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Some guys are simply born squat and butt ugly. No
point lamenting the fact either. It’s God’s little joke and no Saville-Row
tailor, academic prowess or designer high-heeled shoes, can address so
unfortunate a shortcoming.
Philip Cobbett was the epitome of unattractive youth. Wasn’t much better
when he hit thirty! The nearest he had gotten to seeing a girl naked was
Playboy’s Miss October 2006 centerfold. Why her? Simply because she hung
on the back of his bedroom door – a nightly reminder of what he was
missing in his life.
Contributing to his lack of popularity – with pretty much either sex – was
an unusually pronounced birthmark that stretched from just below his left
temple to his jaw-line. At first glance one might have taken it to be a
facial burn of some sort. There had been the offers of plastic surgery but
a combination of insufficient finance and doubts as to its ultimate
effectiveness dissuaded him from this option. Add to this, an overweight
body, peaking at five-eight, premature baldness (a genetic family trait),
poor motor-sensory co-ordination and below-average communicative
skills….and you have a template for social isolation. Philip had never
dated let’s say!
Fate however dealt Philip a way better hand just three days short of his
thirty-second birthday when he pulled down second prize in Powerball…a
creditable three-eighty thousand dollars. Didn’t make him any taller or
better looking but the Mercedes Avantgarde Coupe sitting in the company
parking lot did not pass un-noticed.
“That’s your car Philip??” cooed petite Samantha Bryden, the bimboesque
air-head in charge of copying and fax-outs. It was an office tradition
amongst the male contingent trying to decide which was the greater
numerically – her upper torso or IQ.
“Sure” he replied, “Come to dinner with me Friday night and I’ll give you
a ride in it.” Chuckling at his double entendre it was even funnier that
she didn’t notice.
By whatever yard-stick one were to use, Samantha was a ditzy teenager. But
hey, who needs intellectual extravagance when you’re thirty-two years old
and in desperate need to catch up on a decade’s lost fumblings.
Throughout the main course at Cardinals on Eighth, Philip was mesmerized
by his young companion’s heaving cleavage, aided and abetted one must
admit, by Samantha’s underwired support team that transformed the girl’s,
in actuality modest curves into a pair of dynamically rounded orbs that
even had the waiter fluffing his ‘special of the day’ lines. Admittedly he
was ideally positioned to take full advantage of the Grand Canyonesque
view on offer.
At the point she said “OK” when he asked later if she might like to
accompany him home “for a nightcap,” he was temporarily shocked
insensible, having drawn a rain-check the few times previously he had
asked any girl the same question after a group night out.
Philip’s apartment reflected its owner’s mind-set….desperate for some
female touch and just this side of chaotic.
“Whoa!” Samantha tried unsuccessfully to repress, as she entered the small
lounge-room. Philip scurried ahead of her, clearing newspapers, business
folders and two recent editions of “Penthouse” from the sofa. He wasn’t
quick enough with the latter.
“You like girlie mags then Philip?” she giggled. He mumbled some
incomprehensible reply, avoiding all eye-contact with her.
“S’pose you visit porn-sites too?” she asked, glancing at his computer on
the desk by the far wall. He looked up at her with an expression midway
along the behavioral chart - somewhere between guilty and cornered.
“It’s OK,” she added, sensing his discomfort, “I look at them too – most
girls do you know!”
Right then, he had the strongest conviction that she would probably permit
him open-ended license to indulge his wildest fantasies with her…and in
that regard, he knew he was walking a remarkably fine line.
“That so?” he muttered. “So would you look at a few with me after I get
the coffee Samantha?”
“Sure,” she replied, hardly missing a beat. ‘The guy is obviously loaded’
she figured, ‘what difference I hafta look at a porn-site or two?’ She sat
down on the sofa neatly, ensuring nevertheless that just the slightest
hint of her lilac colored panties were visible.
