Island Vacation (AllThingsCuddly and Machiavelli)

It was Friday night, spring break had just begun. Annalise already had plans for the week, she just needed the perfect man to take with her. Her tastes varied and this wasn’t the first time she had done this. Today her and the twins were on the prowl at a local bar. It was a local hang out for college students and seeing as it was officially the beginning of spring break, it was packed.

Some of the people here were clearly already drunk, others had only just arrived. Like her and the twins. When the three of them entered wearing their matching sorority shirts a cheer went up through the crowd. Around campus it was known that Annalise, although she was only a freshman, was the new leader of the Phi Theta Gamma sorority. Cindy and Sandy, more commonly just called ‘the twins’ were the newest initiates.

All three were known for their flirty attitudes. “Alright, girls. I know this is your first time picking, but what we’re looking for is fun. I think I’m in the mood for something… Tall dark and handsome. Keep an eye out and if anyone finds a good candidate, give a signal. It could take all three of us to lure him in.” Annalise told the others as she lead the way into the bar.

Eric was a college freshman, despite his looks which typically made people think he was older than that. It became insanely easy to get into places with a fake ID for him, and so he quickly became one of the more popular guys on campus, since he could get anyone alcohol for the right price. But on this night, the eve of spring break, he lounging in a booth by the bar, surveying the place for a hot babe that might be interested in a week of hot, meaningless fun. Not always a like prospect, but if he failed tonight he knew of many many parties full of many many drunken hotties that might fall under his spell.

A roar of approval went through the bar as some of the more well-known girls entered the place - a sorority leader and her newest comrades. Eric gave them a once-over, his lips turned up slightly. Twins... He and any guy would love to have both of them together. And the ringleader, Annalise, was well known for her body and her devious mind, though no guy had ever complained. They were certainly worthy of his notice.

But he was patient... And so he waited, wondering who else might catch his attention, unaware that he, the hunter, was likely being hunted too...

All three girls began to make a circuit of the place. Being hot sorority girls they hardly ever had to pay for drinks. By the time they reached the other side of the bar they had each had a few shots and held mixed drinks in their hands. Annalise particularly enjoyed receiving free drinks. She was a bit of a lush and though she preferred wine, anything with alcohol in it made her happy.

Her eyes landed on Eric and she smiled. Meeting Cindy's eyes from across the bar, she subtly nodded her head towards the booth. Cindy quickly got her sister's attention and soon all three met up at the booth. It was a semi-circle and so the twins each slipped in on opposite sides and were soon sitting on either side of Eric. Annalise on the other hand pulled up a chair and sat immediately across from him. As she sat she let out a small sigh. "I know the night is early, but I should have worn different shoes, my feet are killing me." She protested and slid her feet up into Eric's lap. "You don't mind, do you?" She was careful not to stab him with the stiletto heels.

Sandy and Cindy each set a hand on one of his knees and Annalise met his gaze from across the table. "You're not here looking for fun, are you?"

Eric was still musing over the crowd in the bar when he caught sight of the three women heading toward him, an oddly organized assault on his booth. Suddenly he was flanked by sexy redheaded twins, and Annalise was across the table from him, he feet propped up in his lap, the heels dangerously close to his equipment through the black fabric of his pants. In fact, she could probably feel her feet resting on the sizable package there. Attempting to remain composed as the attractive women caressed his knees, he merely raised an eyebrow, taking a slow sip of gin from a glass. "How could I complain?" he chuckled. "I suppose that depends on how you mean. I'm always looking for fun. But if you're asking if I'm here to get absolutely plastered and drunk... No, no I am not." He said, a small smirk on his face, knocking back the rest of his drink, sliding the glass to the edge of the table with expert skill. A waiter snagged it as he passed.

"But, no matter what I'm looking for, you three clearly are. I know the look of people who want to get something, and I'd love to sell it to you." He smirked slightly once more, almost a signature look, the look of someone who was used to knowing people and reading them, playing to what they needed and getting them to pay him for it. He was confident and sure of his ability in life, confidence that may or may not be well-earned.

The waiter returned, placing another glass on the edge of the table, closer to the girls than to Eric. "Would you please?" He said, gesturing slightly to the crystalline container.

