8 comments/ 107908 views/ 7 favorites Teaching My Boss a Lesson By: sexymistress6969 Jessica, or Jess to her friends had just graduated from college. She was a wide-eyed optimistic twenty-something determined to change the world. She was not as naïve as everyone thought, even had a little bit of a dark side that she hid very well. She was about 5'6", average build with long dancer's legs, blue eyes and long straight dark hair that was the envy of all of her friends. The only job she could find in the job market when she graduated was a glorified intern on a senator's re-election campaign. She loved the work, canvassing constituents, listening to their concerns, figuring out how to help people, she believed in what she was doing. One night she was out canvassing and got caught in a rainstorm. She ducked into a restaurant to wait out the rain, but after a few hours it became clear that the rain wasn't going to stop. It was getting late and she knew her roommate would be worried about her. Braving the rain she left the restaurant, she was about a block from the restaurant when she realized that she had left her car keys at the office. Frustrated with herself she turned around and headed back to the office. She got back to the office, everyone had already left and all the lights were off. She opened the door and walked back towards her desk, looking down at her white shirt and silently gave thanks that no one was there to see the hot pink bra now almost clearly showing through her button down. She picked her keys up off the desk and as she looked up she saw a light on. Knowing some of the information was sensitive she crept towards the light determined to catch the intruder. She reached the door to the office and looked around it very carefully not sure what she was going to find. Standing with her back to the door, Jess saw shoulder length platinum blonde hair, that gave way to porcelain shoulders, with only black lace straps. A black and red lace dress ended just below the tight ass. Thigh high boots sat below the black and red, and fishnets held in place with red garters peeked out from under the little clothes that she had on. Jess was intrigued by what she saw and leaned further around the door to get a better look at this slut. While she did this she accidentally hit the door, and it creaked. Both Jess and the slut jumped at the noise, and as the slut became aware that there was someone else in the room. She whipped around to face the door as Jess moved out from her hiding place. As she stepped out from behind the door to face the unknown slut in front of me she turns towards me in shock that she has been discovered. Hands moved fruitlessly to cover up the outfit, her face anything and everything. Jess's hand flew to her mouth as she got a full front view of the slut, the front of her skirt flipped up and her cock out erect and throbbing. Confusion flooded Jess's face as the slut stepped forward and she finally saw her face. It was him, her boss the chief of staff. The first word out of his mouth was shit, as Jess tried to pick her jaw up of the ground from this new information, the wheels in her head began to turn and at the same time something in her began to twinge. She felt herself getting wet as she stood there and stared at him. He began to move towards her, tucking himself back in as he crossed the room. As he moved towards her Jess took a step back and fell back into the wall. "Jess please. Wait stop. It's not what you think I swear. I can explain." Jess looked him up and down, straightened herself up and took a step back towards him. "Alright Cameron, explain yourself" "I...I...I had all my clothes taken from me at the office gym...and.and...This was all I could find. I swear...And I...I didn't want to look like a ...you know. A guy in drag...so...So...I wanted to look passable so I could. You know make it home...if I was recognized it would be...bad...for the senator." "I don't believe you, you make too sexy of a slut. You need to tell me the truth Cam. And I don't enjoy being lied to. You need to tell me the truth" Jess began to move towards him her aqua eyes looking him up and down. As she moved towards he began to step back and backed up into the desk. She placed her hand on his chest, felt the false boob under the tight low cut top and pushed him so he was sitting on the desk. She reached her hand under his skirt to touch him. She felt him react and heard him moan softly as her hand found his now neatly tucked away cock. She used her hand for a few minutes the pulled it away and looked him straight in the eyes. "Tell me the truth Cameron" "I don't know what you want to hear Jess...I...I did tell you the truth ...I...I just wanted to protect the senator. I...I wanted to look realistic so I could make it home...I...I swear. His hand slipped to the keyboard and a webpage pops up...it's a MySpace account for tiffany slave...and another for fictionmania... "Please Jessica. Please help me get home safe... please can't you drive me home... I will do whatever you ask if you help me save our boss...I mean that IS why I am doing this. I SWEAR." Jess looked at him again, she still didn't believe him but she was going to play along for a little bit see how much he could