Jennifer in Chastity

Some of Jennifer's friends had told their secret to affording college. They had found sugar daddies, older men who paid for their college tuition and expenses in exchange for sex. Amy, Jennifer's best friend was bedding a local banker and was doing very well indeed. Freed from the financial burden of massive debt from college loans, and with her sugar daddy's many gifts, she expected to leave college with money in the bank and no regrets. Amy claimed that older men were better lovers; they were not all hands like college boys and really seemed to understand how to turn a woman on.

Jennifer was leery, but after taking out another loan, and losing her part time job, Jenny realized that her future would be debt filled and financially difficult if she did not act fast. Her parents were in no position to cover any of her tuition. Jennifer was not excited about exchanging sex for security but she saw no alternative. She asked Amy if her sugar daddy knew another man who might be interested in a young and nubile college girl.

Jennifer knew that she was at least as pretty as Amy. Jennifer had long black hair and porcelain skin, her bowed lips and pert nose made her face rather photogenic. Her legs were long and she was in excellent shape. She felt her bust was a bit small but Amy told her that sugar daddy's sometimes sprung for botox or breast augmentation. It seemed too good to be true.

Jennifer did not feel a connection to the first man Amy had set her up with. He was a banker friend of Amy's paramour. He was nice enough but he was fat and had really let himself go. Jennifer had met Amy's sugar daddy; HE was handsome and looked younger than his years. Jennifer thought that there was no reason that she should have to settle for less than her friend did. After all it was a seller's market and she was the seller.

Jennifer placed some personal ads and soon went on a series of dates with older men. On her fourth date she met Dennis. He was handsome and young looking and utterly charming. He was a hedge fund investor for one of the largest local corporations. Best of all, although clearly interested in her, he made no overt sexual moves on Jennifer. She thought that, perhaps Dennis was shooting blanks or didn't believe in Viagra. If so, Jenny had thought that she had hit the jackpot. She could have all of the benefits without having to put out! She would be the envy of her friends. She had two more very wonderful dates with Dennis. Jenny did notice that Dennis had a hard on at the end of their subsequent dates. She concluded however that Dennis was a gentleman.

On their fourth date Dennis took Jennifer home and gave her a tour of his handsome house. It was not an especially large house but it was in the town's most exclusive neighborhood. The furniture was wonderful and expensive. The shag of the carpet felt divine under her feet. A high end Beemer was parked out front. It had a hot tub out back and a small pool. Dennis explained that he had downsized since his wife had passed away. At last they were in his lavish bedroom. Jenny noticed the huge bed with the satin sheets. At her host's urging Jenny checked out the bed. It was wonderfully comfortable. The two made out on the bed for a while and then Dennis cooked a spectacular meal for the two of them. As they ate they talked.

"Jennifer, do you think you could find room in your heart for me?"

"Oh yes Dennis I am sure I can."

"Well Jennifer we need to discuss business. You would like me to pay for your college tuition. How would you like me to cover tuition and give you an extra three hundred a week as spending money?"

Jennifer was stunned. It was far more generous than she had even hoped. Why she could get a new part time job at the mall and really rake in the cash. And all she had to do was spread her legs. Jennifer was so happy that she was a woman. Abstractly she wondered how her male peers paid for college.

"That would be more than acceptable Dennis. In fact why don't we..."

"Don't you want to hear the fine print Ms. Sampson? In exchange for those things I get sole access to you while you are in college. You will be required to study hard and get good grades and that means that you will not be permitted to fraternize with college boys. I will take care of you Jennifer but your body will belong to me." He took a long look at Jennifer and asked her. "Are you familiar with chastity?"

"Chastity?" replied Jennifer.

"Chastity: a device that you will wear about your loins. It will have but a single key and I alone will possess that key. Your sex will be mine and mine alone to control. That is nonnegotiable. If you agree to be my property, I will lavish you with gifts. How about a hot little convertible? I'll pay for the insurance and the gas. I will give you a spending allowance for clothing and shoes. You will lack for nothing and you will learn self-control and self-discipline. The sex, when we have it, will be phenomenal. I also will have control over your mouth. I expect a great deal of fellatio as that is my very favorite thing sexually. I WILL see to your needs but for the next three years you will belong to me and MUST apply yourself to seeing that I am well taken care of. You will be mine completely, utterly, and without equivocation." He paused for moment and then said. "Do you think you are up to it Jennifer?"