Her nylon-covered feet certainly noticed the bulge they were resting on. As he explained he wasn't here to get shit-face, Annalise used one foot to expertly slip the shoe off the other foot, letting it fall to the floor under the table. The bare foot moved to start rubbing at the mound she found, keeping her gaze on Eric's face. As the new drink was set down, Annalise picked it up and brought the glass up. She ran her tongue along the lip of the glass then slowly slid it across the table, leaning forward to give him a great view down her shirt.

"We're in the market for a boytoy for the week. We're heading to the Bahamas all week and want someone to come with us. We already booked a nice little cabin on the beach and have an extra ticket. What do you say? A free island adventure with three sexy women?"

"Before you answer." Cindy said and she leaned close to whisper into his ear. "Have you ever seen..." She trailed off, her tongue playing along his ear.

"Twin redheads making out?" Her twin finished for her, whispering into his other ear.

Eric managed to barely keep his expression from changing as her foot slipped out of her shoe and began rubbing slightly against his dick through the thin fabric of his pants. He couldn't however, keep it from hardening against the stimulation, growing and throbbing hotly. Despite the onslaught of seduction, and the heat and sexiness of the whispers, the slow, teasing lick along his glass hinting at what those lips could do... He managed to respond. "Ah, but what's the catch?" he said, receiving the glass from Annalise and enjoying the glance down her shirt. "I think you know that any male in this bar would say yes to you in a heartbeat. So I'm surprised you haven't already nabbed somone... meaning there has to be a catch." He took a long sip from his drink as the twins whispered in his ears, tongues teasing, lips breathing hot, tantalizing air against his skin.

"I..." He faltered over his words for a moment. "Can't say that I have." He cleared his throat, and his cock throbbed in his pants, a clear sign that he was more than interested in imagining such a scene with these two hot college twins. "So. What would be involved in my employment as your 'boytoy', hm?"

She could feel the way his cock was quickly hardening. It throbbed when the twins leaned closer. She could only imagine what the girls said. As part of their initiation they had been tested in a variety of ways and Annalise had been impressed by them and decided to being them along for this week of fun.

"What's in it for us, you ask?" Annalise asked and her foot ran along the length of his hardening member, trying to gauge how big it was. "Well, we get to use you to fulfill our sexual needs. We'll feed you food and you'll feed us cum." She said, leaning forward and pursing her lips as she said the word 'cum'.

"Do you want to watch as Cindy and I..." Sandy whispered, allowing her sister to finish for her this time.

"Make out in front of you while Annalise sucks your cock..."

"The catch is," Annalise said, unaware what the twins were saying. "With there being three of us to please, it's unlikely you'll get any sleep the next week. By the time we're done with you, you'll be so sexually exhausted that you'll need a vacation from your vacation?"

Eric shifted slightly in his seat as her foot slowly stroked his covered cock. After letting out a small gasp, he leaned forward slightly. "That hardly sounds like a catch." He replied in a tone that wavered slightly with arousal. The twins continued whispering in his ear, hot, delicious things that made his cock throb even more. He cleared his throat slightly, then shifted again. "Well... I certainly haven't heard anything that would make me want to turn down this offer." He said, a hiss of hot breath escaping his lips as he finished the sentence. "But you haven't quite told me what all I'll be doing as your boytoy." He managed, a small smile on his lips. Then he groaned softly as her foot teased him even further.

His hand gripped his glass. "But if your job description is as lovely as..." he groaned again. "What the twins are suggesting.... Then I'm very likely to be... interested." He took a slow drink from his glass. "Unless, of course... there are more catches."

"The job description. Right. Ladies." Annalise motioned to the twins as she took a drink of her own mixed drink. A waiter passed by and she caught him by the arm, asking him for something quietly. The man looked slightly confused but nodded and went off.

When he returned he handed her a banana. Slowly she peeled it, looking eyes with Eric.

"Your job will be to clean out each of us." Cindy said in one ear.

"And fuck us til we cum..."

As the girls were whispering to him, Annalise slid the entire length of the banana down her throat then pulled it back out in one piece.

Eric cleared his throat slightly as the three girls so simply described what they wanted him to do for them over this next week. He had to admit, their "proposal" was better than what he had planned, and also more reliable. If he turned them down and couldn't find a hot girl to play with for the next week, he'd end up regretting it. And also having three girls that wanted to toy with him and have him fuck them to orgasm after orgasm....

There were few things better.

Taking a deep breath, he nodded. "All right, I fail to see why I should refuse. I'm in." He said with a slight smile, finishing off his drink.

