happen to her, she knew she belonged to him at this moment, and had to obey, and her tone told him she did finally understand she was his when she answered " yes my captain, I understand now".  She could not control herself, she had to be his, and she had to give herself to him. 

He was so turned on and knew she was about to be taken to places that she had never been before, and he was going to teach her to release all of the control she usually fought to maintain.  He was going to take her to paradise in this room so often reserved for torture and was getting anxious, but he knew he had to take this slow and remain in control to let her give up all of hers.  He had been planning this moment since his last night with her a month and a half ago. She had given herself to him many times, and he loved every moment of it, but she always retained this control keeping her self in the moment instead of letting the moment take her. She always came for him many times, and always was so ready for him, but never let go, afraid of his reaction to her letting go and afraid she couldn't come back if she let herself go.  So he knew then that he was going to have to take her there to give her this gift of ultimate pleasure that he so desperately wanted her to have. So after a moment he said "I must punish you for breaking the rules, but you will see shortly that I do this because you need to feel what you are capable of feeling. Now I know you are scared, but my crew trust me as their leader with their lives in battle, and now you must trust me with your heart so I can take you to the highest levels of extacy that you deserve".

Now she was scared but not as much as she had been as he removed all of her clothes tenderly but still firmly in control she remembered the rule this time, not wanting to add any more to the punishment she had already earned, and asked "captain? May I ask a question?"

He replied "yes my Treasure you may"

"What is my punishment" as her silk panties, she had purchased just for this day, fell to the floor and his hand cupped her, his finger parting her smooth lips, sending a shiver up her spine. Finally his skin of his fingers found her pleasure button and the flesh on flesh sensation brining back the excitement in an instant.  She began to moan and immediately covered her mouth to stop it, but he pulled her arms away and said, “You my express pleasure My Treasure”, and began to drive her over the edge with his fingers. He told her to cum for him now or he would stop and begin the punishment immediately, his fingers flogged her swollen, tingling, and throbbing nub, and were driving her to release. He repeated his command and that was all she could take as waves of pleasure rolled over her. He ears pounding with her heart beat, but she kept her composure only moaning quietly.

Once he had eased her down he removed her corset leaving her naked. He told her to remove his shirt and she eagerly said "Yes My Captain" and obeyed with shivering fingers and slightly woblely legs. Then he told her to remove his boots and pants. She obeyed immediately and asked "Captain? May I please kiss your manhood?"   

He replied "you may, but you may not take it in your mouth unless you bring yourself off while you suck it."  The look on her face was obvious that she didn't want to touch herself, but she wanted her captain in her mouth so bad that she would do anything he said to have him, so she said “Yes My Captain.”  She took a moment to look around and led him to the matress in the corner of the cabin, got down on her knees and began to lick his shaft, he reminded her of his order.  She parted her lips and though her touch could never compare to his, she began teasing her lips as his hands grabbed her short hair urging her to take his throbbing shaft, as her fingers found her clit she moaned, and wanting, no needing her mouth around him, she eagerly opened her mouth and took his head into her hungry mouth.  While trying to focus on him, her own fingers were so distracting that she eased up so she could focus on him. But as soon as she did he pulled her back by her hair and said "Today is about you not me Treasure.  Now you must cum before you can have me again. Cum now treasure or the punishment starts"

Defiance in her eyes said no, but she began to rub faster and harder she uttered out "yes captain" with a shaky breathy voice that drove him wild, making him visibly harder than before.  She was so wet with his hands gripping her hair, and her fingers on her pussy, but the biggest torture was him, the thing she wanted more than anything at this moment just inches from her mouth, but she knew she could not have him until she followed her captain’s orders, that much was clear on his face.  She could see his want, but could not understand why he would not give himself to her.  As if reading her mind, at that moment, he took his free hand and began stroke himself in front of her face. Never releasing her eyes from his, but it was still confusing to her.  She could see that it wasn’t cruelty, it wasn’t to be mean, but her need and her own touch and his touch and what she was watching began to push her over, and at that very moment she began to cum.  He grabbed her hair tighter and pulled her mouth onto him, he began giving her orders again, “cum with my cock in your mouth!”, “Don’t control it! Let yourself explode!”, “Suck me harder”, “Feel your self letting go!”  She could not control it any longer; she began to gush her sweet nectar in her hand, soaking her thighs, and the mattress below her.  He loved her giving herself into the moment, and he was going to reward her, but she still had punishment coming, and could not let her get out of it.  He decided to give her both though.  He spoke to her slowly “Do not stop rubbing your self or cumming, but, I am going to cum for you.  Do you want me to cum in your mouth or do you want to watch me cum on your chest as you explode for me again?  I will only cum for you as you gush for me even harder than you just did, let your self go for me.  Now as you rub release me and give me your answer Treasure.”

