Devils Island

18. The Yacht

After having disposed of Jason's body, Jack resumed his solo sailing adventure toward the coast. Tess was securely locked in her cell below deck and would not cause him any problems. Jack was proud of himself, Jason had never suspected that he would betray him if the opportunity presented itself. Jack had been the one that had kept a close eye on the slaving operation and unknown to Jason reported every move made to the Master. He had in fact worked for the Master long before he met Jason. Master was also responsible for Jack being released from prison early, even though Jack had been convicted on a totally unrelated charge. Jack set the course for the coastline and switched on the autopilot. He had at least 18 hours before he would reach the mainland, maybe longer if the weather didn't hold. It was time for some rest and recreation and to put the “crew” below to work. Jack's bonus for long and loyal service was Tess. He could keep her on the yacht until the end of the week before he had to deliver her to Sanchez at the whorehouse. Jack would also get a percentage of the money Tess would bring in as a whore. After Sanchez and the Master had taken their cuts, Jack calculated he would still receive anywhere from 300 to 500 dollars a week. If Tess lasted 2 years at the whorehouse, Jack would make somewhere in the neighborhood of 50,000. Far less than the Master or Sanchez but for doing nothing, it was good money. Jack would still make the pick up runs of new girls for the island but he would not be involved in the abductions anymore. He would just pick up the cargo and deliver it to the island. He could handle that without hiring any additional crew and therefore he would not have to split the profit with anybody else. Jack reached the cell that housed Tess. He stood there for a moment just looking at her while he was trying to decide what kind of recreation he was in the mood for.

“Where are to taking me? What is going to happen to me?” Tess asked somewhat subdued and fearful.

“Do you really want to know?”

“Yes. Please just let me go. I won't say anything to anybody.”

“I have heard that one before. I'm not that stupid.” Jack replied.

“You will do what I tell you to do and go where I tell you to.” He continued.

“Please. I will make it worth your while, if you just let me go.”

“When did you become rich? You are nothing more than a run away that nobody will miss.” Jack laughed.

“Maybe I could make it up to you in another way?” Tess tried.

“What way would that be?”

“Hmmm. I could help out on the boat, cook maybe?”

“I don't need a cook. You'll have to come up with something better than that.” Jack answered.

Tess got the distinct feeling there would be only one offer that would even be considered by Jack. She really didn't want to offer any sexual favors but she remembered the treatment the girl called Penny had received onboard so maybe that was the answer, if she willingly offered to fuck these men. Tess didn't know that Jack was the only one left onboard now.

“I'll let you fuck me.” She said reluctantly.

Jack burst out laughing. He shook his head in amusement.

“You are not a very bright whore. I can fuck you as much as I like and as often as I like and there isn't anything you can do to stop me.”

“Look around you. You are in a cell onboard a boat in the middle of the ocean. What would stop me from fucking you?”

“Nothing I guess.” Tess replied in a defeated tone of voice.

“Your right about that.”

“So what do you want in return for letting me go?”

“Nothing. I do not intend to let you go.” Jack said with a laugh.

“Well. That's not quite true. I will hand you over to the whorehouse owner eventually.” Jack corrected himself.

“Please no. I am not a whore.” Tess was frightened.

“You are right. You are only a wannabee whore at the moment but after I get done with you, you will be a whore trainee, even if you won't be a full fledged whore by the time we reach the mainland.”

“At least you will have completed your basic training.”

“Please you can't do this to me.” Tess was sounding desperate now.

“Sure I can. You mean nothing to me. You are just a piece of meat for my enjoyment and profit.”

“Enough of this chit chat. I am in the mood to play.” Jack said.

Jack unlocked the cell door and entered the cell. Tess in a desperate attempt to escape swung her clenched fist against Jack's jaw. Jack ducked and took a step to the side. Before Tess could swing again, Jack landed a powerful punch right in her stomach, knocking the air out of Tess. She dropped to her knees gasping for air.

Jack kicked her right between her legs just to cause her more pain and make sure she got the message that such behavior would not be tolerated. Jack bent down, grabbed her by her hair, and pulled her along toward a contraption in the center of the cell deck area.

“Ouch, that hurts. Let go of my hair.” Tess cried out.

“Don't be such a baby. Whores need to learn to enjoy some pain and rough treatment.”

Jack stopped in front of the device he intended to secure Tess to. She struggled to her feet with Jack firmly holding on to her hair. Tess couldn't figure out what she was looking at or what Jack had in mind. Jack pushed her forward until her thighs pressed against the closest T-bar. With his free hand, he reached in between her legs and pulled the first strap around her right thigh. The strap was secured to the bar, and with the help off a knob on the bar, it was pulled very tight. He repeated the procedure with the second strap around her left thigh. Tess felt the straps biting into her thighs and tried to reach the knobs with her hands to get free. Jack let go of her hair and grabbed her right arm, pulling it forward. Her wrist was secured to the front T-bar with a steel cuff that was welded on top of the bar. Tess did manage to loosen the left thigh strap somewhat before Jack grabbed her left arm and locked that in place. Jack tightened the thigh strap again. Tess was now firmly attached to the double T-bar device. With her arms straight out in front of her and her thighs pressing against the bar, she was forced to bend forward in a horizontal position. Jack pressed a pedal on the floor and the two T-bars began moving further apart stretching Tess between them. When Tess shoulders were about to pop, Jack stopped the machinery.

