Oops

Grading papers was a bitch. After reading the same grammatical error for the fifth time in as many essays, I had to step away from the daunting mountain that covered my kitchen table. Grabbing some wine from the kitchen, I crashed onto the couch. My eyelids grew heavy. The clock read 12:05am. Taking a swig from the bottle, a warmth washed over me. No glass necessary when you live alone. It might have been a shitty one bedroom in the middle of nowhere, but I at least lived alone.

I was 24 and had recently earned my degree, and with goals of being a university professor one day, I took the only teaching gig that would hire me. Turns out, that would be High School English in the smallest town I'd ever seen. I'll admit, it wasn't exactly what I had in mind, but I view it as humble beginnings for a long, successful career. In the meantime, I would teach bratty teenagers who couldn't care less about what I had to say. That attitude reflected clearly in their work. After nearly a full semester, I was exhausted.

There wasn't even a nearby bar to drink at. I did try to go to one place, but it wasn't a place for people like me, to put it nicely. And of course when I checked, there wasn't a guy around for miles on my dating apps. My hand had been pretty busy for the past few months. I took another drink. It stung all the way down, but it relieved some of the stress I'd been holding onto.

My eyes rolled into the back of my head, and my thoughts began to wander. I remembered this one time when I was at a bar in my college town; I was flirting with this guy all night. His name was Chris, and he had these stunning hazel eyes. He fucked me in his car, and I carried his load back inside. I hadn't been fucked in ages. My hole twitched to the memory.

Another drink of wine had me loosening up, and I found myself toying with the waistband of my underwear. I tried to recall exactly how it felt to be opened up like that. The pressure. The stretch. The pleasure. I was fully hard in seconds. The same hand that had been holding a red pen for hours on end was now wrapped around my sensitive cock. My skin was soft to the touch and sent tingles throughout my shaft. Fuck. Fuck me, Chris. Fuck me. Maybe it was the alcohol, because I knew better, but I downloaded that stupid app anyway. You know the one.

My profile was exactly as I had left it. My main photo was of me and a friend at the pool, but cropped so that it was only the neck down. I had been wearing my favorite speedo, and the angle captured my ass perfectly. I wasn't shy about showing it off. I never had been.

I glanced through my old nudes. The one that I was most proud of was one that an ex took. He had been going through a photography phase and used his professional camera to take it. I was posed on all fours with an arched back, naturally. In it, I was wearing this maroon jock strap that hugged me in just the right places. Both that jock strap and photo had gotten me laid many times over.

Knowing that there was no one around, I waited for the screen to load. I had checked the app several times over before giving up and deleting it. When the profiles began popping up, one at a time since my wifi was shit, I saw the same blank profiles as before. Just before I closed out, someone caught my attention, or at least my dick's attention; a shirtless torso I hadn't seen before.

I inspected further to see that there was virtually nothing filled out in his bio other than that he was a top. At that point, that was all I needed to know. I took another sip of wine and opened a message with him.

'Hey'

'Sup' The reply was almost immediate. Good sign.

'Not much. Just hanging at my place. You?'

'Looking for some ass' Usually, it was a turn off of mine to be so blunt about it. I liked to be seduced at least a little, but I felt my dick taking charge. I slid one hand down my pants to feel my hole. It was tight, and even the lightest touch made it ache for some use. I opened my album and sent him a couple photos; the full pool photo with my friend, and the only nude I'd need to send to get him over here.

'Like this one?' Waiting for a reply felt like ages.

'Mmmm, damn'

'You like?'

'You tell me' Shortly after that came his own picture. It was beautiful. Normally, I wouldn't like a nude where a guy's sitting on the toilet, but his cock more than made up for it, or maybe I was just really fucking horny. It was long, thick; his balls were a good size too. There was even a bit of hair that was just to my liking. I popped my finger a knuckle deep into my hole, and I tightened around it. This guy would wreck me.

'Fuck me, that's a nice dick'

'Don't mind if I do'

'What're you into?'

'I like to be in charge. Dom ig. Stuff like spanking, sloppy head, anon, etc.'

I audibly moaned. I sank my finger deeper into myself and even that felt like heaven. I typed with one hand as fast as my thumb could go.

'And you're real?'

