High Risk, Higher Reward Pt. 01

Author's note: This story is greatly inspired by 'The Professor's Gambit' by user Black_Hat_Lee and is kind of like a fan sequel. This story should be able to stand on its own however because you can gather what happened before through internal monologue and conversation, I wanted to create a story where the unnamed Professor and Sylvia had a more complex relationship and motives almost like enemies to lovers. I still recommend you check out his story because it's a hot read for anyone into the dominant professor dynamic but realize the motivations that drive both the main characters are slightly different in my story even though they share the same names and physically the same backstory.

CW: Nothing too extreme for the internet, but my story includes some intense themes such as domination, blackmail, reluctant submission, rough sex, breathe play, semi-public humiliation, and swallowing nasty things??, etc so consider yourself warned.

If you're here just to get off I have headers showing where the introduction ends/ sex starts so you can hop right in if you don't care for the story (you're missing out imo), there's still a bit of build-up though so try to be patient you kinky readers ;)

Part 1:

Since Sylvia's first escapade as my schoolgirl slave, her temperament had been disgruntled at best. Her typically warm personality had frozen over so to speak. In class, she had become more hesitant to answer my questions, often staring at me with eyes like daggers for several seconds before reluctantly replying. She used to take any chance she could to demonstrate her intelligence in class to impress her professors because she thrived on the approval of authority figures. That's probably what made it so easy for her to do well in school, and I was willing to bet her looks hadn't hurt her either.

It's debatable whether her continually bad attitude is a symptom of my ongoing efforts to train her or just the effects of the birth control I put her on after filling her young fertile pussy with my seed during our first 'session'. My leading theory though is that this shift was caused by me turning her aforementioned need for approval against her. Even though she acted as if she had hated it, I had pushed her to fulfill one of her deepest darkest desires, to be sexually dominated by me, and in the process, I also gave her the most intense squirting orgasm of her life thus far. No matter what she consciously thinks of me, subconsciously her brain sees me as an unrivaled authority figure with the power to give her immense pleasure, her master. Meeting the expectations of her peers is no longer rewarding to her because their power to pressure her pales in comparison to the power I hold over her. Only my approval matters enough now to release the pleasurable reward chemicals in her brain. She would either come to accept that by submitting to me and living out all her previously suppressed fantasies in a fulfilling life of servitude or she'll be torn apart by a life void of any fulfillment all because she let her inhibitions control her.

I've been starting her training slowly, so I can focus on chiseling away at what's holding her back. If I advance too quickly, while she hasn't fully submitted to me yet, I'll scare her even more than I already have, forcing me to waste time fighting against her fear. I can't let her break free either though, so I need to keep her just submissive enough that she doesn't try anything stupid to break our agreement. Sex with Sylvia is like a drug, and while we had originally agreed to only having her serve me until she graduates a year and a half from now, I was determined to make her submit to me permanently so I'd never have to give up my new addiction. That might seem selfish, and it is, but I'm not doing this just for myself; I'm confident that if I succeed Sylvia will be happier than ever. That's partially why I'm taking the time to do this the hard way, if all I wanted was for her to remain my slave I could simply take pictures or record her during one of our sessions and blackmail her, but I want her to do it willingly and deep down so does she. That essay was a silent plea for help, she admits that she longs for me to take her until she starts enjoying it, and that's exactly what I plan to do.

A promising early indication that my efforts are having the desired effect on her is that her wardrobe has also taken a turn. Her typical pre-submission professional outfits still make regular appearances, but more recently she's arrived to class dressed noticeably more provocative. On multiple occasions, she's worn slightly more appropriate versions of traditional school girl outfits consisting of a blazer, blouse, tie, skirt, and stockings or shin-high socks with heels. I made it clear to her early on that I was to be her only source of sexual release and I think after not orgasming for about a week she's subconsciously trying to entice me.

