Family Business Ch. 01

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Santa role leads to amazing time with mom.
10.6k words
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Part 1 of the 6 part series

Updated 10/29/2022
Created 12/09/2004
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jt123
jt123
2,746 Followers

The annual company Christmas party had been a blast, as usual. It seemed like everyone at the company buckled down and worked like dogs the whole year and then all the accumulated stress and steam from the year was released in this one night of wild partying. During this one night every employee partied their ass off and genuinely had fun.

John Sampson, the company's owner, never failed to pull out the stops for the Christmas party. He gave all of his employees a paid vacation between Christmas and New Year's and tried to treat them right through the rest of the year. In return, his employees were loyal and worked very hard for him.

At his annual Christmas party John always provided the finest food and the best drinks and made sure that everything was free. This year he decided to hold the party at a local hotel to make sure everyone could party as hard as they wanted and not have to worry about driving home. To the huge applause of the group, he started the party by announcing that the hotel rooms would be on him so everyone should drink up.

It seemed everyone at the party took his advice and things quickly became rowdy. Mike Sampson, John's son, breathed a heavy sigh as he looked at his watch and realized it was time to keep his promise to his dad. Up until now he had been joining the fun of the party, but he was about to sneak into the back room and put on the old Santa costume that his dad loved to drag out at this party. Mike went to the room, slowly put on the costume, and waited for his dad to come and get him.

Dan, the guy who usually volunteered to be Santa, couldn't make the party at the last minute. A few hours before the party John pulled his son aside and asked him to play Santa for the night. Mike had no desire to do it but his dad made it clear it would mean a lot to him and so Mike eventually gave in and agreed.

John had made it a habit of having Santa give gifts to each employee on behalf of the company. With the number of employees attending, this ritual often took a long time and Mike wasn't looking forward to it. He would much rather be drinking and living it up than playing the jolly old fat man to all his co-workers.

His dad seemed genuinely pleased with Mike's appearance and was very excited, as usual, to start the whole Santa routine. Everyone cheered for Santa as Mike walked toward the chair set up at the head of the room. As he made his way up to the chair several of his co-workers made comments to him as if they thought it was still Dan under the costume. "Looking good Dan," he heard someone shout as he settled into the chair.

The way his dad always set this up was that Santa would stay in his chair and the various employees would come up one by one. His dad had given him a big list with everyone's name on it, so when they came up Mike was supposed to check the list and give them the appropriate gift. John always went out of his way to try and personalize his gifts as much as he could.

For the next hour or so Mike greeted a near constant stream of his friends and co-workers. One or two seemed to figure out it wasn't Dan under the costume but most still acted as if they thought it was Dan. Some even said, "Thanks, Dan," when they left.


John had started this company many years ago and it was still largely a family run business. In addition to Mike, his three sisters and his mom all worked there. His youngest sister, Nancy, was 20 years old and still in college. She had just started working in the office as an intern around her class schedule. Mary was his other younger sister and at 23 she had graduated from college a couple of years ago and had been working full time ever since.

Mike was now 24 and had been working for the company since he was about halfway through college. He loved the work and was clearly on the fast track, having already received a few promotions. Some complained it was only because he was the boss' son but most knew it was because he really knew his stuff.

His other sister, Lily, was 26 and also was on the fast track within the company. She had earned a well-deserved reputation as a tough businesswoman and most around the office thought she was a cold-hearted bitch. Mike knew Lily had a softer side and that she could be very fun and even a little wild when she let her guard down. She liked to party just as hard as she worked, but she didn't often show that side to her co-workers.

Leslie, Mike's mom, had a very high-ranking position in the company that she earned through years of hard work. She had never gone to college but picked up the business quickly and had become very good at what she did. Mike really admired his mom. She seemed to be one of those "super women" who somehow managed to have a career, raise a family, and keep herself in great shape. She worked out religiously and either ran or lifted weights every morning. She was just about to turn 50 but looked more like a 35-year-old. Mike only hoped to be that organized and in shape when he was her age.

