Fantasy Island

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Jessica pays a visit to the new Fantasy Island resort.
8.4k words
4.36
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Part 1 of the 2 part series

Updated 09/22/2022
Created 11/04/2012
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Erlikkhan
Erlikkhan
3,980 Followers

"Oh fuck... oh fuck... uuuunnnnggghhhh..."

Jessica felt her pussy clench around the vibrator up her cunt. A trickle of cream oozed from her slit and slid across her asshole. She sank back into the couch and tried to catch her breath. Her eyes were glued to the big screen TV. She was watching a woman getting fucked by a group of men. They weren't just fucking her. They were ravaging her.

The woman on TV was choking on a cock rammed down her throat as two huge battering rams pummeled her pussy and asshole. Several more were waiting their turn. Jessica touched the vibrator to her clit and felt her insides explode for a second time. She shoved the vibrator up her cunt. A third orgasm hit like a thunderbolt and left her drained.

Jessica turned off the video and put the vibrator away before she fucked her pussy into oblivion. Getting gang-fucked by a roomful of strangers had always been a fantasy. She wasn't sure it was one she really wanted to live out. She had been in threesomes a few times, and even a foursome, but a roomful of strangers would be a whole new level. Still, she loved watching videos of women getting gang-fucked.

Jessica walked into the bedroom and looked at the 27 year-old blonde with big blue eyes staring back at her from the mirror. She didn't look like a woman who fantasized about having non-stop sex with a group of strange men. She looked more like the girl next door or a soccer mom.

Jessica's eyes wandered down her naked body. She tweaked the nipples of her D-cup breasts that hung on her 5'6" frame like two huge melons. Her eyes glanced at her cleanly shaven mound. Beads of cunt juice clung to the folds that peeked out from the gash down the middle. She turned around and looked over her shoulder, admiring her perfectly rounded bubble butt.

Jessica decided to head to Fantasy Island, a new resort hotel in town, and hang at the pool. She had never been there. Theoretically, the pool was only for guests, but Jessica was quite sure no one was going to ask her to leave. They would be too busy enjoying the view of her 36D's practically falling out of her bikini top.

When she arrived, a man wearing a tuxedo intercepted her at the front door. He was tall and handsome. Jessica wondered if he knew she was not a guest. She hadn't done anything wrong, and the lobby was open to the public, so the worst he could do was warn her against using the facilities. She gave him a friendly smile.

"Welcome Jessica," he said in a deep voice with a heavy accent. "We've been expecting you."

He snapped his fingers and gestured across the room. A short man in a tuxedo came over carrying a tray with two glasses of champagne. The man that greeted her handed one to Jessica. She wondered how he knew her name. They must have mixed her up with another guest. She decided to remain quiet and took the glass. He toasted her.

"The pool is out back, Jessica," the mysterious man told her. "There is a dressing room on the right. Have a pleasant stay."

Jessica thanked him for the drink and headed to the dressing room. She stepped out of the cutoff jeans and t-shirt covering her bikini, and pulled on a short green wrap. Jessica stuffed her clothes in the oversized handbag and headed for the pool. It was crowded. She spied an empty lounge chair and grabbed it. She was about to remove her wrap when she heard a male voice behind her.

"Excuse me, Miss... um... but, um... uh, I was wondering if you wanted to join us -- you know, my friends over there. We have a private cabana. It has its own hot tub."

Jessica turned and saw a man in his early forties. There was a wedding ring on his finger. She looked over to where he was pointing and saw four other men all about the same age. They must be here for a conference without wives. It was a familiar scenario at many of the nearby resorts.

"Why me?" Jessica asked. "I'm not a hooker if that's what you were thinking."

"No, no... I know that, but, um... you're young and pretty and... oh, who am I kidding. I can't do this. You see, I lost a bet so I had to ask any girl they picked to join us. They picked you because you don't look at all like someone who would do that. They expect you to turn me down -- maybe even slap me. They'd get a big laugh out of it. Look, I'm sorry Miss. I won't bother you anymore."

Now Jessica was intrigued. Teasing a group of married men could be fun. They looked safe and harmless. She would love to push their buttons. If they were nice, she might even up the ante and give them something to tell their friends about when they returned home. Despite her earlier workout with a vibrator, she was still horny. She hadn't been fucked by a real cock.

"Don't worry about it," Jessica told him. "I'm kind of flattered actually. Why don't we go meet your friends? Let's have a little fun. That way the joke will be on them and not you."

