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From Cleaning Lady to Escort

"Ashley's hard times gets better."

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Competition Entry: Money Talks
Ashley fumbled through the stack of sealed envelopes she had retrieved from her mailbox. Tears began to whale up in her eyes as each one had “Past Due” stamped in big red letters. She stuffed the envelopes into her bag, and wiped her tears away, and headed off to class.

Arriving for her class late, she took a seat near the door, not to cause any disturbance, but unfortunately her tardiness caught the attention of the instructor. She sank deeper into her depression as he looked at his watch and shook his head. This was not the first time she had been late, actually, her being late was more of the norm. She was trying, but the ends never seemed to meet. She had school, her job at the diner, then she would clean a couple of her instructor’s offices, along with any other odd job she could pick up for extra money. All that and trying to study and make it to class left her with little time for sleep. Even a 19 year old college student needs sleep.

When the class dismissed, her instructor Dr. Cole, asked her to approach his podium. She waited until everyone left the room, and she slowly, with head lowered, approached the front of the room. She listened intently as he explained how important he thought his class was and how important it was for her to be on time if she expected to pass the class. She listened, but she was so tired that she could not comprehend half of what he had said. She nodded, when asked if she understood. Then he smiled and dismissed her. She slowly left the room, and headed for her next class. She knew something had to change, she thought how nice it would be to win the lottery, but then chuckled to herself when she realized that she didn’t have the money to buy a ticket.

After her classes, she went straight home. She was so exhausted. She sat in a chair and pulled the envelopes from her bag and placed them on top of the pile on her table. She lifted her hand and pulled the pony tail holder from her hair. Her dark brown hair fell around her shoulders. She rubbed her hand through her hair and loosened the knots as best she could, before walking towards the bathroom. She had an hour and a half before her shift at the diner started, so she needed to shower to see if it would rejuvenate her. She leaned down and turned on the water, and stuck her hand under the faucet to test it. When the water was to her liking, she lifted her shirt over her head, and tossed on top of the pile of dirty clothes in the corner. Her fingers unbuttoned her shorts, and they fell to the floor. She unsnapped her bra, and let the straps fall down her arms. She looked in the mirror to see her firm 36C breast nestled on her chest. Her dark brown areolas surrounded her small erect nipples.

She bent over and turned the water off. Then took off her panties, before stepping into the warm water. She leaned back and slowly pressed her back against the cold porcelain of the tub. She ran her soft hands down her stomach to just above her pussy. She felt stubble, and reached for her shaving cream and razor. As she applied the cream, she chuckled as she wondered why she kept herself so well groomed. It had been almost year since she had been out with a guy and much longer since she had sex, but she continued until the stubble was gone, then laid her head back and closed her eyes.

When she woke up, she jumped out of the tub and grabbed a towel. She had fallen asleep and was late for work. She wrapped the towel around her body and grabbed her phone to call in. The voice on the other end was not a pleasant one. It was her boss, and she informed Ashley that she no longer had a job there and she could pick up her check the next day. Ashley dropped her phone and sat on the floor and began to cry uncontrollably. She had no idea what she was going to do. If she didn’t find something fast, she was going to be homeless. She thought about calling her parents, but refused. They didn’t have the money to help her, and she was not going to move back in with them. She had to figure something out.

For the first time in months, Ashley got a full night’s sleep. It had been hard to get her troubles off her mind, but the half bottle of vodka in her cabinet helped. She got up and made it to her first class on time, and after school was over she set out to find a job. She bought a newspaper and went to the classifieds, and began to visit the businesses in her area needing help. Unfortunately, the jobs she chose to pursue, were looking for fulltime employees and could not accommodate her class schedule. Then she saw and ad for a custodial job at a massage parlor on the other side of town.

Ashley had heard of the parlor. It was known for shady massages, and it catered to wealthy men who came into town for conferences, and the local college guys looking to get off. It turned her stomach to think about the stuff that went on inside the place. She had second thoughts as she stood at the bus stop, but when the bus stopped in front of her, she stepped on and took a seat. She convinced herself if she was lucky enough to get the job, that she would be just the janitor. She would not be doing anything immoral, and would only be cleaning the parlor, which is nothing short of what she did already with her cleaning side jobs. By the time the bus stopped, she was feeling better about her decision and got off and walked across the street to the parlor.

