8 comments/ 17259 views/ 24 favorites Webcam Blackmail Ch. 02 By: illicit_writer Glen looked over his email before sending it out. It was essential that he get the wording just right so that his sister 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" Let me know what you think! Webcam Blackmail Ch. 03 As Glen pulled into his driveway, he saw his sister'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." The next day, as Glen typed up the email, a smile slid across his face. 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 wifi 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. 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. He saw that one of the voyeurs had activated his own cam and 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 - 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 put his cock back in his pants. He 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 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 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. Webcam Blackmail Ch. 03 "Fuck her!" "Yeah, fuck her!" Glen leand looked 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 one motion. He was fucking his sister! 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. He quickly wrote on a scrap paper he found on her desk. "What are you doing?" Lauren asked though her voice was faint. "I paid a year subscription for that site. As I said the user name is HotnHorny22 and the password is Slutlauren. I thought I'd write it down for you." He looked and caught her hand wandering back down between her legs. She snapped it back when she him watching. Glen just smiled. "You can keep the mask." Let me know what you think! Webcam Blackmail Ch. 04 THURSDAY NIGHT Lauren, Ready for you last hurdle? One more and you will get access to my netbook and will be able to delete any and all files. On Friday night, you will go to the Emerson Hotel on Michigan Avenue at 11:30 pm. You will come to room 3041. Requirements for this night are: 1. Your pussy must still be shaved 2. You will wear the lingerie you had on for our last meeting. It's time you returned the favor from your lesbian college experience. Be ready. Happy times! Glen sent out the email with a mixture of satisfaction and regret. It had been a fun two weeks with his hot, 22 year-old sister doing his bidding. He had felt he had needed to keep the hurdles within days of each other to keep her off balance. Lauren's email came an hour later. I can't see Leslie agreeing to this, but I will be there at 11:30. You better keep your own promise. Glen felt a stirring in his crotch at her immediate acceptance and began to plan for Friday. He wanted the night to be perfect and it would take a bit of planning. FRIDAY NIGHT Nervously Glen paced the living room of the hotel suite. He glanced out the window and looked at the Chicago night time skyline. Would this actually work? He glanced at his watch. 11:35. He looked towards the closed bedroom door. How long to wait? Where was Lauren He was just about head back into the bedroom when he heard a soft knock on the door. Finally! He peeked through the peephole and there was Lauren, glancing nervously from side to side. He opened the door and ushered her in. She had on a tight, silver dress. It went up to her neck, but showed off her curves and body to great effect. Shame it had to come off. "Sorry I-" Glen placed an index finger over her lips. "Shhhhh... no talking." Lauren gave him a quizzical look but quickly nodded. He took arms and raised them over her head. He then grabbed the hem of her dressed and yanked it off of her. She began to protest but then remembered his edict and merely ducked her head to help Glen get it off of her. As she stepped back, out of the dress, Glen took a moment to take in his beautiful sister. Her brunette hair was slightly messed but that only added to the effect. She was dressed in the black lingerie from the second hurdle. The top wrapped around her neck, collar-like, before cascading over each breast. The matching panties were see through and he was pleased to see her pussy was free of any hair. Her well shaped legs were sheathed in black thigh highs. Unlike the previous time, she did not hunch or try and to hide herself. Instead she merely stood there, gaze averted to the ground, but shoulders back and almost confident. He grabbed her hand and led her towards the bedroom door. "Remember, no talking." Glen waited for her nod of assent. He kept a hand on the small of her back and opened the door. Lauren gasped and would have stepped back if Glen hadn't kept her in place. Sprawled on the bed was a blonde woman dressed in matching lingerie but in red. She was tied to the headboard and blindfolded. But none of this is what caused Lauren's reaction. On the bed was Glen's wife, Kim, Lauren's older sister. 