3 comments/ 61561 views/ 9 favorites Modern Day Sentimental Education By: djm298 The cars began to arrive, one by one, in the horseshoe shaped driveway. Exiting from BMW, Mercedes, and Lexus sedans in the crisp January air, the middle-age couples walked to the house. Chris recognized them all. Most had known him since he was a little boy. His parents had been socializing with the same crowd for years. He rarely paid much attention to these people when growing up, their conversations forming a background drone to his life at home. Things had changed, though, since starting college. With the physical distance and new, challenging environment he began to view the people of his life through a more critical lens. He was sure his parents noticed the change. Most certainly it was evident in his reluctance to pour Mimosas and Bloody Marys for the annual New Year's Day brunch. It would be an endurance contest as these people he could not relate to talked too loudly -the women about tennis, bridge, and kids, the men about politics and the market and all with that annoying, self-satisfied bent of the upper middle class. He just wanted to get in the car and go somewhere else, read a book, write in his journal - get away. He left the bathroom window from where he had been eyeing the arrival of the guests and made a beeline for the kitchen. A short jog from the side door and, just beyond, freedom. His mother, with Champagne glass in hand, intercepted him. "Oh Chris, there you are. Would you take everyone's coats when they arrive and put them in the hall closets?" Chris thought to himself, what if I just said no. What would she say? "Sure, no problem." "Great, thanks sweetie." The doorbell rang. Four couples entered. "Chris, you are home for the holidays! Oh, how wonderful. Look at you. Oh my god! You are so grown-up." "Hi Mrs. Richman. Nice to see you." Grabbing her fur coat, Chris made the polite smile. The husbands would approach and make perfunctory remarks about freshman year in college, or something that would recognize his presence. The volume of the voices grew as people fought to be heard. Chris noticed how the clothes everyone wore, particularly the women, were no doubt expensive and stylish, yet looked so style-less. It was just the least sexy environment and made him wonder to what he had to look forward as he grew older. Does anyone here still get turned on by his or her spouse, he wondered. Finally, he took refuge in the kitchen. Sneaking himself a drink from the Bloody Mary pitcher, he heard a voice from behind. "Testing the beverages for safety, I assume?" Chris coughed. He flashed an embarrassed grin as he looked at Mrs. Corman. One of his parents younger friends, or so it seemed, for she, to the exception of the group, always looked amazing. He was always a bit shy around her since she been the subject of some of his earliest masturbatory fantasies. There was this style about her and something else he couldn't quite put his finger on. She seemed sexier, even when other peers attempted do dress just the same. He had heard his parents talking about her over the weekend, for she was recently separated from her husband, a successful dental surgeon. "Oh, um, yeah, well I was just..." She laughed softly. "Don't worry. I won't tell, but I hear you are the man for the coats." "Oh yeah that's me. Let me help you." Chris reached over and helped her remove her long wool coat from her shoulders. As he leaned he caught the scent of her perfume. Not doused on her like his mother's other friends. He felt a desire to linger. It was when the coat came off that he really had to suppress his urge to stare. She was wearing a knee length, tan suede skirt that hugged her lovely hips, a black turtleneck sweater, and pair of black leather knee high boots. They had such long, pointy toes with very tall heels. The black leather hugged her slim calves. He turned away, fussing with the coat on his arm so not to seem overly intrigued. His pulse quickened. "Thank you. You don't have to put the coat away, really - just point the way." "No, no, um, it would be my pleasure." Chris went down the hallway to hang up the coat with the others. He leaned close to it as he placed it on the hanger to catch its scent. Perfume, plus the subtle scent of cigarette smoke. Did Mrs. Corman smoke? If so, he had never seen her do so and so