Blackmailed by His Student

"That was before, but now I'm in control because I have the recording."

"Are you now? Well, if you're in control, you'll have no trouble stopping me from doing this..."

I grabbed her inner labia and pulled and twisted.

"No, stop! Ow, that hurts!"

"...or this."

I reached for the hem of her top and yanked it up, uncovering her breasts. They were fairly small, but looked just right on her slim frame. Her very perky nipples were begging to be abused, so I bit one of them.

"Ouch! If you do that again then I'm sending the recording directly to the Dean as soon as I get free!"

"Really? You'd give up the $4,000 and the A grade, just because I tormented you a bit?"

I could see her resolve fading. She was at least as turned on as I was. And she had responded really well to my tentative Dom/sub play earlier. As I was waiting for an answer, I slipped two fingers into her pussy and started slowly finger-fucking her.

"Yesss, keep doing that... Mmmm."

"Call me 'Sir'. Now say it again."

She shot me a look of petulance and desire.

"Please Sir, keep doing that."

"Much better."

I sped up and reached deeper into her. Feeling for that slightly more textured area of the G-spot, I got her to moan loudly. While working her G-spot, I leaned forward and took her other nipple in my mouth. Sucking on it elicited another moan. But when I got it between my teeth and started biting down just a bit, she blurted out, "No, no biting!"

"You forgot to say 'Sir'... and that gets you a punishment."

This time my bite was not gentle.

"Oooow, please stop Sir!"

I held the bite another few seconds before letting go and giving her a big smile. Then I pulled my fingers out of her pussy and smeared her juices all over her face.

"Don't you look lovely! Makes you look more like the whore you clearly are. An expensive whore, but ultimately just a lying whore. Was any of the stuff you told me true? About your lack of experience?"

"I'm not a virgin... Sir. But I've only had sex a couple of times and it was kinda disappointing. Both boys came really quick."

"What about blowjobs? Are you any good at giving those?"

"Yes Sir, I've done that more often, and I seem to be pretty good at it."

Standing between her legs, I started undoing my jeans. Time to find out if this Barbara's mouth felt as good as the last one's.

"Have you swallowed cum?"

"No Sir."

"Well that's about to change."

As I undid my belt, I got an idea. After zipping down and getting my half-hard cock out, I pulled the belt from my pants. Holding both ends of the belt in my right hand, I held it menacingly against her breasts.

"But first you need to earn my cock. Getting to suck your Sir's cock is a privilege, and you haven't earned it yet. I'll give you two options for how to earn it. Either I bite each of your nipples hard for 10 seconds, or I give each of your breasts 10 lashes. Okay whore, which will it be?"

"No Sir, please don't, I'll be good and give you a really good blowjob... and I'll even swallow your cum."

"Wrong answer. Pick one or the other right now, or I'll do both!"

She looked scared, and obviously worried that her plan was going in the wrong direction. Then in a small voice, she said, "Sir, the belt, but please be gentle."

"Are you scared?"

"Yes Sir, of course I'm scared. I understand that you're very angry at me and I'm afraid you'll really hurt me."

She was right, I was furious at her. And since I had the upper hand for a little while longer, I was really looking forward to making her suffer. But I was no monster. I had done this before, with masochistic sex partners who had actually suggested I do this to them. To my surprise, I had really enjoyed it. Being honest with myself, this wasn't only about revenge, it was just as much about my sexual pleasure.

"Yes, I will hurt you, but I won't cause any actual damage. You may get some bruises, but nothing that lasts more than a few days. Have you ever been spanked?"

"Yes Sir, on my ass... and my pussy. I didn't expect to like it, but I did. The guy kept switching between finger-fucking me and slapping my pussy. It hurt, but it also got me really hot and I came super hard."

Interesting. I wasn't expecting such an honest admission of her masochism. My cock responded by becoming harder, which may or may not have been the reason she licked her lips.

Twenty lashes later, her breasts were bright red and her eyes squeezed shut. Small moans had escaped her lips and I was pretty sure her pain had aroused her as much as me. Not waiting for her to open her eyes, I grabbed her head and pulled it forward until my cock hit her lips.

"Now you get your reward, bitch."

Her smile was genuine. I rolled back my foreskin and pushed my dick into her eagerly awaiting mouth.

"Mmmm."

