Holly’s Island: The Complete Collection (11 page)

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 fair 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.