few of his parents, if any, still smoked. Yet, it was clear that she was changing, or showing, a new side to herself from the way she looked. When he returned to the kitchen, she was standing with elbow cocked, fluted champagne glass held in her graceful, long nailed hand. Smiling at him. Lipstick on the rim of the glass. He was surprised, for he expected her to join the others in the living room where he would seem no more than the butler. "Hope you don't mind if I helped myself. I just love mimosas." "Oh no, what am I going to do now? That was one of my few jobs." "Ha, ha. Well, I'm sure you are capable of more interesting tasks." He blushed, and looked down. "So, tell me about college? How are classes? Or, are you discovering more important things?" Chris blushed, again. "Nah, I mean, I'm studying most of the time. My roommates a big partier and I've seen what it is doing to his grades." She reached out and touched his arm. "Hope you don't mind me saying, but you always seemed so shy. I was that way when I first started college, but then I learned to just have fun. Let go." Chris stared at Mrs. Corman. "Mrs. Corman, don't let my parents hear that. They pay the bills, I'm thinking all they want to see is production - like grades." "Oh, don't worry. I know how your mother is, but I'm sure she would be happy to see you with a girlfriend. My god, your face is filling out - you are really getting quite handsome." Chris turned crimson. "Oh, I'm sorry Chris. I didn't mean to embarrass you." "No, no. Not at all. I mean, um, it's okay." Her eyes followed his as he said this. "Okay, then." She reached over to grab an orange wedge, when her drink tipped. Chris watched as the mimosa spilled onto her gleaming, black boots. "Oh, damn! I'm so clumsy." Without thinking, Chris started for a napkin and went to his knees. He began dabbing up the spill on the floor and then looked up at Mrs. Corman. Their eyes locked. He moved the napkin to the toe of her boot and started rubbing it lightly, gathering the moisture "Oh, thank you Chris. They are brand new. Do you think they are too young for me? I mean, the boots? You know, a little to tall in the heel." Chris stammered. "Um, no. No, not at all. I think they look, um, pretty cool, I mean nice." A pregnant pause. "Chris, call me Diane. Please. I feel ancient when you say Mrs. Corman. Besides, I'm not going to be Mrs. Corman for much longer." He didn't know how to respond to that. Chris finished getting the spill off her boots. He stood up. She seemed pleased when she looked down at her boots. "Chris, you are ever the gentlemen. Oh, I think you missed a spot" They both laughed. "I did appreciate it, though." She looked towards the door to the living room. "Well, I suppose I should be more social. I hope to see you around." "Thanks Mrs. Corman, err, I mean Diane." "Good. That's much better." He watched her walk into the living room. His eyes followed her every move. Did he get on my knees and clean her boots? Oh, geez, what was he thinking? It was like he was now just coming out of some trance. He walked into the living room several times, pretending to see if anyone needed a refill. His eyes fell upon Diane. She was chatting with his mother. His eyes fastened on her stiletto boots. He was lingering over a table. He looked up. Her eyes had been upon him. She was looking at him quizzically. His cock was straining against his pants. Placing several coasters in his hand, he carefully walked out of the living room, hoping he had gone unnoticed. She busted him, didn't she? Inside his bathroom, he turned on the fan. Leaning back, he pulled down his pants. His prick was thick with blood. Each vein clearly visible against his smooth skin. He grasped his cock. He knew, in this high state of arousal, a few strokes would be all it took. Diane filled his head. He thought of the look they exchanged as he cleaned her boots. Oh god, he was coming so soon. Thick gobs spurted onto stomach and shirt. He moaned against the white noise of the ceiling fan. A knock at the door. Oh, shit, had someone heard him? "Hello?" It was Diane. "Um, err. Just a minute." Chris quickly flushed the toilet to make more of a distraction. He was breathing quickly as he raced to clean himself up. He looked down to make sure the cum was off his shirt. A pile of tissues in the toilet. Shit, shit flush