Quite obviously she got the angle right as Philip almost up-ended the
tray, tripping against the corner of the coffee table as he tried his best
to ignore the girl’s up-skirt attractions. He sat in the chair opposite,
pushing the coffee cup across the glass surface towards her.
“Thanks,” she whispered, heralding a momentary period of disquiet when
neither quite knew how to introduce some neutral conversational topic.
“So Samantha, how do you like working at Bowman, Link and Grantham?” he
asked finally.
“It’s OK,” she answered. “Gets a bit boring in the copy room after a few
hours, but it’s better than not having a job I guess.”
Further inanities flowed either way for a while, in dispersed with the
occasional gulp of coffee. When nothing more progressive appeared to be
happening, the girl placed her mug back on the table and semi giggled,
“You still want to look at the computer Philip?”
“Oh, s-sure,” he replied, fully grateful for her intercession right that
moment.
Seating herself alongside her host, she waited patiently for the thing to
boot up. He seemed embarrassed to proceed. “You sure you’re OK with this?”
he asked nervously.
“Who doesn’t look at porn these days?’ she grinned. I’ve even caught my
fifteen-year old sister reading sex stories on-line.”
“Really?” he said, wishing he could have been visiting the family at the
time. “She’s a naughty little schoolgirl huh?”
“Yep, daddy’s really had his hands full with us,” she answered, before
blushing at her unintentional blooper.
“I see,” he laughed, “Like that is it?” She dug him in the ribs.
“Well here goes nothing,” he announced, clicking on a website midway down
his ‘favorites’ list. Running hi-speed cable as he was, the site opened up
almost instantly.
“QTies” was aptly named. From what Samantha could see at first glance, the
majority of girls on display must have been signed-up the day after they
turned eighteen. Some she figured, had to be using fake ID, they looked so
young. The site appeared to offer multiple free galleries of the teens
behaving for the most part – very badly.
‘Angie’ for example, a small brunette posed indecently on her bed, seemed
more than willing in the first frame, to share her up-skirt treasures with
the viewer. Not just a glimpse either, the majority of her lacey white
panties were displayed with provocative intent, courtesy of those
generously parted legs and absurdly brief skirt that might have had
trouble fitting a Cabbage Patch doll.
Frame two and Angie was laying even less claim to modesty. Draped anything
but innocently face-down across the edge of her bed, she was looking back
at the camera, her bottom revealed in all its shapely contours – skirt up
around her waist and with the elastic pulled down just sufficiently that
the viewer might determine the vaguest on-set of her rear crevice. A pose
one could argue, to test the resolve of the most God-fearing father on the
planet.
Samantha glanced across at Philip. His eyes were riveted on the image. For
some reason she found this highly arousing and in other circumstances,
might have slipped a hand into her own panties. She had recognized for
years now that she was attracted to females as well as men and pictures
depicting other teenage girls either being spanked, stripped or otherwise
manhandled, turned her on big time. Like many of her sex, she fantasized
about being raped as well as watching it happen to other girls.
“She’s real pretty isn’t she?’ Philip half-mumbled, staring now at the
third picture which showed Angie kneeling on the bed in just her panties,
leaning towards the camera to display the contents of her skimpy bra
somewhat lewdly.
Samantha was feeling almost light-headed. Her companion was no
oil-painting to be sure but she was beginning to see the relevance of the
old saying “A port in any storm” and hell, there was the Mercedes
Avantgarde out front!
Viewing the fourth picture on full-screen lowered everyone’s inhibitions.
Angie, having given up all pretence at innocence was now propped up
against the bed-head fully topless and with her legs not only apart but
holding her panties far to one side, so that her lightly furred and
evidently moist vaginal lips were clearly on view to all and sundry.
Philip’s mouth was dry – Samantha’s panties at quite the other end of the
scale.
Philip turned to his visitor. “W-what would you say if I asked you maybe
to let me see your panties Samantha?” he asked with less than no hope of
anything positive coming from the question.
