CHAPTER ONE: OSCAR SHARES A SECRET

This is completely new. I’ve missed writing fiction while I’ve been focusing on my memoir and personal development books. Ever since I read Stephanie Parent’s novel, “The Briars,” which features a cast of sex workers in haunted dungeon, I’ve been fantasizing about writing a romance novel with a sex worker and a client as the two main protagonists. Since I write for my blog every week, I decided to use one week a month to write a chapter of fiction. This is the very first chapter!

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CHAPTER ONE: OSCAR SHARES A SECRET

It started with a happy ending. It wasn't Oscar's first handjob, but it was the first one he'd ever paid for. Oscar had been faithful to his ex-wife for almost 30 years. When their youngest child moved out, Stephanie told him it was over. He should have seen it coming because she hadn't wanted intimacy in over five years and for a few years before that, she seemed to be merely tolerating his attempts to give her pleasure. Her reluctance when he initiated and her lack of response during the act made Oscar feel disgusting. He tried to turn her on, studying sexual techniques and suggesting ways to spice things up, but she didn't even try to hide the fact that it was just duty sex to her.

The shame that filled him when he realized he was fucking a woman who didn't want him was sickening. After that, he stopped trying altogether. He treated her with respect and kindness, always hoping she would get that twinkle in her eye that she used to get when they were first together. But the twinkle never came. Oscar took care of his own needs, with a little help from his favourite search words, "passionate sex." He tried not to think about whether or not he would ever have sex again. He was committed to his wife and family.

Now, however, he was sixty, single, and scared as fuck. The divorce had finalized months ago. Stephanie was dating other people now. But Oscar thought he was probably going to be alone forever. It wasn't like he had nothing to offer. He was a wealthy, successful real estate developer. He owned multiple rental properties in multiple countries. He was confident and powerful in his business. But when it came to women, he shrank from the thought of exposing his inadequacies. He had a cock that didn't perform like it used to. What woman would want him if he couldn't satisfy her in the bedroom?

He finally shared his secret when his best friend, Leonard confronted him. "Oscar, my friend," he'd said. "I want to introduce you to a woman I know. She is beautiful and intelligent. I think you will like her." This was the third time Leonard was trying to set him up with one of his wife’s friends.

"I'm not ready to date," Oscar replied shaking his head.

"Buddy, I know that Stephanie hasn't fucked you in over five years. You've been separated and divorced long enough to start dating again. Hell, Stephanie's dating again. What's stopping you? For real, what the fuck is stopping you?" Leonard held Oscar's eyes. "What are you scared of?"

"That's the problem," Oscar replied. "You're right. I am scared. I don't even know if my dick works anymore. I mean, it works most of the time when I wank it but sometimes it's really difficult. What if I get a woman into bed and then I can't perform?" The look on Oscar's face was so serious and pained that Leonard decided not to make fun of his friend.

"Come on. That's all?" he said. "Bro, it happens to everyone at our age. If you're so worried about it, why don't you go to a hooker and test it out?"

"What?! No!" Oscar exclaimed. "I can't do that," he paused. "What if I can't perform for the hooker?"

"She's not going to give you your money back but she's not going to judge you either. It's her business, Oscar. Hookers see guys with dick problems all the time."

"Oh really? How do you know?" Oscar asked, eyebrows arching. Leonard's cheeks pinkened slightly but he answered without shame.

"You already know that Janice hasn't wanted sex with me in a long time either. I'm not like you, Oscar. I can't go years without the touch of a woman. I've spent time with a few different escorts. It's no big deal. Most guys do it." Oscar shook his head. He didn't agree with Leonard that most guys did it. He'd never met anyone who admitted doing it before. But then again, most people wouldn't volunteer that kind of information. He wondered, is it really that common?

"But most of those women are forced into prostitution. They don't want a disgusting old man with dick problems like me touching them. They're just doing it to make their pimps happy," Oscar argued. But Leonard started laughing. "What's so funny?"

"Man, you've been watching too many movies. They're just women working for a living and some of them like their job. I'm serious, man. You should think about it. If you're that worried, go for a massage instead. Then, if you can't get your dick up, you won't have to feel bad about letting the hooker down."

Leonard's laughter indicated that he found Oscar's reluctance amusing. It wasn't that Oscar was a prude or anything. He wasn't even surprised that Leonard was fucking escorts behind Janice's back. But Oscar had always thought that the only men who went to see prostitutes were men who couldn't get laid in real life. Was Oscar one of those guys now?

The conversation with Leonard happened about two weeks ago. A week ago, Oscar decided to scan the adult classifieds listings. He told himself it was just out of curiousity. That was when he saw her. Cassandra. Her face was blurred, but her kind, loving energy came through in her ad. When he clicked through to her website, he found more evidence that this woman, who offered "healing massage" was not likely to make him feel ashamed if he was unable to get an erection.

The idea of getting a handjob rather than engaging in full sexual intercourse appealed to Oscar. Years of rejection and disinterest from Stephanie made him doubt himself. He wasn't ready to test his ability to perform with a woman. What if his skills were laughable? Did Stephanie lose interest in sex because he wasn't good enough at eating her out? Or maybe she found it disgusting when he panted during his own orgasm? He had no idea what it was about him that had repulsed Stephanie so much that she withdrew from him sexually. But clearly, he wasn't good enough because otherwise she wouldn't have left him.