faster! He was flushed, and still breathing quickly, as he opened the door. "Oh, I'm sorry. Chris, I didn't mean to startle you, but the other bathrooms were being used, and your mother suggested this one." "Oh, no, no problem. It's all yours." She looked down at his rumpled shirt. Her eyes lingered on his stomach. Was there something there? Does she can smell my cum? She raised an eyebrow. "Sure you are all done?" He gulped. Where was this going? She grinned. "Ha, ha. I'm just teasing you. Stop looking so seriously." He exhaled. "Oh yeah, yeah. Sure. Um, well, I'll be heading back to the kitchen." "Uh, huh." She smiled again, and closed the door. The party eventually cleared out. His mother came into the kitchen. "Chris, honey, could you get Mrs. Corman's coat." "Yeah, sure Mom." Diane followed him to the coat closet. "Thank you Chris." "Here, let me." He held the coat for her as she gracefully slipped into it. "Maureen, you son is the perfect gentleman." His Mom smiled. "Thanks Diane and don't forget to call that decorator." She left to join the others. Diane turned to Chris. His heart beat quicker. "Chris, I hope to see you again, soon. You won't be home for that long, no?" "Well, a couple of weeks." "Then, certainly you shouldn't be a stranger." She reached toward his hand and pressed a piece of paper into it, then leaned into his ear. "Call me." He must have looked like the proverbial deer in the headlights. "Okay." "Good. Then that's settled." She kissed him softly on the cheek. Once again, he grew very erect in his pants. He watched her click, clack in her boots towards her car. In his hand was a piece of paper with a phone number. Chris's mouth was dry. His stomach in knots. He wasn't sure about what he was doing. He dialed the number and hung up. Again, he tried. After a few moments, he heard her voice. "Um, Diane?" "Yes." "It's Chris." He was dreading the response, "Chris who?" "Christopher! I'm so glad you called. How are you?" "Good. Umm, I was calling because you had given me your number and all. Is it okay to call now?" "Well, you already did, too late to wonder." She laughed. "No, it's fine to call now. I don't know what your schedule is like, but I'd like to see you." "Okay. Should I come to your house?" "Well, I think that would be the best idea. I have some appointments, but how about 3:00?" "Okay, I'll see you then." "Very well Christopher, I'll see you soon." Why was she calling him Christopher? It made him feel like a little kid. He jumped into the shower, shaved, and stood in front of his closet, wondering what he should wear. Was this a date? What was this? He drove up the long driveway to her large house. Looking around, he slowly walked to her door. The urge to turn around, to just go home and call her with an excuse, lingered in his mind. He reached out to ring the doorbell. She looked stunning. Her hair was up, in a tight bun. She was wearing a gray suit and skirt. He noticed the gleaming, stiletto boots of the other day. Her face seemed different. Her makeup was more severe and her lips redder than he remembered. She escorted him in. "Chris, when was the last time you were here? I can't remember." "I'm not sure, maybe when you and Mr. Corman had that holiday party a couple of years back." "Oh yes," she said in a monotone voice. "A day from my previous life." He wondered how to respond. "Please, come into the den. Can I get you something to dink?" "No, I'm okay. " "Sure? Well, I'll have some wine." She sat next to him on the couch. Sipping her wine. His eyes fixed on her boots, again, as she bobbed them with her crossed legs. "Chris, you certainly are taken with my boots." He turned red. "It's okay. Lot's of men like them. Don't think I didn't consider that when I bought them." "Well. Umm." He swallowed hard. "They are pretty, um, cool." "Yes, you already told me so. In fact, you did get a closer look at them at the party." She reached over to her bag on the table and took out a pack of cigarettes. They were very long. He watched her extract one of the slim white cylinders and place it in her red lips. "Oh. Would you like one?" "I didn't know you smoked Diane." "Well, it's a fairly recent habit. I keep it from my friends, since it is so frowned upon these days. Just part of the many changes in my life. Leonard would have had a fit if I smoked." "Oh, how is Mr. Corman?." "Who