The MILF Machine: The MILF and the Mobster
By Dr. Beaubourg
Commissioned by Jwargod
Like most of the nights in this city it was raining, and hard. Tonight
would happen to be the night that would change the lives of two down on
their luck strangers. For Shane Willis and Derek Kastanos, it all
started at a shitty diner in an even shitter part of town.
"Oh great," thought Shane, gazing out at the droplets on the window "And
me without my umbrella." A normal 20-something college dropout, Shane
had just finished his shift at the local Gas n' Gulp and was rewarded
with a pink slip. This wasn't the first time it has happened, and Shane
guessed it wouldn't be the last. He finished the fries on his plate, and
dreaded the moment the waitress would come around, requiring him to pay
and venture out in the rain. He felt like crap, but at least he wasn't
sopping wet.
Two seats over sat the lumbering 30-some year old Derek Kastanos. Unlike
Shane, who was killing time after his work, Derek was anticipating the
hour before his own shift with a quick bite to eat. He was in a bit of a
hurry, so he quickly wolfed down his meal. Soon enough, the waitress
popped out through the door behind the counter with two receipts in tow.
She laid them carefully beside their plates, as the two scrounged around
for their wallets.
Shane visited the ATM before coming and cashed out his meager paycheck,
so he had a few bills to pay for the meal. Derek had not. He fumbled
about with his wallet, failing to produce his credit card. After a
minute, he assembled all the loose cash and change he'd stored in his
wallet and pockets, but even that was a buck short. Meanwhile, Shane was
watching from his stool. "What the hell, I'll help him out," he thought,
reaching for a spare dollar.
"Here," Shane said, laying it on the side of the plate. Derek looked at
the bill, then back up to Shane. Before he could say anything, Shane was
well on his way out the door. Derek lumped the stranger's donation along
with his own money and stood up, following Shane out the diner.
"Hey pal, wait up!" said Derek as he walked through the door. It appears
he caught Shane just before he left. He was huddled beneath a balcony
taking shelter from the downpour. Derek went up to him, splashing in
puddles with each step. "Hey, I just, uh, wanted to say thanks back
there."
"Er, don't mention it. It wasn't much," said Shane, adverting his eyes
in embarrassment. The truth is he didn't get many thanks nowadays. "It's
just a dollar, you know."
"Yeah I know, but I appreciate it. Look, the least I can do you is walk
you to where you're headed. You're apt to catch a cold without an
umbrella of your own." Derek gestured to his own umbrella which looked
large enough to shield two people from any torrent of rain. Shane
fidgeted about. First a thanks, and now this? He certainly wasn't
accustomed to this kind of consideration.
"Er, I'm not so sure. My place is a few blocks out, and it's not a good
neighborhood, so you probably don't want to head out there..." mumbled
Shane.
"Bad neighborhood? Trust me, I've been there and back. Which way are you
headed?"
"That way, I guess." Shane pointed down the street in the direction of
his home.
"What a coincidence, I'm heading over there as well. C'mon pal." Derek
unfurled his umbrella and guided Shane under it, heading back to Shane's
apartment. The two of them strolled on, the bright lights of restaurants
and businesses glowed about them like a museum of neon art. Along the
way the two of them made small talk. Shane told Derek about his work
troubles, and Derek listened. He felt a little strange, a guy as scrawny
as he was walking side by side with someone as physically intimidating
as Derek was, but something about his demeanor set him at ease. Shane
thought if felt good to let it all out for once, even if he's never see
Derek again. At least that's one person that might remember him the day
after.
After 10 minutes, the two of them had reached Shane's apartment complex.
"Hey, thanks man, I really appreciate it," said Shane, his spirits
lightened.
"Don't worry about it," replied Derek. "After all, you're the one who
helped me out. I just thought I should return the favor."
"Well, if you insist. Have a good night." With that, Shane disappeared
behind the door, and Derek returned to the street. Who'd of though he'd
be working across from Shane's apartment that very night. "It sure is a
small world," he thought as he entered the building.
Derek ascended a few flights of stairs as dim fluorescent lights beamed
their soft rays down on him. At the end of the hall was an older man,
even bigger than Derek, leaning against an old doorframe. "Yo, Derek,"
he called in a gruff voice.
"Yo yourself," Derek said dismissively.
"Listen D, your job tonight is to guard this creep," he said, pointing
into the room. Past him was a waifish looking man hunched over a desk,
the smell of his soldering tools burning Derek's nostrils. "Keep an eye
on this one. He may be building something for the boss, but he's an
antsy one. Anyways, you're on point, I gotta' take a piss. Don't nod
off, ya' hear?" The other man walked down the hall, and Derek took his
place. From where he was standing, it looked like the guy he was
guarding was tinkering with some elaborate remote control. Derek
observed as the man frantically flipped through the blueprints, the back
to his soldering. Derek felt like it was going to be a long and arduous
night.
In the mean time, Shane was having a good night's sleep for once. The
prospect of finding another job lingered at the back of his head, but he
was nevertheless relaxed. For now he was lost in the aether of his
dreams, surrounded by his subconscious REM. Until he was jolted awake.
"You can't do this to me!"
Shane stood up in his bed, awakened by the sharp voice from outside his
window. His apartment was only on the second floor, so he'd become
accustomed to picking up chatter from below, but nothing as frightening
as this. He peered through his blinds to get a better look at the
cacophony outside.
From Shane's perspective it looked as if a really thin guy was trying to
wrestle out of this bigger guy's grip. The thin guy had something the
big guy wanted. A burglary perhaps? Against his better judgment, Shane
sprung to his feet. Normally he'd just ignore the events outside and
return to his slumber, but tonight he felt great. Maybe he could make a
difference in someone else's night, just like Derek had done to his.
Still clad in pajamas he slid out the door, invigorated with a sense of
pride for once in his life.
Shane slid down the stairs and busted out through the door, ready to
confront the ne'er-do-well. He turned the corner, took a deep breath,
and hollered "Hold it right there you-!" His statement was cut off by
the reality of the situation he had so precariously thrown himself into.
By the looks of it, the big guy was much bigger than he seemed from the
second floor. Also, he seemed to be pummeling the shit out of the thin
guy, as evidenced by the blood caked on the big guy's fists. The thin
guy hung limp in his grasp, the thing-a-ma-jigger he held on to earlier
resting on the ground.
"Ah, er, I think I'll just be going then..." said Shane, his fight-or-
flight reaction set to flight. With fear replacing his bravery, Shane
failed to notice the big guy motioning to something behind him. He also
didn't notice the leather sap coming straight down on his cranium.
It wasn't until Derek brought the sap down on him did he realize that
the victim of his stealthy assault was Shane, the guy from earlier.
Shane dropped to the ground, beads of red dripping from his scalp to the
damp pavement below. Lifting him up, Derek turned to his companion with
his scrawny acquaintance slung over his shoulder.
"Good job D, you dealt with him and not a single witness from the looks
of things. You know what to do next, right?" asked the companion, his
own victim still laying in a crumpled heap beside the doorway.
"No, should I?" asked Derek in a sarcastic tone. Part of him wished the
answer would be different than he has ascertained.
