October, 2003

As soon as the words left my mouth, I knew I'd blown it. For a moment, the young woman across the desk sat in stunned silence. She looked around nervously, the relief evident in her face that we were alone, although I am sure that at the moment that thought also scared her to death.

"What?" Her voice was soft, plaintive, clearly disbelieving what her ears had heard. I buried my head in my hands, unable to face her any longer.

Honestly, I couldn't believe I'd done it again. It had been close to twenty years since I had last propositioned a student in exchange for a better grade, but apparently the old kinks were still there. Buried away for nearly two decades, but still ready to pop up at a moment's notice. I knew this would be the last time. It had to be. I was fifty years old and running out of options.

Katie looked as if she wanted to turn and run from my office at the first opportunity, and I could feel the blood rush to my head, my cheeks turning crimson, my face warm in my hands. I glanced up, silently watching her fidget uncomfortably in her seat.

She looked down to her lap where her hands were efficiently twisting a tissue into tiny knots. Wanting to do whatever it took to make her forget, I froze. No words came and I could feel my breath coming in short gasps as my heart rate continued elevating.

I wanted to get up, to comfort her, but knew that was no longer an option. I had crossed the line in the sand, the boundary no teacher should ever cross. My only place now was on the carpeted floor of my office, kneeling in front of her, begging for her forgiveness. But my cock was still painfully hard in my slacks and I knew my arousal would be obvious once I stood, so I remained seated, hidden behind my desk.

I bowed my head, waiting for Katie to leave, and silently shook as I heard her stand. I imagined her heart-shaped ass poured into the tightest pair of black leather pants I had seen in many years, knowing she would be heading directly to the dean's office.

Waiting for the sound of her hand on the door knob, I sighed, closing my eyes. I wondered how long it would take to clean out my office once I had been fired. I began making a mental list of people to call and things to do in preparation for finding another job.

September, 1973

My teaching career had begun innocently enough. Thirty years ago, as a young college graduate, I had been fortunate enough to receive a commission teaching middle school music. At the time, I was deeply involved in a relationship with my girlfriend, Betty, whom I'd met our first year at the university.

Betty had also been an education major, focusing on history and political science. As life sometimes goes, she was unable to get a job teaching and for many years ran a before- and after-school daycare program for latch-key children. It was one of the first of its kind in the state and served as a model for many later programs.

Our differing schedules meant the two of us saw little of each other and we quickly grew distant. The love we felt was still there but with no time to show it, things fell apart. We separated two years after college.

I had never enjoyed living the life of a playboy and I quickly reverted to my pre-college habits-a clean apartment, an immaculate reputation, and a filthy mind. One of my favorite discoveries during the mid 1970s was a small adult bookstore run by the father of one of my students.

Having decided weeks before to begin an early morning exercise regimen, I was that Saturday walking in a part of town I rarely frequented. I was leaning against a storefront catching my breath when, to my surprise, I saw Mr. Harrison, the father of little Mary from one of my classes, hurrying toward me.

"I'm sorry I'm opening so late this morning," he called out as he approached. Confused, I looked around me for the first time. The nondescript building I had been leaning against appeared to be abandoned at first glance. Looking closer, I saw this was clearly not so, judging by the industrial-strength bars on the windows and dead bolt lock on the door. Mr. Harrison pulled a set of keys from his coat pocket and quickly unlocked the door. "Come on in," he said, waving me ahead.

"Oh... I wasn't here for your store," I started, by way of explanation. "I was getting a little exercise and stopped for a moment. Sorry."

"Not a problem."

"What kind of store is this, anyway?" I was curious. We certainly weren't in the best part of town, and certainly not in an area that got much traffic.

"Ah... I run an adult shop," he answered. "Sorry. I thought you knew. Forget I mentioned it."

"Nonsense. I'm an adult. I know about places like these." I hated sounding so naive, but I had to admit I'd always been a bit curious about such things. For some reason I'd always managed to date the purest and most unimaginative women possible.

Missionary position only.

No sex with the lights on.

Boring.

