All characters are over 18 and all sex is consensual. Also note, this is my entry for the 2024 Literotica Halloween contest, so if you enjoyed this tale, please give it a vote. Enjoy.
Halloween, 9AM
Nate yawned. He had already been clocked on for an hour but couldn't bring himself to be productive. He had been in meetings all week and the afternoon looked like it was going to be back-to-back until 5pm. They were implementing a new process that he needed to have knowledge of, but didn't directly impact his team. He was so behind on his actual work because of this that starting now was essentially pointless. Thankfully he had been on top of his emails and was able to give status reports to his most pressing clients while "taking notes".
Besides, it was not only Friday, but Halloween, as well. His and his twin sister Natalie's favorite day of the year. They had been planning this night since late September and had a game plan set in stone: a neighborhood haunted house, four separate parties (more like ten, but the other six were back-ups) and a reservation at an upscale restaurant in Queen Anne that Natalie's roommate was the executive chef at. The only two things that had definitive time constraints were the haunted house and the dinner reservation.
The haunted house was one that was put on by the McCallister family in the neighborhood that Nate and Natalie grew up in. They had been doing it for a couple generations and it improved year after year. The twins had been going to it every year since they grew out of trick-or-treating. Even when the two of them attended separate colleges, they still made time to visit it. And this year had the promise to be the best one yet. This year's theme: The McCallister Morgue.
As far as the dinner reservation, it was a new restaurant that was already getting a lot of buzz. The chef had already three successful Michelin star restaurants (in Los Angeles, New York, and Nashville, respectively) and Nate was elated when he found out that he would have a chance to see if it was going to live up to the hype. Not only that, but they were doing a special tasting menu, just for Halloween. Both food and beverages. No other information could be gleaned from the website and Natalie's roommate was under a strict NDA. He was just hoping that his Peter Pan costume wouldn't stick out like a sore thumb.
His Peter Pan costume. It had not only been Natalie's idea to wear matching costumes, but she had ordered them before he had had a chance to even discuss it with her as to what they could wear. She was going as Tinker Bell, so naturally he had to go as Peter Pan. The big problem with that was the fit. It, well, accentuated a certain area of his anatomy. In other words, the bottoms wore like a pair of grey sweatpants, and he felt like his crotch was on full display when wearing it. Not only that, but it was incredibly uncomfortable to wear with underwear as well, so he would be going commando. Which was why, when he showered before work, he made extra sure to manscape.
He got a ping, shaking him from his thoughts. His boss had gotten a call from the company's top client saying that they had been contacted by a competitor who was offering much better rates and that he needed to reach out to them immediately. All thoughts of Halloween (or attending any of the meetings) went right out the window as he sprang into action to save that account.
Halloween, 6PM
Nate closed his laptop and rubbed his eyes. Crisis was averted, for now, but it took him most of the day to get to that place. He had a pounding headache and reached for an edible that he kept stashed near his desk for days like today. He figured that one edible wouldn't be enough to alter him too much. Just enough to take the edge off the day and get rid of the headache. He stood up, cracked his neck and back, and did some simple stretches to loosen himself up. The last thing he wanted to be was tense when he should be having the time of his life. And hopefully ending his dry spell.
Nate had started the year the same way Natalie had: engaged. By Labor Day, the twins had the same relationship status: single. For Nate, he and Jessica just kind of fizzled out. They had dated all through college and once their perspective careers kicked off, the romance dwindled. The whole reason that Nate had proposed in the first place was because he felt like that's what you do after dating someone for five years. It lasted six months before they mutually amicably ended both the engagement and relationship. Since then, they've evolved into close friends. Which suited Nate. He was enjoying the freedom of single life but had not gotten laid since the breakup.
