Jack and Jill - Part Four


After the evening at the Jaguar dealership, Jill realized her sex life, and more specifically her life with Jack Dillon was not to be a simple one. That evening, upon returning to Jack’s house, a long conversation took place, after Jack had soundly fucked her.
Again, Jack explained that he wanted her to be his complete, bound and naked sex slave. This would mean that he could use her in anyway he saw fit, including giving her to another person for use as a sex slave. She had given up the right to say no. Her only choices were to surrender to him completely, or leave to resume her former life. Jill loved him too much to leave, and secretly she admitted to herself that she loved being totally helpless to Jack, and his demands. Her answer to him, she wanted to be his sex slave, and would surrender to him. "Sir Stephen" had warned her about Jack, and what would be required of her. So she had no complaints. She was willing to see where Jack was going to direct her life.
A couple of days later, Jack had to take a flight to Calgary. He gave her the keys to his new Jaguar, and told her to visit with her mother. Although she talked to her mother regularly on the phone, she had not seen her seen her since she moved in with Jack.
She meet her mother at Durado’s, at Jack’s suggestion. He had an account there, and encouraged Jill to use it.

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   Annie Cates was a beautiful woman. She had given birth to Jill when she was only eighteen. As a result, she was now a beautiful forty-eight years old. Annie was conscious that she was a beautiful woman, and worked hard at taking care of herself. She looked younger than her years, and caused the head of many a man to turn to watch her walk by. She had the same great complexion and hair as did her daughter. Her body, even at 48 years was tight and built along the same lines as Jill. She was blessed with great legs, sweet tight ass, and fantastic breasts. It would be honest to say that Jill was definitely her mother’s daughter. There were times when people mistakenly took them for sisters.
Lunch was intimate, and it was good to see her mother. Annie appeared to be under a great degree of stress, and was somewhat withdrawn. When Jill pressed the issue, Annie broke down and confessed. The new "Dot-com" computer company where she worked was having hard times, like so many in the industry. There had been so much promise when she first joined them.

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   She had invested heavily in their stock. Now the stock was worth only pennies on the dollar, and she was being laid off. She felt that the company would go "Chapter 7" in a short period of time. Annie would soon be out of a job, and all her savings were gone as the result of the decline in the value of the stock she had invested in.
Annie explained that it would be hard for her to get a job because of her age. Even though she looked young and vital, when her birth age was discovered, the companies always hired younger people. To say the least, Annie was very depressed.
After lunch, Jill and Annie went shopping, after which, Jill went home to wait for Jack. She was very concerned about her mother, and how she would make a living. If only her father had not died so many years ago. Annie had been a "stay-at-home" Mom, and a sexually subservient slave wife to her husband. Life had been good, but that was a long time ago. For all practical purposes, Annie was in a desperate situation.
When Jack returned from the Calgary flight, he found Jill at home, naked as usual, wearing only her high heel shoes, as he required. It was obvious that she was upset.

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   When asked what the problem was, Jill broke down and cried, explaining her mother’s predicament. Jack had met Annie several times, and found her to be a beautiful, sexy and fascinating lady. He liked her very much. He listened to Jill for a while, and then told her that he would have to think about it. He said he would talk to her later.
Later that night, after tying Jill to a whipping table, face up, and giving her a rather severe pussy whipping and fucking, Jack was ready to talk about Annie.
"Jill, you are my slave, and have agreed to submit to anything I want to do to you, am I correct", he asked.
"Yes, Jack, I will submit to anything, you know that. I know I am a slave by nature, and I am convinced that I love you. I want to be your slave. What ever you want to do is all right with me. "
"Well, sweet slave Lady, let me present an idea. In normal circumstances, a daughter would invite her mother to stay with her for a while, until the mother gets back on her feet. That creates a problem for us, as I love our life style, and am not willing to compromise. I would not miss one minute of having you as my sex slave, at my beck and call.

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"So", Jack continued, "Here is what I propose. You have told me that your mother was a willing sex slave to your father when he was alive. Annie enjoyed being under the sexual control of a man. After her marriage was over, she never found a man that could treat her like your father did. Am I correct ?"
Well…, yes…yes, you are right", Jill answered.
Jack and Jill were sitting on the couch in the den. Jill had taken Jack’s cock out of his trousers, and was softly stroking it to a rigid erection.
"I propose, my sweet little slave, that I move your mother into my house, into the guest room, and have her live here as my other complete bound naked sex slave!"
Jill, shocked, jerked her hand away from Jack’s cock, and exclaimed, "No! no, I couldn’t do that to her! No, I just couldn’t!"
"First, little slave of mine", Jack sternly warned her, "Don’t you ever remove your hand from my cock unless I tell you to!"
Jill bit her lip, and grasped his cock and continued to stroke it, but she was upset.
"Next, you know I will give you to other people, and at times I will use another person’s slave. There is no reason why Annie, who has loved being a sex slave, could not be a slave again, my slave. She could live here for as long as she wanted. I would pay all her bills, give her a car, and make sure she has a generous allowance, just like you. She would enjoy it, I am sure, and I know I would enjoy having a second slave to torment along with you. "
Jack continued, "It would be a good life for her, as much as it has been a good life for us. "
Jill and Jack talked for the better part of an hour.