Regardless, it's drawing near to the end of semester crunch, the time when good students began preparing for final examinations so academic tensions are running high. Sylvia's performance up until recently had been nearly flawless, but since pledging herself to me her scores were barely clinging to an 'A'. Admittedly that doesn't sound like a big deal, but for someone like Sylvia who's forced herself to achieve perfection for so long, it represents a major blow. The last midterm before the final is coming up, and it's a perfect opportunity to start leveraging her need to do well against her. Her pride in her intelligence makes her believe she can eventually outsmart me. I certainly couldn't make her dumber, and I didn't want to, but I could degrade and humiliate her every mistake so that her confidence in her abilities was reduced. If I was successful, it would prime her for further training as we built up to the day she would give herself to me willingly.

The school day before the test, I summon Sylvia into my office after class. Beckoning for her to follow me down the hall, she begrudgingly obeys like a loyal foal. Once inside my office, I lock the door behind us.

"What do you want from me now? Let me guess another fucking blowjob." She says, failing to hide her frustration. Sylvia had always taken school seriously and ever since she submitted that stupid essay by accident she's had to juggle her responsibilities as a student and as my slave.

At that, I grab her hands, which were hovering near the hem of her skirt as if she expected she'd need to remove it at a moment's notice, and I clasp them together above her head as I pin her to the back wall of the office.

"I thought we discussed how you would refer to me, or do I need to give you another lesson?" I say in a monotone voice while leaning in closer to her slightly turned face.

"No professor," she stammers.

"Look at me when I talk to you my pet"

"Yes professor."

With that, her fear temporarily changes to anger as she turns her head to glare at me before returning to a more complacent expression. That's something I love about her, she has a fiery temper that sometimes gets the best of her, after all a slave you never have to punish isn't nearly as much fun. That fire was further stoked by overconfidence in her abilities, it's true that she was brilliant but priding herself on that fact sometimes blinded her to when to give up. In this mental state, she'd never willingly submit to me.

Still holding her against the wall with one hand, I press the other inside the edge of her skirt from above until I meet her panties. I grip both the top of the skirt and her undergarments as I pull away from her body so that I can see inside.

Sylvia releases a faint gasp as she moves her hips forward in an attempt to minimize how much I can see.

"Back", I say as if I'm talking to an animal. The squirming of her hips dies down but doesn't stop completely after that.

I peer inside, and as expected Sylvia has grown a small bush of black hair around her mound. Outside of occasionally taking advantage of her glorious throat skills before or after class, I had yet to seriously fuck her as I had on day one. That was about to change though with this coming midterm.

I release the fabric and a slight slap sound created by the elastic impacting her pale skin seemingly echos through the small room. I let go of her hands and they limply fall back to her sides but she doesn't move.

"Satisfied by what you saw professor," Sylvia replies in a slightly mocking tone.

"Hardly," I say as I give her an angry glance while I sit down at my desk.

"Now that you're done acting up, listen closely to what I have to say or I'll discipline you right now if I have to. On Monday I expect you to arrive to class braless, neatly trimmed, and with this inserted in your ass." I say calmly but firmly as I open a drawer and remove a seemingly normal butt plug of medium size.

Sylvias eyes widen for a moment as she stares at the plug lying on my desk. I can tell the gears in her mind are turning as she tries to think of a way to wiggle free from my demands.

She approaches my desk and leans over it so that her elbows rest on the table supporting her head, giving me a nice view of her gorgeous breasts as they hang down inside her top.

Breaking out her flirtatiously mocking tone she says, "You're absolutely filthy professor, will seeing your prized student's nipples while she takes a test turn you on? Will the thought of my tight young asshole being stretched by a plug while I sit mere feet from my fellow students tip you over the edge?" She giggles after that but it's half-assed at best. It's clear to me that while she doesn't find my demands all that difficult she still is willing to push her luck to get out of them.

"I have a hunch that we're both going to enjoy this, but until I experience it I can't say for certain. Don't even consider showing up without that plug in your ass or I will make sure you can't sit or talk properly for the rest of the week."

Sylvia drops the act and grumpily pockets the plug before standing up, sneaking in an eye roll as she does so.

