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By Air ((Private))

Jack growled and groaned, holding Lillian's head even tighter as he came, his cock erupting inside her throat. As his orgasmic lava pulsated down her throat, he then had the Machine back off slowly so that as he held her head so that she had to gulp down his cum. He slowly backed off just enough, reaching first for a rinse she could use for her mouth, then giving her water as he held the glass for her to sip out of. When he knew she had enough fluid, he caressed her face and hair, kissing her with nd almost loving passion, relishing the taste of her mouth.

He then slowly bound her breasts, making certain the leather was nice and tight all the way around them. He watched her eyes the entire time, wanting her to understand just how much he considered her his already. He eventually tied the ends in a tight bow in the middle of her cleavage, spanking her tits hard before moving with his still wet cock around her as he spoke to her about the enzyme more.

"It is water-based, the base of the enzyme, but it has to be washed off with water first. That means this divinely tight and supple ass is still very lubed.. however.. just in case..."

He gripped her shoulders, ramming his shaft home inside of her pussy. He pounded her twat very hard, making her feel his cock balls deep every thrust. He then suddenly pulled out, pressing the large plum-sized head of his cock at her anus. He pushed, invading her with a full third of his shaft as the Machine took the gag off of her head.
 
A thick stream of copious spunk was shot into her throat. It felt as if it were choking her! She sputtered and hacked as she was forced to swallow every last bit of his salty seed. There was certainly a lot of it. Finally it ended and she rinsed out the taste of her juices and his cum. The water was something she was grateful for. She swallowed the liquid with large and eager gulps. Lillian wanted this to be the last of it and that he was sealing this session kiss.

That was a thought made is desperation. The captain was not so kind. Without a word he started to use the leather strap to bind her breasts. Her discomfort grew the tighter he made it, a terrible and painful pressure building behind her nipples. She gave a loud squeal as he slapped her bulging breasts. Again a red mark rose on her supple skin.

He went on, explaining what the concoction was on her ass. Quite clear were his intentions; he was going to shove himself up her behind. Before though he rutted painfully in her sore and battered pussy. She closed her eyes tightly as the head of that monster was pushed inside of her. Even with the lube that allowed her to be entered easily, there was still pain. As soon as the gag was removed, she let out a whimper. “Nooo!” she begged. “Not… not there!”
 
Jack pushed more of his monster into Lillian's ass, loving how tight she was there and continuing with what he was doing. She was tight but stretching around him more, though she was responding as he wanted her to, he was surprised by the lack of blood from his stretching her anus. There were spots of red, but her own body was wanting it so much, she was more relaxed and that was going to help his training of her.

"We are going to get your entire body nice and educated, as the training will not just be in you learning to enjoy pain, but to also relish and crave pleasure through not just your twat, but also your throat and ass. All of your body will become addicted to repeated sessions of this kind, and you will learn to whimper and beg for what you want, like a proper Captain's Woman. I will train you to fight along side me, but never forget that I am the only one who commands and possesses you!"

He soon bottomed out in her ass, holding her by her tits and grinding into her ass hard and rough. He then started to spank and slap her breasts, thighs, pussy, and ass, asserting more and more that he was in total control of her body.
 
Lillian bawled as he pressed himself further inside of her. It hurt so bad! He had no idea what she was going through! Her ass stretched to accommodate the massive knob of meat forcing its way into her anus. Some of her skin in that area ripped. “No more!” she begged and whined. “Please! No more! Please! Please! Please!”
She went on like that until she was unable to do so and the only thing she was able to do was let him do it, resigning to her position.

The words rolled over her and she focused on them this time. This was her lot in life from now on. She was to obey him and revel in pain, beg for pleasure, and be used for his sexual needs. There would be a reward; he would teach her how to fight so she could save her sister. For her sister… she reminded herself why this was happening; because Lillian had to go out and play the heroine.

“Y-yes sir,” she finally muttered. Though her attitude was completely changed as he started to spank and slap and her. With how tightly her breasts were bound, the hits came painfully to them. She cried out and wept. The pressure behind her nipples became worse and her breasts were slowly turning red and shiny. A small, hot trickle moved down the underside of her right tit. Her left followed suit quickly. What was going on?!
 