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   They finally agreed that Jill would talk to Annie, and present Jack’s offer. Jill was not sure about the proposed situation, but would do as Jack asked. Jack made sure she understood that Annie would give up all rights to her sexual being. As with Jill, Jack would be in total control of her, and he would be obeyed.
After their conversation, Jack and Jill had a rather ordinary vanilla love making session, after which Jill sucked his magnificent cock to a drenching cum. Perhaps this new situation would work out, she thought.
The following day, Jill and Annie met, and Jill presented Jack’s proposal. Annie was taken by surprise. She was not as upset as Jill expected her to be. She did not know what to say, but after talking with Jill for a long while, she decided that it could be interesting. If it did not workout, she could work on another arrangement for her life. Annie knew that she was in serious financial trouble, and needed help. She found Jack to be an exciting man, and had suspected that he was keeping her daughter as a sex slave. Finally, with some misgiving’s Annie accepted Jack’s offer of sexual slavery.
The day Annie moved into Jack’s guestroom, he was at Love Field, accepting delivery of his new Gulfstream G3 corporate jet.

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   This would allow him to take on more cross-Atlantic contracts. He was in a hurry, however, as today was the day that his "harem" would increase in size.
When Jack got home, he found his slave Jill, naked as required, and her mother, Annie, still clothed, having coffee at the kitchen table. Jack greeted the two women with a smile. Jill got up and ran to Jack, hugging him around the neck, pushing her body against his. He hugged and kissed Jill, while squeezing her breasts, and stroking her pussy, while Annie looked on. Just watching Jack and Jill exchange affections caused her pussy to spasm. It had been so many years since she had enjoyed a man treating her like that. She realized that she needed to be a slave to a strong man.
Jack, then turned to Annie, and gave her a light hug and a kiss on the cheek. Annie was disappointed. She expected Jack to take more liberties. Jack was waiting for the right time. While Jill was pouring him a cup of coffee, he and Anne were talking. It did not take long for Jack to get to the point.

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"Annie, what do your think? Can you be my sex slave?" he asked.
Quietly, Annie, with lowered eyes, said, "Jack, I don’t know. As you know I am having problems. I really appreciate your help. I find your situation with Jill to be exciting. I want all the happiness in the world for you two. I would not want to come between you. I know I am a slave at heart, however, and your proposal is very exciting. If you want me to be a sex slave, along with Jill, then I will submit. If it doesn’t work out, then we will have to do something different. "
Jack watched Annie as she talked. Yes, she was one beautifully sexy woman. He would love to put a whip to her tits or ass. He could imagine her pretty face with his cock in her mouth. He also realized, that having beautiful, sexy daughter and mother sex slaves was every man’s fantasy.

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Smiling with approval, Jack was pleased. Jill was on her knees beside him. She was stroking his cock through his trousers. He erection was obvious. He suggested that they adjourn to the den, where things were cozier and more private.
The two women walked ahead of Jack, arm in arm. Jill, naked with just a pair of red high heels, and Annie with her business suit, complimented by a pair of black leather, high heel pumps. From the back they made a beautiful pair. This was the promise of many good things to come.
Once in the den, Jack reclined on the couch. Jill kneeled down in front of Jack, and extracted his cock from his trousers. His cock was already at full erection. She started kissing and licking the sensitive head. Each time she would touch it with her tongue, it would throb.
Jack had instructed Annie to stand in front of him, just a few feet away.

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   His instructions were quick and sure. She was told to remove her clothes, with the exception of her heels. Annie removed her suit coat, and then her blouse. As she removed her bra, Jack told her she was never to wear a bra or panties again, without his permission. As her breasts swung into view, he knew his decision was right. Her breasts were great. They were heavier than Jill’s, but they were firm and stood well out on her chest.
Next came her skirt and panties, along with her garter belt and hose, until she was standing naked, with only her high heeled pumps and her hands resting submissively behind her back. Jack could not believe his good fortune. A mother and daughter, both of whom were beautiful, and submissive. Both of whom were going to be his personal sex slaves. It was almost more than he could contemplate.
"Jill", Jack said, "go to the chest next to the bar and get some ropes. "
Annie swallowed hard, as Jill did as she was told.
"Now, Jill, tie your mother’s hands behind her back, tightly.

