It was raining outside as Ashley examined herself in the mirror, giddy with excitement. The sound of the rain and roar of the thunder had always soothed her. She was 21-years-old with long natural red hair that fell half way down her back. She had piercing blue eyes and light freckles over her nose. She didn’t think anyone would mistake her for a super model as she only stood 5 feet 4 inches tall, but she liked what she saw, and knew she could turn some heads. The extra time she’d been spending training to finally run that marathon was paying off in more ways than one. Her stomach was flat and firm as she ran her hand over it and up over her full B-cup breasts, adjusting them under the small black dress that she wore.
She turned to check out her backside. The dress was a low dipping V-cut in the back and she loved how it hugged and showed off her ass.
She and Mark were about to celebrate their first year anniversary and it seemed that he had gone all out in making this a special day. He was 40-years-old and this was his second marriage. Her parents had of course objected to their age difference and the fact that they’d only been dating for 6 months before their marriage. But it had been a whirlwind romance and he had swept her off her feet.
She had awoken to an empty house that morning and a series of notes had led her to the spa and lunch, a soothing massage, then off to the salon to get her hair done and back home where the dress and jewellery were waiting for her along with another note saying that a car would pick her up at seven.
For once in her life, she promised herself that she would be ready on time and when the knock came at the door, she was. She was escorted into the backseat of a black Lexus and driven into town. She had a smile on her face the whole time, her heart thumping in anticipation as she wondered what Mark had in store for her tonight.
Her eyes grew wide as they pulled up to the Waldorf Astoria and she began adding up the cost of all of the days expenses and knew that they really couldn’t afford it. She had assumed they would be dining first but the driver gave her a hotel key card and room number and told her that she was expected immediately.
Ashley was buzzing as she walked through the hotel lobby and took in the grandeur of the place. Worries about money evaporated as she decided that this was a special day and they deserved to celebrate it. She would enjoy it and wondered what other surprises Mark had in store.
When she got to the room, she slid the key card in and heard the click of the lock and opened the door. She sauntered in, thinking she would show Mark a little appreciation but she stopped dead in her tracks when she saw a strange man standing in the room.
He was an older man and was in his fifties or sixties but kept himself in very good shape. Meticulous would be the word best used to describe his appearance and he spoke in a slight British accent. “Good evening Miss Walker, my name is Mr Avery. Before I explain the nights activities, please read this note from your husband.”
She unfolded the note he handed her and saw Mark’s familiar hand writing. The note read:
Ash,
I’m so sorry, I’ve messed up bad. We are in a lot of trouble if you don’t do what Mr Avery asks you to. I wanted tonight to be special and you deserve so much better than me.
Love,
Mark
Ashley read the note over a number of times as she tried to make sense of it. It had to be a joke, some kind of mistake or game Mark was playing. When she looked up, Mr Avery was standing perfectly still with his unwavering eyes on her and he spoke again.
“There must be so many thoughts running through your head. First, let me tell you that your husband is a degenerate piece of shit.” Ashley took a double take at the contrast of this man’s prim and proper speech and the words he spoke, never mind the things he said about Mark!
“He has a gambling problem, and he owes my employer an incredibly large sum of money. Your house, your cars, your bank accounts, you could cash it all in and it still wouldn’t pay half of his debt. Now you see, my employer is the type of man who believes examples must be set when someone can’t pay the money they owe him. Examples that usually land someone in the hospital. Do you understand what I’m saying?”
Ashley could only nod her head, but she didn’t really understand what he was saying. She had seen enough mobster movies that she knew what he was getting at, but this didn’t sound like Mark at all. She knew he bet some money on the games every weekend, but not crazy amounts of money like this guy was talking about.
“Myself, your husband, and my employer had a sit down to talk about what to do to rectify this situation. And the only viable solution we came to, was you. You see my employer not only engages in gambling activities, but he dabbles in prostitution as well. Based on the pictures we were shown, we thought you’d do quite well with our high end girls.”