I knew there was a whole other world of sexual discovery and deviance out there. My previous girlfriends had left me wondering what it was all about. "I suppose it wouldn't hurt if I took a look around."

Mike ducked through the door ahead of me and walked to the back of the store to turn on the lights. Alone, I wandered through the store, amazed at the variety of offerings on display. Films, magazines, books, toys, things I'd never imagined I would see.

Looking through what appeared to be a coffee table book devoted to bondage and leather, I found myself becoming powerfully aroused, my cock thickening and tenting the front of my sweat pants. Knowing there was no way I could purchase the book in the condition I found myself in, I quickly fled the shop, taking the book with me.

I was embarrassed at my unplanned theft and walked home in a rush, acutely aware of the book I held in my hand and the lurid imagery within it. I entered my home, hurriedly locked the door, shed my shoes and jacket, and headed for the living room.

I sat on the couch and began flipping through the pages of the book, spending a great deal of time on each photograph. Even in my most fevered fantasies, I had never imagined such filth. Women bound and gagged, fucked apparently against their will, pierced nipples connected with thin ropes of chain.

And leather.

I'd never considered leather to be a turn on, but seeing the tight crotchless pants, cock rings, and fringed chaps, not to mention the multitude of whips and riding crops, soon had my cock quivering with excitement and dripping with lust.

I found my gaze locked on one image in particular. Pictured were three people, two women and one man.

The man was nearly nude, wearing only a leather mask, featureless except for two eye holes and a zipper where the mouth should be. His arms were bound above his head, his forearms held together with a wrapping of leather cord. He was tied to something high enough to force him to stand on his toes, his legs spread wide by a large bar of iron shackled to his ankles.

Behind him was one of the women. She was fully dressed in what appeared to be a business suit. Hair pulled back in a bun and a pair of glasses completed the impression of a librarian or a school teacher. The image quickly proved false, as I saw her left hand pushed under the skirt of the suit. I could see her panties bunched around her ankles and imagined her fingers busy in her cunt. Her other hand held what appeared to be a leather dildo that was buried halfway up the man's anus.

I had never before thought of my ass as a possibility for pleasure. To my surprise, my cock lurched at the thought and I found myself loosening the drawstring, pushing my sweats to the floor, releasing my turgid shaft. Stroking lightly, I returned my attention to the third woman in the photograph.

She was completely naked and kneeling before the hooded man, his erection forcing its way down her throat. Her pendulous breasts hung low in front of her, nearly touching her thighs. The nipples of her breasts had been pierced and appeared to have some sort of clips attached. Her nipples were greatly distended, causing a look of pain on her face. The woman's hands were bound behind her back and wrapped with leather cord just as the man's forearms were.

Stroking my cock more rapidly, I could feel the tingling sensations in my balls steadily increase as I imagined the story behind the picture. The fully dressed woman was obviously in charge, unbound and unrestrained as she was. The idea that she might be a school teacher or librarian excited me and I could feel my orgasm slowly build toward release.

Who were the other two? Was the man her husband and the kneeling woman a friend? Another teacher? Perhaps a neighbor or maid? The woman in charge appeared to be a bit older than me. What if the others were her students?

The thought affected my arousal, driving my pulse faster and faster as I rapidly increased my stroking. I felt the veins on the bottom of my shaft, my hand a blur on my stiff shaft, the head fully engorged. Spreading my legs and leaning back against the couch, I laid the book down and began experimenting, still masturbating myself.

I wet a finger on my left hand, reached behind me, and carefully pushed against my resisting anus. Pushing harder, the tip of my finger popped through the tight opening and I felt the heat and tightness. I was emboldened by the new sensations and pressed deeper, finally burying my finger completely in my ass. Bumping into what I knew to be my prostate, I began twisting the finger gently as pleasurable sensations coursed through my body. My breath became ragged and I abandoned all thoughts, so intent was I for release.

I'd never felt my cock this hard before. The tight skin, coupled with the speed of my dry hand, made my stroking almost uncomfortable but to my surprise this only added to my pleasure. I thrust my hips rapidly against my tight fist as I felt the first signs of my impending orgasm.

