Family 'Adult' Halloween Party

Kelly playfully chided Tim for getting distracted and insisted that he needed to fuck her again to regain his focus. By this point, Tim's cum was less than a teaspoon with each subsequent orgasm, and Kelly gladly swallowed it all.

Eight.

Eight orgasms were the total number when Tim called for an Uber to take him home after he and Kelly's first day working on the remodel project.

The next day was far more challenging. Tim had arrived at 7am at Kelly's request. Kelly reminded him that this was Monday, and that there would be others in the office today. Tim and Kelly fucked twice before other employees showed up at around 8:30am and the office opened at 9am.

Tim met Kelly's employees, most of which were new to him, but a couple he had known for many years who had been working with Kelly for close to a decade. Of course, they all wanted to give their opinion on the remodel.

Tim realized that he hadn't seen Holly yet, which surprised him, and worried him. He hadn't seen her since he had barely acknowledged her after filling her mouth with cum after forcefully fucking her throat. His reflection on this still slightly horrified him, and slightly aroused him.

Tim was sitting at Kelly's computer in her office while reflecting on this. He was leaning back in the desk chair when Aunt Kelly walked in. She closed the door behind her as she said in a muted tone, "Uh oh, someone's distracted."

Kelly walked over to Tim and pushed the chair back from the desk. It was a rolling chair, and so it easily wheeled backwards giving Kelly plenty of room get down in front of Tim and fish his cock out of his pants. Tim made no objections verbally or physically as his Aunt Kelly began taking him into her mouth.

*Knock* *Knock* *Knock*

The door to Kelly's office began opening without any response or additional notice. Kelly deftly launched herself backwards to end up under her executive style desk. Tim rolled his chair forward towards the desk and doubled over in the hopes of hiding his cock from view.

Holly walked in. Holly was dressed professionally with a blazer on top of a button up shirt, tucked neatly into her dress slacks. She was wearing heels which brought her close to 6 feet tall which made her impressive, stunning, beautiful, and intimidating simultaneously. When she saw Tim's strange reaction to her entrance, she smirked at him.

"If you want to jerk off in my mom's office, you should lock the door," Holly said flatly as she turned to lock the door herself.

"Oh, right, sure thanks," Tim replied, totally unsure of what to do.

Kelly was still under her desk; Tim was totally unclear as to whether it was a problem for Holly to know what had really been going on or not. Obviously, Kelly knew that it was Holly who had come in, and since Kelly hadn't emerged to make her presence known, Tim felt he should try his best to cover for her.

"You don't need to lock that," Tim said as he stood up.

Holly burst out laughing. When Tim had stood up, his pants fell exposing his boxer-briefs which clung to his hard cock which was clearly outlined for Holly to see.

"Yes... I do..." Holly replied as she took off her blazer and hung it up on the hooks on the back of her mom's door.

"Holly what are you doing?"

"Rescuing you again I suppose," Holly replied with a shrug while she continued to undress, "but this time I want you to cum on my tits, I have a customer coming in in about 15 minutes and the idea of having cum on my tits without him even knowing is turning me on."

Tim's cock strained in his underwear. He broke his frozen disbelief in the hopes of keeping his Aunt Kelly hidden. Tim kicked off his pants and was grateful that he had worn some slip-on shoes which he discarded. Tim proceeded to walk over to Holly, he pulled her topless body into his arms before she could do anything further, as her body met his, he pressed his lips to her and kissed her fully.

Holly seemed both surprised and welcoming as her lips parted and she began making out with Tim. Tim reached up to play with her tits and tease her nipples. Holly moaned into Tim's mouth as they continued kissing.

When they finally pulled back, Holly was genuinely surprised and so was Tim.

"What's gotten into you?" Holly questioned.

"Sorry," came Tim's reply.

"Don't be sorry, I like it. But you barely spoke to me after dinner the other night."

"Sorry," Tim offered again with a shrug.

"It's okay, I just thought you were mad."

"No, I wasn't mad... just a little ashamed I guess."

"Seems like you got over it," Holly pointed out.

"I guess so."

"Good."

With that, Holly dropped to her knees and began blowing Tim. This time, Tim looked down into her eyes while she did it and his hand lovingly caressed her hair and face while she ran her tongue all over his cock, jerking him simultaneously.

"Will you fuck me?" came Holly's question.