cares?" "Do you miss him?" Diane lit her cigarette, his cock grew very hard as she exhaled a perfect stream from her lovely lips. She watched him carefully. "Miss him? Like the plague. I'm sure your parents talk about us. You see Chris, Leonard was an ass. He had been cheating on me with his nurse for years." She watched his eyes follow her movements. "But, it was a good thing. No longer am I the victim. I've taken control of my life. And without Leonard, I've discovered a whole different side to myself." Chris merely watched her and nodded. She faced him and exhaled at his face. "You like that, don't you?" "Huh?" "You know what I mean. I know you were touching yourself in the bathroom. When I went in, I could tell." "Um, Diane, well..." "Shh. Don't talk. I'm very attracted to you Christopher. And, like it or not, I'm going to make you come out of that shell of yours. You are a bit too sheltered. Don't you agree?" Chris just stared. Stunned into silence. "Hmm. There is much you have to learn, young man." "Chris. I like being in control of my life. I like power. The helpless wife routine didn't suit me and never will. I've embarked on a whole new lifestyle. My secret. Do you understand?" "I guess so." "You guess so?" Diane exhaled another plume of smoke at him. He felt himself lean towards her slightly. "Chris, get on your knees." "What?" "You heard me. Now." Without a will of his own, he found himself on his knees. "See, that wasn't so hard. Now, kiss my boots. Your eyes have been all over them. So, show me just how much you like them." He leaned forward and kissed the smooth, soft black leather of her boots. He moaned into the boots as he started to kiss and lick all around her ankles. "Now, suck on the heels." She raised one of her boots. Chris sucked all six inches of the stiletto heel into his mouth. He looked at Diane. She was leaning back, smoking, a satisfied smile spread across her lips. "Hah! Just as I thought. A natural. My submissive boy." She pulled the heel from his mouth. She looked at him. "Stand up. Now!" Chris rose to his feet. "Take off your clothes." "Huh?" "You heard me! Strip, boy!" Chris was startled by the change in Diane. Yet, his body was never so aroused. He felt consumed by her, ready to do anything for her. All kinds of thoughts flooded his head. What did she mean about her true nature? Was this his true nature? Slowly, he undressed. His cock was making a tent of his boxer shorts. She smiled and licked her lips. "Come on. All the way." Chris was shaking. He pulled down his shorts revealing his seven inch erection. It stood straight up practically, so engorged with blood that it grazed his lower abdomen. She stood and took slow steps around him, her eyes sweeping up and down. "My, my you are a healthy young man. Chris you make me very, very aroused. I think we are going to have a nice time together. Don't you?" "Uh huh." His mouth was so dry it came out like a croak. She stopped at his words. With her long read nails she squeezed one of his nipples and twisted it until he cried out. "What kind of answer was that?" "Yes, Diane." "Yes, what?" "Diane?" "Oh, Christopher, they don't teach you much in college do they? Mistress. You will address me as Mistress from now on, when we are alone. Do you understand?" She twisted his nipple again. Her red talons leaving marks on his exposed flesh. 'Yes...um Mistress." "That's much better. Now, say it again. Louder." "Yes, Mistress!" "Very good little boy. So lovely and pretty you are. Yes, let me look at you." Diane walked around him again. Reaching out to caress his ass and thighs, dragging her nails gently along his smooth skin. She flicked her hand along his cock, letting it fling back against himself. "Oh yes, a very healthy young man. I'm going to have so much fun with you." "You know Chris, you have a lovely figure." He blushed and shivered slightly. "Aw, so shy. I'm sure there must be some girls at school who would love to have you, no?" "I guess so Mistress." "You learn quickly. But you guess so? Don't you know?" Diane faced him again and leaned into him. She put her hands behind the back of his head and pulled him to her. Their lips met. He moaned into her as her tongue thrust into his mouth. He gently sucked on it as she forced more of her tongue and saliva into his mouth. His erection rubbed against the silk of her blouse. He could feel her press her body against it. She pulled back. Her pupils were dilated, a wide grin on her face. "Oh yes. Very nice. But look, I've left my lipstick all over your mouth. I'd wipe if off little Christopher, but it looks rather lovely on you." Chris ran his tongue over his lips, tasting it. "See there, it feels nice, doesn't it?" "Yeah, um, yes." "What!" "Yes, Mistress." "Then say it!" 