Family 'adult' Halloween Party

Author Notes

This story was written for the

Halloween Story Contest 2023

. I hope you enjoy it!

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Chapter 1: Ulterior Motives

"Hiiiiii Tim," came the voice of Tim's mom in an exaggerated hello. She wanted something.

"Hey mom, what's up?" Tim replied applying as little emotion as possible.

"Hey baby, I know you probably already have plans for Halloween, but... I really, really, really, really, really want you to come to our house this year. We're throwing a big party, and you should come!"

Tim didn't have plans for Halloween. His mom, Melanie, had ulterior motives. Why on earth could she possibly want him to come to their annual Halloween party so badly this time? Melanie and Tim's Stepdad, Steve, had thrown a Halloween party every year for at least a decade, what was so special this time? And, for the record, the party was always "big."

Melanie and Steve had gotten married after Tim's dad died in a motorcycle accident when Tim was 12 years old. Melanie had had Tim when she was young, as a Freshman in College at the age of 19. Tim was the result of a slip-up in the birth control department. Raising a kid while finishing college and struggling to get careers, marriage, and a child off the ground caused Tim to be an only child.

Tim was now 22 years old, making Melanie 41. Melanie had taken very good care of herself over the years, and I suppose you could say that it paid off for her. Melanie was 31 when she married Steve who was 15 years her senior. Steve is an eccentric serial tech entrepreneur, who had never married until Melanie came along.

Tim couldn't be sure how wealthy Steve was exactly, but from the age of 12 on, Tim grew up in Steve's $2.2 Million Dollar Home on the lake in Coeur d'Alene, Idaho. Steve was always flying back and forth to California but would at times be home seemingly retired for several months at a time. Now at the age 56, Steve found that generally if he couldn't close the deal on a ZOOM call, he wasn't interested in the project. Not that he could be blamed for that. Coeur d'Alene was a beautiful place in the summers, and in the winter, Steve and Melanie would temporarily move to their home on the gulf in Galveston, Texas. Halloween always signified the beginning of that transition as it was always the last big party of the year on the lake in Coeur d'Alene.

Tim had gone to the University of Texas, opting to enjoy the warmer weather year-round, and would see Melanie and Steve more often when they were down in Galveston than in Idaho. Tim landed a job in San Antonio after graduation and was currently living there. Point being, it wasn't a simple task for him to "come to a Halloween Party" in Coeur d'Alene. No non-stop flights, and at least 5 and a half hours to fly up to Coeur d'Alene. Tim genuinely wasn't sure if he wanted to make the effort to go up to Coeur d'Alene, and Melanie could sense Tim's hesitation.

"Of course, we'll buy your plane tickets, and we'll even grab first class for you," Melanie offered. It was a nice gesture.

"Look mom, I'd have to check on work, and it's a long flight, and just to come up for one party... I don't know, it just seems like a lot to ask," Tim meant every word, it seemed kind of silly for him to come up there. Besides, maybe a little resistance might cause his mom to spill the beans on the real reason she wanted him to come.

"Oh honey, don't come up for just the party, you should come out early. Halloween is on a Tuesday this year, and you can't fly back that day. So why don't you come up on Friday on a late flight after work. And take a few days off next week. Or maybe they'll let you work remotely for a week? If they do that, you can stay the whole week maybe?"

Tim didn't understand why his mom was asking him to stay for so long. It didn't make any sense. They were usually packing before the Halloween party and after it, he would just be in the way.

"I don't know mom. I don't want to ask for any special favors at work right now. I might actually need some later," Tim replied.

"Okay honey, I get it, I really do. So... ummm... what if..." Melanie sounded apprehensive, "What if... I told you, that I miiiiight have sort of, told your Aunt Kelly, thaaaat, you could probably help her get her office redesigned."

There it was. Tim's Aunt Kelly owned a small insurance agency in town for the last 15 years. It probably was time for a redesign. Tim was an architect and so he was certainly capable of helping, but his mom was asking him to come to a "Halloween Party" and then what? Spring this whole office redesign on him as a side project while he was there? It wasn't out of character for Melanie to volunteer Tim for things without asking him, and he wasn't even put out by it, but it still annoyed him slightly at the whole charade of it all.

Tim sighed heavily, "Okay fine. How much does it pay?" Tim already knew the answer.

