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Author’s Notes: This story has been posted to Literotica.com with the full knowledge of the original author, SinFantasy. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author.
All characters engaging in any form of sexual activity are at least eighteen years of age.
This story has been edited by me using a basic editor. You may find mistakes.
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Laura felt sad as she carried her bags down the stairs. There she was, leaving for another last-minute trip.
“Don’t be like that, darling. I promise this is going to be my last trip and I will try to be back as soon as I can.” She assured her boyfriend, Rob.
“I know, dear, but that doesn’t make it any easier to stay away from you. We also have a Halloween party tomorrow, and I’ll miss you.” Rob replied dryly.
This was not the first time she had to leave at a moment’s notice. Laura felt guilty at the mention of an upcoming party. They had planned to go together, but he would be all alone now.
“I promise this will be the last holiday you will be spending alone,” she assured him. “Once this project is over…”
Before she could finish her sentence, her phone rang. Her cab had arrived.
“Okay, take care of yourself. I’ll call you once I reach the hotel.” She kissed him before leaving.
“Take care and have a safe journey,” he wished her goodbye.
Rob had a smile on his face. It was easy to make Laura guilty. He was sure that she would bring something expensive as a gift for him.
Rob was a serial cheater, and Laura was a perfect girlfriend for him. She was ignorant, a workaholic, and most importantly filthy rich. She was easy to please, did not ask for a lot of time and attention, did not ask to spend money on her, and the sex was mind-blowing when she felt guilty. Her frequent business trips were icing on the cake. He was practically living a bachelor’s life with a sugar momma willing to spend money on him.
*********
Rob wanted to do something different this time. Rather than visiting his usual spots, he decided to go to the singles Halloween party with optional speed dating. He had met Laura in similar settings and wanted to see if he could get another sugar momma.
Rob entered the hotel ballroom decorated with a spooky Halloween theme. There were lots of balloons of various colors with scary faces. There were some skeletons, but they looked out of place. Surprisingly, he missed the carved pumpkins and Jack-o’-lantern. There was a live band, but they were playing upbeat music that did not go with the theme.
Rob had not bothered to get a Halloween costume. He was dressed in a crisp white shirt, sleek black blazer, and tailored dark pants with polished formal shoes. He had shaved clean and applied generous cologne.
Looking around the room, he had a specific target in mind. He was looking for someone sophisticated, independent, and someone busy or important, just like Laura.
There were many women of all ages, dressed in various costumes. There was a busty nurse, a vampire, an angel with devil horns, several sexy witches, and even one dressed as a pirate with an eye patch. He looked at the surrounding men, and most of them were dressed in costumes. While he could understand superhero costumes, he could only sigh at someone dressed as a bear can. But the worst of the night was yet to come. There was someone who had tried to dress like a Charlie Chaplin but ended up looking like a Hitler.
He grabbed a drink and focused on his main objective to be here. While there were many desirable women, most of them did not match his criteria. He soon found a sexy mature woman dressed as Catwoman with a black latex suit. The costume looked super sexy on her voluptuous figure. Her curves were highlighted properly, and it felt like she was on the prowl.
He tried to reach her, but it seemed like she was trying to avoid him. Not giving up, he followed her closely. He finally found the opportunity when she lingered in a corner after speaking with someone dressed as ‘Fred Flintstone’.
“Hi there, I’m Rob.” He extended his hand as he greeted her.
“Nice to meet you, I’m Anna,” she smiled as she shook his hand.
They chatted for a while, but Anna did not talk much about herself. She expressed her interest in the speed dating part of the evening, though.
“I was looking for someone like you here,” Rob said confidently.
She raised an eyebrow. “Oh really? And why is that?”
“Well, the last time when I was here, I met someone so much like you,” he explained. “And let’s just say she was very generous towards me.”
Laura smiled at him knowingly. “I am not interested in short-term flings or being your sugar momma. Meet me after the speed dating is over if you are interested in some long-term commitment.”
With that, she left to mingle in the crowd.
The speed dating part was utterly boring. He usually mingled in singles bars where people mostly looked for one-night stands. There was no reason for him to be interested in listening to the life story of the person sitting opposite him. He wanted to focus on finding someone similar to Laura, but his eyes still lingered on Anna. There was something about her that he found difficult to ignore.
They were almost at the end of the event when Anna waved him over to her table.
“Did you meet anyone interesting yet?” she asked.
“Not really,” Rob shrugged.
“Are you sure you know what you need?” she asked him coyly.
He smirked as he looked around. “I know what I need, but I don’t think I will find it here.”
He paused and looked her in the eye. “Maybe we could continue our conversation somewhere more private?”
She returned his gaze with a challenge of her own. “And my question still stands. Would you consider something long-term?”
He paused before responding confidently. “I won’t mind spending eternity with you.”
Her eyes sparkled at his response. “That’s all I wanted to hear.”
They quickly finished up their drinks before heading out to the parking lot. Getting into Anna’s car, they drove off to her residence.
*********
On the way, Anna asked him about who he had met previously. Rob usually played safe with such questions and had many sob stories ready for such occasions. But this time he answered all her questions honestly. He told her about Laura, how they were in love, and how Luara wanted to get married as soon as she could complete her current project.
“So, help me understand, Rob, when you have such a wonderful woman as a girlfriend, why do you cheat?” She asked seriously.
“I think I am obsessed with falling in love. I mean, I love the chase but not the catch itself. You know what I mean?” he tried a brief response.
“You mean, you like making women fall for you? You love the challenge, but once that is done, you lose your interest?” She asked to clarify.