“I won't pull your shoulders out of their sockets unless you misbehave.” Jack warned her.

“Ahhhh. It hurts.”

“Just wait. You are not done yet. There are a few other and more interesting features to the whore trainer.”

“Please. No.”

Jack stepped back to admire the view of the still dressed but stretched out Tess. Jack smiled he was pleased with his handy work. He scratched his chin while he contemplated what additions he should make, so that Tess would be even more “comfortable”. He disappeared for a few moment and Tess could hear him shuffling a few things around. When he returned he was carrying what looked to Tess as two wheels with a number of straps attached. The straps where fairly wide but not very long, still they were long enough to reach the base of her tits. Jack bent down and placed the wheels right under her breasts.

“ This is a fun addition. Once I get them in place and the wheels start turning, the straps with fly around and beat your tits at a steady pace. The wheels will turn in different direction to spread the blows evenly on you tits.” Jack explained.

“Please don't hurt me like that. I will let you fuck me any way you want.” Tess begged.

Jack laughed.

“You silly whore. I can do whatever I want to you at any time. I would have thought you had gotten the picture by now. You are not very bright are you?”

 

Jack bent down and reached under Tess. With one powerful pull, he ripped her top off. He unhooked her bra and pushed it down along her arms, Tess tits hung straight down. Not satisfied with that, he added a clamp with a heavy weight attached to each nipple, effectively stretching her nipples and breasts toward the deck. Tess groaned as the clamps bit into her nipples and stretched her breasts.

“That is better. Now your tits will get a nice and firm beating when I start the wheels, without bouncing around too much.”

“Please No.”

Jack adjusted the speed on the wheels and then with a smile flicked the switch to set the wheels in motion. Tess reaction was immediate as the first strap flew around and hit the outside of her right tit. This was quickly followed by another strap from the second wheel landing on the outside of her left tit. The pace of the wheels was steady as alternate blows landed on her weighted down tits.

“Aaaaaarrrrrrrrrggggghh” Tess let out a series of groans and screams.

“I just love the way your whore tits move around. Once we really get into it, I will increase the speed and that will make the blows harder.” Jack snickered.

Jack moved behind Tess and pushed her skirt up around her waist. Slowly he pulled down her panties until her openings were exposed and available. Tess felt something thick and sticky being poured on her ass checks. Jack proceeded to rub in the sticky mess all over her cheeks. Massaging and squeezing her buttocks, he worked the paste into her skin. It didn't take long before Tess felt the warm almost burning heat.

“You are almost ready for a nice pleasant fuck. Only one thing remains to make it perfect.” Jack casually informed her.

As soon as he had finished those words, he swung the cane with moderate force, landing the first blow right across her already heated ass. This caused Tess to let out a new series of high-pitched screams. Jack continued to swing the cane with the same tempo as the straps were biting into her breasts. Tess was truly miserable. Her ass was now full of angry red stripes and burning. When she heard the cane drop to the floor, she couldn't help but draw a sigh of relief.

“Now you look like a whore should, to give maximum pleasure to a paying customer. Very sexy looking.” Jack chuckled.

“Let us hope your performance lives up expectations otherwise I will have to use something more serious than just the cane.”

Jack moved to the front of Tess and without a word pushed his limp cock against her lips. Tess not wanting any additional treatments obediently opened her mouth and began to lick and suck his cock. Jack allowed Tess to suck at her own pace until he had gotten hard and erect.

“Let test how deep this front hole of yours is” Jack said as he pushed his cock deep into her throat.

Tess gagged and was grasping for air. Taking no notice, Jack continued to ram his cock in and out of her mouth and throat. When he finally withdrew, Tess drew a deep breath, coughing, spitting, and drooling and her throat felt sore from the rough pounding.

“Not too bad but you need to practice more to perfect your skills. Lets see how your back end holes work.”

Jack moved behind her and grabbed her burning buttocks. Spreading her pussy lips with his thumbs, he plunged his cock deep inside her dry pussy. Tess let out a long groan as soon as the intruder filled her pussy.

“I need to teach you to get wet and stay ready. Your hole is too dry, customers don't like that.” Jack said.

Tess wasn't paying any attention to what Jack was saying. She was only concentrating on the pain she was feeling. Jack enjoyed not only the pain he was causing Tess but the fact that Tess was so dry that her pussy gripped his cock tightly. He was not done torturing the poor girl. To increase his own enjoyment, he turned up the speed to medium of the two wheels. This caused the straps to hit her tits harder and more often. Tess moaned and groaned even louder when the wheels increased their torment. Jack continued to fuck her at a steady pace, pushing his cock as hard as he possible could, bruising her cervix as his cock hit the inner depths of her pussy. When he felt himself close to injecting his load into Tess, he quickly pulled out and waited for the urge to subside. Tess let out another loud scream when she felt his fingers probing her ass hole.

