Jill at the age of forty-three didn’t have much in the way of job experience, and found the job market to be quite challenging. She searched around for quite some time, but all she could find were mainly fast food and retail jobs. There wasn’t anything wrong with a fast food job, but keeping up with the younger workers was quite the challenge. She tried it out for a few months, but in the end it was just too overwhelming for her to continue.
Jill had been a cheerleader in high school and college, and was extremely bright and very beautiful. Her green eyes sparkled, and she had shoulder length blonde hair. Her petite 5’3 and 110 pound frame was something special. Her breasts might had been average in size, but were extremely firm. Her butt was small and adorable and there wasn't a man out there who wouldn’t want to be with her. She looked much younger than her age, and she could easily compete in looks with women in their twenties.
Jill worked for a number of charities over the years. She had won several awards for her volunteer work and even was voted mother of the year at her children’s school. If a charity needed help, Jill was there to help. You couldn’t find a better mother or nicer person out there than her.
Jill had been getting extremely discouraged with her job hunting. She had gotten to the point of giving up, when she came upon a story about a woman named Candy. Candy had made money by dressing provocatively in sexy lingerie for men who were willing to pay good money to watch her. She had built her business by wearing sexy lingerie in front of rich men and then prancing around before them while they got themselves off. She had certain customers and they paid handsomely for her services. Jill was shocked at the amount of money that Candy was raking in. It seemed like a very simple taboo idea, but the money was real; to top that off, it was all legal.
A few days later, Jill pulled a piece of lingerie from her dresser drawer. She hadn’t worn it in years and began to wonder if she could even fit in it any longer. She got undressed and slipped on the thin material that barely covered her exquisite body. She quietly stared into the mirror wondering if she still looked sexy, the way she had years ago. She admired herself for several minutes and began to wonder if men would still find her attractive, for an older woman.
Jill never would have thought of doing something like this in the past, but with her son on the verge of college and a second one right behind, she decided to move forward with it. She then came up with an elaborate plan. She didn’t want anyone to know a thing, so she set up a special account with the screen name Amber. Her plan was nearly fool proof and there was no way anyone would ever find out what she was doing in her spare time, including her husband and family.
She had put out a couple of feelers on a few personal sites. She was very specific on what she would do and what it would cost. If someone fit what she was looking for, she would forward a pic of herself in a piece of lingerie. If they were still interested, she would go from there.
A week later she had received a number of interested parties. She went through several of responses, but half of them were looking for some cheap thrill. Jill wasn’t in this for any cheap thrill. Her price was not negotiable and she quickly whittled her list down to only a few. Her goal was to get a clientele of five or so and then see each of them on a regular basis.
One of the gentlemen on her list seemed like a good fit right away. He came to town several times a year on business and was very interested in seeing Jill in sexy lingerie. He also had no problem paying Jill what she had wanted and that made him her first client.
A few weeks later the gentleman came into town for business. He instantly contacted Jill and told her when to meet him at his hotel room. Jill walked into the stranger's hotel room armed with a bag. The gentleman was in his fifties and just wanted a quick release.
Jill walked into the bathroom and stripped her clothes off. She slipped on her sexy lingerie and came out of the bathroom several minutes later. The top was made of thin material and it barely covered each of her beautiful tits. The bottom was a thong and the top draped down just enough to cover her adorable butt. She looked extremely hot and the gentleman instantly put down his cool hard cash on the table. Jill walked over and counted it first. She wasn’t about to be taken by some low life looking for a cheap thrill.
“It’s all here! You get thirty minutes!” Jill said as she turned on some soft music.
Jill began to put on a show for the man. He had his cock out of his pants and was stroking hard on it while watching Jill’s every move. Jill looked like a pro and she teased the man mercilessly with her delightful body. It had been more than twenty minutes later when Jill bent over just a few feet from the man while he sat on a chair in the corner of the room. He was pounding hard on his cock when Jill slowly raised up her top showing off her thong bottom. This instantly sent the man over the edge and he began to cum hard all over himself.
Jill felt a sense of commandment and control. She was getting into this. The man thanked her and told her he couldn’t wait until the next time he was in town. Jill walked out with her first gig under her belt and a nice payday to boot.
She quickly found another client a few days later. He also was in town for business and she visited him the next day. She again put on a show for him and before she knew it she had earned another nice payday. This was almost gold for her, and a month or so later she found another client.
Six months passed, and Jill had gained five regular customers along with a few other stragglers. She had everything in her control, but then greed began to take over. She agreed one day with one of her regulars to go a bit farther than previous times. He was willing to pay more and Jill wasn’t about to walk away from the cash. He wanted Jill to show him her tits while he stroked off. Jill slowly teased him to the point that his cock was ready to explode. She then pulled down her top just enough and showed the gentleman her firm naked tits. This instantly pushed the gentleman over the edge and he began to cum extremely hard while staring right at them.
Her other clients also wanted more from her, and for extra money Jill began to show them a good time also. She had gotten to the point of stripping totally naked in front of them, only to watch them jerk themselves off right in front of her. She even showered in front of one of them on another occasion. She ran her hands all around her wet beautiful body while the gentleman stood just outside the glass enclosure. She was really into it that day and gave him the biggest thrill of his life. She had pushed her gorgeous ass up against the glass shower and bent slightly over. The gentleman on the other side of the glass then cried out as he came extremely hard up against the glass enclosure.
Jill’s income began to explode, and with her regulars and a few outside of that, she had made more than enough money not only to pay for her son’s college, but enough to secretly stash some money away. She still wasn’t happy though and wanted to make more.
One day, she got an email from a gentleman who she hadn’t heard from before. He had gotten her name through some mutual associates. Jill already had enough clients. She was milking them for quite a bit and really wasn’t looking for anymore right that second. She told the gentleman that she wasn’t interested and thought that would be the end of it.
A few days later the gentleman contacted Jill once again. She again told him she wasn’t interested, but that quickly changed when the man told her he wanted two hours of her service. He then offered a dollar amount that blew Jill away. It was a tremendous amount of money, and Jill seriously began to think about it. The next day Jill agreed to the gentleman’s terms. He would get Jill for two hours straight without any limitations. Jill vowed never to let a customer touch her or worse yet fuck her, but she gave up all of that for money. The gentleman also offered her a bonus on top of that if she performed to his liking.
The man came into town a few days later and Jill met him at a plush hotel. The gentleman was nearly sixty and was in extremely fit condition. He handed Jill a wad of cash and she quickly began to go through it. It was the amount they had agreed upon, and Jill then went into the bathroom to change.
She came out of the bathroom a few minutes later. The gentleman’s two hours had started and Jill began to put a show on for him. About ten minutes later, Jill heard a sudden knock at the door. She began to panic and did her best to cover up while the gentleman got up to open the door. In walked a young twenty year old hunk. He stood a good 6’2 and was over 200 pounds. He had a chiseled body, and his muscles bulged outward from it.