Kelli and Bill
“Cum Diaries” Story)
Diaries" are occasional fictionalized accounts
of stories told to me by my readers, in this case of my short
story “Best Ever”.
That began an ongoing conversation with KT in North Carolina
about her experiences.
Spring turned to
summer and school ended for the year. Bill planned on leaving
for college in late summer, with his father taking some
vacation time to drive him across country.
They lived near a
state park with a popular beach and, since they had the entire
weekdays to themselves, Kelli and Bill would often spend warm
afternoons there. Kelli had outgrown the one piece swimsuit
she had the previous year. After considerable badgering, she
finally convinced her mother to get her a cute two piece that
was not exactly a bikini but did tend to emphasize her round
firm butt. While the beach at the lake was often crowded, only
a very few braved the cold water, especially early in the
It took a dare, but
after barely standing in the edge of the water, they took each
others hands and ran in until they were completely submerged,
yelling and screaming their protest as the frigid water
engulfed them. While the water only came up to about Bill's
belly button, it covered Kelli's little tits, making them
stiffen even more.
let's get out now,” she complained as Bill wrapped his
arm around her waist and pulled him close.
he laughed, thumbing her erect nipples just below the water
level, “I want to try something first.”
Her step brother
reached in front of her and slipped his hand inside the
waistband of her bottom, sliding his finger down until he
split the taut fold of her pussy lips.
Kelli cried out, “What if someone sees?”
“No one can
see,” he murmured into her ear, flicking his tongue
across the lobe quickly, “no one is nearby and we are
under the water.”
Kelli moaned lowly as
his finger circled her developing clit, a familiar tingle and
warmth growing between her legs. As she pressed her cunt back
against his finger, Bill slipped his other hand down her back
and under the swimsuit to swirl a finger tip around her tight
Bill cooed into her ear as she pressed her body back against
him, rotating her hips to maximize the touch of his finger on
her clit and anus.
much...now,” she gasped, throwing her head back against
Bill took his hands
out of her swim suit bottom and pushed his own suit down
enough that the waistband hooked under his balls. Then he took
Kelli's hand in his and placed it on his shriveled up dick
before putting his fingers back on her clit and asshole.
happened...you're so soft...and small?” she asked when
she took his dick into her small hand.
“It's the cold
water, does that to a guy, just like it makes your nipples
stiff,” he explained and started rubbing her clit a
little faster. “I'll tell you what, we'll get out of the
water after one of us makes the other one cum.”
“I'll win that
one today,” she grinned back at him, her entire body
trembling when she clamped her legs around his hand and
climaxed on his fingers.
Over the course of the
summer, they went to the lake almost every day, always
separating themselves from the other swimmers so they could
play with each other until one or both of them would cum. As
the water warmed, Bill would shoot his jism through her
fingers into the water more often than Kelli but he would
always make up for it when they got home, with his tongue and
lips on her clit and a finger, and eventually more, in her
One day towards the
end of the summer, they were walking home from the beach in
silence. Neither of them wanted to think about the fact Bill
would soon be leaving for college on the other side of the
country. Finally, as Bill fumbled with the lock on the door,
Kelli asked a question that had been bothering her for a
“When are you
going to fuck me...for real...not just with your fingers?”
she exclaimed, looking at him defiantly with her arms crossed
under her tits.
Bill turned and looked
down at her, a bemused expression on his face.
that's something we should be talking about out here on the
porch, for the neighbors to listen in...maybe you want to ask
Mrs. Watson next door her opinion too?” he smirked and
walked into the house.
Kelli blushed and
hurriedly looked around before following him into the house.
He dumped the bag with their wet towels in the laundry and got
himself something to drink.
Kelli insisted, positioning herself directly in front of him
as he sat on a stool at the kitchen counter, his dick
stiffening as he considered his pouting step sister and her
“I told you a
long time ago, I won't fuck you in your pussy. You need to
save your cherry for your true love. Besides, I prefer ass
play in any case.”
love you,” Kelli whimpered, looking up at him with tears
brimming in her eyes.
