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By Air ((Private))

The woman whimpered as he forced her to stop everything. Her hips tried desperately to buck but they were stopped by the Captains powerful hands. This was cruel! Lillian gave him a truly pathetic look and pouted out her bottom lip. He was such a tease, to make her feel this way and then make her beg for it.

Her hand slid down and she began to rub at clit. If he was not going to offer her any relief, then she could get it on her own. Her moaning continued as she refused to beg anymore for him. A playful smile crossed her lips when she wondered how he would react to it.

Would he spank her? Whip her pussy again? Force her to take that cock down her throat once more? Then her movements stopped, an appalled look on her face. The idea of being punished was turning her on? It was repulsive! Her shoulders rounded.

“Please, master,” she said in a defeated tone. “Please milk my tits and fuck my pussy hard. Please?”
 
Jack's smile was even broader as he lunged for her tits, kneading and squeezing them as he started to suck her breasts. He knew she needed the milking machine, but for now, he was just going to take the edge off. She would be down to usually only needing the milking once a week with daily expressing from him, but for now he was using it as both a training and punishment for her insolence. He suddenly also thrust his pelvis, slamfucking up into her cunt as he sucked on her nipples. With his eyes gazing with Dominant want up into hers, he then started to really pound into her and forced her to bounce more.

"You're damn right I am your Master as well as your husband! I am going to keep all of my promises, Lilian, but you are going to learn that you will beg me for every fucking thing! You belong to me, and your own body is showing you that is true! As for what your eyes are asking, yes, you will be punished for your childish behavior, as not Captain's Woman gets away with such a immature tantrum!"

He did not tell her what he was going to do, as part of the punishment was for her to think about what he was going to do to her.
 
Lillian gave a sound of pure relief as he began to suck on her sore breasts. Milk came from them and the pain lessened slightly. A loud groan came from her as he slammed inside of her over and over again. It felt so good… it hurt so good. As he forced her to bounced, her heavy tits barely moved. Though it hurt.

“I am so sorry, husband,” she whined. “I will never misbehave again.”

The beautiful redhead shook her head and let out another moan. She was dripping like a faucet already, loud slapping noises coming every time he moved roughly inside of her. Without really thinking she began to ride him once more.

“Thank you for fucking me,” she whimpered, hating saying it. “You make me feel so good.”
 
Jack was very pleased, as Lillian was not able to deny her body like she had been any longer. He was really starting to truly like her beyond mere lust, as he did firmly believe in love at first sight. As she moaned and started riding his cock more, he suckled even harder on her breasts. Her body was embracing her need for pain as well as pleasure, and that pleased him even more. She had a high tolerance to pain, something she had to have been born with. It was refreshing, and that made him want to fuck her harder and deeper still, which he promptly started doing. He forced her to bounce harder. squeezing and twisting on her globes more as he also kneaded them with more pressure to force her milk out quicker. He kept his eyes on hers, pausing to speak more to her as he her words validated more what he already knew about her just from reading her body.

"I know you are sorry, Lillian, but you will misbehave because you will want what I have for you. You want to be a Good Girl for me, and that makes it better. I also know you do thank me because you have needed to feel this good for a very long time. I want you to understand that when I train you to fight as well as for being my Woman, you will be almost as lethal in battle as I will be. No woman who can handle what I am doing to you deserves any less than that level of capability, but you will be punished just as if you defied me and/or your body in our quarters, and don't ever forget that, my Ginger Girl!"

He slammed up inside of her twat even harder, his immense thrusts forcing her to bounce up even higher as well as landing on his cock harder and rougher. He like that it was causing more discomfort with him still sucking the milk from her breasts, as it arched her even more and pushed her limits more to his liking. He was going to continue her on the road to true submission to all he wanted and expected of her, and he was going to shield her sister from it if he could... and if she herself wanted to be.
 