Jack felt it when Lillian's globes began to express, and he was ecstatic as it was something he wanted from her. He was very much prepared for it, as it was an effect that the enzyme compound was prone to causing in females. He moved and wiped each nipple with a pair of fingers, and he tasted the sweetness of her breast milk and laughed as he continued to bugger her ass. As he really began his thrusting, he leaned in more to let her know what was happening to her.

"You are a real woman now, my Lily! You are expressing milk from these enormous jugs of yours, and I will make the most of that! I am going to keep you producing, as the pleasure of suckling from your tits is something very pleasant in my mind and heart! I am going to make your globes heavy, prolonging letting you express as part of your punishments when needed! There will be times your torpedoes will be so heavy you will cry to me to relieve them for you!"

He started to move her so that she was upright on the frame, moving her so that he could withdraw from her ass and turn her around. He then had her facing him, bringing her back down as he entered her ass that way, letting her see she was not really bleeding at all. He took a knife, teasing her nipples with the tip as he taunted her a little.

"You had to have felt them getting full, so I will let you choose. I suck them so they are less painful now after I cut off the leather while you thank me for taking your ass as well.. or I leave it on, and you beg me in front of others to alleviate them!"
 
Her cheeks burnt hot went he pointed out her lactation. The binds on her breast made more trickled from her sore nipples. Horror flashed in her eyes as he lapped at his fingers covered in her milk. He was going to force her to produce milk on command? From what she heard from woman breastfeeding, it is terribly uncomfortable and sometimes painful.

She was spun on the machine to face him, no longer having to force her head to look at him. Again he entered her ass. It took him easier than before, though there was still some ripping from being taken in the new position. The knife flashed and she gave a moan of pain as he teased her lactating nipples with the tip, making more of her milk come out.

Both if his choices sounded repulsive to her. But she did not want to be seen by other people as he suckled on her chest. Tears rose to her eyes. This was horrible. Yet he was right. She wanted relief. Her breasts felt as if they would explode. “Now,” she begged him. “Please, sir. Now!”

She let out a cry. How disgusted with herself she was! This is what she was reduced to. Begging a man to suck the milk out of her tits so she could feel better.
 
While Jack continued to pound up into Lillian's tight ass, he started with her lovely tits. He took her right globe into each hand, and using the technique similar to how cows were milked, he started to force her breast to express. At the same time, he was suckling on her nipple, nibbling as he did so that she knew that he was liking every moment. He also know that with as sensitive as her jugs were, she was going to start liking what he was doing to her.

He kept his eyes on her the entire time, flicking the nipple with his tongue to stimulate her into keeping her nipples rock hard. He really was loving sucking her milk right from her breasts, and he slammed up inside of her tight ass even harder and he did. He seductively suckled, sometimes on purpose only kissing and licking so that he could make her release noises when he stopped drinking from her tits.

His plan was to make her beg and whimper, to break her out of her haughty illusion that she was some kind of special woman. She was a woman, and special as well, but not so special that she was immune to the dark desires that all women have. As he rolled his hips up into her, making her pelvis and scrotum rub and grind against her pussy, he suckled more of her milk in his determined desire to make her kneel before him and accept being his Woman.
 
Lillian let out a moan as he started to pull at the swollen breast. It felt good to have that pressure relieved. As he nibbled and sucked on the producing tit, she continued to make those delicious noises of pleasure. It was so good. Even now she could not deny it. Mixed with the way he filled her backside the redhead was hardly herself anymore. Everything was mixing into pleasure now. More of her pleasure leaked down her thigh.

This was too much for her. Not a fourth time! He could not make her burst again. Not from doing such vile and ungodly things to her. The stowaway bit her lip to keep herself from groaning but it didn’t work.

“T-thank you, sir,” she managed to grit through her teeth. He wanted her to thank him for taking her in the behind. “Thank you for fucking my… my …mmmm… my ass!”
 
Jack smiled with wicked glee, knowing that Lillian was starting to submit, all be it begrudgingly. As he continued to slammed into her ass, he became more aggressive with his milking of her tits. He suckled and nibbled on her nipples, looking up into her eyes as he did. He was expressing more possessiveness of her, and he used one hand to spank her pussy every once in a while.

He was growling and groaning, spearing up inside her tightest place with greater roughness. His Dominance was rearing its head more, and he nibbled a bit harder on her nipples as he did so. He was already starting to mark her body, and he was not going to stop. She was already his Woman in his mind, and he was going to convince her that it was going to be a great thing for her.