take. "Alright Cameron if you say that is what you are doing then I believe you. Now where was I?" Cameron looked at her as if he wasn't sure he could trust her but after a second decided that he could. Still sitting on the desk Jess standing between his fishnet clad legs, Cameron reached up and placed his hand behind her head his thumb brushing against her cheek. Her hands went around his neck as they leaned in to kiss. Cameron's other hand reached to take one of her hands from around his neck he placed it back on his tucked cock. Jess began to rub through the silky red thong, working her way under the material to take a hold of the erection. Moving her hand up and down and in small circles she brought him almost to the edge of his orgasm. He managed to gasp out the words "I'm so close" and as soon as he did Jess removed her hand. "You wanted a ride home didn't you? Let's go, I have to get home." Jess stepped away from him and adjusted her hair and the clothes that had had been pushed out of place in the moment. Cameron still sat on the desk unable to move as Jess walked away. She walked out of the office door, paused and leaned her head back in. " Are you coming or not?" "Yea yea I am" Cameron jumped off the desk and went around to close down his computer. His MySpace page was still up on the screen, split screen with fictionmania. He closed down the computer and looked up towards the door. Jess was standing there, still wet from being caught in the rain watching him. "Hurry up boss I have to get home. My roommate is waiting up for me I'm sure she is worried about me being this late" He closed down the laptop and placed it in the case. He slung it and his purse with his wallet and keys in it over his shoulder. His heart was pounding, so nervous to being caught and thinking that he may have pulled one over on the silly wide eyed girl that he forgot that it is odd that he has a purse and worse that he walked effortlessly in the 5 inch heels towards you...his hips and ass swaying slightly as he played up the tarty outfit he had on.. Cameron struts out the door and out through the office walking next to Jess. They get to the elevator and as they stand there waiting for it to rise to them Cameron looks over at Jess overly confident that his secret is still safe, she feels him watching her and smiles to herself. As the elevator doors open and they step inside they make eye contact. When the door closes Jess found herself up against the door Cameron's hands on either side of her as he kisses her. His lips move to her neck and his hands stray down and begin to hike up her skirt. His hand drifts up her thigh and just before it can reach its destination Jess breaks the kiss and grabs his hand. "No not yet, wait please. I'm not ready" He takes his hand away and leans away from her as the elevator doors open. "Alright alright, I'm stopping. Just a ride home then" They walked out of the elevator Cameron taking the lead, Jess followed behind him watching as his hips swayed a little to confidently and comfortably in the sky high heels that he had on. Her eyes strayed to his ass and admired the tightness and the way it moved. She had always been a sucker for a good ass. They got to the car, but Jess didn't unlock the door. The rain had slowed to just a drizzle now, Cameron went to the passengers side door and tried to open door. It was still locked. He looked up at Jess, "Are you going to open the door?" She looked back at him and walked towards him. "Maybe. I noticed you were checking out my skirt, I would have thought you would want me to get even wetter. Plus you were checking me out I think I am entitled to check you out in this sexy little outfit" She moved towards Cameron standing in front of him, as she leaned in slowly to kiss him. She placed her on either side of him on the car. He deepened the kiss, trying to take control of the situation. He tried to slide up a hand up her skirt again and she smacked his hand away. He pulled away to look at her. "If you are going to let me touch you, then maybe you should just touch me" She stood back from him and crossed her arms looking him straight in the eye. "You are dressed as the slut so you get to be the slut tonight. I am not the slut, and I will not be manipulated by an older man who thinks he has pulled one over on this 'naive' little girl. If you are going to dress the part I'm going to treat you like the slut I know you are. You are going to come home with me Tiffany and I will show you what it really means to be my little slut" She unlocked the door, opened it and blocked Cameron's way to escape by standing in front of the door. He looked at her trying to judge if she was bluffing or not. Seeing no way out of this he climbed into the car. Jess closed the door behind him, smiled to herself and walked around the car to climb into the driver's seat. She closed the door then locked the doors. She turned to look at Cameron, "Go ahead I know you want to ask me." He lifted his eyes from his lap to look at her. "You know the truth? How did you figure it out?" "You know how to walk in heels far too well, and your wardrobe is too well designed for this to be an accident. Plus I saw the MySpace page." Jess put the car in drive and pulled out