Lillian whimpered louder as he expressed more milk. Whenever his head moved away from a nipple, the milk tricked down the side of her breasts and down her flat stomach. How incredibly sexy she must have looked to a man of his particular tastes. His thrusting was becoming painful but in a completely delicious way. The ginger maiden could feel him breeching a certain point inside of her over and over again.

“Never,” she managed to get out in a wince, “never will I forget who owns my body.”

An urgency built inside of her and she moved faster. It had become a familiar feeling in the past day. The woman knew what was happening. She was going to orgasm. Very hard this time, too. Her body tighten around his massive cock and she threw her head back in sheer ecstasy. Multiple spasms over took her small frame.

“I am going to cum!” she exclaimed. So close. So very close and then WAM. It happened all at once. A powerful wave exploded from her nether regions and Lillian collapsed on top of him, breathing harshly.
 
They were just beginning, as Jack used sex not only for lovemaking, but also for testing Lillian's endurance. He allowed her to collapse against him, allowing her to lay there and breathe. His hands slowly moved up her body, only moving her to arch her back and licked clean her breasts and stomach. As he did, he commented on her fitness with admiration.

"You are in surprisingly good shape, Lillian. This fact is one of the reasons that I chose you to be my Woman, and the other is that I suspected that you also had this much stamina. The key is endurance past when you are tired, my Wife, and as you admit I own you, your body is mine to push to the very edge of any limits you have."

He then had her on her back, kissing her ravenously for several minutes as he moved her to the edge of the bed. He was soon standing, her head over the edge as he pushed his cock into her mouth and down her throat. At the same time, with his hands gripping her thighs tightly and holding them open where he wanted them to be, he was eating her pussy. His lips, teeth, and tongue were feasting on her sex, while at the same time he was steadily pumping his hips to make his cock moved in and out of her throat.
 
Bliss. Purse bliss. His mouth was on her aching sex. There was no time to recover from her first orgasm of the day. As she moaned, she took a throat full of his man meat. It choked her and she forced herself to breathe through her nose. Though that was not very helpful as she was turned upside down. Nor was the fact that he was pumping into her mouth. Every thrust made her gag and bile rose in her throat. All the blood was rushing to her head, making it spin.

Thank goodness she did not eat much the day before or else she would have brought it all back up. Finally her throat muscles relaxed and let him in easier and deeper until he was balls deep. Lillian never imagined that she would ever be in this position and wondered if this was her punishment. There were doubts though. He would not be using his tongue on her sex.

It did not take long to bring her close to orgasm once more. Her body trembled and twitched and she tried to restrain herself so she could last as long as him. The redhead wanted to please him and have more endurance.
 
Jack then slowly down, almost to a stop, with both his thrusting into her mouth and throat and his feasting on her pussy. He wanted to prolong her status, and by preventing her from cumming he was doing just that. He had gotten used to his cock deep down her throat faster than the first time, and now he had his thighs holding her head in place as he wiggled and made the head of his cock move just at the opening of her throat.

"My Lillian needs to have her limits pushed and raised, and I intend to do just that to you. Do not worry about how many times I will force you to cum, because you will know you have really been fucked by the time I let you each and ever time."

He renewed his slower and torturous teasing of her pussy, using his cock to do the same to her throat as well.
 
This was worse than any lash could be! Lillian gave a muffled groan and tried to move her throbbing pussy out of the way. Now he was being mean for not letting her release that pressure mounting between her legs. Blood was rushing to her head and black dots swam in front of her eyes.

Desperately she whined, begging through muffled sobs to be allowed to cum. Roughly she moved her tongue around him, trying to goad him into finishing her faster. Perhaps if she showed that she was eager then he would allow her sweet relief.

The agony built in her sex. It was almost painful. Torrents of her juices flowed down her stomach from her pussy. Her cries became more desperate and demanding. How could he do this to his loving wife? This was unbearable! She attempted to twist again, to try and get away from it. Finally, in a moment of panicked desperation, her mouth accidentally clamped down harshly around the base of him.
 