Ashley thought she would play along for a bit. There was a part of her that still believed that this was an elaborate setup for their anniversary, but there was a pit in her stomach that told her that this might all be very real. She tried to hold back the trembling in her voice as she replied. “You want me to prostitute myself? What if I say no? What if I run out of this room and tell everyone downstairs what you want me to do?”
Mr Avery blinked a couple of times before giving her his chilling answer. “I suppose your husband might have an unfortunate accident that he would likely not survive. And if he doesn’t have life insurance to pay us, we would go after your family and you until we get our money.”
Ashley didn’t know what they had for life insurance as Mark took care of that stuff. Could she let them hurt him? Her parents? A single tear rolled down her face as she looked back at Mark’s note and hand writing that asked her to do whatever this man said. She forced a swallow as she looked back up at the man, “What do I have to do?”
Mr Avery beamed. “First, before I will place you with a paying customer, I need to know that you can go through with this so I need you to suck my cock. And make it good, we have a standard our girls must uphold. Mark said you were an amazing fuck that loved to suck.”
Ashley’s eyes narrowed as she heard his words. Under almost any other circumstance, she would laugh at the rhyme he said with his stupid accent, but not tonight. She couldn’t believe the position Mark had put her in. She looked down at his note, at his careful hand writing, and she hated him for it. Maybe her parents had been right about him. The thought of what might happen to her parents if she didn’t do as they asked which caused more tears to roll down her face. She kicked off the heels she was wearing and slowly walked the three paces that separated her from this man, this monster and kneeled down in front of him.
She looked up and saw his stupid grinning face and wished she hadn’t looked. That sight would haunt her for the rest of her life. With trembling hands she reached up and undid his belt and his pants and pulled them down. His cock was semi hard and she began to stroke it as she pushed her face to it and inhaled his musky scent. Then she took it into her mouth.
Ashley had only been with two previous boyfriends before Mark came along, but she wasn’t a prude when it came to sex. In fact she loved it, and Mark had opened her eyes to so many things and experiences. But those words rang in her head ‘an amazing fuck that loves to suck’. Well if that was what he really thought of her, if he was really willing to give her away to strange men, then fuck him, she would let herself enjoy this.
She let her tongue curl and caress the head of his now hard cock as she expertly moved her mouth back and forth on it. Her hands slowly caressed his balls, massaging them and running up the other side of the sack. She wasn’t in a hurry and she didn’t suck to get him off as fast as she could, she wanted to make it an experience. Her mouth increased the tension as she sucked him with her tongue never stopping its lapping motion as it caressed and slid over every millimetre of him. Her hands rubbing and massaging his balls. She slowly built every action together like it was a symphony. The pace of it all got faster and faster. She could feel him growing harder and harder with the salty taste of his pre-cum dripping into her mouth and she knew that she hit the crescendo when she felt his balls and scrotum tighten under her grip. She readied herself as he released himself in her mouth and barely heard his screams of ecstasy as she lost herself in the moment. And even after he came she didn’t stop. She continued to suck and play with his cock as she slowed the pace the same way she had ramped it up.
In fact, Mr Avery had to pull his cock out of her mouth as she wouldn’t release it on her own.
She turned to check out her backside. The dress was a low dipping V-cut in the back and she loved how it hugged and showed off her ass.
She and Mark were about to celebrate their first year anniversary and it seemed that he had gone all out in making this a special day. He was 40-years-old and this was his second marriage. Her parents had of course objected to their age difference and the fact that they’d only been dating for 6 months before their marriage. But it had been a whirlwind romance and he had swept her off her feet.
She had awoken to an empty house that morning and a series of notes had led her to the spa and lunch, a soothing massage, then off to the salon to get her hair done and back home where the dress and jewellery were waiting for her along with another note saying that a car would pick her up at seven.
For once in her life, she promised herself that she would be ready on time and when the knock came at the door, she was. She was escorted into the backseat of a black Lexus and driven into town. She had a smile on her face the whole time, her heart thumping in anticipation as she wondered what Mark had in store for her tonight.