As the night continued it seemed that, for some reason, tonight's party was getting even more wild than usual. The drinks were flowing freely, as usual, and the dance floor was becoming more and more crowded as the band continued its stream of upbeat dance music. The dancing had started relatively mild, but there were now several individuals and couples whose dancing had become quite sexy and obviously teasing.

Mike noticed that both Nancy and Mary were out on the dance floor living it up. Both shared his mom's natural beauty and both were causing quite a scene on the dance floor with their sexy, drunken dancing and other teasing antics.

More of his Santa duties called and Mike lost track of what was happening in the rest of the room for a while. When he had another break he saw that some of the guests had started leaving and so it was now easier for Mike to locate his family as he surveyed the room.

His dad was happily chatting with a large group of people in one corner. Mike scanned the room and was surprised to see that his mom and Lily had joined in the loud, wild group that Nancy and Mary had been hanging out with all night.

This group was made up of some of the youngest, best looking women at the company and all of them had been partying hard all night. Mike felt his cock tingle slightly as a couple of the women from this group made their way up to him. Most of the other employees had simply stood next to Mike as they received their gifts, but Mike was happily surprised when Victoria, a tall blonde with killer legs, climbed right on his lap and wrapped her arms around his neck.

She flirted openly with him and caused his cock to jump when she teasingly asked him if any of her naughty acts in the past year disqualified her for a present. He tried to get her to admit to some of the naughty acts but she wouldn't. Despite that Mike was very aware of her squirming and wriggling on his lap and had to concentrate to keep his cock from getting hard.

One by one the group of attractive women followed Victoria's lead and climbed onto his lap. Mike felt a little odd when his sister Mary approached him and took a seat on his lap. He didn't say anything because he didn't want to blow his cover. So far nobody in this group had recognized him and he liked being able to stay anonymous while they flirted with him.

Mary didn't act as openly flirtatious as Victoria or the others but he was still very aware of her hips doing a sexy little wiggle on his lap. He didn't want to get excited but he couldn't help it. He felt his cock twitch at the forbidden thrill of having his cute, drunken sister wriggling on his lap.

A short while later Nancy took her turn. To Mike's surprise Nancy was more flirtatious than any of the others. She talked in a sexy, teasing tone and very openly began grinding her ass back and forth on his lap. Before she got up she planted a teasing little kiss on his lips, and he overheard her telling the others that Santa seemed to be having a good time. He wondered if she had felt his stiff cock pushing against her ass.

Next up was his mom. He took a deep breath to regain control of his cock as she stepped up to his chair. After all, this was his mom and he couldn't allow his cock to do his thinking for him.

"Hey Santa," Leslie purred as she slithered onto his lap.

"Hi," Mike replied trying to mask the sound of his voice so she wouldn't recognize him. She was clearly drunk and didn't give any indication that she recognized him.

"So tell me Santa, have I been naughty or nice this year?" Something in his mom's voice was decidedly teasing and Mike suddenly became very aware of her squirming playfully on his lap. Against his own will he felt his cock spring to life and grow stiff in his pants.

"Mmmmm, Santa," Leslie cooed softly into his ear, "it feels like you're a naughty boy." He stared mutely at his mom as she slipped her hand inside his jacket and added, "Come up a little later and I'll have something really naughty and nice to give you." She gave his lap one last sexy wiggle and leaned close to his ear as she whispered, "Don't keep me waiting Dan."

Mike stared in complete shock at his mom as she slipped off his lap and walked away from him. She turned around and gave him a sly smile and sexy wink before she returned to the others.

Lily was the last person to take her turn on his lap and although she wasn't as flirtatious as the others Mike's cock was fully erect the whole time as a consequence of what had just happened. She squirmed knowingly on his lap and Mike had no doubt that she could feel his cock. Lily talked to him some and he presented her with her gift before she left, but the whole time his mind was elsewhere.

