The Adventures Of An Escort Pt 01

Part one

Alison's life was a complete mess. She had lost her job, then her apartment and even her car had been repossessed as her debts mounted.

Her good friend Julia had offered her sanctuary in her plush penthouse apartment. That was so typical of her. Even though they had drifted apart over the years, they were still best friends when it counted. It was difficult for Alison, though, as living with Julia highlighted how she had succeeded in life, and Alison had not. The two ladies had met at school and even begun working in a telesales team at the same company. A decade later, Alison appeared to have enough money to enjoy life to the fullest, and Alison had no idea how to get out of the mess she was in.

"Men!" Alison said out loud one evening when they were sitting in Julia's lounge drinking some wine.

"What?" Replied Julia.

Alison then announced with a serious face, to Julia's amusement, that she was giving up men. For good! Alison had gone through a succession of men all of them were either crooks or losers or both. When she thought about it, a lot of her financial problems stemmed from that.

"How many times have you said that?" Julia replied, and they both laughed.

"If you can be celibate, then so can I," retorted Alison.

"What makes you think I am celibate?" Julia said quietly.

Alison frowned sure, they had drifted apart over the years, but they were still in touch. She had never heard Julia mention a partner, a boyfriend or even a one-night stand. When she made that point to Julia, she looked away from Alison awkwardly.

"My sex life is complicated," she said and tried to change the subject, but of course, Alison was not going to let that go and fueled by the wine, she tried to probe further. Now she was thinking hard about Julia, an even more significant question popped into Alison's head.

"Come to think of it, what is it you do, Julia?" Alison asked. "I don't think you have ever properly said. You are always jetting off to a wonderful destination or special event. And you have all this." She waved her arms to indicate the apartment.

"Do you have a sugar daddy?" She added with an amused, conspiratable tone.

"Not exactly!" Julia replied, making Alison choke on the sip of wine she had just taken.

Julia then rose, walked across the room and slowly poured herself another glass of wine. She closed her eyes when, from behind her, Alison asked the inevitable question. What does "not exactly" actually mean? She turned back to face Alison, fixed a smile on her face and, taking a deep breath, took the plunge.

"If I tell you I want your word, you won't judge me, and whatever you think, it stays a secret between you and me. I have never told anyone about this." She said firmly.

As Alison agreed to that, Julia walked back to the couch and sat down next to her. Julia's expression was very serious, and there was suddenly tension between the two friends. Julia took another deep breath before finally speaking.

"I work for an exclusive escort agency," Julia confessed, her voice barely above a whisper. "I am a high-end escort."

Alison's eyes widened as she tried to process this revelation. Her friend, who she thought she knew well, was leading a double life as an escort. It explained the luxurious lifestyle, the extravagant trips, and the way Julia did not ever talk about herself.

"It pays for all this, and I live a great and happy life. Julia added defensively.

Alison was speechless, but as she was trying to recover from one shock, Julia hit her with a further one.

"You could do it too, Ali," she said, looking directly into her friend's eyes. "It would get you out of your mess and give you the financial freedom you seek."

The silence in the room was deafening as Alison struggled to find the right words to respond.

Naturally, the idea of becoming an escort had never entered her mind. Could she even do it? Sleep with strangers for money? She looked around Julia's luxurious apartment. God, how much she craved having financial security, not to have to worry about money every second of every day. The rewards were obvious. Julia's glamorous lifestyle was wonderful. To Alison's surprise, she felt a tiny seed of temptation sprout in her mind and then slowly grow. Was this a way out of the pit of debt and despair she found herself in? She couldn't live off Julia forever. Then, her original question surfaced in her mind again. Could she even do it? Sleep with strangers for money?

"You think I could it?" She asked quietly.

"You could, Ali," Julia said softly, reaching out to grasp Alison's hand. "It wouldn't be easy, but really, it's all in your head. If you can see it as having a great time with some great people, then you can do it. The rest is just sex, and frankly, you spend a fraction of the time doing that. It offers financial stability and freedom. You have the beauty, strength and resilience to navigate this world if you choose to, and you have me to help guide you. But."

Julia paused.