This time it was my turn to moan. Her oral skills were excellent. Or maybe I was just very overdue for a blowjob. Wanting this to last longer, I cut her short after a couple of minutes by pinching her very sore nipples.

"Owww, don't do that!"

"You forgot to say 'Sir', and you stopped without permission."

"Sorry Sir."

Showing her eagerness, she sucked my cock right back into her mouth and leaned forward until I felt the back of her throat pushing against my head.

"My, my, aren't you the eager little cocksucker. How about we do this my way then."

I grabbed her head with both hands and pulled her hard against me until I felt my cock slide down her throat. She instantly started gagging, so I stopped, but did not pull out.

"You better get that gag reflex under control right now. You can NOT puke in my office."

I felt her gagging some more, but less intensely. I gradually pushed myself all the way down her throat and then started fucking her throat in earnest. I knew she'd eventually need to breathe, but I wouldn't last that long anyway. Holding her head with one hand, I used my other hand to roughly pinch and twist her nipple. The feeling of her trying to moan around my cock sent me over the top. My first burst of cum shot right down her throat. My concentration wavered and she was able to pull away slightly, which she regretted instantly as my next burst came right at the back of her throat and ended up getting forced up her nose. I slammed my cock one more time all the way down, and shuddered as my orgasm gradually finished.

After much coughing and gasping, she grimaced and said, "Getting cum up my nose burns!"

"I'm sure it does. But you forgot, again, to say 'Sir'"

I slapped her cheek.

"Sorry Sir."

I couldn't help myself and started laughing.

"What, Sir?"

"You should see yourself, with your makeup a complete mess and cum dribbling out of your nose."

"Very funny Sir."

"Well I think so, and that's what counts."

She didn't say anything as my cum slowly dribbled onto her bunched-up top. Then she finally leaned back in the chair and said, "Sir, what about me? Don't I get to come too?"

Realizing that my status would change from "Sir" to "blackmailed guy" after this was all over, I was in no hurry. And I had barely done anything to her pussy yet...

"That's up to you. Can you come from fucking?"

That deer-in-the-headlights look returned, but finally she answered, "Yes, Sir."

"Excellent. Then all you need to do is earn my cock in your pussy, and I'll fuck your pussy until you come."

"Uhm... Sir, what do I need to do to earn your cock again? I don't think I can take any more on my breasts."

"Remember how you told me you really enjoyed getting your butt and pussy slapped? Let's see how you enjoy it with the belt."

My smile must have looked particularly evil, because she turned ghostly white.

"Sir, I don't know if I can take your belt on my pussy. How about you do twice as much on my ass?"

"But sweetie," I responded sarcastically, "don't you want my cock nice and hard in your pussy? I don't think any amount of spanking your ass will do it for me. But hurting your pussy will definitely do it."

Nervously looking at me, she finally responded, "Okay Sir, but please go easy on me."

First I untied her hands and pulled her top off. God, she looked gorgeous topless, with red marks all over her chest. After untying her ankles, I had her bend over my massive desk. I tied her up with her arms stretched out in front of her and secured to the opposite side of the desk. Admiring my handiwork, I traced my fingers from her hands, down her outstretched arms, to her face. I smeared the leftover cum and spittle over her face. As I continued down her back, I realized she was quite comfortable resting on my smooth desk.

"This won't do, here lift yourself up for a moment."

As she lifted her chest off the desk, I slid my keyboard under her.

"Now you can lie down again."

Her sore breasts squishing into the keys was clearly very uncomfortable.

"That looks much better!"

Her grunting made me smile.

My hands made their way down her torso, stopping for a squeeze of each toned buttock. "Girl, you really don't have an ounce of fat on you. Good thing I'm not spanking you with my bare hand. My hand would end up bruised!"

I ignored her pussy for now and continued down her legs. Her wiggles indicated she was enjoying the attention. I eased her legs apart, until her ankles were all the way against each leg of the desk. Then I tied them in place.

"This should do nicely. I noticed that the way you're built, your pussy is quite exposed like this."

I laid my arm flat against her lower buttock. Sure enough, right between her buttocks, my arm pressed against her pussy.

"You know what that means?"

"That you'll have to be careful not to hit me there with the belt?"

"Ha! No, that isn't what it means at all. And you forgot to say 'Sir'."

