Jessica Ch. 05

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Jessica is pushed to the limits at Jay's party.
5.4k words
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Part 5 of the 8 part series

Updated 10/13/2022
Created 08/09/2002
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damonX
damonX
2,997 Followers

Chapter 5: The Party

Jessica trembled with anticipation as she rolled the fishnet stockings onto her freshly shaven legs. Taking a pair of high black pumps, she bent over and slipped them onto her feet. She was beginning to get a pretty good idea of what Jay had in mind for her that night as she inspected the maid's outfit he had bought for her. It was black and white with a criss-crossing pattern down the front, that slightly exposed her breasts. When she put the thing on, she noticed that the skirt barely came down to her top thigh. To finish off the look, she placed the maid's hat on her head, careful not to mess her hair.

"You look beautiful," Jay said with a grin as Jessica came out of the bedroom.

"Thank you," she said.

Compliments from Jay still gave her butterflies inside.

"So what exactly are you wanting me to do at this party tonight?" she asked.

"You're going to be a maid. You'll do what ever I or my guests tell you to do."

"Really?"

"Yes. You will also be serving drinks."

"Serving drinks?"

"That's right. What do you expect? You're a maid."

Jessica was a little miffed. She never thought she would be serving drinks, but she would do anything for Jay.

"I see you took left your engagement ring on," he stated.

"Yes," she said. "Do you want me to take it off."

"No. I want everyone to know what kind of slut you are."

Jessica was really starting to love hearing those words. She was becoming a slut. And she loved it! Jay stood up and walked over to her. She looked up at him adoringly, as he made his way over. He then leaned down and kissed her gently on the lips. Jessica closed her eyes and opened her mouth accepting his kiss with passion.

* * * * *

About twenty minutes later the first guests arrived.

"Jessica! Nice to see you again," Zack said as he handed her his coat.

"Likewise," she replied with a sexy smile. She couldn't help but get turned on when she though about the time she had spent with Zack, Jay and Angela just a day before. Zack was accompanied by a young looking woman with dirty blonde hair and piercing blue eyes. He introduced her as "Amy". She was dressed in a cute little blue dress with matching shoes. As they sat down, there was another knock at the door.

Over the next hour many people began showing up. Most were well dressed and attractive with less than a few exceptions. There were couples and single men and women, all seeming to be friends of Jay. Jessica was so busy, meeting new guests and fetching drinks, that she hardly noticed the large hotel suite fill with people. As the night wore on, and the guests consumed more and more alcohol a few became more and more brazen. The men would grope her tits or slip a hand under her skirt as she made her way through the room. There was even more than a few comments shouted her way. Soon Jay started up a card game in the main room, that Jessica though was sure to be trouble.

"Hey baby!" she heard someone say.

She turned around and saw a very large man sitting in an armchair with a glass in his hand.

"Why don't you come over here and keep me company."

He was very intimidating, and Jessica was reluctant to go to him, although she remembered Jay's orders earlier in the evening. She had to do whatever the guests said.

He smiled as she made her way over and patted his thigh.

"Why don't you have a seat?" he said, prompting her over.

Jessica tried to keep her skirt from riding up as she climbed up into his lap. As she sat down his hand immediately went to her ass and gave it a feel with his large hand. She could feel his hard cock through his pants as he continued to feel her up.

"Let's just see what you have under here," he said, sliding his hand under her skirt.

She felt strange, letting him touch her with so many people around. She felt as though everyone was watching her.

"Oooo," he whispered as his hand touched her bare pussy. "No panties! You must be a fun girl."

Jessica remained silent as he slipped a finger inside her. His thumb found her clit and rubbed it as he finger fucked her. Jessica closed her eyes and the room faded away as she shifted her ass around. Her juices began to flow under his touch as she started to get turned on. When she opened her eyes she could see Zack's friend Amy smiling at her from across the room.

"Maybe this will turn out to be a good night after all," Jessica thought to herself as the man under her continued his invasion of her pussy.

"Jessica!" she heard Jay shout from the other room. "Come here!"

She pulled herself from the man's lap and gave him an apologetic smirk as she walked away.

When she entered the room she was surprised to see her image on the large television set. It was the video of her, Jay, Zack and Angela from the other night. She was mortified to see everyone watching her get fucked. Jay was seated at the table with three other men playing cards and watching the television.

"Okay guys, here's the deal," he said. "The winner of the next hand gets to do whatever he wants with Jessica here."