When she walked in the smell of coconut oil filled her senses. In the waiting area were several men wearing business suits being catered to by the hostess. The hostess was a pretty woman who looked to be in her late twenties. She was wearing a black bikini top that barely concealed her big bouncy breast, and a matching silk wrap around her waist. Ashley approached the counter and waited for her to return. Ashley explained she was there for the job and the hostess handed her and application.

Ashley found a seat and sat down and began filling it out. While sitting there, many men came in, and many left. Ashley noticed that every man that left, left with a smile on their faces and it made her sick to her stomach thinking of the reason for the smiles. When she was done, she handed the application to the hostess and turned to leave. Before she reached the door, the hostess, called her back and gave her the job. She asked Ashley about her schedule, and told her they would accommodate her in any way they could. She was to come in immediately after school, and begin cleaning the rooms as they became available. When she had cleaned the eight rooms, she could leave. Ashely agreed to return the next day to begin. On the way back home she wished she had not drank all the vodka the night before, because she wanted to celebrate.

The next day she arrived to work. She was taken to the back and given instructions. Jessica, the hostess and owner handed her a gift bag and told her to go into the bathroom and change. When Ashley got into the bathroom, she opened the bag and pulled out a bikini with a matching wrap. This had not been in the discussion, but decided to put it on. She needed the money and was in no position to argue. When the outfit was on, she exited the bathroom and was given her assignments. As each room became available, she went in, sanitized the beds, swept and mopped the floors, and restocked the oils, towels and other supplies. Each room took her bout 20 minutes to clean. It was shortly after 6pm when she untied her bikini and put her clothes back on. When she started to leave, Jessica handed her an envelope and she left.

While on the bus headed home, she opened the envelope. Inside was a note and three 100 dollar bills. In the note, Jessica explained that her pay would be $200 a day, and the extra $100 was for her to buy her a couple of bikini outfits to wear. Ashley began to cry, never did she think that the job would pay so well. She got off at the next stop and went to a department store and purchased three bikinis with matching wraps, and a nice dinner. While she was eating she evaluated her finances. Even at $600 a week, it was going to take months to get her out of the hole she was in, and unfortunately she didn’t have that kind of time. The money she had would buy her some time in her apartment, but she had utilities and everything else too. Her happiness soon left her, and she returned to her depression.

The next day she went to work and began her tasks. When she exited one of the rooms, she bumped into a customer. She apologized repeatedly but the man just smiled at her. The girl that was leading the man to her room, frowned and scolded her for being so clumsy, but the man rebuked the young lady, saying that accidents happen. The man helped Ashley pick up her supplies. Ashley could feel his eyes looking at her breast, and she extended her stay in her bent over position because she liked the attention he was giving her.

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When they had put everything back onto her cart, she thanked him, and they went their own ways. Ashley looked back over her shoulder as they walked away from each other. The man was handsome, and she wondered what a guy like him would need a place like this for.

The last room of the day to clean was the one the man had entered. Ashley waited in the adjoining room. She could not help but be curious. She listened closely, and could hear soft moans coming from the other room. She wondered what the girl was doing. Was she jacking him off? Having sex? Blow job? The dirty thoughts she was having made Ashley uneasy. Then she realized her uneasiness didn’t come from what was going on in the next room, her feeling was jealousy, because she was not the one doing it. The man had made an impression on her, and she didn’t know why. He was handsome, well-mannered and well dressed, but so was half the guys that came into the parlor. What about him turned her on? She tried to shake the thoughts from her head, but it was no use.

She heard the door open and shut. So she started making her way to the room. She stood at the door, and knocked, and there was no answer. She went in and did her job. While she was working she paid close attention to the areas she cleaned. There was no sign of semen which was usually left by the working girls when they knew she was coming in to clean. There was no sign of anything out of the way. When she was done she walked back to the front, and was surprised to see the man still there. She changed clothes, and started to leave. When she walked past him he was talking to Jessica. When she neared them, Jessica asked her to stop.