"I know you do not really mean it quite yet, Lovely Lustful Lillian. That will change, however, as my intense sodomy of your ass will intensify the way you expose your own deep desires."
 
Lillian was going to cum again. There was no denying it, though the redhead wanted it to come again. The pressure was building up everywhere and there would be no release of that pain unless she let herself succumb to that sweet sinful climax. Her moans became louder as he spanked her bare pussy and completely rammed himself into her tight hole.

Milk ran down her stomach from the nipple he wasn’t attending to with her mouth. Lillian wondered what she looked like right now, bound and covered in her own lactation. Probably like a slattern. How did she allow herself to be tressed up like this? She did not know and at that point did not care.

“Please,” she whimpered pathetically. “Please, sir.”

Her head lolled to the side and she continued to moan. “I’m going to cum! Sir!”

Every muscle in her body began to tense and she gasped. “Please! Let me cum!”
 
"Yes, Lillian.. you beg so sweetly, so you may cum, and come now!"

He licked the milk off of her abdomen, wanting her to feel his magnanimous side as well as his harsh side. He would cum with her the minute that she came hard and long, and he was more than willing to make the intensity of it all the most important point. He was breaking her to his satisfaction, but she was going to also learn where she was really strong. She was not going to be able to resist what she wanted and what he wanted through her needs and desires, and it was something he really was going to relish.

"That's it, Lillian, my Woman.. relax and lets let the professionals handle our problems... such as like this from the finest machine builders in modern medicine."

He then pushed the two cups over and around her tits, turning it on and letting it do its designed job. It massaged and kneaded your jugs, and made you express your breast milk as he intended for her to fill both of the containers for later use.
 
And the redhead did. A powerful spasm took her body and she let out a cry, her ass muscles tightening around him brutally as a gush issued from between her legs. Her body went as limp as it could being strung up as she was. Her breathing was rough and her hips jerked again as a series of smaller gushes fell from her legs. “Thank you Master,” she whimpered as she breathed. Lillian really meant it to. Finally. Relief from the constant sexing. Perhaps he would even let her shower.

But he attached her to a machine that needed and sucked upon her breasts to make milk flow from them. She let out a high pitched little gasps. It felt good as the pressure was almost completely relieved. The canisters began to fill and were nearly overflowing when the final bit of milk was squeezed from them. She looked up at him, now the suction was hurting her.

“Please, sir, remove them?” she asked through gritted teeth. “They’re starting to hurt me.”
 
With her twat flowing like Niagara Falls, he slowly and teasingly removed the cups from her tits. They were still very firm and pert, but they were now red from what he had done to them, and that was very pleasing to him and immensely arousing as he kissed them and softly licked on her nipples. He knew she was going to be superbly sensitive all over her body, and he was going to make it very hard on her. He was very pleased with all that had happened, and now he was going to start to show her the other side of things. He got up and moved and kissed on her body as he dropped down in front of her. He stopped to kiss and feast on her pussy for several minutes, lapping up her lovely honey, getting ready for her real discipline for resisting for so long.

"You taste divine, Lillian, and so tight in every hole!! You are a prize that any Captain would love to have as his Woman, but you are mine.. all MINE!! I will teach you how to please me... in my quarters... and in battle!"

When he got what he wanted from eating her pussy, he then moved to get under and behind her. He picked up the flogger and used it, lashing her just hard enough to begin the discipline. He moved around her, getting all of her torso as well as ass, pussy, and thighs. He watched how she reacted, her sweat making it sting just a bit more and pleasing him very much.
 
The beautiful woman moaned as he licked at her womanhood. That felt so good compared to everything else. She cooed and grunted, making sure that he knew how much she was enjoying the caress of his tongue against her nether regions. She nodded her head as he spoke, wanting more of that attention between her legs. His tongue had nearly coaxed her to another orgasm and she let him know it, too.

“Thank you!” she exclaimed. “That feels so good!”

However that stopped. She gave a whimper at the tension between her legs once more. Surely he was going to do something to relieve it. The captain just couldn’t leave her like this! She whimpered pathetically but that whimper was turned into a shrill cry. He was flogging her! She begged for him to stop, called him master, but still he went on.

The strikes on her pussy and asshole were the worse. The quick hit left a throbbing between her legs, making that tension worse. She bit her lip and sweat rolled down her face and over her red tits. Each hit brought more juice from between her legs though.

“No more!” she demanded! “No!”
 
