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Roulette Blackmail - 3
by Illicit Writer (illicitwriter@hotmail.com)

***

In chapter three of our story, Glen's plans of blackmail 
continue. (MF, voy, nc, mast, oral, blkmail)

***
 
Chapter 3 - The Second Hurdle

As Glen pulled into his driveway, he saw his sister-in-
law's car. A small ball of tension began to form in the 
pit of his stomach. Had Lauren felt guilty and 
confessed? When he walked into the house, he thought he 
felt tension in the air. His worst fears were confirmed 
when his wife, Kim, came up to him with a pensive look 
on her face. Over her shoulder, he saw a satisfied smile 
on Lauren's face.

Confusion roiled through Glen though when Kim gave him a 
hug and a peck on the cheek. "I'm so sorry hun. Lauren 
was showing me some web sites from your laptop and I 
accidentally spilled soda onto it."

"Don't cover for me sis." Lauren walked up with a faux 
look of sadness. "It was my fault Glen. We tried to dry 
it out, but it's completely trashed."

Glen slid his arm around his wife's shoulder and gave 
her a squeeze. "It's no problem Kim." He sheepishly 
unslung the bag from his shoulder. "I know I should have 
told you but I picked up a new netbook last week." He 
pulled out the slim black computer. "Look how small it 
is and it holds the exact same amount of memory as my 
laptop!"

Kim let out a relieved laugh. "Whew! Well I guess I 
should be mad, but I guess it's just fate."

"Yeah... fate." Glen looked over at Lauren. "Are you 
staying for dinner Lauren?"

"No... no, I have to get going." Lauren grabbed her bag 
and headed for the door.

Kim turned back to her husband. "I could've sworn she 
was planning to stick around longer. She can be so moody 
sometimes."

Lauren,

Well clearly you still need some discipline. You will be 
ready for me on Saturday at 9pm. Requirements for the 
night are: 1. you must buy at least two more sex toys of 
your choice 2. You must completely shave your pussy 

An email from her popped up about an hour later.

Well I had plans but I'm guessing you won't care about 
that will you? Fine. What should I wear?

Glen typed up a quick reply. Doesn't matter. Something 
comfortable.

Then he shut down his computer... he had his own 
shopping to do.

The Saturday night was warm and clear as Glen buzzed 
Lauren's condo. 

"Yeah?"

"It's Glen."

"OK, I'll be right down."

"No, I'll come up." 

The door buzzed and Glen rearranged the back pack and 
brown bag he was carrying to turn the knob and made his 
way up the old brown stone's creaking stairs. He was 
about to knock on the door when it swung open. Lauren 
was there, looking defiant and dressed in illini sweats.

He eyed her up and down and she thrust out her chin. 
"You said to dress comfortable."

Glen nodded. "So I did. We are going to stay here 
anyway." He tossed her the brown bag. "Go into the 
bathroom and try this on. I'll wait out here."

Lauren peeked open the bag and opened her mouth. 
Suddenly, though, she merely turned and stomped down the 
hallway.

He walked into her bedroom and unzipped his backpack. He 
moved quickly to boot up his computer and grab her wi-fi 
signal. He was just finishing getting the webcam up and 
running when he heard the bathroom door open.

He turned and whistled. Lauren came out dressed in the 
lingerie he had provided. The black lace gathered at the 
neck, almost like a collar before falling into two 
leaves that barely covered her boobs. The panties had a 
black bow and clearly revealed that she was, in fact, 
clean shaven. The outfit ended with black thigh highs 
that emphasized the curve of her hips.

When she saw the cam and his computer, she stopped and 
started to back away. "No, not this..."

He chuckled and reached down into his backpack. He 
pulled out a black mask, the kind seen at masquerade 
balls that cover the top half of the face. This one had 
a small, black feather sticking up from the left side. 
"Don't worry Lauren. I said three hurdles and I won't 
ask you to expose your identity for any of the hurdles."

Tentatively, she took the mask and put it on. She 
glanced at herself in the mirror. "I guess it works ok."

Glen came up behind Lauren and deliberately turned her 
around. Keeping eye contact with her, he slowly put his 
hands down the front of her panties. He felt only bare, 
smooth skin. He continued down until he reached her 
slit. It was warm and wet.

"Glad you followed directions. See? I even got rid of 
the distinctive heart shaped hair patch of yours. Now 
where are the toys?"

