2 comments/ 35152 views/ 15 favorites Being Instructed By: Lost Boy I got the phone call early Tuesday afternoon that I would be substitute teaching at St. William's Catholic High School. It is one of the few private schools in the city that I hadn't worked at yet. But with my sterling record and impeccable credentials it was just a matter of time. St. William's is one of the finest, most expensive and exclusive school in the entire state. To celebrate I cracked open a bottle of wine that a neighbor of mine had given me for my birthday; though I am not sure her husband would be pleased to find it missing from his wine cellar. She, who will remain nameless for her protection, was a very rich, attractive and very horny housewife. Since my teaching gigs were sporadic at best I had plenty of time of extracurricular activities; namely banging the lonely wives, daughters and girlfriends in the neighborhood. My record as a lover matched if not exceeded that of my teaching credentials. I have slept with mothers and daughters of the same household but not at the same time... yet. I have fucked many here in my home but most either at their houses or in my car or some fashionable outside location. The women didn't want to get caught but by god they took some serious risks. I remember a particularly close call at the local art museum with a very prominent wife of a political official; she wore the most accessible skirt in her wardrobe and I stood behind her while inside of her and her talented pussy milked me of a powerful orgasm. I nearly panicked when a friend of hers approached and she introduced me as her cousin. They chatted for a good five minutes all the while the dirty slut squeeze my cock with her pussy muscles until I came while friend stood a scant five feet away. When I let out a low moan she explained that I was a student of the arts and was overwhelmed by the display. I stepped out onto my back deck and set some wood in my fire pit and started a fire. I got my broom and swept the little snow that had fallen since I had cleared the surface off this morning. I love winter and nothing better than wine, a cozy fire and the knowledge that I had work the next day. I brought out one of my comfy chairs and set it by the fire pit and with wine glass in hand sat down and let out a little sigh of contentment. I closed my eyes and listened to the crackle of fire and smelled the scent of the burning wood and all was well with my world. After two glasses of wine the sky had reached full dark and I felt a little hungry so I opened the sliding glass door and pondered what to eat. I refilled my glass and opened the door to the fridge and looked around to see what took my fancy. Ding! I turned, closed the fridge door and walked over to the front door. "Who's there?" I called out. "Lucy... I saw your fire and brought some leftovers if you're hungry?" Her sultry voice told me someone was looking for some loving by my fire. I opened the door and stepped aside to let the leggy redhead in. She was wearing a winter coat and sweat pants that hugged her ass like a second skin. "You read my mind, I was just checking the fridge for food sweetie," I told her kissing her cheek. "Do you feel up to cracking open another bottle for lil old me?" She said batting her emerald green eyes. "For you anything and I do mean anything," I said the sexual tension thick enough to cut with a dull spoon. "I brought some steak, cheese and grapes," she purred. "Mmm perfect," I called over my shoulder from the far side of the kitchen as I looked in my closet I used as a 'wine cellar'. I picked out a wine that would go well with the food and by the time she had the food ready for us the wine was uncorked and her glass filled. "Haven't seen you around in a while Lucy what have you been up to?" "Oh... this and that," her voice held a naughty tone to it. "If I didn't know better I would suspect you were here to seduce me." "I don't know what you are talking about Ted." "Liar," I said smiling and handing her the glass of wine, "is it cold in here I can turn up the heat." I said seeing that she still had her coat on. "Oh don't bother I am waiting until after we eat to take off my coat." "Ah... is there a surprise for me underneath?" "Damn am I that obvious?" She seemed genuinely upset. "No... just a lucky guess." "Oh... okay..." she was back to all smiles. We moved out onto the deck and I brought out a second chair and we sat next to each other sipping our wine and feeding each other bites of food. I fed her a piece of meat and she sucked my index finger into her mouth and suckled it for a full minute before letting it go. Damn but it had been weeks since the last time we hooked up and it had been epic; tonight might prove to be legendary in its intensity! I took a grape and traced her lips with it before popping it into my mouth and she literally growled like a bitch in heat. It didn't take long to polish off the leftovers and moved to straddle me in my seat her ass facing the fire. "Gods I have missed you baby," she purred in my ear. "Are you ready for my surprise?" "You know I am," I said nibbling her ear. "Unzip my coat slowly..." I reached up and slowly pulled down the zipper to reveal bare skin beneath the coat and more of it! The little slut had been gone because she had gotten a boob job. She had always been conscious of her chest size and kept saying that one of these days her hubby was going to buy her the tits she should have been born with. The large B-Cup breasts I was so familiar will her gone, replaced by large C-Cup or maybe a small D-Cup. Her puffy nipples didn't seem to have suffered from the operation. I leaned down and took in her scent as I flicker my tongue over one then the other nipple and she moaned loud and long. "Well that answers my question." "What question baby," Lucy asked. "If your nipples are still as sensitive as they once were," I told her. "As you can see, they are the best money can buy." "Has the old man broken them in yet?" "NO... he is off on a business trip in Europe. He'll be back by Christmas hopefully, for the kid's sake that is." "So how do you suggest we christen these fine tits of yours," I asked. "What's the one thing I have always wanted to do but couldn't?" "Titty-fuck?" "YES... so why don't you drag me off to the bedroom, strip me naked and I will wrap these beauties around that long... thick... 