I gasped as I erupted and my body froze as stream after stream of my sticky cum shot out the end of my cock. The world became fuzzy and almost black as my orgasm overcame me. I felt drops of sperm spray over my stomach and chest, a few reaching my face, and I gasped as a single drop landed on my upper lip, dripping into my mouth. I shuddered as I tasted my own semen, although more from the shock than from the salty taste. Panting, I lay on the couch for a moment, recovering from my exertions.

From that day forward, I was lost. Still unable to face the parent of one of my students, I began spending weekends out of town, visiting flea markets and bazaars, purchasing any kind of depraved smut I could get my hands on.

I still had no girlfriend, nor did the idea of one excite me any longer. A good date had become a quick meal followed by an evening spent poring over my growing collection of pornography. I didn't limit myself to any particular kink, enjoying instead a smorgasbord of smut. Incest stories, bondage, lesbian, water sports, all held a particular place in my heart.

Knowing I had to hide this from the school and community, I did everything I could to uphold my image as an upstanding teacher and mentor. Still, it came as a shock when the principal stuck her head in my classroom that sunny fall afternoon.

"Got a minute to talk?" It was not so much a request as a command. I shuddered, afraid I knew what this was about, but followed her to the office, imagining myself a little child trudging toward detention.

"I got a call from an upset parent over the weekend," she began, a grim look on her face. I knew then my teaching days were over. Every year I hosted a Halloween party at my home, inviting the entire faculty, as well as students and their parents. I was ever careful to keep my pornographic tendencies well-hidden, but this year something had gone horribly wrong.

"It seems one of the children decided to do a little exploring during the party. When Mrs. Janssen went to find her daughter, she was horrified to find the little girl leafing through this." She held up a small paperback, and I knew I was sunk. It was an erotic novel, poorly printed on cheap paper, but the title was easy enough to read. "School Girl Sluts," the front cover proclaimed. The drawing on the front depicted two junior high age girls with impossibly large breasts sucking off a pair of male teachers, their enormous cocks filling each tiny mouth.

I began shaking in my chair. Looking up at the principal, I saw only a stern look directed at me. "You will not return to school on Monday," she stated. I nodded... obviously I was done teaching here. "The family does not want to press charges and the school is anxious to avoid any further embarrassment more publicity could bring."

"I... I would never touch a student," I gasped, imagining a future in which I was raped daily in a prison shower. I knew I was no longer fighting for my job-that had been gone as soon as I walked in the office-but I wanted somehow to defend my character. She nodded slightly, giving nothing away.

No more words would come, so I simply nodded again. I stood, my shoulders slumped in defeat and slowly walked from the room. I swore to myself I would never again put myself in such a situation.

October, 2003

I hadn't heard Katie walk behind my desk, when suddenly I was jerked back to the present as I felt her soft hair brush against my cheek.

Opening one eye, I could see her pussy, tightly encased in black leather, and my cock gave a twitch, straining against my zipper, harder than it had been in years. I imagined that I could see the cleft of her cunt and wondered if she shaved.

Her right breast, covered by the soft pink fuzz of her sweater, pressed gently against my arm as she leaned closer. Pushing my own arm ever so slowly away from my side, I could feel the supple flesh of her tit, her diamond-hard nipple poking deliciously into my biceps.

I began to smell the unmistakable scent of aroused woman and, with that stimulus, felt my cock begin to leak copious amounts of pre-cum into my drawers. I knew a wet spot would quickly be forming on the front of my slacks and attempted to cover myself, weakly grinning as I grabbed that morning's paper and held it loosely in my lap.

Katie leaned closer against my side, whispering in my ear. "I want the 'A' for the semester, if that's okay?" She looked at me anxiously, equal parts fear and passion, waiting for my response.

My heart pounded in my chest. I quickly nodded, not trusting my voice to speak. A thin sheen of sweat had formed on my forehead and she quickly wiped her sleeve over my face, leaving the sweater damp and sticky.

Slowly she backed away from my chair and leaned against the desk, her hand playing idly with the firm tips of her breasts, still covered by her soft sweater. She gasped as I removed the newspaper, her breath catching in her throat, and she blushed. Looking behind her, she saw my office door still open. I had office hours for another twenty minutes.

