CHAPTER FIVE: OSCAR “CHEATS” ON CASSANDRA
This is the fifth chapter in an ongoing erotic romance novel about a client and a sex worker. In this chapter, Oscar sees a new provider behind Cassandra's back and ends up having an odd but amazingly memorable experience.
Table of Contents:
1. Oscar Shares A Secret
2. Cassandra Falls for her Client
3. Oscar Takes a Chance
4. Cassandra Heals the World
5. Oscar “Cheats” on Cassandra
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OSCAR “CHEATS” ON CASSANDRA
The first time he found his car with a flat tire, Oscar assumed it was a random occurrence. The second time, he wondered if he was driving a certain way that was puncturing his tires. The third time, he knew it was intentional. But he had no idea why someone was targeting his vehicle. After a conversation with his building manager, Oscar's parking spot was changed and he no longer had this problem. But it unnerved him nonetheless.
Oscar had never been the target of vandalism or violence before. This passive-aggressive violation felt foreign to him and it made his hair stand on end. Fortunately, he had enough exciting things going on in his life that the repeated offenses against him didn't occupy the majority of his thoughts. He had something else occupying his thoughts because he was going to try something – or someone, to be precise – new.
After Cassandra rejected his attempt to date her, Oscar realized that he was getting too attached to her. He feigned sickness the next week with Cassandra and made a plan to go an Asian massage parlour instead. He was both nervous and excited. The stereotypes he'd come to believe about Asian massage parlours made him nervous but his newfound involvement in the sex industry world with Cassandra made him feel bold. Dressed discreetly, he entered the "spa" with trepidation.
He was greeted at the front desk by a woman who appeared to be around Oscar's age, and spoke broken English. As she took his money, he wondered if she was to be his masseuse. To his relief, a woman who looked to be in her thirties appeared and led him to a room in the back. He would have accepted a massage from the older woman, to avoid insulting her, but he was happy it was this younger, more attractive woman who was serving him. She pointed at the massage table, then to a chair with hooks on the wall beside it. With a brief smile, she left the room.
Taking the hint, Oscar hung his jacket on one of the hooks and disrobed, folding his clothes neatly and placing them on the chair. He climbed onto the massage table, laid facedown, and waited for the younger woman to return. So far, everything seemed professional. Oscar had seen so many movies and heard so many stories that he'd always assumed the Asian massage parlours were sex traffickers. But when he asked Cassandra about it, she said that for the most part, that was a stereotype.
"As I understand it," she said, "The parlours have to jump through hoops to open up and bylaw is checking the ID's of the workers regularly. It doesn't mean they are all legitimate businesses, but I don't think you have to worry too much if you want to check one out." He had reassured her that he only wanted to see her, but she replied, "I don't own you. You can do whatever you want. I'll miss you if you stop coming to see me but you don't owe me anything." She had smiled at him with fondness then, and arched her eyebrow mischievously.
Although Cassandra had essentially given him "permission" to see other providers, Oscar still didn't feel right telling her about it. He would keep it to himself. He hadn't intended to do this but now that he was doing it, he had to admit it was exciting. As he waited for the younger woman to return, Oscar felt himself growing hard in anticipation of feeling this beautiful stranger's hands on him. He was startled when both women returned rather than just the one and they were both completely naked.
As they approached the massage table, the older woman began talking in an authoritative tone of voice. It quickly became clear that Oscar was being used to train the younger woman. The older woman instructed and demonstrated and the younger woman followed her lead. Oscar couldn't understand what they were saying, but their tones unmistakably indicated that the younger woman was new to this line of work.
With brisk and professional detachment, the two women worked over his back, legs, and arms before telling Oscar to turn over. This was when things took a very interesting and unexpected turn. As the older woman showed the younger woman how to handle, stroke, and arouse his cock, Oscar was amazed at how much this entire scenario turned him on. But his amusement turned to shock when the older woman gestured for the younger woman to put a condom on him.
For the next several minutes, Oscar felt like he was in a dream because this could not really be happening. After rolling the condom on, while the older woman chattered away in a language Oscar did not understand, the younger woman began to suck Oscar's cock. It was so erotic, yet so surreal, to have his this beautiful woman's mouth on his cock, while the other woman watched and encouraged her; Oscar almost came with his cock in her mouth. But just before he hit the point of no return, she stopped.
At the older woman's direction, the younger woman climbed onto the table and perched over Oscar. Her small, perky boobs stared down at him and her hair hung in his face, as she positioned herself and then pushed her pussy slowly down onto Oscars throbbing cock. Taking continuous directions from her mentor, she began to rock her hips, bracing herself with her hands on Oscar's chest. The entire absurd and glorious experience had him already on the verge of climax.
As he looked up at her in amazement, struggling to hold back his come, she suddenly smiled at him. That was all it took. Oscar's cock exploded inside her pussy. Well, to be precise, it exploded inside the condom, inside her pussy. But the details didn't matter. It had been a long time since Oscar had come with his cock inside a woman. It felt amazing despite the weirdness, and maybe because of the weirdness, of the situation he found himself in as a training dick.
As Oscar left the massage parlour, he shook his head in wonder at what had just occurred. He was pretty sure that it wasn't how they normally conducted appointments. He was probably pretty lucky that he happened to show up on this particular day at this particular time. Otherwise it might have been someone else providing "the stunt cock." This thought made him laugh out loud.
He realized that this story was too incredible to keep to himself. He had to tell someone, but who? Even though his best friend, Leonard, was the one who encouraged him to book with a sex worker in the first place, he didn't feel right "kissing and telling." It just wasn't Oscar's style. But this was one of the most remarkable things that had ever happened to him.
He realized as he got into his car and drove home that he was going to be honest with Cassandra after all. He knew she would get a kick out of his story. They would laugh together about how life is an ever-unfolding series of surprises. She, of all people, would understand the hilarity of what happened. Oscar knew that Cassandra wouldn't ride his cock but she gave him something that he hadn't gotten at the massage parlour. She gave him tenderness, care, and attention.
As great as it was to feel his cock inside a beautiful woman, Oscar needed care and tenderness more. He needed to feel seen. Cassandra gave that to him. She was a special lady. That didn't mean he wouldn't try another provider in the future. But he would continue to see Cassandra too. She'd become his closest friend, if he was honest with himself.
When he arrived home, Oscar sent Cassandra a quick text to confirm their next Friday together. He wasn't ready to give her up yet. But he was brave enough to see other providers now. He realized he was starting to feel like a man again. All those years feeling unworthy and like a disappointment in the bedroom were beginning to fade away. It wasn't that he was unlovable or undesirable. It was just that he and his wife grew apart. Knowing this marked a turning point in Oscar's healing. Maybe he'd even start dating again.
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I hope you enjoyed this chapter in the Cassandra and Oscar fictional sage that follows two people, a sex worker and a client, through the peaks and valleys of their lives. This chapter is based on a recollection of a story told to me by one of regular clients about his first visit to a massage parlour!
Love Annie xoxo