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Roulette Blackmail - 2
by Illicit Writer (illicitwriter@hotmail.com)

***

Glen continues his blackmail and looks to see how far he 
can push his victim. (MF, exh, nc, bi, oral)

***

Chapter 2 "The First Hurdle"

Glen looked over his email before sending it out. It was 
essential that he get the wording just right so that his 
sister-in-law would do his bidding.
Lauren,

It's time for your first hurdle!

There is a jazz bar on Lawrence called the Green Mill. I 
want you to show up there on Tuesday at 9 pm. 

Requirements for the night are: 1. A dress that does not 
go below the knee Happy times!

He didn't have long to wait for an answer. Twenty 
minutes later he got his reply.

You think I'm going to trust to meet you face to face? 
Fuck off!

He smiled at her spirit, but knew that it was time to 
stake out his authority.


Lauren,

Tsk, tsk, tsk. I could have ordered you to a deserted 
parking lot. I could have ordered you to get drunk 
first. 

I could have sent your naked video to your parents. Your 
dad is rather strict, isn't he? 

Instead I gave you an easy place to meet.

For the attitude, I will now add requirements: 1. You 
cannot wear bra or panties. 2. Your dress must not only 
end above the knee but it also has to show cleavage.

Any more attitude and...

*

Glen thought of a half a dozen threats, but decided in 
the end that Lauren was a creative woman. She could 
probably come up with more effective threats with her 
imagination than he could ever conceive of.

After sending off the email, he opened up the video of 
Lauren masturbating. There wasn't any incriminating 
evidence like in the first video. But in this one Lauren 
had come and had come hard. He edited the video so that 
the first and second were side by side. It was easy to 
see that they were the same person. The same full 
breasts, the same perky nipples, perhaps most 
incriminating, the same heart shaped pubic hair. He felt 
himself stirring once again. 

He glanced at the clock, he had a half hour at least 
before his wife came home. The body on the screen 
undulated before his eyes. The body was so like his 
wife's, but Lauren was a few inches shorter than her 
older sister Kim. Her breasts a bit fuller and her hips 
a bit wider. Glen wasn't sure if it was the differences 
or similarities that turned him on more.

Lauren's purple toy plunged in and out of her pussy with 
passion now. Her juices shining on its shaft and then 
Glen erupted in orgasm. 

By the time his wife, Kim, came home, he was in the 
kitchen putting the finishing touches on dinner. He 
yelled out welcome and she came into the kitchen and 
collapsed into a chair. 

"Tough day honey?"

"Yeah." Kim lifted up her briefcase. "And more work 
tonight. Listen I know we talked about having sex 
but..."

Glen leaned over and kissed her forehead. "Shhhh. Don't 
worry about it."

His wife smiled and said, "Thanks hon. Don't worry. I've 
blocked out work for your birthday. I'll make it up to 
you then."

"Speaking of late nights. Tomorrow I'm meeting some guys 
out in the city so you are on your own for dinner." Glen 
went back to the stove and stirred the pot.

The Green Mill was a small bar, but dark. A jazz band 
played on a stage opposite the door with intensity that 
filled the bar. Glen positioned himself just around the 
bend of the bar so he could observe the entrance but 
also not be seen right away.

When Lauren came in, her eyes blinking to take in the 
interior, Glen's cock twitched. She wore a black dress 
that clung to her body. Occasional sparkles drew 
attention to the attractive curve of her hips and a 
neckline the dipped down her chest. He let her wander in 
for a bit before making his move.

"Lauren!" He walked up to her and gave her a hug.

"G-G-Glen... what are you doing here?" She furtively 
glanced around the bar.

He let her confusion boil over a few beats more before 
leaning over to her and whispered in her ear. "Happy 
times."

Her eyes widened and then hardened. "It you? Fuck! When 
my sister hears of this –"

He grabbed her arm and propelled her to a corner table. 
He sat her down forcefully and moved in after, trapping 
her between the table and wall.

"Yes it would be very tragic if Kim heard of this. She'd 
probably even divorce me." He saw a whisper of triumph 
cross her face. "But I think that pales to when your 
parents disown you when they see the video. How do you 
think your school district would react? You teach high 
school kids, right? I'd imagine 17 year old boys would 
love to know what their teacher does..."

"You've made your point asshole." 

Her face ducked down and Glen saw she was on the verge 
of tears. That would not do at all. He reached for her 
chin but stopped when she flinched. Instead he 
whispered, "I picked this place because we could talk 
and chill here." A waitress came by and he ordered two 
vodka martinis. "Let's sit and listen to some great 
music and share a few drinks."