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   If you don’t do it right, you will be punished. "
Jill did tie Annie’s hands, tightly. Annie gasped as the ropes bit into her wrists. It had been years since she had been tied. In a very real sense it felt good, and it was exciting. Her pussy was warming to the atmosphere.
Next, at Jack’s instructions, Jill tied Annie’s elbows, until they touched in the small of her back. Annie was a picture of erotic beauty. Her eyes were closed and her breath was coming in short gasps. It had been years since she felt like this. Her raised breasts were rising and falling with her breath. She was slowly shifting back and forth, as if waiting for a cock to enter her cunt.
"Jill, gag Annie with a leather penis gag", he ordered. This was accomplished. Annie was now totally under Jack’s power.


   Everyone in the room, including Jill was excited.
"Annie, welcome to Jack’s Wonderful World of Sexual Slavery. I must compliment you. You are as beautiful as your daughter, which is pretty damned awesome. "
Annie lowered her eyes, and blushed at Jack’s compliments. She felt exposed, vulnerable, and most of all, she was excited. Her body was more alive that it had been in years. Her pussy was hot, and very wet. Her mind was in an erotic haze, waiting for Jack’s next move.
Jack remained sitting on the couch. Jill had returned to him and his cock. She was kneeling between his legs, stroking and gently sucking his rigid member. "Annie, the rules around here are simple. You will surrender completely to me. You have given up the right to say ‘no’.

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   I will use you sexually in any way I see fit. I will restrain you, whip you, torture you, and fuck you to my hearts content, and at my whim. You will be severely punished if you even think the word ‘no’. "
Jack continued, "You will dress exactly the way I tell you, or remained undressed as I may wish. You will never again wear underwear, and you wardrobe will be changed so that all your clothing will be tasteful, but revealing. Jill will take you shopping, and will show you what to buy. From time to time, as I wish, I will give you to others to use as I do. You have no right to say ‘no’. If you choose to say ‘no’, you will be punished, and our relationship will be over. As long as you remain with me, you are mine to do as I wish. "
Annie stood there, her breasts rising and falling with her agitated breath. Her cunt aching for a cock. Her ass needing a whip. She raised her misty eyes to Jack. He was smiling back at her.

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"Do you consent to be my sex slave?" he finally asked.
A tear of happiness and lust formed in the corners of Annie’s eyes as she nodded affirmatively to Jack’s final question. Naked, gagged, with her wrists and arms secured behind her back, she walked towards Jack. Her breasts were held high, and tears running down both cheeks, she accepted her slavery.
Jill helped Jack to undress. When he was nude, Jill was put on her knees, and instructed to suck Jack’s cock. Annie, as ordered approached Jack. He took her in his arms and started to kiss her gagged face, as he squeezed her breasts and teased her nipples. He examined her pussy. She was hot and wet. He continued to examine Annie, as her daughter, Jill was sucking his cock.
Jack, suddenly pulled his cock from Jill’s mouth, and told her to stand. "It is time"’ he said, "to welcome Annie to her new life as a slave. " He then ordered the both of them to his "game" room.
This was a former bedroom, just off the den, which had been turned into his own private dungeon.

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   Inside, one could find any assortment of sexual torture devices, including whips, whipping posts, nipple clamps, restraints, whipping benches, and of course, and king size bed in the corner of the room. Annie was wide eyed with wonder as she visually examined the various devices designed to torment her. Her pussy spasm caused her to shiver with excitement.
Jill was instructed to tie a suspension rope to Annie’s already bound wrists. This rope went to a pulley and wench in the ceiling. Once the rope was firmly attached, Jack flipped a switch on the wall, activating the wench. The rope was pulled upward, pulling up on Annie’s bound wrists and arms, until her wrists were pulled high up in the sir, severely bending Annie at the waist.
Annie was a magnificent sight. Bending her over like this caused her tight ass to stick out. Her tremulous breasts were now hanging, inviting Jack to torment them. Her pussy was visible between her thighs. Her legs were now strained to support her. Jacks cock leaped and throbbed at the sight of her.
Jack had Jill bring him a multi-stranded whip from the wall, along with some spring loaded nipple clamps. Jill was made to massage Annie’s nipples, pulling and teasing them, until they were hard.

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   She then installed the nipple clamps on her mother’s breasts. A third clamp was clipped to Annie’s clitoris.
Annie was in pain. Her trembling breasts and nipples were burning, and clitoris was dancing to it’s own tune. Through all this, she knew the heat in her cunt was rising, and she was very excited.
Jack approached her. Jill was standing next to him. He reached down and fondled Annie’s hanging breasts. These breasts were firm and sensitive. She gasped as he squeezed them, and teased at the nipple clamps. Her breath was heavy and labored.
Next Jack moved behind her, and was massaging her sweet ass, and rummaging through her cunt. She was about to cum from his ministrations, and there was nothing she could do to prevent it. Finally, Jack announced that he was going to whip Annie’s ass. Jill was ordered to kneel in front of Jack, and suck his cock while he whipped her mother.

