Holly’s Island: The Complete Collection (10 page)

Caleb sank back to his knees in disgrace and Sara rolled off
Ashley's naked body and sat cross-legged at the head of the bed hanging her
head in shame. Ashley sat up and looked at both of them as sternly as she could
muster, until she finally burst out laughing.

“Sorry, sorry …” She said in between laughs, “but you pull a
fast one on me and I think it's in my rights to make you both suffer a little.
No one needs to be sorry, in fact, I'm thrilled to death. I mean as long as you
are okay with this Caleb.”

“What? … I mean yeah, I guess so, I mean … What do you mean?”

“I just don't want you to think badly of me or Sara for what
we do in the privacy of our own house. Sara had her Blooming Day a few months
back and well one thing sort of led to another.”

“No, no, I mean I was a little shocked at first, but as long
as it's mutual and no one gets hurt I have no problem with what you two do.
Hell, you guys are closer to best friends anyway. She's an adult now, she can
make her own decisions and if Sara wants to know more about her body and the
joys of sex I have no problem with you showing her. ”

“What about you?” Sara asked hopefully.

Caleb looked over at her and then over to Ashley who smiled
and nodded her head.

“I would love to help out if that is okay with Ashley.”

Sara looked over at Ashley who again nodded her approval.

“Sara has wanted to join us for quite some time now and while
I didn't have a problem with it, I wasn't sure how you would react to such a
request. But if you don't mind sharing our bed with Sara I certainly don't mind
either!”

“Yea,” Sara exclaimed clapping her hands. “So can we start
now?”

“Sure, what do you want to do first?” Caleb asked, his cock
already back at attention.

“I want you to fuck me.” Sara said lustfully.

“Well, wow, okay … um, we can do that but maybe we can start
a little slower.” Caleb said with a smile as he climbed up on the bed to join
Ashley and Sara. “How about you just study it up close first, so you can get a
good idea of what it looks like and feels like and how it works?”

“Okay!” Sara said.

Caleb stretched out on his back between the two of them, his
hard cock standing at attention, while Ashley begin instructing Sara about the
mysterious ways of the penis.

“Wow, it's so stiff, but sort of soft at the same time!” Sara
said as she slowly played with her first real life penis.

Sara and Ashley were both on their knees next to Caleb, their
beautiful asses staring him in the face as they played with and talked about
his very happy cock. He couldn't resist reaching out touching their soft warm
bodies and as his fingers began to stroke their tight firm butts they both
stopped what they were doing and looked back at him with big smiles. Ashley had
one of the best asses he had ever seen, small, tight, and almost perfectly
round and Sara's was almost the exact replica only slightly smaller. In fact,
even though they weren't blood related, Sara seemed like a mirror image of
Ashley, same blue eyes and dark brown hair and same body type, average height,
small waist and skinny legs. Ashley's large round breasts were the only thing
really different as Sara's petite tits were smaller and more cone-shaped. Also,
Ashley waxed her pubic hair while, at the time, Sara had yet to try that
painful procedure, having to wax her legs was bad enough and she hadn't worked
up the courage to do that to her pussy. 

But the asses that presented themselves to him that night
were amazingly similar and as Ashley was giving her daughter some tips on how
to give a more effective hand job, Caleb worked his magic fingers, massaging
their cute butts to their great delight. When Sara slipped his cock into her
small mouth for the second time that night Caleb couldn't resist fondling her
pussy for the first time. Sara's groans were muffled by his hard cock as he
expertly worked on her gorgeous mound.

As Ashley could attest to, Caleb was much more than just a
good lover, he was an expert. He studied everything he could find about the
wonders of the female body and all the paths that led to its ultimate pleasure.
His knowledge and skill translated well to Sara's teenage body and soon his
fingers were dripping with her pussy juices. He easily slid his middle finger along
her cunt slit, her pussy lips slipping along the sides of his finger as he
gently rubbed up and down the entire length of her young wet cunt. He'd rest
the tip of his finger just below her tiny asshole and then slowly slide it
forward across her virgin opening stopping for a quick rub against her little
clit before reversing course and doing it all over again.  It was driving
Sara wild, but she valiantly kept up her work on his raging cock, determined to
not get distracted.