Her excitement at this nearly drove her over, but she stopped long enough to answer “My Captain, please let me taste you” and she began to stroke him harder and faster with her mouth while at the same time flogging her clit, driving her self harder and faster than she ever did when she fantasized about him while he was gone, but the moment finally had her, she didn’t want to control herself at this moment.  She was giving herself to her pleasure and he was swelling in her mouth as she was moaning around him.  He had her hair in his hands and was thrusting his swelling manhood faster and faster in to her hot mouth.  She could take no more and her orgasm overtook her, harder than she had ever cum by her own touch before her cum blasting from her womanhood almost screaming around his cock and that was when he exclaimed to her that he was going to give her what she wanted more than anything “I am going to cum hard! Suck me hard Treasure!” and that is when he exploded in her magical mouth.  She could not control the orgasm in her as his hot cum filled her and she just opened her mouth wide to catch all of it while moaning with pleasure.  She was driving him wild but he knew he was going to have to give her a break, or she was going to start to control the moment again.  As she knelt there shaking and shivering with pleasure swallowing her reward, her legs tight together but her hand still cupping her beautiful pussy.  He told her “You can have a break or she can take her punishment now what is your choice My Treasure?”

Chapter 3

Her answer had not completely surprised him; he could tell that she was beginning to understand why he was taking the control. She was still quivering and shaking as he helped her to her feet.  She was slowly gaining control of her legs again, but by no means was she steady yet as he wrapped her in his arms and walked her over to the stocks that were padded this morning under his orders, knowing he would have her in them before the day ended, he wanted her soft body protected from scars, if not from the pain that would take her to pleasure. She was still aching and ravenous for his touch; she didn't understand why what was happening excited her this much.  The one thing she did understand at this moment was that, as he was gently placing her wrists and neck into the stocks, was that she belonged to him, and more importantly, with him. As he locked her into place the combination of fear, and excitement, along with the trust she had in him; created a potent need in her loins that she couldn't control.  She spoke softly as she said "Captain?"

He replied with "Yes my treasure?”

"What is my punishment exactly?"

He answered "You will find out soon enough sweet treasure" as he slowly caressed her bare buttocks. “Soon enough indeed" he said as his firm open palm spanked her with just the right amount of sting to send her reeling with pain and pleasure.

He walked around to the other side of the stocks dragging his nails up her back, sending ripples of pleasure up her spine, knelt down so she could see his face, and kissed her softly on the forehead.  After he kissed her he whispered into her ear “Treasure, this is your punishment” and with that he covered her eyes with a black satin cloth, plunging her into darkness.

She was suddenly aware that the one sense she could use to follow what was happening to her just disappeared.  She wasn’t sure she could do this, but she knew she had to.  She now knew that she was completely out of control, and suddenly it was very liberating.  Her Captain was caressing her back and thighs and teasing her swollen mons and teasing her clit.  Just as the realization of how liberating this was…she saw stars and her ears were assaulted with the loudest smack she had ever heard and her bum was stinging like nothing she had ever felt, and she realized the yell she heard was coming from her own mouth.  As her mind caught up with her body, she grasped that she had just been paddled…HARD…but not so hard that… and then there were his hands, slowly caressing and rubbing.  So soothing and gentle that she didn’t know how to react.  She was loving his hands and arching her back, pressing her ass to his hands as he gripped her soft yet firm cheeks.  His hands slid up the side of her hips and then gripped them tight, pressing himself up against her, while pulling her back against him.  She realized he was no longer wearing his pants and his firm manhood was resting between her buttocks, and a new rush filled her.  She was tingling and throbbing so intensely that should couldn’t take much more.  As he backed away leaving her wanting she felt all the strips of leather from his cat of nine tails she had seen and hanging on the wall moments before.  Her Captain whispered into her ear that she “could ask to be excused from her punishment this one time, but she had to claim it now, there would be no second chance, now or never my Treasure” She was so turned on that her response was immediate, “No Captain, I broke the rules and I deserve my punishment, but may I ask that you take me in these stocks after?  Please my Captain?”  He said that he would consider it before her senses were assaulted as the cat tail stung her cheeks for the first time, she let out a yelp, but she loved every second of it.  Her captain said that she could let out sounds, but could ask no more questions, only accept what was happening.  If it hurt too much she could speak, but only if she was prepared to not relinquish her request to be taken while captive in the stocks.  That was her last remaining chance to return to her life as she had always known it with him.  She knew that she needed to be taken in this place, in these stocks, more than she had ever needed anything before in her life.  She said “yes, my Captain".

