Story Details

Jack and Jill

Sir James on Forced Stories

Jack Dillon was in the prime of his life. At 40 years of age he was successful at business as well as being self assured about life. Dillon Air Charter was his baby. His fleet of airplanes consisted of a Beech King Air 300, two Lear 45 Longhorns, as well as one small twin engine, six passenger pressureized Beech Baron. His clientele was vast and required the services of his air charter company on a frequent basis. He was even contemplating adding a Gulfstream G5 to his fleet to meet the needs of his overseas contracts. To say life was good would be an understatement. His Love Field, Dallas, Texas based operation was pouring a lot of money into his bank accounts. Oil men and computer engineers seemed to have a lot of traveling money, and wanted to travel a lot.

Jack, however, was aware of an emptiness in his life. He had been married, but Sarah proved to be an ice queen. After several years of an off and on again marriage, they were divorced. Jack plunged into his business, working 20 hours a day. This hard work was paying off. Now, he would like to fill the emptiness in his life.

After his divorce, Jack recognized that he was a different individual. In plain words, he was sexually dominant. In the years since his divorce, he had learned that he was very interested in the arts of Bondage and Discipline, and the predilection for S & M activities. He several close associations with women of similar mindsets, and had even become acquainted with people in the S & M community in the Dallas-Ft. Worth area. A friend of his, who called himself "Sir Steven", had set him up with several dates, all of which had proved to be very exciting. However, Jack had failed to meet that special woman with whom he wanted to spend his life.

Jack was in his office early that Tuesday morning. He had just returned from an all night flight from Bogota, Colombia. He hated to go to Colombia, because the return flight was generally a hassle. U. S. Customs Service would always want to thoroughly check Colombian flights. This was no exception. The flight had been complicated by Hurricane Jill which was churning up the eastern Gulf of Mexico, requiring Jack to fly around numerous embedded thunderstorms. When he got into Love Field late, the client was complaining about the rough flight, and the Customs agent had been a complete bastard.

As Jack was setting at his desk, completing his logs, he heard a knocking sound at the outer door to his office. It was too early for his secretary, and none of his other pilots were due in until later. Jack got up from his desk, with a grumpy grunt, and went to the door. Much his surprise, there stood Jill Cates. Jill was a delightful creature. She was only about 5’4" inches, with about 115 pounds of delicious curves. Her long dark brown hair, worn with bangs, hung over her radiant blue eyes like a soft cloud. Jack always thought she looked a lot like the revered Bondage model, Betty Page. Jill was also the accountant at New Iberian Oil Corporation.

"Well…, are you going to invite me in?" she asked, "It’s raining out here!":

Jack smiled, "Yeah, come on in, Girl. It’s a little early, and I wasn’t expecting company. What can I do for you this morning."

Jill grinned and replied, "Well, Sir, it is not what you can do for me, it is what I can do for you. I have a check for you from New Iberian for last month’s charters. We flew a lot with you, and we owe you a lot of money, so I thought I would drop it off this morning on my way to work"

With that she handed him an envelope, which he opened. Sure enough there was a check in for $175,000.

"Wow, I didn’t realize we flew that much for you guys, but now that I think about it, I guess we did. Thanks Kid, I appreciate it. My pilots love to get pay checks."

Jill just stood here, in her black raincoat, complimented by her four-inch heel black patent leather shoes. Jack thought she was one hot lady, but she was ten years his junior. She was always very friendly to him, and acted like she wished Jack would ask her out. He had considered it. Just looking at her creamy skin, and sweet smile caused his cock to stir in his trousers, even though he was tired from the all night flight.

"I could use a cup of coffee, Jack", Jill requested.

"Uh-uh, sure, come in to my office and sit down. I have a pot going," he replied.

Jill preceded him to his office and set down in the chair facing his desk. As Jack followed her into his office, he could not help notice the lady had great legs, which were enhanced by her high heeled pumps. When she sat down, her black raincoat slipped open, revealing a delightful bit of her legs above the knee. Smiling, she watched him pour her a cup of coffee. At her request, he dropped a couple of cubes of sugar into the cup.

Jill took the proffered cup, and after sipping the hot brew, smiled and said, "I was chilled. This will help."

They sat for a few minutes, passing the time of day, with meaningless conversation. Jack got the feeling that Jill wanted to say something to him, but was trying get up her courage to do so. Finally, with a big sigh, she looked at Jack, from across his desk, and asked "Jack, can I ask you a personal question? Really personal?"