“And I love you,
too, but not that way and we can never be together. You know
that,” he said kindly as her lips began to tremble.
Bill pulled her close,
kissing her cheek and neck as she began to cry. Then he pushed
her back enough he could look her in the eye.
“I'll tell you
what, how about we see if my hard dick can fit into your tight
asshole,” he said softly, then scooped her up and
carried her upstairs over his shoulder.
Kelli squealed in
delight as he threw her down on her bed and unceremoniously
ripped off her shorts and panties. As he pulled his own shorts
down she took off her shirt and lay back with her legs spread
wide. She knew he liked seeing her pussy gape open as much as
watching her play with her clit.
Bill's cock was
throbbing as he dropped to his knees and pushed her finger
away from her taut pink slit with his tongue. Kelli pulled her
legs back, giving him an unobstructed view and path to her
tight little anus.
He looked up at her
and grinned, his finger snaking toward that puckered asshole
while he continued to lick her pussy and suck on her clit.
Ever so slowly he gently pushed one finger into her. Kelli
quickly relaxed, having learned from him before how to enjoy
one finger filling her.
he asked as the second knuckle penetrate her tight sphincter.
Ever so slowly, he
began rotating his finger inside her asshole while at the same
time pushing it in and out. He spit on her anus and with the
tip of the first finger just barely inside her, added the
second, pressing in deep until both fingers were as deep
inside her as he could manage.
he murmured, “tell me if I'm hurting you.”
feels good...so good...don't stop,” Kelli gasped,
surprised by the intensity of the pleasure surging through her
“Play with your
clit,” he instructed her as he pulled his face back from
her pussy so he could get a better look at what was happening.
Kelli immediately started to rub her throbbing clit, her legs
trembling as the first hints of the coming orgasm surged
through her body.
Bill added a third
finger, stretching her asshole much more than ever before.
Kelli cried out as the third finger plunged into her and then
started flailing her hips wildly, a massive orgasm engulfing
her body. Bill just held his fingers inside her as she
thrashed around on them, waiting until the initial wave faded.
she screeched, rubbing her clit even harder as a second orgasm
built even before the first completely faded.
He pulled her to the
edge of the bed and pulled his fingers out of her ass, rubbing
the throbbing tip of his cock up and down in her pussy slit
even as she continued fingering her clit. He positioned his
hard dick on her anus and pushed, trying to spread her
sphincter by pulling her to him by her hips.
Her asshole was just
too tight for his thick cock head to penetrate. Besides, he
was so very close to cumming himself. Kelli squirmed around
and Bill tried as best he could but he just couldn't slide his
dick into her anus before he started cumming, rubbing his cock
up and down in her slit as he sprayed his jism all over her
belly and pussy.
try again,” her muttered into her ear as they lay
cuddling together for a few minutes, “I have an idea how
to make it work.”
They heard her mother
call up from the kitchen and quickly got out of bed. Bill
grabbed his clothes and hurried to his room, turning back at
the door to see Kelli scooping up his cum from her belly and
pussy slit and licking her fingers clean.
The next day was gray
and rainy, certainly not a day they could head for the beach,
but just perfect for lazing around the house and finish
getting Kelli's ass properly fucked for the first time. They
both squirmed uncomfortably at the breakfast table, her mother
seemingly taking forever to leave for work.
As soon as the door
closed, Kelli jumped up and pulled off the panties she was
wearing under a long, loose t-shirt. Bill put his hand on her
arm and pushed her back into her chair.
“Just hold on
for a minute, in case she comes back for some reason,”
he said with a wicked smile and picked up her panties, holding
them to his nose while taking a deep breath.
“You didn't wipe
yourself very well this morning,” he sighed and took
another deep whiff of the crotch of her panties.
“I'll pee all
over you if you want but first you have to fuck me!” she
practically screamed at him, rising again from her chair.
Bill scooped her up
and put her over his shoulder again as she squealed and
squirmed, Her t-shirt rode up and he gave her a couple of
playful slaps on her bare ass as he carried her upstairs, this
time to his bedroom.
