Denise

*** Chapter 17, Penetration

It was Miss Clearmont who tended to Jake. He did not see her but accepted the baby food with grateful thanks. After feeding him she placed a gag in his mouth that passed between the teeth with a hollow tube to hold his mouth open and than put the tube back in his mouth. She used a cloth, slick with baby oil to rub him down and then placed the dildo in his asshole. This time she use a slightly thicker one with the idea of widening him and preparing him for what was to come in the next few days. Already he was sleeping again soundly.

The sleeping pill in the food had taken effect.

Upstairs Gudrun was sleeping. In just four hours another day of excitement for Jake would begin and the conditioning would begin to work. With a last look to check that all was in order for the next phase she locked the door and went for a walk.

The whip woke Jake again with a light touch.

As he came to he tried to work out how long he had been in this terrible position. Finally he came to an answer, five days or maybe six. Already he was losing track of time as the irregular sleep periods and painful experiences distorted his mental clock.

"Good Morning,” said Gudrun in a cheerful voice confirming his mental calculation.

"Good morning Mistress,” he replied. His dry mouth and the gag made it difficult to sleep. Furthermore he had drunk from the tube and the salty taste did not improve matters.

With a strain he tried to look around but his neck cramped when he did so. Gudrun seemed to be alone. She was fully naked except for a pair of stilettos. Her smooth skin was broken only by a tattoo of a Chinese symbol on her right breast. He could see that she was seeking something in a flat box and wondered what she had in store.

"I cannot move for cramp Mistress,” he croaked as she stood.

"Ach,” she replied in her German accent. "I shall have to move you to another position then."

For a moment he felt grateful that she cared for him and then he thought that it was all her fault anyway. But the emotion did not immediately die, it just faded away.

"I am glad to tell you that release is not far away,” she said as she came to stand just out of sight.

An enormous feeling of liberation filled him as he imagined being set free. His burst of optimism faded as Steve stepped into view, his erection bobbing with the movement.

"Steve has been here two days now without release,” said Gudrun. "He has been such a good boy that I had to let him be the first to try your mouth."

Steve gripped his prick and started to guide it into the open hole in the mask when Gudrun placed a hand on his thigh to stop him.

"Sex with no foreplay?" she asked. "That cannot be. Tongue out for Steve little man."

Slowly Jake extended his tongue to touch the throbbing organ. A small drop of fluid on the end touched his tongue as he made contact.

"Lick properly." Gudrun's order was definite.

Jake licked with a will making the prick jerk with expectation. After a minute or so Gudrun took her hand from Steve's thigh and he pushed into the readymade hole.

Jake felt his mouth fill with the giant cock. Even with his mouth wide open it barely made it through the short tube to touch the back of his throat and tongue. He wanted to retch but the prick drew back and thrust again.

"Is the slut hole trying to please you?" asked Gudrun of Steve.

"No mistress."

Jake moved his tongue to press the warm flesh and massaged the cock with a will. It moved in and out with strong strokes several times before there was a sharp slap. Gudrun had caned Steve's butt. It made him come with a rush Just as he was on the outstroke. Jake felt the come fill his mouth and run down his throat.

"Lick him dry." ordered Gudrun.

Jake lapped at the prick getting the last drops until Gudrun pushed Steve to one side. Jake saw her pussy at close quarters. It was wet with her juices, almost dripping with desire. Her fingers parted the lips and rubbed the soft flesh as Jake watched.

When Gudrun came it was with a loud exclamation of pleasure.

"You have started to please me,” said Gudrun to Jake.

She patted his head with her hand and then collected the last few drops of Steve's ejaculation with her finger. She offered it. Jake licked.

"Thank you Miss,” he said.

Did he mean it?

Unsure of himself he started to sob.

"Very good my little man,” she praised him. "Now that you are learning to please me and serve my needs I may get you moved to a better position."

Jake sobbed. Was it relief or shame? He did not know. What he did know was that he was dependent on Gudrun's will. Her praise was what he sought.

Gudrun's finger was still in her dripping pussy as she gave Steve another order. "Make him come for me."

A hand gripped Jake's prick. Savagely it rubbed him to an orgasm. There was non of the gentleness of Gudrun. The shafting was efficient and thorough. He came and arched in his bonds as the hand withdrew.

"Again." Ordered Gudrun. "I want him to come four more times for me."