Jack reached up and gripped Lillian's hair, her words upsetting him. He then looked into her eyes, keeping her arched back as he used the flogger again, getting all of the areas again. After he had really finished, he growled as he let her see the intensity in his own eyes as he started to speak to her.

"You demand nothing, Woman! You are mine, and I decide when I stop anything! Do not think because I want you I will put up with your insolence for too long! now, if you ever want to feel my mouth on your twat again in sooner than a week's worth of punishment, then you apologize like a Good Girl and show me you do not need further punishment!"

He waited, flicking his wrist so that the strands of the flogger spun around and slapped against her clit as he did.
 
Lillian gave out cry after cry. It was amazing that she did not go hoarse from her bitter yelps of pain. Why did he have to hit her womanhood like that?! It was painful. Too painful. Tears streaked down her face. He expected so much of her so early. He had just humiliated her thoroughly and now he was punishing her for something she did not understand.

Finally he said something but it did not make her feel better. The redhead whimpered pathetically and begged with her eyes not to have to say anything. Verbal begging was below her and she had already done so much of it that day.

Though the sharp whip to her already raw clit had quickly changed her mind.

“Please,” she whined. “Please, master don’t do this. I am sorry for being so firm. I’m sorry! I’ll be a good girl.”
 
Jack smiled, released her hair and then caressed her face. She was so very beautiful, even with tears down her face, and he was pleased with how she had learned so readily. He kissed her softly on her lips, cheeks, neck and shoulders, slowly unbinding one of her arms as he started to speak to her in a soothing but authoritative voice. His words and tone also were geared to apply the right amount of Dominance.

"You are in such need of a true education, Lillian, and how could I punish you too much when you need instruction more. You are Blade's Woman now, and I expect so very much of you. Now, I need to have you cleaned even better so that you are cleansed of your illusions of your old life. Your loyalty to your sister is the only just and true thing outside of your life that remains, and we will find her."

He pulled on a cord, and three servant girls came into his quarters. After he had unbound her, he had the girls bathe both of them at the same time, the soft hands of the girls moving all over their bodies. After they were rinsed thoroughly from head to toe after the wash of the same, he then administered to any places on her that needed attention. He then softly moved his hands over her clean body, his smile very focused.

"You have questions, Lillian? You may ask them now, as a captains Woman has to be educated. You will not try and escape, as you have now accepted that only I can help you with all your needs."
 
Lillian let out a cry of relief as her arm was freed. It slumped down. There was not any feeling in it and the red mark around her wrist pulsed. Blood slowly returned to that limb, pinpricks causing her to whimper. How she wanted to rub life back into it and to ask him to do it. But she knew better. This was likely part of the punishment. Instead she listened and let out a grateful sigh as her other arm was released.

He was going to train her and that likely meant more punishment. A frown pressed on the corners of her full lips. At least he was not going to be that rough on her to begin with. The washing felt wonderful on her sore and whipped skin. The woman’s hands were delicate with the raw flesh and the beautiful redhead found that she was melting with each touch and scrub. Already she was becoming sensitive to pleasure.

Questions. What questions could she possibly ask of this Captain? She bit her lip and thought.

“Have you really officially married us?” she asked in disbelief. It came spilling out of her mouth before she could stop herself. “Since you have taken me and your marks will be left all over my body, I highly doubt I will be able to find a man to take care of me. I do not want to be dumped off at a random port after Emma is saved.”
 
To Jack, it was an honest pair of questions, and he had no problem with answering both with total honesty. He moved his hands in soft caresses over her body as he answered her, his eyes never leaving hers as he was doing so to make a point. His tone and words were all affirmative and authoritative, something he never wanted her to ever forget about his position on his airship.

"Yes, Lillian, I have officially married us, as the exact words do not matter. Your surrender to me both physically and emotionally is the same as an 'I do', and my accepting your submitting to my being your Master the same. We are now husband and wife, and you will not be dumped anywhere as you are my Woman. Now, you will go over to that bed and get under the silk sheets. We have more of our honeymoon to relish together, and plans to make to retrieve your sister from the slavers."
 
The redhead felt relieved. At least she would not have to deal with the shame of being a single woman tainted. Suddenly she felt very grateful towards this pirate. Her husband. Not only had he protected her but he promised to save her sister as well. This was not all as bad as she had made it out to be. At least, not right now. Now he was being kind and gentle. Her poor clit still throbbed from where he whipped it.

