Holly’s Island: The Complete Collection

by G. C. Edwards

  “You need to get over here and fill my pussy with you hard cock.” Holly commanded him.

  As if on auto pilot Caleb walked to the bed, stripping off his clothes as he approached. His cock, now released from the confines of his shorts, stood at rock-hard attention as he climbed onto the small bed, right in between Holly's long smooth thin legs. Sara quickly slipped the dildo out of Holly's cunt as Caleb took its place, placing the tip of his cock at the entrance to Holly's beautiful pussy. Pushing forward he forced the head of his big cock into her fuck hole.

  “Fuck me with your cock, please!” Holly nearly screamed grabbing at his ass as she tried to thrust even more of his hard penis inside her tight pussy.

  Caleb pushed hard against her, steadily inching his huge dick deeper into her cunt. Holly was so tight that just getting half of his massive cock inside her had been a struggle, but she was so wet with lust, so obviously overcome with pleasure that Caleb didn't even worry that he might hurt her as he kept pushing hard, forcing his stiff member deeper and deeper into her hot little fuck box. Before he knew it he was buried to the hilt and she was calling out for more.

  “Now do me! Fuck me with your hard cock! Fuck my pussy with your big dick!”

  Caleb wasn't going to disappoint her and started to slowly fuck her cunt with long easy thrusts, Holly groaning with each plunge of his big prick into her teenage pussy.

  “Fuck me! Fuck me! Fuck me!” She kept repeating with every deep drive of his cock into her pussy. “Oh, god, I gonna cum!”

  Her back arched and her head snapped back against the pillow as her body shivered in orgasmic release. Her already tight pussy closed down like a vice against Caleb's cock, bring his thrusting to a halt with every rhythmic constriction of Holly's spasmodic orgasm. As her pleasure finally subsided Caleb grabbed her long thin legs and pushed them forward against her chest and began to fuck her harder. He wasn't pounding her like he did to Ashley, but he wasn't taking it slow anymore either. They were deep powerful strokes, yet gentle at the same time and angled slightly upward to perfectly hit her g-spot with every movement. It quickly blasted Holly's body into a blissful heaven of multiple orgasms and when she was nearly exhausted from pleasure he grabbed her hips and flipped her over keeping his hard cock deep inside her. He held her up as he went at her from behind, fucking her doggy-style until she was again lost in the throes of sexual bliss.

  “Oh god, please don't ever stop!” Holly tried to yell, but it came out as barely a whisper.

  She couldn't even hold her head up at this point as her body was fully drained, taken over by the periodic shiver of random orgasms. Caleb never wanted to stop fucking her, but the cum couldn't be held back much longer. He eased her down to the bed as he continued fucking her from behind, slapping against her tight little ass with each lunge forward. Finally when he just couldn't take it any longer he put his arms on either side of her body to brace himself and pounded her tight twat with quick short thrusts, popping his thick cock head in and out of her cunt until he finally sunk his dick deep inside her pussy and unleashed his hot sticky seed. Explosions of ecstasy plowed through his body as each squirt of baby juice fill up Holly's teenage cunt and was then forced out by his still hard thrusting cock, dribbling out of her snatch to form a pool of white goo on the bed beneath her.

  Eventually, even though he desperately wanted it to stay forever in Holly's pussy, his softening cock, now lacking the structural stiffness needed, was forced out and Caleb collapsed on to his back next to the sex overdosed Holly. Sara, who had been intently watching her friend get fucked, quickly snuggled up to Caleb and began mashing her sex against his hip. Holly, recovering quickly, took up residence on his other side as they both fondled his soft pussy-soaked cock as their hot wet cunts humped against his body.

  “Okay, girls, let's let Caleb recover,” Ashley said standing in the doorway as she removed her own wet hand from inside her cutoff shorts, “besides, dinners getting cold. We'll have plenty of time to play after we eat.”