He was still trying to wrap his brain around what his mom had said and done. Clearly she thought he was Dan but Mike still wrestled with what the encounter meant. From her actions it seemed clear she and Dan were not strangers. Mike realized that his mom was cheating on his dad and possibly had been for a while.

Finally his dad made an announcement that Santa had to leave and that anyone else who hadn't yet visited him needed to now. Nobody stepped forward so John leaned down to Mike and said, "Thanks, son. I appreciate you doing this." Mike quickly slipped out of the chair and walked out of the room with a brief glance over at his mom. She was caught up in a conversation and didn't look back at him.

Once back in the changing room Mike reached into his coat and pulled out a magnetic card room key. This was what his mom had left behind when she reached into his coat. The card had a number written in his mom's handwriting. Mike turned the card over and over in his hand as he stared at it.

Had his dad seen the way his mom and sisters made their teasing visits to Santa? A few times Mike had frantically searched the crowd for signs of his dad but, thankfully, his dad had been busy playing host the whole time and hadn't seen any of what had happened.

Shit, Mike thought, it was bad enough that he had allowed himself to get a little excited about his drunken sisters flirting and teasing, but how could he accept his reaction to his mom? Sure she had acted very sexually and had obviously been coming on to him, but she was his mom and he wasn't supposed to feel that way.

Still, the brief encounter allowed him to see a side of his mom that he had never thought about before. Thinking he was Dan, his mom had revealed a sexy, teasing, flirtatious side that Mike didn't know she had. What other secrets had she been keeping?

He returned to the party after getting back in his own clothes and looked around to see that the room was a bit emptier. His dad was still busy playing the host and laughing it up with a group of older guys. He found Mary who greeted him with a smile and asked where he had been hiding all night.

"Oh, I've been floating around," he replied. They made some small talk for a while before Mike looked around for his mom and realized he didn't see her. "Where's mom?" he asked Mary.

"Oh, she said she was tired and headed upstairs a few minutes ago," Mary said. "She said she wouldn't be back down tonight." That news made Mike's stomach knot. What he knew that Mary didn't was that his mom had gone upstairs to fuck Dan silly. His mind flashed back to the way she had flirted with Santa and the way it had made him feel in spite of himself.

Mary turned back to the rest of the group and resumed talking. Mike looked around the room and reached into his pocket feeling for the key that his mom had stuffed into Santa's jacket. He wandered out into the quiet hallway outside the banquet room to try and clear his mind. He stood there for a few minutes thinking about what had happened as he continued fondling the key card in his pocket.

Before he realized he had started moving, he found himself standing in front of the elevators. He hadn't pressed the button but when the door opened and the couple that had pressed the button stepped in he followed them. He didn't need to look at the key in his pocket to remember the number written on it was 759. That number had been burned into his mind from the moment he first looked at it. In a daze he pushed the button for the seventh floor.

The other couple exited on the 5th floor and Mike stood in silence as the elevator glided up the remaining two floors to number 7. The doors smoothly opened and Mike stepped out. He almost jumped back in the elevator but the doors closed before he could. He stood in the foyer outside the elevators still fumbling with the key in his pocket.

He wandered down toward door 759 trying to figure out what exactly he was going to do. Surely he couldn't go inside the room. His mom was clearly expecting Dan and having her own son appear would certainly break the mood.

Besides, Mike was troubled a little by why he cared about "the mood". Sure, he had always known his mom was great looking for her age and his friends in high school and college never missed an opportunity to tease him about his hot mom. Aside from that, however, he had never thought of her sexually before.

For some reason simply the way she had teased him and provoked his cock into getting hard before telling him she knew he was hard had really affected him. The idea of his mom as a sex kitten made his heart race and his stomach knot. He knew that she didn't know it was him under the Santa costume but still hearing her invite him up to the room to fuck had possibly been the singularly hottest thing he had ever heard. Maybe it was true what that old psychologist said about every son secretly wanting to fuck their mom.