'cock' of yours!" "How can I possibly turn down an offer as fine as that?" She stood up and I took her hand and led her off to my bedroom. She stood at the foot of my bed and kicked off her shoes and left the rest to me. I grabbed the zipper and pulled it down as slow as I could and in the dim light of the room her rosy nipples practically glowed. When the coat fell open I moved behind her and slowly pulled it off of her while I rubbed my cock against her ass. She moaned and pushed her ass against my crotch. I tossed the coat onto the rocking chair in the corner of the room and reached around and cupped her tits and began to softly, slowly massage her flesh. She growled and purred as her pussy got wetter and wetter. She ground her ass against me harder now and my cock was at full erection in no time. I took my sweet time cause I love teasing a woman and making her soaking wet before we fuck. After I could take it no more I lowered my hands from her tits to the elastic waist band of her sweat pants. Again slowly I tugged them down over her bubble butt and I actually knelt as I brought them to the floor. Lucy stepped out of the pants and turned to face me. I slipped a finger between her pussy lips and it slipped in with no resistance at all. I rubbed her clit a bit and I could see her actually shaking with need. I made little circles with the pad of my index finger over her clit and she bit her lip and ground her hips against my finger making it slip deeper inside. I withdrew my finger and licked it then sucked it while she watched. I stood up and she took the two steps separating us and began to tug my t-shirt up and off. Then she pressed her sensitive nipples against my chest and molded her body to mine. Her hand slipped between us and began to stroke the shaft of my cock slowly. Then when I could barely stand it she undid my belt, unbutton my jeans and let the fall to the floor. Not expecting company I actually wore underwear and she tugged my boxer-briefs down and off of me. Lucy gave me a gentle shove and I sat down on the edge of the bed and she walked over to the nightstand and retrieved the bottle of lube before kneeling down before me her eyes blazing with lust. She drizzled lube over and between her tits and rubbed it in until her flesh gleamed with a slick film. Lucy wrapped her breasts around my iron hard cock and began to rock up and down pushing her tits tight against my erection. Her enthusiasm was obvious and she even lowered her head and when the tip of my cock popped out from between her tits she flickered her tongue over the very sensitive tip. I watched as she greedily lapped the pre-cum from the tip. She switched tactics and gripped her tits so that she could move them independent from one another and massaged my cock now. I moaned and told her how good it felt with her tits wrapped around me and this just made her all the more eager to have my cock inside of her. "I can't take it anymore..." she moaned and stood up and shoved me onto my back. With a quickness that surprised me she pounced and impaled herself on my thick member. Lucy began to ride me and I let her do all the work. I cupped her tits and began to knead them and flicker my tongue over her nipples and that seemed to drive her closer and closer to the edge. St. William's was a massive stone edifice standing four stories tall crafted of polished granite that gleamed in the winter morning light. I parked my car in the teacher's lot and walked to the main entrance and was welcomed by the guard and directed to principal's office. The principal was an attractive Asian woman in her late forties but due to regular exercise and a healthy diet looked barely thirty. She told me that my services had been contracted for two months and depending on how well I did I might even land myself a permanent position at St. William's. I smiled and told her I would do my best and wouldn't disappoint her. I was given a folder with paperwork and a map of the school. She had circled the classrooms I would be using as well as a schedule up to the Christmas break. She and I would meet after the break to see how my services would best be put to use. I scanned my schedule quickly and took my leave of her and headed for my first classroom. The school was the finest building I had ever set foot in. The floors were polished marble and the interior walls matched the outer with its gleaming black granite. The oaken doors were heavy and carved with an elegant beauty that was reminiscent of old world style. The students were the elite of the state and in some cases surrounding states. The uniform was a black cloth with silver piping and a heraldic crest over the left breast. The boys wore pants and the girls wore either slacks or skirts depending on the weather. Today there were few girls wearing skirts due to the bitter cold outside and the nippy atmosphere within. I found my classroom and there were actually a few students who were already seated as I made my way to the gorgeous mahogany desk with its New England craftsmanship and gleaming brass fittings. I set my briefcase carefully on the desk, sat down and took in my new environment. I had to admit I was a little intimidated but if I could actually land a job her I would set. The first bell rang and I heard the rumble of feet and voices and soon the room was full of students and before the second bell they had taken their seats and were quiet. Weird. I stood up as the second bell rang and turned and to my utter dismay a state of the art smart board took me completely off guard. I turned back to face the class and smiled. "I was going to write my name on the board but the chalk I bought isn't going to do the job now is it?" They actually laughed and a cute girl raised her hand and I nodded to her. "Mr?..." "Baker." "Ah, Mr. Baker in the belly drawer of the desk is an IPad you can use that to access the smart board or if you want I can help." I opened the belly drawer and took out the IPad and turned it on and looked at the aps and saw the one for the smart board and with the press of a button the board came to life. I keyed in my name and again the class gave me a good natured laugh. I think I was going to like this school. "Okay from the top," I said, "I am Mr. Baker and I will be your substitute teacher while Ms. Young is out sick. It appears that you were studying the Civil War is that correct?" There were nods and I found the history lesson and where Ms. Young had left off. I loved the Civil War and set right to work asking a few preliminary questions and found the class both intelligent and receptive. Before I knew it the bell rang and I handed out the prescribed homework and with smiles and a few handshakes I was welcomed into the family of St. William's. One stocky male student stayed behind and waited for everyone else to leave. "Mr. Baker?" "Yes?" "I wanted to know if I could ask a favor." "What sort of favor?" "Well yesterday Ms. Young confiscated my smart phone and I was wondering if I could have it back?" "Why did she take it in the first place?" "She caught me texting in class." "Honest, I like that. Well I will give it back... but if I catch you repeating that mistake you won't get it back until Christmas break... fair?" "Fair." "Okay, now where does she keep her hoard?" "Second drawer on the left hand side, it's the one with the electric blue backing." I opened the drawer he indicated and found no less than six cell phones. His phone was near to the front of the drawer. I handed it back to him and told him not to disappoint this good will gesture and he seemed quite sincere on not texting in class anymore. Then he was off and running for his next class. I had a free period and my third hour class was in this room so I decided to get comfortable and play with the smart board for a bit. I closed the second drawer and it caused the bottom drawer to pop open and what I could see made my jaw drop. I went over and closed the door to the classroom and opened the drawer all the way. What had caught my eye were three bottles of anal lube, two were empty and the last was half full. Below the lube were all manner of toys from ball gags to butt plugs and from vibrators to dildos. Was this woman insane or just looking to lose her job? Maybe this was the opening the principal had mentioned? Tucked in the back of the drawer was a second IPad but this one was a custom model with an inscription on the back cover that read... 