CHAPTER THREE: OSCAR TAKES A CHANCE

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There were almost 20 years of age difference between them, but Oscar didn't notice it when he was with Cassandra. He'd been seeing her weekly for almost three months now. They had a routine. He booked her for a full day every Friday. They'd gotten to know each other well already because of how much time they spent together.

Friday was Oscar's favourite day. He felt completely at ease in Cassandra's company; something he hadn't felt in years with his wife, if ever. He couldn't remember what the good times with his wife were like anymore. Cassandra's presence in his life melted his past pain away. That's not to say he was healed in every way. But he was healing.

The first time with Cassandra, his cock had stood to attention with no encouragement whatsoever. But the second time, Oscar wasn't so lucky. He tried to reassure Cassandra that it must be his age and that it had nothing to do with her.

When Cassandra laughed, he winced. "I didn't think it was because of me," she said gently, seeing the look of hurt on his face. "It happens to men at any age and it's no big deal," she said. But Oscar went to his doctor and asked for dick pills anyway.

Every Friday, Oscar picked Cassandra up early in the morning at her massage studio. They went for a walk or to a coffee shop depending on the weather and how they were feeling. Then Oscar cooked them a light brunch back at her studio. Oscar loved cooking for her. He stocked her kitchen with everything he needed and showed up with groceries when necessary.

Afterwards, they gave each other massages, talking about their dreams and goals together, saving the happy endings for later. Pillow talk inevitably stretched out after their happy endings. Oscar loved that Cassandra was an intelligent, hardworking woman who did sex work because she wanted to. He also loved to make her come.

Cassandra filled all of his senses when he was with her. He lived to serve her food, conversation, sensual pleasure; whatever she would accept from him – he gave it all to her. His phone was his only distraction when he was with Cassandra. He was running multiple businesses and he had responsibilities. He periodically checked his phone and dealt with work issues as they arose throughout the day but Cassandra never complained.

When he asked her if it bothered her, she smiled. "I get it," she said. "I used to be a lawyer." She, too, checked her phone for messages from her mother or daughter and Oscar politely took a backseat to their importance in her life. He did not expect her to ignore them for the entire day.

During their massages, Cassandra led them into a reciprocal and sensual dance of nurturing touch. Wearing only thong panties, she wrapped herself in his fully nude embrace, whispering about how horny he made her feel when he held her so tight with his hard cock pressing against her thigh.

Meanwhile, his cock had a mind of its own. It constantly reached for the heat of her pussy. Unfortunately, her pussy was off limits. His cock could reach all it wanted. Oscar would not allow it to touch her against her wishes.

Oddly, the knowledge that he could not fuck her somehow made their intimate sessions more intense and fulfilling rather than frustrating as one might expect. Knowing he would not possess her fully, made her all the more desirable. Still, he held onto hope that one day, just for him, she'd change her mind. He did give her a lot of pleasure after all. He often entertained the thought that perhaps one day she would give herself to him in all the ways he longed to take her.

It was crazy how fast he had come to depend on her. His first few encounters with Cassandra, Oscar worried that her behaviour towards him was all an act. She couldn't possibly find him attractive or truly be enjoying his conversation and sensual attentions, could she? If she was acting, then she deserved an academy award because she appeared to be completely genuine.

Cassandra shared personal aspects about her life with him. He knew she had a daughter and mother; both of whom she was extremely close to. He knew about her past life as a lawyer. She was relatively new to being a sex worker compared to the years she spent in the legal profession.

She said it was a relief to spend her days sharing love energy with real people instead of fighting in courtrooms filled with fake people. It was difficult for people to be themselves in that world, she said. Sex work was surprisingly honest, she'd told him. "I don't have to pretend to be someone I'm not anymore."

One day Oscar asked Cassandra, "What do you like about me? We seem to have an amazing connection. I love everything about you. But I wonder, what do you like about me?"

It was a vulnerable question, but Oscar surprisingly felt safe enough to ask it. So far, Cassandra never shied away from vulnerable conversations during their pillow talk. In fact, she was usually the one to initiate them. He felt like it was a safe zone they shared with one another.

"Ohhh, I like a lot about you," she said, looking into his eyes. "You're intelligent, interesting, ambitious, and kind. You're generous, not just with money and gifts, but with your time, cooking skills, and your tongue." She raised her eyebrows and drawled out the last word erotically.

He had shown her how generous he could be with his tongue on more than one occasion. Cassandra certainly seemed to appreciate his tongue. That was for sure.

Oscar decided to believe in her sincerity because she literally never broke character. She was consistently attentive and caring but she also had her own mind. She challenged him playfully and respectfully when she disagreed but she wouldn't agree just to make him happy. Plus, Osar desperately wanted to believe that her behaviour towards him was real.