Lauren nodded hesitantly.

"But before we do that... I see that you followed my 
instructions, but did you follow ALL of them?"

Her breasts swelled as she took a deep breath and then 
nodded. 

He took her hand pressed black lace into her palm. "Go 
to the bathroom and put these on and then let's sit and 
listen to music."

She looked at him puzzled, but he merely scooted out and 
smiled. Hesitantly, she moved out and walked to the 
bathroom. Glancing back, he nodded to her with 
encouragement. Presently, Lauren returned and Glen made 
sure she was wedged between him and the wall. The bar 
began to fill up as the band continued with their set. 

Soon couples were sharing tables as people tried to 
squeeze into every available space. Lauren was pressed 
up against Glen but refused to make eye contact with 
him. Instead she sipped her martini slowly. Glen leaned 
against the wall, not pushing himself against her or 
trying to engage her in conversation. 

An hour passed and the band took a short break. 
Conversation grew to replace the music, the waitress 
brought them their second round, and Glen placed a small 
black remote on the table.

He spun it on the table. "Well Lauren, it's time we 
started the first hurdle. I'm going to move my hand 
below the table to check that everything is in order. 
You will not move. Do you understand?"

He waited for her nod before moving his hand below the 
table top. As squeezed in and as dark as it was in the 
bar, there was no way anyone could know what he was 
doing. He saw Lauren come to that same conclusion. He 
let his hand rest on her thigh feeling her warmth 
through the dress' fabric. He slowly moved it down until 
he reached bare skin. Her thigh was smooth as he traced 
his fingers down the inside of her thigh and then up. 

When he reached the hem of her dress, he half expected 
her to make a sound, but there was no resistance. The 
heat built as he moved up and felt both thighs begin to 
squeeze against his hand. Glen forced them to part and 
continued on his way. Lace fabric met his finger tips 
and he smiled. He let his fingers follow the edge of the 
underwear down until he was satisfied that Lauren's 
pussy was fully within the confines of his present to 
her. 

He was tempted to let his fingers rest in that sweet 
spot or ever press in a little bit. The plan Glen, stick 
with the plan. Regretfully he moved his hand back until 
it was merely caressing her thigh. With his other hand, 
he picked up the remote.

Glen leaned over and whispered, "This is a remote for 
your panties. When I pressed the button – "

Lauren immediately jerked forward, almost spilling the 
full martini. "What?!"

Her outburst turned heads and Glen softly chuckled 
pretending it was some sort of joke. "As I said, when I 
press this button those panties will vibrate your whole 
pussy. But you'll be happy to know that I spent a little 
extra for a nub particularly for your clit."

Lauren grabbed his forearm. "It's too intense! How am 
I..."

The rest of her words were lost as she gripped his arm 
tighter in response to his second round of stimulation. 
He watched her bite her lip and close her eyes. He 
thought he saw a hint of nipple rise against the fabric.

He did press against her now and leaned towards her ear. 
"Now tell me why you thought I was Leslie at first."

Lauren blushed and shook her head. "Oh, that was 
nothing. Just a silly..."

He clucked softly as he pressed the button a third time. 
This time there definitely were two nipple points 
pressing against the dress. 

He shook his head. "You thought it was a sorority sister 
trying to blackmail you. And not only that but to also 
see you naked."

At her hesitation, he pressed the button again. She 
gripped the table with both hands, but her body was 
adjusting to the extra stimulation. Her mouth went slack 
for a second and then she looked up with pleading eyes, 
her chest heaving, and he relented with the remote.

"Showing myself cam kind of... started while in 
college." Lauren took a sip of martini for courage. 
"Leslie was my roommate and we had come back from a 
sorority social meeting which meant one of our sisters 
had just broken up with a guy. The night consisted of 
trashing men and getting trashed.

"Les and I were still too wound up when we got back. So 
we made a pitcher of margaritas and she pulled up a site 
where we could video chat with people... not roulette 
that hadn't been invented yet. I am pretty sure Les had 
been on there before but we sat and watched some people 
streaming. Mostly guys and stroking their cocks... one 
couple who were full on going at it... We'd flash the 
people occasionally. 

"Then a woman in her 40s IMed us. I opened a video 
window not knowing it was just a single woman. I was 
about dismiss her when she typed in asking if we were 
girlfriends. We both laughed, but then Leslie grabbed 
the back of my head and laid a long , deep French kiss 
on me. I went with it and when we turned back, the woman 
applauded our efforts. She was striking... I remember 
dark hair with the lightest blue eyes. She typed in that 
she was glad to see women realize their true path so 
early in life.