"Our flight sets out tomorrow, but if you'd like, you can come back to our place tonight to get a... preview of the rest of the week." Annalise said, her foot still running up and down his erection.

The twins moved their hands up his lap and rubbed at his chest instead. "Of course, if you need to go home to pack first, that would be completely understandable." Annalise continued. "Though I have a feeling you won't need much in the way of clothing."

Her foot slid back and pressed instead between his legs to ever so gently caress his balls instead. "Oh, how silly of me. We never even introduced ourselves. I'm Annalise, and the twins are Cindy and Sandy. Ad you are...?"

He chuckled softly as she told him that he wouldn't need much in the way of clothes. "I can't imagine I will, if it's as you describe it. What all does this mysterious beach cabin contain, I wonder?" He mused teasingly, trying to get back at them for their seduction, to play a little back. "My name is Eric. I knew you, Annalise, as most around here do... But I was not familiar with the lovely twins who seem so... friendly." He said with a small smirk, wrapping an arm around the waists of the two girls as they leaned against him. "I have no problem with kicking off our spring break fun as soon as possible, Annalise. Lead on." He said, placing his glass back on the table and tossing down the cash to pay for his drinks. Her foot had been driving him mad, caressing and teasing his cock through his pants, and now... now he just wanted to get it free and play with these three lovely women who were so eager to play with his body and his cock.

It was the dream of any guy to have three girls hanging off him and playing with him, and he would be more than happy to oblige them in their desire for his body.

Annalise pulled her foot back and slipped it back into her shoe. Then Sandy slipped out to allow Eric out. The three girls lead him towards the exit and there were some disappointed boos as a few of the men protested the sudden departure of the sorority girls. They pretended not to notice and instead each of the twins wrapped an arm through the man's arms and led him back to their house.

When they arrived, a few of the other sorority girls were lounging about the main room. Upon seeing the three return with a man they looked interested. "Oh, only one, Annalise? That's not much to share." One of the girls said.

"Oh, don'y worry, we can tie him up and all play with him. He won't mind, will you, Eric?" She asked and snaked a hand behind him to squeeze his behind.

Eric had to admit that there was a certain amount of appeal in leaving the bar with three women. It was abundantly clear to everyone there what was happening, and he would no doubt be the source of much envy amongst the other males in the bar, and perhaps even a few of the ladies. The sexy sorority sisters escorted him to the sorority house, which he had expected to be mostly empty with all the girls off at parties. Yet there were a few still in the common area of the large house, and, to his surprise, he wasn't led upstairs to a room. Instead a conversation was exchanged it seemed that tonight he was not just going to be shared by the three sorority girls who had nabbed him, but also this group of their sisters. How lucky could a guy be?

They mentioned tying him up so they could all play with him and his cock twitched slightly in his pants. "Mmm, kinky." He taunted slightly. "How could I say no to such an interesting offer?" He replied, the small smirking smile on his lips. That smile briefly turned into a look of surprise as she grabbed his ass, to which he responded with only a small chuckle. He wasn't used to playing the submissive in sex, so this would be interesting.

But he, like any man, would do anything to have countless girls play with his body, and, most importantly, his cock.

The girls dragged him into one of the bedrooms then there were hands all over him stripping his clothes off him. When he was naked he was guided onto the bed and tied down spread eagle. The girls all crowded onto the bed around the prone man. There were a total of six now. Luckily the bed was huge so they all fit on the bed around him.

Annalise was perched between his legs so she began to rub at his cock. This was all part of the plan. Give him a night of crazy sex then it would be easy to convince him onto the plane with them. Once on the island he'd be their unwitting victim.

"Eric, these are Tasha, Rene and Tiffany. Girls, this is Eric." She explained and leaned down to start sucking his cock. Sandy and Cindy leaned over the man to start making out over him.

Eric was surprised by the quick movement of the girls, and he was quickly pulled to a bedroom with a massive bed. The six girls had hands all over his body, and they quickly removed his clothing, tossing it to the side of the bedroom, forgotten. His long, thick cock reacted instantly, hardening and growing as he was revealed. He only caught brief glimpses of the girls' glances at his dick, but the looks he did see were either impressed or full of desire. He was quickly pulled down to the bed where his arms and legs were restrained, causing a slight chill of arousal and anticipation to run down his spine. He only barely registered the names of all the new girls, what with Annalise slowly stroking his throbbing cock, causing him to groan ever so quietly.