For a moment, the girl wasn’t sure how she felt about so indecent a
suggestion.
“You mean just my panties?” she almost whispered, still staring at Angie’s
uncovered splendor.
“Er, well yeah of course,” he stammered, “I’m not expecting you to strip
or anything ….”
“So what are you saying Philip?” she teased. “You just want to see up my
skirt? That’s soo gross!” In truth though, the idea was already somewhat
appealing to her and the thought of acting slutty like that with a much
older man, even one offering something less than hulk status, raised her
body temperature marginally.
“You’re right, it is naughty Samantha,” he wriggled like a fish on a hook.
“Just that looking at that girl’s pussy makes me really horny. Not much of
an excuse I guess.”
Angie’s pose however was having no less powerful an effect on Samantha’s
emotions. Even if she had been considering her options, the fifth picture
in the gallery lowered any inhibitions that may still have been on site.
Having shed her panties entirely, the girl was now splayed fully naked
across the edge of the bed once more, but on her back this time and by
virtue of the newly come by, yet rather cute little blonde fingering her
now, whilst her other hand was performing unsighted excesses between her
own slim legs, the general demeanor in Philip’s room was one of ‘rampant
expectancy’ you might say.
“How do you want me then?” the girl asked of her host softly.
Looking away from the screen he studied her momentarily. Damn if she
wasn’t just as sexy as the little tease on-line.
“Could you just sit on the chair over there,” he pointed to a
sturdy-looking recliner near the window, “And, well I guess, just spread
your legs a bit?”
She was fully aware that his eyes would be glued to her shapely little
rear end as she sauntered in the chair’s direction. Seating herself
comfortably, she ensured full eye-contact before parting her legs slowly.
This was more than he could believe – a girl willingly letting him see up
her skirt.
“You like?” she teased, parting them fractionally more. It was making her
so hot!
He could but stare at the sight before him. The front of her panties were
completely visible now and even as he gazed upon that frivolous indecency,
she widened her legs further still allowing him to see as far as the
waistband of her panties. Nor could he resist staring at that noticeable
indentation all the way between her legs. He became aware suddenly of the
size of the erection beneath his zipper.
“C-could I see you in just your bra and panties?” he all but whimpered.
“Posing like Angie I suppose you mean?” she teased. Not waiting for his
reply, she stood up, unzipping her skirt at the side, letting it fall to
the ground. The blouse she unbuttoned slowly before discarding it also.
“This what you want?” she giggled, standing with her hands on her hips,
watching his reaction closely.
“You are so pretty Samantha,” he stammered, “Could you maybe lean forward
a little?”
“So you can see my tits better? You’re a really naughty boy Philip!” So
saying she leaned forward sufficient that her cleavage was accentuated to
the point he could see a hint of either nipple. The erection between his
legs was almost painful. Only the fact he was still seated allowed him to
conceal the truth of the matter.
“Turn around sweetie…please,” he asked.
Knowing full well what he wanted to see, she did so. Without further
prompting she then bent over, resting her arms on the table which quite
obviously yielded up to her host an insufferably hot view of her teenage
bottom – quite as arousing as Angie’s cute derriere. Only this one was
there in his room, not an arm’s length away.
“Can I pull your panties down a bit?” He sounded like a ten year old
asking for some chocolate cake.
Instead of answering, she leaned over further and simply wriggled her hips
invitingly.
Seizing the waistband, he peeled the cotton material fractionally lower.
He was unable to stifle sounds of approval as her upper rear-end complete
with sexy little chasm, was exposed to his understandably lustful vision.
“Don’t pull them right down…please?” she cried out, some might say at this
stage – hopefully.
Acceding to her request, he left them at half mast and fully ignorant of
his obviously aroused condition, walked around the table where the view
down her push-up at that angle was nothing short of awesome!