"Do you want to close it?" I asked. She shook her head.

"I want you to close it." She grinned at me, eyes again dropping to my crotch, and she slowly licked her lips. "I want to see what I'm getting into," she whispered, her face flushed with excitement. "I mean... what's going to be getting into me."

I quickly stood, dropping the black and white newsprint to the floor, my erection tenting the front of my slacks and desperate to be freed. I stood and walked to the door. I glanced out in the hallway and saw no students waiting for me. I noticed only one office light on, at the far end of the hall. We would be alone.

I locked the door and returned to the desk feeling Katie's eyes on me the entire way, her gaze burning a hole wherever she looked. My cock was at full arousal and, as I returned to my chair, her tiny hand brushed against it, slowly stroking the thick shaft.

"Will it fit?" she asked, a bit of nervousness creeping back into her voice.

I nodded, knowing it would be no problem. "It will be fine."

I tried to sound reassuring, but the truth was, I was afraid of hurting her. Katie was a tiny slip of a girl. She couldn't have been an inch over five feet tall and weighed no more than 95 pounds dripping wet from the shower. Most of her weight seemed to be distributed between her tits and ample ass cheeks, but I had no doubt it would be painful for this tiny freshman trying to take my cock up her ass.

She nodded, seemingly relieved at my words, secure that it would be okay. Dropping her hands from her breasts, she turned away from me. I could hear the metal to metal rasp as she slowly unzipped her pants. Wiggling her hips seductively, she quickly pulled down the tight leather revealing a flimsy pair of silk panties.

I could smell her hot pussy more clearly now, her musky scent filling my nostrils. Breathing in her arousal, I watched as she tugged on her panties, slowly dropping them to the floor. Her ass was on display in front of me, pale white in the harsh fluorescent lights of my office, contrasting sharply with the golden tan of her legs.

I walked up to her and forced my hand between the cheeks of her ass. I dragged my fingers over the puckered rosebud of her anus and dipped down to the opening of her cunt. Even before I reached my destination, I could feel her juices coating the inside of her legs. Her heat was incredible and I felt myself almost sucked in as I reached the soft folds of her pussy.

As I explored her inner regions, I reached with my other hand and began stroking her outer lips. It appeared she shaved herself, as her entire pubic area was devoid of any hair, and I immediately found her clit peeking out from under its hood. Thrusting my fingers in and out of her sucking pussy, I felt her tense, then shudder, as a small orgasm rolled through her heaving cunt.

Realizing she needed no preliminaries, I toyed with her pendulous breasts with one hand, relishing the feelings as her slick walls clamped down on the invading digits of my other hand. For a moment, I thought of burying my cock in her dripping cunt, but held back. Maybe later. That wasn't what she had agreed to now. My quivering cock, still dripping with lust, had a different destination. She had said she wanted an "A," and I'd make sure she earned it.

Pushing slowly against the tight ring of her anus, I felt my cock strain, then move slowly past her sphincter. As it clamped down around the inflamed head of my prick, I heard Katie gasp. Gritting my teeth, I pushed forward.

April, 1982

After being discreetly fired from my position teaching junior high English, I had been fortunate enough to find another teaching job. A two year local college was considering expanding its course offerings and moving to a full, four-year liberal arts curriculum and found itself in need of a music department. Because of my quiet departure from my previous position, I found it ridiculously easy to get hired. I was in charge of the three college choirs in addition to two classes of beginning music theory and history.

It was a position far better than I'd dreamed of, even before being fired, and I felt incredibly fortunate to have it. For most of a decade I put all my extra energy into being the best teacher I could be and producing the best choirs. I liked to think I was doing good in the world, that my troubles were all behind me, but alas, it was not so.

It had been just after spring break when my new set of troubles began. Northern California has far fewer beaches than San Diego or Los Angeles, so golden tans are more often the product of a tanning salon than a day spent basking in the sun. When my classes started meeting in early April, I had a hard time concentrating on Bach and Beethoven, finding myself distracted by the sun-bleached hair and dark Coppertone tans.

