New Year's Eve Disaster

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Sidechick gets taught a lesson on New Year's Eve.
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DanDraper
DanDraper
1,129 Followers

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

.....

Gemma took one last look at herself in her mirror, happy at what she was seeing. She was wearing a new black sequined mini dress with black kitten-heeled shoes. The dress showed off plenty of her legs and much of her large breasts. She loved how she looked and wished she could stay like this forever. She was 26 and had long blonde hair, a tight body with a great ass, and perfect 34D breasts.

Her tits were fake but nobody could tell when they saw them. Her sugar daddy, Richard, spent a lot of money to make sure they looked and felt as real as possible. He had plenty of fun with them when they fooled around, but she had a lot more fun using them to get other guys into bed with her. Her sugar daddy didn't know she was fooling around with other men; as far as he knew, he was the only man she was sleeping with. It was part of their deal that he would financially take care of her as long as she didn't see other men besides him but she didn't care. She made sure he didn't find out about it, just like Richard made sure his wife didn't know he was fucking a woman he met at a strip club and was now keeping her around a his sidechick.

She was going to see him tonight at his company's New Year's Eve party except that he didn't want her showing up there. Richard was going to be with his family at the party and he didn't want her around to ruin things. But she felt she had no choice but to go and see him; there was a hiccup in their arrangement lately and she needed to see him immediately to make sure it continues.

They hadn't seen each other in weeks. He would still send her money, pay her rent, credit cards and everything else, but he didn't want to see her personally. He said he was too busy these days, but she didn't buy it. She was afraid that he was about to end their arrangement and was just waiting for the right moment to do so. She was worried that would happen sometime after New Year's Day because then all the holidays would be over but also wanted to get it out of the way weeks before Valentine's Day to make things less complicated.

She wasn't in love with Richard, it was purely a financial arrangement between them. She could get another rich man to take care of her, but she didn't want to go through all of that trouble of finding a new one until she was absolutely sure about it. Plus, she liked Richard enough to keep doing this with him. He was a sexy older man with deep pockets and could fuck like a twenty-year-old. She knew one day it might be over between them, but she still wanted to keep him on the hook for as long as possible. Her bank account depended on it.

She put on a coat, left her apartment building and got into the rideshare car that was waiting for her. She fixed up her makeup along the way to make sure she looked perfect. When she arrived at her destination, she gave the driver a $40 cash tip and he was very thankful for it. Richard always gave her plenty of money, so she always gave big cash tips whenever she could.

She flirted with the security guard who recognized her from her past visits when she would meet Richard here after work hours and he let her into the building despite not being on the guest list. She went up to the 13th floor where Richard's company was headquartered and found herself in the middle of a huge party. She was surprised at how big the party was, considering it was just a real estate firm with a lot of stuffy white-collar realtors and other office dwellers. To her surprise, the crowd was big, the music the DJ played was good and everyone was having a good time.

There was a coatroom in the hallway outside of the party where she hung up her coat but still kept her purse. She got to the party and made her way past the guests, ignoring the men who were trying to get her attention. She asked around to see if anyone had seen Richard and a secretary told her where she could find him. She tried to get to that location but was interrupted by one of the male guests, who looked to have been partying too much.

"Whats up, I'm Trent,"" he said.

"Hey," she replied, intentionally not introducing herself.

"Damn, you're fine," he said as he looked her up and down. "Are you the entertainment?"

"Excuse me."

"How much to take that dress off?" He asked.

She was surprised by how candid he was being. She dealt with men like this for a long time before Richard when she used to be a stripper so she was used to it.

"Fuck off, loser," she said and moved around him.

It took her some time, but she finally found him in a far-off corner of the floor where the music wasn't so loud. Richard was a very good-looking for a 60-year-old. He was tall, very fit with salt-pepper hair and had very few wrinkles on his face.