Jess wasn't the least bit surprised. She knew something like this was bound to happen. As the men played, she looked over them. They were all reasonably good looking, so she wasn't dreading spending time with any of them. After a few minutes a winner emerged. He was a man of about thirty years old wearing a Hawaiian shirt.

"Fuck yeah!" he yelled, pulling his chair out from the table. Jessica could see that he was already quite drunk.

"Well I guess I'm all yours," she said, walking over to him.

"You got that right baby!" he said, unzipping his pants.

"Should we go to the bedroom?"

"No fucking way! I want this slut to suck my cock right here!"

With that, he pulled his dick out of his pants.

"Get on it baby!" he said leaning back.

Jessica had done a lot of new things over the past few days, but never with an audience like this. She felt a little strange as she dropped to her knees and inched her way over to the man. Taking his dick in her hand she began to run her tongue over his shaft.

"Don't just lick it. Suck the fucking thing!"

The man's words hurt a little, but Jessica knew that he was drunk. She obeyed, taking his cock deep into her mouth.

"Yeah, that's it. Suck it baby!"

Jessica felt a hand grab her ass as she continued to bob her head up and down on his dick. She was stroking him as well, pumping her hand in conjunction with her busy lips and tongue. The crowd was cheering and the man was muttering obscenities at her as she sucked him. She locked her lips around his dick and began to stroke faster. Then to her surprise he pushed her face away from his cock.

"Jerk me off on your face!"

Jessica did as she was told, holding her pretty face in close to his dick as she continued to stroke him.

"Oh yeah. That's it. Fuck. Fuuuucccckkkk!"

Jessica closed her eyes as her face was splattered with the man's cum. The crowd went wild as the sticky fluid dripped down her cheeks. She then sat back as the man put his dick back in his pants.

"Thanks," he said. "Maybe later I'll come back for some more."

Jessica just smiled as she got up and made her way to the bathroom to clean herself up.

"Damn that guy had a lot of cum.," she said to herself as she wiped the slimy mess from her face. She then reapplied her makeup and walked back out into the party.

She scanned the room for Zack, hoping to find someone to talk to.

"Hello Jessica!"

She spun around to see Pete standing before her. She silently cursed. She was in no mood to deal with the rude man. On his arm was a trashy looking blonde who looked as if she was high on something. She was dressed in a tight black leather miniskirt, and could barely stand on her own.

"What a slut," Jess thought to herself. She then remembered the way she herself was dressed, and realized the woman must be thinking the same thing about her.

"This is Candy," Pete said, introducing the two women.

"Charmed." Jessica said dryly. Her eyes roamed the room, looking for Zack to save her from the situation.

"Petey," the woman said in a slurred voice. "Can you get me a drink?"

"I'll give you something better than that," he responded, ushering her towards the bedroom.

As he walked away, he turned and smiled a Jessica.

"Don't go anywhere Jess. You and I are going to have some fun tonight."

Jessica managed a smile, although she despised the thought of doing anything with the obnoxious asshole. She then went back to serving drinks to the guests.

"Having fun?"

Jessica smiled as she turned to see Zack's companion, Amy, leaning up against a wall. She was smiling, stirring her drink with her finger seductively. She then took the wet finger and sucked it off.

"Where's Zack?" Jessica asked, suddenly feeling quite uncomfortable.

"Oh, he just went to talk with Jay."

Amy started walking towards Jessica.

"You know," she began. "You make a very sexy maid."

"Thank you."

"So you're supposed to "entertain" the guests?

"Uhh, Yeah. I guess so."

"Good. Meet me in the bathroom in five minutes."

Without another word the woman turned and walked off, leaving Jessica standing alone holding a tray of drinks. She quickly distributed the drinks and went to the bathroom. Amy was waiting for her inside.

"Nice of you to make time for me," she said before walking over and kissing Jessica fully on the lips.

Jessica melted at the woman's touch, and opened her mouth to allow their tongues to meet. Amy's hands slid up Jessica's body as she moaned into her mouth. Her soft fingers slid over her smooth skin, under her skirt. Amy kissed her way along Jessica's face, down to her neck, nibbling it gently. She then slowly lowered herself down to her knees, and planted a soft kiss on the inside of her knee. Jessica let out a deep breath as Amy kissed her again, this time a little farther up her leg. Jessica then watched as Amy's head disappeared under her skirt. She could feel her hot breath on her bare pussy, and put her hand on the edge of the sink to brace herself. She almost fainted with pleasure as Amy's soft feminine mouth made contact with her swollen pussy lips. She licked and nibbled, before sucking gently on Jessica's clit. As she lightly grazed her asshole with her finger, she slid another finger up her tight pussy. It took all of thirty seconds for Jessica to reach climax. She was so lost in her orgasm she hardly noticed the bathroom door open and then close again.