It was a Friday afternoon, only six weeks before school was over for the year, when I heard a timid knock on my door. I looked at my watch and frowned. My office hours were clearly marked on the bulletin board outside my office and they had been over for more than an hour. I knew that many students were desperate for my help this time of year, so I stood and walked to the door.

I opened it and saw one of the young women from my music theory class. I couldn't place her name. In a freshman seminar class there are simply too many students to know each one personally.

"May I help you?"

The redheaded girl looked around nervously. "Can we go in your office?" she asked in a shaky voice.

"What can I help you with..."

"Stacey... Stacey Roberts"

"What can I help you with, Miss Roberts?"

She paused for a moment before suddenly blurting out her answer. "I'll do anything you want me to... for a good grade."

My head quickly swiveled around, hoping no one had heard what she'd said. It didn't appear anyone else was around this late in the day, especially before a weekend. I sighed with relief and motioned her into my office. I had no intention of actually doing anything with Stacey, but it wouldn't do to discuss matters in the hallway where anyone might walk by and hear us.

"Sit," I commanded, motioning a very nervous Stacey to a chair.

Sighing, I folded my hands and laid them on my desk. Stacey looked down, and seemed to be about to say something when I spoke. I needed to impress on this girl that her behavior was not appropriate, that there are certain things one should never do. I opened my mouth to speak. "How good a grade are you looking for?"

As soon as I said it, I wanted to retract it. I hadn't planned on saying it. I didn't want to say it. I didn't even know if I meant it. But I'd said it and it was too late to take it back. Even if I apologized at once, if Stacey so much as reported the incident, I'd be put immediately on probation and more than likely fired. I'd attained my tenure, but that doesn't help when sexual harassment charges are flying around.

Stacey also seemed surprised, her head snapping up, a mix of horror and excitement evident on her face. Suddenly, she became the aggressor. Standing, she slowly unbuttoned her blouse and pulled it open to reveal her smallish breasts covered with a pink satin bra. The material was thin, and I could see the bumps of her nipples pressing through the covering.

She reached behind her to unfasten the clasp, then paused. "If I let you see my tits, what does that get me?"

"Nothing," I answered. As soon as I'd sat down, I had reached for my grade book. Stacey was barely passing my class with a 65 percent average. Cleavage would get her nowhere.

Trying to cover her disappointment, she nevertheless opened the clasp and let the soft cups fall into her hands, revealing the pale white cones of her tits, pink nipples puckered with excitement. Her aureoles were large, giving a rounded appearance to the ends of her breasts.

Stacey dropped the bra to the ground and slowly twisted the tips of her breasts in her hands, causing blood to rush in, which further distended the nipples. It looked for all the world as if she had two Styrofoam cups plastered to her chest. "That gets you a 'C' at most," I said, wondering how far I could get her to go. "That's a far better grade than you have now." I looked at her over the tops of my glasses and she blushed. I think her embarrassment was less from standing topless in front of me than from failing my class.

"What else do you want me to do?" she asked, clearly having hoped that flashing her tits at me would be enough.

"Take off your skirt and panties," I told her, watching as she blushed even more brightly.

"I'm... I'm not wearing panties," she whispered.

"Hmm... someone's a naughty girl. Take off the skirt."

Slowly, Stacey unzipped the skirt in back, letting it fall around her feet, revealing her slim hips and fiery red pubic area. Her hands subconsciously moved to cover her nudity but I cleared my throat, looked pointedly at her, and they slowly dropped to her sides.

I motioned her closer, clearing a corner of my desk. Walking quickly to where I was sitting, she started to sit down facing me, but I again motioned with my hand, making it clear she was to lean over the desk, facing away from me.

Seeing her ready to argue, I quickly stopped her, pointing more forcefully at the desk. Sighing, Stacey bent at the waist, presenting me with her puckered asshole and pussy, still dry and tightly closed.

Reaching out one hand, I felt her body tense and heard Stacey gave a little squeak as my fingers brushed one smooth ass cheek.

"What does this get me?" she asked.