Jennifer's mind reeled. On the one hand the gifts seemed incredible on the other hand... "You want to lock me up in a chastity belt?"

"Precisely! It is a guarantee for BOTH of us. For me it means that you are not engaged in dissipation or wasting your charms with boorish college boys. For you it is an act of submission that guarantees your wonderful financial gifts keep coming. It's a win-win for both of us."

"But my friend Amy doesn't have to ..."

"I care not what other arrangements your friends may have with their paramours. I am a man of particular and rigid tastes. You KNOW that I have the means to provide you with everything I promised. IF you are not interested in those wonderful gifts, well this town is full of college girls. I'm certain I can find one who is far less picky"

"But Dennis darling, what difference does it make who I sleep with as long as I keep you happy? Why don't we retire to that huge, comfortable bed of yours and I can show you how well I can take care of you."

She smiled fetchingly at the graying but ruggedly handsome fifty five year old man seated across the table from her He returned a sober expression.

"Ms. Sampson, Jennifer, I do not believe in renting I OWN. Take a look at this house. I own it and all of its contents outright. I have no mortgage, I have no debt, I am beholden to know one. People trust me with their money because they understand that I know how to handle it. If I am going to invest in you then it will be like every other investment I have ever made, it will benefit me or those I work for.

If I cannot own you, I have no interest in a relationship with you."

"But Dennis darling you can TRUST me."

"Jennifer, as a great president once said, 'Trust but verify'"

"But Dennis if you lock me away, I may come to resent you and not be as pleasant as BOTH of us would like me."

Dennis laughed and said "I could care less if you 'love' me or not. This is a business proposition from my end. You may think that you have final say in things but I am very well connected. There are only so many available men of my means or better in this town and I know a fair proportion of those. You may think that you are in control of what you naively believe to be a "sellers" market. But a whispering campaign started by me would mean that not one of them would look twice at you. Oh they would take you a roll in the hay and buy you a few baubles but paying for your college tuition? Not in a million years! When things are on my terms, I am quite the pleasant fellow. I shower the ones I favor with affection and spectacular gifts. But it MUST be on MY terms."

Jennifer was getting quite uncomfortable. She wanted no part of a chastity belt but she had no doubt that Dennis' threats were genuine. Jennifer had done her homework; the number of men who could afford to support her was narrow. Jennifer knew she needed an unattached man of middle years who was good looking and very well off. Jennifer had ruled out married men because they had to divide their income and Jennifer was afraid encountering an irate wife. A wife could make a lot of trouble for a mistress. It could mean a sudden end to the affair with the college girl left high and dry and suddenly needing to pay bills and tuition again. That would mean starting over and Jennifer wanted something that would last her entire college career.

Jennifer had noticed a Cobalt Club membership badge on Dennis' BMW. The Cobalt Club was this city's most exclusive and expensive club. Jenny knew that the men who frequented the Cobalt Club were the very same men that could provide for her financially. But IF Dennis poisoned the well...

"Dennis darling, why don't we retire to your bedroom? I think that you will find me a wonderful and graceful cat like creature. One who will not do well in captivity."

"Jennifer DARLING if we fuck tonight your pussy becomes my property. I will measure you for your device and it will be delivered in a few days. You will then be locked up and liberated ONLY when I decide. That is how it will be my little college freshman. Now that we are finished dining I will give you precisely one half hour to make up your mind. I am going to retire to my bedroom and read a bit of the "Financial Times" If you want to become my property you will enter my bedroom stark naked before the half hour is over. If you want to return to your life of poverty and massive student debt you are free to let yourself out, I'm sure you can find the front door. IF you decide to leave, you will be subject of conversation at my club. The words uncooperative, selfish, and passionless will be mentioned quite often. Try selling yourself after every rich man in this town decides that you are bad news."