The other four were at a nearby table watching. They all looked shocked when Bob returned with Jessica. She could see a wedding band on two of the men but guessed they were all married. She let her wrap slide off her shoulders. Their eyes grew big as they gazed at the huge pair of tits about to burst from the tiny white bikini top. The patch of cloth covering her pussy molded to the swell and the outline of her gash.

"Hi. I'm Jessica. It's so nice of you to invite me to join you," she said, using her sexiest voice. "I just love hot tubs."

Besides Bob, there was Randy, Mike, Bill, and Rusty. They rented a private cabana with a hot tub and moved inside. Jessica slid into the bubbly water directly across from Bob. She sank down and stretched out her legs. Her foot slid up Bob's calf and between his thighs. His eyes got big.

"Is your wife here?" Jessica asked, staring at him with a playful grin. "She's lucky to have such a sweet man for a husband."

Bob stuttered and shook his head no. Jessica's foot found his cock through his swim trunks. It quickly grew hard. He looked around to see if anyone else noticed. The bubbles in the water hid what she was doing. They kept asking her questions about where she was from and what she did. Jessica answered as she continued to tease Bob's throbbing cock with her foot.

Her toes found his knob and rubbed it. Apparently, that was too much for Bob. His face contorted with agony. He stifled a grunt and clenched his teeth. Jessica could feel cum oozing through his swim trunks. She rubbed her toes through his creamy ejaculate as it dispersed into the bubbly water.

"Are you okay, Bob?" Jessica asked, pulling her foot away. "You look a little flustered."

"Uh...um...yeah," he stuttered.

"That's good. Hey, does anyone else want to get naked? Hot tubs feel so much better without any clothes."

Jessica slid down in the water and pulled off her top. She threw it over the side. Next, she removed her bottoms.

"I just love how the bubbles feel against my naked skin," Jessica teased. "Especially my nipples. They get really excited."

"That's not the only thing getting excited," Mike said jokingly.

"Really?" Jessica replied with a mischievous grin. "Can I see?"

"Show us yours and we'll show you ours," Randy offered.

"Okay. You got a deal."

Jessica slid to the middle of the hot tub and stood. Her 36Ds hung from her chest like two grapefruits topped with swollen light brown caps and an erect tip poking out from the middle. She slowly turned in a circle letting them all have a good look. She squeezed them with her hands and rubbed a fingertip across her nipples.

"I showed you mine," she said. "Your turn."

The men looked at each other. Mike stood on the seat. His semi-hard cock was long and thin with a big purple knob. Randy joined him. His cock was thicker with a bullet shaped knob. Bill stood, revealing a banana shaped cock. Rusty was embarrassed by his smaller but fully erect cock with a huge knob at the tip. Bob stood last. His cock was the longest of all.

"Wow. They look delicious. Why don't you boys sit down on the edge of the hot tub so I can perform a closer inspection?"

They sat in a circle. Jessica picked Rusty as her first victim. She moved between his knees and slid each nipple across the swollen knob of his five inch cock. It pulsed with excitement. She spit on it until it was covered with saliva, then wrapped her hand around his shaft and pumped in a twisting motion.

"Very nice, Rusty," Jessica told him. "Do you mind if I put it in my mouth?"

He was too bewildered to reply. Jessica flicked her tongue across the sensitive underside of his knob, then slid her lips down the length of his shaft. Seconds later he swelled. Spurt after spurt of hot cum poured into her mouth until it was leaking out and running down her chin. It was like he hadn't drained his balls in a month. When he was finished, Jessica showed him what he did in her mouth and swallowed.

Jessica moved to Bill's banana shaped cock. She pumped it with her hand and spit all over it, then slid it between her 36D's and squeezed them tightly around his throbbing shaft. Looking into his eyes, Jessica jacked him off with her oversized melons. She tilted her head down and flicked her tongue across his knob each time it punched up from between her tits.

"Cum for me baby," Jessica begged. "Cum all over my tits."

Her warm breasts slid up and down his shaft faster and faster. Her tongue continued to torture his knob. Bill grunted. A spray of hot cum splashed off the bottom of her chin and dribbled down her creamy globes. She wrapped her hand around his spewing cock and aimed it at each nipple. When he was finished Jessica rubbed his cock through the creamy mess and licked it clean, then squatted in the water to wash it off.

