High Risk, Higher Reward Pt. 02

"I expect you to be waiting here in this position to greet me at 4 o'clock since you've decided to start showing up early."

Sylvia is looking straight ahead, doing her best to avoid acknowledging my presence or her fear beyond answering my questions and posing for me. Now that it seemed unlikely she was going to get any pleasure during this encounter, she was being less responsive.

I get on one knee and wait there until her eyes eventually meet mine. She seems unamused, but that quickly changes. I lean towards her ear and place a passionate kiss on her neck while caressing the opposite side of her face. Her breathing, which was just starting to slow down, picks back up, and I swear I can just barely see her eyes roll back into her skull. Working my way up, I gently bite her earlobe, momentarily pulling it into my mouth.

This is the first time I've given her this type of affection, and I hope to push her craving for me even further. I know exactly how cruel I'm being to her, but her loyalty needs to be strengthened for Friday to go well.

Before I speak again, I reach between her spread legs and trace a line down her folds through her panties. She flinches from my touch at first, hesitant to allow me to please her given my recent track record, but proceeds to give in and starts slowly gyrating her hips back and forth on my fingers.

Whispering into her ear, "I'll give you a tip, I've been paying attention so I suggest you stick to the truth on Friday."

I lean away from her face as her hips slow, the expression she's fighting to hide, and the dilation of her expansive blue eyes imply she's thinking about something that turns her on. She snaps out of it to give me some backtalk.

"What does that mean? Are you planning on interviewing me mast-"

I cut her off by grabbing her pussy through her panties, holding onto it hard. She winces in pain and breathes in sharply.

"What did I tell you earlier? Shut. Up."

I let go of her pussy and wrap the fingers of my bruised hand around her neck. She's once again caught off guard, and I pull her into a forceful kiss. In doing so, she's pulled forward and forced to put her hands on the ground for support. More surprised by the kiss itself than my brutality, she hesitates to oblige me access to her mouth. I grip her neck tighter, repositioning my other hand inside her panties now. This makes her open up and return my kiss, but I don't allow her to breathe just yet. I take the chance to explore her mouth with my tongue while I pleasurably assault her clit. She resumes grinding her hips into my hand, so I put a finger inside of her.

A moment later, I'm satisfied that the kiss has achieved the desired effect so I vacate her mouth. I look into her watering eyes and insert another finger agonizingly slowly while rubbing her clit with my thumb. Now being choked on her hands and knees with my hand up her dress vigorously pleasing her pussy, she's opening and closing her mouth like a fish out of water.

"Get back in position" I threaten.

She tries her best, putting one hand back behind her head while the other holds up her body, but she's so out of breath at this point no matter how hard she tries to get up she can't fight my grip. Her eyes are pleading with me to let go, and she's squeezing any noise out of her throat she can. Finally, I lift her upper body back to vertical by her throat and release her.

She's coughing, gulping for air, but to my immense pleasure, I watch as she puts her hands back behind her head. Reaching above her, I grab a bundle of her hair and pull straight up away from the ground. She's still coughing, but now she's also grabbing at my hand trying to make me let go. I slide my fingers out of her folds before she can get off with the help of all her natural lubrication and put the dripping digits in her mouth.

"Suck," I order.

When she keeps her mouth open for several more seconds for air, I press my fingers into her tongue to force her to taste herself. She closes around them, creating the desired suction while breathing hard through her nose.

I push my hand deeper into her mouth, and she accepts my fingers into the back of her throat before I pull them out and wipe them on her face. This was neither the first nor would it be the last time she'd be covered in her juices.

Letting go of her hair, "See, was that so difficult?"

She drops back down and moves to wipe her face.

"Don't you dare, get back in position."

Angrily grunting after being denied an orgasm for the second time, not allowed to even clean up, she returns her hands to her head.

"You may get up and go to class, but don't even think of wiping that mess off your face. If you're lucky everyone will still be ignoring you."