"You naughty girls. Are you having fun without me?"

"Zack!"

Zack smiled as he made his way over and gave Jessica a deep kiss, reaching up to grope her breast.

"Are you enjoying my new girlfriend?" he asked.

"Oh yes!"

Zack bent down and kissed Amy, running a hand up Jessica's leg. Amy then broke away and moved around behind her. Zack immediately replaced his girlfriend, thrusting his tongue into Jessica's tight wet pussy. As Jessica moaned, Amy placed a hand on her back and gently bent her over. Spreading her ass cheeks, Amy started rimming Jessica's asshole as Zack continued eating her pussy. Her nimble tongue traveled up and down Jessica's crack before nestling into her puckered rosebud. Jessica was moaning uncontrollably, while getting eaten from both sides.

Zack then stood up and began to take his pants off, while Amy continued to probe Jessica's butt hole with her tongue. Jessica's mouth watered at the sight of his gorgeous cock. At that moment she wanted nothing more than to take that thing into her mouth, but Amy had other ideas.

"Now it's your turn," she said, pulling up her dress and laying back on the floor.

Jessica turned and knelt down between her legs. She lowered her head and gave Amy's clit a few quick licks, teasing the young woman with her tongue. Zack walked over and lowered his dick down into Amy's waiting mouth. Jessica looked up to see his large cock sliding into her hot little mouth as she played with his balls. Jess went back to eating her newfound friend, running her tongue down her wet slit all the way to her tight anus, which was soaked with her pussy juices. Amy was moaning around Zack's fat cock as Jessica continued her oral assault on her cunt. Soon her moans increased to a loud scream that was muffled by Zack's dick in her mouth. Jessica smiled to herself. She was actually giving another woman an orgasm!

Then, almost in sync with Amy's climax, Zack shuddered and unloaded his balls into her greedy little mouth. Jessica could see his white fluid spilling from her mouth as she attempted to swallow it all down. As soon as he pulled his dick free, Jess covered her mouth with a long, wet kiss, tasting Zack's delicious cum.

The three then fixed themselves and walked back out into the party. Amy gave a quick thank you before heading of into the crowded room.

"There you are!" Pete said, taking Jessica by the arm. "Let's go have some fun."

Jessica silently cursed.

"Come on! Don't get frigid on me now baby!"

He guided her into the bedroom and closed the door. Jessica could see his "friend" Candy lying facedown on the bed, with her skirt pushed up over her ass. She was unmoving and appeared to have cum all over her ass. The white fluid was covering her cheeks and dripping down her crack.

"Is she okay?" Jessica asked.

"She's fine. She just had a little too much to drink. Now get on the bed."

"You know, I think Jay wants me to be out serving the guests so I..."

"I don't think so!" he snapped, cutting her off. "You're mine! Now get on the bed."

Jessica restrained herself as she climbed onto the bed with the unconscious girl. Pete sat down next to her and looked over at Candy's unmoving body.

"Oh look. Candy's all messy. You had better clean her up slut."

"Pete, I don't want..."

"Do it you little whore!"

Jessica knew it was futile to argue, and so leaned over and licked up the first drop of cum. Her mouth traveled over Candy's ass cheeks, sucking up the stray splattering of jism.

"That's it you little dirty bitch," Pete said. "Get it all now."

Jessica noticed that Pete had taken his cock out and was stroking it slowly as he watched her lap up his cum from Candy's ass. Her tongue finished clearing her cheeks of the white fluid, then dipped down between. She pulled her cheeks apart and ran her tongue up the unconscious girls ass crack, licking at the cum she found there. Of all the things Jessica has experienced this was by far the most nasty. She felt like the dirtiest slut in the world.

As she continued, Pete began stroking her pussy, pushing his fingers deep inside her. Jessica could see a tiny rivulet of cum trickling from Candy's ass, and so poked her tongue into her tight hole tasting more of Pete's nasty juices.

"That's it! Lick that ass, you dirty fucking slut!"

Pete sat up and pulled Jessica's hips back to him. She could feel the head of his cock stretching her pussy lips as he entered her. He slammed into her, pushing her face into Candy's ass.