'I like your lipstick Mistress." "Yes, I can see you do. We'll soon find out what else you like. Follow me!" Diane led him to a bedroom. His eyes never left her body as he followed her. His painfully erect cock shifting with each stride. "Christopher, you are to go into the bathroom here and get your body nice and wet in the shower. There you will find a razor. You are to shave off all your body hair, not that you have so much." She ran a finger along his chest. "When you are finished, you will find some clothes on this bed. Put them on and join me in the den. Do you understand?" Chris hesitated. "I don't know Diane, I mean, won't it itch or something? It's not something guys do?" Diane grabbed his cock and dug her nails into it. He screamed out. "How dare you question me!" "Yes, yess....Yes, Mistress. I'll do as you wish." Chris had to suppress the desire to cum then and there. He knew not where this pleasure came from, but he was finding a warmth spread throughout his body as he submitted to Diane. "Very good." Chris walked into the bathroom. He turned on the shower and soaped up his body. Diane had left him a ladies razor. He looked at it and ran it slowly over his light leg hair. He did this for some time before moving to his chest. Did she want him to shave his groin? He looked down and wanted to know what it would look like. He shaved that, too. He looked like a newborn, so bare. He walked to the mirror, clearing it of steam. He was completely hairless. He ran his hands along his smooth skin. It felt brand new to him, like he had never known it before. His cock was still very hard and he could clearly see his balls and lower shaft now. Modern Day Sentimental Education He walked to the bedroom. For a moment, he wasn't sure if this was the right room, for on the bed were clothes he thought for someone else. Diane had laid out what looked like a black leather corset. Straps hung from the sides. He had seen stuff like this in lingerie catalogs. Next to it was a pair of black silk stockings. On the floor, he was amazed to see a pair of black leather thigh high boots. Oh my god. Did she really want me to wear this? His hands shook as he slipped into the corset. He pulled on it very hard. It slid up his smooth stomach. It was so tight his breath did not come easily at first. He was thin, but the corset made his sides come in even more. Next, he sat on the bed and, as he had seen his mother and girls in movies do, he rolled up the stockings and unrolled them over his legs. He had nice legs, or so he had been told, from running. They silky material felt wonderful, he had to admit, over his smooth skin. With difficulty, he fixed the straps to the tops of the stockings. Everything seemed so taught. His cock rubbed against the leather of the corset. He eyed the boots. Could he even walk in them? He slid his foot in the first boot and, amazingly, it fit. Had Diane been planning this? The long zipper sealed the leather on his calf and thigh. It was tight. He touched the boot. It was of very soft leather. He loved the feel and smell of them. He extended his leg, admiring the boot. He put on the other one. Now, with trepidation, he went to his feet. His first few steps led to him falling against the bed. He tried again. The boots had what seemed just over 5" heels. They forced his hips forward and made the stockings and corset even more taut on his body. He tried to mimic the way girls walk in heels. That seemed to help. He swung his hips. For some reason, it was fairly easy to him. This troubled him. He looked in the bedroom mirror. He wanted to cum. He looked so, well, sexy. Pretty, even. He had a nice body. Sexy, for a guy; yet, the outfit added this wild, androgynous element. He slowly stroked his cock as he looked from the boots to the corset top. He turned to look at how the garter straps of the corset framed his ass. He wanted to cum, but knowing Diane would be displeased, he stopped. He walked