Anne Greesley

I wasn’t really paying any attention to what Mr. Greensward was saying. I was checking out his bulge, trying to picture what he had going on inside those khaki pants. Whatever he had going on in there, I bet it was pretty nice, and I bet I’d love to get my hands on it!

Mr, Greensward was the best teacher in the school. He was smart, kind, funny, patient, and hot as fuck. I had a crush on him. All the girls in my class had a crush on him. Hell, half the boys probably did too.

I hadn’t even realized that he had called on me. “Um, I’m sorry Mr. Greensward. I wasn’t paying attention.”

He smiled. My face flushed red and my nipples stiffened. “That’s ok. Anne, how about you? Can you explain to the class the significance of the Comstock Act of 1873?”

Anne smiled nastily. She was blonde, and was prettier, and had bigger boobs, than me. And she’d been paying attention. “Well, it prohibited the Post Office from mailing obscene, lewd, or lascivious items…” she simpered. She actually fucking simpered. The bitch.

After the final bell rang, I stopped by Mr. Greensward’s classroom. He was sitting behind his desk, going through a stack of papers. He looked adorable there, with his reading glasses on. I tapped lightly on the door and stepped into the room. He barely looked up.

“Mister G,” I felt my face going all red again, “I wanted to apologize for not paying attention today in class. You’re such a good teacher, and I really admire you and I want to do good work for you….” I trailed off stupidly.

He finally looked up from his papers. He peered over his glasses and looked at me for a long minute.

“So what you’re saying,” he said at last, “Is that you want to suck my dick?”

I couldn’t believe he had just said that. I mean, he had said it very slowly and clearly, enunciating every word. But I still couldn’t process what it meant. I must have hallucinated it, some weird horny Freudian mindslip.

“Wha- What?” I stammered.

He took his glasses off and huffed with exasperated annoyance. “I think you heard me just fine Miss. Unless your deaf as well as stupid and ugly? Show me your tits!”

Oh my God. I felt like I was dying of humiliation. And my cunt was instantly soaked. I felt his eyes burning into me, practically searing my flesh, as I unbuttoned my blouse and wriggled out of my bra.

“Huh. Not too bad, I guess.” Really? I was proud of my boobs. They weren’t huge, but I thought they were pretty nice, one of my better features. “You should look into getting them enlarged. Now do you want to suck my cock or not? I don’t have all day. I have a date later on, so get to it.”

He pushed back his chair and stood up, undoing his belt and letting his trousers and underwear drop. His cock dangled thickly in my face.

It was the first one I’d ever seen, in person anyway, not in porn, and I thought it looked delicious! I wasn’t entirely sure how to go about it, but I couldn’t wait to get that thing into my mouth.

“Jesus Christ,” Mr. Greensward snapped. “Sometime today please? I told you I’m busy. And someone could walk in at any time, you don’t want to get caught with a dick in your mouth, do you slut?”

This was so very not the kind, patient Mr. Greensward I knew from class. But holy shit, it made me hot.

I got down on my knees, my breasts hanging out like a pair of udders, and started in. I did my best: kissing and licking all up and down his thick, sweat-salty penis, and I was quickly rewarded as it stiffened and grew, standing straight up like a spear. It wasn’t as big as the one’s I’d seen in porn, but I thought it was plenty big. And beautiful too, with a big purple crown straining eagerly at my lips.

I opened my mouth and tried to swallow him whole. There was way too much of him. He grabbed me by the hair and shoved my head down on his cock, and I choked, gagging and struggling. I couldn’t breathe, and I panicked. When he finally relented, I threw up a little.

“Oh for fuck’s sake,” Mr. Greensward said, sounding disgusted. “Really, that’s the best you can do? I thought a skank like you would know how to suck dick properly. Stay like that, I’m just going to jerk off into your mouth.

I knelt before him, like a girl about to receive communion, tits out and mouth wide open, tongue extended, as he jerked his big cock inches from my face. His big fat balls jiggled in time. I don’t think I’d ever been so turned on! When he finally came, he missed my mouth entirely, spraying semen all over my face where it got into my eyes and stung.