He sent a live picture of that same torso with a thumbs up in it. I clenched around my digit and replied with a live picture of my hand reaching down towards my hole. I had been taken over by my sex drive and wine that I didn't need to know anymore details.

'Wanna come over?' The minutes felts like hours.

'Sure. What's you're address?'

After sending him my apartment complex and number, I told him to let himself in and that I'd be waiting for him in my bedroom. I didn't want to waste any time. With 15 minutes to his arrival, I tore off all my clothes and dug through my drawers until I found that maroon jock. I slipped it on and instantly felt sexier. I savored it as I checked myself out in the mirror. My dick did not want to be confined in the front pouch, but I managed.

I crawled onto my bed and set the wine bottle on the nightstand. I got on my hands and knees and dropped my face into a pillow, eliminating any and all sight. I felt so exposed with my ass facing the door, but it only served to turn me on further. My heart raced, having not had a hook up in such a long time. Hindsight is 20/20 though, as they say.

•••

Holy shit! I'm just laying in bed, jerking off like just about every other 19 year old does around midnight when my phone goes off. I'm not gonna lie, I thought the profile was a fake at first. Guys around here don't look like the picture he had on his profile, so I just entertained it a bit. But then, he sent the full picture and it turns out to be Mr. Matthews! My goddamn English teacher! I didn't know what to do. Should I even talk to him? Should I block him? The way he arched his ass taunted me, and I felt my dick begin to swell. I sent my own picture without thinking too hard about it.

Mr. Matthews was an asshole of a teacher. He's unnecessarily hard on us for no reason. He assigns "college-level" amounts of homework even though we're still seniors, not college freshman. And he goes on rants about the most boring things. He was hot though. I'll give him that. There would be times when I'd zone out and just stare at his ass while he lectured about whatever.

Next thing I knew, I was stroking my cock to my teacher fingering himself over me. His ass did not disappoint, I must say. When he invited me over in practically no time, I wasn't sure if I should. But my dick won that battle, because I was shortly throwing on a pair of basketball shorts and a tank top before sneaking out through my window. I drove to the small apartment complex that was lit by a single street lamp.

I went in the front door to see that the place was pretty bare. There was a couch, a small tv, and a coffee table. There was a stack of papers on the kitchen table and I knew that mine was the in the mix somewhere in it. English wasn't really my best subject. I failed it and science last year and got held back. My attention then trailed over to the open bedroom door. Every step closer, my smirk grew wider.

My eyes dilated when I took in the sight of my English teacher face down, ass up, waiting to be used like a slut in that same jock strap from the picture. I had stared at those perfect mounds many times before in class, and they were even better than I could have imagined. Perfectly round, hairless, and a thong tan line. His hole puckered as I'm sure he heard me enter. I was about to make Mr. Matthews my bitch.

I walked up to the bed and stood still for a moment, taking in the sight. He didn't move from his position, well-trained. The power dynamic between us had been flipped on its head. I lightly dragged a finger across his cheeks, getting within millimeters of that tight looking hole. Goosebumps spread over his ass, and he arched even harder, his hole coming skywards. I rested my hand on his right cheek and rubbed with my thumb.

Frustration hit me like a brick wall from out of nowhere. This man made my life hell. I spent all night trying to write that stupid paper. My hand stung sharply, and then I realized I had spanked him. It was hard too. Mr. Matthews yelped and his whole body tensed, but his face remained in the pillow. Already, a red imprint of my hand began to form. He then arched his ass a little more, as if to ask for more.

I indulged the slut. I spanked his other cheek, not quite as hard as the first time. It still left a resonant smack. A ripple went through his ass, and my cock throbbed. It was rock hard. As he yelped again, I rubbed him to soothe some of the pain. I got down on my knees behind him to get the up close view. I ran my thumb from the bottom of his taint up to his entrance. I hovered over it for a moment, noting that he held his breath until I gave in and put a small amount of pressure on him. He sighed. Nothing could shake the memory of the time he had dropped a marker or something and bent down to get it and that ass stretched his pants so nicely.

I rubbed in a circular motion and he let out a deep groan of approval. I was so fucking hard. It took everything in me not to whip it out and fuck him right there. I had to take my time though. This was a once in a lifetime opportunity. I couldn't fuck it up.