Her eyes grew wide as they pulled up to the Waldorf Astoria and she began adding up the cost of all of the days expenses and knew that they really couldn’t afford it. She had assumed they would be dining first but the driver gave her a hotel key card and room number and told her that she was expected immediately.
Ashley was buzzing as she walked through the hotel lobby and took in the grandeur of the place. Worries about money evaporated as she decided that this was a special day and they deserved to celebrate it. She would enjoy it and wondered what other surprises Mark had in store.
When she got to the room, she slid the key card in and heard the click of the lock and opened the door. She sauntered in, thinking she would show Mark a little appreciation but she stopped dead in her tracks when she saw a strange man standing in the room.
He was an older man and was in his fifties or sixties but kept himself in very good shape. Meticulous would be the word best used to describe his appearance and he spoke in a slight British accent. “Good evening Miss Walker, my name is Mr Avery. Before I explain the nights activities, please read this note from your husband.”
She unfolded the note he handed her and saw Mark’s familiar hand writing. The note read:
Ash,
I’m so sorry, I’ve messed up bad. We are in a lot of trouble if you don’t do what Mr Avery asks you to. I wanted tonight to be special and you deserve so much better than me.
Love,
Mark
Ashley read the note over a number of times as she tried to make sense of it. It had to be a joke, some kind of mistake or game Mark was playing. When she looked up, Mr Avery was standing perfectly still with his unwavering eyes on her and he spoke again.
“There must be so many thoughts running through your head. First, let me tell you that your husband is a degenerate piece of shit.” Ashley took a double take at the contrast of this man’s prim and proper speech and the words he spoke, never mind the things he said about Mark!
“He has a gambling problem, and he owes my employer an incredibly large sum of money. Your house, your cars, your bank accounts, you could cash it all in and it still wouldn’t pay half of his debt. Now you see, my employer is the type of man who believes examples must be set when someone can’t pay the money they owe him. Examples that usually land someone in the hospital. Do you understand what I’m saying?”
Ashley could only nod her head, but she didn’t really understand what he was saying. She had seen enough mobster movies that she knew what he was getting at, but this didn’t sound like Mark at all. She knew he bet some money on the games every weekend, but not crazy amounts of money like this guy was talking about.
“Myself, your husband, and my employer had a sit down to talk about what to do to rectify this situation. And the only viable solution we came to, was you. You see my employer not only engages in gambling activities, but he dabbles in prostitution as well. Based on the pictures we were shown, we thought you’d do quite well with our high end girls.”
Ashley thought she would play along for a bit. There was a part of her that still believed that this was an elaborate setup for their anniversary, but there was a pit in her stomach that told her that this might all be very real. She tried to hold back the trembling in her voice as she replied. “You want me to prostitute myself? What if I say no? What if I run out of this room and tell everyone downstairs what you want me to do?”
Mr Avery blinked a couple of times before giving her his chilling answer. “I suppose your husband might have an unfortunate accident that he would likely not survive. And if he doesn’t have life insurance to pay us, we would go after your family and you until we get our money.”
Ashley didn’t know what they had for life insurance as Mark took care of that stuff. Could she let them hurt him? Her parents? A single tear rolled down her face as she looked back at Mark’s note and hand writing that asked her to do whatever this man said. She forced a swallow as she looked back up at the man, “What do I have to do?”
Mr Avery beamed. “First, before I will place you with a paying customer, I need to know that you can go through with this so I need you to suck my cock. And make it good, we have a standard our girls must uphold. Mark said you were an amazing fuck that loved to suck.”
Ashley’s eyes narrowed as she heard his words. Under almost any other circumstance, she would laugh at the rhyme he said with his stupid accent, but not tonight. She couldn’t believe the position Mark had put her in. She looked down at his note, at his careful hand writing, and she hated him for it. Maybe her parents had been right about him. The thought of what might happen to her parents if she didn’t do as they asked which caused more tears to roll down her face. She kicked off the heels she was wearing and slowly walked the three paces that separated her from this man, this monster and kneeled down in front of him.