He was already zipping up. “You need to work on that. C minus, at best. Practice sucking your dildo.” he looked at me. “You don’t have one? God you’re pathetic. Get one. That’s your homework. Get one, and learn to suck it properly.”

“Yes sir.”

“My house. Wednesday, 8pm. Don’t fucking be late.” He picked up his papers and left me there, still kneeling topless by his desk, face covered in sticky bitter white semen, shaking with shock, frustration, and lust.

*
In class the next day, Mr. Greensward was normal as fuck. Kind, patient, smart. I almost couldn’t bear to look at him. He called on me though, and for once I had been paying attention, and I knew the answer. Anne Greesley gave me a look full of searing hatred. Mr. Greensward smiled, and I felt my pussy gush in response.

The sex toy store was super creepy and smelled like bleach, and it felt like everyone in it was staring at me. I selected the least enormous dildo they had, and paid for it in cash. “Have fun,” the clerk smirked.

I didn’t even try putting it in my pussy (though I will admit I was tempted), but by Wednesday evening, I felt a little more confident about having a phallus in my mouth.

When I arrived at Mr. Greensward’s house, right at eight, the front door was open a crack, so knocked and went in.

He was sitting on a stool at his kitchen island doing something with a precision scale, filling little plastic bags with white powder.

I’m not stupid. I kept my mouth shut tight.

He barely even looked up. “Living room. Big fucking stack of papers, need grading. Red pen in the drawer.”

“Yes, Mr. Gr—”

He cut me off, still not even looking in my direction. “And make sure Anne Greesley gets an A. She deserves it. She’s way smarter than you.”

For the next hour and a half, I discovered the tedium that is grading papers. I used the red pen liberally. Gave myself an A, because fuck you Mr. Greensward. I gave Anne an A-, though by all rights it would have been a C+ paper. At best.

Finally, Mr. Greensward came in. He was wearing jeans and a white undershirt, and he looked good enough to eat.

“Jesus, took you long enough.” he wiped his nose. “Get your clothes off.”

I felt incredibly self conscious undressing as he stood, silently watching me. I pulled off my shirt, unhooked my bra, slid my bra and panties down as he observed.

“Huh, could be worse I guess,” he said. “Obviously you need to lose some weight. Get those tits worked on. And for fuck’s sake, shave your cunt. That’s disgusting. You know, there’s a surgical procedure they do, labia tucks. You should look into that.”

For all that though, I could see his dick straining inside his jeans. So at least I was doing something right.

“So do you want to suck my dick, or what?”

“Yes!” I exclaimed eagerly, “I’ve been practicing and everything!”

He slapped me hard across the face. “You want it? Beg for it, skank!”

It took me a minute or two to be able to speak. My left cheek felt like it was on fire, and tears streamed from my eyes. I gathered my self together, knelt down “Please sir, please be kind enough to let me suck your big beautiful dick, Sir!”

He grabbed me by the nose and twisted, hard. I screamed and struggled, but he was merciless. I saw stars, white lights dancing in front of my eyes. “Like you fucking mean it, cunt!”

When he finally let go, I was sobbing. I could taste the tangy iron of the blood running out of my nostrils and into my mouth. I grovelled on the floor in front of him. “Please, please Sir, please let me suck it,” I begged, meaning every single word with all my being. “You have the most beautiful cock sir, please let me take it in your mouth, I’ll make you feel so good! You won’t regret it, I promise!”

He unbuttoned his jeans and sat down on the couch, he dick pointing straight up at the ceiling. I wasn’t lying: it was a thing of beauty, and I did want it, very badly.

“DON’T get blood on my couch!” he barked, “wipe your fucking nose!”

My nose was extremely tender and felt swollen. My face still smarted from his open-hand slap. I got most of the blood off with a kleenex. Then I got down on my knees and got serious about worshiping his cock.

I’d watched a lot of blowjob porn with my new dildo over the last couple days. I started slow, kissing it tenderly, from the purple crown, down the underside, along the thick vein, down to his pendulous ball sac.

He rolled over onto his side. “My ass,” he commanded. When I hesitated, he grabbed a fistful of my hair and yanked hard.

