Webcam Blackmail Ch 02

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 9pm.

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 hun. 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, dark bar. A jazz band played on a stage opposite the door with intensity that filled the room. 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's 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 on 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 with 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"

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