They both quickly
stripped and Bill rummaged around in the nightstand drawer
while Kelli lay on his bed fingering her clit. He pulled out a
small jar and turned to Kelli.
she asked as he unscrewed the lid and dipped a couple of
he answered, “I use it to jerk off sometimes, makes my
dick slipperier. Now get on your hands and knees with your ass
in the air.”
Kelli did as she was
told, lowering her head so her ass was raised facing him. She
felt his fingers rubbing across her asshole, sliding easily
into her with the gooey material covering them. He gently
pushed one finger into her ass and she grunted slightly. The
second and even the third went in easier and deeper than the
“Hmm, that feels
good,” she cooed, pressing her hips back against his
Bill spread the
Vaseline all around her puckered ass hole and as far inside
her as he could manage. She looked back when he pulled his
fingers out of her and watched as he lathered up his rigid
he asked, as he dragged the head of his cock up and down in
her pussy slit.
yes...please...do it...please...fuck me,” she groaned
and reached down to rub her clit, feeling his cock brush over
First he spread her
ass cheeks with his hands, causing her tight puckered asshole
to stand out, Then ever so gently he pressed the rigid head of
his cock onto her anus. She gasped when just the tip
penetrated the sphincter and he stopped for a moment.
Suddenly, he slipped
deep into her bowels, filling her in a way she had never felt
before. Her back arched and she cried out as he just held
himself buried inside her.
god...oh...oh god...that feels...so...so...good,” she
shrieked and firmly pressed her ass back against his cock,
Ever so slowly, Bill
began pumping his dick in and out of her asshole. Kelli
shrieked and fingered herself to one orgasm after another,
each time clamping her ass around his cock. Finally, he could
hold back no longer. With one final deep thrust, he grunted
his cum into her bowels then rammed his cock in and out of her
as hard as he could until he final softened and slipped out of
Kelli knelt breathing
heavily, a rivulet of his cum oozing from her asshole and down
“Are you OK?”
Bill finally managed to ask when he again caught his breath.
His step sister pushed
herself up on her elbows and grinned over at him before
crawling up on his chest and ramming her tongue into his
mouth. Bill could feel his cock stiffening as the kiss
was...amazing,” she cooed and kissed him again deeply.
“I have never cum that good...on my fingers,,,or
yours...or even your mouth.”
With that she reached
down and fondled his cock, sliding down to lick his balls and
slide a finger of her own into his ass. Bill's dick stiffened
again and Kelli looked up at him with an impish grin.
“Are you ready
to fuck me in the ass again?” she moaned and rolled back
on her hands and knees next to him.
The next time, her
asshole was already stretched and her bowels coated with the
Vaseline and his cum. Bill took his time, bringing her to at
least two body spanning climaxes before once again filling her
with his pasty jism. Afterward they lay cuddled together in
the afterglow of their orgasms.
“That felt so,
so good,” she whispered into his ear, “if you
promise to keep doing that to me, I'll do anything you want,
anything at all.”
Bill grinned back at
her, gave her another kiss and got off the bed. He reached
down and took her hand then led her down the hall to the
“Now about that
peeing all over me you mentioned....”
As the summer days
drew to a close, neither one of them wanted to face or talk
about the fact he was soon leaving for school. Their sex play
became more manic, trying to get as much of each other as they
could in the little time remaining.
Kelli insisted on
getting ass fucked as often as he could manage. After a little
experimentation, they settled on a favorite position where she
would straddle his hips and lower herself down until his cock
was buried as deep as possible in her ass. That way, he could
twist and twirl her growing nipples while she could rub her
own clit until she couldn't cum any longer.
The last day they were
home alone, she cried even as he fucked her ass and she sucked
his dick hard again. One last time, she begged him to fuck her
in her pussy but once again, he refused.
That evening, Bill and
his father loaded up all of his stuff in a small rental truck
they would drive across country. After he was settled, his
father would fly back home. That night, Kelli could hear her
mother and step father's headboard softly banging against the
wall in the bedroom down the hall. She just knew Bill was
jerking off across the hall and so wanted to spend his last
night in his bed, with his dick in her hand or ass. She
fingered herself to an unsatisfying orgasm before falling
Two days after Bill
and his father left, her mother took her out for a nice dinner
at a good local restaurant. She tried to keep up a good front
but Kelli really didn't feel much like celebrating her twelfth
Kelli stepped out of
the Lyft car and took her bag from the driver. As he drove
away, she looked around, the house and the entire neighborhood
a bit more shabby than her last visit about two years before.
