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Jill a Mom of Two Does the Unexpected

At forty-three Jill finds a way to make money by wearing sexy lingerie for men, only to get greedy.
Jill was a stay at home mom of two teenagers, and had been married for more than eighteen years. The economy over the past few years had taken its toll on the family. She decided now, with the kids getting near college age, that it was time for her to find a part time job to help out. Anything would work, just as long it gave her the freedom to continue on with several of her volunteer projects.

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.

“This is Matt! He is going to be your partner for the next two hours. I think you are going to like him.”

Jill had no idea what was about to happen and the gentleman went on to explain. He told Jill she looked just like his wife. He explained that they were both about the same age and had bodies extremely similar to one another. He had been wanting to see her with another man for some time now but she wouldn’t go through with it. He now wanted Jill to fill in that void that he so desperately wanted to experience.

Jill was stunned and began to regret her decision, but it was all too late. She had already taken the money and now must perform what she had promised. The young man then undressed, showing his thick beautiful body to Jill. He suddenly yanked down his briefs, and the most beautiful cock appeared. Jill had never seen a cock that size before. It had to be a good 9 inches in length and was extremely thick. It was smooth and heavy looking, and Jill now began to sweat. She knew she probably would need to go along a darker path than any time before in her life, but never in her wildest imagination did she expect to have to fuck a young stud.

The older gentleman’s demeanor suddenly began to change. He now said to Jill, “Strip! I want to see you naked in front of him.”

Jill released the thin material that barely hung to her body and it harmlessly fell to the floor. She then slithered down her bottoms to the floor and now was totally naked in front of this young hunk.

“I want to see you fuck her good and hard. I want to hear her scream out with orgasm after orgasm,” the gentleman said to Matt.

Matt now pushed Jill to her knees in front of him. Jill looked up at Matt’s big thick cock and it began to harden right in front of her.

“Suck it!” Matt said seconds later.

Jill wrapped her hand around the circumference of his large cock. Her small hand barely made it all the way around it and she began to stroke on the shaft of his cock. A few minutes later with his cock hard and throbbing Jill opened her mouth and guided his cock into it. His cock filled her small mouth and she did her best to suck on it. In the meantime the older gentleman had pulled his cock from his pants. He began to stroke lightly on his cock while Matt rammed his cock in and out of Jill’s mouth.

This went on for several minutes until the young man had enough. He yanked his cock from Jill’s mouth and picked Jill up with his strong arms. He brought Jill over to the bed and laid her down onto it, then climbed on top of the bed. He went down in between Jill’s legs with his head and began to tease her swollen pussy with his long tongue.

He sucked on her aroused pussy for several minutes, bringing Jill to the brink of orgasm a number of times. He wouldn’t let her cum; Jill was at his mercy. He then slid up her body sucking each of her tits while positioning his body against Jill’s. Jill felt a wave of energy come over her, and the young man pulled her legs wide apart and now had his hard cock up against her wet pussy. He began to push his large cock against her swollen lips, and then with one hard thrust he pushed his large cock deep inside her. Her pussy was stretched to its max, and she instantly began to cry out while she squirmed hard on the bed.

“Give it to her!” the older gentleman moaned out seconds later.

Matt now began to ram several inches of his cock deeply into Jill. She had never felt anything like this before, and before she knew it she was on the verge of cumming. She began to cry out, when all of a sudden her body began to tighten up. She could no longer take it, and she began to scream out into a very intense orgasm right there on the bed.

The young man gave it to her hard for another few minutes before removing his cock from her. He now got up off the bed and stood off to the side of it. He pulled Jill’s petite body over to the edge of the bed and once again thrust his cock back into her. He gave her several hard thrust with his cock before lifting her body up off the bed. He now stood there holding her body firmly while Jill’s body slid up and down on his cock. He walked her over toward the older gentleman. Her back was to him and he watched from close up while Jill’s body moved in unison with her young lovers.

“Make her cum in front of me!” the man demanded.

The young man began to pump his cock hard into Jill while she held tightly onto his body. Her arms were wrapped around his neck and her legs were strapped around his waist. A few minutes later Jill began to cry out, “Oh god! Oh god!”