At first Stephanie had made excuses more and more often for why she didn't want to have sex "that night." She was tired or she had too much on her mind. Then she started rolling her eyes when Oscar tried to get her in the mood. When she stopped even pretending to enjoy herself with him, Oscar couldn't bring himself to fuck her anymore. He wouldn't fuck someone who didn't want him to. What kind of monster did she think he was?

It turned out he was the kind of monster who was perhaps willing to pay a woman to stroke his cock. A woman to stroke his cock. The words brought to his mind a small hand clasped over his hard, throbbing dick. He felt a stirring. Cassandra's website showed various photos of her with her face fuzzed out but her beautiful body on full display. As Oscar examined the curve of her ass, the shape of her inner thighs, and the perkiness of her breasts beneath her lacy lingerie, his cock grew harder until he had to shift his pants.

Oh, what the hell. He had nothing better to do. Oscar unclasped and unzipped his pants to release his fully engorged member. Grasping his erection, he closed his eyes and imagined it was Cassandra's hand on his cock, sliding down, then up, then down, then up – slowly at first, with ever increasing urgency. He imagined sinking his own fingers into her soft, wet pussy; her mouth crashing on his as her tiny hand gripped his cock, jacking him off until his moans of ecstasy echoed through his empty condo and hot semen covered his hand and pants.

Oscar sat motionless as intense sensations swept over him. When they subsided, he found himself once again alone in his condo with his dick in his hand. Only this time, his dick was behaving like an adolescent. If this was what Cassandra could do without even meeting her, imagine what she could do in person, Oscar thought. He pulled his tshirt over his head and wiped himself up with it, tossing it on the floor to clean up later.

Grabbing his phone, Oscar looked again at Cassandra's website. Before he could change his mind and chicken out, he sent her a message. It said:

"Hello Cassandra, my name is Oscar. I am a recently divorced man who hasn't been with a woman in a long time. I would like to schedule a massage with you at your convenience. I look forward to your reply."

Cassandra replied almost immediately, making Oscar's heart jump when he saw her response come through. As requested, he sent her a deposit and a face photo. The big day approached and Oscar changed his mind a million times. It wasn't about the money. He would pay her either way. But he didn't know if he had the courage to go through with it. Cassandra specified that he must be sober for their appointment but Oscar thought a stiff drink wouldn't be horrible as he bathed and dressed before going to meet her. Somehow, putting one foot in front the other, even without the stiff drink, Oscar managed to arrive at Cassandra's door on the appointed day at the appointed time.

She opened the door, greeting Oscar with a smile and big hug. She was dressed in lingerie and high heels, but other than a touch of colour on her lips, she was otherwise unadorned. Her shoulder-length blonde hair bounced as she talked and her eyes shone with sincerity. Cassandra was obviously not exploited. She exuded self-confidence and power. Oscar was beginning to sweat with nervousness.

Cassandra had a tinkling laugh that made Oscar grin from ear-to-ear for the whole session. She put his nerves at ease by directing him to the bed right away. Cassandra gave massages on a bed instead of a massage table. She explained on her website that she provided intimacy in her session incorporating skin contact and naked hugs. Oscar couldn't believe he would get to hug this beautiful woman with their clothes off in just a few minutes.

The back massage was tantalizing. Cassandra, wearing nothing but thong panties, alternately massaged his back, legs, and upper thighs, pressed her body against his, ran her fingers through his hair, and nibbled on his ears from behind. His entire body hummed with arousal, his cock throbbing underneath him as he lay on his stomach for the first half of the massage.

When she asked him to turn over, his cock went from hard to soft in seconds. He became for a moment self-conscious about his body and his limp cock. But Cassandra continued to treat him with love and enthusiasm. She massaged the front of his body, occasionally stimulating his cock a little but not until he grew hard. When she lay atop him for a naked hug with their lower bodies in such close proximity, Oscar's cock began to harden. Just knowing how near to his cock her covered pussy was made his heart race with excitement.

Cassandra nuzzled his neck, allowing her thigh to press against Oscar's burgeoning cock, as her arms encircled him in an embrace. The heightened sensations of her breath on his neck, her hard nipples pressed against his chest, and his cock trapped beneath her silky thigh made Oscar wonder if he would come too soon. But Cassandra took her time.

Although Oscar was allowed to touch her with restrictions like no finger penetration and no kissing, he only softly embraced her during naked hugs. He feared his touch would turn her off. He wasn't confident in his ability to give her pleasure. Cassandra asked him if he wanted to watch her touch herself until she came. Oscar nodded emphatically.

The hour flew by. Oscar's cock worked great. Cassandra's tiny hands were even better in person than in his fantasy the week before. But his orgasm wasn't the best part of the experience. Every moment was incredible, but it was in the moments after he climaxed, as Cassandra lay next to him, her head in the crook of his arm running her hand over his body, chatting softly about life and love, Oscar felt cared for.

Cassandra's tender touch and seemingly genuine interest in what he had to say made him feel like maybe, just maybe, he wasn't doomed to be alone forever after all. Cassandra had reawakened something dormant inside him, a desire to find a companion. Oscar practically bounced as he walked for the next few weeks. He smiled at strangers in the street and he booked another appointment with Cassandra. He also decided he was ready to start dating again. Maybe.

CLICK HERE TO READ CHAPTER TWO.

This was chapter one in the saga of Oscar and Cassandra. Subscribe to my newsletter if you want to know what happens next.

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