'To Carol, My Inspiration...' I closed the drawer and turned on her I Pad and found the files and aps much different than that for the one at school. There were tons of pictures loaded in various folders marked redhead, brunette, blonde, anal, oral and others. I opened the 'anal' folder and damn this woman was hot! She was on all fours and taking two cocks at once and in some there were three guys involved. As I perused her files I found folders with videos in them as well and I decided at the moment to 'borrow' her I Pad and take it home for a better look. I met the other teachers at lunch and asked a few subtle questions about Ms. Young to see if any of the male teachers showed any signs of knowing about her hidden toy hoard. But I was disappointed to find that Carol Young was a pretty quiet demure woman as far at the others were concerned. How interesting she was a closet freak this was going to be fun! The rest of the day seemed to crawl and all I could think about was getting home and watching the movies our sweet demure Ms. Young had made. At last the final bell rang and I made my way to my car carrying my briefcase and in it 'her' I Pad. I arrived home and waiting for me on my front porch was Diane Lane a neighbor's daughter. I pulled into my garage and she met me as I exited. "Hey Ted!" "Hi Diane how are you?" "I'm okay..." "What's wrong?" "Can we talk inside?" "Okay, does your mom know you're here?" "She's the one who suggested I come and see you." "Oh okay..." I unlocked the door and waved her in before entering myself. "I am having problems at school and mom said you might be able to help." "What kind of problems?" "There's this girl and her friends..." I could see the tears start to flow. "Are they giving your grief?" Diane nodded and I gave her a hug and the damn burst and she was sobbing and her body shook with the pain. I waited for her to calm down a bit before asking any questions. "How long," I asked. "Since the beginning of the year," Diane whispered. "You want help getting them off your back?" "Can you help?" "Have you talked to the teachers or a counselor?" "Yeah but she is the superintendent's daughter." "Really, no wonder everybody is keeping their distance. I'll have a talk with him, he and I play golf sometimes and he owes me a favor." "Wow, I really appreciate it if you ever need a favor..." "Actually... do you know how to sync an I Pad to a television?" "Sure if the TV is new enough let me take a look." "Okay I am going to change into some sweats, take a look and I'll be right out." I had barely changed when the sounds a woman in the throes of passion came to me. I came racing out and there was Diane watching the TV screen with a look on her face that appeared a look of shock and pure lust. "Diane I can explain..." "Damn... how does she keep from choking on that monster?" "Um... what?" "Look at the cock on that guy..." It was the way she said 'cock' that caused my sweat pants to tent and Diane didn't miss it. She set down the I Pad and walked over to me and dropped down to her knees and with a very unladylike yank freed my dick. Her tiny hand wrapped around me and I began to freak out and then she put me at ease with just a few special words. "Ted, relax I'm eighteen and I want this." She took me into her mouth and licked and sucked the head expertly. "Where did you learn that?" "Mom told me all about you and your fabulous cock. She's the one who taught me how to make love to man and swallow every last drop. So shut up and enjoy this." She split her attention between me and the TV screen which showed Ms. Young sucking a long thick cock and loving it as much as Diane was. Diane was a thin girl with small breasts but an ass you could bounce a quarter off of. She wore her brown hair long and her glasses gave her an extra sexy factor. As she sucked me off she was undoing her jeans and using one hand then the other tugged them down over her ass and then she began to finger her pussy as she deep-throated me. As Carol got on her hands and knees to get fucked doggy style so did Diane. She kicked off her shoes and lost the jeans. "Come on Ted fuck me, fuck me good!" We were mirroring the video and damn that was hot! I knelt behind her and teased her pussy before sliding in nice and slow. "Damn Diane your pussy is so fucking tight!" "Should be..." she grunted. "Why is that?" I asked as my cock finally penetrated as deep as it could go. "You're my first." "What?" "Mmm so thick..." she moaned as she began to move against me as her gaze never left the TV. I positioned us so that she was able to more easily see the TV screen and we once more mirrored the action before us. I slammed my hips into her and her moans got louder and louder and felt her pussy start to squeeze me tighter still. It was clear to me that Diane was close to climax. Being Instructed "Are you going to cum for me Diane?" "Yes... so much better than masturbating..." "Yes it is!" "So close, I am so..." then with a cry her head was thrown back and she came hard her very tight pussy squeezed me like a velvet fist. When she had recovered she looked up and smiled. "My turn on top baby," Diane called out and I pulled out and laid down on the carpet. Diane still hungry for cock stood and straddled me and slowly lowered her once virginal pussy down onto me. I felt her pussy lips open slowly as inch by inch I entered Diane once again. "Oh god baby so thick! I can't wait to cum again!" "Lean down so I can taste those nipples of yours." "Mmm okay..." she leaned over and she gasped as my tongue flicker over her pebble-like nipples. "...oh god that feels great!" I grabbed her hips and began to lift and drop her on my length and she began to gasp and groan. Her cries got louder and louder as another climax followed the first. "Turn around and face away baby so you can watch the TV I can tell you like to watch," I told her and she smiled and without me leaving her pussy she spun around on me. Now it was Diane who was in control and she was bouncing up and down telling me about how the woman in the video. "You should see the look on her face baby... his cock buried deep in her pussy... ooh now she is sucking him off again but I like your cock buried in me like this..." "Me too," I told her as I decided to surprise her by flexing my dick inside of her. "Whoa what was that? That was amazing do it again!" As she ground her hips against me I continued to flex my cock in her again and again. Then Diane went stock still and perfectly quiet. I leaned my head so I could see the TV and there in all her sensual glory Carol Young was getting ass fucked by that cock Diane was so enraptured by. "Holy Shit! I thought taking it down her throat was impressive but up the ass!" "I guess you're not ready for that eh kiddo," I muttered knowing she would stop mimicking the action on the video at this point but boy was I wrong. "What, you don't think I have what it takes to have that cock of yours in my ass?" "That's not what I meant... I just figured you wouldn't be comfortable with that sort of thing so soon after losing your virginity is all." "Oh, I appreciate the sentiment but... well... do you want to?" "Do I want to what," I asked smiling ear to ear. Diane spun around again without my dick leaving her pussy and she looked down