Philip’s expression right that moment touched the girl. Far from a virgin
herself and despite the fact she was basically acting like a hoe to
further her own financial gain, just the sight of that livid birthmark and
his now quite obvious state of arousal, tripped her compassion meter.
“Do you want to take me to the bedroom?” she asked quietly.
Philip looked around, half expecting that she must be talking to someone
else.
“Me…you’re asking if I’d like to take you to my bedroom?”
“Don’t see anyone else here Philip,” she sighed. “So, you want to or not?”
He didn’t need further urging and taking her hand, he led her to the
bedroom which led off the small hallway. It displayed no greater a degree
of tidiness than had the lounge-room. The bed-sheets looked like they had
been slept in since Ronald Reagan came to office. Clothes both clean and
crumpled, were strewn across two chairs not including the small pile the
far side of the bed. Empty glasses sat on the small bedside table – the
general impression was that of a confirmed if not hopelessly undisciplined
bachelor. Realizing the room’s shortcomings so far as the immediate
presentation stakes were concerned, Philip hurriedly pulled the coverlet
straight, hiding the chaos beneath.
The girl sat down on the quilt, arms at her side, looking up at him. She
caught his furtive glances down her bra but if anything found them
arousing rather than demeaning. After all she knew she had sexy breasts –
no point thinking otherwise. She wasn’t however expecting his next
sentence.
“I want to spank you Samantha,” he evoked the courage to announce. “Just
like I see happening to some of the girls on that site….always wanted to
do it to a girl.”
“I didn’t say anything about getting spanked,” she replied nervously.
“I won’t hurt you,” he added hastily.... “Not real hard Samantha…just a
few light spanks on your bottom is all.”
“Just a couple then,” she giggled. “and not with my panties down
either….OK?”
“Sure, not on your bare bum,” he promised. “Just one more thing though,”
he averted his eyes momentarily as if scared of rejection.
“What now?” she asked. “You want me over your knee?”
“No,” he replied uneasily, “I actually want to spank you….er, standing up
in front of me?”
“That’s so weird,” she giggled afresh. “You want to spank a girl while she
stands up? Not even over a chair or something?”
“I know it’s strange,” he semi-apologized. “I just find the idea of
spanking a girl while she’s on her feet really hot. It’s a fantasy I’ve
always had.”
“O..kay,” she answered, getting to her feet. “This alright?” she asked,
standing now no more than a foot in front of him. “With my bottom to you
like this I presume?’ she wriggled her hips pretty much in his face.
Staring at that curvy little butt, he knew then the meaning of true
happiness.
The first smack was gentle enough. The feel of those firm cheeks beneath
his palm transported him to a localized Utopia. The second was measurably
harder but raised nothing more than a soft whimper from the girl. She
could feel the effect it was having on her already….a moistening of her
labia and a distinct tingling in her nipples. Wanting both to please and
titillate her partner even further, she bent over fractionally which had
of course the effect of making her panties cling even tighter to her
slightly elevated bottom as well as highlighting her sexy rear crevice
even more.
Philip’s third was a spank to rate with the greats. Besides crying out in
shocked discomfort, she straightened up and clutched her reddening
backside with both hands.
“That hurt” she wailed, even as he reached around her, both hands cupping
her breasts while he nuzzled her neck with unpracticed affection. Fully
off-balance, she was easily directed to fall on to the coverlet where
Philip continued to grope her needfully. The sensation of her hot young
bottom pressing into his abdomen was definitely something he could get
used to.
Semi stifled by the bedclothes, she realized soon enough that the pain of
her smarting rear-end was rapidly being replaced by the pleasure inherent
in having her breasts fondled. His hands were now inside both cups and
squeezing her nipples rather roughly. It was such fun being a girl!
Philip was having fun too – perhaps the time of his life. Even the girl’s
scent was vaguely intoxicating. He rubbed his face in her hair as he
groped her even harder. His erection was pressing up against her rear
cheeks now and it was hardly likely she hadn’t noticed. Unhooking the
clasp just below her shoulder-blades, he began to slip both bra straps
down her arms while she wriggled and teased him unmercifully.