Sara was a quick learner and even though Caleb had just had a
massive orgasm, her mouth and tongue were bringing him close to cumming once
again. Incredibly turned on, he knew he couldn't hold out much longer and
wanted to save his next load of cum for her virgin pussy, so to distract her
from her amazing blow job he pulled his finger back and instead of gliding it
over her fuck hole like he had been doing he angled it up and let it slowly
enter her hot, wet, tight eighteen-year-old pussy.  As he suspected he
felt no resistance as he had assumed Ashley's sex play had already broken
through her hymen, and, also as he suspected, it had the desired result on her
blow job as she gasped and shivered with joy, causing his nearly orgasmic dick
to slip out of her mouth. But it was only a brief respite as she quickly
latched back on to his cock and began sucking away in earnest.  His dick
ready to explode, he decided to pull out all the stops and twisting his finger
inside her tight cunt so his palm was facing down, he curled his finger and quickly
found her g-spot. Sara immediately lost her ability to continue blowing him as
Caleb rubbed her pleasure spot with his expertly trained finger while at the
same time massaged her tiny little clit with his thumb. In a matter of seconds
she was cumming hard, her head now resting on the bed, her hands tightly
grasping the blanket as waves of bliss cascaded out from her orgasmic pussy.
Juices were pouring out of her sex, running down Caleb's arm and streaming down
her skinny legs as she moaned loudly in the throes of the biggest orgasm of her
young life. Eventually her knees slid back and she let her body collapse on the
bed next to Caleb.    

“Wow, what did you do? That was really great!” Sara panted
after she had finally recovered.

“It's called a g-spot. It's a super sensitive bundle of
nerves that many believe are an extension of the clitoris and if you know where
to look you can send most girls into heaven.” Caleb responded slipping his
finger out of her pussy and gently stroking her cute little ass, leaving trails
of her pussy juices behind.

“I told you he was an excellent lover, didn't I?” Ashley said
smiling over at Sara. 

“Can we have sex now?” Sara said as she sat up and began
running her fingers up and down Caleb's still rock hard dick.

“Sure, hop up here,” Caleb said happily, patting his lap.

Sara let out an excited little scream and quickly crawled on
top of him, her thin legs straddling his waist, her still wet sex pressing
against the middle of his penis.

“Now I want you to be in total control, okay?” Caleb said.
“Put your hands on my chest and go at your own pace. If you feel any discomfort
we can stop at any time, okay?”

“Okay,” Sara said breathlessly as she raised her pussy to the
tip of his stiff member.

Ashley held the base of Caleb's penis and guided it towards
Sara's waiting fuck hole. With just the very top resting against the entrance
to her virgin pussy Caleb could already tell it was going to be a tight a fit,
her weight already partly being held up by his huge hard cock. But with her
copious juices already in full flow the top of his dick was quickly
well-lubricated as she rocked back and forth. She slowly let more and more of
her weight down on top of Caleb's cock until the head suddenly popped inside
her.

“Oh!” Sara said surprised.

“You okay?” Ashley asked putting her hand on Sara's shoulder
to steady her.

“Yeah, yeah, feels freakin' awesome, just surprised me,
that's all.”

After the head was inside her the rest was pretty easy as
Sara just let her body slowly slide down on Caleb's big hard cock. Caleb and
Sara and Ashley watched as his huge dick disappeared inside of the tight teen's
pussy, stretching her pussy lips obscenely around the girth of his stiff penis.
Inch after inch was engulfed by her fuck hole, and every time Caleb was
positive she couldn't take anymore, she sunk down a little bit more until she
was finally sitting all the way down at the base of his cock.