"Well, I guess so. What do you want to know?"

"Jack…look...uh, we have known each other for five years. I think we know each other fairly well. I like you. In fact I like you very much." With that, Jill cast her eyes down, staring into the cup of coffee she was holding in her hands. "I have always thought your were a great looking man, with his head on straight. I have tried to signal to you that I would be interested in going out with you, but you acted like you never had any interest in me. I know you date women, so your are not gay. So, is there anything wrong with me, or you are just not interested in me?"

Jack was taken aback. His mind was on several other things this morning, as well as the fatigue experienced from the Bogota flight. He collected his thoughts, and replied, "Well, I guess females named Jill are going to dominate my life today. First there was Hurricane Jill taking a swat at me last night, and now I have a Jill in my office, stirring up my life."

"Jack," she said, "I don’t want to complicate you life. Maybe this is a bad time. I just had to ask."

"No, it’s alright, just took me by surprise," he answered.

Jack was silent for a minute, and after sipping some coffee from his cup, replied, "Lady, let me put it this way. You are quite a bit younger than I am. I never thought you would be interested in me because of my age."

"Jack, I never considered any age difference. You are a vital man, and ONLY 40 years old. I find you exciting, and I thought we would hit it off just right."

"Ok, ok," he slowly replied, "but there is another problem that dictates any relationship I may have. Look, you are a beautiful and bright woman, who appears to want a career, and to control her own life. I, on the other hand, am a dominant man, especially in my sex life. I am a very dominant lover. A great number of women would not like a man like me. I will not push myself on any woman. However, I need a submissive woman in my life. I do not apologize for myself. I just know who I am, and what I expect in a woman. At this time in life, I cannot change. I am who I am."

He thought for a minute, and said, "I would have been very excited to take you out, but I did not want to ruin the friendship we have when we found that it could not work out."

"Would you explain to me what you are looking for in a woman?" she asked, with an expectant look on her face.

"Oh, God, Lady, you don’t really want to know about the darker side of me!" he answered.

"Yes, Jack. Yes I do. I really like you a lot. It would have to be something really bad for me to lose interest."

"Well, OK, you asked for it", Jack sighed, "In a nut shell, I am a dominant kinky bastard. I like my woman to be subservient, slavish if you will. I would tie her up, whip her, torment her, and not allow her to say no to any sexual advance. At home I would not allow her to dress. She would be kept in the nude, and dress only how I wanted, no matter how revealing. I have friends who are into Bondage and Discipline, S & M. I like the life style, and want to live it."

Jack looked back down at Jill, saying, "Now you asked. You have no right to be angry. In this world of feminism, I am an anachronism. I realize this, but I also realize who I am, and my needs. I would not foist them on another person. As a result, I never asked you out, because I did not think you would like my desires and wishes. I like you very much, and value your friendship too much for that. You asked, so now you know. I would say off hand, that the smartest thing you could do, is to get away from me. Run away from me, as fast as you can!"

"Oh, Jack, if you only knew me as well as you think you know me", she replied, with a nervous smile on her face. "I know "Sir Stephen". I am in the closet with my desires and feelings, but I have confided in him. I also know that you are friends with Stephen. I mentioned to him how I feel about you. He then told me about you and your desires. I think we have the same interests, naturally I am submissive, very submissive. I have never acted on my desires. It is frightening to be at the mercy of someone you don’t know or trust. Jack, I trust you, and I need you to know who I am, and how I feel. I have dreams and fantasies about being under the control of a strong dominant lover, who will enforce his will on me. When I heard that you were of the same mindset, I could have fainted with excitement!"

The room was silent, as if both Jack and Jill were trying to digest what had just happened. Jack slid his chair closer to his desk so his hard cock would not be visible through his trousers. He log hard cock was being painfully cramped by his clothing.

"Lady", Jack finally answered. "I hope you know what you are doing. I would love to take you out, and discover what kind of chemistry we have. Look, I have a Customs agent due here any minute. Why don’t we go out to dinner tonight, and discuss this thing in depth. I want you to know exactly what you are getting into."

"Jack, that would be wonderful", she smiled, "Why don’t you pick me up at 8:00 o’clock, and lets get really acquainted."

With that, Jill stood, blowing Jack a kiss, turned on her heel and headed out the door, into the morning rain. Jack’s erection was now very painful.