It wasn’t that I was hesitant to do it, I just hadn’t really understood what he wanted. Now I knew. He held his butt cheeks wide open for me as I licked and kissed all around his puckered anus, tasting the earthy, maleness, teasing my tongue into the tight star of his opening. I was in heaven. He certainly seemed to be enjoying it as well. Finally though, he pushed me away and rolled over, shoving his erection in my face.

“Now suck it bitch, suck it like you mean it!”

This time I was ready. I took hold of the shaft in one hand, so I could control the depth and jerk him off at the same time. I opened my mouth wide and swallowed him, taking about a third of his length into my mouth, as much as I could without gagging. I swirled my tongue all around the crown, concentrating on the underside, just below the tip, that sensitive spot where the two lobes of the head met. My hand never stopped moving.

“Finger my ass!” he moaned. He moaned!! I felt a flush of pride! I was doing it right! With my free hand I reached around and pressed my finger into his wet asshole.

He started furiously humping my face. I was all I could do not to choke on his cock, but he was already coming.

“Oh fuck yes! Anne, you filthy little cocksucker!” I felt his penis swell and squirt, and suddenly my mouth was flooded with viscous salty-bitter semen. I stayed with him, swallowing every drop as his cock slowly softened, and his thrusting became less urgent. Finally, his much reduced penis fell out of my mouth with a plop.

Despite myself, I grinned.

“Not too bad,” he grunted. “Needs work. Make me last longer next time.” He was pulling up his pants, tucking his delicious cock away out of sight.

“Listen,” he said. “I have a job for you. It’s pretty simple, I don’t think even you can fuck it up. Take this package,” he handed me a small cardboard box, wrapped in brown paper and taped shut, “Over to Ms. Manly’s house. Here’s the address. She’ll give you an envelope. Bring it back to me. Don’t fuck around.”

I took the box from him.

“Well get dressed! Get the fuck out of here! Sheesh, while we’re still young?!”

“Oh,” he added when I was clothed again and headed out his front door. My nose had started to bleed again, just a trickle, and I could still taste his semen in my mouth. “After you get the envelope, ask her if there’s anything else you can do for her. Don’t forget. And don’t take too long coming back here!”

**

Ms. Manly was our math teacher. She was tall, skinny, gray-haired, and rather severe. For all that, she was a pretty good teacher. She was strict, but not mean. If I hadn’t hated algebra so much, I might even have liked her.

Her house wasn’t far, five or six blocks. It had gotten dark and it was cold out. I didn’t have a coat, and the cold breeze made my eyes cry. The stars were bright and beautiful in the sky above me.

I nervously rang the doorbell when I got to Ms, Manly’s place. A long moment later she answered the door, dressed in a black silk kimono and bunny slippers. She raised an eyebrow archly at me.

“Oh, you must be Ted’s new girl. Huh, you’re not really his usual type. Come in, come in! You must be freezing!”

She looked different out of the classroom. Not just the clothes. She seemed warmer, less severe. Her hair was down, a cascade of grey curls. She was, I realized belatedly, quite pretty.

I handed her the package, and she gave me a fat, sealed envelope off her coffee table.

There was a brief, awkward silence. We both spoke at the same time.

“I should go,” I said. “Can I get you something to drink?” she asked. We both laughed nervously.

Then I remembered what Mr. Greensward had said.

“Is there anything else I can do for you Ms. Manly?”

She paused. “Why yes, I think there is. And when you’re here, call me Mary.”

I followed her into her bedroom. I’d seen enough porn to have a pretty good idea what she had in mind. Sure enough, there was a porn playing on the big flatscreen next to her bed. Two heavily muscled naked black guys were wrestling and making out. There was a large, iridescent green and blue vibrator or dildo shaped vaguely like a cuttlefish on the sheets, and a large plastic bin full of sex toys next to the bed. She stepped out of the bunny slippers and let the kimono fall to the floor.

I’m not very good at guessing ages: she must have been… 40? 50? Anyway, she was lithe and slender with just a little belly, perfectly shaped small boobs, and her graying pubic hair was shaped like an exclamation point. Her eyes flashed mischievously.

She lay down on the bed, slipping a pillow under her butt and spreading her legs wide. Her pussy was wet, swollen, slick and excited. Her clit bulged out eagerly. “Take off your shirt,” she said. “I want to see your tits.”