It was like slow motion when I moved my face in to bring my mouth to his hole. When my lips connected to him, I took off. My tongue was going 90 miles per hour. I ate him out like he were the only water for miles in desert. I prided myself in the fact that I could easily make someone cum with just my mouth. Girls, guys, doesn't matter. I leaned some more of my weight into it and pushed into him with the tip of my tongue.

He was moaning like a damn porn star as I did my thing. Somehow it didn't surprise me that Mr. Matthews was such a slut. I didn't hold myself back. I pulled back and spit on it, rubbing it in with my tongue before diving back into it. His sphincter began to loosen up for me. I could tell it had been a while since he'd gotten his ass eaten properly, if ever. I could feel his hunger growing though. A tongue poking around down there wouldn't be enough for very long.

I eventually tore my mouth away from his ass to slip my index finger into him. It slid in with ease from how well-lubed he was. Still, he was tight around my digit. It had been a while since he'd gotten fucked too. He moaned hard into his pillow. I hooked my finger into him and wiggled it around a bit. He clenched onto me, I smirked. Just wait til you get to the main attraction.

I then removed my finger and stood up. I grabbed him by the hips and pulled him in. Through my shorts, I pressed my dick between his cheeks. It fit perfectly. Without any hesitation, he pushed back into me, squeezing his ass around me. He was craving cock. Badly.

"Oh god, please fuck me," he cried out.

"You have to suck it first, slut," I responded.

•••

That voice. I knew it from somewhere. My mind scrambled to try to attach it to a face, but it kept drawing up a blank. Whoever it was knew how to eat ass though. I'd been in bliss the entire time. I felt the growing wet spot in my jock from all the precum I had leaked already. Then, I heard him.

"This shit is so stupid. I'm not doing it," Cole had said one day in class about one of my homework assignments. He had been a difficult student from the first day. After a fairly heated argument over his lack of academic effort, I sent him to the office and he spent that Saturday in detention. He begrudgingly handed the paper to me Monday morning.

I didn't want to look up. I really didn't. At that point, I just wanted to stay where I was, get fucked, and let it be anonymous. That wasn't going to happen though.

Slowly, I lifted my face from the pillow and let my eyes adjust to the lighting. Remaining in my position, I peaked over my shoulder and there he was. My student was standing at the end of my bed with spit shining around his lips. His arms were crossed, and my eyes glanced down to see the biggest bulge I think I've ever seen. He caught my look and smirked. My heart may as well have stopped there. I fucked up.

"Cole," was all I could manage to get out.

"Mr. Matthews," he responded with a cool, even tone. My cheeks began to burn, the ones on my face that is, as I began to process what had just happened. Then, my mind began to race with what could happen if anyone ever found out. I jumped up from my bed as if he hadn't just been tongue deep in my asshole. I then saw him notice my own bulge and the dark spot right at the tip. I tried covering it with my hands, but that didn't change the fact that I was standing nearly naked in front of one of my students. I couldn't bring my gaze to meet his; I had moaned for him so much already.

"I think you should go—," I began.

"Mr. Matthews, I said to suck my fucking cock," Cole said, accenting each word. He stood as still as a statue and looked at me expectantly. I looked at him in the eye, and then I looked at the bulge down below. He flexed it at me, and my hole throbbed a bit, still fully wet. I knew what the right thing to do was.

"We shouldn't be—," I tried again, but he held up a single hand to cut me off.

"I told you to suck my cock. Don't make me tell you again, slut," he said firmly. I gulped. Fuck, I was so fucking horny. And I'd seen it already in a picture, and it's so nice. And there was no one else around in this godforsaken town to even talk about gay stuff to. Plus I was already prepped to be fucked. But it was Cole. He was such a pain in the ass at school, no pun intended. I should've asked for a face picture.

In slow motion, I let my hands fall away from my crotch. We both looked to see that I was still fully hard, and the precum has seeped through the fabric and was running a trail down my bulge. Cole smiled. I turned around to grab the bottle of wine from my nightstand and took a big gulp. I really, really, really shouldn't be doing it, but I was. I lifted my leg to take a step towards him.

"No," he said abruptly. I froze in my tracks. I looked at him in confusion.