  They were all having so much sex that they eventually had to work out a schedule. As much as they loved sex with Sara and Holly, Ashley and Caleb wanted at least one night a week to themselves. So on Monday Caleb and Holly spent the night over at Ashley and Sara's house. On Tuesday, Sara came over to Holly and Caleb's house while Ashley was working. Wednesday was Caleb and Ashley's night alone, while the girls spent the night by themselves. On Thursday and Friday afternoons Sara and Ashley had some 'alone time' before Ashley's night shift and then Sara would join Caleb and Holly for dinner and some after dinner fun. Saturday's were reserved for the girls to have their slumber parties and Sunday Caleb and Holly were back over at Ashley and Sara's house. It was a busy, sex-filled week, but they didn't want it any other way.

  At first the slumber parties were limited to Katie and or Sasha, but Ben soon became a regular too. Unfortunately, Jacob's job now had him working full time out on the fishing boat and he became less and less a fixture in Holly and Sara's group of friends. Sasha, who was closer to him than any of the others, found out that he was also spending most of his spare time on the other side of the island hanging out with William and his friends, which included several resort girls. After that they only saw him briefly in passing and he never again was a part of their group of friends.

  In the beginning, right after Caleb became a full participant in Holly and Sara's love life, it became clear that he was fully unaware of extent of Holly's sexual life. When he heard that Holly was not only sleeping with Sara, but also her friends Katie and Sasha it took some convincing that the behavior, while admittedly a bit unusual, was not harmful in anyway. However, when told that she was also sleeping with Ben it took much more time and energy to convince him that that relationship was okay. He realized in the end that his jealously was too blame and if he wanted to keep fucking Holly and Sara, he would have to put his ego aside and learn to share. Besides he had taken a real liking to Ben and couldn't bring himself to feel too upset over Holly's choice of lover.

  So, Caleb finally became okay with the fact that Holly was exploring her sexuality with her friends and even became happy in the knowledge that she was doing it in the safe and loving environment of his home. But he was unprepared for what would happen next.

  Even though the girls knew they shouldn't talk about their sexual relationship with Caleb and Ashley it eventually slipped out during one of the early slumber parties with Katie and Sasha. Of course, they immediately wanted in on the fun and Sara and Holly felt bad to deny them the pleasure. So instead of asking Caleb they decided to take action.

  On Saturday night the girls were naked and fooling around while they waited for Caleb to fall asleep and then all four of them slipped quietly in to his darkened room. Sara and Holly gently settled into their usual spots on either side of his naked sleeping body while Sasha and Katie went under the sheet at the foot of the bed and gently took turns sucking on his flaccid penis. Caleb's cock was rock hard before he woke up.

  “Oh, hey girls, you're friends already fell asleep huh?” Caleb said his head still groggy from waking up.

  “Thought you might want some company,” Holly purred pressing her already wet cunt hard against his hip.

  “Oh, that feels so good,” Caleb moaned and then a confused look spread across his face. “What's going on?”

  “Like Holy said we thought you could use some company.” Sara said pulling back the sheet to reveal Katie and Sasha working hard on his engorged dick.

  “Oh, god!” Caleb moaned. “You girls have gone … Uhhh, god, that feels amazing. You guys shouldn't … Oh! Jesus.”

  “Just go with it, Caleb. There's nothing wrong with it. Everyone just wants to have a little fun and feel good. You don't want to deny out friends the joy of your big cock, do you?” Holly whispered to him.

  “With you and Sara it's differ... oh fuck it … who wants to be first!”

  “Me!” Sasha yelled while Katie's mouth was full of cock.

  “Ahh man, no fa
ir my mouth was full!”

  “Don't worry Katie, everyone will get their chance and I'll probably last longer with you after I cum first with Sasha.” Caleb assured her as Sasha straddled him and began to grin her pussy against the underside of his rock hard cock. “In the meantime why don't you bring that cute pussy up here like Holly and Sara are doing and I'll give it some attention, okay?”