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   Jill was quick to drop to her knees, and to take Jack’s cock into her warm mouth. Her free hands were cradling his balls, while she watched as her own mother was whipped by her lover, Jack.
Jack’s whip struck Annie’s ass. Not too hard at first, as he wanted her to become accustomed to his whip. As the whipping went on, the pressure increased on Jack’s whip until Annie was moaning from behind her gag. Jack increased the pressure again, and soon Annie was sobbing. Jack changed direction, and let his whip strike her hanging breasts, causing them to bounce and shudder. The clamps became more painful with the tit whipping. Finally, Jack returned to Annie’s ass area, specifically her cunt. His whip found its target, and Annie felt the full measure of Jack’s whip on her pussy. She screamed from behind her gag as the assault continued.
The whipping stopped. Annie’s hard breathing and sobbing could be heard, as well as the sounds of Jill sucking Jack’s cock. Jack stopped Jill just prior to him cumming. He ordered her to release Annie from the wench rope, but leave her gagged and with her arms still bound.

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   This she did.
Annie stood there. Her face was wet with her tears. Her breasts, ass, and especially her pussy were aflame from the whip. This only raised her level of excitement. Her cunt was boiling over. This was better that she remembered. She eagerly awaited Jack’s next orders for her. Jack took the both of them in his arms and after hugging and kissing them, he moved them to the bed in the corner of the torture chamber.
Jack hugged Annie, pressing her clamped nipples tightly against his chest. Annie moaned behind her gag. While Jack continued to hold her to his body, he reached down and took the spring loaded clamp from her clit. Annie screamed into her gag. As painful as it was to wear the clamp, it was doubly so when the clamp was removed.
Annie was made to lie down on the bed, with her arms and wrists pinned under her.

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   At Jack’s instructions, Jill tied her mother’s legs to the bedpost, spreading them widely. Jack climbed onto the bed, and positioned himself between Annie’s legs. Annie had regained her senses, and was watching breathlessly as Jack knelt between her legs. Her daughter Jill was stroking Jack’s cock, and using her mouth and tongue to excite him, making his monstrous cock harder. Finally Jack was satisfied with the turgid condition of his cock. He moved into position, and shoved his cock into her cunt with one powerful stroke.
Jack was pleased that his cock slipped so easily in Annie’s cunt. Her pussy was hot and wet, well lubricated. It pulsed, squeezing his cock as he pushed into her cunt. Annie gasped through her gag, groaning with pain and pleasure. It was good to feel a hard cock inside her again. Jack’s cock was the biggest cock she had ever felt. She had not been fucked in several years. The fire caused by the nipple clamps made her pussy all the hotter. The excitement of being bound, whipped and fucked by a man like Jack Dillon was almost more than she could handle.

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   She was so excited that she almost passed out. She could see Jill with her hands between Jacks legs, massaging his balls as he fucked her.
This did not last very long. The passion of the moment was too great, and Annie had the first climax she had experienced in years. It was explosive. Her body heaved and quaked as she felt a cum that was so good it was painful, but a beautiful pain that consumed her whole being. The climax just kept on coming in waves, without end. At the height of her climax, Jack pulled the clamps from her nipples. This cause her cunt to spasm into a deeper climax. Annie had lost touch with the world around her. Finally, minutes later, she had exhausted herself, and came back to earth. When she regained her senses, she was still on her back, with her arms still tied and pinned under her, behind her back. Her mouth was still filled with the leather penis gag. She felt that her legs were still secured to the bedposts. When she began to look around, she realized that Jack was lying on his back next to her, while Jill, whose wrists were now tied behind her back, was sitting astride Jacks body, with his cock impaling her.

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   She was riding his cock, lost in a world of passion. Jack had a light weight whip in his hands, and was lightly whipping Jill’s breasts. Annie watched as her daughter rode Jack to a cum to coincide with her own. Jill, after expending herself, collapsed on Jack’s chest, her body still humping his cock.
Annie watch these two lovers, master and slave, as they came down from their sexual high. Tears of happiness welled up in her eyes as she thought about how happy she was at this moment, and this place. She hoped they were as happy as she was. As she thought about what had happened to her this evening, and the commitment she made to Jack, her cunt began to ache for a cock again. She was ready for Jack’s next assault on her. She wondered what would happen to her and Jill. She wondered how deep Jack was going to take them into sexual slavery. She did not care. She was happy. Yes, her aching cunt told her, she was ready for Jack Dillon’s next assault on her.

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