"Oh honey, you know your Aunt Kelly isn't raking it in it, maybe you could just help her out?"

"I know, I wasn't serious anyway."

"Thank you, Tim, really, I know Aunt Kelly will really be appreciative too! Maybe she can set you up with one of her hot young new hires while you're here as a thank you!" Tim's mom and Aunt Kelly were always trying to set him up with someone. He didn't even try to object to the idea as he knew it wouldn't do any good anyway.

They had set him up a few times before with mixed results, but it had given him some fun experiences over the years. He even lost his virginity to one of his Aunt Kelly's employees before he went off to college. Tim felt some swelling in his groin thinking about the prospect. Since moving to San Antonio, Tim hadn't had many opportunities to get out and socialize and meet people. He wasn't dating anyone yet, and there weren't even any prospects on the horizon. The company he worked for was mostly men, and the women who were there were too old, too overweight, or too married to interest Tim.

"Sure thing mom. Hey, listen, I need to head out and pick up some groceries, but I'll text you if I get the time off or am allowed to work remotely."

"Sounds good, and we'll book the plane flights for you."

"Perfect, say hi to Dad."

"I will, I LOVE YOU!"

"Love you too mom, bye."

Tim had gotten used to calling Steve 'dad' reasonably quickly. Steve really had put a lot of effort into their relationship, and it was easier and more natural to refer to him that way when people were always asking "is this your dad?" as Tim was growing up. Tim quickly texted Steve.

"Thanks for the airfare and first class."

"Absolutely, looking forward to seeing you!" came Steve's reply.

Tim ended up simply taking some time off work. He let his mom know that he would come up Friday, and work the weekend, Monday, and Tuesday with Aunt Kelly on her remodel project. She was obviously thrilled.

******

Chapter 2: Hot Aunt Kelly

Tim arrived at the airport in Spokane, Washington (as it was the closest airport to Coeur d'Alene) just after midnight. Luckily, he had slept on the plane, and with first class tickets, he was feeling reasonably refreshed. After grabbing his bags from the carousel, he was about to text Steve when he heard someone call his name.

"Tim," Tim looked up to see his Aunt Kelly walking towards him. "Hi, sorry I know you weren't expecting me, but with a late flight and the fact that you're here as much for me as anyone else, your mom thought it was fair that I come get you!"

Tim always admired how well his Aunt Kelly took care of herself. She was Melanie's younger sister by 5 years and that made her only 14 years older than Tim. Melanie had dark hair that she kept ironed straight. Melanie often wore her hair pulled back, and tonight she had it pulled up into a ponytail. Her angular facial features told Tim that she still ate healthy (probably still a vegan) and worked out routinely. At midnight in the airport, Kelly was dressed quite casually, wearing leggings and a sweatshirt. Her sweatshirt hid a toned abdomen, well formed tits, and a small waist (or at least that's what Tim remembered from seeing his Aunt Kelly in a bikini more than once). It was common for Tim's friends in High School to remark how hot his Aunt Kelly was. Tim couldn't really disagree.

"Hi Aunt Kelly. No problem. I've got my bags already, so I think I'm set, thanks for picking me up."

Kelly moved in and gave Tim a hug. He let go of his bags momentarily to hug her back and was reminded again that "Hot Aunt Kelly" still existed.

"Great. You know what, it's really good to see you," Kelly said as they broke the hug. Kelly took ahold of one bag, and Tim took the other as he followed her to the parking garage. Once they were settled into Kelly's car, they had about an hour drive to get to Steve and Melanie's house.

"So, tell me about this remodel you want to do?" Tim asked.

"Oh my god, I don't know if I'm crazy to do it or not, since COVID has been done for a while now the business is starting to pick up again and people are coming into the office more often. I probably should have done this 10 years ago when we had some of our best years, but this year is looking pretty good so I think I can afford to get it done now, and then we'll be off to the races after that."

"Makes sense," Tim replied, he had been in Kelly's office many times before. The layout was pretty simple, 5 stand-alone offices with cubicles in the middle for administrative staff, and insurance agents who hadn't earned an office yet.

Kelly continued, "Yeah so, I want to try to avoid tearing down as many walls as I can, but I also want to get a few more private conference rooms, maybe move most, if not all the staff into the open area. Something like that. But I can't really envision how it will go... I mean, do we convert what's already there, do we do something with the supply area? Do I want to keep an office? Ahhhh... too much! I NEED HELP!" As she made her last plea, Kelly reached over and grabbed Tim's arm shaking him as though he was her only hope.