  Katie nodded with great enthusiasm and took her place on her hands and knees next to Sara, putting her ass within range of Caleb's masterful fingers. Caleb grinned at the sight of three tight butts staring him in the face, their legs spread revealing their cunts already dripping with anticipation. Holly put her head down, sticking her ass up in the air and showing off even more of her sex to Caleb. Sara followed suit and copying her, Katie did the same, her slit so wet that her juices were starting to run down her leg. He touched Katie's pussy and instantly his hand was covered with her wetness, she groaned and pressed her sex hard against his fingers as he stroked her mound. He didn't waste any time with Holly, he knew what she liked and he gave it to her, thrusting his thumb right up into her hot little box, finding her g-spot with the tip of his thumb while massaging her hard little clit with the side of his forefinger, she'd be cumming before Sasha could get his dick all the way into her pretty pussy, or so he thought.

  Sasha was a beautiful olive skinned young woman who could have been straight out of the pages of Playboy. Her tits were perfectly shaped looking like big hard coconuts with large hard nipples pointing slightly upwards. Her hips were narrow but her ass was round and firm.

  He was still enjoying the view laid out in front of him, so he was surprised when Sasha promptly grabbed his hard cock, positioned it at the entrance to her young pussy and quickly sat down, filling her toned sunbaked body with his cock in a flash. That wasn't the end to his surprise as she didn't slowly and easily fuck him with long drawn out strokes like he expected, but instead immediately began to fuck him hard and fast, bouncing up and down on his big dick with gusto, her wet pussy slapping against his pelvis at the base of his cock with an audible smack on each down stroke. Soon she took her hands off his chest and balancing herself with long strong legs, began to pinch and pull on her big nipples while she rode him like a galloping horse.

  It was all Caleb could do not to immediately blow his load deep into Sasha's pussy. Holly began to shake in her first orgasm of the night which helped take his mind off of Sasha as he tried to concentrate on the three twats that also yearned for his attention. Once Holly began to orgasm he went back to Katie and her wet shaved cunt that was practically crying out for penetration. He gently pushed the tip of his forefinger against her willing opening and when she felt that she rocked quickly back on her knees, forcing Caleb's entire finger deep up inside her fuck hole. They quickly got into a rhythm as she rocked back and forth as he finger-fucked her young pussy. Even at nineteen, half a year older than Holly, she was the smallest of the three girls, but she easily produced the most amount of lubrication making it easy for his finger to slide in and out of her small pussy.

  The excitement of sharing Caleb was a super turn on for Holly and she quickly came again, even though Caleb was only haphazardly working her cunt. Sara was patiently waiting her turn, biding her time by first making out with Katie and now helping Sasha fondle her tits. When Katie's tight fuck hole finally clamped down on Caleb's finger and began sucking it deeper and deeper into her teen pussy as she shook with orgasmic delight, Caleb knew that he needed to reward Sara for her good sportsmanship.

  Slipping his fingers out of both Holly and Katie's spent little fuck boxes he grab for Sara's ass and pussy with both hands. Placing one hand on her tight ass, the other against her pelvis, and positioning both thumbs at the entrance to her hot wet cunt he began to fuck Sara's sweet tight hole, alternating thumbs, faster and faster until Sara was screaming out for more.

  “Fuck me with both of them!” Sara yelled and Caleb obliged sinking both of his thumbs into her sweet tight fuck hole as Sara nearly collapsed, cumming hard against his hands, Caleb holding her up by her pelvis until he let his big fingers slip out sending her sinking onto the bed.

  Caleb then sat up and eased Sasha on to her back and showed her what fucking an experienced man was really like as he pounded her pussy with hard fast strokes until Sasha exploded in orgasm. Her pussy latched on to his thrusting cock as it practically sucked the orgasm from his body, drinking up his spewing cum as he erupted deep inside her pussy. He pulled out of her still quivering cunt and let the last few ropes of cum splash against her flat belly and large perfectly round tits.

  “Wow, I don't know if I can handle that!” Katie said with awe looking at Sasha's ravaged, cum splattered body.