Natalie's relationship detonated. She found out three weeks before the wedding that her maid-of-honor was pregnant. And the father of the child was Natalie's fiancé. It quickly came out that he had been cheating on her for most of the length of their relationship. He had not only gotten her maid-of-honor pregnant but had also previously slept with her other three bridesmaids, as well. Nate had to pick Natalie up from the ashes and had slept in her condo more than his own apartment for three months straight. Many nights of holding his sister while she cried herself to sleep. Thankfully, his company gave him unlimited PTO during this time, so his paycheck didn't take a hit.
And this Halloween was Natalie's way of saying "thank you" to Nate for him getting her through that tough time. While, yes, the two of them had done some planning together on the night's festivities, most of it he was completely in the dark about. Even the Peter Pan costume was sprung on him. All he truly knew was three things: they were going to hit their neighborhood haunted house, they were going to a fancy restaurant for an amazing dinner, and they were going to be hitting some wild parties. He was just along for the ride for everything else.
Speaking of ride, he had one a contest at work that awarded him three different gift cards: $100 for Starbucks, $100 for Door Dash, and $100 for Uber. He had specifically saved the Uber one for tonight. He had zero plans on being sober enough to operate a motor vehicle. He had already let Natalie know about this and she loved the idea. She told him that she would pitch in after the gift card was used up.
Nate texted Natalie letting her know that he was done with work, and that he would get ready quickly and Uber over to her place. She texted back a thumbs up and told him that she was running slightly behind, but that they should still be on track for everything. He used the bathroom, shaved, put on aftershave and freshened up his deodorant, brushed his teeth, and then changed. As he put on his costume, he was grateful that the edible was starting to kick in. His self-consciousness was easing, and he was just feeling silly instead of embarrassed. It's Halloween. People are supposed to dress funny.
Before leaving, he set out a bowl full of mixed candy that he had bought last night. He knew that it would be empty within the hour, but he didn't care. It was Halloween and he was doing his part. He had also decorated his front door with fake police tape put out his Halloween door mat. With his crazy work schedule and budding social life, he didn't have much time to decorate. As he passed down the short hallway that led outside, he saw that it was already dark, and it was pouring rain. Typical Seattle Halloween.
He briefly considered going back and grabbing a hoodie, but his Uber showed up, so he darted to the car, instead. Uber Number One turned out to be an old work friend. They had both worked at a startup that had a lot of promise...up until it went belly-up. His former colleague was fortunate enough to have fallen in love with; and marry the former COO of the start-up. Who went on to start her own IT company that was an overnight success. He started driving for Uber because he was bored being a house husband. Before Nate got out of the car, they swapped phone numbers and promised to grab a beer soon.
He darted from the car to the entrance of the condo and was buzzed in immediately. He was a little disappointed that the cute redhead receptionist wasn't working; but it didn't dampen his mood any. He had a mild buzz from the edible, his headache was gone, he got to meet up with someone he had lost touch with, and it was going to be an amazing night with his favorite person.
He knocked on the door and shivered slightly from the damp costume and the cold hallway. He waited a beat and was about to knock again when she opened the door slightly and poked her head out. She lit up when she saw him and said, "Come in, but close the door quickly. I...uh...did not realize how sheer this costume is."
He suppressed a laugh, and then slipped in through the crack and closed the door behind him. There, standing 5'7 (now at least 5'10 in her three-inch black heels) in what was the least amount of green fabric to pass as a fairy costume. He could also see right away that not only was his sister not wearing a bra, but apparently had gotten her nipples pierced at some point. And it was a true work of fae magic that he couldn't see her vagina, considering the size of her "skirt". Her doe brown eyes were starting to water, and he knew that she was on the verge of a panic attack.
He locked eyes with her and told her to breathe in time with him. He took a deep breath, and so did she. He held it for a mental count of ten, and then slowly breathed it out. So did she. He did that twice more and he could tell that the moment had passed. He then smiled at her, pointed to her dirty blonde hair, and said, "At least that part you didn't have to do anything with."
She smiled at him and said, "Actually, I got a haircut. Thanks for noticing." She stuck her pierced tongue out at him. He responded by sticking out his tongue at her.