"Hey, don't get cute. Just take him out to an abandoned lot and plug
him. The Boss said that we don't need any more prying eyes, we're in hot
water enough as it is."
"But can't we-"
"No buts! It's either him or the both of you. You're a good guy D, I'm
trusting you to make the right decision here. You go ahead and deal with
that, our friend here needs to learn a lesson," He smirked, dragging to
the tinkerer off the pavement. He then made for the door, slamming it
behind him. Derek and Shane were left all to themselves out in the cold
alley. The reality of the situation got to Derek, who had to lean
against the wall to catch his breath. It's been a while since his last
panic attack, and he was getting awfully close to his next.
When things got tough, Derek though it helped to check his surroundings,
see if anything could help his predicament. Resting across his shoulder
was Shane, the problem at the moment. Garbage cans, old cardboard boxes,
and an old remote control on top of some papers laid on the ground
before him.
"Wait, haven't I seen that before?" thought Derek as he grabbed the
remote. He gave it a once over, and then snatched the moist the papers
beneath it. By the looks of it they were an elaborate series of
blueprints and instructions on how to use the remote. However, it was
clear to Derek that this wasn't any ordinary remote. Just then, an idea
had taken hold in Derek's mind. He pocketed the remote and it's
instructions, and walked off with Shane in tow, disappearing into the
shadows.
When Shane awoke, his head hurt. Like, really hurt. That was the first
thing he had noticed. The second thing was that he wasn't at home. It
was somebody home, as evidenced by the lumpy couch beneath him, but
definitely not his apartment. It was also very dark. He could just
barely make out the walls around him, but anything else would be a pain.
Speaking of pain...
"Ow... Where am I?" asked Shane, not expecting a response.
"That doesn't matter right now," replied a gruff, yet all too familiar
voice. Shane jumped at the disembodied voice, his eyes darting about to
find his captor. A shadow he could only assume was a man stood by the
doorway.
"What's going on?! Who are you?!" asked Shane, his voice becoming
shrill. The pain in his head flared up again, a sharp red bolt within
his skull. He tried standing up, but his limbs felt heavy. Who ever
jumped him last night really did a number on him, or so he thought.
"Listen, this is for the best," muttered the shadow in the door. "For
the both of us," Shane could hear the soft sounds of someone grabbing
papers from their pocket. Suddenly, a light shined on the figure. The
bright LED of a keyring light illuminated the figure before him,
revealing to Shane the fellow from before. Derek, wasn't it?
"H-hey! I know you!" exclaimed Shane. Maybe he could guilt Derek into
letting him go. If only he knew why he was held captive...
Derek said nothing in return, only shutting his light off. Shane could
hear him crumple up something wet, followed by the sound of him fiddling
with another object. A few clicks, a few beeps, then silence. "Trust me,
this'll work out in the end."
Suddenly, green sparks erupted from Derek's hands, shooting out towards
Shane. Instinctively Shane threw his hands before his face in the hopes
that he can protect himself against whatever sorcery Derek had cast on
him. A few seconds passed as Shane forced his eyes shut, unable to face
his own doom. His body felt warm, but he didn't feel hurt. If this were
death, than Shane would have thought it was quite anti-climactic. Sure
enough, he opened his eyes, trading the pitch black of his eyelids for
the dark of the room.
"Wha- what was that?" asked Shane. A rhetorical statement, though he
wouldn't mind an answer. Instead, he was greeted with Derek's sharp
light nearly blinding him. He shielded his eyes against the harsh ray.
"Hmm. Good. Looks like this thing is working," said Derek, giving Shane
a once over. The light dimmed, and Shane heard a sound of breaking
plastic, followed by him discarding whatever he used beside him. This
was followed by the sound of keys jingling, and a door unlocking.
"Look, I'll be back in the morning to check on you. There's a bedroom in
the back with clothes for you. Don't try to break out; I've fool-proofed
this place. Just let it happen, and we'll work something out," Derek
then opened the door behind him as fluorescence lights shined through
the crack in the door.
"Wait! Don't leave me!" called out Shane, his voice cracking ever so
slightly. He held out a hand, hopelessly grabbing for the door. As he
did, Shane could feel a pulling sensation in his fingers. He held them
up to the light behind the door and stared. Before his eyes, the shadow
of his hand began to change. His fingers shrank, becoming petite as his
nails lengthened. It was then that Derek poked his head through the
doorway for one last comment.
"Just act you're age, and we'll be fine." And with that Derek left,
dimming the room once more. Shane's eyes tried to adjust to the darkness
as he felt a chill spread throughout his body.
At first Shane felt the shrinking sensation from his hand throughout his
whole body. His pajamas, which once fit snugly about his body, now felt
a bit big for him. The sleeves hung loosely from his now manicured
hands, sliding down soft, hairless arms. His legs also felt smooth
within his pants as he couldn't resist rubbing them together through the
thin fabric. As they rubbed, he found more resistance against his legs,
as if they were bulking up. It was slight at first, focusing in on his
calves, but the bulking rose to his thighs which increased dramatically.
Shane was a thin person, but within a few seconds his thighs mashed
together, straining his pajamas as the seams. Shane's hips began to
widen as well, straining the waistband of his pajama pants. It was a bit
uncomfortable, the change leaving him sitting on his coccyx. However,
this was soon alleviated. Shane felt the rear of his pajama pants
becoming tighter as his seat taking up more space then before. He could
feel the back seam at its limit as Shane rose in in the air as if
sitting on a fleshy inflating cushion.
By this point Shane suspected that he had been drugged with something,
and that this was becoming a very bad trip. So bad that he was actually
starting to feel numb. His penis, which had become a throbbing erection
through all of this stimulation, felt anesthetized beneath his pants.
More and more it seemed to slip away from his body, as if it never
existed in the first place. The sensation of arousal was still there,
centered between his legs. It was different than before, a warm feeling
in his groin. Shane dismissed this as part of the trip as his torso
followed in the bizarre changes.
Beneath Shane's pajama top he could feel his waist diminishing even more
than before. He brought a dainty hand to it, feeling how much smaller it
was. Beneath his touch it felt toned as well, but Shane never found the
time to work out in his schedule. Shane's fit tummy seemingly
contradicted his chest, which felt flabbier than before. Shane tried to
look down at his fit stomach, but found that a shadow blocked his
vision. As he gazed down, the shadow grew, blocking most of his vision.
A tingling sensation emitted from his chest, joining the one in his
groin. Suddenly, his pajamas seemed all too tight. It was only a
momentary discomfort, as he felt the sensation of buttons popping on his
pajama top, airing out his sweaty skin to the cool air. Finally Shane
was able to breathe. He took a big breath, another button popped forth
from the strained shirt. How weird.
Shane stood there, the pleasure from his body distracting him from his
predicament. Suddenly, he felt an itching sensation in his face. He
decided to ignore it, but it grew, and Shane had no choice but to
scratch. He nearly forgot about his nails as he scratched, but he was
glad that he didn't. His face felt somewhat swollen, particularly in his
lips and cheekbones. The former stuck out from his face, clearly plumped
out. Maybe he was having an allergic reaction, although Shane wasn't
know for them. He pressed down on them, surprised at their springiness.
