Chapter 19: The Whorehouse

Morning came and the people and animals on the island started their day. A new day also started for poor Tess on the yacht. She had gotten very little sleep and her body ached. Her mouth was dry and her stomach grumbling. She was both mentally and physically exhausted. The last bit of fight and hope had left her sometime during the night, she had resigned herself to a fate worse than hell. When Jack arrived carrying a tray with breakfast, Tess thought her torment was over for the time being. Jack pulled up a small table and put the tray on it. The sight and smell of bacon, eggs, toast, coffee, and juice made her mouth water. Jack pulled up a chair and sat down at the table.

“I thought I would enjoy a little company while I have my breakfast. I see you sucked your new lover to completion. Did it take you long last night?” Jack asked.

“Yes. It was so hard; my jaws are stiff now.”

“Don’t worry. With some work after breakfast they will get back into working condition.”

“Please I am hungry and thirsty.” Tess pleaded.

“You can’t be hungry after having that giant meal throughout the night.”

“Please.”

“If I give you some breakfast. What do I get in return?”

“Anything you want.” Tess hoped Jack wasn’t just teasing her with the food.

“I will give you one chance to prove what a good whore you will be and how willing and obedient you are. If you fail, you’ll go hungry until you learn.”

“Yes Sir. I promise I will be good.” Tess answered.

Tess was at the point she would agree to anything just to get out of the situation she was in and to get something to eat and drink. Jack released her wrists and thighs. Tess straightened out her body with great difficulty. She removed the weighted clamps from her nipples and felt the blood rush back into them as they came alive again. She waited for Jack’s next instruction.

“Get a stool and sit to the left of me by the table. Pull your panties all the way down before you sit.”

“Yes Sir.”

Tess found a stool and pulled down her panties. Sitting down was not pleasant with her ass still sore from the cane. She looked at her breasts, which were very red and swollen from the straps. The feeling had returned in her nipples and they were painful to the touch. She waited patiently next to Jack.

“Spread your legs and show your pussy. Rub your clit until you are wet. You get nothing until you can show me some wet fingers from your hole.” Jack said.

Tess driven by hunger and the smell of the bacon began rubbing her clit with vigor. It didn’t take her long before she was wet enough to show Jack what he wanted.

Jack scoped up some food and dumped the plate in her lap. He reached down and removed the catheter. Tess ate eagerly and more than anything, she gulped down her juice and coffee. Jack smiled, Tess would no longer struggle or resist. She still had no idea that, what she had experienced so far, was nothing in comparison to what awaited her at the whorehouse.

“Let’s see if you have learned anything or if I need to give you another session on the whore trainer.” Jack grinned.

“No please. Don’t put me back there. I will be good.”

“Stand up. Bend over. Get my cock out and suck it hard.”

Tess did exactly what she had been told. She didn’t want to be strapped to that horrible contraption again. Her jaw still sore from sucking the dildo for hours, she bent over and gingerly took his cock in her mouth. Even bending over was strenuous, her muscles aching.

“Keep yourself wet and make sure I have a good view of you rubbing your clit. The customers want a good show as well as an excellent fuck.”

Tess pulled her skirt up and began to rub her clit. She knew that if she didn’t stay wet, Jack would probably put her back on the contraption again. Jack was getting rock hard and erect from her efforts.

“Now get your pussy on that cock and get to work.” Jack commanded.

“Ok.”

“No. You stupid whore, you have to be more pleasing than that.”

“Oh Yes fuck me honey.” Tess tried.

“That’s better but you have to sound like you mean it.”

“Yes, honey I would love for you to fuck my wet pussy.” Tess said in her sexiest voice.

“That is more like it now get to work and wiggle your tits when you say that next time.”

Tess straddled Jack and began to lower herself on to his cock.

“No. No. You always face the customer when you are on top, so he can squeeze your tits and suck your nipples.”

Tess turned around and Jack grabbed her sore tits pulling her down on his cock. He continued to squeeze and pinch her while she moved up and down as fast as she could on the cock. It didn’t take him long before his semen shot up deep in her pussy. Tess sat still not sure if she should get off or stay where she was.

“As soon as a customer unloads, you get off him and get his cock put away. You need to get him out of your room, so you can get the next one in. The more customers you take care of the more money we make off you and then Sanchez won’t have to beat you. Got the picture?”

“Yes. I get the picture.” Tess answered a little subdued.

“Good. Get yourself cleaned up, shower, change into the new outfit, and put fresh make up on. You have an hour before I come back. When I do, I want you to be ready and, in your cell, waiting. If you are not, then back on the whore trainer you go for another long session.”

“I don’t want to be a whore. Please let me stay with you.” Tess pleaded.

“Just do what I tell you. No more nonsense.”

“Please.”

“One more word and you are back on the trainer.”

Tess didn’t dare say anything else and when Jack left, she undressed and went to take a shower. The warm water felt good on her aching body. She stayed in the shower, washing her hair, and cleansing her pussy and ass. She emptied her bladder as well to be on the safe side. She wasn’t sure how long she had been in the shower and she began to worry that time was running out and she wouldn’t be ready. She quickly dried herself and applied her make up. She did her make up very heavy and hoped that it wasn’t too much, but she figured too little would not be accepted. With her make up complete and nails painted bright red, she began to dress. The black half-cup bra felt a little small and her breast were pushed up more than she would have liked. The rest of the outfit was pretty much the same as before. The high-heeled shoes were just as uncomfortable as the last pair she had been wearing. She took one quick look in the makeup mirror and hardly recognized herself. She had been transformed from a run away in jeans and T-shirt to a sleazy looking whore.

She felt the tears welling up and tried her best to hold them back. She couldn’t ruin her make up now. Tess was very unhappy but also scared. This was not what she had in mind when she and Jane ran away from home. She entered her cell and sat down to wait for Jack. She wondered if this was the way people on death row felt.

On deck, Jack swore slightly. The trip had not taken as long as he had thought and when the yacht approached the isolated dock, there were two men and a car waiting. Master had clearly alerted Sanchez and he was on the dock waiting for his new whore. Jack had planned to hold on to Tess overnight and teach her a few more tricks and get a little bit more enjoyment out of her but that would not be happening now. Jack was a little disappointed, but it soon passed when he thought of the money this whore would bring him. Jack docked and waved to Sanchez to come onboard.