48 HOURS BEFORE "I made reservations at the steak house at 7:30 hun." Kim came up and put her arms around her husband's waist. "I was thinking of maybe getting a room at a hotel and making a night of it. What do you think?" Kim smiled. "That sounds nice... Anything else? I can't think of anything to get you for your birthday. You have your Wii and blue ray. My sister has been no help. She's barely been returning my calls. My dad says cigars but I know you don't really like them." "Well..." "Are you blushing?" Kim playfully poked him. "What naughty things are you thinking of?" "I don't want to piss you off..." Glen felt his pulse race. "Hun, you know I feel guilty about neglecting you lately." She gave his chin a quick peck. "Work will calm down soon enough. But let's use this opportunity for me to make it up to you." "I'd love to see you..." Glen barely thought it possible but decided the worst she could say is no. "I'd love to see you with a woman." Kim looked at him open mouthed. She took a step back and shook her head. "I'm sorry but that just doesn't turn me on. I'm 100% hetero." Glen had thought she might say that and gave her his best argument. "Remember when I blindfolded you?" At her nod, he continued on. "It turned you on so much. I've never seen you cum so hard. I thought, maybe put you in the same situation and have the woman go down on you." Kim shook her head. "You are going to find a woman who will go down on me? With no payback from me?" She laughed. "You really think you will find a woman to do that?" She laughed again, gave Glen another peck, and started to walk back to the kitchen. She looked back at her husband and her expression softened. "I think you'll come up empty, but if you do find a woman, I'll let her go down on me." She turned the corner and then peeked back. "You better get me drunk." FRIDAY NIGHT Lauren was shaking her head, still pressing back against Glen's hand. "You find me a woman?" Kim called out, a drunken smile spreading out across her face. She opened her legs wider, clearly showing that between her two lace clad thighs there was no panties and only neatly trimmed brown bush. Glen leaned into Lauren's ear. "This is the last hurdle... after this you are free." "I thought - " His sister began to whisper but then shot a frightened look towards her older sister. Silently she mouthed, "I can't." Glen nodded and pointed at the drunk, sprawled sister. A look of agony crossed Lauren's face and tears began to well up. Glen took her over to his netbook. He had the video of her dancing naked in a split screen with her face clearly shown. Then he pulled up his email account and pointed to the addresses. Lauren saw her parents' email, her uncles and aunts addresses, even her co-workers. She froze. Taking advantage of Lauren's hesitation, Glen walked her toward the bed. "I can hear you..." Kim giggled, her breasts jiggling just under the red silk. "I am ready for your 'woman.'" Glen ushered Lauren onto the bed and took a step back. His sister, on all fours, just in front of his wife's lewd display. "I feel you on the bed!" Kim closed her legs and a big pout sprouted on her lips. "What's taking so long?" Lauren looked over at Glen with a silent plea. He shook his head and pointed. She turned back and grabbed her sister's knees. She tried to pry them apart, but now Kim was putting up a mock battle. She kept her legs shut as Lauren pulled harder. Suddenly, Kim gave away and the force of Lauren's effort nearly caused her to fall back. But she clutched at Kim's thighs. Slowly, she began to kiss down her sister's thigh, almost as if she was giving Kim time to pull away. Instead, Kim thrust her hips forward. Lauren hovered just over her sister's pussy and then tentatively put her tongue out. "I feel your tongue..." Kim giggled and thrust her hips up again mashing her pussy against Lauren's face. Glen watched as his sister didn't pull away but let the motion guide her tongue into the gash. He moved over to get a better view. He couldn't believe the sight! The 22 year-old moved back up the other thigh. Kim cooed and then said, "Why don't you kiss me Glen? Kiss me while your 'woman' licks my pussy." Glen walked around to the front of the bed. He saw Lauren tracking his progress as she continued to kiss around her older sister's pussy. Glen leaned over and kissed his wife. She stiffened in surprise! "What?" For a moment, Kim strained against the rope binding her wrists. "I thought this was just going to be you pretending!" Glen chuckled. "No, there's a woman between your legs right now." He reached over and grabbed the back of