“I didn’t say you can get me topless,” she giggled, even as he eased both
arms free, tossing her bra on to the bedside table. He rolled her over on
to her back so that she was forced to cover herself in the time-honored
crossed-arms position.
“That’s really naughty,” she gasped,
He sensed exactly how to address that situation and seizing the waistband
of her panties made as if to tug them down.
“Noo not my panties, leave them on please!” she wailed, making a grab for
them. This of course presented Philip with an unobstructed view of the
teenager’s pert breasts, smaller than he had believed them to be but
still, enticingly hot. Inclining his head, he indulged his long standing
fantasy of sucking a girl’s nipple. Samantha squealed momentarily as he
drew down on her breast, the suckling sensation causing her to become even
more highly aroused.
Unable to control himself now, Philip thrust his right hand between her
legs and began rubbing the girl’s vaginal area through her panties. So hot
did it feel, he was unaware that he had begun whimpering in pleasure
himself. Far from objecting, Samantha spread her legs wider, happy to
allow him access to the general area. Beginning now to kiss her on the
lips, though with little mastery of the craft, he took that last assertive
step and slipped his hand inside her panties.
Whatever he had been expecting this to be like, its reality was far
greater. He couldn’t believe how inviting her soft pubic hair felt, how
moist her pussy seemed, but a few inches further south. The girl yelped as
he slipped a finger deep inside, her breathing now as irregular as that of
her molestor.
Needing to see her naked became his primary focus and with the image still
of Angie sprawled so indecently on her bed, he used both hands to
literally wrench the young girl’s panties off. No longer concerned with
any false modesty and cognizant of her likely immediate future, Samantha
just lay there, hands over her head, allowing him to ogle her total
nudity.
“Are you going to fuck me Philip?” she giggled, quite deliberately
spreading her legs enough that her moist slit took center-stage in the
viewing options.
For a moment he didn’t know what the hell he wanted to do first. Finger
her again, kiss her hard, play with her breasts or a combination of all
three. Then of course there was the matter of the uncoiled serpent between
his own legs.
Samantha watched as he knelt alongside her, beginning now to unzip his
pants, his eyes fixed upon that provocative triangle of light-brown hair
that she was more than happy to leave exposed to his lustful vision. It
was only when he finally pulled from the confines of his boxers, that
which she had only previously felt up against her bottom, she let out a
genuine cry of surprise.
Philip was big…anyway you cut it. The evening most certainly had
possibilities.
Kneeling there, his swollen erection eyeing off its opposite number, he
realized he had no knowledge of how to proceed. The jigsaw puzzle itself
was simple enough – only two pieces to fit together…just the mechanics of
the thing!
“I think you need to come over here,” she smiled, opening up even more.
“Here, let me,” she added, taking a hold of his thick shaft and guiding it
in between her well lubricated opening, as he lowered himself to the task
at hand.
Unable to continue thinking rationally as his manhood acquainted itself
with its new surroundings, all he felt was a compulsion to thrust in
deeper. He became unaware of the girl’s sexual plight, needing simply to
fuck his hitherto underprivileged way to Nirvana. Virgins do have fun
indeed!
Filled to capacity and finding herself being used as a whore more or less,
Samantha tried to get her breath as wave upon wave of unimagined pleasure
took her to realms she had never visited. His methods might lack a certain
finesse, but there was no doubting his commitment. If this wasn’t in the
upshot, the fuck of the century it was a close runner-up.
Unable to prolong the outcome further, he expelled maybe fifteen years of
enforced celibacy into that sexy little receptacle. Even as he cried out
with the release, the girl responded by raising her knees and widening to
her theoretical limit. Her eyes closed in ecstasy she simply lay there
murmuring, “Keep fucking me Philip, keep fucking me……”
It was barely ten o’clock! |
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