Tim responded by helping her stand back up, he undid her pants, and Holly slid them off revealing that she wasn't wearing any panties. Tim could see a glistening between her thighs and knew that she was ready for him. Tim bent Holly over her mother's desk, (and unbeknownst to Holly, over her mother) and slid his cock into her warm inviting depths.

"Oh fuuuuuck, Tim that feels so good, fuck me Tim."

Tim obliged happily as he began fucking Holly with force. What was it about Holly that caused Tim to turn into an animal. He reached up and grabbed her tits, pinching at the nipples and squeezing hard. Holly apparently approved as her moaning increased.

Tim was grateful that he had fucked Aunt Kelly earlier today, as it allowed him to prolong his own orgasm as he pushed Holly closer to hers. Tim looked down watching himself slice into his cousin's hot wet cunt and the view of her pert, sexy, 18-year-old booty had his orgasm growing quickly.

"Ffffffffffuuuuuuuuck..." Holly did her best to contain the scream of orgasm that caused her legs to quiver and (like her mother) goosebumps to cover her skin.

"Holly I'm going to cum," Tim warned in the middle of her orgasm.

Holly fell to her knees; her eyes were still rolled back into her head when Tim fired shots of cum across her tits. As she came back to reality, she smiled up at Tim as she rubbed the cum into her skin.

"Fuck, I needed that," Holly said.

"Me too," Tim replied.

Holly rose and got dressed. Tim sat down in one of the other chairs in the room, wearing only his shirt.

"You should probably lock this when I leave. Mom's going to need a good fucking after that," Holly said without blinking. "I could hear you playing with yourself under the desk mom... Thanks for sharing!"

Tim was stunned.

Holly left with a laugh, and Kelly crept out from under the desk looking bashful and lustful simultaneously.

Tim did lock the door again and proceeded to relieve Aunt Kelly of her sexual frustrations which had been enhanced by being caught by her daughter.

******

Chapter 8: Costume Decisions

Tuesday had arrived, which was the last day for Tim to finish up the remodel project for his Aunt Kelly's office redesign. It was also Halloween, which meant that he would be tasked with going to Steve and Melanie's annual Halloween party.

Tim had never been a person who particularly enjoyed Halloween. By the time he was 12, he never went out to go trick or treating, and he usually just wore a silly mask to any party he was invited to, putting as little effort into it as he could get away with. Melanie knew this about Tim, and so she had set out several costume options for him to pick from.

When Tim woke this morning, he climbed out of bed, and saw the various costumes laid out. A note sat in the middle and said, "Come get me before you say no. xo Mom".

Tim sighed. He wasn't going to get out of dressing up this year. He didn't give the costumes a second look and decided to head down and get a cup of coffee before his mom could pester him about the costumes. When he walked into the kitchen, he saw Steve and Melanie snacking on some fruit with their morning beverages.

"Timmy! Did you see my note?" Melanie asked when she saw Tim walk in.

"I saw it," Tim replied flatly.

Steve started laughing, knowing what was about to happen.

"Great!" Melanie replied without hesitation, "So get some coffee and let's go try them on before you go to Aunt Kelly's office."

The mention of Aunt Kelly's office caused an involuntary twitch and swell in Tim's cock. A swell he knew he couldn't do anything about at the moment which disappointed him greatly and put him in a sour mood.

"Sure mom, let's just do it quickly, I have to get going if I'm going to finish in time."

"Okay honey, let's go right now then."

Tim and his mom went back to his room. She sat on his bed and told him to go try them on in the bathroom. Tim picked up the costumes and groaned as he realized that they all had multiple parts to them, and he couldn't see any masks.

Tim surveyed the pile once he was in the bathroom. 'What the fuck?' Tim thought as he picked up the first costume.

It was a pair of red latex form fitting shorts, red wings that he could slip on through his arms, and a headband with horns on it. Tim left the costumes there and went back out of the bathroom. His mom looked disappointed when Tim arrived.

"What's wrong Timmy?"

"What do you mean what's wrong? I can't wear this stuff. I mean what the hell mom?"

"I thought I told you it was an 'Adult Only' party now."

"Yeah, I remember," Tim replied, "But I didn't realize you meant it like that! I mean come on; I can't wear that stuff."

"Tim, come on, you're an adult now. Please don't embarrass me by being a party pooper. Everyone dresses like that. I can't have you making people feel self-conscious because you won't join the fun. Just give it a try."

"Really mom?" Tim was genuinely torn. He got what she was saying, but he also was not looking forward to parading himself around half naked in front of people he'd known for years, parents of his friends from high school, his parents' business associates and club members. He just couldn't imagine it.