With no warning, I gave her a smack right where my arm had been, across both butt cheeks and her pussy. Her sudden inhale told me this was going to be a lot of fun.

"No, what this means is that I don't have to turn you around to belt your pussy. I can do both your ass and pussy from the same position."

"How convenient," she said with an eye-roll.

"You're really not very good at remembering to say 'Sir'."

I gave her a smack straight up between her legs. It wasn't very hard, but with her legs spread out like this I must have made contact with her clit because she cried out.

"Sorry Sir!"

I started with a warmup. Not really counting, but after roughly a dozen mild hits with my belt, her whole rump and upper thighs were a light shade of red.

"Now that your skin is warmed up, let's give you some proper lashes, shall we?"

"Yes... Sir," came her halting response. I laid down nine strong hits, three on her ass above her pussy, and three on each upper thigh. She whimpered for each one.

"That wasn't so bad now was it?"

"No Sir, it hurt, but not as bad as my breasts."

I lightly stroked her pussy lips.

"How do you think it will feel here?"

"It will hurt a lot more, Sir."

"I imagine it will. Especially if I arrange your lips like this."

I stretched her pliable inner lips until they extended well outside her pussy, and then I carefully arranged them to be as open as possible. I marveled at all that pink, wet flesh that was about to get lashed.

"I'll start with five lashes."

"Please be gentle, Sir."

My answer was a direct hit across the center of her pussy. She shrieked and arched her ass up. I gave her a moment to process the pain, and then followed with two more hits in the same spot. This caused louder shrieking. I felt myself starting to get hard again, as I laid down two more hits slightly above and below the previous ones.

"There! Now your pussy is nicely warmed up! Wasn't that nice of me?"

"Thank you, Sir."

That sounded surprisingly like she was not being sarcastic. I'm not sure why I felt like she deserved a reward, but I slid a finger into her and smeared her wetness over her clit. Then I worked her clit in long, firm up and down strokes until she was moaning loudly.

"Okay, back to business."

She had become very relaxed on my desk, but now I saw her tense up. I gave her pussy three hard slaps with the belt. Pausing for just long enough to make her worried, I then hit her three more times in the exact same spot, right in the middle. This caused the loudest screams yet. I considered tossing the belt and just plowing my cock into her, but like an addict craving more, I kept going.

When I heard her sobbing I became concerned that I'd gone too far.

"Please Sir," came in a very small voice between sobs, "don't stop."

"You are quite the impressive little masochist! Okay babygirl."

I kept going. A few whimpers and sobs later, I checked in again.

"Has babygirl earned my cock now?"

"No Sir, not yet. Please, some more on my thighs."

I was pleasantly surprised at discovering how much she was getting out of this. I added three lashes to each thigh, starting right below her pussy. After listening to her quiet sobs turning into soft moans, I added another three on each side, reaching down to just above her knees.

"I'm ready, Sir."

Without hesitation, I dropped the belt and pushed my cock all the way into her wonderfully wet and oh-so-tight cunt. Leaning against her, I closed my eyes and realized I was in heaven.

Fucking Barbara was the best sex I'd had for years. I'd never had sex with a teenager before so I didn't know if all 19 year old pussies were this tight, but Barbara's certainly was the tightest I'd ever experienced. I started with long and slow strokes. We both had our eyes closed, heightening our awareness of the intense sensations. As I picked up the pace, she became more vocal. Gradually her high-pitched grunts and moans morphed into a litany of "yesyesyes, please Sir, oh, yyyyyesyesyesyes!"

"Can I come in your pussy?"

"Yes Sir... Mmmm, yes,... I'm on... mmmm... the pill."

Even better. Although I was in no hurry. I knew I could hold out for quite a while, since I'd come only half an hour earlier. She, on the other hand, was clearly not going to last long. I opened my eyes and enjoyed the sight of her writhing and pushing herself against me on each stroke. Then she suddenly arched up and froze, and let out an almighty moan. I sped up and slammed into her even harder, over and over while she shuddered and convulsed in the throes of her orgasm.

As I felt her pussy relax around my cock, I pulled out just enough to slide my hand between us. Finding her clit, I pinched it lightly and started massaging it through her hood.

She tried to pull away from my fingers and said, "Oh Sir, thank you, but I can't, I get so sensitive after I come."

"Really? Interesting."

I massaged her clit harder.