of her parking space. "You do make one sexy woman though I will give you that." Cameron smiled at her, feeling a little more confident that even though she knew the truth she would keep his secret. "Thank you Jess," Jess cut him off. "You will refer to me as Mistress, slut. You will do exactly as I say, or you will be punished. You are my little slut now and I will treat you however I want to. And before you protest our new agreement, remember that I know your secret and can let that fun little tidbit of information slip anytime I want if you do not please me. Are we clear slut?" Cameron looked at her and his jaw dropped. Part of him thought she was bluffing, but there was something about what she was saying, what she was threatening him with had him getting very hard underneath his short skirt. He tried to gauge how committed to this she was. The car stopped at a red light and Jess turned to look at him. "I said are we clear slut?" She wasn't bluffing. The question was stern, rough and to the point. Cameron's cock tucked tight into his red thong and garter belt snapped to attention, he had never been so turned on. His eyes dropped back to his lap in submission. "Yes Mistress, very clear." "Then we have an agreement Tiffany. Are you going to be a good girl and please your mistress? Or is mistress going to have to punish you?" "Whatever you say Mistress, anything to please you. I live to please you Mistress." Cameron was so turned on, he was so hard, he couldn't help but reach down to touch his throbbing cock, trying to relieve some of the incredible pressure. "Good girl." Jess turned her head to look at her newly willing slave and noticed him touching himself. "Did I say you could touch yourself slut? Remove your hand; you will learn how to wait until your mistress is ready for you." And with that she reached over took his hand away from his rock hard tucked cock and in one swift movement captured his wrists tightly. "Yes Mistress, I am sorry. I live only to please you Mistress. Please forgive me." Jess turned back to the road, hit the gas and smiled. This was going to be fun. Teaching My Boss a Lesson Ch. 02 (note this is the second chapter to a previous story) * Jess pulled the car into the parking lot of her apartment building, flipped it into park and turned the car off. She turned to look at the slut sitting next to her. "Alright slut, time to face the music. We are going upstairs but Mistress needs to make sure everything is in place for her slut." Jess reached over and uncuffed her slut from the door. Got out of the car and walked around to the passenger's side door, she opened the door and Tiffany slowly got out of the car straightening the little bit of clothing she had on her body. "Yes Mistress, anything you wish." Jess took Tiffany by the hand and led her into the building. Tiffany followed her new mistress eagerly but looked around nervously as they walked into the front lobby. The doorman gave the couple a look as they passed and Tiffany hesitated. "Slut, don't dilly dally. Move!" Tiffany jumped to obey her mistress, her clitty twitching with the degradation of being called a slut in front of a complete stranger. They reached the elevator and Jess turned to her slave. "You will wait here until Mistress sends someone to get you." A look of fear flashed across the slut's face as her mistress again pulled out the handcuffs. Jess took her slut's wrists and cuffed her to a railing on the wall. "You are not to talk to anyone, slut. You are mine and only mine unless I decide to share you with someone. Mistress will send someone to get you when she is ready for you; you are not to speak to them either. Understand slut?" "Yes, Mistress, whatever you wish Mistress." Tiffany lowered her eyes in submission as her mistress walked into the open elevator leaving her handcuffed to the railing. Tiffany began to lose track of the amount of time she stood there waiting for her mistress to come and get her. To her good fortune no one had walked past to see her in her utter humiliation. Tiffany thought she was in the clear that no one would see her when two frat boys walked around the corner to get on the elevator. They both looked her up and down clearly checking out the long shapely legs covered up past the knees in leather boots and the tight red and black lace trimmed outfit. One moved towards her. "Hey baby, how'd a sexy little thing like you get all tied up here like this?" As he walked towards her Tiffany kept her head down and tried to remember that her mistress had told her she was not allowed to talk to anyone. The frat boy walked closer to her and reached out to graze his fingers up her bare arm. "What can't you talk to me? Come on baby at least tell me your name. Come on you sexy little thing. All dressed up like this and you won't even talk to me? I'm David, come on baby what's your name?" David's hand drifted down Tiffany's back and he took a firm handful of her tight ass. Just as his hand grabbed her ass the elevator bell dinged and the door opened. Tiffany looked up quickly hoping she was saved. If this David kept up touching her he was going to find out very quickly her secret. The utter humiliation of being handcuffed and not allowed to talk while dressed as a