Randy was her next victim. Jessica wrapped her hand around his thick bullet-shaped cock. Her fingers twisted and turned around the throbbing flesh as she pumped up and down with her hand. A look of agony showed on his face. Jessica leaned forward and sucked him deep into her mouth. She felt him swell and pulled him from her lips, pumping him with her hand.

"Cum on my face," Jessica begged in a voice full of desperation.

A loud roar escaped from his lips. A steady spray of hot cum bounced off her cheek and shot across her nose. More splashed between her eyes and landed in her hair. Like the first two, his reservoir of cum seemed endless. Spurt after spurt spewed from his cock until her face was completely doused. A huge strand dripped from her chin.

Jessica used her fingers to scoop up the creamy mess running down her face and licked them clean. She dipped her face in the hot tub to wash away the rest. Mike became her next customer. He had a seven inch cock with a large purple knob. Jessica wrapped a hand around his throbbing flesh and gazed up at him with lust filled eyes.

"Have you ever fucked a girl in the throat, Mike?"

Jessica spit all over his cock and slammed her mouth down his length. She took him into her throat until her lips were pressed against his pubes. Her tongue snaked from around his cock and licked his balls. Jessica moved back up his length, then slammed down, taking him deep into her throat. She did this again and again, fucking him with her mouth.

"Oh fuck," Mike groaned.

Jessica slid a finger across his scrotum and rubbed it over his sphincter. Moving her lips to his knob, fluttering her tongue across it. When she could sense he was about to explode, she slammed her mouth down his length and into her throat. At the same time, she shoved a finger up his ass.

"AAAAARRRRRGGGGHHHHH..."

Mike's primeval roar was loud and desperate. His cock exploded into Jessica's throat with such force that she choked. Some came oozing out of her nose. She moved back up his shaft, her lips clamped tightly around him. Spurt after spurt continued filling her mouth until it was leaking from her lips and dripping down her chin.

Jessica's finger, which was still buried deep in his asshole, found a spot near his scrotum and pressed. It was like pushing the ON button. His cock got renewed life and pumped several more spurts into her mouth. She finally pulled away and stretched her lips open to show him the huge load. Jessica closed her mouth and swallowed it all.

Bob was her last victim. She was saving something special for him, something she was sure he had never experienced. She wrapped her hand around his cock and slowly stroked while looking into his eyes.

"Have you ever fucked a girl in the ass, Bob?" Jessica asked "No? Then this is your lucky day."

Jessica stood on the hot tub seat and turned around. She lowered her ass to his hard cock. Reaching between her legs, she guided his swollen knob to her sphincter and pushed down against it. Her tight knot stretched open until he punched inside. There was enough lubrication left from her earlier masturbation session that his cock slid in without resistance and disappeared up her asshole.

Jessica placed his hands over her large tits. He squeezed the soft flesh and pinched her nipples. Bob thrust his cock up her asshole each time she came crashing down on him. The intense pressure from his big cock was driving her crazy. Jessica moved a finger to her clit and rubbed. Moments later the orgasm hit.

Bob continued to pound his cock into her. Another orgasm ripped through her pussy. Her asshole clenched his cock in a series of spasms. Bob felt his ball tighten and his cock swell. He grunted and thrust deep, spraying spurt after spurt of hot cum into her bowels.

With his cock still deep in her ass and cum oozing out around his shaft, Jessica plunged two fingers into her cunt and fucked herself senseless. A loud scream accompanied her next orgasm. She finally pulled away from his spent cock and stood. Cum streamed down her thighs. Jessica fell into the hot tub and let the bubbles massage her excited body. She found her bikini and pulled it back into place.

"See you later boys," Jessica said as she walked away, putting a little extra sway in her ass.

The five men all watched her leave. Bob stared at the ass he just fucked. The other four had their jaws agape remembering the most incredible blowjob they ever received. Mike finally shook his head and spoke.

"Jesus. I think we just hit the fucking jackpot."

"Definitely," replied Randy. "She's got to be a porn star. No normal woman could make five guys cum in less than twenty minutes."

"I don't know," Bob argued. "No porn star would just give it away like that. She's the girl next door that we all dream about - just out for a good time."

"I agree with Bob," said Bill. "She's not a porn star. She wasn't acting. She loved it. You could tell."

****************

Jessica was proud of herself. She had given five men the memory of a lifetime and satisfied her own sexual cravings at the same time. A tall muscular black man intercepted her as she headed back to the pool. He was wearing a t-shirt that indicated he was hotel security.