The hot redheaded twins began to make out passionately over his body, and he had the perfect view of the scene, He felt hot, wet, delicious sensations wrap around the shaft of his manhood and knew that Annalise had taken him into her mouth. Her lips and tongue were heavenly, causing him to shift slightly and groan slowly. Six clothed girls playing with his naked body was so fucking hot. The fact that he was the only one naked made the situation a little more hot and kinky as they did what they wanted with his helpless body. He wasn't willing to accept that he liked being a toy to their hands and mouths (and hopefully later a different hole...), but he also couldn't deny that he was throbbing in the blonde's mouth.

The night was a blur of sexy fun. Annalise sucked on Eric's cock for a few minutes but then she stopped, leaving his hard cock throbbing. For a few minutes he was left hard and horny but it was well worth it when Annalise slipped a condom onto the hard cock and then stripped off her bottoms and mounted him. She rode him hard until they both climaxed.

While she was riding him, the twins were stripping each other and soon they were fondling each others breasts. The other three were all hands on Eric. Massaging his balls, playing with his nipples, licking his body. Rene stripped off her bottoms and rode Eric's face, making him eat her out while two hands (belonging to one of the other girls but they were such a mess of limbs it was hard to tell which) were playing with her breasts.

After Annalise rode Eric, the condom was pulled off and thrown away. At that point he was untied, giving him a chance to feel up all the girls around him. Once he was warmed up again, he was given another condom and this time he had his choice of girls. At some point the girls pulled out some toys and were using them on each other. Each girl had at least one climax throughout the night and Eric had multiple.

Come morning they were all passed out, naked and covered in the smell of sex. A pile of limbs and bodies.

Eric had never enjoyed himself quite as much as he enjoyed that night with six girls all to himself. A girl grinding her wet pussy against his mouth as he drank in her delicious juices, twins making out over his toned, masculine body, playing with their lovely pale tits. Hands playing with his balls, teasing his nipples, tongues licking and biting and sucking. Annalise rode him until they both came loudly, the condom discarded as she dismounted him. He was untied and his hands played with so many tits, fingers fucking slick, dripping pussies, and his lips tasting each of them at least once. Hands continued to tease and play with him until he was raring to go again, and so the night went on...

He slowly stirred away the next morning, underneath a pile of sexy girls all clinging to him, breasts pressed to his skin, which did not help his morning wood. He didn't move much, trying to slowly awaken and not disturb the girls as he awoke. It was amazing to him that it hadn't all been a dream, and they had more than convinced him to go with them on their vacation on this island. He wasn't sure how many of them and which ones were going, but they were all smoking hot and absolutely sexy as hell. If they all went, he'd have a chance to fuck each and every one... Even if they didn't, he'd have a small group of girls to play with all day and all night....

There was no way he was turning that down.

As Eric started to shift, Annalise also stirred. She slowly sat up and looked down at Eric. When she spotted hid morning wood she smiled and placed a finger to her lips then lowered her head down and started to suck on his cock. Her head bobbed. Slowly at first but then more quickly. She took a deep breath and slid his entire length into her mouth. Holding it there it was a few second before she pulled back and returned to bobbing. As he shot his hot load she swallowed most of it then left some in her mouth as she climbed up him. At first it seemed like she was just coming in for an innocent kiss but once their mouths were locked together she pushed the cum into his. She kept a firm hold on the kiss though, not letting up until he swallowed.

He could get used to this - a girl satisfying his cock every time he got hard. She gestured sexily for him to be quiet and he nodded as she slowly engulfed his cock in her mouth. She took him deep for a long moment, holding his full, impressive length in her mouth and throat before returning to the energetic motions of her head. He tried to remain quiet as best he could, but couldn't keep from letting out small sighs of pleasure. He reached orgasm fairly quickly, despite the previous evening's activities, and his hot, thick cum surged into her mouth. He bit his lip to keep quiet and as he glanced down he saw her swallow his load. God, it was hot when a girl swallowed.

She slowly slid up his body, pressing her lips to his. Her tongue forced open his lips and spread the little bit of his cum that was still in her mouth into his, and she held the kiss until he was forced to swallow the salty semen. He made a face of slight revulsion, but mostly chalked it up to her finding cum-stained kisses a turn on or just an absentminded action. While he didn't like the taste or the idea of what just happened, it was a small price to pay for six hot naked girls in the morning, one of which sucked him off the first chance he got. He would get over it.

It wouldn't be long before the others would stir no doubt, because of their movements in the bed. After all, they were all tangled up.