Silently, she went to the end table next to her bed and 
pulled open the drawer. Glen moved over and saw that in 
addition to the purple, cock shaped vibrator, there was 
a silver egg and a thin, red vibrator that was a simple 
wand shape. He gathered them up and then moved over to 
the bed. He laid out the toys and noticed the framed 
poster of a Manet above her bed. He took it down and 
leaned against an adjoining wall. He motioned for her to 
come over.

"Tonight's hurdle is very simple. I am going to start up 
a video chat on an adult website. Once we start 
broadcasting, people will take a look. You will act the 
horny nympho and then do whatever they say."

Lauren sat down on the bed, she looked down at the toys 
next to her, unsure. "How will I know what they want? I 
can't read the text on the screen."

"My netbook has speakers and a mic. If they have a mic, 
you'll be able to hear their comments... and they can 
hear you." He moved away from the bed and opened the 
browser to the adult site. He started typing. "I created 
a user name for you. HotnHorny22. I admit it lacks a 
certain originality but it gets the idea across." He 
clicked a button and watched the video camera start to 
buff. He then opened his recording program and quickly 
minimized it. "Alright we are live in... 3... 2... 1!"

Glen peeked at the computer screen and watched Lauren 
fidget on the bed. Even uncomfortable, she looked 
incredibly hot. The inside of her breasts peeked out 
from beneath the black lace. 

"You look uncomfortable not horny," Glen reprimanded 
her.

"What should I do?"

"What does a person do when they are horny and by 
themselves?"

Lauren looked away. Sheepishly she moved her hands 
slowly down her breasts down to her ribs and stomach 
before finally ending between her legs. Her fingers 
moved between her legs. 

Then her arms flew up in the air with frustration. "I 
feel silly!"

Glen shook his head. "I was going to let you have a few 
drinks first to relax, but after the stunt you pulled a 
few days ago... well, you'll do this sober and you will 
do it well."

Lauren open her mouth in protest when they both hear a 
bleep from his computer.

With static but still clearly heard, a voice spoke. 
"Wow... hot baby!"

Lauren looked with fright at the cam and back to Glen. 
He mouthed. Wave. 

She waved and gave a half smile at the cam.

"Dance for me babe... let's see that body in motion."

Lauren moved up on her knees. Tentatively, she began to 
sway her hips.

Bleep.

Another viewer popped on.

"Hot Bitch!" A rough male voice came through. "Dance, 
bitch! Dance!"

Lauren moved a bit more... her hips swayed a little more 
but she was clearly still uncomfortable. Her mouth 
peeked out below the mask with a little frown. Her hands 
were held awkwardly to the side.

Bleep.

"A little dance show, huh?"

A spark of life finally entered Lauren's movements. Glen 
couldn't place it, but the sway of the hips became more 
sensual. She gyrated for the camera and her mouth gave a 
hint of smile. Glen glanced at the screen and saw a 
video box had popped up. A cock being stroked dominated 
the screen.

The first voice chimed in "Baby, let's see your 
breasts."

Lauren's hands moved up her sides. They playfully tugged 
at the sides of the lingerie but didn't quite reveal the 
treasures beneath.

Bleep.

"Jack pot! Show your tits! Show your tits!" 

Lauren did smile now. Her hands clutched at her breasts 
through the black lace. They were just more than 
handfuls for her and bulged past her fists. Slowly she 
ran her tongue along her lips and started to gyrate more 
swiftly. Her body began to move up and down.

Bleep.

Another user came on and, almost immediately, another 
video popped up – again of a stroking cock. This even 
caused Glen to give a double take. It was easily the 
biggest cock he had seen. The man stroked it with two 
hands and there was still ample left of the cock to see. 

"Let's see those breasts already!!" A disembodied voice 
panted.

But now Lauren's confidence was building. She shook her 
finger no, before returning to kneading her tits. Her 
body was beginning to move up and down now, air fucking 
the bed. She teased out her nipples through the fabric. 
They could partially be seen now between the pattern of 
lace. Her hand snaked down and once again she partially 
flashed her tits before covering them with a smile.

This time her hands snaked towards her panties. One 
finger moved beneath the materials and then rode the 
edge. 

"Oh yeah!"

"I bet you have a hot pussy!"

"Finger it bitch!"