"Yeah! Suck my cum from her ass, then go home to your sweet little husband, whore!"

Pete's hands were grasping Jessica's thighs, as his cock slid forcefully into her tight, wet pussy. The sounds of the party were drowned out by the sounds of skin slapping against skin, as his hips made repeated contact against her ass. Jessica pushed Candy's legs apart and lowered her face to eat the cum she found there.

Slap!! Pete brought his hand down on her ass. Jessica bucked her head back as he spanked her hard. He then grabbed a handful of her hair and yanked her head towards him.

"Jay's not here now!" he said. "That sweet little ass of yours is all mine tonight!!"

Jessica gritted her teeth and looked back at him.

"Do it then! Fuck my ass! Show me what you've got!"

Pete pulled his dick from her cunt as Jessica began to lubricate her anus with her saliva and pussy juices. As much as she despised Pete, she realized that if he was going to have his way with her, she might as well make the most of it.

"You've turned into quite the little slut now haven't you?" Pete commented, as he watched Jessica's finger slide in and out of her ass.

"Are you going to talk or are you going to fuck me?"

Pete needed no further convincing as he started to push his cock into Jessica's wet little asshole.

"Owww. Fuck! Go slower!" Jessica groaned.

"You wanted to be a slut, so I'm going to fuck you like a slut!"

With that, Pete shoved his dick up to the hilt in her tight little butt hole, ignoring Jessica's yelps of pain. Her face was still hovering over Candy's unconscious body as Pete reached around to grab one of her breasts, squeezing it hard. Jessica moaned as her tight muscular ring fought against Pete's invading cock.

"Fuck, you have a tight ass babe!"

Jessica soon felt her head being pulled back, once again as Pete grabbed a fistful of her hair. He was pumping into her harder with each thrust, reaming her ass. She was relieved when he finally started to withdraw, relieving the pain he had been causing her.

"Get your face down here and suck my cock now, whore!"

As Jessica turned around, Pete pushed her body to the bed and rolled her over to her back. He then straddled her chest, putting his cock in front of her face. As she opened her mouth to take it in, Pete lightly slapped it on her lips.

"Beg for it." he said bluntly.

"Oh, please let me suck your cock! I want your cum in my mouth."

Pete then shoved his dick past her lips into her throat, almost choking her in the process. Jessica fought the gag reflex and relaxed her throat to accommodate his invading cock. He yanked at her hair as he fucked her face, drawing her head in to meet his dick. She was frantically sucking, slurping at the cock in her mouth as Pete slid it in and out. Suddenly, Jessica was taken by surprise as a shot of hot cum hit the back of her throat.

"Ahhhh, fuck," Pete moaned. "Swallow it all bitch!"

She gulped the bitter liquid down, as it spurted into her mouth. Pete pulled his cock from her lips and smacked her lightly across the lips with it.

"See, that wasn't so bad was it?"

Jessica wiped her face, and sat up. Pete was already putting his clothes back on. She remained silent as she straightened herself up. When she was done, she walked out of the room without a word.

As she stepped through the doorway, someone grabbed her by the arm. She turned to see Jay standing there, grinning.

"Are you having fun?" he asked.

Jessica nodded.

"Good. Come with me."

Jay led her back into the main room. She could feel everyone's eyes on her as she entered. She also noticed a video camera on a tripod standing there.

"Jay, I think this is getting out of hand."

"Nonsense."

Jessica felt someone grab her ass. She turned to see a man smiling at her. She managed to force out a smile as the stranger groped her. She then felt his hand drift to her pussy, slipping a finger inside her. Another man walked over and started to undo he top. Once her breasts were free, he leaned down and sucked on her nipple. Jessica closed her eyes and tried to ignore the fact that the room was filled with people, leering at her. She widened her stance to allow the man behind her better access to her pussy. As he fingered her, put his mouth at her ear.

"I bet you're a dirty little whore aren't you?" he whispered.

Jessica opened her eyes and saw the camera staring back at her.

"Yes," she replied.

"Then bend over and show me."

Jessica pulled herself away and got down on all fours. She looked back over her shoulder with a smile.

"What are you waiting for?"

The man promptly undressed and took position behind her. She closed her eyes again as his hard, thick cock slid into her little wet cunt. When she opened her eyes again, the man that had been sucking her tits had his dick out and was wagging it in front of her face. She opened her mouth and looked up at him. He grinned back at her as he grabbed her head, pushing his cock past her lips.

damonX
damonX
2,997 Followers
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