Tim and Jill - The Beginning
Preface
It would be fair to say that the first time Tim laid eyes on Jill, he
definitely did not fall in love with her. Now that we've got that out of the
way, what did cause Tim to settle down with this mousy product of a
dysfunctional family? How did Jill go about capturing the heart, not to mention
the mind and cock of this master of the short cut? Why would a man who managed
to graduate college without ever taking a final exam want to spend the rest of
his waking hours coping with one of the most naive human beings ever to draw
breath? Why would a man who could charm the panties off all but the most
dedicated adherents to the lesbian persuasion want to occupy the same bed with a
woman who at best was average in looks and had more hangups about sex than a
roomful of spinsters? To get the answers to these questions you'll have to wade
through the following chapters that cover that period when Tim was foot-loose
and fancy free and Jill was just loose, compliments of Tim's guidance and
advice. No, in case any of you are speculating that this will be another version
of Candide; nothing could be further from the truth.
Chapter 1
Tim Taylor had been invited to a sorority pledge event to check out the
new talent, or was it meat? He could never keep those two concepts straight.
Although not considered a scholar, he was still well-known for his talent for
cutting corners and doing things the easy way. It didn't hurt that he also was
quite well endowed in the only areas that counted in the dog eat dog world of
pussy pursuit, namely the impressive size of his cock and a line of bull that
left most females dazed and confused enough to become that kind of a girl even
as they were denying it. Tim was indeed a charmer.
As was his wont, Tim consumed tremendous quantities of free beer and
scoped out the better looking members of the herd, marking those he intended to
cultivate in future times. After spending some time circulating, he decided to
visit the little boys' room downstairs in the basement. It was there that he
first set eyes on Jill Norton. The girl was naked and tightly tied to a large
block of wood with her head dangling over the edge. Just below her was a trough
that was acting as the men's urinal. He noticed that there were two enormous
vibrators churning away inside her lower orifices, and that her mouth was held
open with a fixture that must have been liberated from the dental school.
However what really caught his eye was her hairy armpits and the wildest
bush he had ever seen. This babe had probably never used a razor in her entire
life. He sort of wondered what it might be like to go down on that jungle of
unruly hair, but quickly dismissed that thought as being too ugly to
contemplate.
Three guests stood around the mousy brunette, directing their streams of
recycled beer into her open mouth. The pledge was trying her best to gargle with
the stuff, but so much was flowing into her, that she was lucky just to be able
to swallow most of it. Tim elbowed his way into the circle and jettisoned his
used beer on her bulging stomach, spraying it from bottom to top, before moving
down to give her eyes a good rinsing. He saw that they were taped open, a good
idea as far as he was concerned. It would be no fun to piss into her eyelids. He
also managed to shoot some of his yellow stream up her nostrils, bringing some
applause from the onlookers waiting their turn to drown the pledge in recycled
beer. When he was done, Tim zipped up and went about his business, leaving the
girl to the tender mercies of the line of guys waiting to use her as a urinal.
The next day Tim got a call from one of the pledge mistresses who asked
him to meet with her to discuss a problem they were having with a pledge. Always
one to play the angles, Tim decided to go over and check the situation out. He
just knew that if he played his cards right there was some pussy to be had. He
was hoping the topic of the discussion might be one of the frosh that he had
identified as potential prey. Such was not the case, instead it turned out to be
Jill Norton, the daughter of retired general Nails Norton, one of the most
famous graduates of the college. When he inquired if she had attended the pledge
beer bust, he found out that he had already had a close encounter with her. Jill
was the one trying to avoid being drowned in used beer down in the basement. You
talk about your small world.
Tim did his best to conceal his disappointment, after all that little
piss pot was definitely not his cup of anything. However he continued to
politely listen, feigning interest, when actually he was looking around for some
fresh meat. He nodded and mumbled something under his breath as he learned that
Jill's mother was also a member of the sorority, having held the posts of
sergeant at arms and pledge mistress during her days as an active member of Phi
Upsilon Kappa.
A legend in her own right, the former Gwen Goodbody made no bones about
the fact that she went both ways and during her four years at the college had
bedded down with all the attractive lesbian sorority girls and nearly half the
male faculty, including their wives in many cases. It was even rumored that Gwen
had been the secret sex-slave lover of the Dean of Women. That got his
attention. Considering her blood lines, where had Jill gone wrong? His devious
mind began working as he focused on what the pledge mistress was saying.
"Jill's not smart enough to be a nerd girl, and she's certainly lacks
the beauty and body that we look for in our sorority playgirls. We've got our
quota of top pledges that we really want, and some of them go both ways as well,
something else that Jill doesn't do either. What we need is someone to take her
off our hands, so to speak."