Jack smiled, suddenly diving back into devouring Lillian's pussy with renewed intensity. He wanted a reason to punish her some today, and she had given it. He probed her pussy with his tongue, using his lips and teeth on her with ravenous gusto. He was not going to stop until she came in buckets, her flow like a river down her pubic area and thighs. He wanted her sopping wet, making his teeth scrape on her perineum in preparation for how he was going to rape her ass again. Only this time, he knew she would know that she wanted him to plunder her tightest of places. He growled in lust, ramming his cock down her throat and pinning her head town with his pelvis as he growled out loud.

"Swallow every fucking drop of my seed, my Beautiful Bountifully Big Breasted Bitch!!! Take your Master and Husband's seed deep down your throat and get ready for another gusher of an orgasm to drench your bowels!!!"

He was grinding his crotch into her face, making his very large balls slap her in the face. He knew she would know she would also have to suck his balls, and that would be an even deeper sign of her acceptance of her servitude and marriage to him.
 
More muffled cries came from her. Thank God he decided to speed up! Her body trembled and quaked as another orgasm overtook her frame. Without any pretense a large gush erupted in his face. All of her muscles relaxed. That was heaven. Deeper she was able to take him in until her tongue was eagerly licking at his sack. Now that she was finished she wanted him to hurry up. Being in that position was starting to make her head hurt. Her face was now a deep purple, the modified breathing and fact that she had been turned upside down had seen to that.

The black dots began bigger and her mouth clamped harder down on his member, her teeth brutally grazing the sensitive skin there. Lillian did not mean to cause him pain but she had started to panic more. Passing out under such circumstances was bad. What if she was punished for fading off? Another thrill of excitement went through her and she groaned at her own perversions.

What type of woman had she grown into?
 
He used his body to hold her head in that position for just long enough, his rolling and grinding into her throat for the express purpose of furthering his pleasure at that moment. He then growled into her twat, slamming his cock deep as he erupted into her throat with his orgasm. He arched his body just enough so that, when he was cumming, he was forcing her to swallow every drop.

"You are able to breathe now, Woman, so you better swallow my cum! I am still going to punish you for some of your impertinence from last night, so only if you want to make it harder on yourself will you refuse to! I am going to gape this tight ass of yours again, and then I will rape your throat! You better learn to understand that the Law of the Seas and Skies gives me right to your body and soon, my Wanton Wench Wife!!!"

When he was satisfied with what she did with his cum, he then would slowly pull out of her throat. Her ass was going to be sore again when he was finished, and that was what he really wanted right now.
 
Every swallow nearly choked her but she managed to get most of it down her throat. Some overflowed her beautiful pout and dribbled down her chin as he pulled out. Rough coughing shook her entire body. Bright blue eyes were look even brighter because of how bloodshot they were. Lily hated the way that felt. She coughed more, feeling sick and woozy. The idea of getting her ass stretched did not make her feel any better. She gave him a frightened look and tried to pull away.

“Dear husband,” she whined. “Dear husband. Please, have mercy on me. My bottom is still sore from the way you took it last night! I feel so loose and abused. Please, another punishment.”

A whimper came from her as she begged him. Gently she turned, trying to put her body in a different position, hopefully deterring him from shoving that horse like appendage roughly into her ass. She pleaded with him silently with desperate eyes.

“No,” she whimpered. “Anything else.”

Her begging was good but likely not the type he wanted to listen to. Lillian wanted to make sure he was pleasured but she was already so sore.
 
Jack was very interested, as she was proposing something very intriguing to him. His hand slowly moved up her thighs, getting her pussy and clit. As he squeezed and twisted her between his fingers, he smiled wickedly at her as he spoke to her.

"Yes... that could be a possible diversion. First, my dear Lillian, you have to show me that sparing your ass is a worth while endeavor. How you can do that is simple, and that is by telling me who you picked my ship. There were at least seven other sky clippers there, but you selected mine... that intrigues me."