at me her eyes literally blazing with lust. She leaned down and whispered in my ear. "Hey Mister... would you like to take my anal virginity too?" "Lube is in the top drawer of the nightstand in my bedroom." Giggling Diane stood up and made her way to the end of the hall and with a whoop returned with lube in hand. She handed me the bottle and got on the floor with her head down low and her bubble butt high in the air. "Lube me baby!" Her mother was going to kill me, hell her mother and I hadn't had anal sex and it had never been mentioned. So here I was crawling over to her daughter, unscrewing the lid and adding a very liberal amount of lube to her very tiny puckered anus and my aching cock. "The key to this is to relax... don't tense up okay." "Okay but go real slow okay baby..." "Absolutely, now I am going to do a little trick to help you relax okay?" "I trust you completely." I lubed up all four fingers on my right hand and slid my index finger into her ass ever so slowly and the little slut let out a low moan. "I think I am going to like this..." I began to finger fuck her ass slowly and felt her relax almost immediately. When I felt she was ready I eased the middle finger next to the index in her ass and when they were seated I slipped the other two fingers into her pussy. "Oh yeah baby! That feels fucking awesome..." I began to finger both holes slowly and she relaxed all the more. She was grunting and before too long was pushing back against my hand. "I like your trick lover... both holes filled so nice... are you going to stick your cock in me soon?" "When you're ready," I told her. "Oh I am going to cum with just your fingers in me... oh god so good..." True to her word Diane let out a yelp and both holes spasm around my fingers as her climax hit her hard. "Best... one... so far..." "I think you're ready Diane." I slowly pulled my fingers from her ass and pussy with a wet pop and took the slick head of my cock and lined it up with her anus. But before I could push forward Diane pushed backwards eager to have her ass full. With a series of breaths the large head of my cock popped into her ass. Then when she had acclimated she pushed back again and her butt swallowed me to the base. "Lover, you're all the way in my ass! Fuck me baby... fuck my ass..." I grabbed her hips and began to very slowly move and she growled as the pleasure flooded both of us. Her noises got louder and louder as she began to move with me and I was fighting back my orgasm with all my might. "You're getting bigger in my ass baby..." "I am so fucking close Diane... where do you want me to cum?" "Fill my ass baby... shoot your load deep in me." We never reached a fast pace but I was amazed at her capacity to take a cock in her ass. I doubt it was a full minute later that my toes were curling and I cried out as my cock swelled and swelled until... I rammed my hips forward and buried myself as deep as I could and a flood of sperm was released deep in Diane's ass. "Yessss I can feel your cum in my ass lover!" It was at that exact moment I heard the front door close with a metallic click and we both looked behind us to see Diane's mother standing there white with shock. "Hi mom!" Diane gathered up her clothes and I told her where the bathroom was so she could clean up. I heard the shower and a contented sigh as Diane slipped under its hot water. When I turned Ellen, Diane's mother, was in my face. "Have you lost your goddamn mind? I sent Diane over here for support not... can you turn off the TV that is very distracting." I looked over and Carol Young's epic stamina was obvious as three guys were now in the scene one in her pussy, one in her ass and the last down her throat. "Sorry." "Is it your habit to show porn to seduce young girls?" "That was an accident..." "How do you accidently show porn to someone?" I explained how I had borrowed the I Pad from the school and asked her to check the TV not to actually touch the tablet computer. "So Diane took it on herself to open the files and display them on the TV?" "Yes..." "Sounds like her... headstrong... curious... just like her mother." "So you see it was all an accident." "All... so your cock just accidently ended up wedge in her ass?" "That was her idea... she saw it on the video and wanted to see what it was like." "You never told me you were into anal sex Ted..." "You're a suburban housewife... I never dreamt you'd want to..." "Shows you what you know about women. But I am still livid about you taking my daughter's virginity... both of them." "I'm not it was amazing!" Diane appeared in just a towel hair plastered to her back. "You young lady, get dressed and head on home I will deal with this situation." "Yes mom..." Diane turned, dropped the towel and wiggled her ass at me before disappearing down the hallway. "Just like her mom," I said with a wicked grin on my face. "You are a bad man you know that." "I'm not the one who taught her to suck cock so well." "Of course she told you that." "Hey somebody's got to do it, might as well learn it from someone you trust." "So what site did you download the porn from?" "I didn't... it belongs to the teacher who owns the I Pad." "You're shitting me?" "Nope, I found it along with a lot of toys in her desk at school." "Why did you bring it home... oh duh... you were going to watch it and..." "Yep got it in one," I told her. "So what are you going to do now?" "You know me... what do you think is my next move?" "I'd blackmail the slut and force her into some very gratifying sex," Diane chimed in now dressed and hair semi-dry. "Young lady!" "She's absolutely right of course," I said with no sign of guilt whatsoever. "You're not kidding," Ellen said shocked. "No, I am going to download every file on her tablet and use it as leverage." "Why?" Ellen asked. "Why not..." Diane and I said in tandem. "You two are incorrigible," Ellen said smiling. "She's a freak I doubt she'll mind having my cock in her ass, down her throat... fill in the orifice of your choice." "Can I watch?" Diane asked. "No!" Mom practically shouted. "Maybe..." I said just trying to annoy Ellen who spun on me and glared with parental claws fully extended. "She will not be involved in your little scheme and that... is... that. Now get home right now Diane and we will discuss your punishment when I get home." "Yes mom," she said aloud and when mom wasn't looking she mouthed... 