“How's it feel,” Ashley asked, her eyebrows raised
expectantly.   

“Pretty cool, I can feel it way up here!” Sara said pointing
at a spot just below her bellybutton. “How’s it feel, Caleb?”

“I've fuckin' died and gone to heaven, Sara!” Caleb said
almost out of his mind with pleasure. “Can you feel this?”

Caleb flexed his kegel muscles causing his cock to jump deep
inside Sara's tight wet pussy.

“Oh! Yeah, wow, you can make it move!”

“Yep,” Caleb said and did it a few more times each time
causing Sara to squeal with delight.

“Here let's try this.” Sara said as she carefully rose up,
gently letting Caleb's cock slide a little ways out of her pussy before just as
carefully lowering herself back down again.

“Oh, God, Sara, that feels so, so good!”

“Really, it feels super good for me too! You want me to do it
some more?”

“God, yes!”

Sara rose up again this time letting a bit more of his hard
thick cock slip out of her drenched pussy hole before again impaling herself on
Caleb's stiff rod.  And again, she pushed herself up a little faster this
time, but back down just as slow as before. Sara kept doing it until she found
a nice slow rhythm, always keeping her down stroke slow, but rising up faster
and farther each time until she was coming up to the top of his cock each time
and then slowly forcing Caleb's hard dick back up inside her snug pussy. Just
before Caleb couldn't take much more Sara accidentally came up too far causing
the head of his hyper sensitive dick to literally 'pop' out of her cunt. With
Ashley's help she quickly popped it back in and as the bulbous head moved past
her g-spot Sara went over the top in a mind-blowing orgasm. Caleb couldn’t take
it anymore and grabbed her hips and sunk his raging hard cock deep inside her
pussy and began to fuck her like she was some sort of delicate sex doll. It
wasn't a hard or fast fuck by any stretch, but he was certainly fucking her at
a quicker pace than before. Sara was cumming hard, her thin body convulsing
every few seconds in yet another orgasm, her already tight cunt contracting
wildly around Caleb's thrusting penis until he finally could not hold back any
more and erupted deep inside her body. His cum poured out of the tip of his
cock suddenly filling Sara's tight cunt so completely that with every stroke
the white goo was forced out around the edges of where his cock and her pussy
lips met. Cum sprayed and splattered as his hungry dick continued to refill
Sara's fuck hole, his juices getting forced out as his big cock repeatedly
slammed inside her. Again and again Caleb kept fucking her until she finally
stopped cumming and collapsed on his chest, her pussy still firmly planted at
the base of his now empty, semi-hard cock, trapping it inside her still
occasionally spasmodic pussy.

It was almost five minutes later that Sara finally spoke.

“That was awesome!” She said breathlessly, “When can we do it
again?”

“It was only a few weeks after that that Jacob and I had sex
for the first time and our little group began.” Sara explained to Holly after
telling her the story of her first time with Caleb. “I was also still having
sex with Ashley and Caleb a few times a week until you came along.”

“I guess I can see how that would have made you pretty
jealous of me.” Holly said sadly.

“Yeah, at first I was, but like I said I wasn't in love with
Caleb like Ashley is, like we are. To me it was just amazing sex and I had my
friends and Ashley, who was so sex starved without Caleb that she was
practically wearing me out, so I wasn't deprived of sexual release ... but I
have to admit, sex with Caleb was impossible to replace.”

“So you don't have sex with him now, even though he's back
together with Ashley?”

“Nope, he didn't think it was right because you're my best
friend. He told Ashley how much he misses me in their bed, but he just refuses
to do anything that might hurt you. And to tell you the truth I didn't want to
either cause I don't want to have to keep secrets from you.” Sara explained.

“But now I know and I don't want you to be deprived of his …
good sex.”

“No. I would feel too weird, like I would be stealing
something away from you.”