So, Oscar took her at her word. She liked him. She found him interesting and intelligent and she enjoyed his tongue. Knowing these things made him feel giddy. Between their sessions, he walked on air, smiling at everyone he met. Cassandra made him feel like a sexy man. She was an incredible woman. He was grateful that he'd taken his best friend's advice and hired a sex worker.

Oscar found himself thinking about Cassandra a lot. He knew it would probably never happen, but he liked to imagine what it would be like to wake up with her every morning and cuddle on the couch with her every evening. As the weeks went by, Oscar spent more and more time thinking about what it would be like to be in a romantic relationship with Cassandra.

When they were together, he tried to learn every detail he could about her. He asked her questions about her dreams because he wanted to help her achieve them. He wanted to give her whatever he could. When his focus on her began to resemble an obsession, Oscar realized he was falling in love. The realization was like a thunderbolt.

Suddenly the world looked different. Oscar had something really special to live for now; a possible future with an incredible woman. They were amazing together. He didn't care if she was a sex worker. Perhaps, she would leave sex work. He could provide for her and her family. He'd be happy to do anything for her.

But did Cassandra love him back? She was obviously fond of him. But did she love him? What if she didn't? How could he find out without wrecking what they had. He'd rather have their current relationship than none at all with her. Cassandra had become a huge part of his life.

It got to a point where Oscar wasn't sleeping. He tossed and turned with thoughts of Cassandra swirling in his head. His fear that she did not love him back dwarfed the amazing feelings he'd experienced over the past several weeks with her. He knew that he had to find out where she stood. He wouldn't be able to think straight until he knew if he had a chance.

As the following Friday approached, Oscar's anxiety grew. How would he broach the conversation? He imagined it many times in his head. He would bring it up during their pillow talk. It meant he would feel anxious all day, waiting for the right moment. But he wanted to be looking directly at her when he told her he loved her. He wanted to see her reaction.

Friday morning, Oscar and Cassandra walked along the beach before brunching on a patio that overlooked the ocean. When they returned to Cassandra's condo, Oscar dropped her off at the door and drove away to find parking. That's when he noticed a cop car parked on Cassandra's street.

The lone cop in the car was looking down at something, probably his phone. Oscar assumed he had pulled over to do paperwork or something. Oscar found a parking spot and walked towards Cassandra's building, putting the police officer out of his mind.

Technically, Oscar was breaking the law by paying for intimacy with Cassandra. In Canada, it was illegal to purchase sexual services. But Oscar didn't feel like he was doing anything wrong and no one could prove they weren't friends or lovers. So, it did not even occur to Oscar that the cop was a threat to him.

Absorbed in thought about the conversation he wanted to have with Cassandra, Oscar didn't notice that the police officer was watching him. He didn't see the scowl on the cop's face or hear him mutter under his breath, "Who is Mister Money Banks? This fucking coward." He didn't see the cop shaking his head with disgust as Oscar entered Cassandra's building.

When Cassandra let Oscar into her condo, she looked like she'd been crying. "What's wrong?" he asked, putting his arms around her.

"Oh nothing," she said. "Just dealing with some personal stuff. I don't want to talk about it." That was a first. Usually Cassandra was an open book.

"Is it your daughter or your mom?" Oscar was concerned. He didn't like seeing Cassandra suffer.

"No, they're fine," she replied. "You are so sweet for asking but my family is fine. You don't have to worry about me." Cassandra squeezed him tight as they stood with their arms around each other.

"I can't help it," Oscar replied. "Is it your work? I often worry about your safety." He didn't let his mind go there but he did worry that one of Cassandra's clients would hurt her.

"So far, I've never had any bad experiences at work," Cassandra reassured him. "But since you're asking, I was wondering if I could make you part of my safety plan. You said you live nearby, right?"

"Yes," Oscar said. "I live about a five to ten minute drive from here. What can I do for you?"

"Well, I always hide a phone in my bathroom when I have a first time client. If he becomes violent or aggressive and I can get away from him, I will lock myself in the bathroom and phone you for help. I have a friend that I check in with before, during, and after first-time bookings. But she doesn't live close and there's nothing she could do if something actually happens, aside from calling the police."

"Why don't you want her to call the police?" Oscar asked. "You told me it's not illegal to be a sex worker in Canada."

"That's technically true," Cassandra replied. "But I don't want to heat my condo out. If police know what I'm doing here, they might harass me or worse, arrest my customers. I'd rather just deal with a predator myself. Also, I don't need cops knowing I'm a sex worker."

"Okay, how can I be part of your safety plan? What do you want me to do if this happens?" Oscar asked.

Cassandra unwrapped her body from Oscar's embrace and walked over to a drawer in her kitchen. She opened it and pulled out two keys. Handing him the keys, she said, "I want you to come to my building and scare the guy away."

Before she released the keys into Oscar's hand, she looked into his eyes. "I know this is a lot to ask and it could even be dangerous. I would understand if you are not comfortable doing this for me." But Oscar took the keys and put them in his pocket.