She looked up and saw his stupid grinning face and wished she hadn’t looked. That sight would haunt her for the rest of her life. With trembling hands she reached up and undid his belt and his pants and pulled them down. His cock was semi hard and she began to stroke it as she pushed her face to it and inhaled his musky scent. Then she took it into her mouth.
Ashley had only been with two previous boyfriends before Mark came along, but she wasn’t a prude when it came to sex. In fact she loved it, and Mark had opened her eyes to so many things and experiences. But those words rang in her head ‘an amazing fuck that loves to suck’. Well if that was what he really thought of her, if he was really willing to give her away to strange men, then fuck him, she would let herself enjoy this.
She let her tongue curl and caress the head of his now hard cock as she expertly moved her mouth back and forth on it. Her hands slowly caressed his balls, massaging them and running up the other side of the sack. She wasn’t in a hurry and she didn’t suck to get him off as fast as she could, she wanted to make it an experience. Her mouth increased the tension as she sucked him with her tongue never stopping its lapping motion as it caressed and slid over every millimetre of him. Her hands rubbing and massaging his balls. She slowly built every action together like it was a symphony. The pace of it all got faster and faster. She could feel him growing harder and harder with the salty taste of his pre-cum dripping into her mouth and she knew that she hit the crescendo when she felt his balls and scrotum tighten under her grip. She readied herself as he released himself in her mouth and barely heard his screams of ecstasy as she lost herself in the moment. And even after he came she didn’t stop. She continued to suck and play with his cock as she slowed the pace the same way she had ramped it up.
In fact, Mr Avery had to pull his cock out of her mouth as she wouldn’t release it on her own.
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And when he did she looked up at him with a smile and made a show of swallowing even though she had already swallowed all of his cum then ran her tongue over her lips and smacked them.
Mr Avery cleared his throat and was clearly affected by the blowjob she had just given him. When he spoke his accent was much stronger than it had been earlier. “Right. I do believe you will do.” He began to dress and the sound of the zipper of his pants was quite audible as she was still on her knees in front of him. “Your appointment for tonight will be along shortly. Your name will be Sara tonight. If all goes well, you can expect two to three rendezvous a week. Instructions of where and when will be delivered to you.”
As he walked to the door to leave, a thought jumped into her mind as she realized what was coming. “Wait! I don’t have any condoms on me. I was expecting my husband tonight. Will whoever is coming tonight be bringing some?” she asked hesitantly.
Mr Avery stopped but didn’t turn around. “Our clients are carefully screened and pay large sums of money for our special service and discretion. This is no side street sleazy internet agency. Some men prefer a more natural feeling and if they don’t want to use them, they won’t bring them.” With that he continued out of the room and shut the door behind him.
Ashley suddenly found herself alone in the room with only her thoughts which were a roller coaster of emotions. There was hate that Mark would do this to her, fear of a strange man coming to have sex with her, disgust at what she had just done with Mr Avery, as well as both shame and desire that there was a part of her that was actually excited for what was to come. It kind of turned her on, gave her a sense of power, that a man would be willing to pay money to be with her.
She got up off her knees and went to the washroom to clean herself up and get ready for her ‘date’. She began to pace the room as a million thoughts filled her mind of who would be coming and what he would want to do. Time seemed to drag on forever, that was until she heard the knock on the door. It seemed that the moment had come all too soon.
Her heart was pounding as she looked through the peephole and saw an older, well dressed man on the other side. She opened the door to let him in and there was an awkward silence as they looked each other over.
She would guess that he was in his forties. He was balding but he kept his hair cut short and it suited him. She thought he might have a bit of a belly but he wasn’t horribly over weight. He had a confidence about him that she found quite attractive. His suit was well tailored and he sported an expensive rolex watch. She would guess he was used to being in charge in whatever occupation he held.
They hugged and kissed, and she led him inside the room. It felt a little fabricated to her, but he seemed to enjoy it and even gave her a good feel of her ass when they hugged.