down the hall to see his Mistress. The sound of Chris' heels echoed on the hardwood floors. When he entered the living room he was not prepared for the site before him. Diane had changed, as well. Like Chris, she was wearing a pair of black leather thigh high boots, but her heels seemed even taller. A tight leather corset and garters attached to shiny stockings peeked above the tops of the boots. On her arms she wore shoulder length black leather gloves. They were so smooth and tight looking. Her makeup was even more severe. But, it was what she held that made Chris' heart skip a beat. She was tapping a black leather riding crop gently against the side of one of her boots as she fixed her eyes on him. His Mistress approached him. "My, my, how sexy we look." Diane reached out to run her crop lightly around his cock and balls. "Mmm, and still so very hard. One would get the notion you are quite pleased with your outfit. Is that so little boy?" Chris looked down at the ground, averting his eyes from his Mistress. "Look at me!" Diane reached up to grab his balls with her gloved fingers and squeezed them. "Ahh!" "Look at me!" Chris raised his eyes. Diane slowly let go of his testicles. "Now, tell your Mistress how much you like your outfit." "I...I like my outfit Mistress." Diane flicked the crop against his erection. Chris flinched. "You can do better than that." "I love my outfit Mistress!" Diane walked around him, tracing the crop on his skin. "Yes, that's much better. It's obvious you love your outfit. But, it's not quite complete yet, no?" She walked to her bag and pulled out a tube. Chris followed her stiletto boots with his eyes. She walked back towards him. " Now, bend forward." Diane reached out and slowly ran the tube around his lips. "Good, now rub your lips together." Chris did as she said, feeling the creamy lipstick spread on his lips." "Oh, yes. My, you are a very pretty boy Christopher. Such sexy lips." Chris shivered. "Thank you Mistress." Diane smirked. She walked back to her bag and took out her cigarettes. Extracting one, she lit it in her red lips and then walked to Christopher. "Open your mouth!" Chris saw Diane's black leather gloved hand place the long, white cigarette in his lips." "Inhale, now!" Chris drew on the cigarette and coughed. "Slower slave!" Chris tried again, drawing just a little bit, exhaling a small stream of white smoke. He held the burning cigarette in his hands, noticing the red lipstick marks on the filter." "That's much better. Since you seemed so enamored of my smoking I'd thought I'd let you have a try. Now, hold it as I say." Diane instructed him how to hold the cigarette up by his side, elbow bent, like a girl. "That's better. Look at you. You ARE a slut, Christopher. Don't you think so?' Chris just held the cigarette, without answering. "Speak up!" "Yes." "Yes what?' "Yes, I am a slut, Mistress." "Yes, you are. Now, show me your slut walk as you smoke your girly, long cigarette. Only sissies smoke such cigarettes." Chris blushed deeply. He walked, trying to exaggerate his hip swing as he smoked the cigarette and held it like a girl. "That's it. See, now put your weight on your toes. You are quite good at this. Such an easy slut to train. Maybe I should call your mother and let her know." Chris froze in his tracks. "Oh god, no!" "What?" "Please, no Mistress." "How dare you tell me what to do?" "Please, I'll do anything Mistress, just don't tell her." Diane paused for a moment. She was dripping with excitement as she watched her young slave. "Hmm, anything? You may regret you said that. We'll see. Take another drag on your cigarette and hand it to me." Chris drew on the cigarette again and blew the smoke out of his pursed lips like he saw girls do. He handed it to Diane. She held it then took a long drag, blowing the smoke at his face. She walked to the coffee table and stubbed it out. "Come here. On the floor. I want you on all fours." Slowly, Chris walked over to Diane and got to knees. His high heels made it very difficult to hold his position. Diane sat on her couch and then put her booted legs up on his back. "Hold that position slave. Don't you fucking move!" Chris looked at the floor as he felt the weight of his Mistress's legs on his back. Diane picked up the phone and dialed a number. "Hello Maureen?" Chris started to shake. "It's Diane, how are