I did as instructed, feeling only a little self-conscious about her ogling my bare chest, and I eagerly climbed onto the bed and in between her thighs.

I may not have known much about sucking cock, but this was an area where I had some practice and expertise. In my little circle of friends, I was known as The Champ.

As much as I wanted to dive in and bury my face in her wet pussy, I resisted. I slipped both hands under her ass, and ran the tip of my tongue up, down, all around the outside of her drooling pussy, making her moan in an incredibly satisfying way.

“Lick it, you tease! Please, please, please lick it!”

That’s what I wanted to hear! Her cunt was drenched, absolutely sopping wet. I flicked my tongue against her swollen clit, licking it lick a kitten lapping up milk. I let my fingers explore inside her pussy, finger fucking her. I let a fingertip brush against her asshole, and she groaned loudly, arching her back, so I indulged her and let it slip up inside her tight hole. All the while I kept flicking the tip of my tongue up against her clitoris, steady as a metronome. I couldn’t breathe, but that was OK. I could tell this wasn’t going to take long.

“Oh… oh… oh… oh…!”

My fingers were moving inside her ass and her cunt, my tongue kept flicking at her clit. I needed air, but I knew she was right on the edge.

“Oh, FUCK!!!”

She came hard, squeezing my head between her strong thighs, mashing her vulva up against my face, hands convulsing in my hair. I couldn’t believe how wet she was, it was all over my face!

When she finally released me, she was silent, breathing hard as if stunned. On the screen, the two black guys were furiously butt-fucking. It was pretty hot. I realized that, between one thing and another this evening, I was pretty fucking wet myself.

After we had both caught our breath, Ms. Manly sat up on her elbows. She looked almost as if she were… blushing? “That was amazing!” she said. “Would you like me to reciprocate?”

I did. I really did. And I thought I had seen a dildo attached to a harness in her bin of toys, and I was very interested to learn more about that. But then I thought of Mr. Greensward, waiting impatiently for me back at his house.

“Maybe next time,” I said.

*
Back at Mr. Greensward’s house, he was busy grading papers, a task he swiftly unloaded on me. He took Ms. Manly’s envelope without comment.

“So,” he said when I brought him the stack of freshly graded papers, pathetically eager to please. “I suppose you want me to fuck you?

I nodded. Oh boy, did I ever!

“I’ll do it,” he said. “If you can get me Anne Greesley’s phone number.”

Well, it just so happened that I had her number in my contacts.

He took it, and sent a text. We went to his bedroom. His bed had red sateen sheets, and there was a lava lamp on the bedside table.

“Disrobe.”

I did what he said.

“I thought I told you to shave that thing. Ugh, lay down on the bed. I’m gonna need a snort for this. Don’t move.”

I tried to stay still, but I was all aquiver. My clit felt like an overinflated balloon ready to burst, and could tell my pussy was really really wet. I was about to lose my cherry, and the man soon to be taking my V-card was none other than Mr. Greensward! I couldn’t decide which version of him turned me on more: the kind, patient man I knew from class, or the sneering, snide, abusive guy he was after school.

He came back into the bedroom, naked, wiping his nose. He was naked, and his cock jutted out like a spear.

“P-please be gentle,” I said.

He barked like a hyena. “Gentle? Gentle? You fucking little skank, you’ve fucked all the guys at school already, half of the teachers too. Fuck no, I’m not going to be gentle!”

He rolled a condom onto his cock. “Spread your legs. Wider. Wider. That’s it. Ready? Get ready!”

I was so very ready! He skewered me with on brutal thrust. It hurt, but not as much as I’d expected. Once he was all the way inside, I felt so full, so complete, so incredibly sexy. I wrapped my legs around his back as he humped me.

I could almost have come that way. Almost, but not quite. He didn’t last very long, which was probably for the best, because my poor tender pussy was not used to this kind of a workout.

Grunting “You slut, you fucking worthless little slut,” I felt him twitch as he came. I felt a surge of emotion as he pulled his cock out of me, leaving me hollow and empty.

He rolled the condom off and held it up over my open mouth. “Drink,” he commanded, and I did, savoring the salty-bitter semen that dribbled onto my tongue.