Before she could prepare, the next swath of the cat tail came down sending her further into ecstasy as she moaned softly biting her lip.  Then the next, and another, and then his hands rubbing and caressing again.  She was reeling and out of control with want…no…need, she needed this, and as she was waiting for the next strike, she felt his hand cup her now dripping pussy.  This sent her over the edge, the waves crashed over her as his finger found her clit driving her deeper into the onslaught of waves taking her away.  Then as she was beginning to come down to catch her breath he found her entrance, parting her slick lips, his middle finger slid deep and began to massage her g-spot.  Her next orgasm assaulted her and as he was working her she lost all control, her orgasms were usually intense but this was something she had never felt, she could feel streams of wetness down her thighs with every pulse of pleasure.  Her captain was loving every second and could take no more.  He gripped her hips as he pressed his head against her swollen lips, she felt it and arched as she backed against him, staining against her restraints.  He was only letting her have the head, she needed more, more, more… and then he pulled back from her, and as the low moan of disappointment escaped he lips, her entrance convulsing in expectation... she was assaulted by a blinding flash of light, the crack of the leather exploding in her ears like a cannon had fired through her brain. She couldn't think; all control of her body was gone.  She desperately tried to understand what was happening. Pain, pleasure, lust, anger, and desire racing through every single nerve ending of her body colliding into each other as her skin was on fire. She was lost in a moment so intense that she was screaming in pain, but over the pain was pleasure she knew could only be his doing.  With control fleeing her mind the sound of"capta..." escaped her lips, but before she finished the next explosion raged through her entire being.  He spoke, as his hand gently glancing across her raw flesh, "Did you say something my beautiful Treasure?"  Panic struck her. She almost answered, and her desire reminded her of the rule against speaking. "Mmm mmm" shaking her head as much as she could in her current confines.  "Good Treasure" was all he said. His calloused hands torture on her now bright read ass. His hand left her skin and before she could fully brace the next eruption had her in a grip she almost didn't understand what the sudden pressure against her clinching entrance was. He was behind her again; his swollen throbbing head was inside her again. Would he let her have him, all of him, and as he plunged she lost all sense of anything but pleasure, she was no longer contained, he was thrusting, deep and hard, long mind bending strokes of heaven as his hips  drove into her, he pulled her onto him over and over. She was lost.  She could only scream and quiver as his body drove hers.  She felt him swelling inside of her, and she knew that feeling all too well.  She could tell when he was going to fill her, his shaft and head always swelled in the moments before her was going to cum.  She loved that feeling and she needed his orgasm.  She was bucking with him when he moaned as she felt him explode inside her, sending her over again, but this time she exploded, she could only see stars, and hear the blood in her ears.  This was more than the last, she had never let go like this.  She was aware that her thighs were soaked, but was still in the middle of the best orgasm of her life.  She felt his hot cum filling her in burst after burst.  She was clinching so tight around him, still exploding, but the intensity was waning.  She finally came down as she felt him drape his body across her back, still inside her; they were both panting and sighing.  He wrapped his arms around her as he slipped out of her insanely wet mons.  He released the stocks and laid her on the mattress and lay down next to her.  She laid her head on his chest and said only “My Captain” and drifted off to sleep in his arms.

Chapter 4

She awoke in a haze; there was no light, her mind trying to recall her last conscious thought, her skin damp and cool. As she tried to move, the sting of her punishment lead the onslaught of recollection. Her mind flooded with every sensation and feeling of the day before. She reached for him in the pitch black cavern to no avail in the black murkiness.  That's when she realized she was still blind folded, sitting up, lifting the fabric off she was startled to find him in front of her wringing a cloth out over a bucket beside him. He smiled as he turned and placed the warm cloth over her breasts and said "lay back my treasure and relax".  She complied with out a second though he continued to softly bathe her with the soft cloth, the warm water and cool air combining to raise goose bumps on her arms. And as he slowly caressed her breasts she became aware of the candles burning all around the room, her instrument of yesterday’s punishment and soul electrifying pleasure casting a shadow across her face. She was thankful for that, her body sending reminders of both extremes she wouldn't be able to hide from him if it weren't for that fortunate shadow. Enjoying the carressing of his surprisingly gentle hands her body betrayed her, as he was now washing her breasts, she couldn't stop the quiet moan of pleasure when the cloth brushed across her nipple.