"Weird" muttered Shane. It was difficult to enunciate with his swollen
lips, the extra mass pressing together with each syllable. It also
didn't help that his voice was still cracking. It's like puberty all
over again. He suddenly felt a tickling sensation on the back of his
neck, and swiped at it with his hand. At first he had batted it away,
but it returned to his neck, nearly reaching his shoulders. It bothered
Shane, but he didn't care. He just sat there in his seat, feeling like a
stranger in his own body. A minute passed, and the changes ceased. Shane
had partaken in recreational drugs before, mostly to keep his mind off
of his miserable life, but found than no high was quite as short-lived
or intense as this one was. Now that it was over, Shane had to come to
the bottom of his situation. First off, he had to turn on the lights.
After all, he couldn't stumble around in the dark all night.
After a few tries, Shane mustered up the strength to stand up, still
feeling the effects of whatever he was given. He stumbled about in the
darkness, wobbling about in an odd way. He walked around, trying to find
a light switch. It took him a minute or two, but Shane finally found
one. Finger on the switch, he counted to five, not sure of what he'll
see when he flips on the lights. He hoped to god that this wasn't some
sort of slaughterhouse and Derek was a secret serial killer.
At long last, the lights flickered to life, revealing a normal, if not
drab apartment. This wasn't like his own; this apartment was made for a
small family to live in, as opposed to his own one-person abode. From
the looks of it, there was a dinette, living room (where he assumed he
was sitting before), and a hall, most likely leading to a few bedrooms,
maybe even a bathroom. At the end of the hallways was an open door,
where a woman stared at him.
"H-hey! Where is- Ah!" said Shane surprised at the tone of his voice. It
was light, almost sing-songy, and certainly not masculine. Shane brought
his hand to his throat, and the woman did the same. It looked as if she
was mimicking Shane, as he felt embarrassment roll over him. Shane
adverted his eyes, looking down at the ground, but two large objects
greeted him, poking out through his pajamas. A pair of fleshy lumps
protruded out from beneath his shirt. Shane grabbed a hold of them as a
foreign sensation took over, a pleasure he hadn't ever felt in his life.
"Ah!" he gasped in a feminine tone. He looked back up at the woman, and
to his surprise she the same, grabbing her breasts in a crude, lecherous
fashion. The pieces began to fall into place as Shane approached the
woman, still mimicking his movements. Her wide hips swung back and forth
as Shane stepped closer and closer, her tits bouncing as Shane's did.
Finally he was standing right in front of her. She was beautiful, a
voluptuous older woman, with blonde bobbed hair that rested atop her
shoulders. Her outfit barely contained her curves, as evidenced by the
seams on her hips and busted out buttons containing her breasts. Shane
bent back, snapping off the last two buttons that held his pajama top
on, casting it aside. The woman did the same, bearing her heaving
breasts to Shane. It was official, as Shane could no longer deny it.
Shane stared into his own reflection, and that he was now a she,
transformed into a milf.
The realization shook Shane to her core as she stumbled about, leaning
against a wall for support. The body that was hers for many a year was
gone, perhaps even for good. His body didn't do Shane a lot of good, but
damn it, it was hers. Emphasis on hers. The cold apartment air seemed to
caress her soft flesh, raising goosebumps all about her body. She could
feel her nipples harden and become erect as if to remind Shane of the
alien body she now inhabited. She felt exposed and embarrassed without
her shirt, which laid behind her. Shane bent over to pick it up, her
slim arm outstretched to the garment. Midway through her descent, Shane
heard a rip from behind her, followed by the bitter chill of the open
air grazing her cheeks. She bolted to attention, checking the rear of
her tightened pants in the mirror. Sure enough, the seam had split right
down the middle, placing Shane's bulbous ass out on display
The blood rushed to her cheeks as Shane blushed, embarrassed by her own
voyeuristic stare from beyond the mirror. She attempted to cover up her
rear, but was unable to completely hide her fat rear behind her dainty
hands. Defeated, Shane gave up, and decided to explore the rest of the
apartment before she had another breakdown. If Shane remembered
correctly, Derek said something about a bedroom in the back. Sure
enough, an open door led to a dim bedroom. There were the usual
accommodations. Bed, bathroom, vanity mirror. By the looks of it, this
belonged to someone's mother. The photos that littered the dressers
confirmed this, although whoever lived here was long gone, as evidenced
by the layer of dust coating the drawers.
After a few minutes of riffling through the clothes, Shane finally
procured a few appropriate articles of clothing. Namely, a pair of bra
and panties. For a minute she debated with herself whether she wanted to
wear them or not, and found that they were indeed designed for women's
comfort, and something was better than nothing. As she slipped them on,
Shane found that the panties fit well, although her rear was much too
full for them, with the back finding no place to go but flossed between
her sizable ass cheeks. The bra proved more difficult, as Shane had no
previous experience with them, taking them on or off. A few minutes
passed, yet she managed to place them properly. However, the bra was
made for a woman much less ample-chested than she. However, she now felt
some semblance of modesty, even if the garments were a bit restrictive.
Still, Shane thought that a shirt would be more appropriate, so she
threw on the largest shirt she could find.
Up next on the agenda was finding out just where in the world she was.
Upon further examination of the apartment, the windows we either blocked
off, or weren't even windows at all, leading to a cement wall. Derek was
right, this place was fool-proofed. No one sees in, no one sees out. Of
course the door was locked, Shane didn't even need to try it to find
that out (but she did anyways). One point of interest was a trashcan
beside the door, empty save for two items. One, a slightly wet pile of
what appeared to be notes or blueprints. The other, a smashed remote
control. Shane felt like she had seen something like that before, but
just couldn't put her finger on it.
"Well, I might as well check it out," thought Shane. Suddenly, she had
become bothered. Even her own inner monologue began to sound like her
new voice. Shane thought that she must have been getting used to it.
Frightening. Shane plucked the notes out of the trash and scanned it for
any clues. Luckily for her, it was chock full of information.
"MILF Machine Prototype:
After you gave me the scrapped parts, I managed to put a prototype
together. While I'm not sure that this'll make any person a whore like
it was proposed, it's at least a starting point. Altering someone's will
is something beyond my skill, but you're in luck. I know a guy who can,
although he'll need some "convincing". He's a bit of a nut, but If you
can get him to comply, then you might be able to work on making more of
these. Until then, it'll have to do."
The note ended with a bunch of diagrams and addresses and other things
Shane couldn't wrap her mind around. What she did catch was what this
thing was used for. It seemed to Shane that Derek had used this to make
her his whore, trying to get some money on the side. Well, no dice. It
seemed to Shane that she was plenty capable of resisting him. Maybe not
physically, after all Derek seemed like he was carved out of rock. No
way she could fight him. But maybe Shane could play mind games. After
all, what man wouldn't fall for a busty blond babe like herself? She
certainly hoped that Derek would.