One by one the orgasms were wrenched out of his prick. Each more a struggle than the one before. As Jake gave up his come Gudrun once again teased her pussy. A finger slid in and out of the fleshy slit, slick with the juice of her pleasure.

The last orgasm was, for Jake the most difficult. Once again he was sore and excited. The muscles of his thighs bunched with the cramp but at last he found release.

Just as Gudrun had promised.

"Thank you little man. That was so good.”

Gudrun pressed her slick finger in Jake's mouth. For the first time he tasted her juices. He felt relieved that he had withstood the test. Her will was becoming his desire.

***

Miss Clearmont and Gudrun discussed their strategy. They lay in the four poster bed in post coital dreaminess. The sheets lay crumpled and damp beneath their bodies as the two women discussed Jake in terms of depth of submission.

Idly fingering Miss Clearmont's nipple Gudrun spoke first. "Here we are now just two days later, and he is breaking."

"Yes,” said Miss Clearmont as she stared at the ceiling. "We now need a catalyst. To get things moving."

"Fear and hope,” suggested Gudrun. "Fear of you and hope that I will let him go."

"That's right. Good cop, bad cop. I love being the bad one."

"OK,” said Gudrun then I'll be ‘auntie’."

Miss Clearmont rolled onto her stomach and opened her legs. She smiled coyly and ran a hand over her partner's behind. "Auntie, would you please make me come again."

Gudrun could not help but laugh. "Little girls like their Auntie too?"

She slipped her hand between Miss Clearmont's powerful thighs and stroked her ripe pussy.

"Little rich girls need the loving hand of their favourite niece."

Gudrun opened Miss Clearmont's legs a little wider and tickled her clitoris with a long nail. "I think I almost love you,” she said as Miss Clearmont lifted her ass.

She could feel the slick pussy dripping with excitement and massaged slowly.

"I love your touch Gudrun. You are so good to me," purred Miss Clearmont as the fingers penetrated her depths.

"I love your honesty to me."

Gudrun knew that Miss Clearmont would probably never say 'I love you' to her but she also knew that this was as close as it could get. Two dear friends in bed. Equals in their field of pain and pleasure but gentle as two mice when in each other’s company.

Miss Clearmont purred like a cat and felt such deep release that she knew that she could never find another for whom she felt such a close bond.

***

Gudrun looked at the unfortunate figure of Jake.

Just six hours before it had been Miss Clearmont's turn to attend to him. As promised Miss Clearmont had moved him. No longer was he hung by his arms and legs with the sling. Miss Clearmont had put him in a worse position.

Upside down with legs spread wide he hung from his ankles with his head almost touching the floor. His hands were bound to two staples on the base of the wall allowing him to rest some of his weight.

"He is in fear of me." Miss Clearmont had said with a grin when she had attended to him.

Gudrun could see why. Miss Clearmont had obviously caned him thoroughly and then stuffed a huge stopper in his ass. His prick was constricted in a leather tube with studs on the inside and his balls were tightly bound with a wide strap.

"Oh dear me,” said Gudrun as she woke the captured millionaire with a slap. "Had my friend been harsh with you? She is a little severe sometimes."

Gudrun could not help grinning as she ran her hands over the tight skin of his balls noting that Miss Clearmont had shaved him and placed a gold stud in the tip of his cock.

Jake sobbed with relief as he noted that it was Gudrun and not his unknown tormentor who stood before him. The hour of suffering with Miss Clearmont had left him in tears of anguish. She had caned him for not calling her 'Mistress' and then fed him a slush of bitter food.

The enormous object in his rectum had stretched him to bursting as she caned his prick and then bound it. Finally she had placed the tube on him and then given him a painful erection as the studs bit his hardened but tender flesh.

"Please Miss. Do not let your friend have me again,” he begged as Gudrun let him down.

"I'm sorry but she is my friend,” said Gudrun as Jake lay on the floor, his thighs trembling with the strain. "I sometimes let her have my slaves. I know that she is a little harsh but she means well. She just wants to train you, that's all. She just likes to amuse herself a little, that’s what you are there for, after all."

Jake felt relief at Gudrun's sympathy.

She was good to him.

She would protect him.

"Would you like to please me?" said Gudrun with a smile as she allowed him to see by removing the eye patches.