"I have not planned this conversation. I think my boss would talk to you but he might not. I can talk to him, but only if you want me to."

The idea gnawed at her, tempting her with the promise of escape. Could she do it? Could she set aside her inhibitions and take such a risky path? The thought both terrified and intrigued her.

"What do you have to lose?" Julia suggested gently as she sat there, too afraid of both options to speak.

Julia's words echoed in her mind - "It's just sex, which you spend a fraction of the time doing." Could she detach herself emotionally and see it as a transaction, a job like any other? And what about the potential risks and dangers that come with such a profession?

Alison glanced at Julia, who was watching her intently, waiting for a response. Her friend's offer of guidance and support was comforting, but the uncertainty of the path laid out before her sent a shiver down Alison's spine.

Taking a deep breath, Alison finally spoke.

"I...I guess talking to your boss, if he is happy too, does not harm," she said, her voice barely above a whisper.

Part two

Julia's boss, Zachery Heaven, was indeed happy to talk to Alison and invited her to lunch at an expensive hotel in the centre of town. Alison wasn't sure if she was pleased or not. Had he turned her down, it would have made the whole thing so much easier. Julia smiled at her friend as she watched her process the news and then tried to pick her moment to add some further information.

"You'll be eating in one of the Penthouse suite's dining areas," Julia said. "The food is incredible, and Zachery is paying, so exploit that. He knows you are only exploring the idea of being an Escort, so the lunch is just a chat. But Ali he is a busy man, and this is a big favour to me. So, if you choose to proceed, he won't pressure you to, but if you do, he will expect you to go through to the bedroom with him. He is going to want to see you can satisfy our very demanding clients and give you a bit of guidance too.

In that vein, I have booked you a medical check. I use this guy all the time. He is great and discrete. Julia handed over a piece of paper.

Alison felt a mix of nerves and excitement as she prepared for her lunch meeting with Zachery. She went through a whirlwind of emotions, from disbelief that she was even considering this path to a determination to take control of her financial future. Julia had always been there for her, and now, offering this opportunity, she felt a sense of gratitude mixed with apprehension.

Of course, the medical check came back fine.

As she entered the luxurious hotel, Alison couldn't help but feel out of place among the opulent surroundings. Zachery was already waiting for her in the Penthouse suite's dining area. He was tall, athletic and very good-looking.

"You look amazing, Alison," he said. She had taken a long time over her outfit. Or rather, she had spent a long time picking one of Julia's dresses from the enormous number she had. A short, plain but elegant dress with heels hopefully hit the right note.

Alison blushed at Zachery's compliment, feeling a rush of nerves as he kissed her on both cheeks.

"Thank you, Zachery," she replied, mustering a smile. "I appreciate you taking the time to meet with me."

Zachery motioned for her to take a seat, and he ordered them some champagne whilst she looked at the menu. Once they had ordered, Zachery came straight to the point.

"I guess it's been a tough time for you," he said gently, "your financial struggles, Julia's revelation, and now here you are facing me. A whirlwind of doubts and fears, I imagine."

Alison felt some relief as she realised that Zachery seemed to understand the conflict she was facing. His words relaxed her a little.

"So you must have questions. Fire away," he said just as the starter arrived.

Thank you, Zachery," she began, more playing for time than anything. "I do have some questions. I want to know more about the expectations you have for me as an escort. What exactly would be required of me in these encounters with clients?"

"I think the best way to describe it is to put it the way our longest-serving client puts it," Zachery said. "He always says Zachery, my boy, I want a lady on my arm at the Opera and a slut when I take her back to the bedroom. Zachery did it in a Southern American accent, which, despite the enormity of the answer, made Alison smile.

Alison's smile wavered as the weight of Zachery's words settled in her mind. Of course, she had known that being an escort was manly about sex, but hearing it so bluntly shook her. She took a deep breath.

"I see," she said carefully. "And what kind of support or protection does the agency offer? Will there be any boundaries or guidelines in place to ensure my safety and comfort?"

Zachery leaned back in his chair, regarding Alison thoughtfully before replying.