"Okay listen, I'm going to go get Steve, and we'll model our costumes for you first. Just wait here, don't go anywhere!"

Melanie ran out of the room to get Steve and their costumes. Tim sat at his desk dumbfounded. When Melanie and Steve got back, Tim's jaw hit the floor.

Steve was wearing a superman cape with no shirt, and red underwear with no tights underneath and a pair of superman boots. Melanie was wearing a sexy Lois Lane cosplay outfit which was comprised of suspenders coming up from a short skirt that exposed a hint of her ass cheeks, a professional tie that hung down across her exposed belly and a button up shirt that was cut so short that Tim could see Melanie's tits exposed underneath it. There was a hint of her darker nipple area visible which made Tim's mouth water. Melanie tossed a bunch of costumes on the bed. When she did that, her skirt lifted a bit higher to expose more of her flesh, and Steve slapped her ass causing a glorious jiggle that almost gave Tim a heart attack.

"Okay so look, this is what we wore 2 years ago," Melanie began, "And I brought a few more outfits from the last couple years. So go try something on, and while you do that we'll change and show you some more of ours."

Tim was stunned. If he hadn't been fucking Aunt Kelly and his cousin Holly over the past few days, he probably would have objected and refused. But looking at his mom's sexy outfit and wondering what else she might have in store caused Tim to rise from his seat and head into the bathroom to try on one of his outfits.

Tim heard Steve chuckle when Tim closed the bathroom door.

"Later!" *slap*, Tim heard through the door. His cock grew.

Tim had managed to put on the devil costume and was doing his best to hide his cock from view when he heard his mom call out that they were ready. Tim tried to conceal his cock by aiming it down along his leg. He thought it worked okay.

When Tim stepped out of the bathroom, his efforts were immediately subverted. His cock sprang at the view of his mom who was bent over his bed reorganizing the costumes. A green thong between her ass cheeks greeted him which was barely covered as she stood back up by a short green Tinkerbell skirt. When she turned around, Tim got a full view of his mom's tits through the sheer Tinkerbell dress. She had strapped on some wings that stood out behind her. Around her neck was a collar with a leash that Steve was holding as Captain Hook. Captain Hook of course had no shirt, a brilliant hat, and tight form fitting latex shorts with boots. Tim seemed to catch the theme.

Tim's cock had made its way to point upwards, and the extension of which had the head of his cock pointing out of the top of his small red latex shorts. Melanie noticed and gasped. Steve laughed and offered an, "I don't blame you pal," with a slap to his mom's ass again.

"Steve!" Melanie objected.

"What? You have a great ass, babe."

Tim had reached down to cover himself.

"Okay let me have a look," Melanie walked up to Tim to look at the components of his costume making slight adjustments here and there.

"Yeah, I don't think this one will work for obvious reasons," Melanie continued as Tim kept his hand covering his erection, "But I think there's one with some baggier pants that might work better for you."

Tim had noticed the costume that his mom was referring to and so he shook his head in agreement.

"Umm, let's leave this year's costume for a surprise," Melanie offered, and she and Steve gathered their costumes and left the room.

Tim was glad that they left. He elected not to mess with the costumes any further, wanting more than anything to get to the office and to Aunt Kelly.

******

After Tim arrived at his Aunt Kelly's office, he had quickly made it known that he needed to fuck. Kelly obliged immediately.

"That was a little vigorous, even for you, what's up?" Kelly asked while she and Tim got dressed.

Tim's face turned red, and he didn't respond.

"Oh, come on Tim," Aunt Kelly began, "You're fucking your aunt for goodness' sake. Don't get embarrassed now."

Tim confessed about what had happened with Melanie and Steve that morning.

"Ohhhh," Kelly responded knowingly, "Yeah that Tinkerbell costume was quite the head turner. Her ass got a lot of attention that night."

Hearing Kelly talk about her sister and Tim's mom like that caused Tim's cock to swell up again. He hadn't put his pants back on yet, and Kelly noticed. She reached over and stopped Tim from getting dressed further, gripping his cock through his underwear.

"Did you know that Tinkerbell is a bigger cock-slut than I am?" Kelly asked rhetorically with an intensity that gripped Tim's attention.

Tim looked into Kelly's eyes and found no deception in them.

"Tinkerbell likes getting her pussy stuffed while her mouth is filled with a big cock while Captain Hook whips her ass," Kelly continued, "Every time Tinkerbell takes a cumshot, a fairy gets her wings I hear."