She climbed the steps
and rang the bell, waiting patiently for a few moments until
the door opened wide. Bill grinned down at her, a little
thicker and a lot grayer than the last time she saw him. Then
again, so was she.
he grinned and threw his arms open wide, “it's been way
She melted into his
arms, pulling him close, inhaling his musky scent as he
snuggled against her neck. After a moment, he broke off the
embrace and stepped aside so she could enter the house. Not
much had changed inside either, just looking a bit more worn.
As Bill picked up her
bag, another man walked in from the kitchen. He was short and
slight and looked to be in his mid to late thirties.
“Kelli, meet my
husband, Chad,” Bill said putting his arm around the
guy's shoulder, “and Chad, my step sister Kelli.”
They shook hands and
exchanged pleasantries before moving into the kitchen. Bill
dug some cold beers from the refrigerator after Kelli told
them she didn't need anything to eat.
happened exactly, your message was a bit unclear,” she
said to her step brother after taking a deep drink.
had a massive heart attack at the grocery store. They kept him
on life support until I could get here, but there was no hope
of recovery. I am glad you could come, I still regret not
being here for you when your mother passed two years ago.”
Kelli said softly, “Dad told me you were out of the
They talked for a few
more minutes before she retired to her old bedroom and fell
asleep quickly after a long day.
The next day was an
wearying blur. The funeral service at her step father's
church, followed by the procession to the cemetery and burial
and then by an exhausting parade of nearly forgotten or
completely unknown family friends and relatives she had no
doubt she would never again see.
She flopped down on
the couch with a beer as soon as the last visitor was gone.
Bill came in and sat down next to her with a beer of his own.
for coming and helping me get through all that,” he
said, absentmindedly patting her thigh. “How long can
“A few days if
you need me, I don't have anything pressing going on until the
middle of next week.”
“I do appreciate
it,” Bill said tiredly, “Chad has to leave in the
morning. I have an appointment with an attorney the day after
tomorrow and I want to get this place cleaned out so I can
“OK, I'm at your
service,” she said softly, kissed him on the cheek and
headed to take a shower and then sleep.
She was drifting off
to sleep when she heard a low thumping. It took her a second
to recognize the headboard hitting the wall across the hall.
Her brother and his husband were having sex and that thought
brought back the memories of those times he fucked her in the
ass and licked her pussy until she climaxed in that very same
bed. Kelli's pussy twitched and she buried her face in a
pillow when she began to cum almost as soon as she started
rubbing her throbbing clit.
Over the next few
days, they went through every drawer and closet in the house,
separating all the stuff into that they would just throw away,
give away or leave for the estate sale. Kelli was scheduled to
leave at mid afternoon the next day as they sat among the
boxes in the kitchen, drinking more beer.
“I don't know
how to thank you enough for all your help,” Bill said
quietly, “I don't think I could have done all this
Kelli smiled and
leaned back against the counter top drinking her beer. A
devilish smile grew on her face before she turned to face her
something I would love you to do for me,” she murmured
slyly, her bra less nipples stiffening beneath her t-shirt.
anything you want,” he responded without looking up or
“My legs are
killing me. I want you to give me one of your world famous
massages,” she murmured and put her hand on his thigh,
“just like you used to do.”
Bill turned toward her
with a surprised look on his face. Then he broke into a broad
“Sure, why not?”
he said, “go get ready and I'll be there in a minute.”
Kelli smiled back at
him and practically ran up the stairs. By the time he walked
into her room with a bottle of lotion in his hand, she was
laying on her stomach wearing just some filmy panties and a
lacy bra. She shivered when he ran a fingertip up the bottom
of one foot.
“I see your ass
has gotten a lot bigger since I last saw you like this,”
he laughed and squirted some lotion on her leg.