"And Sylvia, it's bold of you to assume that just because I've fucked you that makes you my 'prized' student. Don't forget your future is still in my hands." I motion towards the stack of papers on my desk where her incriminating essay sat just a few days ago.

"You're dismissed, for now, enjoy class."

"I will professor," she says while walking out the door pretending to make a pouty face.

End of Introduction

For a girl as sexually talented as Sylvia, my demands for the test didn't seem too extreme given the circumstances, but I'm going to make sure she pays for all the lip she had just given me.

As class starts the next day I observe Sylvia sitting at the front of the room wearing a black form-fitting dress that came down to just above her knees with matching stiletto heels. She must be trying to toy with me because while certainly stunning, the look was a far cry from school appropriate, especially given that the dress seemed to be backless most of the way down to her ass. To my slight dismay, her nipples were barely poking through the material, but I knew that would rectify itself soon enough. As I give the instructions and have TA's hand out the Exam I watched the students settle in. To my surprise, one stood out to me even more than Sylvia. It was a rather petite girl sitting on the opposite side of the room one row back, but what made this small blonde stand out was the fact that she was staring with contempt at Sylvia. I glanced at the roster and my suspicions were confirmed after a quick scan, the girl was Emma. I didn't recognize her at first but now that her profile is pulled up on my computer screen I notice that she's on the school tennis team and has been just behind Sylvia in marks all semester. For a small girl with glasses, her athletic frame and what seemed to be pure hatred in her eyes made her surprisingly intimidating.

The timer began and the furious sound of pencils on paper filled the room. I kept an eye on Emma, who was now looking at her paper, while I shifted my focus back to Sylvia who was working at a calm pace. If it wasn't for the fact that she had her legs spread just far enough that I could see her pantieless nether regions from my desk at the front of the room nothing would be too out of the ordinary.

"Cheeky girl," I thought to myself as I reached under my desk for a remote. Her decision to also tease me by not wearing any underwear at all would bite her. I grasp the remote and adjust the settings I was looking for before pressing the power button. Immediately, a faint humming could be heard, comparable to a cellphone on vibrate at the bottom of a schoolbag. Sylvia pulls her legs closed and she looks up from her test as do a few students around her. The buzzing noise emanating from Sylvia's ass garnered only a moment's notice from most of them but I watch with glee as she sits up and tries to adjust her legs so that the end of the plug doesn't vibrate against the noisy plastic seat. Her eyes zero in on me as if trying to smite me via sheer willpower before she returns to writing.

I had set the Bluetooth vibrating buttplug to a randomized pulse setting that only allowed for a moment of respite before cranking the intensity back up. While the audible buzzing had died down due to her efforts it was obvious that she was having trouble focusing with my device vibrating in her ass. After a minute or two I could now see her nipples, hard as diamonds, poking out of her shirt. I could tell whenever the vibrations spiked because she'd move her head slightly and cough or clear her throat as if that would prevent the orgasm from building insider her. Halfway through the test, she was obviously getting desperate because she was rocking in her chair a little, letting out small moans or grunts every time someone else made sufficient noise to cover up her embarrassment. Still, she was determined. I could tell she was speeding through the exam and to my surprise, she got up just minutes later.

As if she was calculating every step, Sylvia carefully comes forward to turn in her test in record time. She takes several missteps and is wincing to hold back the pressure inside her. When she reaches the test drop off she almost throws down her exam, looking me in the eyes angrily before briskly walking to the door. When she was just about to leave I turn the plug up to its maximum and from behind I could almost swear that her ass was jiggling. I'd been hiding an erection since her nipples started showing but seeing her knees bend as she nearly collapses in the doorway makes my cock jump.

After she exits I reduced the vibrations and pull my phone out under the desk.

Texting her, "Don't you dare remove that plug until the hour is over. Go to the men's restroom at the end of the hall and wait for me in the last stall. Try to hold in your orgasm until I get there to lock the outside door, otherwise who knows who could be inside listening."