"Alison, it would be wrong of me to say that your safety is guaranteed, but in ten years of operating, we have had no problems. We start you with easier assignments. Understanding and delivering the client's wishes is paramount. They expect the time of their lives. You can refuse to see a client again but not a new one. Only once in ten years has a girl refused to see a repeat customer. Some clients are shady, and some are not. We get all sorts. Some want threesomes, anal, DP, anything might be requested. So you need to be prepared for that."

But remember, building up a network of regular clients is the secret. They are comfortable with you, and you with them."

Alison nodded, her thoughts swirling with all that had been discussed. The idea of becoming an escort still felt very strange. Yet the prospect of financial stability and independence was hard to resist.

"And the money," she asked, "how much could I potentially make?"

The potential income blew Alison's mind. She would be out of her debts in no time. The agency even had an accountant who took care of her income and tips, paid her taxes and helped with any current debts, too. A lot of girls came to the agency with money problems, which made Alison feel a bit better.

This just made Alison even more conflicted just when the sensible side of her brain was winning, and she edging towards saying no, her wilder side started to fantasise about the money. The promise of financial freedom was so enticing, but she had so much apprehension.

"And what about personal relationships?" Alison inquired cautiously. "Would it be difficult to maintain romantic relationships outside of this line of work?"

"Unless you date another escort, normally extremely hard." Zachery smiled as the main course replaced the starter. "I thought you told Julia you were giving up men," he teased.

"Okay, I have one more question," Alison said, too focused to rise to the tease as she tried to understand fully. "What happens if I decide I don't want to continue as an escort after trying it out?"

Zachery looked at her, his eyes softening for a moment.

"Assuming you pass the bedroom test," he said. "We both agree to a three-month trial during which either side can walk away. After three months, we talk again, and we either part as friends or you sign on for three years."

"Zachery," she started hesitantly, "You know I have never been involved in something like this before. How can I be sure that I will be able to meet your expectations?"

Zachery took a sip of his wine before responding.

"Always remember we have a lot of clients that love nerves and the sense that their Escort is new to the game. Every man loves a virgin, right? Those are the kind of clients we start you with." Zachery looked at his watch. "And that's why you and I go to bed together."

Alison's eyes widened at his bluntness, but she couldn't deny the logic in his words. She was new to the world of escorts, and there was no denying that some clients would find that appealing. It was decision time, should she, could she let Zachery take her through to the bedroom and the real test of whether she could be an escort?"

She involuntarily looked across the room to the bedroom door, and her mind raced as to what she should do.

Part three

Zachery held Alison's hand as he walked her through to the bedroom. She was conscious of every step, aware of how her hands were shaking and how heavy her legs felt as the door drew closer. Her heart was racing. Zachery pulled her to him the moment they were inside and kissed her. Zachery's touch sent a mix of nerves and excitement coursing through Alison's body, yet she managed to keep her composure. She tried to kiss him back, and when his initial short, sharp kisses turned to more intense and passionate ones, she tried to mirror his actions with her mouth.

He released her, gave her a sort of nod and then began to remove his jacket. Alison felt she had passed the first test.

"When did you last have sex?" He asked casually, as though it were an everyday question.

Alison hesitated momentarily, a little taken aback by the sudden question. She looked into Zachery's eyes and took a deep breath before finally speaking.

"It's been a while," she admitted.

He reached out to lift her head and kissed her again, his touch sending shivers down her spine.

"Remember, you're here to please me," he said," but I'll guide you here and there as we go."

She managed to nod in response, trying to prepare for what was to come.

Zachery picked Alison up and then gently laid her on her back on the bed. He began to undo the buttons that were down the front of her dress.

"Just lie back with your hands above your head," he commanded and then, almost as an afterthought, he added. "Maybe tell me how much you want this. Clients like that."

Alison tried to think. Her heart pounded in her chest. It was hard to concentrate, but Alison knew she had to find the right words. It surprised her to realise she didn't want to disappoint Zachery.

"I want you so much," she whispered. "I've been waiting all day for you to fuck me, Zachery. I've thought of nothing else."

Zachery's smile was gratified as he finished unbuttoning her dress. He pulled it open to bare her breasts and then took the right one deep into his mouth. His tongue traced a path across her skin to the other side, and he sucked on that one too.