Shane stood up and gazed into the mirror across the hall. Sure enough,
the stranger Shane had now become looked back. Imitating one of her pin-
up posters from some playboy back when he was young, Shane pulled down
on her baggy shirt, displaying her deep cleavage. "This'll be a cinch,"
thought Shane, unable to take her own eyes off of her large tits. Talk
about turning lemons into lemonade. Shane was going to use her new
feminine wiles against her captor, and when he least expects it, she'll
make her escape and try and find another one of these "MILF Machines"
with the hope that the next one has an undo button.
Shane yawned, throwing her arms up in a stretch that pushed her breasts
against her shirt, the fabric pressed snugly against her large breasts.
"I guess I should sleep for now," she thought aloud. She snatched the
sheets from the bedroom and rested on the lumpy couch. It felt weird to
her to sleep in someone else's bed, so this would have to do. She
thought once more about her predicament before she drifted off into a
dreamless sleep.
The sound of the front door slamming jolted Shane from her rest. She
first thought that all that happened was some sort of strange fever-
induced dream. Shane threw back the sheets to check if she was still a
man. Two plump tits proved that she was not.
"Hey, over here," a familiar gruff voice said from the door. Shane
whipped her head in that direction as a bright flash filled her vision
followed by the familiar sound of a polaroid picture's printer. The
glare ceased as she rubbed the spots from her eyes.
"Hey, what on earth was that for?!" she said, blinking the spots away.
"Oh nothing. Just providing you with tools to live a productive life.
Unless you want bum around on a couch for the rest of you, er, adult
life," said Derek, giving Shane a look over as he spoke. Shane could do
nothing but try to avoid staring daggers at him. If she wanted her plan
to work, she was going to have to act inconspicuous.
Meanwhile, as Derek shook the picture into visibility, he pulled a small
black box from his coat. He placed it on a counter, and fed it the
photo. A series of loud clicks and whirrs from the device and finally it
spat out a card, ejecting the excess waste behind it. He then walked up
to Shane and handed her the still warm card.
"Here, take this. You're going to need this if you're going to go out
and work," he said, slipping the black box back into his jacket.
"W-work?! You're putting me to work?!" Shane yelled, dropping the card
before she could even give it a once-over. Shane knew that Derek was
going to do something like this, but she couldn't possibly expect to be
out on the streets turning tricks as soon as the next day. Shane felt
desperate enough to bolt for the door, but Derek was far too imposing
for her to consider it. More than ever before, Shane truly felt
powerless.
"Don't worry about it. I've got a friend who owes me a favor. He runs a
small casino downtown and he'll set you up with a job. Nothing fancy,
just serving drinks," Derek said.
Whew. Shane wouldn't have considered herself a godly person, but she'd
thank just about whoever intervened there. The longer she stayed without
a man taking advantage of her, the better. As the dread in her gut
subsided, she felt a distinct warmth between her bosom. She dove her
fingers down her shirt, procuring the card from earlier.
By the looks of it, Derek managed to print off a forged I.D. using the
photo from earlier. Shane was embarrassed by the face she made in the
photo. Honestly she would have preferred some time to get ready. Male or
female, she could have like to look nice for her only form of
identification.
"I decided on a name that sounded close to yours. You'd better get used
to it, because I'm all outta' ink with this thing," he said, patting the
black box through his jacket. The name "Sandra Webb" captioned the
photo, along with a bunch of other bogus info. Sex: FEMALE (that was a
given). Hair: BLONDE Eyes: GREEN. Height: 5'8". DOB: 4-17-1966.
"April 17th, 1966?! That would make me-"
"Forty nine. That's how old I'd guess you are. Unless you've got a
better idea, that's what you're going to stick with. Anyways, get ready.
You've got an interview in an hour," Remarked Derek, sitting down in a
chair opposite Shane. Or Sandra, as it now were. She thought that using
that name for a bit would be opportune, sticking with Shane might make
Derek think that she was resisting. Right now, keeping him unsuspecting
was priority number one.
With that, Sandra reluctantly got off of the couch. She regretted not
finding pajama pants of some sort as she had to trek back to the
bathroom, her full ass exposed for Derek to see. She darted into the
bedroom to avoid his gaze.
Sandra spent the better part of the next hour getting cleaned up. A
quick hot shower was first, washing her drowsiness away down the drain.
The next part proved more difficult. Sandra spent a while drying and
preparing her hair, unsure of how she should present it. In the end she
decided on wearing it down. Sometimes the simplest route was the best.
By then she had noticed a pink bag sitting by the vanity mirror. Inside
were the usual adult woman's accessories, including a small makeup set.
Sandra (back when she was just plain Shane) had spent enough time around
girls in high school to know the basics of putting on makeup. A bit of
eye shadow, some mascara here, already she was looking a lot better than
her photo. She used up a lot more lipstick than the thought, with her
lips a lot thicker than the norm.
Sandra shut the purse, leaving herself to the clothes that barely fit
her. After a few minutes of sorting through all sorts of outfits, Sandra
decided on something simple. A blue satiny blouse (to which her bust
barely fit in without bursting a few buttons), with a high waisted
pencil skirt (this one a bit too tight around the hips). There didn't
seem to be any regular shoes in the closet, so Sandra settled on a pair
of black three-inch pumps. Sandra admired herself in the mirror. She
didn't look too shabby for someone who just rummaged around in a
stranger's closet. Tempted, she decided to play with the outfit a bit to
see how she looked. Sandra popped out a few more buttons, spilling out
her cleavage.
"Let's try to see if you can resist this, buster!" Sandra muttered to
herself. She pushed her breasts together to see how it looked in the
blouse. Then spread apart (the former being much easier in her more-
than-snug bra). With all this stimulation she could feel her nipples
becoming erect. Sandra quickly threw off her bra to see how her breasts
looked in the blouse. Just as she suspected, her nipples poked through
the sheer cloth, giving her the look of an erotic librarian, sans the
horned rimmed glasses. Sandra rubbed her palms over her nipples, the
moaning ever so slightly. A warmth seems to accumulate between her legs
as she rolled her pert nipples between her fingers. This was nothing
like anything Sandra has experienced as a man. Her mind blanked, only
focusing on her heightening arousal.
A sharp rapping at the door brought Sandra back down to earth, nearly
making her yelp.
"Hurry up in there. You do not want to be late for your interview, do
you?" said Derek from behind the door. How long had he been there? Had
he heard her? These things flashed through Sandra's mind as her face
turned beet red.
"Ah- I'll be out in just a minute!" Sandra responded. She suddenly
remembered her own adolescence, pleasuring himself before his mother
came in to clean his room. "Some things never change..." she muttered to
herself as she frantically buttoned her blouse up. With that, she was
out the door, face to face with Derek.
"Let's go," she snapped at him stomping her way out the door as Derek
followed. Sandra quickly learned that she wasn't accustomed to high
heels as she teetered and wobbled her way through the apartment complex.
Sandra managed to falter her way down the stairs (sending her bra-less
chest into a bouncing frenzy) and out the door. Sandra stood next to the
car, nearly leaning on it to keep her balance.
"After you," Derek said, opening the passenger door for her. Sandra
reluctantly entered the dusty old automobile, crossing the seatbelt over
her sizable breasts. Derek entered, and with the roar of the engine,
they were off.