They shared a laugh together at Kelly's desperation. Tim was confident he could help her decide what to do. It was probably saving her a couple thousand dollars to have him do the design instead of paying for it. This reminded Tim of the 'payment' he was due to receive at his mom's promise.

"Have you hired anyone good-looking lately?" Tim asked causing Aunt Kelly to smirk.

"Already thinking about payment before the work even starts huh?"

"Well... can you blame a guy?"

Aunt Kelly laughed, "No I guess not. I have a couple in mind for you. Don't worry. Oh, that reminds me! Did I tell you that Holly started working for me?"

Tim thought it was funny that Aunt Kelly would bring up his cousin Holly, and Kelly's only daughter, when they were just discussing who Kelly might be able to set him up with. Holly had recently turned 18 and graduated high school.

Kelly and Melanie were sisters with at least one thing in common, apparently, birth control issues. Kelly had given birth to Holly at 18, to her then boyfriend. Who gave an effort initially, but ultimately ditched out and was 'who knows where' at this point. Kelly had moved to Coeur d'Alene to be close to her sister so that she wouldn't be raising her daughter completely on her own after Melanie and Steve had married. Holly and Tim had roughly grown up together as a result, and even though Holly was 4 years younger they had remained friendly to each other over the years even when it could have been awkward.

Holly wasn't quite the spitting image of her mom, she had her dad's blonde hair and stood taller at 5'9", but she definitely had a lot going for her in the looks department. She had adopted her mom's vegan and yoga lifestyle and Tim mused that if Aunt Kelly had offered to set him up with Holly it wouldn't be the worst outcome ever. The taboo thought of it made his heart race and he pushed it out of his mind as quickly as he could before his cock took over the fantasy. Tim and Holly were Facebook Friends and Tim followed Holly's Instagram so it wouldn't have taken much for him to recall the images of a bikini clad Holly enjoying the lake in the summertime to fuel such fantasies.

"Tim?"

"Huh?"

"Oh, I wondered if you fell asleep on me there."

"Oh sorry, no I was just thinking about the remodel project. That's great that Holly started working with you, what is she doing?"

"She got her license and is selling insurance of course. She's still deciding if she wants to go to college. But she's been doing really well at sales, so I don't know what she might do at this point. I don't really have extra money to pay for her to go to college, and she doesn't have the grades to get a lot of scholarship money. So, if nothing else, she can pay her own way if she keeps selling insurance. I mean, that's basically what happened to me. Your Aunt was a hot young insurance agent shortly out of high school, and I did it to pay for college, but I did so well, I never looked back."

Aunt Kelly was not helping Tim out. He realized that she was probably using the word 'hot' as a replacement word for successful, but Tim couldn't help but think about how hot Aunt Kelly probably was back then. As hot as she was now, he could only imagine. He also couldn't help but think that buying insurance from an attractive young lady was probably a lot more enjoyable than buying from... anyone else. So, he could certainly see the advantage of being a 'hot young female insurance agent.' Tim discretely adjusted himself to avoid any embarrassment as Kelly continued.

"So, she's working hard, and I'm proud of her. It's hard for me to not be overprotective considering some of the things I experienced back then," Kelly got a far-off kind of look as she spoke. Tim felt his cock rise to attention as he imagined his Aunt Kelly, the age of Holly, getting plowed from behind by a young architect who recently graduated from college and was buying a house and needed some insurance.

Tim's heart pounded in his chest as he quickly thought, 'I hope Aunt Kelly has a hot date for me, I've gotta get laid before I do something stupid.'

"So, Tim, how's the new job?" Kelly broke the silence.

They spoke about Tim's new job, co-workers, lack of girlfriends, transitioning to a new town. Kelly spoke about when she first moved to Coeur d'Alene and empathized with him. They laughed together when Tim told her a story about how his eccentric landlord brought a bunch of cats into a vacated apartment to catch mice for a week before cleaning it up and listing it.

It was around 1:30am when they finally rounded a bend and came to the driveway to Steve and Melanie's house. Tim suddenly felt like he was going home, and he also felt tired and ready for bed. When they pulled up to the house, Steve came out and welcomed them.