Tim let loose a series of little grunts as he addressed the problem and
tried to figure an angle that would solve the pledge mistress' dilemma. He had
been quite taken by her zaftig build in the past and knew that handling this
matter would also get him into position to handle her bountiful curves to his
heart's content. Tim was a simple man when it came to pussy; all he wanted was
to get as much of it as was humanly possible while he matriculated at the
college. He liked to use that word "matriculate", it made him feel smart, like
those nerdy college types that looked down on him unless they needed a favor,
such as him providing an easy lay for them from his famous Directory of
Depravity. Naturally this type of favor always required some kind of quid pro
quo, which was how Tim managed to avoid ever taking any kind of examination.
Tim knew that his client would probably expect him to step up to the
plate on this one provided she delivered the goodies. However taking on Jill
Norton was the last option he would consider. The one before that option was to
leave college and become a monk. At that point he threw out a line to gauge the
seriousness of the situation. So he grunted and scratched his head before
asking, "Why not just kick her ass out onto the street and hope some sex-crazed
nerd will take her away?"
The pledge mistress, her name was Sindy and at times she certainly lived
up to the first three letters of her name, heaved a sigh, causing Tim's lips to
quiver at the prospect of suctioning those big soft mounds until his face was
covered with cream. "No can do, her dad, the general is too well connected and
Gwen would have our heads. We need some way to make her leave voluntarily."
Tim's brow furrowed; based on what he had witnessed down in the basement of this
sorority, Jill wasn't about to go away easily. Then the light went on.
He slapped his knee and grinned that crooked grin that had brought more
than one coed down to her knees. "I've got it! Turn her into the sorority fuck
pig. Volunteer her for every keg party on campus. Put her phone number on the
wall of every men's room in town, and make sure she answers every call. Tell her
its part of her initiation because she is being considered for a special, but
secret, sorority honor that even her mother never received. Tell her if she
fails, she can never become a full fledged member of Phi Upsilon Kappa." Tim had
often heard this sorority referred to as the fuck sorority, but never made the
connection to the Greek alphabet.
Sindy's face broke into a huge smile. "Tim, you have saved my ass, and
as a reward you can have as much of it as you can handle on any night of your
choice this week."
Tim grinned and grunted happily before upping the ante. "I'll be
expecting you and that hot little freshman friend of yours, what's her name
again?"
Sindy blushed and shifted that curvy body to give Tim a glimpse of her
bikini panties as she answered, "Her name is Candy, Candy Sugartwat"
Although somewhat distracted by the view of Sindy's plump pudenda
stretching the fabric of those brief bikinis he quickly replied, "I'll be
expecting you and Sugar, or is it Candy, over to my place no later than seven
sharp this evening. Rumor has it that your little buddy goes both ways. I want
to see you and her give me a good show before I nail both of you to the
mattress. Now don't tell me she doesn't do that kind of thing, I have photos
that seem to indicate that she does. In fact I'm going to pin them up to the
headboard to make her feel right at home." Sindy bowed her head and heaved
another sigh. The ever resourceful campus con man had struck again.
Tim's off-campus digs were the stuff of legends. Three years ago he got
lucky and sublet the below street level efficiency apartment from a guy going
off on a trip to Europe for three months. The trip turned into a five year stay
in a Turkish prison as the result of some bad decisions the guy made. Tim's
little nook, also known to the movers and shakers on campus as "The Basement",
was the place to go at least once if a young girl aspired to be anybody of
importance on campus. Over the years it had become the place to sacrifice one's
virginity, a sort of rite of passage for the more daring and adventurous types,
especially those well endowed in body, but slightly lacking in brain cells,
Tim's lawful prey.
The apartment, such as it was, consisted of one large room and a small
adjoining bathroom which usually reeked of stale piss and vomit. On occasion Tim
would con some gullible freshman girl to come in and clean up the mess in
exchange for a chance to become famous as one of his conquests. Tim had actually
made a stamp that he used to validate his sexual liaisons. Among his growing
collection of bedmates it was considered chic to have his fingerprint and a low
number imprinted on one's left ass cheek. Woe to those who attempted to
counterfeit this stamp, they were always ostracized from the in-crowd activities
once their dirty little forgery was exposed to black light. Tim had thought of
everything it seemed, even deliberately setting aside a bank of low numbers that
would be used for those future ladies who performed up to his high standards.
The dominant piece of furniture in his room was the bed, a king-sized
affair covered in the finest sheets, blankets and coverings, compliments of his
many satisfied partners. This too had become a campus ritual and a most
profitable one at that. Tim received so many tokens of appreciation that he
never had to wash anything. In fact he had a thriving business selling these
rumpled signs of his sexual prowess as mementos to those who had assisted him in
these delightful endeavors. Above the headboard was the scoreboard, a chronicle
of his conquests, rated from one to five stars.
Across from the bed was a large screen television set, a gift from one
of his admirers, a female professor who wanted to remain anonymous although she
had mussed the sheets with him quite often during his first year on campus.