Lauren's head. He pushed her face into his wife's crotch. "She must love pussy if she'll lick me without anything in return." Glen was pleased to hear Kim's voice soften to the idea. She no longer struggled against the rope, instead a flush began to warm her face. Glen saw his wife grinding her hips up against her sister's face. He saw a flash of a tongue and knew that Lauren was truly licking her sister. Glen gave his wife a passionate kiss, he felt his own cock responding. Finally he broke the kiss. He wanted to see this. His wife seemed disappointed when he backed away, but then gasped slightly from Lauren's ministrations. All hesitation from Lauren's actions were gone as now she moved with purpose. Her tongue kept a steady rhythm upon Kim's clit and the younger sister was moving a finger in and out as well. Clearly she had decided that making her sister cum was the fastest way for her to get out of this situation. Gene saw his wife's nipples begin to harden and knew that she would cum soon. Lauren continued her licking, meeting his wife's hips as she ground against her lips. Glen move around behind Lauren, her fine ass wiggled in the air from her effort. He began to slip off her panties causing Lauren to turn around in confusion. She shook her head, but Glen merely arched an eyebrow and glanced at his netbook. Meekly, Lauren lifted each leg to let him take off her panties. Kim assumed the woman was teasing her as her building orgasm began to subside. She groaned in frustration. "Please! Your tongue feels so good!" Lauren realized her sister's body had lost the momentum towards climax and resumed moving her finger in and out of her sister. With one last glance at Glen, she moved back down to continue her licking, her ass sticking out in the air. He began to caress her ass, torn. He knew he couldn't fuck her as his wife would definitely feel that. His fingers moved to Lauren's shaved pussy. It was wet! He dipped a finger in easily, her passage hot, wet, and tight. Just over her ass, Glen could see his wife starting to move her head back forth and she began to moan. Normally his wife was very quiet during sex, but this whole scenario had clearly gone to Kim's core. She aggressively gyrated her hips to meet Lauren's every lick. Glen continued to caress Lauren, not really trying to get her off, merely reveling in the knowledge that Lauren was getting turned on eating out her sister. "Oh hun!" Kim gasped. "I'm going to cum soon!" Lauren's head increased her tempo. "Come hold my hand hun! Quick!" Glen moved around to the top of the bed and grasped one of Kim's hands. He kissed her and she returned it with animalistic desire. He thought her teeth drew blood as she latched onto his bottom lip and groaned again. "Yes..." "Yes!" "YES" Kim's hips pitched against Lauren's face and her whole body froze and then shivered. Slowly her hips moved back to the bed, leaving the younger sister's face glistening with her juices. Lauren watched her sister's blindfolded face try to slow her own breathing. Lauren moved back down and kissed her sister's pussy... her belly button... her ribs... she kissed each of Kim's nipples before moving back off the bed and stood up. Kim's body was limp and she whispered, "Thank you." Glen moved back to his netbook and Lauren was quick to follow. He closed out of the email program and began to shut it down. As they waited for the computer to turn off, Kim called out, "Glen?" He turned, smiling at his wife absolutely stunning tied up and flushed from pleasure. "Yes Kim?" "I want to thank the woman who went down on me. She was soooo good." Glen and Lauren exchanged looks of alarm and he stuttered to think of an excuse. But Kim had other ideas. "If she doesn't mind an amateur, I'd like to lick her in return." Glen's jaw dropped. He turned back to Lauren surprised to see a radiant smile spread across her face. When she saw him looking, she tried to downplay it, but Glen grabbed her hand and led her back to the bed. Lauren stepped up onto the bed so she was standing over her sister. For a long moment, she stood there staring at Kim. Glen was almost worried that she was going to confess right there. But instead took a couple steps until there was a stockinged feet on either side of Kim's face. Then she slowly lowered her pussy onto Kim's willing mouth. She was considerate of her sister and kept the weight on her own knees. Glen could see his wife's tongue slowly penetrate her sister's pussy. It trailed along one lip of the opening then down the other. She turned her head as far as Lauren's thighs allowed. "She's wearing stockings too? I can feel them against my cheek..." Her commentary ended as she kissed her way up one thigh, playfully stopping