"No, really Sir! This is too much for me!"

"I'll stop as soon as you come again."

Pulling back on her hood, I started rubbing her clit directly. This brought a sharp squeal and a desperate attempt to pull away. Her gyrations caused my dick to fall out. I used my free hand to grab her pussy, attempting to hold her in place. Even that wasn't working too well, so I forced a couple of fingers into her pussy and my thumb into her ass, and pinched. That finally made her give up and accept my attack on her clit.

"But you have to tell me whenever you're close."

"I'm already close, Sir."

I immediately stopped, then swatted her clit and pussy a few times with my hand, and then returned to aggressively fucking her. Oh, this felt amazing!

I repeated this cycle with her at least half a dozen times. Each time switching between fingering her clit and fucking her pussy, with slaps to make her last longer. Eventually I found my orgasm nearing, and this time I just kept pounding her pussy after she warned me she was close. Her moans got more incessant and I started adding more of my own. Feeling her sudden tightening around my cock sent me over the edge. I shot my cum deep into her cunt as she buckled and shook under me. I had thought my earlier orgasm fucking her throat had been impressive, but this one was far better. I guess I'm an old-fashioned guy: a woman's pussy is best.

Exhausted from all the fucking, I finally flopped on top of her and simply said, "That was amazing."

"Thank you Sir. Same here, I've never had sex this good before."

"You really should rewrite that paper, you now have material for a far better story."

"Anything would be better than that crap. Sir, I hope you don't think I really write like that, that was just an excuse for me to set up this whole situation."

"Ah, I see."

And all of a sudden, I did see. My guess was probably too good to be true, but I could find out right now. I stood up and pulled my limp dick out of her.

"Lift yourself up so I can slide that keyboard from under you."

She gladly let me remove the keyboard, which had left deep marks across both her breasts.

"Sir, please untie me."

"Not just yet, there's something I need to check."

I sat down at the keyboard and unlocked the monitor. Her document was still open. I picked a random sentence from it ("you get three minutes to give me a blowjob and do the best you can to make me cum.") and googled it. Bingo.

Seeing my goofy smile made her worried.

"Sir, what are you doing?"

"Plagiarism!"

"What?!"

"Pure and simple plagiarism. You copied the whole thing from this poor slob in Finland. You realize I can get you expelled for this?"

This shocked her, but only briefly.

"Hold on, have you forgotten about my recording? If you get me expelled then I'm definitely getting you fired!"

She had a point. That fucking recording. I picked up her phone and gave it an angry stare. The screen lit up with it's usual message: "Press home to unlock." Yeah, if it were that simple, but of course it had to be her thumb. Wait a minute...

I walked around the far end of the desk and put the phone down next to her tied up hands.

"I guess there's not much I can do," I said dejectedly. I reached for her wrists, and I could see her quivering with anticipation of finally being untied. But then I grabbed her thumb and lightning fast pressed it on the unlock button on her phone.

"Yes! It worked!"

She looked perplexed, but then she realized what I had just done.

"Shit! No! Untie me right now and give me my phone!"

"Not bloody likely!"

I sat down with her unlocked phone, looking smug as pie. Opening the app she had used, I found the recording right away. I hit delete, and got this lovely dialog box which I read out loud to her:

"This will delete the recording from your phone. Do you also want it deleted from cloud storage and any synchronized devices? This action cannot be undone."

"What do you think Barbara, should I click on 'Yes'?"

"You bastard!"

"I'll take that as a 'Yes'!... All done!"

I put the phone down right in front of her nose and leaned back in my chair.

"Ah, this feels so much better. I'm sorry to disappoint you dear, but you won't be getting any money from me. As for your A grade, that all depends on how well you do in my class."

"Fuck you."

"I'll be expecting your rewrite on Monday, of course."

Gazing at Barbara's lovely body and cute face, I noticed my cum dribbling down her thighs and a bit still on her chin. Hell yes, two can play at this blackmail game.

"And about your plagiarism, I promise to not tell anyone... so long as you come back here same time next week."

I traced a finger down her back. Laying my hand on her buttock, I gently tapped her asshole.

"We have so much more to explore. You know, it wouldn't be fair to cram it all into one session. Here's what we'll do: you come to my office at this time every Friday for the rest of the semester. Agreed?"

She swallowed, and then responded very quietly, "Yes Sir."