It was an awkward ride to say the lease. No music, no conversation, no
eye contact. Derek kept his eyes on the road, occasionally glancing at
cars behind him with suspicion. Sandra lazily gazed out the window,
imaging what kinds of lives the pedestrians they past had. The silence
was broken only once during the ride.
"...Are you sure you want to go in like that?" he asked, his eyes firmly
locked before him.
"Like what?" Sandra retorted with a bit of unchecked hostility in her
voice. Derek scanned her for a moment, his eyes slightly lingering on
her bosom before returning to the road.
"...Never mind," he mumbled, shaking his head. Sandra felt a bit self-
conscious. What could be wrong with her? Surely she hadn't forgotten
something? Sandra returned to looking out the window when her eye caught
the side view mirror. She squinted past the sharp reflected glare and
noticed that her nipples were still fully erect, sticking out through
her shirt. Sandra hid the twin peaks by covering her arms, sinking back
into her seat.
Soon enough they had reached their destination. Derek drove up an alley,
parking before a back door to some shady establishment.
"Alright, this is your stop," said Derek. "You go in there, tell him
that you want a job and that Derek Kastanos sent you. He'll get you
sorted. Call me at this number when you're done, capische?" Derek
offered a scrap of paper to her.
"Capische," Sandra said, snatching the paper from his grip. She left his
car, \ sashaying her way through the door, stowing the scrap paper
within her deep cleavage.
Just as Sandra had expected, the place's interior was as crummy as it's
exterior. It looked like a normal office, albeit with a significantly
smokier atmosphere. To her right sat a portly man behind a desk, sorting
through papers while sucking down a cigarette. He snuffs it out in an
ashtray that's already at capacity, it's embers resting on other
extinguished butts.
"Alright, whaddya' want lady? I'm a very busy man, so make it snappy,"
he grumbled, smoke billowing from his maw.
"Um, Derek Kastanos sent me. he said you could provide me a with a
job...?" Sandra said, sheepishly. She sat in a stool opposite the man,
surprised when her rear made contact with the cool metal seat sooner
than she was used to. The stool, much like everything else provided for
her, was too small for her globular rear as it managed to hang off the
back unsupported.
"Derek Kastanos?!" he bellowed. His sudden change in tone making Sandra
leap in her chair. "Do you know what that son of bitch did to me?"
"Er- ah- no...?" Sandra didn't like where this was going.
"He made me filthy stinkin' rich, that's what! Hah hah hah!" he
chortled, leaning back into his chair. "I kid, I kid. The name's Kolby.
Travis Kolby. Nice ta' meetcha'," he extended a meaty palm to her, a
brand new cigarette hanging between his fingers.
"Sandra Wil- Webb. Likewise." Sandra took his hand, giving it a feminine
shake.
"Well then Mrs, er, Ms. Webb," he said, peeking at her ring-less
fingers. "I believe I've got an opening for you. I'm gonna' put you to
work as a cocktail waitress. The hours are decent, but the pay ain't
that good. But you do get tips, so make it your prerogative to work hard
for 'em. All you gotta' do is sling cheap cocktails and look pretty.
That shouldn't be a problem for a woman as," he stopped to clear his
throat "-enhanced as you are."
Once again with the leering. This Kolby character's eyes were so far
into her tits, Sandra could practically feel his eyelashes in her
cleavage. This was starting to get old, but she'd have to get used to it
if she wanted everything to work out.
"When can I start?" asked Sandra, trying to sound cheery.
"Well, I'd have you start now, but you'd already be an hour late into
your shift. How's about we train you today, let you work the rest of
today's shift and call it good. Let me just call in one of your co-
workers, she'll show you the ropes," Kolby pressed an intercom button
with his meaty finger. "Alyssa, I need you to come to my office."
"If you don't mind me asking sir-"
"Kolby's just fine."
"Kolby, what was your relationship with Derek?"
Kolby wistfully leaned back in his chair, taking a drag from his
cigarette. "Derek and I go waaaaaaaay back. Like, 2006 back," Kolby
reminisced. This struck Sandra as silly but she stayed silent. "Back
when I started this place up, the mob was looking to rent out my back
rooms for some sneaky shit. Money laundering, drug peddling, I got all
the offers and I turned each and every one of 'em down. I wanted to run
a clean business see? Well, as clean as cheatin' drunk suckers out of
their money is, ya' know. Anyways, without their help I was gonna' go
belly up in half a year. That's when I met Derek. They called him the
left-hook wunderkid back then, and boy was he! I offered to host his
matches here at the casino, and we'd both reap the benefits. Derek would
get the attention he deserved, and I got the dough to keep this place in
the black. Everyone's a winner."
"So, does Derek still box?"
"Not that I know. Around 2012 he got caught up with the mob real bad.
They wanted him to throw a match or two. The kid's too stubborn for his
own good. Long story made short, they ruined him, cut down yet another
promising career. When they were done with him, he had nowhere else to
go. Last I checked he was doing goon work for them. I'd offered to help
him get out, but the kid's more stubborn then my ex. So there. If
helping you is helping him, then I'd be glad to be of service."
Kolby's story was punctuated by the jiggling of the doorknob, followed
by a few muttered expletives. One push, two pushes, and finally the door
opened with a clamor. In walked a woman who looked to be in her mid-
twenties. She wore a blue bunnygirl outfit, minus all the articles that
would make it "rabbitesque".
"God damn, I've told you before you need to replace the hinges on this
fuckin' door!" the woman said, flipping back her wavy red hair.
"Yes you have. Alyssa, you're going to show your new co-worker Sandra
her duties as a cocktail waitress, you got that?"
"Sure, whatever," Alyssa groaned. She turned to Sandra and brightened up
a bit. "C'mon Sandra, right this way. We'll find you a uniform that fits
you."
The two passed through the door and into a hallway with a locker room at
the end.
"You go ahead and get started, I'll grab a couple of leotards for you,
and we'll see which one fits the best," Alyssa said, shooing Sandra into
the room. Once in, Sandra occupied the furthest locker and began to
undress. Once out of the blouse she found it much easier to breathe.
Sandra practically had to peel herself out of the pencil skirt. Now she
was nearly bare, in all but her panties. She took one more good look at
herself in the mirror.
"This is going to be tough," she thought aloud, cupping a breast in her
hand, "But you can do this. Don't let them get to you."
"Alright, I've got a couple here, now let's see what fits!" Alyssa said,
waltzing in the room. Sandra couldn't help but let out a feminine gasp,
trying to cover herself with her arms (unfortunately, there was too much
to cover just by her arms alone).
"Oh come on, what's wrong with you?" scolded Alyssa.
"I thought you were going to just, I don't know, leave them over there
or something! You could have seen me naked!" she said, continually
shifting her arms in fear of revealing herself.
"Are you serious? This is a locker room! I've seen plenty of naked girls
in here. Lighten up a little. Now, let's see which of these fit the
best..."
Alyssa walked over to Sandra, leotards in tow. Sandra eventually gave,
up, dropping her arms to her sides. The two of them measured her bust,
holding up the garments to see how they looked.