complete slut was taking Tiffany so close to the edge she was unsure how long she would be able to hold off blowing her load. As the elevator doors opened Tiffany saw a leggy blonde step out. She looked about 22 short curly blonde hair and piercing blue eyes. She was wearing a black trench coat and knee high black leather stiletto boots. She approached Tiffany and David. "Hands off gentleman, she is all mine." The blonde reached over and unlocked the handcuff from the rail. She took the empty cuff, flipped Tiffany around, cuffed her hands together behind her back, and pushed her towards the waiting elevator. Just before the doors began to close the blonde winked at the frat boys, "maybe next time boys, sorry." She winked and gave a little wave as the doors closed on the boys, whose jaws were on the floor. Once they were alone in the elevator the blonde turned to Tiffany. "Your mistress is waiting for you upstairs. I will take you to her. You will serve us both tonight, you will call me Lady. You will do what we say or you will be punished. My orders will not contradict your mistress's but you will listen to her over me. If you understand nod your head slut." Tiffany looked up at her second mistress and in utter submission simply nodded her head as the elevator came to a stop and the doors opened before them. Lady walked out of the elevator, her slut following close behind, they reached the door of the apartment and as Lady opened the door Tiffany took a deep breath and stepped into her mistress's apartment. The lights were turned down low all Tiffany could see were basic outlines in the shadows, as her eyes adjusted she saw her mistress standing in the center of the room. She was wearing a tight black leather corset with a short pleated black leather skirt. Garters peeked out from underneath what existed of the skirt attached to black thigh high stockings. The outfit was completed with knee high black leather boots and a riding crop in her hand. Tiffany was so floored by the beauty of her mistress that she stopped moving across the room. "Go kneel before your mistress slut." A voice made her senses click back on; Tiffany looked to her right and saw that Lady had taken off her trench coat to reveal a matching outfit to the woman standing across the room. Tiffany's clitty had never been so hard she was completely under the control of these two beautiful women and she wanted nothing more. She slowly walked across the room towards her mistress who was tapping her riding crop against her hand impatiently waiting for her little slave to approach her. Tiffany reached her mistress and dropped to the ground in front of her, on her knees her hands still cuffed behind her back. "There's my pretty little slut. Were you a good girl downstairs when mistress was getting ready for you?" "Yes Mistress, of course Mistress. I only do what Mistress says." Tiffany looked up at her mistress. "She lies to her mistress, she is nothing but a dirty little slut willing to put out for anyone who offers up their cock." Lady put in her two cents from behind the kneeling slut. "You lied to your mistress slut? Mistress is not pleased." She reached out and snapped the riding crop against her slut's thigh just above her boots. Tiffany twitched with the pain. "No Mistress I did not lie to you. I did everything you asked of me. I did not say a word to those boys, they touched me, there was nothing I could I do. I did what you asked of me Mistress. I would never disobey you I live to serve and only you Mistress." "They touched you? You are my slave no one touches you without my permission." She snapped the riding crop against Tiffany again, and her slave twitched with pain again. "I am sorry Mistress, I am a bad girl, and I deserve the punishment you are giving me. What can I do to apologize to you Mistress? Tell me how to please you Mistress." "Come closer slut. Lady, uncuff her." Tiffany moved closer to her mistress and Lady leaned forward to uncuff their captive, her perky breasts brushing against Tiffany's back as she did. Once Tiffany's hands were free she reached forward to touch her Mistress's boots. "Do not touch me slut unless I tell you to." Mistress snapped the riding crop and Tiffany flinched again. "Yes Mistress, I am sorry Mistress." Tiffany's hand went to her sides. "Use your tongue slut, pleasure your mistress, you will not use your hands, just your mouth." Tiffany moved forward as her mistress lifted the front of her skirt. A black garter belt came into view but nothing else covered her shaved cunt. Mistress spread her legs slightly to give her slut better access, and Tiffany took a breath before she moved to pleasure her mistress. Her tongue moved in separating the lips of her Mistress, easily finding her clit. She wiggled her tongue slowly vibrating her Mistress's clit as let out a slight moan. Tiffany leaned in slightly to suck on her mistress's clit causing her mistress reach out and grab a hold of the chair nearest to her. Tiffany turned her attention to the rest of her Mistress swirling her tongue in and out of the folds, around the very edge of her vagina before plunging in. Soft moans from above her let Tiffany know that she was pleasing her Mistress. She moved back to pay attention to