She began to orgasm once again, and her screams could be heard throughout the hotel room. Matt now laid Jill down onto the floor in front of the older man. He pounced on top of her and began to pound his big cock into her again. He fucked her hard right there on the floor for a good ten minutes. Jill cried out the whole time, and she once again screamed out into another powerful orgasm just a short time later.

Matt now made Jill get onto all fours. Jill, already worn out from cumming so hard, knelt there on all fours in front of the gentleman. The young man now slid in behind Jill and grabbed firmly onto each of her hips. He then slid his huge cock back into Jill’s tight hole and began to fuck her extremely hard. The sound of his big balls pounded against Jill’s ass and her screams filled the room, and the older gentleman continued to stroke gently on his throbbing cock.

Several minutes later, Jill screamed out into an earth shattering orgasm. The young man was on the verge of cumming along with the older gentleman. Matt gave Jill several hard thrusts with his cock before pulling it from her pussy. He began to shoot several streams of cum all over Jill’s back and ass while the older gentleman stroked feverishly on his own cock.

The older gentleman was on the verge of cumming when he said, “Move her head over to my cock!”

The young stud grabbed the back of Jill’s head and moved it onto the man’s lap. He pushed Jill’s mouth down onto his throbbing cock, and seconds later, the older gentleman’s cock began to explode. He shot his load into Jill’s mouth, forcing her to take his load.

A few seconds later the young man let go of Jill’s head. Cum now slithered down the shaft of the man’s cock while Jill went into the bathroom to clean up. She returned again several minutes later and was once again ordered to suck on the young stud’s cock.

His cock was nearly hard already, and he forced his big cock down Jill’s throat to the point she began to gag on it. This went on for some time before the older gentleman finally said, “Fuck her again! Make her scream out!”

The young stud laid Jill down onto the bed and once again began to pound his cock deep into her. Jill instantly began to cry out and she felt waves of pleasure come over her. She began to cum once again just minutes later, and now the young man had her get on top of his cock.

Jill slithered down onto the shaft of his big cock and rode hard on top of it for several minutes. She was really into it and began to cry out, “Oh god! Fuck me! Fuck me!”

She again screamed out into another orgasm just minutes later. Her body was extremely aroused and the young man made her get into the doggie position. Jill struggled up onto all fours and pushed her small tight ass back toward the young man. He rammed his cock back into her from behind and began to fuck her hard on the bed.

Several minutes had passed when the older gentleman said, “I want to see you fuck her in the ass!”

Jill had been fucked in the ass only a few times before in her life and definitely not with a cock the size of Matt’s. Matt slowly pushed the head of his cock up against Jill’s tight hole. He gave her one hard thrust and his cock slid deep inside her ass. Jill instantly let out a loud cry and the older gentleman now began to once again stroke on his cock.

“Harder! Harder!” the older gentleman moaned out.

The young stud now began to pound his cock into Jill’s tight ass. Jill felt a huge amount of pain at the start, but now she felt a powerful wave of pleasure come over her.

She cried out, “Oh god! Oh god!”

She had been crying out for several minutes, when she had one of the most powerful orgasms of her life. Her ass quivered hard while the rest of her body shook violently on the bed. She no longer could stay up on all fours and her body collapsed down onto the bed.

Jill lay there almost out of it and in no condition to be fucked anymore. The young man turned Jill over onto her back. He knelt over top of her chest and began to stroke hard on his cock. A minute or so later he began to grunt out loudly. He began to cum hard all over Jill’s chest and face while the older gentleman watched on. This pushed him over the edge also. He began to cum once again all over himself while a moaning Jill laid there on the bed trying to get her composure back.

Jill struggled to her feet several minutes later. The two hours were up and she went into the bathroom to change. She came out a short time later, and the older gentleman handed her an envelope stuffed with money.

He said, “Here is a bonus! I hope we can meet again next month.”

Jill made a nice haul that day, but she also gave up herself to this man’s desires. She wondered what he had planned for next time.

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