"You know, for a woman your age, you're in great shape. No offense, of
course," she said, measuring Sandra's bust.
"None taken," It was nice to be complimented on her looks that didn't
focus on how perky her boobs were or how fat her ass was. "Alyssa, why
are you working here? I'm sure you're a nice young woman, why would you
pick a place like this?"
Alyssa stood there for a moment, scratching her chin. "Me? Well, I still
have to pay off my student loans. I figured I'd do it with something I
was good at. Men aren't that smart, they're all loins and no brains. If
you act all nice, put a little swing in your step and a smile on your
face and you'll go far. Here, I think this one'll fit you." Alyssa
handed Sandra a bright red leotard, along with a pair of heels and some
stockings.
"I'll let you handle the rest of it. I'll meet you out by the busboy
station" said Alyssa, walking off. She disappeared behind the door, the
click of her heels becoming softer and softer. Sandra now had the
privacy to change alone. She hiked the stockings up her legs, smoothing
them about her thick thighs. Next came the leotard, to which she stepped
into with ease. She zipped it up her back, pulling the leotard's rear as
to not floss between her supple ass cheeks. Sandra adjusted her breasts
within the bodice to give herself truly impressive cleavage. Finally,
she slipped on the heels, adding about 5 inches on her height. The heels
forced her to swing her hips as she walked, but Sandra didn't mind. In
fact, the more seductive she could be, the sounder her plan was. Sandra
moseyed out the locker room, ready to start her first day at work.
It was later that day, and Derek was out and about. He was visiting
various friends and tying up loose ends. Suddenly, a soft buzzing
sounded from within pocket. He extracted a cheap pre-paid cellphone. It
was good for keeping people off your trail and making the occasional
call, but not much else. He flipped the phone open and pressed his ear
to the receiver.
"What is it?" he said.
"I'm finished here," a breathy voice said from other line. "You mind
picking me up? My back is killing me..."
"Yeah, hold on. I'll be there in five." Derek shut the cellphone and
made off for his car, glancing behind him in case of snoops.
As he drove up behind Kolby's casino, a very tired Sandra slumped out, a
cloud of smoke lazily trailing out the door. Sandra opened the door and
got in, giving a breath of relief as she sat down on the plush seats.
"How was it?" asked Derek, checking his car's blind spots. Helen
unbuttoned the first few clasps on her blouse, fanning herself with a
manila envelope.
"It's hot, demeaning, and the outfit rides up my ass. So yeah, I guess
you could say it was alright," Sandra said, wiping the sweat from her
heaving bosom. Derek didn't reply to this. The car ride went on for a
while, the two minding their own business. After a while, he two finally
reached the apartment. Derek unlocked the door and escorted Sandra in,
who promptly plopped down on the couch. Her legs were splayed out as her
skirt crawled up her hips, but Sandra promptly fixed her posture.
"What's that?" asked Derek, pointing to the envelope.
"Oh, this?" she replied, opening it up. "These're today's tips. I didn't
get a chance to count them out, so here goes," Sandra dumped its
contents out, leaving a meager amount of money on the table. Derek
walked over to the table and sorted through the cash, furrowing his
brow.
"This isn't a lot. Did you even try out there?" he asked. His words were
harsh, but his tone was honest.
"Well gee, thanks. It's not like I wanted to do this or anything."
Sandra pouted, crossing her arms beneath her sizable bosom.
"Look, we're going to be here for a while. I've just got barely enough
money to keep us in this place, so this is your income. I figured you
didn't want to wear clothes two sizes smaller, so I figured you could
work to make yourself comfortable, but you're not going to afford much
with tips like these. C'mere," Derek extended his large hand, lifting
Sandra up by her's.
"Alright Sandra. You show me what you've learned." Derek flopped down on
the couch, propping his feet up on the coffee table. "Serve me a drink."
"Alright..." said Sandra. In her right hand she pantomimed holding a drink
tray. Her left hand perched on her hip, doing her best to strike a
sultry pose. "How's about a drink, handsome?" Sandra couldn't help but
sound sarcastic at this time. Derek scanned her from head to toe. She
felt a bit embarrassed, but stood as still as she could. A moment
passed, and Derek stood up.
"Alright, here's your problem. You're standing too stiff. Here, arch
your back like this." Derek circled around Sandra and placed his palm on
the small of her back.
"Eep!" she yelped. "What's the big idea?!"
"Trust me. I've seen a lot more cocktail waitress than you have. Here,
raise your hips a bit." Derek placed a hand on her right hip, sticking
her rear out. Like before, her cheeks became flushed with red. However,
she felt another warmth overtake her as well. The feeling of Derek's
hand on her hip brought a strange, yet familiar warmth between her legs.
Derek's voice started to fade away as she focused on the hand on her
hip, imagining it moving about. Prodding, gliding, rubbing about her
body. Travelling to her ass, down to her thighs, and then-
Sandra was brought out from her daydream as her legs locked up, sending
her crashing down to the ground.
"Hey! You alright?!" asked Derek, the urgency in his voice was
startling.
"I-I'm fine..." Sandra mumbled, struggling to stand up. Her legs wobbled
as she stood on the still-unfamiliar heels. Her legs buckled once more,
tilting her back onto the couch. Derek stood over her and sighed.
"You're better off just staying there for a while, alright? Take those
things off, I can't imagine you're ready to walk around in them all
day," he explained, motioning to the heels dangling off Sandra's feet.
"Go ahead and get some rest for tonight. I'll pick you up tomorrow for
work. Capiche?"
"Capiche..." she replied, craning her neck up at Derek, his large form
blocking the light overhead. To Sandra he resembled a large monolith,
bathing her in shade. Derek retreated back to the door, undoing the
locks.
"I'll see you then," he said, disappearing behind the apartment's only
exit.
"Buh-bye..." Sandra lazily murmured. She laid there on the couch a few
minutes, recounting the day's events. In a way, Sandra was thankful to
Derek for getting her that job. Had he not, Sandra would have never met
with Alyssa, and therein lied her ticked out of this place. She gazed
over to her tips envelope, pulling a napkin out of it. Scrawled on it
was a series of numbers. She thought back to her break, standing out
back behind the casino.
"Jeez, I'm sorry to hear about what you're going through," Alyssa said,
taking a drag from her cigarette. "I've been through a few shit
relationships, but you've really got it bad," Needless to say, Sandra
left out the whole "turned into a milf" part of her story.
"I know. I've been thinking of calling the cops. Is there a pay phone
around here?" Sandra asked. The cold air sent a shiver down her spine.
Next time she'll remember to take a jacket when she goes on break.
"I doubt they'd be much use to you now. By the looks of it, he's covered
each angle. You might just have to stay put, save your tips for later,
you know?" She tapped a cigarette from its box, offering it to Sandra.
"Want a smoke?"
"Sure," She said. Back when she was Shane he had taken up smoking. He
quit a year or two ago, but she sure could use one now. Sandra plucked
the cigarette and placed it between her plump lips. Alyssa procured a
lighter from beneath her cleavage, giving it a few flicks before it lit.