her Mistress's clit again, hoping that her Mistress would climax and reward her little slut. The moans from her mistress were making Tiffany's clitty so hard she was having a hard time not touching herself. Hoping that her mistress would not notice Tiffany reached under her skirt to rub herself. Just as her hand reached her now rock hard clitty she felt the sting of the riding crop on her back. Shocked by the sting she stopped paying attention to what she was doing and turned around to see where the sting came from. Lady was standing over her riding crop in hand. "You are pleasing your mistress not yourself slut. Remove your hands now." "Who said you could stop slut?" Mistress had now regained some composure and the flush in her cheeks was not just pleasure. "Mistress he was touching himself, and I know you want all of his attention on you." Lady snapped the crop against her hand to make her point. "I'm sorry Mistress, I couldn't help myself I am sorry. Please Mistress I am a bad girl." Tiffany looked up at her mistress. "Yes you are a bad girl. You have lost the privilege to please your Mistress. Get up slut." "Yes Mistress." Tiffany scrambled to her feet. "Go stand over there." Mistress waved her hand in the general direction of the other side of the room. Tiffany scrambled to obey her mistress. "See that banister slut? Go pose for me; show me what kind of slut you are." Tiffany turned to look at her mistress. "Mistress?" "Lady will be your photographer. Go pose for us. Please us and you will be rewarded." Tiffany moved towards the banister that lead to loft above the living room. She reached a hand out tentatively to grab a hold of the banister. A little unsure of what to do she leaned into the railing sticking out her tight little ass so that straps of her garter belt pulled even tighter. Lady snapped a picture. Tiffany looked to her mistress for approval. Her mistress's hand sliding down her body and under her skirt was enough inspiration for Tiffany, knowing she was pleasing her mistress she began to get more daring. Using the banister like she was a stripper, Tiffany moved up and down the pole grinding against it as Lady snapped picture after picture. The idea that someone was documenting this was making Tiffany very hard in her silky panties, her precum oozing out staining her panties. "Please Mistress, let me please you. Please let me cum, please Mistress." Tiffany turned to her mistress and dropped to her knees. "I think maybe we should let the little slut do what she wants." Lady turned around to face Mistress, "but only if I can document that too." "Come here slut," Tiffany crawled towards her mistress. "You may use your hands or your mouth to please me." Tiffany leaned forward to take her mistress into her mouth sucking on her clit. As her mistress moaned her pleasure Tiffany reached as hand up her mistress's thigh and towards her cunt. She played around the edge before pushing one finger into her mistress. Her mistress's head fell backwards in pleasure and Lady snapped a picture just as the finger disappeared into Mistress. She moved her finger in and out of her mistress as she continued to play with her mistress's clit with her mouth and tongue. Tiffany could feel her mistress tighten around her finger and she knew she was getting close to her orgasm. Tiffany kept pushing and playing with her mistress until she was able to push her mistress over the edge. She felt her mistress tight around her as she moaned out her last pleasure; Tiffany's fingers were wet with her mistress's juices as she slid her fingers out of her mistress. Mistress took the hand and moved it towards her slut's mouth; Tiffany eagerly sucked her mistress's juices off of her fingers. Mistress pulled her to her feet. "You did well slut, Mistress is pleased. Go sit on the couch." Tiffany moved towards the couch and sat down tentatively. "Please Mistress Let me cum, please Mistress. I will do anything, please Mistress let me finish." "She has been a very good girl Mistress; maybe we should let her get off. Or we should watch her get herself off." "I think that is a very good idea Lady. Alright slut you may get yourself off. Lady, take more pictures. Oh and slut, make sure you put on a good show, you are going to post these on your very sexy MySpace that I saw earlier." Tiffany was so hard she had never been so relieved to touch herself. She began to rub her rock hard clitty; she knew it wasn't going to take very long for her to blow her load. She kept rubbing and rubbing feeling herself getting closer and closer to the edge. She looked up at her mistress and with one slight nod from her mistress Tiffany pushed herself over the edge her hot sticky cum exploding all over her silky panties. Mistress walked over towards her slut. She bent down to kiss her gently. "You are such a good girl." "Thank You Mistress" Both paused and looked at each other a moment passing between Jess and Cameron before they both snapped back into the moment. "Now get up, its time to post these sexy sexy pictures." Tiffany got up off the couch and moved towards the computer. "Yes Mistress anything you say Mistress." Tiffany logged into her MySpace and began to upload the pictures while her mistress looked over her shoulder.