I could tell my words stung as I said them, Sylvia had told me she hated feeling like she didn't exist when she was low, and now I was using it against her. The fact that she treated me the same two days ago seems to slip her mind. Her issue of being ignored had only gotten worse since rumors about what happened began circulating, people in class avoided ever acknowledging her out of fear their professor might lunge across the desk at them. Meanwhile, I had the opposite problem, both the higher-ups at the school and the local newspaper had found out about the incident wanting to make a big deal out of it as if they didn't ignore every other victim that wasn't saved by a member of faculty. It took a lot of convincing for them not to run stories titled things like "University Professor saves Student from Drunken Assault", and I had to pull the "Out of respect for the victim card." Making Sylvia's matters worse for her was now that I was being recognized as a hero there was no way anyone would believe her if she tried to accuse me of anything. Luckily for me, Sylvia had realized this too and kept her mouth shut about our contractual relationship when we were briefly questioned about what happened yesterday.

Regardless, I felt bad for her as she sat there with tears about to well up in her eyes. She got up and was about to trudge away, after putting on her heels, when I decided I'd cut her some slack knowing that what I would do to her on Friday might make her hate me forever.

"If you're a good girl during our meeting later I might feel benevolent enough to let you cum."

She barely spared me a glance before opening the door and walking away, but I still caught a sliver of happiness showing through her anger.

Once again, class dragged by but this time all but one person was avoiding looking at Sylvia. As I lectured, I repeatedly noticed Emma eyeing her when she thought neither of us would notice. I wondered if Sylvia had seen, but I doubted it. Not only was Emma on the opposite side of the room, but I had noticed Sylvia's mind tended to conveniently shield her from anything that didn't fit her narrative. For example, she claimed hardly anyone noticed her get assaulted but obviously that wasn't true. Not only did someone report it to the authorities, causing me all that trouble, but it stirred up enough noise in the hall I was able to hear it from my classroom before she arrived.

When class ended, Sylvia still didn't stick around long, but she did look at me before she left. The rest of the day my stress levels continue to rise as the clock approaches 4 pm. I knew Emma was going to arrive at 4:40 and 40 minutes would have been plenty, but all jokes aside I had one real appointment with a student starting at 4:20. Logic would tell me I had 20 minutes to deal with Sylvia, 20 for the student who actually had an appointment, and then I was free to start discussing with Emma. Greed, on the other hand, had already thought of a way to keep Sylvia there for 40+.

After I finish talking in my last class of the day, I check the time. My watch says 3:50, and I decide to at least swing by my office to see if Sylvia has arrived yet. As I walk the last few meters to my office my heart feels like it's inside my throat, what I was about to do was increase the stakes of an already risky gamble after just striking the jackpot. For a brief second, I debated if involving Emma was worth it, but when I got to the door I decided it was already too late to back out.

Stepping inside my office quickly, as if anyone was paying attention, I was immediately surprised by what I couldn't see. I know Sylvia is here because the light from opening the door had flashed across her, but the lights inside are turned off and the shades are drawn. I fumble for a moment in the dark before flicking them on and was greeted by a sight that certainly excited me. Sylvia was sitting in the exposed position with perfect form but lacking her dress. It took me a few seconds of ogling her breasts for me to snap back. No matter how many times I see her naked, I don't think I'll ever get tired of the sight. Right now, she's kneeling on the floor wearing nothing but her heels, socks, garters, and panties, looking more seductive than ever.

"Someone's preemptively excited don't you think?"

"Master, have I started to bore you?"

I pull a chair from the corner and sit down in front of her as I undo my belt.

"Never my dear," I say watching her eyes track my every movement, "is this what you want?" Motioning towards my crotch.

"Yes master."

"Well then, you better come give me a good reason to let you orgasm."

She didn't hesitate, knowing finally being able to release was up for grabs. Seductively, she crawls towards me with her perfect breasts hanging down as she does.

Noticing my interest, "would you appreciate fucking my tits master?"

I place a finger under her chin now that she's close to me and tip her head up.

"I certainly would, but this isn't just about me. It's up to you to decide how you want to convince me you deserve to cum."

"Yes master!"

She's excited now, her confidence in her ability to please me is running high, but I'm not convinced. So far, I've had to do almost all the work every encounter, even her first blowjob on me only got good when I started fucking her throat. Now it was all up to her to make me happy.