Sitting next to the set was his video tape recorder, one of the newer models
given to him by the wife of the store owner for services rendered. Tim felt it
was a fair trade since she was on the wrong side of thirty. Privately he did
admit that she had a very well preserved body and had taught him one new trick
that aided him quite often in his bedroom battles.
It was the collection of video tapes that was Tim's pride and joy. He
had dozens upon dozens of tapes of many of the hottest pieces of ass that had
occupied his bed. Most either were happily masturbating in anticipation of a
horsey ride on his giant cock, or giving him head in appreciation for a job well
done. There were also a small number of tapes capturing one of his partners
intimately entwined with a second participant, doing some sort of nasty and
novel thing with their tongues, fingers, mouths, and on rare occasions a
fist.These were the threesome tapes that he treasured above all. Tonight he
looked forward to the opportunity to add to this special category.
To complete the decor there was a large refrigerator, always well
stocked with beer, next to a small table holding a hot plate and coffee maker.
The appliance had a story attached to it as well, but Tim could no longer
remember who sent it to him for services above and beyond the call of duty. The
two small windows that used to allow a few rays of light to enter this dark room
had been boarded up to prevent those consumed by curiosity from peeking in on
Tim as he went about his business of pleasuring the girls lucky enough to be
allowed entrance to his kingdom. His clothing was strewn around the room in
random fashion, along with numerous pieces of underwear left as mementos by
those delighted with his servicing.
Promptly at seven o'clock the buzzer sounded. A few minutes later Tim
was sitting on the bed shooting some pictures as Sindy and Candy posed while
removing their clothing. Tim was delighted that they wore identical underwear, a
sign that they were a couple, at least until pledge season ended. Sindy's 38DDs
were spilling out of the sheer taupe colored fabric of her bra, the material
being stressed to its limit by her heavy melons. Candy in contrast was almost
boyish compared to her full figured companion.
The frosh's pert tits bounced free of the bra, and she posed with hands
on hips, a big smile on her face. Tim waited until Sindy's awesome boobs escaped
from the confines of her bra. Then he posed the two with Candy reaching from
behind Sindy to heft her stupendous jugs in the palms of her hands. Next he had
Candy kneel on the bed and put her face to Sindy's crotch as it came into view.
It was smooth as a baby's behind, but the fat cunt lips and the prominent
clitoris that capped the top of her snatch gave proof that this was a cunt that
was made for eating and fucking. Between Candy's tongue and mouth and his hard
cock, that hot box would get all it could handle before this evening was done.
Little Candy's pussy proved to be a revelation; she had let her pubic
hair grow. Miss Sugartwat was a natural blonde and proud to show off that fact.
Tim grunted his approval and got a nice shot of Sindy's tongue probing the
little blonde's coochie. He decided it was time to sample the merchandise and
instructed his two "dates" on how he wanted them arranged to get things off to a
fast start. Candy was assigned to hoover his cock into maximum readiness while
Sindy was providing him a sample of her plump pussy. Tim had hardly gotten
started when Sindy let out a whoop and a holler, then shouted, "Where did you
learn to eat pussy like that?" Tim was too busy worming his tongue deeper into
her juicy hole to give her an answer. In all candor he never intended to reveal
to any living soul what he went through one summer at his maiden aunt's home on
the lake. It was there over a period of two weeks that she taught him the
rudiments of sex, her way, the hands-on approach. To this day he always wondered
how he ever survived that boot camp from hell.
Things went very well for the threesome. Tim made a number of deposits
into both girls, including a monster load that flooded Sindy's bowels and made
little Candy gasp with amazement. She was still an anal virgin at that time. An
hour later Tim had her anal cherry posted on the scoreboard. Sindy was
everything that he wanted from a babe, she really knew how to move that big body
and doing her was like riding in a luxury car, smooth and comfortable. What
little Candy lacked in skill she made up for with enthusiasm and a flexible,
athletic, youthful, hard-body that her companion could not hope to match. To
Tim's way of judging these two made up a four star pair and it was duly noted on
the scoreboard right after he stamped their butts with his famous seal of
approval.
There still was time for Tim to shoot some footage of the two girls
going at each other. He took out his trusty video camera, another gift from one
of his older fans, and proceeded to record this meeting for posterity. Sindy and
Candy put on a great show; it was obvious that this was not their first time
together. He caught Sindy's fast tongue lapping away at Candy's little starfish
as the young blonde held her cheeks wide to give her lover every opportunity to
tickle every square inch of that sensitive region. He got some great footage of
Sindy straining Candy's pubic hair in order to poke her tongue into that hot,
juicy hole that had steadily oozed cooze cream for the entire night the three of
them went at it. He even managed to record little Candy sucking part of his
monster load from Sindy's asshole and then the two of them taking turns
transferring it back and forth from each other's mouth. For the grand finale
Sindy noisily sucked up every drop of the by-now watery deposit from the
teenager's hard nippled tits.
(To be continued)