The seating in Durado’s was intimate. Jack Dillon had secured a table in a quiet part of the restaurant. Jill had been waiting in front of her apartment building, waiting in anticipation for him to arrive. She was magnificent. Jill had dressed in a black silk blouse, and a black leather mini skirt. Her dark smoke hose, and black leather 4 inch pumps matched beautifully. Over her arm, she carried that same black raincoat she had worn earlier in the day. Her legs were on display with the short skirt. Her breasts were obvious, outlined by the black silk blouse that seemed to be tailored to her body. She was in fact, a very beautiful and hot looking woman.

When Jill seated herself in Jack’s car, her skirt slid up her thigh, revealing that she was not wearing panty hose. The tops of her stockings were clearly visible.

Now they were in the restaurant, with waiters buzzing about, taking drink orders and pouring water. Finally their drinks were served, and the two began to talk about themselves, exploring their secret lives. Jack patiently explained that he expected any woman he picked to be his significant other would have to understand his desires. She would want for nothing, and would give everything. She would be virtually, and in actuality a sex slave. She would forsake any right to say no to any sexual advances or to any restraints or torture inflicted on her.

"Jill, the things I do to women who consent, would put me in jail if we were strangers, or if she did not consent to what we were doing. If you want a relationship with me, that is how it would be. If your have any doubts, we had better stop this thing now."

Jill, was quietly listening to Jack. As he finished, the waiter brought their meal orders. The conversation stopped and the waiter fussed about, making sure everything was as it should be. Finally, privacy was restored.

"Jack, I am a novice. I am excited about having a relationship with you. I will do as you want. Just be patient and teach me what you want me to be", was her answer.

Jack took a bite of his veal, and turned to Jill. "If you are serious about obeying me, I have a request for you."

"What is it", Jill asked.

"I want you to get up, right now. Go the restroom. There, I want you to take off your bra, and panties. You may fold them up in you hand, but do not hide them. You are to bring them back out here, and hand them to me! Do you understand?" he asked.

Jill swallowed, and then nervously replied, "Yes, Jack, I will do as you ask."

With that Jill stood up, threw Jack a kiss, and strolled across the restaurant to the Ladies room to accomplish her designated task. Jack watched her beautiful body and great legs, shown off by the short skirt and very high heel pumps.

In a few short minutes, she returned to Jack’s table. It was obvious that she had taken off her bra. Her breasts, which now seemed larger after being freed from her bra, swayed and bounced as she walked across the room. In her hand was her bra and panties as Jack had ordered.

She sat back down in her chair, and deposited her bra and panties on the table between her and Jack. Smiling, Jack picked up the undergarments, and put them in his coat pocket. He looked back at her, and said, "Now, I never want to see your blouse buttoned up that high. You are never to button your blouse above the level of your nipples."

Jill slowly unbuttoned her blouse to the required level. The nearest allowed button was just below her nipples. She looked down and discovered a lot of her breasts were on display. In fact, if she leaned over too far, her complete breasts might be visible.

"That’s good, Lady. Now pull your skirt up so the tops of your stockings are on display."

Jill did as she was ordered. Jack leaned over the table and taking her face in his hand, kissed her. Jill nearly melted. His kiss was every bit as good as she thought it would be. She was excited, and would do anything to please Jack.

They ate their meal, with Jack stroking her thighs and in general letting her know he was satisfied with her response, and was looking forward to the rest of the evening.


The trip back to Jack’s house was intimate. As Jack drove, he stroked her thighs and brushed her breasts. As ordered, she had pulled her skirt up to her waist, displaying all of her stocking legs and her pussy. Likewise, her blouse was now unbuttoned to her waist. Her breasts were completely exposed. He informed her that this is how she was to be arranged any time they were alone in the car.

She rode with her hand on his thigh and stroking his erect cock through his trousers. He would not allow her to do anything more intimate. It was as if he was teasing her, building to the evening at his place.

On arrival to his house, Jack escorted Jill into the den. It was cozy, with a large fireplace. The room was clearly masculine, yet very tastefully done. After Jack lit a fire in the fireplace, he poured glasses of wine for them both. They sat on the couch, with their bodies touching. Jack savoring the moment, with Jill waiting in anticipation of what Jack would require of her. The wait was short.

"Jill, I want you to stand in front of me", he requested.

Jill rose from the couch, and stood about six feet in front of Jack, facing him, with a nervous, but excited look on her face.

"Take off your blouse, and skirt", he ordered.