She saw the look on his face and she smiled. When she pulled back she carefully climbed off the bed, seeming very adept at climbing passed the other sleeping girls. She made her way to the bathroom and showered. Once she was satisfied with how clean she was, she came back out into the bedroom wearing a towel. Walking over she noticed that the other girls were slightly starting to stir. Reaching across she nudged the twins. "Hey you two. You need to get showered. We need to be leaving soon."

Cindy yawned and stretched, her hand ran over Eric's chest and she looked up at him, smiling. "Want to join us in the shower?" She asked and Sandy sat up and glanced over at her sister.

"Yeah, morning orgy." Sandy said with a giggle.

Eric watched Annalise leave the room - a lovely sight indeed - and then lay his head back down slightly, trying to ignore the lingering taste of his own cum. It was disgusting, and he hoped that never happened again. He honestly could say that he hated it, even if it was worth it in the long run. She returned after a bit wearing only a towel and began to rouse the other girls. Cindy almost instantly offered to let him join the two twins in the shower, and there was no hesitation. "How could I say no?" He said with a smirk, gesturing for them to lead the way as he swung his body out of the bed, trying to avoid the other nude girls still mostly sleeping.

Both of the twins seemed all too happy to have him join them, and he wondered how early their relationship with each other had gotten intimate. They were really good at playing with each other and making out, which indicated a good deal of practice... Did they always share their guys? Now he was just curious, but mostly for imagining them in various scenes. Fortunately, no doubt, he would make memories to replace those imaginings.

When the twins got Eric in the shower they got the water nice and hot. It was a large shower with jets in multiple locations about the tiled room. There were also handle bars with non-slip grips attached to the walls at various heights. Cindy pinned Eric to the wall and pressed her naked body against his, pressing her lips against his. Sandy knelt down and one hand went to playing with Cindy's mound while the other went to Eric's balls and she took his cock into her mouth. Though once he was hard and ready to shoot again, she pulled back. That's when Cindy used the grips on the wall to hoist herself up and ride Eric, still pinning him to the wall. When she was done, Sandy took her place.

Satisfied, they began soaping each other and Eric up. Eventually Annalise came knocking on the door, telling them to hurry up.

Eric was more than compliant to the twins, and entered the shower without hesitation. He suddenly found himself pinned to the wall, a small thrill of excitement rushing through him, stirring his cock despite it's recent activity. Cindy pressed her lovely, curvy body against him and kissed him hotly, her tongue dancing with his. He felt the girl shudder slightly and then felt a hand on his balls, lightly playing with them as a warm, wet tongue lapped his cock into an inviting mouth, causing him to slowly harden. He could only suspect that the hot redhead was also playing with her twin's pussy as she sucked him. He slowly mounted the hill toward orgasm again, and Cindy moved away slightly, displaying pressing strength as she lifted herself using the handles and pinned him to the wall again, this time using her hot cunt wrapped around his cock. He groaned as she began to ride him against the wall, his pleasure mounting quickly. Cindy came quickly, her pussy squeezing and tightening around him, and Sandy took her place on his dick.

After groaning and moaning in pleasure, she took came on his rod, squirming and clenching and he barely held out as she finished riding him. As she pulled him out of her his orgasm came crashing down, splattering her stomach and sex with hot cum that was quickly washed away by the water. Their fun complete, the girls began to wash each other and him until an urgent call for them to hurry came to the door. Eric slipped out of the shower and grabbed the towels, drying himself off first and then helping the girls out.

When the three got out of the shower, Annalise was already dressed and had her bags packed. The twins were already packed but they did need to get dressed. It didn't take long though. Once they were all ready they got their bags and carried them outside. A taxi had been called for them and the driver loaded their bags into the trunk. As Eric came out, Annalise grinned. "There are three seats and four of us. Looks like I'm riding in your lap." She said with a smile.

Sandy climbed in first then they let Eric in, Annalise climbed onto his lap and Cendy climbed in last. This left Eric sandwiched between the red head twins with the blond Annalise on his lap. The driver didn't seem pleased but when Annalise tipped him a twenty he shrugged and started driving. When they got to the airport they easily cleared security and were soon on the plane. There were rows of four on either side of the aisle so they all got to sit together. The entire flight the girls teased him anyway they could. The 'casual' touching and stroking of his leg; 'accidentally' brushing his crotch. Two hours of them keeping him aroused.