He then rammed four fingers inside of her pussy, his eyes telling her that depending on how he liked her answer, he may still take her ass again if he did not like it enough.
 
Lillian bit her lip and look down at his hand. Her juices were coating his digits and it elicited a moan from her lips. He wanted to know why she chose his ship? That was an interesting question. One that she really had no answer for. At least not one that he probably didn’t want to listen to. The redhead pouted and shook her head and gave a pathetic cry.

“I thought no one was looking,” she replied in a small voice. “And I was getting desperate. I had never done anything like that before but I was too concerned with my sister’s well being.”

Then she got on her knees, moving away from his hand. She began to place soft kisses and tender licks on his manhood to show him how sorry she was. “Please, do not take my ass again. Another punishment. Please my dear husband, my master.”
 
Jack stroked Lillian's hair, knowing that she was speaking the truth with every word she was saying. He also knew that she had a very skewed idea of why he took her ass as he had been, and that really did need to change. He moved his one hand, easing two of his now fingers inside of her predestine clean ass. He knew it was no were near as filling as his cock was, but he was also stroking her anus and smiling.

"Lillian, I am not wanting your ass to punish you, though the roughness I give you is. Your ass is part of you you have given, and it is another place that my cock will go. As my Woman, my Wife, your begin is pleasing me, but you know that in the deep recesses of your heart, you want me inside of your ass again."

He held her close, not yet moving as he wanted her to understand he was not lying about his feelings at first sight for her. But he was going to have her as he wanted, and as he slowly slid a third finger inside of her ass, he was giving her a preparatory stretching as a reward for her fully and willingly submitting.

"I will detail for you all that I will teach you as part of my crew to get ready to help free your sister, and if needed, kill the man who stole her from you."
 
His fingers hurt at first. The flesh of her anus was still sore and sensitive from when he took her before. The stroking felt good though. It soothed the stretched and brutalized parts of her until she was whimpering from the pleasure. She listened to him, a bead of sweat going down her face and across the nape of her neck. Another finger was added and she knew then that he was going to try and make it easier for her to take his cock.

“Yes, master,” she whimpered. Her eyes shone with her submission and want to make him happy. This was sick. Just yesterday she had been fighting this sort of treatment with everything she had. Now she was begging for it like some depraved slattern. A third finger was slipped into her tight rosebud, opening it up further. “I will continue to learn from you. Accept all of your gifts.”

The beautiful redhead worked her body around so she was on her hands and knees. Even though she did not want to admit she liked it now, she knew that he would make it good. With her delicate hands she spread her cheeks widely, giving him better access.
 
After using a fourth finger to tease and stretch her ass, he pumped them a bit, soon extracting them and wiping them clean on a towel right before suddenly moving into position behind her. His legs pinned hers down like before, his hands moving to find her lovely smooth shoulders, firmly gripping them so that he was able to pull her back with a steady grip. He pushed with his pelvis, the head of his cock soon stretching her anus wide open as he groaned loudly. She was still as tight as before, but he felt her ass muscles accommodate him so much easier than the night before. He held her in place, rolling his hips and grinding against and inside of her ass for several minutes so that her hands were trapped against her luscious ass cheeks.

"So wonderfully taunt and tight, Lily!!! Just like that, you are blossoming into a proper Captain's Woman!! Remind me how big my mast is inside of your ass, and then tell me how much you want me to pound your ass until you whimper for release from the pleasure and pain you want me to give you!!"
 
Lillian let out a grunt as he made his way into her ass. Her body accepted him eagerly almost, the muscles in her back side pushing away easily as he pressed inside. It still hurt but she was not going to complain. This is what he wanted and she would force herself to like it.

As he moved she gave a moan, finding that she did not have to force herself to do much. With her face pressed against the covers she sounded quite muffled as she made her noises of passion. Her eyes closed tightly.

“Y-yes sir!” she managed as he pumped inside the tight canal of her ass. She bit down on the pillow and gave another series of muffled cries. It was good. Better than what she thought it would be. Her breathing became rougher and sweat trickled down her back as juices trickled over he legs.