"She then pulled up something and asked if we had one. I 
leaned closer... it was a dildo! At that time I didn't 
know much about them. This one was huge, maybe 10 inches 
long. I leaned forward to get a better look and I felt 
Leslie's hands move under my shirt. Oh!"

Glen couldn't resist giving her a little buzz. Lauren 
took a large gulp of her martini and he felt her leg 
twitch against his. Did she press against his body? Glen 
decided to play it safe and remained silent.

"I was about to turn to look at Leslie when I saw the 
woman typing again. She asked if she could play with the 
toy while watching us." Lauren laughed, a huge smile 
across her. "She even said please!

"Les reached with her free hand and typed YES! I began 
to ask her what she was thinking but she cut off all 
words with a kiss. Like the first, her tongue pressed 
against mine. I could feel her body, softer than a guys 
press against me. Her hands were all over me... I felt 
embarrassed and uncomfortable. But I looked at the 
screen and saw the delight on that woman's face. She 
flashed me a smile that sent a shiver of pleasure down 
my spine."

Lauren took another long pull from her martini. Glen saw 
her eyes flicker to the remote. Did she want him to 
press it again? He glanced around the bar. He had almost 
forgotten the crowd in the bar. He briefly made eye 
contact with the couple across the table. How much could 
they hear through the noise?

But Lauren was already continuing on with her story.

"I didn't resist as Les pulled off my shirt. Her lips 
moved along my neck. I felt teeth gently nibble my skin 
and it was like raindrops of pleasure. My entire body 
felt alive. I barely notice as Les pushed me back on the 
couch. I looked down and saw my friend push up my skirt 
and practically rip off my underwear. It was like some 
sort of dream. I looked back at the monitor and saw the 
woman on her back now, working her toy in and out. But 
her eyes, those blue eyes, were met my gaze and that is 
when I felt Les' tongue along my pussy."

Glen pushed the button and Lauren gripped the table. But 
he realized that she wasn't gripping the table to 
control her reactions, instead she was pushing herself 
down, reveling in the vibration coursing through her 
body.

"Les kept whispering how beautiful my pussy was, but I 
could barely hear anything over my own breathing. I felt 
a finger move into me as her tongue circled my clit. I 
tell you I was so wet I would have been embarrassed but 
I was lost in the gaze of that woman. She was so happy 
watching us. I moved my fingers through Les hair, 
pulling her face closer. I felt another finger enter, 
pressing hard into me. My clit was thrumming from her 
tongue.

"I felt my climax building... but then Les moved back. I 
looked down and saw her smiling. I grabbed the back of 
her head and pulled her back. I ground my pussy against 
her mouth. I just... I just needed release."

Glen pressed the button again and was reward with an 
almost imperceptible moan of pleasure.

"She licked me again... I remember her tongue feeling so 
good. Each time it rubbed my clit the wave of pleasure 
grew stronger until I came. When Les realized I was 
coming, she sucked on my clit. God, it focused all that 
pleasure into a single part of my body. I realized my 
eyes were shut and I slowly opened them. The woman on 
the monitor blew us a kiss."

That last sentence was said in the sudden quiet of the 
bar as the band had come back onto the stage. Lauren's 
voice wasn't loud, but Glen caught a few glances swivel 
in their direction. Lauren blushed and Glen pushed the 
button. This time she did jump, but tried to cover it by 
signaling to the waitress for another round. Glen's eyes 
swept around the room and the woman across the table 
gave him a little half smile before turning back to her 
date. Glen felt Lauren's leg begin to shake and he 
released the button. He didn't want her to come too 
soon.

The band started to play again, an upbeat jazzy tune. 
Glen leaned back and paid the waitress when she came by 
with the fresh round of drinks. He didn't try and engage 
in conversation with Lauren. Instead, over the next 
hour, he would periodically press the remote, keeping 
the stimulation at random intervals and using her 
nipples as a barometer. And each time, after he pressed 
the button, he moved his other hand, rubbing her thigh 
under the table and almost but not quite under her 
dress.

When the second set finished, he took Lauren by the 
elbow and motioned towards the door. "C'mon. It's time 
to leave." As they stepped outside, he took her arm and 
started walking to his car. "That was a pretty hot story 
about Leslie. But why would she try and blackmail you? 
Didn't you return the favor?"

Lauren looked down and shook her head. "After I came... 
I pretended to be out of it. Eventually Les put a 
blanket over me and went to bed. The next day, I kept 
talking about how drunk I got last night and how I could 
hardly remember anything. Les kept trying to hint and 
corner me about it." Lauren frowned and sadness welled 
up. "I think she may have had a crush on me, but..."