you? Very well. Listen, I wanted to let you know I'm free for lunch next Thursday and I'd love to join you. Great, then 1:30 at Chez Henri's. See you then." Chris sighed. "There, there little one." Diane tapped his head with her crop. "I wasn't going to tell her now. But, if you fail to please me, I might have to take some photographs to share with her. Surely she would want to know what a sissy slut slave her son is." Chris shook. "Please, oh god. Please Mistress. Please don't do that." "We'll see. Now, get up!" Chris struggled to his feet, wobbly on his stiletto heels. Diane walked around him. Her leathered gloved fingers stroked his cock gently as she glared at him. He felt his cock grow painfully hard. She traced the head and slit of his cock. "Hmm, what's this?" Diane held up her finger, revealing a shiny sticky fluid on her black leather gloved fingers. "Pre cum? You better not explode slave. Lick this now!" Diane shoved her leathered fingers into his mouth. Chris sucked his fluid off the gloves. She laughed. "Hmm, I knew you would like it you little slut." Chris lowered his head. "Now, Christopher, after talking with your parents and observing you, I've come to the conclusion that you are a bit too full of attitude for your own good. We all noticed, at the party, the smug way you stood off to the side and looked at us. One semester of college does not a smart-ass make. You little twit. Someone needs to beat yourself out of you. Don't you agree?" Chris mumbled. "What's that?" "Umm, I don't know Mistress." Diane reached up and twisted his nipple very hard. "Ahhhh!" "Now, answer me properly you fucking slut!" "I need it Mistress." Diane released his nipple. "Oh, yes you do. More than you even know. Kneel on the couch. Get your fucking ass in the air!" Chris slowly walked to the couch and reached out to the backrest to steady himself. He placed both of his leather clad knees on the cushions. "Now slave, it's time for your lesson. After each beating I want you to count. Do you understand?" "Yes Mistress." His heart beat faster. His mouth grew dryer. "Good, now stick that slut ass out for me." Chris lowered his head to the cushions as he shifted his rear out. He never felt so exposed and helpless in his life. The cool air of the house meeting his naked rear. He wasn't sure if he could hear the sound of the crop coming through the air. The resulting pain cleared any other thoughts. Slap! "One!" Diane paused, feeling her loins flood with her juices. Her nipples rock hard above her corset. Slap! "Unh, two!" Slap! "Three!" "Oh, very good my slave." Slap! Chris paused. "Ugh, Four!" And on she went. The blood under his skin so apparent. Diane knew he wouldn't sit without pain for some time. Around the tenth stroke she heard his muffled cries. Chris clenched his teeth. He could feel the tears streak down his cheeks. Partly the pain and partly the realization of how hard he remained. This warmth that spread in his balls and shaft. He rubbed his cock on the cushions of the seat. His mind lost in a haze of pleasure and pain. Slap! "Ahhh, eleven! Oh god, no..no more....Mistress Diane...please." He was crying outright. She stopped. Diane leaned on the couch and caressed his hair. "Shh," she said as she stroked him gently. "There, there my sweet Christopher. It's okay." His sobs continued, but slowly subsided as she kissed his tears. She pulled his lips to hers and they kissed. Here tongue snaked in his mouth, marveling at the feeling of his lipsticked lips on hers. He moaned softly. For quite some time they let their tongues caress one another's as their passion grew. "Oh Mistress. I, I feel so different." Diane kissed his watery eyes. "Yes, I'm sure you do. I want you to belong to me Christopher. As my slave." "Yes. I want that, too. I'm scared Mistress, but, I..." "Yes?" "I love you Mistress." Diane kissed him deeply again. "In time you will love me, but now I think you are just overcome in the moment. Your training is far from complete, our bond not yet established." "But..." Diane laid her leather gloved finger on his lips. "Shh. No more talking. Now, get up Christopher." Chris stood to his wobbly feet, feeling a tremendous head rush. "Now on your knees before me." Chris kneeled before his Mistress. Diane reached out with her gloved hand and pulled the back of his head into her leather covered sex. At once, Chris felt her wetness around and against the black leather thong she wore. He inhaled the strong scent of leather and her cunt. He moaned against her sex. "Lick me slave!' Diane pulled on the back of his head and ground her sex on his mouth. He felt his nose gnash into her pubic bone as he not so much gave her head as she fucked his face. "Ohh...ohh......very good slave...oh...Chrisopher....." He could feel her body shake. She must be close, he thought. 