"Gate crashers aren't allowed in here," he said with a scowl. "Only registered guests can use the pool. You need to come with me to my office."

"What? No, the man at reception invited me to use the pool. You can ask him."

The security guard didn't reply. He just stared at her with cold eyes. Jessica decided to use charm on him. It had always worked in other hotels. She puffed out her tits until they were practically falling out of her top.

"Really, he did invite me to use the pool," Jessica pleaded in her sexiest voice. "Besides, my being here isn't hurting anyone. Isn't there something I could do to convince you to let me stay."

Jessica put her hand on his muscular arm and stepped closer. Her left tit brushed against him. The security guard moved his face close to hers. His voice had a threatening edge.

"Are you trying to proposition me? That's called prostitution. I should call the police."

"No, please," Jessica begged. "I'm not a prostitute. Don't call the police. I'll do anything...anything at all."

The security guard stared at her coldly until Jessica was shivering with fear. She didn't want to go to jail. Her boss would find out. Her friends would know. It might even get back to her mom and dad. Just then the security guard's cell phone rang. He answered it, nodded his head a few times, and hung up. He looked down at Jessica, his eyes still cold.

"I have to run an errand for the boss. Give me your driver's license and meet me back here in ten minutes. I'll give you one chance to convince me why I shouldn't call the police. You had better show or you'll be spending the night in jail. I know where you live."

Jessica went into the ladies room. Her heart was beating fast. Every nerve ending in her body was tingling with a mixture of fear and excitement. She entered a stall and closed the door. After peeing, she went to the sink and splashed water on her face. She gazed into the mirror at the innocent looking blonde staring back at her and asked, "What have you gotten yourself into, baby?"

The woman in the mirror shrugged her shoulders. "It's your fault. You told him you would do anything. How bad could it be?"

Jessica sighed. "I wish I knew. I'm a little scared."

The girl in the mirror smiled back at her. "Go for it sweetie. Once you get his cock in your mouth he'll melt like butter. They all do."

"I hope so," Jessica replied.

Jessica walked out of the ladies room. The security guard was waiting. She smiled. He grabbed her arm and guided her to a door away from the crowds. He took out a key, unlocked it, and dragged her inside. The room was dark except for the ray of sunlight coming through a small window. They were in a maintenance room with buckets and pool equipment scattered about.

He hovered over her, his cold eyes lecherously scanning her body. Fear bubbled up inside her. Jessica was not sure what he wanted. She waited for him to speak but he didn't. She finally broke the silence.

"Um... do you want to see my tits? I don't mind showing them to you."

He fixed her with his cold stare. Jessica could feel her heart pounding in her chest. She reached behind her back and unsnapped her top letting it fall to the floor. Her hard nipples poked out from two creamy white globes that hung like large melons on her chest.

"Do you like them?" Jessica asked, squeezing her tits with her fingers. "Do you want to play with them?"

He didn't budge. Jessica rubbed a fingertip across her nipple and looked at him with wanton eyes. She couldn't seem to break the ice. She did the only thing she could think of that was certain to evoke a reaction. She squatted in front of him and rubbed her hand over the huge bulge in his shorts.

"Would you like a blowjob?" Jessica asked nervously. "I can suck cock better than almost anyone."

He still didn't say anything. She hooked her fingers in the waistband of his shorts and yanked them down his thighs. Jessica gasped when she saw the size of the coal black snake that unfurled between his legs. She wrapped her fingers around the monster in front of her and looked up to see his reaction. He had the same angry expression, but he hadn't done anything to stop her.

Jessica swirled her tongue across the bulbous knob. He grew bigger in her hand. She sucked the swollen tip into her mouth and continued to tease it with her tongue. Her hand stroked the expanding shaft. She could feel it pulsing against her fingers as it continued to grow.

Jessica stared at the monster she had built. She had been with a lot of men, but no one with a cock as big as the one in front of her face. It wasn't just the length. He was as thick as her wrist with veins bulging from the coal black shaft. She stretched her lips around him and moved down the shaft as far as it would go before pressing against her throat, but she could barely fit half of it in her mouth.

Jessica did her best to service the battering ram she was sucking. Her lips slid up and down his shaft. Her tongue swirled across the vein streaked flesh. She both hands wrapped tightly around his monster, pumping up and down as her mouth moved faster and faster. She felt the swollen tip slam against her throat again and again.

Erlikkhan
Erlikkhan
3,980 Followers