“Yes sir,” she said after he told her to move. She stood. Her legs felt weak and wobbly from being bound for so long. Her arms also felt heavy and sluggish. Lillian crawled into the bed. The silk felt wonderful against her skin and she stretched out, sighing. This type of luxury was very, very welcomed.

It was like as if she could drift off. The woman did not care what he wanted to do at that moment. Her blue eyes closed and began to nod off.
 
Jack was laying beside her, letting Lillian sleep for the time that was needed. He knew exactly how long they would sleep and how he would help her learn to fight. If he knew what he thought he did, only Black Vulcan would have dared to take the daughter of a noble, even a fallen one, as slave. Black Vulcan was the kind of fiend that parents warned their children about in scary stories at night, and Jack wanted nothing more than to terminate him. It was not just about his own objection to slavery, as he simple disapproved of Vulcan's very existence and was eager to end it. He was a vile and heinous creature who did things to women that made his own blood cold at the thought. What made him worried more was that Emma was not just a slave, she had to be a "special order", and that would have been from only a handful of buyers in America. He dozed off, renewed with the desire to train her to fight again, as he wanted to not just equip her to get Emma back, but to help him dispatch not only the man that took her, but who ordered her kidnapping.
 
Lillian’s sleep was troubled at best. So much had happened, it was difficult for her to wrap her mind around, and that had reflected in her dreams. In her dreams, Emma was tied to a chair. Her face was bloodied, her bodice was torn open, and men where taking turns using her body. Lillian was there but she was being held back by the faceless man who had ordered that their father’s debt be taken out on his children. He laughed wickedly, holding the redhead’s arms behind her back and making her watch.

The stowaway awoke in a sweat, breathing harshly. Tears were flowing down her face. It had felt so real! She wrapped her arms around her naked body and began to rock slowly back and forth. She did not want to wake up her master quite yet. Her body was sore from all of the harsh love he had given it and she really was not up for round two. Her tight little asshole stung as she moved. This man, her husband, had done quite the number on her.

As she thought about it, a wet little spot appeared between her legs. The beautiful ginger let out a small cry of annoyance. That was not how her body should have reacted to the pain. Ugh. What was he turning her in to? She looked at him, a strange expression on her face.

Hopefully when he got up, he would simply teach her how to fight.

However, he body was controlling her and soon she was straddling him, pressing her lips to the alcove of his neck, biting and sucking on his skin.
 
Jack slowly awoke as Lillian was doing what she was to stimulate him, a smile slowly coming to his face. This was very predictable, as Lillian was one of those women who loved to hide behind Prim and Proper facades in order to avoid the wants and desires they really had. He was very amused at her suddenly having her body's needs take over, something that was only slightly unexpected as he did not predict her wanting to wake him in precisely the manner he did. The base wantonness was the predictable factor, and he moved his hands down to her hips and got her right where he wanted to be.

"Now let us start the morning the right way...."

With one thrust, he invaded her pussy again and was to the hilt inside of her. He rolled his hips and made his pelvis grind into her more, relishing the entire way that her pussy felt so tightly around his cock at that precise moment.
 
Lillian gasped as he shoved himself roughly inside of her. She wasn’t expecting to be so mercilessly stuffed. The soreness between her legs had not completely petered away. That did not matter though. With the first few strokes inside of her, the stowaway moaned softly. She did not miss a beat and began to bounce slowly on his cock, riding him like a sex starved slut. Her body was not experienced at this but she knew what felt good to her.

“So good,” she managed to breath. Her breasts bounced. They were sore and heavier than normal. More milk had built up during the night. Relief. She needed to have them sucked upon. She leaned forward, pressing her swollen tits in his face.

“Please,” she begged. “They hurt so bad.”
 
As Lillian begged, Jack raised his hands up to her lovely tits, and he started to squeeze and kneed them with his fingers. He was not yet ready to give her what she wanted as far as her breasts were concerned, as she had not done her begging properly. He pressed his fingers just enough, his thumbs preventing milk from coming out as he looked into her eyes with a Dominant gaze.

"Now now, Lillian. By now you know that is not the proper way for a Captain's Woman to beg, and I will not be allowing you any release or relief until you do so properly."

He halted what was going on, keeping her in a position so that she was unable to do anything more until she begged to his satisfaction. She had to know by now that calling him Master or even Captain would be good, but he really wanted her to say the one thing she would have the most trouble saying.
 
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