Her finger did dip deeper... the barest hint of sliding 
inside of her. She pulled out her hand and let it travel 
slowly up her body until it came to rest in her mouth. 
She lifted her chin and sucked her finger in and out...

"Damn!"

Glen could clearly hear the whacking of the watchers and 
Lauren did too. Gone was the nervousness from before. 
Instead, a sexy woman was beginning to emerge.

"Show us those tits! Please!"

Lauren smiled and slowly grabbed each edge of her . Her 
hips moved to a faster beat and she brought back the 
material to reveal her spectacular breasts. Perky pink 
nipples danced from the jiggling of her full and firm 
breasts. 

Cheers exploded from the computer. Lauren nodded in 
acknowledgement and moved her hands to her naked tits. 
She circled her nipples before cupping her breasts. 
Playfully she jiggled them for the camera. Her hand went 
down her sides and hooked the sides of her panties. 
Playfully she pulled them down and inch.

"Yes!"

"Take 'em off bitch!"

"Let's see it."

Lauren shook her head coquettishly. On all fours she 
crawled closer to the camera before once again she 
jiggled her breasts. She moved over to her nipples and 
began to circle her nipples. Finally, the fingers closed 
in on the nipples and squeezed. They then began to pull 
them, she bit her lip but kept pulling.

"That's hot!"

"Pinch them good!"

She did, leaving red marks crisscrossing her nipples. 
She bit her finger playfully.

"Are those toys on your bed?" At Lauren nod, the man 
commanded. "Let's see them."

She held up all three and waved them in front of the 
camera.

"Use the purple one!"

"The silver one!"

"Stick it in your pussy!"

"Suck on it!"

Lauren laughed as all the contradictory commands came 
in. She kept the purple one and had it trail over her 
body. She put it between the breasts and squeezed them 
around it.

"Suck it!"

Lauren gave them a wicked smile and then slowly inserted 
the toy into her mouth. She groaned and then pulled it 
out so she could twirl her tongue around the tip of the 
toys. She leaned forward, towards the camera, and began 
putting the toy in and out of her mouth. 

Glen watched the cock shaped toy move beneath those lips 
and couldn't resist. He unzipped and pulled his own cock 
out. Lauren's eyes swiveled upon his hard on and the 
smile on her face grew bigger. He stroked his cock as he 
watched Lauren's oral show. She'd deep throat the toy 
for a few beats and then would nibble along the sides of 
the shaft or twirl her tongue around the tip.

"Put it in your pussy!"

"Fuck that toy!"

"Fuck it!"

Lauren moved on to her back. She teased down her 
panties... moving them down before bringing them back 
up.

"Please!"

"Show that hot pussy!"

"I beg you!"

Her hips gyrated as she finally slid down her underwear. 
With a flick of the wrist, she tossed it to the side and 
then grabbed her toy again. She twisted the base and a 
distinctive hum filled the room. With legs splayed, her 
shaven pussy was on display. Glen could see that she was 
already wet, confirmed as the purple toy sank into her 
pussy immediately.

"Woohoo!"

"Fuck that toy!"

The toy was soon slick as Lauren pumped it in and out of 
her pussy. A soft groan escaped her and Glen was 
positive it wasn't for the benefit of her audience. Her 
hips moved up as the toy pushed down. 

"Ohh... that feels good!" Lauren gasped. Her one hand 
kept up the rhythm of her toy while the other snaked up 
and began pinching her nipples. Another long moan 
escaped her lips. Her stocking-clad thighs twitched as 
pleasure ran through her.

"I want to see a toy in your ass bitch!"

Lauren blinked her eyes open with a groan of 
disappointment. Glen saw that comment had broken through 
her own concentration interrupting the wave of pleasure 
that had begun to build.

"I–I... haven't put anything... I don't have anything 
for..."

Glen reached into his bag and smiled to himself. He 
grabbed a bottle of lube and tossed it onto the bed. 
Lauren looked up at him. He motioned to the other toys. 
"Use it on the red one."

"Who is that?"

"Your boyfriend is there?"

"This is some kinky shit!"

Unsure, Lauren picked up the lube and started to read 
the directions on the side of the bottle.

"You dumb ho? Get that toy in your ass."

"Have your man help you out."

