CHAPTER SEVEN: OSCAR TRIES ONLINE DATING
In this chapter, Oscar goes on a date he found on a dating platform and has a very embarrassing experience. This is a true story of something that happened to someone I know. How do you think Cassandra reacts to his embarrassing story? Read or listen to find out.
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
6. Cassandra Does A Duo
7. Oscar Tries Online Dating
LISTEN TO THIS CHAPTER IN ANNIE’S VOICE
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OSCAR TRIES ONLINE DATING
Cassandra rested her head in the crook of his arm, her naked breasts pressing against his side. Their afternoon massages that they gave each other were all done and now they relaxed with some pillow talk.
"So, tell me what your date was like," she said. Oscar had created an online dating profile and met his first date the previous weekend.
"There's not much to tell," he replied. "I thought we had a great time but when I asked if I could see her again, she said there was no connection." Oscar tried to sound like it was no big deal but he knew he sounded hurt.
"It was your first date," Cassandra said reassuringly. "You can't expect to meet someone to spend your life with right away."
"What about someone to spend the night with?" Oscar replied. His feelings of self-doubt had increased since signing up for online dating. He rarely got a match and when he did, their interest seemed mild at best. The one date he'd gone on had been a disaster. He couldn't help smirking with self-contempt, remembering it.
"Is that what you're looking for? Someone to have sex with? Why don't you hire a full service sex worker, then?" Cassandra was starting to offer advice when she noticed his smirk. "What are you smirking about, Oscar?" She pinched his nipple playfully, making him break into a grin, which turned into a scowl.
"Well, the date didn't go so well," he admitted. "There was an embarrassing moment for me that I don't even want to tell you. But, I wouldn't be surprised if that was reason she didn't want to see me again." Oscar laughed uncomfortably.
"What?!" Cassandra exclaimed, jumping out of his arms and sitting up to look at him. "You can't tease me like that. Tell me what happened?" Seeing her sparkling eyes and interested expression made Oscar's heart swell. She was adorable when she got excited about something.
"Okay, I'll tell you," he said reluctantly, breaking eye contact. "I went to the bathroom partway through dinner and when I got back to the table, I noticed that my fly was down. So, I discreetly zipped it up under the table. There was a table cloth that hid what I was doing. I thought it was all fine. But when we got up to leave, the entire tablecloth came with me as I stood up, dumping all of our dishes onto the floor. The tablecloth had gotten caught in my fly."
Cassandra's eyes flew open and she let out a cry, "Noooo! Nooooo! That didn't really happen, did it?" Tears glistened her eyes. As Oscar nodded his head to indicate that it had really happened, Cassandra burst into uncontrollable laughter.
Tears running down her face, she shook her head in disbelief. "You poor man. I'm so sorry that happened to you!" She stammered out, trying to stifle herself.
Oscar felt a bit offended at first. How could she find his embarrassing misfortune funny? But he had to admit when he thought about it, it was funny. At least it would be if it didn't happen to him. Now, Oscar started to laugh. It felt good having a sense of humour about it. Cassandra always knew what to do or say to heal him.
"Needless to say, she didn't want to go on a second date," Oscar quipped, instigating another round of giggles. When their laughter died down, they laid together cuddling in silence for a few moments. "So, tell me about your life. Anything exciting happen since the last time I saw you?" he asked.
Cassandra's breath caught for a moment before she answered him. "Well, actually, yes. Something exciting did happen to me. I did a duo massage for the first time but it didn't really turn out to be a duo massage. It mostly turned out to be me making out with my friend Gloria. I had my first sexual experience with a woman last weekend."
It was Oscar's turn to sit up. He braced himself, looking at Cassandra's face, and said, "I didn't know you're bisexual."
"I didn't know either," Cassandra replied. "But lately I've been noticing women more and then that threesome made me know for sure … "
"Threesome! I thought you said it was a duo massage," Oscar exclaimed.
"Oh my Goddess, I didn't mean to say threesome. It's just that we hardly did any massaging. It was mostly just making out."
"That sounds very hot," Oscar replied. "Was the client involved in any of that?" Oscar could feel his cock stirring as he imagined being with Cassandra and another woman.
"Ohhh yes," Cassandra replied absently, seemingly lost in thought. "He was very involved. But I didn't have sex with him or anything like that. It was very hot though."
Feelings of jealousy rose up in Oscar's gut. He pushed them down. He had no right to be jealous. He had no right to ask personal questions either, yet he found himself doing exactly that. "Is your boyfriend okay with you doing that?"
Cassandra winced. He'd hit a nerve. "I don't think he would be, no. I'm actually feeling really guilty about it, even though I had a really good time. I don't know what to do, honestly."
Oscar immediately felt bad for asking. He could see that Cassandra was struggling and he didn't want to make it worse for her. "Do you have to tell him?" Oscar asked. "What he doesn't know can't hurt him."
"Do you think so? I hate to lie but I don't want to tell him either. It's not like I'm leaving him for someone else or having an affair. I got paid for the duo massage. But I don't think he would understand … " Her voice trailed off.
"I think if he doesn't understand then it's probably best not to tell him. Don't make a problem if there doesn't need to be one." Oscar hoped his advice comforted Cassandra. "Now, let's talk a bit more about you being bisexual. Have you always been attracted to women?"
Cassandra laughed. "Oh, I see what's going on here. My story about making out with Gloria is turning you on, isn't it?"
"Well, yes. It is turning me on and it's better than thinking about my horrible, embarrassing date."
"Come on. It wasn't that bad. It could happen to anyone!" Cassandra burst into laughter again. Oscar groaned but he was glad she was in better spirits.
"I'm beginning to worry that I'm going to become that guy sitting in a strip club every weekend, paying hundreds of dollars for beautiful women to sit with me and dance on my lap."
"What's wrong with that guy?" Cassandra replied. "He sounds pretty awesome to me! Introduce me to that guy."
"You can find them in any strip club," Oscar said. "Or should I call it the lonely hearts club."
"Really? Strip clubs are full of lonely men?"
"I'm exaggerating, but haven't you ever been to a strip club?"
"No, I haven't," Cassandra said. "Want to take me?"
"I'd love to. Are you free tonight?"
It just so happened that Derek was leaving today for a policing conference all weekend. He had stopped by her studio in the morning, before her booking with Oscar, to give her a kiss and say goodbye. She was on her own for the night and excited for a new adventure.
Cassandra called her friend, Gloria, and invited her to go out with them. Billionaire Boyfriend Brad, as Cassandra now called Gloria's wealthy client, but only behind his back, wanted to come too. Cassandra was the only one who had never been to a strip club before.
That night when he picked her up, Cassandra noticed that Oscar's front headlight was smashed out. "What happened to your car?" she asked.
"I don't know," he replied. "It happened while I was with you at your massage studio today. I found it that way when I left."
"I'm so sorry," Cassandra said. "I hate that this happened when you were spending time with me."
"It's not your fault! Don't worry about it," he assured her. "Shit happens. Now, let's get going to the strip club. I can't wait to meet your friend that you made out with last weekend."
Cassandra barked out a startled laugh and swatted him playfully. "That's between you and me," she said. "Don't tell Gloria or Brad that I told you."
"I won't," he promised. Oscar felt grateful to have Cassandra in his life. He opened her door like a gentleman and hopped excitedly around his car to get in the driver's seat. This was going to be way more fun than his recent fateful dinner date. This was just what he needed to distract him from his lonely, embarrassing life.
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 true story about someone I know who had the same thing happen on a first date!
Love Annie xoxo