He was talking with a group of people, and by his side was his wife, Sarah, a woman in her late fifties who used to work at the company but was now more focused on running her charities and other philanthropic work. Her shoulder length hair was completely white and she didn't care how old it made her look. Gemma could tell she kept herself in good shape, but not as good-looking as she once used to be. Gemma could see why Richard needed a little something on the side.

"Oh my God, that dress is to die for," said a male voice next to her.

Gemma looked over at a good-looking man standing next to her.

"Excuse me," she said.

"That dress, I love it," he said. "It's like something out of The Great Gatsby."

Gemma recognized the man from pictures she'd seen of him that Richard had shown her. It was Michael, Richard's gay son who was the company's CFO. He looked much like a younger version of his father.

"Thank you. That's what I was going for," she said even though she had no idea what reference he was making.

"Brandon used to love wearing dresses like that, but he could not pull them off as well as you do."

"Thank you," she said. "Is your boyfriend here?"

She didn't care, she just wanted to make small talk as an excuse to stick around until she got Richard's attention.

"No, I found out he was cheating and told him to fuck off," said Michael. "Four years of that relationship down the drain."

"I'm sorry to hear that."

They did a little small talk while she continued to spy on Richard to find a moment to be alone with him. She found out from Michael that he was the one who planned the party, which explained why it was a very extravagant party. Only a gay guy could plan a party like this.

Richard finally noticed her and looked scared. He made an excuse to walk away from his wife and guests and signaled her to follow him. She made an excuse to go to the bathroom and Michael pointed her in the direction of where it was, which was conveniently in the direction that Richard was going. But she barely made it ten feet before she ran into Trent again.

"Hey baby, you're looking for me?"

""I told you to fuck off," she replied.

"How about I give you a tour?" he asked. "Of all the empty offices we can be alone in."

Gemma was amazed at how much of an asshole this Trent was being, it was like he wanted people to hate him. She could tell he was a little high; it may explain his behavior, but it doesn't excuse it.

She walked away from him, but he kept following her.

"Are you going to be around at midnight?" He asked. "Look for me when you need someone to kiss and probably screw your brains out."

"Go away, loser," she said as she continued walking.

She heard a commotion behind her and turned around to see Michael stopping Trent from following her. She could barely hear them, but Michael was arguing with him about his behavior. She was grateful for Michael for stopping that idiot so she could find his father and seduce him.

She found Richard in a dark hallway and signaled to her to follow him into the copy room. As soon as she walked in she tried to kiss Richard but he stopped her.

"You can't be here," he said angrily. "You asked me if you could come and not only did I say no, I specifically told you why it was a bad idea."

"I haven't seen you in weeks and I missed you," she said while giving him puppy dog eyes.

"I told you, I've been busy."

"You're not busy now," she said as she tried to kiss him again.

"Not here. Are you crazy?"

"Crazy for you," she replied.

He couldn't resist and kissed her hard. He held her close and she could feel his dick getting hard in his pants. She let go of the kiss and got down on her knees.

"We can't do this here," he said.

"Sure, we can," she said as she tried to take off his pants. "We've done it in this coat room before, as well as several other places in your office when no one was around."

Richard took a few steps back from her and fixed his pants. Gemma stood back up and gave him an angry look.

"Are you going to end things with me?" she asked.

"No, I promise you, I'm not," he said.

"Then what's going on?"

"I've just been busy, that's all," he said. "I also missed being with you. I think about you all the time."

"You do?" she asked with a big smile.

"Of course I do," he said. "I promise, in a week I'll get in touch with you and I can take you out somewhere nice. But right now, we can't do this. Especially not here."

"I don't think I can wait another week," she said. "Meet me in your office at 11:30, we can fool around just in time for the countdown."

"Are you serious?" he asked. "Can't it just wait another for another day?"

"No, baby. I really need you," she said. "I'm very horny and I need you to fuck me real good."

She didn't really need him that badly. In fact, she had fucked four other guys during his absence. She just wanted to use sex to keep him on the hook. She was sure that when he said he'd get in touch with her in a week, that meant he needed time to end things with her and she wasn't going to have that. As long as she could keep him supporting her, she would do whatever it took to keep him.