Lauren fumbled with the toy. Glen sighed and reached 
into his bag for the second mask. This one was dark 
green. He slipped it on and then walked towards the bed. 
He glanced at the computer. There were four stroking 
dicks on the screen now. He grabbed the lube and red toy 
from Lauren's grip. 

"Yeah man! You give it to her good!"

Glen smiled. "You heard the good men... get on all 
fours, ass towards the screen."

Lauren whispered, "I don't know if I can do this."

"Remember... this hurdle you have to do everything they 
say."

Hesitantly, Lauren turned over. Glen reveled in the 
site. The black lace thigh highs ending in creamy white 
thighs. He ran his hand over the curve of her ass. He 
gave it a sharp smack and heard a satisfying intake of 
breath. 

He popped open the bottle of lube and placed it at the 
top of the crack of her ass. He heard cheering as he let 
the lube trail down. He stuck his finger at her opening 
of her asshole. The lube pooled around his finger and he 
pushed into her ass.

"Gently..." The whisper from Lauren was barely audible.

His finger withdrew to gather more lube and then pushed 
in to the knuckle. Her asshole was so tight and hot. 
"Get on your elbows and push that ass out further. Give 
the boys a good show."

Without a word, Lauren complied.

Glen pushed his finger all the way in now. He kept the 
strokes slow and even, making sure she got used to the 
sensation. The ring collapsed around his finger as he 
stroked in and out and he gave her firm ass another 
smack. Was it his imagination or did she raise her ass 
even higher in response?

"Get that toy working!"

"Fuck her ass!"

Glen pulled out his finger and grabbed the thin, red 
vibrator. It slightly flared at the base but should be 
perfect for anal invasion. He ran some lube over it, 
making sure it was well coated. He turned to the cam and 
gave a thumbs up. Whoops and laughter responded through 
the computer.

He turned back to Lauren and set the toy against her 
back door. There was slight, initial resistance but Glen 
gave a little push and the toy smoothly slid in. With a 
smile, Glen turned the base. Lauren gasped as the toy 
began to hum. Glen began to sliding the toy in and out 
of her ass. He spied the purple toy just beyond her 
knee. As he kept sliding the one toy in and out of her 
ass, Glen turned on the other toy. He moved it against 
her clit first, moving in small circles.

Lauren's breathing began to get uneven.

"Whew! This is hot!"

"Fuck yeah!"

With a shove, Glen pushed the vibrating toy deep into 
her pussy.

"Ohhh... Yes!!!" 

It was Lauren who screamed.

Glen looked at his sister-in-law in surprise. His own 
wife, Kim, had always been very quiet during sex and 
Glen had assumed her sister would be the same.

He started moving the toys in and out of her pussy and 
ass at the same time. Now, Lauren's ass pushed back, 
moving in rhythm of the toys. Wetness began to leak out 
of her pussy.

He saw one of her hands snake up to her tits that swung 
back and forth. She twisted her nipple as she continued 
to fuck the toys.

"Faster please! Faster!!" Lauren begged in between 
pants.

Her legs began to shake and Glen knew she was close. He 
plunged the toys in and out of her, watching her ass 
lunge back. He let go of the purple toy and gave her ass 
another smack. It jiggled delightfully. 

"Yes! Another!"

He smacked the ass again. 

Lauren's ass began trembling and her legs shook. Glen 
took the purple toy and angled it sharply down so that 
it pressed against the clit and g-spot. He sawed it 
violently back and forth. Smack! Her ass began to glow 
red. Smack!

"Yes! Fuck! I'm coming!" 

Wetness spurted out the sides of the vibrator and the 
red toy spiked up as her muscles clenched. Glen watched 
Lauren groan in pleasure and pull at her nipples one 
last time before collapsing on her stomach. The toys 
still obscenely hung in her orifices. Glen caressed her 
ass gently.

On the computer screen, video boxes clicked off as men 
disconnected. But one watcher in particularly stayed on.

"Bitch! Your man just gave you a gift. You better thank 
him before he whips your ass instead of just those love 
taps I just saw."

Lauren raised her head, slightly dazed and her hair half 
covering her mask.

"Take his dick out and give it a good long kiss."

Glen gave silent thanks to that man as he felt Lauren's 
hand fish into his unzipped pants and pull out his cock. 
Without a word, she swallowed his half-erect cock in one 
motion. He reveled in the sensation of her warm, wet 
mouth. He felt himself respond quickly and was soon at 
his full seven inches.