“No. Not there. You are too big.” Tess screamed.

“Nonsense. Just relax and enjoy the ride. You need to be stretched back there as well.”

“Please. No”

Tess's pleadings went unanswered. Jack used his hands to spread her back door and pushed home as deep as he could. It took him several hard thrusts before he had buried himself deep in her ass. What followed was a rough and hard ass fucking with the additional pain of the wheels turned up to high speed. Her tits were now being beaten hard and fast by the straps of the wheels. Jack enjoyed this and it didn't take him long to fill her ass with his semen. Tess screamed and hollered until he pulled out of her ass and finally turned off the horrible wheels.

“You definitely need more practice whore. This was no more than an average performance. The customers at Sanchez place will expect a lot better fuckings than this. First lets work on your sucking skills while I take a break for dinner.” Jack calmly told her.

Tess only heard the first part of Jack's words. She was in too much pain to really care about what he was saying. She was sore all over and her tits felt like they had been put through a meat grinder. When Jack returned and placed a long metal pole in front of her, she began to cry. The pole had a 6-inch dildo pointing straight at her mouth. At the bottom of the pole were a black box and a plastic container.

“This is another good part of the whore training device that you are attached too. I will fill the container with doggie semen. The dildo is lined with sensors and when you please the dildo with your mouth, it will inject a load of semen in your mouth. If the dildo isn't pleased then you get no reward. The plastic container holds a gallon of semen. I will hook this pole to the wheels and if you take too long to please the dildo the wheels will start. They will be set to maximum power none of the soft start this time. When the dildo spurts in your mouth, the wheels will stop until you fail to please the dildo in time again. When the semen container is empty the bars you are attached to will contract slightly and relive the strain on your shoulders and body.”

Jack explained.

“Please I am hurting. I can't take any more.”

“Sure you can. A good whore needs a lot of stamina. I will put a bowl under your mouth and anything you don't swallow will be put back into the container. When you are done sucking your training lover dry, I will let you pee. Until then, you have to hold it unless you want another 20 strokes of the cane. If you prefer I can put catheter in your pee hole. Would you like that?” Jack asked.

Tess didn't answer. Therefore, Jack repeated his question. Tess just shook her head and Jack smiled. It would take Tess several hours to empty the container and it was unlikely she would be able to hold her bladder that long.

“As you wish.”

Jack connected the pole to the wheel and moved the pole so that Tess could get the entire length of the dildo in her mouth. When he was satisfied, everything was in place and secure, he flipped the switch to the sensors. Tess gingerly started to suck on the dildo, expecting something nasty to happen. To her surprise nothing happened, she only got a slight bitter taste in her mouth.

“I will check back and see how you are doing after dinner, whore.”

 

Jack left and Tess was left with her new lover and with her body aching and burning. Tess was in hell or at least that is how she felt. She had a hard time concentrating on the task in her mouth and after about ten minutes, the wheels started their pounding of her tits again. Tess tried to concentrate and sucked away as fast as she could. Eventually her hard work was rewarded and she got a big load in her mouth. She gagged but tried to swallow as best she could. The wheels stopped and Tess continued to slave away with her mouth.

Jack left his trainee for about 3 hours before he returned to check on her progress. Tess was still slaving away and she had managed to empty ¾ of the container even if she had spilled some in the bowl. Jack took the bowl and emptied the content back into the container. Jack feeling raunchy again moved to the back of Tess and produced a catheter with a long plastic tube. The tube was clamped before he painfully inserted the catheter into her pee hole. Tess was too tired to do anything but groan loudly. Jack proceeded to attach the end of the catheter tube to the container holding the semen. Tess was horrified. With no control of her bladder, she would keep filling the container. Tess realized she would have to suck forever unless she some how could stop herself from peeing. Jack grinned, and released the clamp and pushed his now hard cock into Tess's pussy. Tess couldn't stop the pee and a yellow stream mixed in with the remaining semen in the container. Jack gave Tess another hard fucking but instead of shooting his load in her pussy, he pulled out and added his semen to the container. Tess was frantic.

“Still to dry in your hole. Maybe you are not trying hard enough or are you not enjoying your whore-training machine? Maybe you will like the one Sanchez have better. His has a double pole in the back, which I don't use. Sanchez doesn't believe in training one opening at the time. He likes to get a whore trained and trained quickly. I am tired, so I am going to bed rather than wait for you to finish the container. I will leave you here tonight and when you are done you can sleep on the whore trainer.” Jack concluded.

“Have a good night whore.”

Jack left and turned out the light. Tess was left in the dark with her task. She could no longer see how much fluid was left in the container. She only knew that her only chance of any relief or even sleep was to finish the task and try not to pee. When her lover rewarded her with his next load Tess could not hold down the pee and semen mix and she retched. It would be a long and strenuous night.