'Ahhhhh..yes, that's it, yes! Yes..Unnn..fucking yes!" Diane shook against his mouth. He felt her girl cum as it dripped down her legs.. "Lick me there Christopher...all of it. Clean me my sissy boy." Chris gently lapped at Diane's cunt. He was inexperienced at pleasing a woman there, but soon learned he enjoyed the taste of his Mistress's juices. His lips were nearly numb from the pressure her mound placed on them. "Mmmm..yes, very good." Diane pushed him back hard. "Enough. Now, fetch me my cigarettes!" Diane leaned back on her couch. Chris pulled out one of her cigarettes. "Light it for me!" Chris placed the very long cigarette in his red lips and lit it slowly. "Look at you with that girly cigarette. You like to suck on it, don't you?" Chris looked down at the ground. "Yes, Mistress." Diane laughed. "Soon we will find out what else you like to suck on." Chris swallowed hard. Diane reached out to take the burning cigarette from him. She took a long, luxuriant drag and exhaled a full cloud of white smoke from her crimson lips. She felt delicious. Her eyes fell to Chris' still very erect cock. "Hmmm, would my slave like to cum? "Please, yes Mistress." "Very well. Move closer and rub your cock against my boot." Chris put his legs to either side of Diane's right leg. He moved against her so that his smooth, hard cock was rubbing on the black leather of her boot shaft." Diane felt herself grow wet at the feeling of his cock through her boots. A maniacal, lustful grin spread across her face. "Ohh." Chris was moaning softly as he moved his hips more quickly to rub his cock harder on his Mistress' boots. He was so close. Diane exhaled a cloud of smoke in his face. He felt her leg shift and move back and forth, urging him along and making more contact with his cock. The leather hot with friction and slick with his juices as it caressed him. He felt an explosive warmth move within him. "Oh god!! Mistress I'm going to cum!!!" Diane felt the warm spurts of his fluid through her boots. She sucked hard on her cigarette, moaning softly on her exhale. Ribbons of cum exploded from her slave, coating her boot shaft. "Oohh." Chris continued to move his cock back and forth against the cum streaked boots. Diane flexed her toes in the boots. "There my slut slave. Come here." Chris leaned forward and their lips met. Diane shoved her tongue deep in his mouth. Chris sucked hard on it as he pressed his cock into her boots. She pushed him back. She pointed to her boot. "You have made quite a mess slave. Now, clean it up. These are very expensive boots and I don't want to see one trace of your sissy cum on them. Do you understand?" Chris hesitated. Diane pressed the stiletto heel of her other boot into his cock. "I repeat. DO YOU UNDERSTAND?" Chris immediately lowered his head and lapped at his cum. At first, he resisted the slightly bitter stickiness but soon he was licking and swallowing. His tongue sought all remnants of his orgasm. He looked at Diane's boot shafts glistening with his saliva. "My, my you are quite the cum eater." "Yes, Mistress." Diane laughed. She patted the seat cushion next to her. "Come, come." Chris got up and sat next to his Mistress. Diane gently kisses him. Slowly they cuddled. She lit a cigarette and offered him one as well. He took it and smoked it as she had told him, like a girl. "Christopher, you belong to me, remember." "Yes, Mistress." "Good. Then, you are to go home today and tell your parents I have hired you to help with some remodeling in my house. Each day you are home for vacation you will be here. Is that clear?" Chris exhaled through his red lips, crossing his booted legs like he had seen women do. "Yes Mistress." Diane smiled at his girlish posture. "Oh yes. You are a fine student, how easily you see what you need to do. But, there is still much to learn. Yes, my slave, your real education is just beginning." THE END