Her neck was at an awkward angle though, so she pulled 
herself onto her hands and knees again. With a soft 
plop, the toys fell out of her ass and pussy.

Bleep. Bleep. Bleep.

Their show was garnering some attention again. Video 
boxes popped up on the computer screen.

"Lick his balls!"

Lauren interrupted her sucking and turned to the camera 
and smiled. She lifted his cock and stroked him before 
burying her face into his crotch. He felt a warm sliver 
engulf his left testicle. Gently she pulled it with her 
mouth before moving to his right ball. Her tongue 
playfully swirled around his sack. Glen was in heaven. 
His wife tended to be quick with the blowjobs, sticking 
with quick up and down motions of his cock until he 
came. No nibbling. No foreplay. And certainly no ball 
play.

Lauren moaned as she played with his balls. The 
vibration shivered pleasured up from his groin. Glen 
leaned back and closed his eyes, concentrating on the 
magic of her mouth. She left his balls and began to lick 
her way up the underside of his shaft. Quick, delightful 
sensations of pleasure. Each lick brought her closer to 
the crown of his cock. 

"Get that toy back in your ass!"

Glen felt a wave of disappointment as Lauren's mouth 
left his cock. He looked down to see her looking at the 
computer screen. For a moment, she appeared frozen, but 
then slowly, incredibly, he watched her reach behind. 
She picked up the thin, red toy and inserted it back in 
his ass. Her wrist turned and he heard the toy hum back 
to life.

Her mouth returned to his cock. Again, she didn't dive 
in but nibbled up and down the sides of his shaft. He 
looked down to see that she was looking at him. She 
blinked away and this time engulfed him in her mouth. He 
watched as his cock moved in and out her mouth, 
unconsciously his hips began to move back and forth.

"Fuck her mouth!"

"Oh yeah that's it!"

"Grab her hair bro!"

Glen put his hands on the back of her head. Slowly, he 
let her hair intertwine his fingers and he began to pull 
her head towards him. Sharp, repeated thrusts and he 
felt his cock pushing farther and farther into her 
mouth. He felt his climax begin to build and let go of 
Lauren's head, letting her keep up the rhythm. 

"Fuck her!"

"Yeah, fuck her!"

Glen leaned towards the screen. They had quite an 
audience now. 

"Tap that ass!"

He felt the warmth of her mouth leave and Glen looked 
down to reprimand Lauren. However, the 22 year-old was 
spinning around on the bed until his cock was only 
inches from her hot pussy.

"I need to be fucked!"

Glen pushed himself all the way in. He was fucking his 
sister-in-law! Buried deep within, he felt more than her 
hot, tight tunnel. There was a weird sensation and he 
realized he could feel the toy in her ass! That set him 
off. Glen started to pound away. He spanked her ass 
repeatedly until it was a warm red glow.

"Yes, just like that! It feels so good! Fuck me!"

Lauren was screaming now, pushing herself back to meet 
his thrusts. Glen was transported by the feel of her 
pussy – so much tighter than his wife's. He felt himself 
getting close again. The vibrating added new trembles of 
pleasure every time he sank himself to the hilt.

There was a red mark on her ass from his hand, and she 
groaned in pleasure with every smack.

"So close! So close!"

Glen saw the telltale twitching and thrust faster. He 
was riding his own edge of pleasure. Finally he felt her 
pussy clinch his cock!

"Yes! Right there!"

He grabbed both hips and gave one final thrust to unload 
deep inside her. The toy continued to send ripples of 
pleasure and he stayed inside of her, not wanting the 
orgasm to fade into memory. He let his hands wander over 
her ass, the smooth touch of the thigh highs, the curve 
of her hips.

He pulled out, spent. Faintly he heard catcalls and 
cheers from the computer. But he watched in awe as 
Lauren turned around and met his gaze. Without breaking 
eye contact, she moved down and began to clean him with 
her mouth. Slowly, she moved her tongue along his balls. 
Her hand cradled his deflated penis and she took him 
into her mouth. Over every inch until it was clean.

Then and only then did Glen go over to the computer and 
shut it down.


Part Four coming soon.... "The Third Hurdle"

Let me know what you think. illicitwriter@hotmail.com

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

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Kristen's collection - Directory 67