"Alright, I'll meet you in my office at 11:30," he said. "But we can't stay too long; I have to get back to my wife before midnight."

"Of course, baby. Despite everything,, I don't want to ruin things with your wife,"" she replied with a fake smile.

"Good," he said looking relieved. "Now let's get back to the party. Have a little fun while you're here and we'll meet in my office later."

"Whatever you say, baby."

They began kissing again, even heavier this time. He grabbed at her tits, and he was glad she wasn't wearing a bra. She asked if he changed his mind about getting a blowjob, but he said he'd get it later in his office.

He left the copy room first, while Gemma stayed behind to fix herself up before heading back to the party. She decided to have a little fun while she waited for her time to meet Richard in his office. She had a few drinks, danced with some people, and found some fun women to hang out with. They asked who she was and just said she was a friend of Michael and did her best to vaguely answer their questions about how they knew each other.

She ran into Trent again who made some more lewd comments to her. She tried to get away, but this time, he grabbed her ass and that pissed her off enough to finally give him a smack in the face.

Trent just laughed. "Damn, you're feisty. I like that."

Gemma just walked away from him and got herself another drink. She looked at her watch and realized it was almost time to meet Richard in his office. She made her way through the guests again, doing her best to avoid Trent and anyone else who noticed her earlier.

The hallway towards Richard's office was empty. As she walked towards his office, the voices and music from the party began to fade away the further down she went. She got to his office and twisted the knob, relieved that it was unlocked. It was dark when she stepped inside and reached out to the wall by the door frame to try to find the light switch. Just as she found the switch, she was startled when she was gently pushed inside the room. The door closed behind them and she heard the intruder lock the door.

"Richard? Is that you?" she asked.

"Who else could it be?" A male voice whispered.

"You startled me."

"Keep your voice down. We're down the hall, but I don't want anybody to hear us."

"Sorry," she whispered back at him.

She tried to find the light switch again, but he stopped her. It was very dark, but there was a little light coming from the closed window shade that allowed her to see his silhouette.

"Keep the lights off," he said to her. "If someone does come down the hallway, I don't want them to know anyone is in here."

"Good idea," she said. "I guess we'll just have to do this in the dark."

She walked up to him and put her arms around his neck and he held her close as they began kissing. She had to stand on her toes as she usually does whenever they kiss, but this time she found herself standing on her toes a little higher than she normally does. It wasn't by much, but it was noticeable; she shrugged it off with the reason that it was because of the type of shoes she was wearing.

The kiss was far more passionate than it normally was; it was more one-sided, and he was being more aggressive with how he was kissing her. Even his tongue felt differently than it normally did and he was pretty much shoving it down her throat. She thought he was just very excited to see her at the party. She didn't like that he was shrugging her off earlier; she understood because his wife was around. But now he was being very aggressive in how he was making out with her. She wasn't complaining, she liked when a man took charge like this, and she let him kiss her the way he wanted.

His right hand went down to her ass and began grabbing at it. Again, she felt something was off with what he was doing; his grip on her ass was a lot firmer than it usually was. He gave her ass a smack so hard that it made her pull away from the kiss.

"Not so hard," she said to him.

"You know you like it," he replied.

He gave her ass another big smack and this time followed up with a big squeeze.

"OW!" she said loudly. "That hurt. I like a good smack on the ass but that was hard enough to leave a mark"

"I'm just having a little fun," he whispered back to her. "And I told you to keep your voice down so no one would hear us."

"Sorry," she said, going back to a quieter volume. "It's hard to keep quiet like this."

"I know a way to keep you quiet," he replied.

He guided her over to where the desk was. Because of the desk's dark color almost matched the darkness of the room, they couldn't see it as much when they bumped into it. There, he leaned back against the desk, and Gemma put her purse on it so she would know where it was later. He made Gemma get down on her knee, practically pushing her down, which she didn't like. She was more than happy to give him a blowjob but she didn't like having to be pushed to her knees like that.