'call me.' Once Diane was gone Ellen glared at me torn by some sort of internal debate. "Let me guess," I started, "part of you knows you have to go home and deal with Diane. However there is the other part that saw the video and wants to drop down to her knees and worship my cock and have it in her ass. Am I close?" "Damn you Ted!" "That's not a denial is it?" "NO... I haven't gotten fucked in weeks and it is tearing me apart. I walk in on you and Diane and god help me I am soaking wet between my legs right now. Am I a bad mother?" "Ellen," I said walking over to her, "you are doing the best you can since that piece of shit husband left you guys. Tell you what... how about just the two of us go out to dinner tomorrow night and you can blow me under the table and afterwards I'll fuck you rotten in our favorite spot." "The top level of the parking garage," she asked. "Yep." "It's a date." She said closing the distance and kissing me fiercely. My cock was hard in seconds and it took all my self control to break the kiss and direct her to the door. "You have a daughter to punish and I have research to do." "But look you are hard as a rock baby... let me suck you off at least." "As tempting as that is... you're daughter would know and that would set a bad example." "You're right..." she said sounding like a teenager again, "I will just have to go home and masturbate thinking about that long, thick cock of yours." "GO, before... just go..." Slam when the front door and I regretted sending her home almost immediately. But I had gigs of movies to go through as well as the other files on the I Pad to look through. I didn't watch them all and skipped from scene to scene in some cases but a definite pattern was becoming clear. Carol Young was a complete and total sex addict. Most footage seemed to come from a single location, her home I assumed, but the other scenes were from outdoor locations such as parks, the sides of roads and even a church. Watching her fucking on an altar both disturbed and excited me at the same time; as did the nun costume she wore at the time. I was sure I would dream of a beautiful nun sucking me off tonight and looked forward to bedtime. She also had three email accounts dedicated to hooking up with local men and she was very prolific slut of that there was no doubt. From the emails and her digital diary I counted her partners over the last two years number well into three digits! Who said sports stars were the only ones who had a lot of sex? Being Instructed: Lesson the Second I finished out the week while Carol Young recuperated from her bout with pneumonia and made, polished and implemented my blackmail plan. I had copied everything I required from her I Pad and returned it to her bottom drawer but removed all of her toys and arrived Monday morning with a bounce in my step and a whistle on my lips. I wondered how long it would take before she noticed the toys were missing and of course she couldn't say a damn thing to anyone, anyone that is but me. I never planned on keeping my part secret. My plan was simple and straightforward and was foolproof. I was tutoring some of the students for exams when Carol Young arrived at my newly appointed office. She looked flushed and just a touch of fear in her eye, excellent! She knocked on the open door to get my attention and when I looked up I had on a mask of perfect calm. "Can I help you," I asked. "Mr. Baker," she asked her lower lip trembling. "Yes, you must be Ms. Young. Are you okay you look a little pale maybe you should still be at home recuperating?" "I am a little dizzy..." "Please have a seat..." I turned to the two students, "can we finish this at another time please?" "Oh sure!" Ms. Young sat down as the students rose and left. I stood, walked over to the door and closed the door. "Now what seems to be the problem," I asked her playing ignorant. "Some items were removed from my desk and I was informed you were covering for me while I was away." "Yes, I was the substitute teacher... what sort of items are missing?" She narrowed her eyes and glared at me. "You fucking know what things you took!" she hissed at me. "I don't know what you mean Ms. Young..." I said cracking just the hint of a smile, "are you accusing me of theft; do we need to go the principal and discus this matter with her?" "NO," she bit back a shout. "Then how do we resolve this situation I am open to suggestions." "What do you want," she asked looking me over. "Well... from the photos and videos I have seen..." "What?" "Your tablet computer had some very 'interesting' material on it. Pity you didn't add a password protection on it." "You've seen ... you watched... oh my god..." "If I may put things into plain English... you my dear are a freak and a slut." Again she glared at me with unbridled hatred. "How much," she asked. "How much what?" "Money of course..." "Do you really think this is about money?" "I assumed... if not money then what... oh... I see..." "Your ass my dear Ms. Young literally belongs to me." She lowered her head to the table and wept. "Why are you crying," I asked observing her demeanor change, "I have no plans on telling anyone anything if you agree to my simple and elegant rules." "Rules... what sort of rules..." "If you check your email account you will find them attached to a document." "Which account?" "Slutslave69..." "You went through my emails too?" "Ms. Young there are no files on your I Pad I didn't go through and download." "You have copies of..." "Every damn thing," I said smiling wickedly now. "You are going to leave your vehicle here at school and take a little drive with me after school... afterwards I will return you to school to pick up your car." "A ride?" "Yes... it has been forever since I have had decent road head... don't disappoint." "Oh I won't..." she said with a smile understanding I was going to exploit her slutty nature to it's fullest. "Good... now slave get the hell out of my office." "Yes sir." Another incredibly slow day at the school but at last the final bell sounded and I collected my things and headed for the parking lot. True to her word and not having any choice in the matter Ms. Young was actually waiting for me. She followed me to my car without a word and once in the passenger seat I could see she was nearly bouncing there she was so eager to suck me off. "It appears your demeanor has changed since last we spoke," I said. "All I could think about for the rest of the day was your hard cock in my mouth. I kept trying to imagine what it looked like, how long... how thick..." "Well once we get on the road you will find all of that out, now be a good slut and buckle up." "Yes sir." We drove for a couple of miles before I reached over and cupped a tit; she moaned like a whore in heat. "Get to work slut," I said and she unbuckled her seat belt and leaned over to free me and suck my cock. "Thank god..." she moaned once my cock was exposed, "I was praying that you'd have a nice long thick cock." "Less talk more sucking..." I felt her lips wrap around the tip and her tongue begin to tease the sensitive flesh. I let out a soft moan and then I felt as she took a few inches more into her mouth and her tongue swirled around tip and shaft and her cheeks caved in as she applied suction. After a bit her head began to move up and down and remembering her videos I grabbed her by the hair and made a tight fist and started to guide her speed and depth she started to moan deep in her throat sending delicious vibrations through me. I moved her head down until her nose brushed against the base of my cock and held her there for a bit before pulling it up again. "I do love a slut that can deep-throat, now impress me..." saying that I let go of her hair and spurred by my words Carol's head began to move up and down the entire length from tip to base with no sign of a gag reflex at all. "Mmm that's it cunt you are beginning to impress me..." She licked, sucked and pleasured me with all her skill and I had to admit it she definitely knew her way around giving head. Fight though I may I felt my climax building and felt the inkling in my toes and told her so. "My toes are starting to curl slave, do you know what that means?" She did and doubled her efforts to please me and when my cock swelled in her throat she moaned all the louder and sucked all the harder