Her cigarette lit, Sandra took her first drag in a while, savoring smell
of burnt tobacco beneath her nostrils. She let out a puff of smoke,
glancing at the cigarette between her manicured fingers, the red ring of
lipstick reminding her of who she was now. "Thanks," She said, tapping
the ashes out.
"I'll tell you what. Once you've got enough dough to get back on your
feet, I'll help you get out of this hellhole. Anytime, any day, you give
me a ring, given you find a phone, and I'll come running over with a
ride to get you out of here. How does that sound?" Alyssa proposed,
blowing a lock red hair from her eyes.
"Really? You'd do this for me?! You're a life saver!" Sandra said,
clasping her hands around Alyssa's.
"Hey, don't mention it. Plenty of us have been stuck in one way or
another, I'm just being considerate. Besides, you're too cute to be
locked up. C'mon, break's almost up. Let's head back inside."
The memory faded from Sandra's mind as she returned to reality. She
slipped the napkin back in the envelope, clasping it for safe keeping.
She carefully lifted herself off the couch, and slowly made for the
bedroom. It'd been a long day, and if she planned on making some money,
Sandra needed her rest. She unbuttoned her blouse, zipped down her
skirt, and plopped down on the neatly made bed. A cloud of dust lifted
off the sheets, floating in the room's still air. By the looks of it,
no-one had slept in the bed for a while. Clad in just her panties, she
wiggled her way under the comforter, ready to sleep. However, Sandra
still felt a lingering warmth within her. She thought about her episode
earlier, how Derek's hands felt on her hips and back. The memory brought
the moistness flooding back into her, collecting between her legs. As
she daydreamed about it, her hand traveled down her body, almost
instinctively. She brought a few fingers between her legs, and pressed
on her unfamiliar sex. A small jolt of pleasure ran through her, making
her gasp. The pleasure was intense, nothing like she'd felt as a man.
She wanted more.
Sandra started to rub the moist gap between her legs, her fingers
circling in unfamiliar territory. She began to moan involuntarily,
biting down on her full lip to dampen them. Each time she pressed her
fingers into the fabric of her panties, she couldn't help but buck her
hips. Sandra felt the intense urge to heighten her pleasure, as if it
was all she could think about. She slid her hand under her panties and
down to her snatch, exploring this unfamiliar genital. Her other hand
cupped her breasts, kneading it as her nipples stiffened. She rolled
them between her fingers, the pleasure becoming sharper still. Finally
it reached a point where Sandra could no longer control her moans as her
breathy, mature voice rang through the apartment, a signal of the
ecstasy she was experiencing. Finally, she reached a climax, giving out
a yelp. As the pleasure succeeded, so did her energy. She curled up
beneath the blanket, and drifted away into a dreamless sleep.
"I can take your glass, if you'd like," asked Sandra, clad in her
cocktail waitress outfit. It had been a couple weeks since her first day
on the job, and she was proving to be quite the hard worker. She stood
over a crowded blackjack table, a dish with empty martini glasses in
hand.
"Sure thing, sweet-cheeks. Make sure to send some more over this way,"
the man replied, giving the glass one last swill before handing it off.
"Thanks..." Sandra said, attempting to raise the enthusiasm to respond
with her usual saccharine routine. As she walked off, she felt the
familiar sting of a palm striking her hefty rear. By this point she was
used to this kind of behavior, and walked off as the sounds of the men's
laughter was quickly drowned out by the din of slot games, roulette
wheels spinning, and swindlers snatching fools' hard-earned coin. This
was the world that Sandra had grown accustomed to. Back when she was
Shane, he had known of misogyny, but never really thought of it. These
past few weeks taught Sandra everything she needed to know about male
chauvinism. Funny how being turned into a milf changes your perception
of things.
Sandra glided over the soft casino carpet having mastered walking in
heels over the past few weeks. She dashed between groups gathered around
craps tables and pitiable men sulking back to the ATMs, passing through
a door marked "EMPLOYEES ONLY". Inside was the bartender, busboy, and
Alyssa. She was stacking fresh martinis on her tray, ready to pass out
to patrons.
"Hey Alyssa, send some of those out to blackjack table 3, and spit in
one of them for me, huh?" Sandra said, unloading the glasses.
"You got it, Sandy. You about done with your shift?" Alyssa asked.
"Yeah, just about," replied Sandra, her eyes shifting about. "Did you
pick up that stuff for me yet?"
"Of course," From within her cleavage, Alyssa procured a small plastic
bag concealing an even smaller capsule. She quickly handed them off to
Sandra, who stashed it away.
"You're a real life saver, you know?" Sandra said.
"Don't I know it." With that, Alyssa gave her a pat on the shoulder as
she strolled out the door, ready to serve her drinks. Sandra, however
has spent too long in her outfit and was ready to change out of her
uniform. She walked back to the dressing room, stopping by an old
payphone. Sandra fed it her change, and dialed Derek's cell. The sharp
dial tone of Derek's phone buzzed in Sandra's ear before his gruff voice
was heard beneath the receiver.
"Hello?"
"It's Sandra, my shift's over. Mind picking me up?"
"Yeah. Give me a few minutes." With that, Sandra hung up and made her
way to the changing room.
Derek pulled into the alley, only to be met with Sandra leaning on a
wall. By the looks of it she had dressed appropriately for the weather,
clad in a sweater and a pair of jeans (displaying only a bit of midriff,
but it's difficult when you're proportioned like Sandra was). He could
hear the click of her heels on the bare pavement as she approached the
car. Sandra opened the door and plopped down in shotgun.
"Hey, Sandra. Do you mind if we talk a bit tonight?" asked Derek, his
eyes locked forward as usual.
"What a coincidence! I was actually thinking of inviting you over for
dinner tonight anyways," Here inlaid Sandra's master plan. Part one was
to invite him over, prepare a nice dinner. Hopefully, he'll be off guard
by then. Part two: Offer him a glass of wine with a bit of Alyssa's
"stuff" in it. All things considered, he should be out cold after a few
sips. Part Three: Make off with Derek's phone, call Alyssa, and get the
hell out of dodge. It wasn't perfect, but Sandra was confident in this
plan. She had to be; this could be her only shot at escape. "Mind if we
stop by the store? I need to grab a few things for tonight," Derek
nodded in response, pulling out of the alley and into the streets.
The afternoon passed by quickly for Sandra, having acquired all of the
ingredients for the night's operation. She was in the process of
finishing the lamb chops for dinner. Derek always seemed to be watching
his back, so Sandra would really have to work at letting his guard down.
An acquaintance said that the path to a man's heart is his stomach, so
she decided to plan for that angle. However, Alyssa's advice to her also
said their libido worked as well, so that's where plan B comes in,
taking the form of Sandra's brand new red minidress. She had even cut it
extra short for maximum appeal. With hope, Sandra would lure him into a
false sense of security. Then she'd deliver the wine and all will be
well in her world. Sandra glanced over at the clock. 6:28 PM. Derek
would arrive any minute. With haste, she put together the dishes, laying
them out on the table. A few raps on the door announced Derek's arrival
as Sandra dashed down the hallway, tossing her apron aside on her way.