She unzips my pants and frees my hard cock before spitting on it. She starts rubbing in the saliva while sucking off the head and allowing more to drip down my shaft from her mouth. I spread my legs further so she can get in close and she does just that. Pausing her oral lubrication job, she sits up and positions her breast while I lean back prepared to let her do the work. She looks at me with begging eyes while squeezing her tits around my cock.

I watch the clock as she begins to tittyfuck me, we still have about 20 minutes before I start taking meetings but she doesn't know that.

"Do you like this master, does having your dick stroked by your slave's tits make you want to cum all over them?" Sylvia only half teases without pausing her little hopping motion between my legs. Unknown to her, I don't waste my cum like that outside of very specific conditions; I like to see my seed consumed, dripping from well-used holes, or both.

Regardless, It feels amazing having my meat pumped sandwiched between her perfect warm breasts but I've grown tired of her verbal attempts to toy with me. Besides, I know her throat could be put to much better use giving me even greater pleasure and would save me time.

"I think I prefer your mouth swallowing my cock over interrupting me."

The tired eye roll she gives lets me know she may be growing tired of giving me blowjobs, but the expression evaporates quickly as she rededicates her efforts. She looks almost excited now, knowing how much I love her throat, she was at least positive it would secure her a sweet orgasm. Dropping back to her hands and knees, she teases me with her tongue a little before beginning to bob her head up and down on my cock. Her throat has never failed to impress, but the minute she gets her hands involved it all goes to shit; she's being far too greedy and grips my shaft so hard it's uncomfortable.

"What are you doing?!" I demand as I tug on her hair, "get your hands off me. I want a blowjob, not my dick twisted. If you want an opportunity to orgasm you'll bury my cock in your throat this instant"

She does as she's told and puts her hands behind her back like a good submissive before resuming

"Much better, now keep them there. From now on slut, you're not allowed to use your hands for blowjobs unless I tell you to."

Sylvia is too busy forcing my dick down her throat to pay my comment much mind. The feeling of my cock filling her tight wet esophagus provides the instant relief I'm looking for. Several seconds of glorious eye contact go by as I groan from the wonderful feeling. She can tell how much I like this, moving up and down just enough so that my tip pushes past some resistance each time it goes back down her throat. Her gag reflex is heavily suppressed, but it's still degrading and uncomfortable to resist the natural urge to vomit up my invasive member. I'm worried she's going to pass out, after depriving herself of air for so long, but she presses on through teary eyes to prove her skill once again. The feeling of her throat and wet tongue so far down my shaft is pure oral bliss. I'm getting close, so I know it's time to cut this short.

"Good girl Sylvia, I think you've earned your reward."

Sylvia throats my dick one more time for good measure before releasing my cock from her mouth. She gets up and has her fingers wrapped around her panties almost instantly.

"Woah, slow down and let me enjoy this, you really have forgotten everything my little cock whore."

Visibly disappointed, she pouts and turns around with her legs slightly spread for me.

"Is this slow enough for you, master?" She utters with a hint of frustration before bending forward and wiggling her ass a little as she teases me. Her heels show off her legs beautifully and moves her ass closer to my eye level.

"Much better."

Painfully slowly, she pulls down her panties and allows them to fall to the floor over her heels. Looking over her shoulder, she spreads her ass cheeks with her hands to give me a wonderful view of her bald anus and pussy.

"Come and take them master," she taunts, stepping out of her fallen underwear and putting her elbows on my desk in preparation for getting taken from behind.

"You continue to misunderstand my dear, if you want to orgasm you better come ride my dick yourself. My patience is wearing thin so I suggest you impale whichever hole is going to make you climax the fastest."

I can tell now, she's really upset she's having to do all the work but hopefully, this will make her understand being her master is more difficult than she makes it out to be.

Still desperate, she struts over to straddle my lap facing me, positioning my dick to enter her pussy. I place my hands on her hips for stability but other than that I let her do all the work.