before she hit Lauren's labia and then down the other leg. She snaked out her tongue into her sister's pussy, licking her slit, gauging the taste and then again stopped. This time her mouth moved forward. "Is her pussy shaved hun?" "Yes Kim." "She really is a hot slut. I can feel her heat from pussy." Kim gave a few more licks. "Fuck me while I eat her out Glen. I am so horny, I need you inside of me." No sooner had the words left her mouth and Glen had dropped his pants and angled her body so he could remain standing against the side of the bed. He then grabbed her legs, lined up his cock, and sank into her dripping wet hole. Kim moaned sending delightful shivers of pleasure up Lauren's body. The younger sister let more of her weight fall against her sister's mouth and her hips began to buck back and forth. Glen saw Lauren biting her lower lip in an effort to keep quiet. He knew how vocal she usually was and saw her fight the moans welling up within her chest. Her eyes locked on to the spectacle of Glen fucking Kim. He thrust deeper and faster, spurred on by the taboo audience. It felt so good to be in his wife, the months of excuses washed away in the sublime moment. Lauren had put her hands on Kim's breasts now, playing gently with her nipples. Glen reach forward and sharply tweaked Lauren's left nipple. She did gasp then breaking through her silence, but she did not pull away. Instead she arched her back bring her chest closer to him. He continued his long strokes in and out of his wife. He grabbed on to her right nipple towards him. It stretched out painfully and she ground her crotch rougher against her sister's tongue. Glen looked down and saw Kim valiantly trying to keep up, but she didn't have use of her hands and could only continue to move her tongue against Lauren's clit. Suddenly, Glen saw her flick her tongue side to side rapidly. The effect on Lauren was electric. She squeezed Kim's head between her legs and her body began to shiver, reveling in the new sensations. Glen saw her mouth open and knew she was about to scream. Quickly he grabbed both nipples and viciously pulled her towards him. He covered her mouth with his and kissed. He felt her whole body tremble and knew that an orgasm rocked her body. Her moans were muted by their kiss and their tongues intertwined. Glen realized that for all their activities the past two weeks, they had never before kissed. He felt a warmth engulf his cock a half second before Kim's pussy clenched around him. Lauren's orgasm had triggered her sister's. Glen released Lauren so he could focus completely on plunging in and out of his wife. His own orgasm built. He watched Lauren, spent, still straddling Kim's face. Glen came in an eruption of pleasure. "Oh Kim!" He kept still feeling himself spurt within her, reveling in the sensations that would all too soon slip away. Lauren carefully moved off Kim's face and made sure the blindfolded was still securely over her eyes. She tenderly touched a finger to her older sister's lips and then she got off the bed and looked for her underwear. Glen disengaged himself from his wife and went over to his netbook. He made sure it was shut down and turned to his sister. He motioned to the other room and she nodded. He then went over to his wife and whispered, "I'll be right back." He stepped into the living room and saw Lauren already had her dress back on. He handed her the netbook. "Just get it back to me by next week please. I do have other stuff on it." Lauren took the computer and gave him a long look. "This better be the only files Glen." Glen smiled reassuringly and walked her to the door. There was an awkward moment as they faced each other. Finally, Lauren gave a sheepish grin and gave her brother and blackmailer a quick hug. He watched her walk down the hall, still admiring her ass moving beneath that tight, silver dress. He closed the door and went back into the bedroom. "Hey hun... you going to untie me?" Kim lifted up her bound wrists. "Not just yet..." Glen went to where his briefcase sat on the desk. He flipped it open and made sure that the hidden camera was still recording. The hard drive still had another hour of memory. The hard drive that held the five movies of Lauren. It was a risk to keep them, but he couldn't resist having this material at hand. Blackmailing Lauren was over, but he wanted to be able to jack off to them for years to come. He repositioned the camera a bit. "I still want to play with you my sweet..." He moved back onto the bed and kissed his wife deeply as he began playing with her nipples. Kim purred and pushed her chest up to meet his touch. "You are a naughty, naughty boy." Kim laughed. "I hope you enjoyed your birthday!" The End