"Come in!" she said, making herself sound as cheery as ever. Derek let
himself in, opening the door locks one by one. This gave Sandra enough
time to change into her new dress.
Once in the room she flung her clothes off, slipping out of her sweater
and jeans. She unclasped her bra, lightly launching off her body from
the tightness around her bosom. She slipped the minidress on, filling it
out with her curvaceous form. A quick tug of the skirt revealed her
bare, thick legs. A quick adjustment placed her tits in the bodice,
putting her cleavage on display. The fabric was taught enough about her
breasts, allowing her nipples to slightly poke through its fabric. "Not
like this hasn't happened around him before," She thought, slipping her
heels on. One last look in the mirror to check hair and makeup, and all
was well. Time to make her entrance.
Meanwhile, Derek stood about the apartment's living room, examining
everything around him. He didn't know what to expect from this dinner,
let alone something like lamb chops. Taken aback by her efforts, he sat
down at the table. Needless to say, Derek wasn't ready for what came
next.
From down the hall came Sandra flaunting her red silken minidress. With
each step her hips swung out to the side in tantalizing fashion, her
breasts bouncing beneath her top. It's a miracle they haven't disrobed
yet, given how little the dress actually covers. Derek couldn't help but
gape at her voluptuous body practically seeping with sensuality.
"Hey Derek, glad you could make it," purred Sandra, sauntering over to
the table. This struck him as a little odd, given the forced nature of
their relationship, but Sandra's jiggling tits were the only think Derek
could focus on.
"Oh, of course," is all Derek could muster after a few seconds, finally
coming back to his senses. "Right, I wanted to talk to you about someth-
."
"Let's not let our food get cold now," scolded Sandra. Derek was
surprised, where did this side of Sandra come from? Usually she just
kind of ignored him. "Perhaps we can finally cooperate," thought Derek.
"I suppose I'll play along."
The two began eating. Derek was enjoying his meal as Sandra was closely
watching him. As if she was reciting lines from a play, Sandra made
small talk with Derek, topics that she was sure to keep him busy. Mostly
stories from her work, which was enough to keep his attention. Sandra
was also sure to bend down or adjust her dress, just enough to let him
glance at her plump tits. Soon enough, the two of them were finished.
"That was a fine meal," thanked Derek. "Although it didn't look like
you've eaten much."
"Oh, I didn't have much of an appetite," said Sandra. Truth was she was
too anxious to eat. "I could go for a glass of wine, though. What do you
say?" Sandra asked, grasping a few glasses.
"I really shouldn't..." said Derek, shying away.
"Oh come on, loosen up a little. I cooked you a 'fine meal', the least
you can do is have a drink or two with me." With a soft pop, Sandra
uncorked the wine, pouring the maroon liquor into a pair of glasses. "Go
on, have a seat," said Sandra, guiding him to the couch, allowing her
ample breasts to press against his back.
The two sat down on the couch as Sandra handed Derek his glass. He cast
a suspicious glare into the full-bodied wine.
"What are you gawking at it for, drink! I haven't poisoned it, if that's
what you're worried about," Sandra joked, downing some of the wine. "At
least, not yet," she thought. Alyssa's contribution to tonight's plan
was still hidden, the capsule was held in a plastic bag, snuggled
between Sandra's considerable bosom, and one sip of any drink with that
added in would knock even the most iron-willed bruiser out. Although, it
wouldn't be bad to enjoy a drink or two before dropping in Sandra's
little helper, it looked like Derek was still suspicious.
Derek took note of Sandra's gulp, and figured that he could use a drink.
He admired the blush creeping over her already rosy cheeks, and took a
considerable drink of his own, exhaling harshly as he set the drink
down.
"That's more like it!" Sandra said, clapping him on the back. She
allowed her hand to rest on his back for a second, her nails grazing his
shoulder as she retreated back to her own glass. Sandra then continued
story from before as they drank. Derek continued to ogle Sandra, who
pretended not to notice. She would cross her legs, hiking the miniskirt
up further and further, giving Derek a full view of her thick thighs.
However, Derek wasn't the only one gazing. Sandra was beginning to feel
the wine, having never been a strong drinker even as a man, and couldn't
help but feel a stirring within her. The warmth was back, her imbibing
increasing her arousal. Her nipples stood at full attention beneath her
blouse, but Sandra no longer cared. Right now she had to focus on the
mission, no matter how strong her desire was. She brought the glass to
her lips to find that it was dry, as well as Derek's.
"Would you look at that, look like we're due for a refill. Don't you
bother, I'll get it," Sandra announced, the glasses clinking in her
grasp. Her steps became wobbly, as the alcohol seemed to cut through her
weeks of high heel training. She turned a corner out of Derek's sight to
the strategically placed bottle, and poured another two glasses. Sandra
dove a dainty hand beneath her tits and procured a small plastic bag,
the capsule suspended inside.
"Oh Sandra, I remembered what I was going to tell you from earlier..."
rang Derek's voice from the other end of the hall. Startled, Sandra
nearly dropped the bag right back down her dress, clasping it between
her hands.
"Y-you can tell me all about it in a minute," Sandra said, fumbling with
the bag.
"I just figured you deserved some answers after I kept you here. I've
been evasive for a reason, but I think now's the time to clue you in."
Now this piqued Sandra's curiosity. She was a bit worried that her
departure wouldn't answer any of her questions, might as well find out
over one more glass of wine. Sandra slipped the bag back between her
bosom and returned to Derek, presenting him with a new glass of wine.
"Alright, go for it," replied Sandra, plopping back down on the couch.
Before she has sat on the other end, but now Sandra was right next to
next to Derek, almost uncomfortably so. Derek showed no sign of backing
off, so she stayed her place.
"Jeez, where do I begin?" mumbled Derek, taking a swig of wine. "I guess
if I were to summarize this whole thing up, it's that I did all this to
protect you, you know?" Derek's voice took on a wavering tone, most
likely from the wine. "I may have forced my hand a little, but it's
true."
"Yeah, right," though Sandra, sipping her own wine.
"Long story short, back when you were, er, Shane, you saw something you
weren't supposed to see, remember? It was that rainy night after we met?
Well, you were just in the wrong place at the wrong time. I knocked you
out and dragged you here. The alternative was to kill you, and I was not
about to do that, not after you went out of your way to help me."
Sandra thought back to that day at the diner, throwing in a few bucks
for his dinner. "Oh stop it," she said dismissively. "It wasn't anything
big, just helping out a stranger."
"Hey, when you're working for who I was working for, a little kindness
goes a long way. Anyways, I couldn't just leave you there, you were
close enough to their operation as it were, they'd find you soon enough.
So now it's my responsibility to play witness protection program, and I
figured they wouldn't find you if you weren't, well, you. So I snatched
the device that they were working on, and used it to change your
identity."
Suddenly, Sandra felt a fluttering in her chest. She should be furious
at this man for ruining her life so casually, but she couldn't help but
feel touched by his consideration. Perhaps it was the wine, maybe it was
her arousal. Either way, Sandra had not planned for this.
"I knew they'd end up looking