until... "Oh fuck! Get ready to swallow slut!" and hardly had the words left my lips that pulses of hot cum shot down her eager throat and she gulped them down greedily. "Sir that was delicious! Thank you for letting me suck you off!" "You're welcome slave; have you read the email I sent you yet?" "Indeed I have," she moaned as she licked me clean and tucked my cock in and carefully zipped me up. "And..." "I will gladly follow the dress code and behavior guidelines you have set down. Is that how I will earn my toys back Sir?" "That's the idea... look in the glove compartment." Carol sat up and opens it and smiled like a kid in a candy shop. "My ball gag, it is very useful when fucking in public places because I tend to be very loud." "I know. Now be sure to wear a skirt tomorrow and you might earn your dildo back." "Darn... I was hoping for my butt plug." "All in good time," I told her. Before too long I dropped her back off at school and her car was the only vehicle left in the parking lot. "See you tomorrow Sir." "Goodbye Carol." Being Instructed: Lesson the Third Christmas vacation was quickly approaching and Carol had earned back a few of her toys but the butt plug was the last one she was going to get. We never had sex on the school premises but that didn't stop me from teasing her with her remote vibrator buried in her pussy. After school we had fucked in the car, in the park, and even in a restaurant bathroom. For all the partners she had been through her pussy was still damn tight. The one act she refused to perform was fisting and I don't say as I blame her that would ruin her pussy or ass for good. I told her a few days before Christmas break when she was going to earn her plug and she was delighted; fucking her ass was going to be my present to myself and we were both looking forward to bending her over the Yule log. As I promise Diane I spoke with my friend the superintendant about his daughter. The coffee house was quiet after the lunch crowd had come and gone. It was small affair that could hold maybe fifty people at capacity and it was a spot that Paul and I had frequented quite often when we were younger. Paul Grace was a man in his forties with carefully coifed hair and impeccable taste in clothing and women. He was taller than I standing a little over six foot with dark hair and eyes and features that reminded me of the old Roman emperors with his hawkish nose and firm chin. When he looked at you it was like staring down a bird of prey and I learned early on not to blink. He respected that and I did small favors for him from time to time. On that day he was wearing a steel gray suit with a dark tie and mirror bright shoes that he had polished himself; ex-military got to love them. Being Instructed "So Ted what is so important you wanted to meet here?" his voice was low and had the cultured authority of a man used to getting his way. "Well Paul it's about Amber..." "Aw god what has she done this time?" he said pinching the bridge of his nose making the stress headache that was his daughter go away. "I was approached by a girl in her class who is being bullied..." "Say no more... I take it because she's my kid none of the other teachers will do anything about it?" "Bingo... I am sorry Paul." "Don't be, I am the one who is sorry the little bitch thinks she can get away with this shit because I'm her father. Are you willing to handle it for me?" "Me? Well... if you can call the school I am working for and tell them you are sending me out during work hours for you..." "Done... you have always had my back even when things haven't been easy and I appreciate it. I'll put in a good word for you; which school are you subbing at?" "St. William's," I told him and he smiled brilliantly. "Nice place and they are lucky to get a teacher of your caliber Ted. I will call them tomorrow and do me a favor... don't be lenient on her it's the only way she is going to learn her place." "I didn't plan on it I know how bullies think." "Refill," he asked and I nodded. We passed the next hour catching up on more pleasant business. I hadn't seen Amber in a few years as she was with her mom on holidays and wondered how she had grown since then. She was a headstrong girl from an early age and I was thinking this is the key to her problem with authority. She had always had her way and I wasn't kidding myself thinking this task was going to be a walk in the park, it wasn't. The next day I got a call an hour after arriving at work to go to the principal's office. Erika Watanabe was smiling when I entered and offered me a seat. "I just got off the phone with the superintendant and he says he has spoken to you about a task he needs you to perform today during work hours. It pleases me to no end that our staff can be of help to his office so take all the time you require and make us proud!" "Thank you Ms. Watanabe." "Please call me Erika." "Thank you Erika." I wasn't 100% sure the permanent position at St. William's was mine but I was sure feeling better about it after my meeting with Erika. I drove over to the Stafford Academy where Amber attended school and was immediately impressed with the layout of the place. Though not as tall and grand as St. William's, Stafford was modern, sleek and screamed money. I am not sure how it ranked in the state but I suspected it was damn close to the top. The female security guard that met me at the parking lot looked like she could crack walnuts with the thighs on her and like Paul had that glint in her eye that brooked no fucking around. "Mr. Baker?" her voice was soft and sultry despite her appearance. She wasn't ugly at all just very severe in her attire and manners. I am guessing she weighed in about a buck and a quarter and that was due to her athletic build and height at five foot six inches. Her blond hair was up in a tight bun and her bright blue eyes assessed me for any signs of a threat. She had high cheek bones, a button nose and full lips that were curled in a sardonic smile. "Yes I am Mr. Baker." "You are here to meet with Amber Grace." "I guess you could put it that way." "What do you mean?" "Her father sent me here to teach her a little discipline so I think it more appropriate to say she is here to meet me." "Thank god!" I almost busted out laughing as the guard lost all sense of authority and began to tell me all the horror stories that surrounded Ms. Grace. As her father and I suspected due to her father's position with the board of education teacher and student alike were scared to death of her. Amber and her posse caused nothing but trouble and chaos wherever they went. "Which classroom will I find her in," I asked and Cheryl the security guard laughed. "None, she'll be in the girl's bathroom on the second floor I'll show you the way." It wasn't far to my destination. We reached the girl's bathroom and Cheryl offered to go in and get her but I shook my head. "I'll take it from here." "Good luck... you're going to need it." "I know... I know." I opened the door and immediately smelled the distinct scent of pot in the air; damn this girl was bold as brass! I walked in and I recognized Amber immediately but not her two friends. "What the fuck! Get out of here!" Amber yelled at me. "You two make yourselves scarce and pray I don't call the cops and have them pick you up for possession of a controlled substance." Poof! Like smoke