"Your mom's asleep, but she told me to tell you that your room is ready, and you know the way, and that you're old enough to put yourself to bed," Steve said after greeting Tim and giving him a hug. "Hi Kelly, thanks for bringing him," Kelly and Steve embraced, and they kissed each other on the cheek. Tim didn't remember them being affectionate like that before.

"It was my pleasure, it was nice reconnecting with my nephew who has become quite the nice young man," Kelly walked over to Tim and gave him a hug, pulling his head down so she could kiss him on the cheek. Tim's on-again-off-again erection made its way back to life when he felt Kelly's tits pressed against him.

"Bye-bye now, I'll see you tomorrow," Kelly said with a wave to both Steve and Tim as she hopped in her car and drove away.

"Feels like I'm home," Tim said as he and Steve made their way inside.

Steve smiled and reached over and mussed Tim's hair, "It's good to have you here my man."

Tim made his way to his bedroom, pulled his clothes off except for his underwear, and fell asleep without unpacking and with little effort.

******

Chapter 3: Overtones of Impropriety

Melanie stood in the doorway staring at her son's morning wood. Her heart pounded and she didn't know what to do. It was protruding from Tim's boxers which was the only thing he happened to be wearing at the moment, and the covers had gotten pushed down so that he was lying exposed on his bed.

Melanie had come to Tim's room to announce that breakfast was ready, but she felt certain that if she woke him standing there, that it could create quite an awkward moment. She admired her son as she gazed at him. He was in good physical condition, and he reminded her of her late husband and Tim's father. Tim had light brown hair that he kept trimmed and styled, he was clean shaven and on his muscular chest he had an attractive bit of hair that covered his chest and trialed down to his naval. Just like his father. His cock was also just like his fathers. It was a good size, neither overly large, nor small by any means. It was well formed and had enough girth to please most women.

Melanie finally tore herself away from the memories and from staring at her son and exited the room. She then knocked loud enough to wake Tim.

"Yeah?" came Tim's reply.

"Breakfast is ready," Melanie shouted through the door.

"Okay thanks a lot mom, I'll be right out."

Melanie went back down to the kitchen where Steve was drinking coffee and working on his computer. She readied a plate of food for Tim and a cup of coffee, setting it down at the table next to Steve.

"You woke him?" Steve asked, seeing the food and coffee. Melanie only drank tea, so he knew it wasn't for her.

"Yeah, he's coming down."

"Poor guy, you could have let him sleep in."

Just then Tim came into the room, "Hi, good morning."

"Timmy, I made breakfast for you," Melanie walked over and gave Tim a big hug. She occasionally called him Timmy, and it was often when she was doing something for him that he was capable of doing himself.

"Thanks mom," Tim sat down to eat.

It was Saturday, so there was no pressure to try to fit any work in. Tim was thinking about going out on the lake, but he wasn't sure if his parents had anything in mind already.

"So, do we have any plans for today?" Tim inquired between bites of food.

Steve looked up from his computer, "Your Aunt Kelly and Holly are coming by in a couple hours and we'll go down and take the boat out on the lake. Do you want to do any fishing?"

"Sure," Tim replied.

"You don't have to; you can just relax too. We'll take some food, and we have beer and wine on the boat," Melanie interjected.

"The fishing gear is on the boat anyway, so whatever you want. I thought we would ride over to town and grab some dinner at The Cedars Floating Restaurant. We can just have a leisurely time till then. The water's getting chilly already, but if you want to take a swim you can do that too," Steve explained to Tim.

Steve's boat was a small 48-foot Yacht, with two bedrooms, a kitchen and relaxation area out of the sun, and the captain's deck with plenty of seating and space. It was a bit much for Lake Coeur d'Alene, but it was always an enjoyable time.

Around 11am Kelly and Holly showed up. Tim was unpacking his suitcases for the weeklong stay, and so he didn't hear them when they arrived. After Tim had finished unpacking, he headed back downstairs and he heard Aunt Kelly and his mom laughing together.

"Kelly! Jesus, watch it."

"Oh, come on, you know you wish you had been there to see it," Kelly teased her sister.

"Even if I did, you know as well as I do that he's got nothing on Steve," Melanie pushed back.

"Speaking of which..." And then Kelly's voice shifted to a whisper that Tim couldn't hear.

"Maybe but Tim is coming with us, so I don't think it's going to happen," Melanie replied flatly.