  “Don't worry Katie, I only fucked her that hard because I knew she wanted it like that. We can go slow, at your pace or we don't have to have sex at all if you don't want to.” Caleb said calmly.

  “Yeah, Caleb is always slow and gentle with us.” Holly said. “It's like he knows exactly what each one of us wants.”

  “Okay I trust you. What do you want me to do?”

  “Well first I need some time to recover so why don't you girls work on your kissing skills.”

  “Okay!” Holly said excitedly as she laid a big sloppy kiss on Caleb's lips, opening her mouth like Sara had taught her and running her tongue across his lips until he returned the favor, their battling tongues instantly starting to revive his soft cock.

  “Well, thank you, Holly, but what I meant was you guys could practice on each other.” Caleb said with a laugh after Holly had finished her kiss.

  “Oh!” Holly said joining his laughter.

  The girls were all pretty familiar with each other’s mouths by this time, but as it was always a fun thing to do they dove in with gusto. Soon Holly and Sara were locking lips while they squeezed each other’s tiny pink nipples and Sasha and Katie were tongue fighting as they each finger-fucked their pussies, Katie having fun smearing the large amount of Caleb's cum all over Sasha's cunt. After a few minutes of watching the sensual scene Caleb was once again rock hard.

  “Okay Katie, I'm ready if you are.” Caleb said with a smile looking at her little naked body with great delight.

  “Okay!” Katie responded happily.

  “Girls why don't you test her to make sure she's ready?” Caleb asked with a grin.

  Holly smiled back and slipped her middle finger up inside Katie's tiny pussy, wiggled it around, pulled it out and then licked her finger clean.

  “Super wet and ready for cock,” She laughed.

  Katie crawled over to Caleb and after a quick pause to give his cock a couple of sucks she sat down on his waist, pinning his dick between her pussy lips and his stomach.

  “Oh, you are just too cute!” Caleb said grabbing her narrow hips and grinding her body against his hard on.

  “Mum, that feels so good!” Katie purred as her wet lips slid up and down the underside of his big hard penis.

  “You want to see how it feels inside your pussy, Katie?” Caleb asked lustfully and she nodded her head excitedly as she got to her knees. “Girls, help her out, okay?”

  Holly and Sara got in position on either side of her to help her keep her balance while Sasha took hold of Caleb's hard dick and placed the tip at the entrance to Katie's fuck hole. Caleb knew that Katie, due to her petite size, was going to be the tightest fit out of all the girls, but she also easily produced the most pussy juices which would help out tremendously. He felt the weight of her body press down on the top of his stiff cock causing half of its head to be forced up inside her. He gently flexed his butt muscles causing Katie to bob up and down on the tip of his cock, but the head still refused to pop inside her pussy. Caleb grabbed her small hips and ever so gently pushed her body against his raging cock finally managing to slip his thick head inside Katie's hot, wet, and very tight cunt.

  “Oh, god, I think I'm gonna cum!” Katie screamed as the bulbous head of Caleb's big cock suddenly filled her snug
pussy. Holly and Sara held her tight as she shook hard in the throes of a monster orgasm, her twat contracting so tightly around the tip of Caleb's cock that only Sara and Holly holding her down kept it from being spit out by the vice-like squeezing of Katie's cunt. Her pulsating pussy seem to continue on its orgasmic course for some time, until she finally braced herself against Caleb's chest with her arms and, still breathing heavy, looked up at Caleb and smiled.

  “Now I know why Sara and Holly love fucking you so much!” Katie sighed. “Now let's see how much of that cock I we can get inside my pussy.”

  With that Katie started slowly bouncing up and down atop Caleb's big hard dick slowly forcing it further and further inside her wet slit. With Caleb thrusting and Katie bouncing his big cock wiggled it's way deeper and deeper into Katie's tight pussy until she finally bottomed out, her cunt lips stretched wide around the girth of Caleb's penis, her copious juices getting squeezed out and running down his ball sack.