"Yes Miss," replied Jake.

"I am too soft on you,” said Gudrun as she stroked his chest with her long nailed hands. "But, I cannot resist feeling just a little sorry for you."

His legs were still up the wall but now he lay with his back on the floor. Gudrun kneeled over his head and slowly lowered herself until her naked sex was over his face. In the semi-darkness under her skirt he could just make out the lips of her pussy. Slowly he became erect. The sleeve over his prick tightened as he became larger making the studs bite into the flesh. Jake felt a finger stroke the tight exposed tip of his cock and then the sleeve was taken off.

"If you do well I will help you to come,” said Gudrun in a husky voice without telling him what to do.

The naked slave raised his head and licked the warm soft flesh of her mound. "That's right little man,” she purred. "Serve me well."

With a strain he raised his head more and entered her with his tongue. He could smell the gentle perfume of her as his tongue probed as deep as the mask allowed. Gudrun stroked his erection with a soft motion making his prick jerk with anticipation.

"That's good,” he heard her murmur. "Further back..."

The tongue worked its way over the delicate flesh between ass and pussy as he made his way to the puckered flesh of her other orifice. As he contacted the sensitive flesh he felt her shudder to orgasm.

Gudrun worked at Jake slowly building him up. She could sense his imminent peak and stopped suddenly.

"I have to tell you something."

Jake plunged from his state of bliss to earth abruptly and awaited a further bombshell. His worst case scenario was becoming a reality.

"I owe my friend a favour,” she said in a matter of fact voice. "She would like to have you forever." Gudrun sensed his panic and heaped a further worry upon the unwanted revelation.

"She needs only castrated slaves,” said Gudrun in an apologetic tone.

"Please no, Mistress,” he said in a shaking voice. "Do not give me to her. Please!"

"I am so sorry my little man," answered Gudrun. "But I have no option but to have it done and pass you on. Do not worry about me! I shall find another man and get over it."

"Please Miss. I have not told you but I can buy my freedom. I am a rich man. I'll pay you to find another slave and gain my freedom."

Gudrun smiled and shuffled back to look into Jake's begging eyes. With a gentle touch she stroked his lips through the rigid hole in the mask.

"I have as much money as I need. I am sure that you have a lot of money but I really must give you away. More than money is at stake. I gave her my word and that is something that I cannot break,” she said trying to look as though she was apologetic.

"Really Miss, I can make you rich as Croesus,” he begged.

"No more of this," ordered Gudrun as though offended. "I do not wish to hear any more. You will be given to her in a few days after the operation and that is that."

Jake made to speak but Gudrun interrupted. "I said that was my final word. Do not spoil our little friendship with lies."

She fetched a gag and screwed it into Jake's mouth with a savage twist. "I will ask her to be nice to you but you will be her slave whatever you personally wish for." In a wistful tone she continued. "You just have to accept the decisions of your betters my little man."

At that moment Jake heard the door open. He made to look round but already Gudrun was fixing the eye patches to his mask blocking out the room.

Gudrun strolled to the door and went into the corridor. There stood Miss Clearmont with her finger on the button of a tape recorder. In her other hand she held a script.

Joan Lorde's voice came from the loudspeaker. The sound was a little indistinct from inside the room but Jake heard every word. "I have all the money, my stupid husband has not got a red cent left. We will share as agreed."

Miss Clearmont held the script for Gudrun to read.

"I know that we have it all. The operation is the day after tomorrow and then he is gone forever. My dear friend will make sure that he does not last long, she likes her pleasures somewhat extreme."

Miss Clearmont smiled and read from her part of the script. "I promise you Joan. He will last no more than a month. Under my whip he will experience a lingering but exciting few days. Gudrun owes me!"

Miss Clearmont closed the door with a rattle of the locks and bolts and then burst into laughter. "That was fun,” she said. "Amateur dramatics were always my forte."

"You should be writing screen plays for a living,” said Gudrun as she pecked her lover on the cheek. "Now he believes that he's really for it."

In the cell Jake lay with his mind churning.

His wife was behind all this.

He had fallen into a trap but Joan had not realised that he had hidden money to buy his freedom with. Somehow he had to buy his way out and now he had but a couple of days to do it. 'Gudrun is my last hope,’ he thought in a whirl. 'I must get her to listen, but how can I prove the truth to her?'