Jessica told her that Mr. Thomas had requested that she accompany him to a dinner party later. Ashley was stunned. Was he asking Jessica permission to ask her out, or was the cover up for an escort service? Was the first thing that popped in her mind. Jessica explained to her that Mr. Thomas was a big contributor to the college and needed a date. She told her that he would pay for everything, plus buy her the proper attire to wear. Ashley had mixed emotions, but agreed. She didn’t have anything planned anyway, plus she owed him for not causing a scene earlier.

The evening was so much fun. Ashley felt like Cinderella. She was wore a dress that she would never be able to afford and Mr. Thomas, or James as he instructed her to call him, was such a gentleman. They ate food she had never heard of, danced, and talked like they were a real couple. Never once did James treat her like she was hired help. He treated her like a lady, but all through the night, she could not figure out why he had asked for her, and why he had to hire someone to go out with him.

When the party was over, they got into the back seat of his car, and it drove away. Without being asked, Ashley told the driver her address, and sat back. She exclaimed to James that the night had been like a fairy tale for her, and he softly replied it didn’t have to end. Ashley was not dumb, she knew what he meant and the comment cut her like knife. James could see her displeasure, and quickly told her his thoughts.

He told her that he was in town about four weeks in a year, and if she would agree to be at his beck and call, he would pay her a good wage to be his exclusive companion while there. He explained his terms. There would be a set fee she would be paid, then extra on the times he was in town and needed her company. There would be an added bonus if she decided be his around the clock companion during his stay. As he talked, Ashley took it all in. He was asking her to be his mistress. She would be his whore and servant. While he talked he reached into his pocket and gave her $1000 and told her that was for her services so far, and if she would accompany him to his hotel, she could double it by morning.

Ashley looked at money. The stack of unpaid bills that lay on her table flashed in her mind. James was a gentleman, she found him attractive and enjoyed the time they had had. She slipped the money into her purse, and smiled innocently and nodded her approval. In no time, they were pulling into his hotel. The driver opened the door of the car, and they walked in hand in hand. While in the elevator, James asked her to hand him her panties. She looked at him strangely, but lifted her dress, and slipped the satin thong down her legs, and off her feet. With a smile, she laid them in his hand. He instantly pulled the panties to his nose and inhaled and gave an approving smile.

The elevator opened up into the penthouse of the hotel. They stepped out, and the door closed. The dinging of the bell sent chills down Ashley’s spine because she was now alone with her new employer. She watched as he walked to the bar and poured himself a drink. He took a big gulp and turned and sat on the sofa and motioned for her to come to him. As she neared, he told her to stop, and to take off her dress. She reached behind her and unzipped the back. She knew when the dress fell, she would be naked except for her expensive heels. She pulled her arm from the sleeve, and the dress fell to her feet. Still moving her panties under his nose he complimented her on how beautiful she was. He instructed her to come kneel in front of him. Without hesitation, she moved to his feet.

James told her to open her mouth. When she complied, he stuffed her panties inside. The thought that she had gotten herself into a place she didn’t want to be crossed Ashley’s mind, but then he touched her. With his index finger, he traced her jaw line, and down her neck. He gently cupped her firm breast, and had his thumbs brush her erect nipples simultaneously. His finger traced down her stomach, and circled her tiny belly button. She shivered with the anticipation of him touching her leaking pussy, and was disappointed when his hand moved up to her arm.

He raised her onto her feet and laid her across his knee. She braced herself for a spanking that never come. Yet, his soft hand moved across her plump ass, and down the back of her leg. Then his hand maneuvered to the other legs and worked up. The side of his index finger grazed her outer lips as it journeyed up her ass, and back. James brought his finger to his lips, and sucked them clean, and instructed her to go to the bed. Ashley moved to the bed and started unhooking her shoes, but James told her to stop. With her panties still in her mouth, she lay back and looked up at the ceiling.

She was startled when she felt her legs being pulled apart, and when she looked, James was naked kneeling between them. He rubbed her clit with his thumb, while stroked his hardening cock with the other. His cock was nothing...

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Written by alliet14
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