“Mmmmmmaaaster!” she groaned loudly. “I love it when you fuck my ass raw! It is so good! Please, use it until I can’t walk!”
 
As Lillian grunted and groaned loudly, Jack rewarded her by doing exactly what she was asking for. He started to pound into her lovely ass as hard and rough as he wanted to. He was spearing into her ass with intense abandon, forcing her to bounce harder with every one of his brutal invasions of her deepest insides. He moved his hands to her large breasts again, and he squeezed them as tight as he could to make her arch back. He yanked her to him, grinding into her from behind with a great deal of wanton lust. He rolled his hips as well, wanting her to feel him deeper still inside of her tightest passage. He released and spanked her tits hard, only to return his hands to kneading them so very hard once more.

"Yes, my lovely Lily, you are going to have a lot of trouble walking, but you still will!! I will train you to fight and to use a blade, so you can kill the man who dared to take your sister from you!"

He slammed into her ass more, forcefully making her take him still deeper inside of her ass. He wanted to make her feel him all the way inside of her bowels, and that was the point. He wanted her to whimper in need, to plead with him to make his rape of her ass still more intense on her than she had already learned to handle. If he indeed punished her, it would be to force her to plead and bargain for him to renew his plunder of her ass with anything she could give.
 
She bit down harder on the pillows and her face turned bright red. He was slapping, pulling, and yanking at her breasts, making them hurt. Bruising would appear on her body, around her nipples, even on her knuckles because they were being rammed into by his hips.

He wanted her to learn how to fight after this but, oh! Lillian didn’t know if she was going to be able to do that. Her body already hurt so much and it was going to be so much worse when he finished. Not to mention, she had to go to the bathroom terribly. All of this brutal ass fucking had knock some things loose and she was fighting it.

“Sir!” she begged. There was a sound of desperation in her voice. “Sir, please! Hurry! I need to… need too…”

She whimpered.

“Just hurry!”

Tears swam in her eyes and she gave strangled cries.
 
He knew what was wrong with her, and she was misinterpreting what was happening to her body. But he was going to tease her just a little, pounding her ass more ruthlessly as he spoke to her.

"You are telling Captain Jack Blade, scourge of the Seven Seas and Skies to hurry? Are you not being a petulant Slattern now!! I give the orders here, and now you have to show me just how I should respond to your requesting me to hurry and why?!?!?"
 
Lily cried out more, feeling desperate now. Tears ran down her face. No more! She was going to do something that he would hate her for! This was too much for her to take! He had to understand. She tossed him a pleading look over her shoulder. Her whole body was trembling.

“Master, I am… ah… sorry!” she screamed. “But, I beg you, please stop. I need to go to the…”

She did not want to say it. It was shameful. She let out a cry. It felt good though. God, she it was disgusting but it felt amazing. She gripped to the covers, nearly tearing them from the bed. “Please, please, please!” Though, as he continued she was not sure if she wanted to go to the bathroom or wanted to cum.
 
He knew she was confused now, and he was going to correct her.

"You are not wanting to use the bathroom, Lillian, as I cleansed you thoroughly last night. I am gaping your ass, and you are needing to get used to it. You are going to cum, but only after you have pleased me more... in other words... beg more!!!"

He pounded her even harder, yanking her to him and forcing his cock still deeper inside of her ass and bowels.
 
Lillian felt hot all over. Was he right? Was this just how it felt when a woman was put through such things? Perhaps. She groaned and grunted more and bit her lip. Her breasts bounced against the soft material of the bed.

“P-p-p-p-please,” she whined, “harder, master. Please let me cum for you!”

The pressure was building between her legs. She was about to explode in passion as he caused her pleasure and pain. She bit down on the blankets and screamed into the muffling sheets. This was causing her to go completely crazy.

“Husband, please! Please! Let me cum.”
 
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