Tim couldn't help but imagine his mom getting fucked while sucking a cock. Kelly's description seemed to indicate that Steve wasn't either of the cocks in the picture she was painting. Tim was fully hard at this point and Kelly continued to jerk him in his underwear while she spoke.

"Imagine Tinkerbell getting gangbanged by the lost boys, and that will about get you there," Kelly continued as she jerked Tim more and more urgently, "Of course Wendy got jealous and took Captain Hook for herself."

Tim imagined his Aunt Kelly getting fucked by Steve while his mom got gangbanged. Tim closed his eyes while Kelly continued jerking him and pulled the memory of his mom's ass and pussy barely covered by the green thong. He imagined himself pulling it to the side and fucking his mother's pussy while Steve cheered him on.

"Oh fuck..." Tim said aloud. Kelly pulled his cock out of his underwear and took him in her mouth right as he started unloading his balls. Kelly swallowed his cum and then stuffed his now spent cock back into his underwear and looked at Tim seriously.

"You need a good costume."

"What? Oh yeah, mom picked some for me."

"No, I have one for you. I'll take you home later and we can pick it up."

"Sure," was all Tim offered.

Tim finished up the remodel buildout for his Aunt Kelly. She was thrilled and told the office about her plans to get the remodel underway. Everyone was excited, and Tim was genuinely happy to have helped. The sex made for more than enough payment, but he also felt good about the work by itself.

Tim helped Kelly close the office and they went back to her place. Tim tried to get in some extra fun with her, but she told him to wait and that it would be worth it. The costume Kelly picked out for Tim was perfect. It was a surgeon costume. No shirt, baggy (thankfully) scrubs, a blue mask, and a surgeon cap. Tim was grateful for the face covering, he wasn't sure who would be there tonight, and he was hoping to avoid too much embarrassment.

"No underwear, right?" Kelly shouted from the bathroom into her room where Tim waited to see her costume revealed.

"Free as a bird," Tim shouted back.

Shortly after, Kelly stepped into the frame of the doorway and Tim's heart stopped.

"Doctor, do you need any assistance? Oh, did you drop this?" Kelly asked playfully as she turned around and bent over to pick up something Tim couldn't see.

Kelly was wearing a short skirt old-school nurse costume with a collar and a deep plunge that went between her breasts and allowed the swell of her breasts to find their way into view. The skirt barely covered her behind, and when she turned around and bent over, her mound peaked out from between her legs and was easily visible as the skirt rode up.

Tim's cock was hard as a rock.

Tim and Kelly heard the front door of the house open. Holly had arrived.

"Go see if Holly wants to carpool while I finish my makeup," Kelly said. Before Tim could leave the room, Kelly walked over and stopped him, she reached down into his pants to grip his hard cock.

Tim stopped, hopeful with anticipation.

"Look, but don't touch," Kelly slapped him on the butt as he went to find Holly.

******

"Nice costume!" Holly remarked when Tim walked into the kitchen where Holly was getting a glass of water.

"Thanks," Tim replied, "Aunt Kelly wants to know if you want to ride with us."

"Sure, that's perfect," Holly replied, "I just have to go get changed."

Holly, ever provocative, stripped off her shirt there in the kitchen, revealing her toned abs, and sexy lacy bra covered tits. Tim marveled at her.

About 15 minutes later, Holly pulled another showstopper with her costume which could best be described as an Arabian princess costume. Think Jasmine, with a short skirt and thong instead of baggy pants.

"What do you think?" Holly said as she did a twirl for Tim in the kitchen.

"My cock says hello," Tim replied.

"Oooo, so forward now. My, my, haven't you changed in a few days," Holly teased as she walked over and felt up Tim's cock in his scrubs.

"I said no touching!" Kelly reminded Tim as she walked into the room.

"I'm not the one touching!" Tim countered.

Kelly and Holly both laughed together, and Tim realized that he had grabbed Holly's ass without even realizing it.

"Fine, how am I supposed to keep cool with the two of you looking like this?"

"Just wait, it'll be worth it," Kelly reminded him.

'It better,' thought Tim. He would have happily taken them both right now and he couldn't have imagined a better outcome.

******

Chapter 9: Party Time

When Tim, Kelly and Holly arrived at Steve and Melanie's house the party was already in full swing. There were people everywhere. Pole dancers, firemen, policemen and women, playboy bunnies, cat women, cowboys, cowgirls, cheerleaders, devils, various fantasy characters, sports figures, and more.