“Something like that, but I am not necessarily looking for a challenge. Well, maybe a little bit, but mostly it’s about being with someone new,” he responded.
“What If I allow you to be with me and look for someone new every now and then, would you consider leaving Anna and being with me?” she asked.
He laughed at that. “If you are so honest about it, it kind of kills the fun. After all, half of the fun is in cheating on your partner. But yes, I would consider it. I have been with Anna for five years now. I think it’s time I should move on and look for someone new.”
She had another spark in her eyes. “Oh, you have no idea how good honesty can be when you feel the chase every time.”
Rob squirmed in his seat uncomfortably. “I thought you wanted to do something long-term. I don’t think I will be comfortable if we both go on a chase.”
Her eyes sparked even more. “Oh, how selfish of you. You want to have me devoted to you, but you want your freedom to chase all the women you want. Is that right?”
He nodded. “Hey, I never claimed to be fair. I am just being honest, as you asked.”
She had a wide smile on her face. “Oh, I liked your honesty. Let me ask you one last question. How long does the chase last for you? I mean, let’s say you are chasing me, when would you conclude that you are successful? And if that does not happen, when would you say you failed and move on?”
He smiled, “That’s simple. The chase concludes only when I hear a love confession from you. And I do not give up. Do you know, it took me two years to hear the love confession from Laura? As for you, I will be in no hurry.”
Her eyes were shining positively now. “We will see about that.” She said with mischief.
*********
Rob was chasing Anna on the empty grassland. There were many Jack-o’-lanterns around them. Anna was dropping one piece of clothing at a time as they approached the large bed placed in the middle of the grassland. Rob did the same as he started stripping his clothes on the way.
By the time they reached the bed, both were stark naked. Ron stopped to admire her beauty. She had pale white skin that had an ethereal glow. Her nipples and pussy lips looked prominently pink and glowed along with her skin. Long hair shifted from black to orange and then to burgundy red, creating a mesmerizing pattern. Her eyes were glowing. Her beauty was otherworldly, and she was the most beautiful woman he had ever seen.
He pulled her into a tight hug. She felt slightly cold, but her passion burned bright as she responded to his hungry kisses.
“Oh god Anna, you taste so good.” He continued slurping her lips as he tried to hold her closer to him.
She had tears in her eyes. “Yes Rob, just like that. Make me feel loved for tonight.”
“Your wish is my command, my dear,” he said as he started kissing her face, her neck, and her ears. He smothered her with kisses as he slowly moved down toward her breasts.
She continued to encourage him with her seductive whimpers and moans. He sucked on her nipples, as he felt a sweet milk flooding his mouth. The taste was out of this world.
“Yes, my dear, take it all. Take anything you want, just make me feel loved.” She coaxed him to continue.
Soon he was drinking from her love nest. Her sweet nectar fell into his mouth, setting his senses on fire.
As their lust escalated, so did the enthusiasm of the jack-o’-lanterns around them. They had followed Rob and now they circled the bed, jumping in joy.
“I can’t take it anymore dear, make love me to me. You promised me the chase. Now you have to fulfill it, fill my needs, make me love you.” She urged him.
Rob happily obliged. He got on top of her in a missionary position. Poised to penetrate her dripping pussy with his long, erect cock.
“Yes, my dear, I will make you fall in love with me or die trying,” He smiled as he pushed his cock into her pussy with a deep powerful thrust.
“Oh… I am counting on it, my dear,” she said as she started lifting her hips in sync with his movements. They were fucking in slow, sensual movements. It was a dance of lust, seduction, and loving pain.
Rob was lost in utter mind-numbing pleasure as the jack-o’-lanterns around them started cheering for him.
“Oh Anna, this is too much. I am cumming.” Rob shouted out loud as he started shooting his cum deep inside her pussy.
“It’s ok, my dear, cum as much as you want. You can start again after catching your breath.” She responded in a loving tone, filled with longing.
Rob fell on top of her in utter exhaustion. He had a last look at the jack-o’-lanterns before passing out. They had dimmed by now and looked sad.
*********
Laura woke up from her sleep with a nightmare. She heard Ron calling for her to help, but she could not find him. She tried to call him, but he did not respond to her calls. Looking at the time, she slept again. She would try to reach out to him tomorrow morning.
Rob did not respond to her call for the next two days. She called her friends, but they had not seen Rob at the Halloween party or after that.
She cut her trip short and was back in town. With no other leads, she filed a police complaint. There was still no news for the next two days, and Laura was losing her mind.
Police found the lead on the fourth day and reached the location of the single’s Halloween party. However, there was still no further lead on Rob.
One of the hotel’s old caretakers looked at the distraught Laura and suggested checking the abandoned graveyard on the outskirts of town. He wished her luck before going away.
The police detective agreed to accompany Laura to the location.
The graveyard looked like an empty grassland, long abandoned. Most of the gravestones were broken and crumbled. They were ready to give up searching until Laura found a male shoe in the distance. Following the trail left by Rob’s clothes, they reached a single intact gravestone right in the middle of the grassland.
Rob was kneeling in front of this gravestone naked. He looked dirty, malnourished, and dehydrated.
He was holding a bunch of wildflowers in his hand, singing love confessions to Anna, his eternal love.
—– The End —-
**Author’s Notes. I write these stories for pleasure and post them here for your enjoyment. Thank you sincerely for reading my stories. I especially thank those that leave comments, good and bad. Likewise, I also thank those who take the time to rate my words and those who ‘favorite’ my work.
This story is written for the Halloween 2024 story contest. Please be sure to take a moment and cast your vote for this and for any other stories from the other excellent writers who post for this contest. Thank you in advance.
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