With that Dennis stood, smoothed out his tailored suit and made his way towards his lavish bedroom. Jennifer watched him go with butterflies in her stomach. She realized that the man was painfully serious. She watched the bedroom door close behind the businessman. Alone in her seat in the kitchen Jennifer's mind preformed the delicate calculus of financial opportunity versus total submission. Jennifer was still young enough and pretty enough, and naive enough to believe that her charms could bend any man to her will. Jennifer concluded that the chastity belt was just a temporary kink on Dennis' part and that once he tasted her succulent charms, he would instantly see things HER way. Jennifer took a long look around the kitchen and then rose to her feet and explored the house. Where a wiser, more mature person would have seen determination and iron will in amassing so many fine things without the burden of debt, Jennifer saw only dollar signs and imagined her partaking in this luxury. Jennifer had definitely read too many romance novels and seen too many Disney movies with princesses. Convinced that she could change Dennis, Jennifer approached the bedroom and began removing her clothes.

Dennis allowed himself only the briefest of smiles as he espied the slim, dark figure enter his bedroom. Naked, Jennifer was just as fantastic as Dennis had imagined. She approached the bed smiling sweetly and trying to amplify her every charm. Dennis decided that Jennifer's only flaw was that she was a bit undersized in the breast department. Her tits were very nice, just a bit small for her frame. "No matter," thought Dennis. "I'll buy her new ones." Jennifer's legs were long and fine and she had wonderful hips. To Dennis' delight she had clearly recently had a total body wax. Her bald pussy looked like it would taste better than ambrosia. He would take supreme delight in controlling this girl. Dennis knew that he could train her and have a wonderful time with her.

"Dennis darling, what can I do for you?" she asked coyly.

"You can enter this bed and start sucking on my manhood. If your skills at fellatio are lacking I will have no other need of you tonight. Impress me with your lips tongue and mouth and I will show you how a gentleman makes love to a beautiful woman. Once I have taken you you're mine until graduation day."

Jennifer realized that Dennis must have been sure of her submission as he was naked under the sheets. Jennifer had deduced that Dennis was well endowed but she was unprepared for the sheer length and girth of the uncut penis before her eyes. Jennifer kissed the length of the shaft, liked the phallus a few times and then began to preform and amazing session of fellatio.

Dennis was delighted. Although Jennifer was young she knew her way around a cock. He made encouraging comments and stroked Jennifer gently and lovingly as she worked. Gently he clasped Jennifer's face as he came. He issued one command, "Swallow."

Dennis could tell that Jennifer would have preferred to spit out the viscous liquid but she gamely choked it down, opening her mouth to demonstrate that she had obeyed the command of the man whose bed she was now sharing.

"Good girl Jennifer! Now I am going to massage and pamper you until I am ready to preform once more. I think that you will find me far more considerate and gentle then the shallow college and high school boys you have been with previously."

Jennifer was amazed by the older man's touch. Never before had she enjoyed a more pleasurable massage. Like a skilled therapist Dennis stroked and rubbed her body. Once she was on her back Dennis' gently nibbled her breasts and soon demonstrated to the college freshman that he was the most skilled man at cunnilingus she had ever encountered. Her friend Amy was so correct, older men were the best lovers. Under Dennis' skilled tongue Jennifer experienced one of her finest orgasms ever.

Then, at once, his recharged member was plunging deep into her sex. His was the largest organ to have ever entered her. The sensation was amazing as Dennis gradually increased his tempo and then came as Jennifer climaxed. Jennifer found herself relaxing more under Dennis than she had under all previous men for Dennis had informed her of his vasectomy during their first date. It was extremely comforting to know that Dennis could not make her pregnant.

A spent Dennis collapsed into Jennifer's arms and she held him close. She enjoyed the feel of his body. Dennis was physically fit for his age. He looked like an older movie star in his birthday suit. As Jennifer held him close her mind unspooled images of her living in this house and sharing her life with Dennis. Of course there would be a scandal, Dennis was older than Jennifer's own father, but people would get over it. The reverie existed for many minutes until Dennis rose from the bed and returned with a tape measure.

"Measurement time Jennifer. If I expedite the order, your chastity belt will arrive in three days."

"But Dennis ..."