"I'm honoured that you trust me enough to ask," he said. "I'd be happy to deal with any man who dares to hurt you, my love."

The words slipped out. My love. Would Cassandra be repulsed by those words? She didn't seem to notice until she replied. "Thank you, my love." She hugged him again. "Now, let's get you naked, Sexy. I'm massaging you first today."

As Oscar lay facedown on the bed, feeling the weight of Cassandra lying across his back, the length of her body along the length of his body; he marveled at the heat of her pussy emanating into his tailbone. He didn't need to see her body to know exactly where it was. Erotic energy flowed out from Cassandra, especially from between her legs.

When it was his turn to massage her, Oscar showered kisses upon her entire body, teasing her until she arched towards him, begging for tongues, fingers, and orgasms. He made her come again and again, insatiable for her whimpers of ecstasy. This was a boundary she only allowed him to cross. She'd told him that her other clients weren't allowed to go down on her.

As they pleasured one another, Oscar became filled with certainty that Cassandra loved him back. She had not pulled away when he called her "my love." She'd called him "my love" right back. She'd trusted him enough to give him keys to her condo. And look at her now, writhing under the blissful attentions of his hands and mouth. This must be love, Oscar thought.

When it was his turn to orgasm, Oscar found himself unable. Perhaps it was pent up anxiety about the conversation he still wanted to have with Cassandra. Or maybe it was because he had masturbated yesterday. He didn't know. He stopped Cassandra from her sexy attempts to bring him to orgasm.

"I don't think it's going to happen today," he said.

Cassandra smiled. "Do you want to try?" she asked.

"No," he replied. "I'd rather lie here and talk with you. I love our naked time together but you know what? I love the time we spend talking even more. You are one hell of a woman, Cassandra."

Cassandra beamed. "Why thank you," she said, blushing. "You're one hell of a man, Oscar. I truly appreciate you."

Well, she wasn't confessing her undying love but appreciation was a great start, Oscar thought. "I appreciate you too," he said. "In fact, I sort of think I love you, if I'm honest."

Cassandra pulled out of his embrace slightly; just enough to look into his eyes. She had a quizzical expression on her face. "I love you too, Oscar. You are my favourite client. I absolutely love the time we spend together."

There it was. She was setting a boundary. Oscar was "her favourite client." But maybe it was because she feared losing his financial support if they became more than what they were. "I would still support you financially, if we dated," he rushed to reassure her. "You could even quit sex work, if you wanted. I'm very successful, financially. I could support you and your whole family …"

The look on Cassandra's face stopped him. "Oh Oscar," she said, with pain in her eyes. "I hope I haven't led you to believe that I want something more with you. I do love you, but it's a different kind of love than romantic love. I adore you and truly enjoy our time together but I already have a boyfriend, Oscar. In fact, I met him the same day I met you."

Oscar remembered her saying she was single during his first booking. It hadn't occurred to him that her relationship status might have changed since then. He felt disappointed but oddly, he wasn't heartbroken. Cassandra wasn't rejecting him because she didn't find him worthy. She was rejecting him because she already had a boyfriend. At least he could still be her client.

They spent the next several moments reassuring one another that nothing would be different now. Oscar couldn't imagine losing Cassandra over a misunderstanding. Cassandra didn't want their relationship to feel awkward or painful for Oscar. They agreed that they still wanted to be in each other's lives and it was good to have all their cards on the table.

"But why didn't you ask your boyfriend to be part of your safety plan if a client is scaring you?" Oscar asked.

"He doesn't really like my work," Cassandra admitted. "If I tell him that a client is scaring me, he'll use that as more reason for me to quit." Oscar didn't know how to react. He felt a bit ashamed for suggesting that she quit doing sex work for him, as well. He could understand why a guy wouldn't want his girlfriend having intimate experiences with other men.

Still, she shouldn't have to keep secrets from her partner. "I don't know how I feel about a boyfriend you can't talk to when you have a bad day," he said, a little patronizingly, he regretfully admitted to himself. Cassandra must have noticed too, because she pulled away from him, her eyes flashing.

"It doesn't really matter how you feel, Oscar. It's not up to you who I date. I think it's time for you to go. I'm feeling rather tired now." Oscar apologized profusely but he didn't want to make things any worse. He got dressed and left like she asked, beating himself up with every thought that ran through his mind.

How could he have said that? What if she never forgave him? How will he fix it? He was so wrapped in his despair as he left that he didn't notice the cop was still sitting there. He didn't notice the cop watching him walk down the street with a wrinkle between his brows. And he definitely didn't see the cop following him at a distance as he drove home to his empty apartment.

Oscar was oblivious to everything as he drove home in trance, reliving the moment when he'd offended his dear, beautiful Cassandra. It wasn't until he was sitting in his favourite chair, sipping a scotch, that he realized she'd never told him why she was crying. Was it because of her disapproving boyfriend? Oscar knew he had no right to ask. Cassandra had made that loud and clear.

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