"We'll see," I replied, teasing my fingers through the lips of her pussy, noticeably more pronounced than when I had first seen them. "At least a 'B' though."

She nodded, seemingly pleased. As she pushed herself back against my fingers I found myself wondering how much an "A" really meant to this woman.

I found myself growing more aroused as I pushed my fingers deeper into Stacey's moist cunt. Continuing my in-and-out sawing motion with my left hand, I quickly unbuckled my belt and unbuttoned my slacks with the other. Shifting around in my chair, I somehow managed to get both my pants and underwear down around my knees.

My movements alerted Stacey to what I was doing and she turned and gazed at my erection, her face a mask of lust and desire. She shook her head from side to side. "Uh uh... if you fuck me I definitely get an 'A' in your class."

I thought about it, feeling my cock stiffen even more at her suggestion. I voiced my next idea somewhat nervously. "I can get laid anytime I want," I bluffed. It was a complete lie, I hadn't had sex since I broke up with my last girlfriend a few months earlier. "I want your ass." I heard her gasp, but it was true.

I'd never had anal sex before, but the thought of it always produced my best orgasms. I generally imagined the woman strapped to a chair or tied to a bed when I masturbated to that fantasy, but I would consider myself fortunate if this current gamble paid off. My drawer full of scarves and leather ties would have to wait.

I continued pumping my fingers in and out of her now dripping pussy, waiting for Stacey to say something. Finally she answered, her voice throaty and breathless. "You promise I'll get an 'A' for the semester." She seemed suspicious, well aware she would have no one to complain to if I didn't do as I said I would. No one other than the police, that is.

"Yes," I answered, feeling her thrust back against my hand, her pussy contracting and grabbing at my fingers as she neared her own orgasm.

"Fine," she answered. "But you have to be careful. I've never done it that way before... in the butt."

I smoothed a hand over her firm ass cheeks, reveling in the soft skin and firm musculature underneath, knowing that in a matter of moments I would be thrusting my cock in between them.

I stood, removed my pants completely, and moved in behind her. I felt Stacey tense as I drew near, but surprised her by shoving my cock into her pussy. Her entire body gave a huge spasm and she let out a small scream as I entered her.

"Oh fuck," she moaned, her chest heaving. She grabbed the corners of the desk for support, pushing her ass against me. "I thought you were going to do me... the other way."

"I'm going to," I said. "Be patient."

Knowing she would need a great deal of lubrication, I reached between our bodies to her sopping pussy and began transferring her juices to where they would do the most good. Slipping a finger past her tight sphincter, I pushed in again and again, each time working more of her slippery oils inside, all the while slowly stretching her anus.

"You feel so big in me now," she panted. "What's your cock going to feel like there?"

"Big," I answered, smiling. I thrust quickly in her pussy and felt her body shake as a small tremor flowed through her. I withdrew suddenly and watched as her pussy gaped open for a moment. I could clearly see the bright pink of her inner folds, but soon the outer lips closed shut.

I drew a finger over her lips again and collected one last bit of lubricant, smearing it over my already coated shaft, stroking myself to full hardness once more. Hunching forward, I placed the tip of my cock against her anus, pushing gently forward. "I'll go slow," I said, feeling her muscles tense beneath me. "You have to relax or it's going to hurt even more."

Stacey nodded. Obviously trying to do what I said, she slowed her breathing and I could see her asshole twitch as she tried to relax her internal muscles.

The change was remarkable and, without realizing it was happening, I found that the first inch of my cock had popped through the tight ring of her anus. It came as a surprise to her, too, as her tight sphincter quickly clamped down hard on my shaft, drawing a groan from me and a yelp of pain from Stacey.

Waiting for a moment, giving her time to get used to fighting her body's natural urge to force my cock out of her rectum, I gently kneaded the firm cheeks of her ass with my hands.

As I rubbed and squeezed, I heard Stacey give a quiet moan of pleasure. I felt something brush gently against the soft hair on my balls and realized she had reached underneath her body and was busily playing with her pussy, trying to gain any small amount of pleasure she could. Feeling her ass loosen once again, I shoved steadily forward, managing to bury half my length in her tight hole before she clamped down again.