"Ms. Sampson, I explained to you what would happen. Your fellatio skills are more than adequate and your pussy is quite succulent. I shall be delighted to take possession of it and of you."

Jennifer made a move to protest anew but Dennis silenced her.

"Jennifer, if the next words out of your mouth are anything aside from "Yes sir" followed by your standing and allowing me to measure you, our relationship is over. I will give you a nice reward for your time and send you on your way. Of course I will then have you blackballed amongst my fellows."

Glumly, Jennifer exited the bed and stood as Dennis instructed her as he measured much of Jennifer's waist and pelvis. His touch was gentle but firm, like a tailor or a seamstress. After entering a lot of numbers in his i-phone Dennis announced that he was finished.

"Now Jennifer, you are free to spend the night. Tomorrow I will take you a wonderful breakfast. We will buy you some nice outfits and stop by the car dealership so you can pick out your convertible. HOWEVER, aside from the breakfast and probably lunch, you can take nothing home with you until AFTER you are safely secured in your chastity belt. Tomorrow you will see how well I can improve your life, IF you obey me."

Jennifer was a bit disappointed that after she had prepared to bed down for the evening that Dennis snored. Still she had a wonderful night's sleep and woke to Dennis gently kissing and shaking her. The first thing her older lover did next was to place the order for Jennifer's chastity belt. He helped her dress and they went to town in Dennis' fabulous car. Breakfast was at the Cobalt Club. Jennifer had never seen the inside of the legendary club before. It was everything she had imagined; fine furniture, and wonderful art on the walls. The men wore suits and ties. It reminded Jennifer of an exclusive college like Eton or Cambridge. Even though she wore the same attractive black dress she had worn the night before to Dennis' house, she felt woefully underdressed in such a classy establishment.

After breakfast Dennis escorted Jennifer to the finest boutiques in town. Jennifer was familiar with these places but had never imagined that she would ever do more than window shop at these stores. She was treated like a queen. A fashion consultant and a dress designer took Jennifer's measurements and showed her the loveliest fabrics. An entire new wardrobe and new adorable look was prepared for Jennifer. It would take several days for her new wardrobe to be ready She felt just like a fairy princess in one of her favorite stories.

Lunch was equally wondrous. They dined at the town's most exclusive restaurant. Dennis ordered for her, reminding Jennifer that her weight was now HIS concern. Jennifer would have liked to have eaten more but she knew better than to object. The car dealership was fantastic. Jennifer picked out a salsa red BMW convertible, the most expensive one manufactured. Denis did not make a single objection as Jennifer ordered option after option. She never felt so much power as she took the dealer's car for an extensive test drive.

Jennifer gave Dennis a lot of attention when the two returned to his house. She eagerly sucked him off and later let Dennis lead her to bed.

"I take it Pet that you enjoyed the day and liked all of your presents."

"Yes sir!"

"I like when you call me 'sir' henceforth I will be Sir and you will be Pet." Dennis then led Jennifer to a small, but attractive bedroom.

"Now Pet this room will be yours when I either am not making use of you or for various circumstances must host guests without you being present. I will send for some of your things from your apartment. You are not leaving this house again until you are safely clad in your chastity belt. For the mean time I will pay your share of the rent at your apartment. Until I know that you are trainable I will not have you permanently under my roof."

Jennifer was a bit angry. She would have to miss school on Monday and Tuesday. Dennis assured her that he would send a convincing excuse for her.

"Two days do not college careers make. I will have your textbooks sent over. I understand you are taking some basic economics courses. I will be happy to tutor you in that area."

Jennifer did not mind being called Pet but she felt funny calling Dennis Sir. It accentuated the age gap between them. She soon deduced however, that Dennis' term of endearment for her was how he actually felt. "He sees me as his pet, not his equal." Jennifer thought to herself. It was the first of many revelations to come.

Aside from a brief walk around the block Dennis and Jennifer never left the house either Sunday or Monday. Dennis kept Jennifer occupied. After cooking both of them a marvelous breakfast, they worked out together in his well-appointed gym. Jennifer was flabbergasted to discover that fifty five year old Dennis could swamp her nineteen year old self at the stair master and other fitness equipment. Dennis just laughed at her predicament and said,.