Slowly Jill took off her blouse. Her spectacular breasts swayed into view. Jack had always thought she would look good in the nude, but never this good. Next her skirt came off. Now she was wearing only her garter belt, hose and heels. Her pussy with a delicate thatch of dark brown pubic hair was delightfully displayed. She was a magnificent creature. She moved her hands behind her back in a motion of submissiveness. This accentuated her breasts. She was a dream. Jack thought that maybe he should pinch himself to make sure it was not in fact a dream!

"Jill, if you would, go to the antique chest over by the bar, and open the top drawer. There you will find several coils of rope. Bring me at least three of them", was his next order.

Jill complied. The drawer was filled with all kinds of restraints. She caught a glimpse of steel handcuffs, leather wrists cuffs, and of course, the standard white cotton rope. She retrieved the requested strands of rope and took them to Jack. On his orders, she turned her back to him and placed her hands behind her back, crossing her wrists. Jack was quick to bind her wrists tightly in that position. Another strand was placed around her elbows. She gasped as he tightened the rope, forcing her elbows together in the small of her back. It seemed to her that her breasts exploded on her chest. With her elbows tied like this, her chest, and subsequently her breasts were force out. This excited her as it forced her breasts to be more vulnerable, more available to Jack. Jill was almost dizzy with erotic excitement.

At Jack’s instruction, she stood there, turning about so Jack could look at her. She blushed as she saw at the excitement on Jack’s face. It was obvious that he liked what he was seeing. He walked to her, and took her in his arms, holding her tight, kissing her, nearly smothering her with excitement. As he was kissing her, he turned her slightly so his hand could find her up raised breasts. He kneaded them, pinching her nipples, twisting and pulling on them. His other hand slipped down to her ass, squeezing each cheek, and slipping his finger into the crevice, tickling her little ass hole. Jill nearly fainted with excitement.

Jack then led her to the couch, where he sat down. He then pulled her over his knees. "Jill, I am not angry with you, but I am going to spank you magnificent ass. I’m going to spank it because it is beautiful, and because I want to. You may cry or scream if you want to. The room is soundproof."

With that he started to stroke her ass cheeks. His hand moved between her inner thighs where he found her smoldering pussy. She was hot. Her pussy was a caldron of sweet hot juices. Jill thought she would come if he continued to rummage through her pussy like this.

Finally, Jack moved his hand to her ass, and started to spank her. The swats became harder, and the heat on her ass rose. That heat was being translated directly to her pussy. Jack struck harder, causing her to gasp, and whimper. Finally she began to sob. She tried to keep still, and she struggled to do so. Her ass was now on fire. Still she struggled to stay in position. The heat in her pussy was now volcanic.

At long last, Jack stopped her spanking. He pulled her off his lap, and placed her in a kneeling position on the floor directly in front of him. He unbuttoned his trousers, and extracted his cock. Jill was both surprised, and pleased at its size. It looked wonderfully menacing. Jack pulled her up to a upright kneeling, in front of his sitting position on the couch. They were face to face, tears from her spanking moistening her face. He pulled her to him, sliding his rigid cock between her thigh’s, rubbing against her scalding pussy.. Jack was pinching her nipples and squeezing her breasts. From time to time he would slap them, causing them to quiver and sway. Jill was quietly whimpering with excitement as Jack abused her.

Finally, Jack pulled her face, still wet with tears, to his and kissed her long and passionately. Jill kept rubber her cunt against his cock. He ended the kiss, and waited for Jill to regain her breath. She was gasping for air, as she was sliding her pussy back and forth on his cock.

Jack, looking deep into her eyes, asked, "Jill, I want you to be my slave. Do you submit, and give yourself to me, completely as my naked bound slave?"

"Oh God, Oh God", she cried, "Yes! Jack, I want to be your slave. Yes, do it, I submit. I am yours!"

Jack smiling, and stood up in front of her, with his cock in front of her face. "Suck it!" Jill kissed the head of his cock, and the slipped it into her mouth. She was like a hungry terrier, worrying a bone. She could not get enough of his enormous cock into her mouth. She was totally consumed with the moment.

Jack, then pulled his cock from her mouth, and assisted her to her feet. In her excited haze, she was tottering on her high heels. Jack took her by the arm to steady her, and again he kissed her long and passionately, while his other hand was squeezing her breasts. As she regained her balance, he moved his hand to her pussy. He took a hand full of her curly brown pussy fur, and pulled on it. When he heard her gasp from the pressure, he whispered in her ear, "It’s time for you to be royally fucked!"

With Jill struggling for her senses, Jack was pulling on her pubic hair, using it as a leash to lead her to his bedroom.


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