and mirrors they were gone. Amber turned on me with unchecked hate in her eyes until she realized who I was. "Uncle Ted? What the fuck?" "Amber, it's good to see you too. Now flush the joint down the toilet or I will." "The fuck you will!" I crossed the distance between us and before she knew what was going on I had her in wrist lock and was dragging her to the nearest stall. When her hand was over the toilet I squeezed and her numb fingers released the smoldering hand rolled cigarette and it fell into the bowl with a soft hiss. I used my foot to flush the toilet and then released my hold on her. "No permanent damage," I told her as she rubbed lift back into the offending hand. "When my dad hears about this," she threatened. "Your dad sent me Amber." That took the wind out of her sails and all her blustery attitude died still born in her throat. "What? Why would he send you here Uncle Ted?" "You want it sugar coated or the unvarnished truth?" "Just tell me what's going on." "Well precious you have turned into a Grade A bitch." "How can you say that," she asked while standing in the bathroom smoking pot instead of being in class. "Take a look around you. You are in the girl's bathroom smoking dope and that doesn't sound a little off to you?" She shrugged and I could see the wheels turning but nothing came out of her mouth so I continued. "I had the school email me your grades for this year... you are going to fail senior year again. Amber you are nineteen and still in high school does that sound like things are peachy keen?" "No..." she said her head held low. "The only reasons you haven't been arrested or kicked out is because of your dad are you proud of that?" "No..." her voice was softer still. "You're a bully and a petty criminal what's going on?" "I don't want to talk about it!" "Okay I make a deal with you; you and I go out for the day and you open up and fill me in with this self destructive course you've chosen for yourself or..." "Or what," she said looking up with a hint of fear in her eyes. "Or I take my phone here and dial 911, your decision." "You're not serious... what about dad?" "Your dad wants you to succeed and turn your life around and so do I. But if you don't tell me what's bothering you, you don't leave me much alternative." "That's blackmail!" "Not the first or the last time for me sweetie," I told her with ice in my voice. "But..." her voice began to break. I reached into my pocket and took out my cell phone. "...okay! I will talk god damn you!" "Good," I smiled and put my phone away. "Now follow me to the principal's office and we will get you cleared to leave the school with me." An hour later we were on the highway and heading in no particular direction. I had a full tank of gas and she was sitting in the passenger's seat pouting. "Okay Amber... talk," the last word spoken with a clear note of authority. "I hate them!" Three simple words but they defined her entire universe. "Your mom and dad," I asked. "Yeah... ever since the divorce they don't talk and can't be in the same room for more than a minute." "Who do you blame?" "Well isn't it obvious?" "Not to me." "It's all my fault!" "How can their divorce possibly be your fault?" "I don't know but it seemed like since I came along they grew apart and..." "Sweetie... I know all those Disney films talk about happily ever after but truth be told the majority of relationships just don't last. That's not to say we shouldn't try but what happened between your mom and dad had nothing to do with you. It was them." "Uncle Ted..." Amber said with tear stained eyes, "...thanks." "Don't thank me yet," I told her. "Why?" "Because you still need to get your shit together; I expect you to be in class, every class, from tomorrow on. You will do every bit of homework and pass every test or else." Her tears were gone and the cold calculating Amber was back. "Are you threatening me Ted?" Gone was uncle now I was the enemy. I was the force of implacable authority and I would not bend on this. "No, a threat may not be followed up on. This is gospel Amber and if you don't follow it to the letter there will be repercussions." "What are you going to do spank me?" "If that will straighten your ass out then so be it." "You're not serious! I'm nineteen years old." "Then start fucking acting like it!" "You ain't got the balls old man," her voice was low, cold and full of venom. "We'll see Amber. I gave the principal my cell number and if you don't comply then you'll see who wins this situation." "Let me out of this car!" "As you wish..." I said taking the next off ramp and then getting right back on the highway heading straight back to school. "Where are you taking me?" "Back to school," I said coldly. "Wait, you said we would spend the rest of the day..." "That was a reward for good behavior, it's not like you are cooperating." "Why are you doing this to me?" "Because you are out of control, you lack discipline and if you keep up like this you are going to end up in jail." "Give me another chance," she begged. "Okay... if you can keep from cursing for an hour we will continue our little drive if not straight back to school... agreed?" "Agreed," she said solemnly. For the next hour we drove on in silence; she ignored any and all attempts at conversation and looked out at the road lost in her thoughts. "Getting hungry," I asked her. "F... I am starved." "See you're learning." "You weren't serious about spanking me were you?" "Absolutely... bare bottom and all," I said smiling. "Have you seen my butt? You'd break your hand on it." "Then I guess I would have to wear leather gloves to protect myself." "You are so silly! I don't know why I do it..." her tone shifting suddenly. "That's what I am here for. Whatever you say or do remains in confidence." "Do...?" "Done... the drug smoking stays between us; but that doesn't mean you can continue that habit that ends today. It would break your parent's collective hearts if they knew about that and you know it." "Yeah and you'd have to stand in line to beat my butt..." "Take a number..." I said joking; "now serving number three for swatting Amber's backside." "That's not funny... dad would whip out the belt with no hesitation." Click! A piece just fell into place. "I'm sorry I didn't know..." "I shouldn't have said anything." "Yes you should... how about pizza we can stop and we can use the bathroom?" "I love pizza..." We stopped and ordered a large pizza, relieved our bladders and sat opposite each other in silence. I let her have her quiet time while I pondered my next course of action. My gut told me that tomorrow I would be receiving a phone call from her school and I would once again have to intervene and this time with greater consequences. "You look deep in thought Uncle Ted," Amber had returned my 'uncle' title to me. "Yeah... just worried sick," I told her. "About me," she asked. "Yeah, I have never had kids and you are the closest thing I have to a daughter. I was there when you were born, took your first steps and all those other great milestones; and I am here for this one too sadly." "Uncle Ted this isn't your fault... I am the one making all these decisions. Good or bad this is my life to lead." "That's the most grown up thing you have said today." "I guess it is..." The pizza arrived and we dug in and joked and made small talk while Amber made her decisions. I