Mike was now standing directly in front of room 759 staring at the numbers on the door. He knew he couldn't go in but was still compelled to stand there. The vaguely drunk, very horny part of him tried to convince him to just go in and see what would happen, but he couldn't see any way that would turn out well. He could just picture it in his mind. "Hi mom, it was really me playing Santa instead of Dan." "Oh, that's OK dear, why don't we fuck anyway?"

He began to picture what his mom might be doing on the other side of the door and his cock strained hard against his pants. Then, suddenly, a group exited the elevators and came down the hall. Mike hurriedly turned and began walking away from them not wanting to be seen simply loitering in the hall.

Somehow the noise and surprise of the group's arrival broke the spell door 759 had on him and Mike made his way down to the 4th floor where his room was located. He quickly went inside and immediately sat on the bed and removed his pants. He took hold of his cock and began to slowly stroke it as he thought about his mom.

He envisioned her waiting on the other side of the door where he had been standing. In his mind she waited in revealing lingerie. He wondered what she might do when she realized Dan wasn't coming and, for the first time in his life, he stroked himself while actively thinking of his mother in a sexual way. He imagined her playing with herself and tried to picture what her hands would look like caressing her tits or teasing her clit. He wondered if she was a screamer or if she would just cum with a soft moan.

When he was on the verge of cumming he changed the scene in his mind and pictured himself there with her. In his fantasy he entered the room and they had started fucking just as if she had always been expecting him. He got as far as pulling off her top and bending down to suck her hard nipple into his mouth before he groaned and began to cum all over the towel he had grabbed from the bathroom.

After cleaning himself up Mike lay back on the bed and again tried to make sense of everything. After now cumming he found that he felt a little silly and embarrassed about how he had reacted to his mom. Now it was the fact that she had been cheating on his dad that really struck him. He finally went to sleep that night wondering if he should confront her with his knowledge.

Christmas was two days away and Mike decided to not do anything before the holiday. The whole family always gathered at his parent's house for a big meal and a gift exchange on Christmas Eve and then they all stayed overnight and spent Christmas day together. Whatever he decided to do he knew that right before such a family day was no time to bring up this subject.

Mike returned to his apartment the next morning and tried to go back to his normal routine. Unfortunately, despite his efforts his mind was filled with thoughts and ideas and feelings that could not be called normal. In addition to his mom he also reflected on how each of his sisters had felt on his lap and how each of them had teased him, especially Nancy. He was feeling some very unbrotherly urges and couldn't get the thoughts out of his head.

It was true that he had sometimes jerked off to fantasies of his sisters while growing up, but those seemed like childish follies compared to this. What he felt now was a very adult, very strong desire he couldn't shake.

Despite being the least flirtatious, the sister that most stuck in Mike's mind and kept appearing in his thoughts was Lily. It was obvious that she had felt his hard on as she sat on his lap. Something about the way it felt as his cock pressed against her and the subtle way she reacted to it intrigued him. He didn't know why but he guessed she would be an absolute animal in bed.

Still, his mother dominated his thoughts and impure fantasies right up to the point when he was getting ready to leave his place on Christmas Eve. He still didn't know how to feel about having these feelings about his mom or his sisters so he tried to simply push them out of his mind as he drove over to the house where he grew up.

He was one of the last to arrive and found the house full of good cheer. He hugged and kissed his sisters and his mom and gave his dad a big hug also. All through the meal the family talked happily and enjoyed being together.

They stayed up late talking and watching Christmas movies on TV. At one point Mike found himself alone in the kitchen with his mom while the others all were in the living room engrossed in 'It's a Wonderful Life'.

"I'm glad we have this chance to talk," Leslie said before adding, "lets move over here so we don't bother the others." She led him to one of the corners of the room farthest and the most secluded from the living room.

"What's up?" Mike asked even as he felt his stomach flutter as if it already knew what was about to be said.

"Your dad mentioned to me yesterday that Dan didn't make the holiday party the other night. He said that you were great as the stand in Santa." Leslie stopped and seemed to let those words hang in the air for emphasis. Then she added, "So I guess you've already figured out about me and Dan."

jt123
jt123
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