Glen motioned for her to get in the car. As soon as her 
ass hit the seat, he hit the button again and kept it 
pressed. Lauren moaned and shifted on the seat, but 
didn't look at him. He watched this beautiful 22 year-
old woman enveloped in her own pleasure. He reached over 
and pulled a breast out of her dress.

Lauren's eyes flew open. "What..." Glen twisted the 
nipple cruelly. Lauren gasped but pushed her chest 
forward, not away.

"That's what I thought... you like a little pain with 
your pleasure." He kept massage her breast.

"What if someone sees?"

"It's dark and late. Though people might be leaving the 
bar soon." He kept her gaze as he reached over and 
released the other breast. "So you better come soon. 
I'll do my part." He smiled and held up the remote with 
the button still pressed.

He moved back to the first nipple and circled it with 
his finger. He saw Lauren's right hand dip below her 
dress and press the underwear against her. He pulled the 
nipple, watching the elastic, pink skin lengthen out 
before it snapped back. Lauren groaned but in pleasure 
not in pain. Glen looked at the vision before him. 
Lauren's hips gyrated against the seat and her hand 
moved beneath her dress. The other had snuck up and 
played with her breasts. She twirled a nipple in between 
her finger and thumb before pinching it hard with her 
nails. 

Glen eased out his phone and hit the record button. This 
was too hot to miss. He then unzipped and his cock 
sprung up. He began to stroke it when he got a better 
idea. He took Lauren's hand from her breast and brought 
it to his cock. Her hand was warm and firm. She squeezed 
the base before moving up and down the shaft with an 
even rhythm.

Glen let out a soft sigh. Out of the corner of his eye, 
he made sure his camera still had Lauren in the frame. 
Her right hand was still under her dress, pressing the 
panties against her pussy. Glen felt his own pleasure 
building.

And he released the button.

Lauren growled in disappointment and looked over at him. 

"Sorry Lauren, but I realized I just got my car 
detailed. I better not make mess. I am sure you can make 
it so my come doesn't make a mess." He looked 
meaningfully down at his cock and then licked his lips.

Lauren shook her head. "No, I can't... that's too far."

"Yes you can Lauren. Why put off the inevitable? Start 
sucking." He smiled and gave the remote a quick press. 
"Don't worry, I'll still get you off."

She averted her gaze and moved onto her hands and knees. 
She leaned forward, her hair falling across her face. He 
felt her breath on the head of his cock and her 
hesitation seemed to go on forever. Then her mouth 
closed upon his shaft and she immediately started 
sucking up and down. He turned the panties on again and 
was rewarded with a hum of pleasure. Slowly he put his 
seat back more and framed the erotic sight on his 
camera. He watched her head moving up and down his cock, 
her exposed breasts jiggling, and best of all, he saw 
her hand still pressed between her legs. 

Then past her ass, he saw movement outside of the 
passenger window. The couple from the bar was standing 
just outside his car. He felt a momentary pang of fear, 
but then realized that the woman had her hand in the 
guy's pants, stroking him. He smiled at them and then 
reached forward. 

He grabbed a breast and fondled it for a moment, then he 
moved his hand along her hip until he reached the curve 
of her ass. He grabbed her dress, pulling it up and 
giving the couple a perfect view of her butt.

Lauren's tongue twirled around the tip of his cock and 
her hand moved from the base to cup his balls. He felt 
the pleasure building. She firmly squeezed his balls, 
putting him over edge.

"Oh god yes!" He emptied himself into her mouth.

Lauren's right hand was still furiously working between 
her legs, but surprised Glen by staying on her hands and 
knees. "Please." She gasped. "Play my nipple!"

He reached down and grabbed her full breast. His fingers 
found her nipple and he began to pull. She gasped in 
response and began to shake. Over the curve of her ass, 
he saw the woman still stroking the guy as he leered at 
Lauren's naked ass. He twisted his fingers again.

"YES!!" 

Lauren collapsed in a twitching heap. 

The couple mouthed thanks as the guy zipped up.

"Wave to the nice couple Lauren." 

Lauren looked up at Glen confused. He pointed out the 
passenger window. Lauren looked up and gasped, "Oh my 
God!" Her cheeks blushed. The couple had turned back and 
the woman blew Lauren a kiss before they sauntered away.

Lauren's cheeks remained red, but she continued to stare 
after the couple. 

Glenn turned off his phone and stroked Lauren's hair. 
"Let me know when you are ready and I'll drive you over 
to your car." 


Part Three coming soon.... "The Second Hurdle"


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

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
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