He possessed her now.  They both knew it.  How could she let him posess her as he would a targeted ship?  A flash of anger that many a wayward crewman had experienced first hand, and none would ever forget, erupted as she sat up screaming in a voice she had never heard before "I may be on your ship Captain!!" she hissed at him "but I'm not one of your crew that will just blindly follow your commands!!!  This ends here and now" she spat at him as she tried to stand.  He stopped her just as she had gained her feet by grabbing her hips, and in a motion she couldn't counter, pulled her to her knees facing him, not an inch separating them. "My dear Treasure" he spoke in a voice that was so calm and steady that her anger grew by the syllable "you are not my crewman, you are my Treasure, and as any true man of my possition will tell you, a Captain can not posses a Treasue the likes of you.  You must give yourself to me because that is what you desire, not because I say it will be. I am only your Captain because you are my Treasure." And with a look she recognized all to well on his face he spoke softly as he looked into her very soul and said "My GREATEST TREASURE". 

Her anger meted and was replaced by a feeling of foolishness, how had she forgotten that he hadn't taken her, in so much as she had given her self to him. She knew how this apology would end and decided that words were just words with one exception, and she spoke them so softly he could barely have heard them as she looked into his eyes and said, "My Captain".  In that moment aboard the Jolly Roger she realized that she was his Treasure and they fell to the soft bed together intertwined with each other.  Passionate doesn't come close to describing the next  few hours with her Captain, they kissed softly at first enjoying the electricity of every brush of their lips, every tease of each other's tongues.  She felt the first wave of heat taking control of her body, tingling exploding in a wave from her ears to her nipples to her now swelling clit. Zipping around her body she felt him expanding against her, their bodies pulled so tightly together by the grasp of their arms that she could feel his heartbeat through the now rock hard erection throbbing against her already wetness fighting to be in her, one with her. Their eyes locked as she wrapped her legs around him pulling him inside her as deep as she could. The desire and need taking them both him above her beautiful body was a sight she wanted, and more important than anything at that moment, needed.

His hips thrusting in time to the spurring of her heels at his back; her clit grinding against him as his steadily increasing speed and depth forcing her entrance to grip him tighter with every long stroke. Her breasts against his firm chest sculpted by years on board his ship she was going to cum, and she was going to do it while making love to her captain; and with that the first wave crashed through her as he drove himself deep inside of her in a single smooth plunge.  He could feel her orgasm ripping through her quivering entrance; gripping his rigid shaft at its base so tight that every single movement he made began a new spasm around his shaft.  She was riding wave after wave as their embrace was so incredibly close, her breasts against his chest their heat causing them both to sweat allowing her nipples to glide across the patch of hair on his chest; teasing them with the friction.  With every slow deep thrust they made together causing her g-spot to swell; tortured by the rim of his head grazing, no, grinding across it so intensely that she was having full body convulsions.  The glorious part of this was that in order to feel him pull out across her g-spot he had the thrust back inside her; and every time she raised her hips to accept him causing the head to grind around her cervix so very hard. The rhythm was amazing for both of them, but the repetition of g-spot as he pulls out, her entrance closing as the head of his throbbing shaft slides all the way out, then parting her lips, then entrance, then g-spot on the way in, then grinding her cervix, at the same time her clit pressing and rubbing against his pubic bone.  This whole pattern repeating itself step by step, over and over and over every few moments.  His arms wrapped around her back gripping her shoulders pulling her all the way down on him.  She was gloriously trapped in a chronic orgasm, unable to breath, but not willing to stop, she needed what was about to happen. 

He could feel every single ridge on her g-spot as he pulled out of her, and again on the way back into her.  It was incredible, the entire front wall of her pussy was swelling so much that it felt like every time he withdrew from her he wasn’t sure he would be able to get back inside of her.  His Manhood swelling and throbbing with each stroke; finally unable to take any more he stroked deep inside her on more time and began blasting her cervix with shot after shot of his hot sticky cum sending her to a whole new level as he started flogging her clit with his fingers as she greedily gripped his cock with her now squirting orgasm…