“I’m Sara, welcome to, umm, my room. Can I get you something to drink?” She blushed and felt awkward with the way it all came out. But when he smiled back at her she relaxed a little.
“We have all night to get to know each other Sara but you are even more beautiful than in your pictures they showed me. I want to watch you undress for me.” He went and sat in a chair and stared at her with unwavering eyes.
This was the moment. Was she going to be able to do this? She took in a big breath and walked over to him turning so her back was facing him and asked him to unzip her dress. When she felt the tug of the clothing as he pulled it out and the zip sound as he pulled the zipper down she wished she had worn more clothing that night.
The dress fell to the floor leaving her in her bra and panties. She began to turn around to face him again but she felt his hand on her ass to stop her. She tried not to jump when he touched her. “No, undress facing away from me” he ordered her.
She reached back and undid the clasp of her bra and let it fall to the floor. She was actually glad she was facing away from him as he wouldn’t see her breasts right away. Somehow that comforted her. She slipped her fingers into the waistband of her panties and slid them down her legs and kicked them off. There, she had done it. She was now naked with a strange man. It was exhilarating and scary at the same time and she had goose bumps over her entire body.
“Good. Now spread your legs and bend over placing your palms flat on the floor.” His voice was low and quiet but there was an edge there like he was used to giving orders and having them followed.
She mentally counted to three before doing what he asked. As she bent forward, she felt her ass cheeks naturally spread which exposed her entirely for his viewing pleasure which made her feel very vulnerable. His hands caressed her butt cheeks and slowly made their way in between them. A finger ran the length down her crack, starting above her asshole and over it then down further splitting her pussy lips and pushing into her. She was suddenly embarrassed by how wet she was and that he would know she was enjoying this. “Go lie on the bed on your back with your legs spread.”
She was grateful for being told to get up as the blood had begun rushing to her head. She felt a little light headed as she made her way to the bed and complied with his wishes. He got up from the chair and undressed himself as he followed her. He slid between her legs and pushed his face to her extending his tongue to lick her from the base of her pussy to the top of it.
She moaned and tilted her hips up in an aroused appreciation for his tongue. He began to intimately explore every part of her pussy with his tongue and she revelled in the attention. His tongue swirled and flicked over her engorged clit as he slid a finger inside of her. He began to caress and stroke the inner folds of her pussy. Her body rewarded him with a flood of juices for his efforts. He obviously enjoyed this and was very good at what he did. He didn’t stop until he had her screaming in ecstasy with her whole body shaking beneath him.
He slid up her body and kissed her, letting her taste her own orgasm on his lips. She felt his bare cock knocking and sliding over her pussy and she tilted her hips up to accept him inside of her. So much for the condom. She whimpered when she felt him fill her and their bodies became intertwined, pulsing and moving as one. He began to thrust his hips back and forth faster and faster until they built into a frenzied pace and she felt his...
Mr Avery cleared his throat and was clearly affected by the blowjob she had just given him. When he spoke his accent was much stronger than it had been earlier. “Right. I do believe you will do.” He began to dress and the sound of the zipper of his pants was quite audible as she was still on her knees in front of him. “Your appointment for tonight will be along shortly. Your name will be Sara tonight. If all goes well, you can expect two to three rendezvous a week. Instructions of where and when will be delivered to you.”
As he walked to the door to leave, a thought jumped into her mind as she realized what was coming. “Wait! I don’t have any condoms on me. I was expecting my husband tonight. Will whoever is coming tonight be bringing some?” she asked hesitantly.
Mr Avery stopped but didn’t turn around. “Our clients are carefully screened and pay large sums of money for our special service and discretion. This is no side street sleazy internet agency. Some men prefer a more natural feeling and if they don’t want to use them, they won’t bring them.” With that he continued out of the room and shut the door behind him.
