Hello! If you didn't read the summary this is a finalized version of this fic. Originally called The Spookiest Season, I have taken it back to its intended form of being a contest between a couple. The stories themselves are the same, though the order has changed slightly. The prologue and epilogue are new. EXPLICIT CONTENT. Be warned.
Prologue
A Friendly Halloween Wager
The dim lights of the restaurant added to the ambience as the couple sat across from each other in a booth near the back of the establishment. There was an almost empty basket of fries between them. The place was already decorated for Halloween, even with it only being the first week of the month. There were die cut cardboard pictures of witches and ghosts and pumpkins and black cats that looked like they came straight from an elementary school's decoration closet. The feeling of nostalgia was overwhelming, in a good way.
They had been discussing something for the majority of their meal, each of them becoming more intrigued by the idea the more they talked about it. It had started as a joke but the more she thought about it the more determined she became. It might even become a tradition. And it would definitely be a fun wager with him.
"Would you really want to?" He asked.
"I think it would be fun. But no first person. It would have to be like a narrator telling a story. Like third-person omniscient." She had slipped off her shoe and her sock covered foot was lazily stroking his ankle under the table.
"Oh, come on. First person could be really hot. I move to strike that rule." He grinned.
She sighed, feigning annoyance, and then matched his grin. "Motion carried."
"So like, what? How many do we write?" Seeing her excitement over her proposal was piquing his interest greatly.
"Hmm, why don't we each write three? And then on Halloween night we can read them and choose a winner." Her eyes sparkled in the light above the table, even though it wasn't bright. "We could make candy apples and carve a jack-o-lantern and read our stories and see what happens." She chuckled lightly, knowing exactly what would most likely happen.
"What does the winner get?" He asked teasingly.
"Whatever the winner wants. Oh, but you can't hold back. They all have to be the dirtiest stories you can think of. But, like, hot. Not distasteful," she added.
"God, I love October. I love Halloween!" He grinned, still a little shocked at her idea. "This will be too easy. You know I can write," he mocked her as they slipped out of the booth, having paid their check.
"Hmm. We'll see." She looked back at him over her shoulder as they walked out into the already chilly night air, her eyes wickedly seductive.
He knew he had better bring his A game.
All throughout the month of October, she thought about what she'd want as her prize if she won the story contest. She didn't hold back, putting her fantasies to paper, and it gave her ideas for her actual life. She wanted to escape from the comfortable routine she had with her gentle and sweet lover.
In other words, she wanted something different…kinkier.
So on Halloween night, the night they were to read their stories to each other and choose the winner, she made no mention of the items she had purchased a couple of weeks earlier, wanting to surprise him. They were going to carve the jack-o-lantern, something he very much liked to do, and she thought it would be the perfect time to kick her Halloween fun into gear.
He already had the pumpkin almost completely gutted and they were discussing what sort of face to carve when she could wait no longer.
"Um, could you do me a favor? I left a little bag on the couch. Could you bring me what's inside?" She asked coyly, knowing that his hands were covered in pumpkin guts. She knew also that he would still do whatever she asked. She could tell that he was slightly annoyed but he didn't say anything to that effect. She smiled as he disappeared into the living room, returning seconds later with a confused look on his face.
Before he could speak she turned and lifted her little black skirt.
"I want you to put that inside me. Put it here," she lifted her leg onto the table, forgetting about the pumpkin, and spread her ass cheeks for him.
He stood there with his mouth open. She never did stuff like this and he found himself starting to feel his dick spring to life as he gazed at her…her over the knee socks that were striped with orange and black all the way up, her short black skirt which was currently raised, revealing that she wasn't wearing panties. Her bare pussy was almost shining. He had barely noticed that her black Halloween t-shirt had been pulled up and tied into a sort of makeshift crop top. Now he noticed her smooth skin and how her muscles clenched as she lifted her leg and spread herself for him. He looked back to what he was holding in his hand.
"You want me to put it in?" He still wasn't sure, even with her standing on display and him holding the item in question.
"I want to have it in while we read our stories. I think it'll be really hot. Don't you? I want to feel it. I want to feel you slide it into me and then I want to keep it in until we finish the stories. Won't you please put it in?"
He could never say no to her. In all honestly, he'd thought about doing something like this a lot but he had always been afraid to suggest it, always fearing that some part of her might consider it too similar to things that had happened to her as a child.
But now he knew she wanted him to do it. He looked down at his hand, which was holding a shiny silver metal butt plug with a clear diamond-looking jewel for the base. Just thinking about how she would look with it inserted into her ass, and then thinking about her having it in all night while they read their sexy stories made him instantly hard. He wanted her right then but he'd never just take her. He would always watch out for her. He had promised her long ago.
He crossed to her, running his hands over her smooth thighs and her ass before gently probing her asshole with his finger.
"What if it's cold?" He asked as he started to slip his slender finger inside, wanting to ease her into the intrusion that would be the butt plug.
"It'll warm up. Slide it in. And don't worry, you can take as long as you want. I know it probably looks hot to watch it go in. You can even slide it in and out a couple of times. If you want."
He did just that. He found himself holding his breath as he pushed the shiny tip of the plug into her, watching as her tight hole began to accommodate it, began to open up. He took it back out and then did it again, sliding in further the second time. He liked watching how her perfect asshole would open up as he pulled the plug back out, the wider part making her hole stretch and smooth the rigid skin there. Then he slid it back in, all the way, until the jewel prevented him from sliding any deeper. He marveled at the sight, the little jewel crowing her asshole and knowing that he'd slipped something inside her that would open her up, that she would keep it in for hours possibly, and that she had wanted him to do it. He wondered what else she'd want him to do.
"Mmm, feels good. Full. We can use the other thing I got later. Let's give this guy a face and then read our stories. I wanna see how wet you can make me. We can discuss prizes after we pick a winner. Though I don't think either of us is going to feel like we lost." He was still behind her and she was pushing herself into him but she didn't want to rush things. They had all night.
"Let's carve a scary face," she grinned, getting used to the butt plug and looking forward to moving to the living room. Picking up the carving knife, she felt his hand slide over hers. They would carve together.
"Don't forget to help me with the eyes."
With the jack-o-lantern carved, somehow ending up with the perfect scary face with creepy round eyes and jagged teeth, the couple retired to the living room to finally tell their tales. She was getting more turned on, feeling deliciously naughty with the butt plug in her ass, and could feel how she had leaked arousal all over her inner thighs. She wanted to touch herself but she refrained, wanting more to find out what kind of stories she was about to hear. They decided to switch off, with him going first. She sat back as he began to read, letting her sock covered foot rest on his thigh while her other leg was on the floor, effectively spreading her legs and allowing him to touch her if he so chose.
He got comfortable as well, holding his story in one hand and letting his other rest loosely on her inner thigh. He could feel that she was wet. It only made him harder.
Both already turned on, he started to read his first story. She sat rapt with attention as he spun his first yarn.
Author's Note: Again, the following stories have not been changed other than the order. Thanks for reading. I know it's not Halloween anymore but in my house it's Halloween all year. It's kind of my jam. So have fun!