“Well I guess
most of me has, as well as that belly of yours,” she
retorted before letting out a soft moan when he squeezed one
of her calves.
he laughed, “so tell me, what have you been doing with
yourself all these years.”
He worked his way very
slowly up her right leg as she told him a very abbreviated
version of her marriage and divorce and a bit about her
current job. She moaned lowly when his hands almost reached
the silky fabric of her panties, deeply massaging her upper
thigh before returning to her other leg and repeating his
Kelli felt her pussy
clench as Bill worked his hands up her leg. When he stopped
just short of her panties on her right leg, she ground her
pussy into the sheet. By the time his hands reached the same
spot on her left leg, she could feel some of her pussy juices
drooling into the gusset of her panties.
“Mmm, you are
still really good at this,” she gasped and bit her lip,
practically ready to cum if he touched her pussy lips. “Don't
His hands moved up
both sides of her hips, his fingers catching in the bottom
edges of her panties and pulling them tightly into her ass
crack and folds of her now very damp pussy. She squirmed a
little, feeling the moist fabric pulling against her throbbing
clit. He leaned forward to whisper in her ear, the hard
outline of his dick pressing against her thigh.
“Should I get
these out of the way?” he murmured into her ear and
gently snapped the elastic leg band of the panties.
god...yes,” she gasped, raising her hips for him to pull
off her panties while pressing her thigh even harder against
his rigid cock.
He slowly pulled them
down, pausing momentarily when the fabric caught in the wet
folds of her pussy lips. She heard him take a sharp intake of
breath, spread her thighs even wider and looked back to see
him holding her panties to his face, inhaling the scent of her
sex with a slight hint of her piss.
Her step brother kept
her panties over his nose and grinned down at her. That's when
she saw how far out his rigid dick tented his briefs, the only
thing he was wearing. He tossed the panties aside and reached
down to undo the clasp of her bra. Kelli shrugged out of it as
she rolled on her back with her legs spread wide on either
side of her step brother.
she cooed, pinching here erect nipples as he looked down at
her, the pink inner flesh of her pussy peeking out through her
thin honey brown cunt hair.
He smiled back at her
and without a word, slipped his briefs off, his thick dick
popping straight out at her. He crept forward a little until
her inner thighs pressed firmly against the outer skin of his,
his purplish cock head mere inches from her throbbing pussy.
“You know, you
were the first, and actually the only, woman with whom I ever
had a relationship.” he said softly, starting to stroke
his hard dick.
“I was a little
girl then,” she responded and spread her pussy lips with
her fingers until the hard nub of her clit popped out, “but
now I'm all grown up.”
Kelli could see the
conflict of lust and confusion play across his face, as well
as the droplet of precum dribbling toward her hairy cunt. She
reached up and cupped his balls, drawing the tip of his dick
right up to the dripping edges of her pussy. She brushed the
head between those lips a couple of times before looking up at
there's something I wanted you to do thirty odd years ago and
I'm asking...hell I'm fucking begging...you again to do it
He looked down at her
quizzically as his entire body quivered with her touch.
“You can fuck me
in the ass and we have until tomorrow afternoon to compare my
asshole and blow job techniques to your
husband's...but...right now...there's only one thing I want
you to do...I've wanted you to do since I was eleven years
old...cum inside my pussy!”
Kelli's first orgasm
wracked her body even before his cock was buried all the way
inside her cunt.
Kelli took the Fed Ex
package from the delivery guy and sat at her kitchen table to
open it. There was a copy of a letter from her step father's
attorney to her step brother with a cashier's check clipped to
it. Apparently this was the final settlement on the estate
and, although she didn't much care, she was pleasantly
surprised by the amount.
At the bottom of the
letter, there was a hand scrawled note...”Open the
She turned the
packaging over and dumped out a plain white business envelope.
She looked at it for a second before tearing it open. It
contained an airline ticket with another note in her step
brother's handwriting pasted on the outside of the jacket. Her
pussy clenched as she read the fateful five words.
to watch too!”
do welcome any comments and will try to respond to all I get
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