I realized that I was weeping. It wasn’t that I was sad, or even upset really; actually I was still super turned-on. I think it was just the enormity of the emotion washing over me.

“If you’re going to cry, do it the fuck outside!” he bundled me naked out his door into the cold night, and tossed my clothes in a wad after me, slamming the door.

I got dressed and made my way home, where I masturbated in the comfort of my own bed. I would masturbate to that night for years to come.

*
He was still the same Mr. Greensward in class: kind, gentle, patient, funny. It really threw me for a loop, I couldn’t quite wrap my head around him. And yet, between my thighs, my sore and battered pussy drooled. I wanted him.

As I gathered my things at the end of class, he called me up to his desk.

“My house. Eight O’clock.” I was dismissed.

When I arrived at his place, promptly at eight, something felt different. The door was open a crack, so I went right in. I heard noises from the bedroom.

Anne Greesley was sitting on the edge of his bed, those slippery red sateen sheets, wearing nothing but a black lacy bra and matching thong panties. She had her hands on Mr. Greensward’s ass, and a mouthful of his cock.

He looked over at me, and grinned.

“Now this is how you suck cock! Take notes, skank, you might learn something useful.” he caressed Anne’s long blonde hair. “Mmm, don’t make me come yet babe. I want to fuck your sweet little pussy. And then we’re gonna fuck this one up the ass.”

Anne came up for air, drooling. She looked at me, gloating, with the nastiest, meanest smile I’ve ever seen in my life. “Doesn’t he have the yummiest cock ever?” she simpered. She unhooked her bra, setting her big breasts free, cupping them in her hands to display them for the benefit of me and Mr. Greensward. They really were pretty nice.

I had a sudden vision of her, aged forty or so, with tired, fried hair, wrinkles on her face, bad cosmetic surgery, and sagging tits. It wasn’t hard to picture.

“I need a snort,” Mr. Greensward said. “You, get Anne nice and wet and slippery for me. You know what to do, slut. But don’t make her come! I’ll be right back.”

Yeah, I knew what to do. And no, I wasn’t about to make her come.”

Grinning wickedly, Anne pulled off her skimpy panties and lay back on the bed. Her pussy was shaved bare, and was already pretty wet.

I did as I was told, crawling in between Anne’s spread thighs and licking her juicy twat. As soon as I was down there, she grabbed a handful of my hair and pulled hard, jamming my face into her cunt. Fortunately I had taken a big breath of air. She was really fucking wet. I licked her pussy, doing my best to avoid her clit. Despite myself I was getting extremely turned on. Mr. Greensward was going to fuck my ass!

“She’s not doing it right,” Anne whined. “She’s doing it wrong on purpose!”

“Stupid cunt!” Mr. Greensward grabbed a fistful of my hair and yanked me bodily off the bed. I fell sprawling onto his bedroom floor as he climbed onto the bed where Anne was waiting eagerly for him, fingering her extremely wet pussy in eager anticipation. “Watch this!”

He slid his cock up inside her, and she cooed. I swear to God, she cooed, leering at me and sticking her tongue out.

It was really sexy to watch, like porn only in person. His big hard dick, covered in her pussy juice, sliding in and out. She squealed fakely with every thrust, her feet up in the air, wiggling her toes.

I noticed Mr. Greensward’s wallet sitting on the dresser. Turning away from their vigorous fornication, I opened it up and extracted his ATM card, and left them to finish what they were doing.

Down at the bank, I guessed his PIN in one try: ANNE = 2663. I checked the balance in his checking account, and saw more money there than I had even imagined possible. Certainly way more money than any teacher should have in the bank. The guy was literally a millionaire.

Feeling like a sneak thief, I took the maximum amount possible out and stuffed it in my pants pocket. It was more money than I’d ever had in my life. I walked back to Mr. Greensward’s place, planning to put the card back where I’d found it, and hopefully to lose the virginity of my asshole.

When I got to his block, there were flashing blue and red lights everywhere. His house was surrounded by cop cars. There was even a helicopter, and a news crew.

I turned around and walked off into the night. I was still horny. I wondered if Ms. Manly was home.

END

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