Ashley suddenly found herself alone in the room with only her thoughts which were a roller coaster of emotions. There was hate that Mark would do this to her, fear of a strange man coming to have sex with her, disgust at what she had just done with Mr Avery, as well as both shame and desire that there was a part of her that was actually excited for what was to come. It kind of turned her on, gave her a sense of power, that a man would be willing to pay money to be with her.
She got up off her knees and went to the washroom to clean herself up and get ready for her ‘date’. She began to pace the room as a million thoughts filled her mind of who would be coming and what he would want to do. Time seemed to drag on forever, that was until she heard the knock on the door. It seemed that the moment had come all too soon.
Her heart was pounding as she looked through the peephole and saw an older, well dressed man on the other side. She opened the door to let him in and there was an awkward silence as they looked each other over.
She would guess that he was in his forties. He was balding but he kept his hair cut short and it suited him. She thought he might have a bit of a belly but he wasn’t horribly over weight. He had a confidence about him that she found quite attractive. His suit was well tailored and he sported an expensive rolex watch. She would guess he was used to being in charge in whatever occupation he held.
They hugged and kissed, and she led him inside the room. It felt a little fabricated to her, but he seemed to enjoy it and even gave her a good feel of her ass when they hugged.
“I’m Sara, welcome to, umm, my room. Can I get you something to drink?” She blushed and felt awkward with the way it all came out. But when he smiled back at her she relaxed a little.
“We have all night to get to know each other Sara but you are even more beautiful than in your pictures they showed me. I want to watch you undress for me.” He went and sat in a chair and stared at her with unwavering eyes.
This was the moment. Was she going to be able to do this? She took in a big breath and walked over to him turning so her back was facing him and asked him to unzip her dress. When she felt the tug of the clothing as he pulled it out and the zip sound as he pulled the zipper down she wished she had worn more clothing that night.
The dress fell to the floor leaving her in her bra and panties. She began to turn around to face him again but she felt his hand on her ass to stop her. She tried not to jump when he touched her. “No, undress facing away from me” he ordered her.
She reached back and undid the clasp of her bra and let it fall to the floor. She was actually glad she was facing away from him as he wouldn’t see her breasts right away. Somehow that comforted her. She slipped her fingers into the waistband of her panties and slid them down her legs and kicked them off. There, she had done it. She was now naked with a strange man. It was exhilarating and scary at the same time and she had goose bumps over her entire body.
“Good. Now spread your legs and bend over placing your palms flat on the floor.” His voice was low and quiet but there was an edge there like he was used to giving orders and having them followed.
She mentally counted to three before doing what he asked. As she bent forward, she felt her ass cheeks naturally spread which exposed her entirely for his viewing pleasure which made her feel very vulnerable. His hands caressed her butt cheeks and slowly made their way in between them. A finger ran the length down her crack, starting above her asshole and over it then down further splitting her pussy lips and pushing into her. She was suddenly embarrassed by how wet she was and that he would know she was enjoying this. “Go lie on the bed on your back with your legs spread.”
She was grateful for being told to get up as the blood had begun rushing to her head. She felt a little light headed as she made her way to the bed and complied with his wishes. He got up from the chair and undressed himself as he followed her. He slid between her legs and pushed his face to her extending his tongue to lick her from the base of her pussy to the top of it.
She moaned and tilted her hips up in an aroused appreciation for his tongue. He began to intimately explore every part of her pussy with his tongue and she revelled in the attention. His tongue swirled and flicked over her engorged clit as he slid a finger inside of her. He began to caress and stroke the inner folds of her pussy. Her body rewarded him with a flood of juices for his efforts. He obviously enjoyed this and was very good at what he did. He didn’t stop until he had her screaming in ecstasy with her whole body shaking beneath him.
He slid up her body and kissed her, letting her taste her own orgasm on his lips. She felt his bare cock knocking and sliding over her pussy and she tilted her hips up to accept him inside of her. So much for the condom. She whimpered when she felt him fill her and their bodies became intertwined, pulsing and moving as one. He began to thrust his hips back and forth faster and faster until they built into a frenzied pace and she felt his...