She lowers herself down onto my cock, which easily slides inside her dripping cunt. She's needed this for days, but she's evidently an inexperienced rider because she struggles to get the depth or the tempo she desires. She's giving it her all though, desperation more than making up for the unideal circumstances. It's hard work pleasuring herself like this, but it's certainly enough to make an orgasm build inside her. I'm nearing climax too, since her throat did such a good job, and I freely let myself make some noise as I approach.

Realizing what my grunts mean, Sylvia begins to panic a little; she wasn't close enough yet for him to cum.

"Please master, may I touch myself!"

"Yes you may."

Her hand bolts to her clit, she starts rubbing it exactly the way she likes. It's a tight race to orgasm as she continues bouncing up and down.

"God fuck, please may I cum master!"

I can't hold it in any longer and try to suppress a loud groan as I cum inside her; I pull her hips down to prevent her from trying to continue and to penetrate her young twat as deep as it'll go. Her body is bucking, struggling against my hands for anything more while she continues rubbing feverishly. Having her pleasuring herself out of panic on top of me makes the feeling even stronger. I relax my grip and thrust into her a few times, making her yelp with every stroke as the last of my cum fills her. It's not enough though, she's so damn close I can actually see a few tears start streaming down her face as she thinks I'm going to leave her on the edge of an orgasm she's worked so hard for.

"Cum for me," I say, releasing her hips.

I wrap my arms around her and we collide into a hard and passionate kiss as I allow her to grind herself to orgasm on top of me. Unlike before, she doesn't fight it or hesitate, we're both holding onto each other. Her moans are trapped between our mouths and cover up my own noises of ecstasy as she climaxes. It wasn't the most pleasurable or most intense orgasm she'd ever had, but it was glorious, and the way she kissed me made me doubt if I even needed to continue with my plan. Her vulva's grip on my cock weakens as she rides out the waves of pleasure she's been waiting for all week, but the intensity of our make-out session continues. It wasn't like anything I had experienced with her before, it didn't feel like she had any hidden agendas behind it or that I was forcing her to, it felt like she wanted it just as bad as I did. As her orgasm begins to fade and her body settles on top of me, our kiss loses its eroticism. I'm so close to accepting that this is it, the moment where we'd both drop the mind games.

I couldn't even hear the knock at the door because of how quickly and forcefully Sylvia leaps off me. Mid kiss, she had jumped so hard she managed to completely clear my cock, which I was thankful she didn't land on and left me looking like I was making out with an imaginary woman. Now she was cowering next to my desk, silently pleading for instructions on what to do.

I knew this would happen, and I cursed myself for not planning better, I didn't expect her to respond so well. Sylvia is panicking, looking for her clothes which lie on both my desk and the floor.

"Wait position"

She looks at me, pure terror in her eyes. She may hate being ignored, but she certainly wasn't looking to get caught naked.

"No, please master."

"Shut up and move," I say as I grab her panties off the floor, approaching her.

She very reluctantly stands with her hands behind her back, and I push her behind my desk. I drag her dress off the top surface and throw it on the ground underneath, along with her panties. She starts understanding what I intend now, but I still surprise her by pulling a pair of handcuffs from the drawer and locking them around one of her hands. I shove her underneath the desk before she can react, and I'm praying she hasn't allowed the load I blew inside her to leak all over the floor. Kneeling on top of her dress facing my seat, she's almost in position. I take her hands and use the cuffs to chain her to the center leg of my rolling chair.

"Please come in," I shout towards the door as I sit, pulling my chair in and forcing her face into my flaccid cock underneath the desk.

The door opens and I recognize the student as the one who scheduled the appointment.

"Sorry about that, I have to shout for you to be able to hear me. That's the problem with this building, the walls are quite thick."

"No problem professor, I'm just here for individual office hours. I was wondering if you could go over a few things about the final with me."

Jesus if I knew how stupid his reason for scheduling a meeting with me was I would never have accepted.

"What seems to be the problem? I believe I sent out all the information already and the syllabus has everything you need to know for what to study."

Evidently, my passive aggressive statement tickles Sylvia because I can feel her stifling a laugh against my crotch. I can't let her make any more noise so I nudge her with my foot and do some unsuspicious hip movements to get my cock back in her mouth.