“No, really, I really want you to. I mean, I … I … wish that
I could …” Holly said softly.

“Really, well, why don't you?”

“What? I can't just go up to him and ask for sex.” Holly said
shaking her head. “He would never go for it.”

“Maybe your right,” Sara said and then smiled knowingly. “But
I bet I know another way, if you don't mind sharing.”

Over the next few days they fine-tuned Sara's plan. The basic
idea was to get Caleb to witness Holly and Sara having sex. If he reacted
anything like he did when he walked in on Sara and Ashley, he would be
powerless to refuse.

They set it up to happen over at Sara's house on a typical
Ashley/Caleb date night, but for their plan to work they would need to get
Ashley over on to their side. This was easily done as, much to Holly's
surprise, Ashley already knew about Sara and Holly not to mention Jacob and
Brian and Sasha and Katie. As Sara explained it, “Ashley and I have no secrets
… well except for you know … the porn stuff.” Plus, Ashley was already a strong
proponent of being open-minded sexually and since Holly wanted it so badly she
certainly saw no harm in helping get Caleb over his possible hang ups,
especially if it meant that Sara could join back in the fun and hopefully Holly
too.

Caleb and Holly spent most of the day helping Ashley and Sara
with their house projects as they had been doing two or three times a week
since Caleb and Ashley had gotten back together. When they finished for the day
Caleb and Ashley started making dinner and Sara and Holly ran up to Sara's
room. After about 45 minutes, the cooking was nearly done, the table was set,
and all that was missing were the girls.

“Could you go get the girls for dinner, Caleb?” Ashley asked
doing her best to suppress her excitement at what awaited him.

“Yeah, sure,” Caleb said as he dried his hands on a dish
towel and headed off to Sara's room.

As he disappeared down the hallway Ashley quietly followed,
not wanting to miss any of the fun.

“Hey girls, time for dinner.” Caleb said as he opened Sara's
bedroom door and suddenly stopped dead in his tracks.

The sight before his eyes nearly caused his penis to rip
right through his shorts. The beautiful eighteen-year-old year old Holly and
her equally gorgeous twenty-year-old best friend were sitting at the head of
the bed completely naked, knees bent, legs spread wide, thrusting large dildos
into each other’s pussies. They both looked up at him in mock shock, but
quickly smiled and resumed fucking each other with their matching purple fake
cocks.

“Caleb you're just in time. Holly was just telling me how
much she wished this dildo was your hard cock.” Sara said with a breathless
smile.

Caleb couldn't move ... the beauty and outright sexuality
being displayed before him was almost too much to bear. He knew all about
Sara's unforgettable body as it was one of the hardest thing he had ever done
when had refused to sleep with her anymore, but sexy young Holly, the very
reason he felt he had to shun Sara from his bed, was a new revelation. It
wasn't because he had never thought of her in that way, his head had filled
with fantasies for the moment he met her, it was just that he never thought she
was in tune with her sexuality in such a dramatic way.

He just stood and stared at the two naked young women
pleasuring each other with such abandon. Sara, her slightly curly shoulder
length blond hair framing her angelic face, her piercing blue-eyes filled with
lust and mischief, her small perfectly round breasts, her toned lean body, her
tight bare cunt being stretched wide by Holly's thrusting dildo, and her
perfect ass half hidden by the bed, but still sharp in his mind. And of course
the lovely, Holly, a few inches taller than Sara, her shiny light brown hair
cut short just below her ears combined with her long legs and skinny body made
her seem almost pixie-like. Her breasts were perfect handfuls of heaving hard
youthful sexuality, her two little pink nipples sticking straight out, the
journey down her flat belly and waist was almost uninterrupted by her skinny
hips leading down to her small tight ass and gorgeous cunt that was currently
being filled by the latex dildo being pumped into her lean frame by her best
friend. Her brown eyes were sharp and locked on to Caleb's with pure lustful
intentions.

“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.”