"Did I say you could walk, slut? Crawl to me," he ordered. Clearly he had done this before.

With a command like that, I couldn't do anything else but obey. The carpet tickled my knees when I hit the floor. I felt the carpet threads between my fingers. I kept my eyes down on the floor as I crawled over to him. I felt him watching me like a hawk watches its prey.

As I approached him, I looked down at his sneakers. They were white and blue with dirt stains along the sides and sole. I couldn't help but picture them in my classroom. English was his last period of the day, and he came from gym. There had been more than one occasion he tracked mud into my classroom. He was also the type to not shower after gym, because there was football practice after school. My nose could attest to that. One day, I swear I could smell his balls when he was sitting with his legs wide open.

He simply held his foot out, and I knew what to do. I untied his shoes for him and pulled them off, setting them to the side. A clump of dirt fell onto the carpet when I did. Next, I slid his socks off, laying them neatly on top of the shoes. I looked up at him when I finished and he looked down at me with an evil smile. He knew he had all the power, and I was at his mercy.

"Show me how bad you want it," he encouraged.

I lowered my face all the way down and kissed the top of his foot. I kissed the other. I heard him chuckle a bit, but I didn't dare look up. He flexed his toes, and I knew what to do. It's not that I had a foot fetish; it just felt like the thing to do.

Parting my lips and closing my eyes, I took Cole's big toe into my mouth. My lips wrapped around it and the pad rested on my tongue. It was a strange new feeling. He wiggled it around, and I started to lick all around it. It had an ever so slight bitterness to it.

"That's a good slut. Keep sucking," Cole said.

His toe came out with a pop. I moved down the row and took a few toes in at once. My tongue snaked its way between and around them. I tasted sweat, sock fuzz, and a callous. It didn't deter me though. I opened my mouth wide and tried to fit the whole end of his foot in at once. He wiggled his piggies around, squishing my tongue. I watched spit attach me to it as he pulled out with shiny toes. I couldn't believe I had just done that. I did the other foot just as throughly when presented with it, and Cole laughed at me.

"May I suck it now?" I asked from my knees, looking at up to him. He reached out to grab my hair into a tight grip.

"You're quite the fucking whore, aren't you Mr. Matthews?" Cole spat out. I breathed in sharply at the pain. No guy had ever treated me like that before, and it had me hard as a rock.

"Yes," I squealed out.

"I wanna hear you say it," he said, leaning down to look me in the eye.

"I'm a fucking whore, Cole," I responded, using more of my chest to speak.

"It's not 'Cole' tonight, bitch. You can call me 'sir.'"

"Yes, sir," I replied and that's when he released my hair. I collapsed down a bit to recover.

"Good boy. Now take my shorts off," he ordered.

I didn't hesitate to get back up on my knees and stare directly at his crotch. I looked up before touching him, and he gave me a what-are-you-waiting-for kind of look. I reached out and took his waistband in my fingers. I didn't feel any underwear. My knuckles dragged along his skin as I pulled his shorts down. First, it was his pubic hair. I could smell him the moment it was uncovered and I was hooked. I revealed his dick inch by inch. It was thick and fully hard. When I finally got to the head, I let it fling out and bounce in front of me. It was even more beautiful in person. My eyes went wide.

"Now suck it," he said plainly.

I got closer and could feel the heat radiating off of it. I opened my mouth wide and took his head in.

•••

Mr. Matthews' soft lips closed around the head of my cock, and I unintentionally let out a deep moan. It was bliss. If you had pinched me, I'm sure I would wake up from the wildest wet dream of my life. I cannot believe my English teacher just sucked my toes. Never in a million years would I have guessed that he was that kinky.

I relaxed my head back as he slid down further on my cock, taking in inch by inch. His tongue felt incredible. I couldn't even figure out what he was doing with it. Before long, he had the whole thing down his throat. Mr. Matthews the Deep Throater. Good to know. He held onto the side of my thighs for stability as he sucked me off. He took long, slow strides so I could watch myself appear and disappear.

I moaned again and looked down at him. He looked up at me with his green eyes. They were beginning to tear up, making them glossy. I realized just how attractive he was, especially when his mouth was full of me. I watched him suck with a passion. Every minor movement he made was perfectly placed. I'd never had head that good before.