I look up from the sent message and almost jump when I see Emma standing on the other side of my desk with her exam in hand. Instead of putting it in the drop box, she hands it directly to me and winks before strutting away. Emma was sitting in the second row before so I couldn't see what bottoms she was wearing, but now I was captivated by the skimpy white tennis skirt barely covering her ass.

The remaining students file out soon after but in the meantime, I read the note on the front of Emma's exam. It was a short message that got straight to the point and made my stiff cock almost sore from arousal.

"Professor, I'm so close to beating Sylvia in the class rankings and increasing my GPA to a 4.0, all I need is an A in this class. I'm willing to do ANYTHING you want for as long as you want if you can guarantee me a higher final grade than hers. Here's my number, I'm willing to meet with you any time before the end of the semester. -Emma"

Dirty thoughts of what I could do with two fit coeds at my disposal raced through my mind but given that the last student had just turned in their test and left the room I had other priorities. I straightened my pants and made my way to the men's room.

Sure enough, once I stepped inside I could hear a faint hum and muffled noises of pleasure. I check that we're alone and lock the outer door before walking to the last stall. I'm greeted by Sylvia, collapsed against the wall with a hand over her mouth squirming in rhythm with the vibration pulses. She was desperately trying not to make any noise that would give away her presence and must have been truly desperate to orgasm because It appears she ran here barefoot given that her heels are lying in the corner next to her small purse.

She looks up at me and through ragged breaths, almost shouting "I fucking hate you, I'm going to do awful now because of you."

I let her temper slide given that it's the first time I've done something like this to her.

"You, my little whore, will do fine. I might even throw in some bonus points for that wonderful show you put on for me. Although not wearing underwear was a dumb choice, if you had the vibrations would've been almost silent."

"Fuck off professor"

"Skip the back talk and lift your dress up. Have you orgasmed yet?" I say while turning the butt plug off with the remote.

She looks down in shame while hiking the dress up above her neatly trimmed pubes until it rests just above her ass.

Meekly she lets out a "yes professor."

Her answer honestly surprises me, I had meant only to distract her and sprinkle in some beginner public humiliation before fucking her in the bathroom. Given how little training she had under her belt and her propensity for squirting I had elected not to force her to use anything that would directly stimulate her pussy for exactly that reason. For her to have cum from anal stimulation alone must mean she is quite the ass whore.

"Just once? Did anyone hear you?"

"Once, I don't think anyone heard."

"You don't think? So not only did you cum without me, you mean to tell me you didn't check the stalls beforehand?" I say in a harsh tone, grabbing under her arms and pulling her further up against the bathroom wall.

"No! I mean yes professor," she says clearly, caught off by my sudden change in mood.

As much as I love the idea of her orgasming with an audience it would be a stupid way to get caught.

"You're smarter than this Sylvia, now I'm going to need to punish you for being so stupid and reckless."

I can tell she's once again recalling our last session which left her ass resembling a tomato and her thighs a similar shade; she skips her usual dirty talk straight to guilt-tripping.

"But... but, you told me too, I did what you asked" she pleads, looking at me with puppy dog eyes that still seemed less than genuine.

"Shut up, palms and tits against the wall," I growl.

Once she gets into this modified 'wall' position with her arms crossed above her head her nipples become even harder, insulated from the cool surface by only the thin fabric of the dress. Her state of helplessness makes her understand that she's in real trouble now. As I start undoing my belt and zipper I hear a whimper escape her mouth.

"Please don't spank me, professor, not again. I can't take it again."

"I saw how sopping wet your pussy was before you left last time, I know deep down you enjoyed it. Just be grateful you're not bound like last time too." I jeer, questioning whether she might enjoy it more like that given that was her fantasy.

Sylvia sways back and forth slightly shivering in front of me but makes no move to protect herself like last time. Her arms and tits loyally remain pressed against the tile with her dress still clumped above her ass. From here, I enjoy seeing the end of the deactivated butt plug visibly hanging from her anus. I pull back my arm as if to spank her and she tenses in preparation but I don't swing. Instead, I grab the remote in my pocket with my other hand.