He didn't take his pants off, he just pulled down his zipper and took his dick out of the opening. Gemma spat in her hand a couple of times and began stroking it. His dick felt differently this time; it was the same size but a little thicker than it normally was. She was wondering if she was just misremembering because it had been several weeks since she last did this for him.

"Enough of that, I could jerk myself off if I wanted to," he said. "Open your mouth and suck it."

She wondered why he said it like that. She was going to blow him eventually, but she always stroked his dick first because he said he liked it when she did that. But she did as he asked, opened her mouth, and began sucking on the foreskin as she continued to stroke his shaft. She liked to occasionally do this to tease men a little and then get straight to sucking them off. She had done this for Richard several times before, but this time he grabbed her by the back of the head and pushed her head down on his dick, making her take almost half of it into her mouth.

She began sucking him off and wondering why he was being so forceful like this. He usually just let her suck his dick the way she wanted to and he always enjoyed it. She figured he wanted to do this quickly and get back to the party before anybody noticed he was gone too long, especially Sarah, which was a reasonable concern.

She kept her lips perfectly sealed around the shaft and massaged it a little with her tongue each time she bobbed her head on it. She deep throated him a few times as she did this, but only a few seconds at a time. He had his hand on the back of her head the whole time, guiding her a little as she did this. Soon, he grabbed a chunk of her hair really hard, making her wince in pain. He then pushed her head down harder on his dick, getting as much of it into her mouth as he could. It hit the back of her throat, and he kept it there for several seconds, making Gemma chock on it.

Gemma was having trouble breathing so she pushed back on his legs to give her enough leverage to get his dick out of her mouth. She began coughing and breathing hard, relieved that she was getting some air in her lungs again.

"Not so rough," she said loudly.

"I told you to keep quiet," he said aggressively.

He shoved his dick back into her mouth again and pushed it deeper down her throat. Gemma tried to push back on him like she did before to get his dick out of her throat, but this time he held on to her head tighter so she wouldn't break free. He kept his dick down her throat a lot longer this time, so she could really choke on it. She began hitting his leg with her fist as a signal to get him to stop.

He pulled his dick out of her mouth and she began coughing a lot more and breathing heavier. She wanted to say something, but she was too busy trying to catch her breath to say anything. When she settled down and was about to ask him what was going on with him, he shoved his dick back into her mouth. This time, he used both hands to hold each side of her head as he began roughly face-fucking her. She was starting to get scared about what was happening to her; he had never treated her like this when they were together. They sometimes got rough in bed, but always in a fun way and they made sure nobody got hurt. Now he was practically hate fucking her mouth and she was afraid of how he would fuck her when he was done.

"You like your mouth being fucked like this?" he asked her. "You enjoy being on your knees like this, isn't that right, you little homewrecking slut?"

Richard had never called her that before. He sometimes used slut or whore when they were in bed, but he never called her a homewrecker. Being called this while he was roughly face-fucking her somehow made the whole situation feel worse.

He shoved his dick down her throat one more time, leaving it in much longer this time before finally pulling it out of her mouth. Gemma was relieved that this part was over; she was going to tell him that she had enough as soon as she could breathe normally again. She slowly stood up and before she could say anything, he made her bend over the desk and lifted up her skirt

"I want to go now. I think I've had enough," she said.

"But I haven't had enough," he replied.

He held her down with one hand as he pulled off her panties with the other. He got behind her and without any hesitation, shoved his dick into her. The first thrust into her was painful and she let out a small scream because of it. He told her to keep quiet and began fucking her hard. She had no idea what was happening to her; Richard had never mistreated her like this whenever they got together. It was as if he had no respect for her at all and just wanted to fuck her like she was being punished for something.

"Richard, stop!" she said. "I don't know what's gotten into you, but we need to stop this now."

DanDraper
DanDraper
1,129 Followers
12