"You have beautiful breasts," he told her.

Alison held her breath as his lips pressed against her skin, her body was tingling from his touch. She closed her eyes and reached out to run her fingers through his hair.

"That's good. Show me you like it," he whispered. "Actions speak louder than words."

He stood up and peeled her dress off, leaving her in just her panties, but he immediately removed them, too. He pushed her legs back and open as he began to eat her out.

"Now tell me," he whispered. "Tell me how good it feels."

Alison bit her lower lip, unsure whether she could put her feelings into words. But she knew that this was what Zachery wanted, and so she found the courage to speak.

"Ohhhhhh, that feels wonderful, Zachery," she whispered. "You are so good at that."

Zachery's smile grew wider as he looked up at her from between her legs.

"That is very good," he said, "always tell a client something is new or the best you have had they love that. Even if they don't believe it." Then he returned his focus to eating her pussy. His tongue was so skilled, and he added a light massage of her right breast to the already overwhelming sensations. Alison was lost in a sea of wonderous sensations. She was Zachery's plaything, and she was beginning to feel surprisingly comfortable. Although concentration was hard, he was already skillfully bringing her to a rapid orgasm.

As the waves of pleasure washed over her, Alison could hardly breathe. Her body trembled and shuddered under Zachery's expert touch. She cried out his name, her voice a mixture of ecstasy and relief. For a moment, it was all too much, but Zachery seemed to either expect or realise that.

Alison felt herself pulled into a hug as she was held tightly. Zachery gently told her it was okay.

"It's okay, Alison, relax and enjoy it," he said gently. "It's been quite a day, huh?"

Alison clung to him, her body still trembling from the intense pleasure.

"Thank you," she whispered, her voice barely more than a whisper. "That was...amazing. Are all clients as good as you?"

"Some," he said with a smile and kissed her forehead and stroked her hair, his smile never faltering. He let her lay there for a little while, and then he gently said.

"It's your turn." He said. "If you want to continue?"

"Was that another test past?" She thought.

Alison took a deep breath, her heart still pounding. She nodded. Ready? No, wanting to give Zachery the same pleasure he'd given her. She knelt on the floor and reached for the button on Zachery's pants, her fingers trembling slightly with nervous excitement.

His erection sprung free, standing tall and proud before her, the tip glistening with pre-cum. He skillfully shed his trousers and pants.

Alison swallowed hard. He was frigging huge. Her fingers explored his cock, and for a moment, it held all of her focus. She was fascinated by its size and the way its hardness and length felt in her hand. What would it be like to have Zachery inside her, Alison thought.

"Look at me," Zachery commanded, breaking into her thoughts and reminding her this was about him, not her.

Alison met his gaze, making her eyes go soft and honeyed, trying to reveal her vulnerability and eagerness. He saw uncertainty mixed with some anticipation, but that only served to excite him more. He had already decided this one was special.

"That's a good girl," he said, his voice low and full of promise. His hand came down onto the top of her head, and Alison obediently opened her mouth wide and let his dick slip between her lips. He watched her blow him as he removed his shirt, and then his hand returned to her head, gently urging her to take more of him down her throat.

Alison's eyes widened slightly as the head of his cock slipped further down her throat, and she felt his warmth and hardness fill her mouth. She tried to relax her throat, letting him slide even deeper into her. Alison had been told before that she was good at blow jobs, and she wanted to demonstrate this to Zachery. His dick felt so good in her mouth.

Zachery continued to guide her, keeping his hand on the back of her head, slowing her movements so she took her time. He loved the warm, wet feeling of her mouth surrounding his cock. He could feel her tongue flicking against him and the sucking of her lips as she moved up and down.

"That's excellent," he whispered. "Good girl. Show me how much you want it."

Alison delighted at the praise, started to move faster, moving her head back and forth and running her lips along his shaft. She felt herself growing in confidence. The feeling of him hitting the back of her throat was so thrilling. Alison's pussy was already so wet. Zachery tightened his grip on her hair, watching with a mix of lust and amazement as Alison worked him expertly with her mouth.