just had to be patient and see what the outcome was going to be. I hate waiting! We refilled our sodas and headed back out onto the highway. We still had a few hours before I dropped her off at home. "Do you have a destination in mind Uncle Ted," Amber asked. "No... we are just out to see where the road will take us." "Very philosophical of you," she remarked. "Hey, it's what I do." For the next two hours we talked, listened to the radio and enjoyed the snow covered landscape. We arrived at her father's house right at two o'clock and I let her out. "Remember our deal I don't want to see you tomorrow but I will if I have to." "Okay Uncle Ted... I promise." At three minutes after nine o'clock the following morning my cell phone rang, it was Amber's school. I told them I would be there as soon as I could. I went to Erika's office and explained that business from yesterday had not been finished and she waved me away with a smile, I was not smiling. I cursed under my breath the entire drive to the academy. Cheryl the guard was waiting for me with Amber standing next to her. "I'll take it from here," I told Cheryl. "Good luck... she is suspended until we get word from you that she can come back." "Her father," I asked and Cheryl nodded. "Okay Amber, get in the car... now." With backpack brimming with her personal belongings she obeyed. She flung the backpack into the rear seat and sat in the passenger side brooding. My door slammed shut and I buckled up and drove directly to my home in silence. I parked and opened her door and pointed to the front door afraid to speak until we were inside. The front door closed behind us and my temper got the better of me. "What the hell happened?" "What do you mean," she asked. "I mean, what happened to your promise?" "You didn't really believe me did you?" "Yes I did Amber... I took you at your word but obviously you didn't take me at mine." "Oh come on... I knew you weren't serious..." "Drop 'em..." I said cutting her off. "What?" "I said drop 'em... lose the slacks and assume the position over the arm of that chair," I said pointing to the closest leather recliner. "You are not going to spank me..." but before she could finish that thought I grabbed her by the waist, bent her over the chair's arm and began undoing her slacks. "Have you lost your fucking mind?" I didn't answer her as she lost the fight to keep her slacks up and I was not shocked to see the black t-bar she was wearing underneath. "School dress code," I asked. "No... please Uncle Ted..." but her pleas fell on deaf ears. "Well the butt floss will make my job easier; I don't have to yank down panties to get at your ass cheeks you little liar." "Liar, what are you talking about?" "Your butt... you lied about it." "..." "Doesn't matter it's still getting spanked." She tried to cover her ass cheeks but I pinned both of her hands in one of mine and began to swat away. Crack! The sound that my open palm made on her cheek was loud and sweet. Amber howled as the flesh began to take on a ruddy color. Crack! The other cheek blossomed red and soon after a dozen or so strikes on both cheeks tears were flowing and her ass never looked better. I could see that her t-bar was absolutely soaked once I took time to examine my handiwork. I ran a finger along the material and she nearly jumped out of her skin. "Uncle Ted, what are you doing?" "I am checking to see if you pissed yourself or..." I sniffed my finger and it definitely didn't smell like urine; Amber's pussy was completely soaked. "Did you cum," I asked her softly. "What..." "I asked you a question young lady, did you climax while I was spanking your ass?" "Yes..." "Why..." "Why what," she said half moaning half crying. "Why did you cum while I spanked you?" "I get off on pain god damn you!" she roared at me. I gripped the sliver of material between her butt cheeks and pulled upward... hard! The effect was immediate and dramatic; I watched her face contort into a mask of pure pleasure as she came again. "You like that?" "Yes..." she whispered. "I asked you a question," I said as I slid two fingers deep into her pussy. "YES!" she howled as her pussy gripped my fingers like a vice. "You want your pussy punished too don't you?" "YES!" "Get undressed Amber... let me see that young body of yours." Without a word I extracted my fingers and she stood up and turned to face me. Her face was streaked with tears and she took off her sweater with the school crest and tossed it to the floor. Next she slowly unbuttoned her white blouse and it I learned she wore no bra and her large firm breasts were topped with rock hard nipples. The blouse landed on top of the sweater; she kicked off her shoes and stepped out of her slacks and stood there in all her naked glory. I examined her and saw that her pussy needed to be shaved before we went any further. "Follow me to the bathroom... that pussy of yours needs some serious attention." She shadowed me to the bathroom and sat on the toilet as I directed. I ran warm water and lathered up the gnarly patch of pubic hair and held up a brand new razor. "Spread your legs for me Amber." "Yes Uncle Ted." She opened them for me and I knelt before her and made the first stroke along her furry mound revealing skin free from hair. I rinsed the blade and once more ran the razor over her pubic area clearing more and more smooth skin. I could see from my vantage point her glistening sex as it lubricated itself in preparation for a fierce fucking. At last her pussy was as bare as it could be and when I looked up into her eyes the lust there was barely contained. "You know where my bedroom is..." "Yes Uncle Ted." "Go climb up on it... be on your hands and knees with your ass right at the edge of the bed." Without another word she stood and walked away. I rose, cleaned off the razor and emptied the sink before following her. I stood before the bed and there was Amber head down and ass up waiting for me. I stripped down and my cock was pointing straight away from my body eager to be plunged into her tight depths. I walked up to her and took cock in hand and began teasing her pussy lips with the head and she moaned and groaned at being denied. I promised to punish her pussy and I would. I let the head slide between her pussy lips and then without warning rammed my hips forward burying the entire length into her. Amber cried out but not in pain but in bliss as her pussy gripped me in an orgasmic fist. I guess the waiting did its work after all. She had barely recovered when I grabbed her by the hips and started thrusting into her as hard and deep as I could. She was grunting in time with my movements and short of Diane's virginal pussy this was the tightest thing I had felt in many years. I thought about fighting back my orgasm but thought fuck it I had her to myself for the entire day. When I was done with her she would be walking funny and begging me to stop. I adjusted my pace and slowed a bit but thrust all the harder ramming with all the power I could manage. After a few minutes of this Amber was screaming into a pillow as her third orgasm crashed over her. I felt my toes begin to curl and so did she as Amber started to thrust her hips back at me driving me headlong into my first climax of the day. When I was close I pulled out and came all over her back and ass. She collapsed onto the bed a panting mass of girl flesh.