Blackmailed by His Student

The knock on my office door startled me. Thank heavens I hadn't pulled my cock out yet. Could they have heard the loud moaning from the porn I was watching? Probably not, the doors and walls here in the old English Lit building were thick and solid.

"Come in."

"Professor Oleson, I hope I'm not bothering you? I'm sorry that I couldn't make it to your office hours earlier today, but I really need to talk with you."

I recognized her from my Creative Writing course, but it was still early in the semester and I couldn't place her name. I did remember, however, that she had asked some very clever questions in class, but then handed in a piss-poor assignment.

Giving her a rueful smile, I said, "I hope you don't assume all professors have nothing better to do on Friday nights, but in this one case you're correct. Please come in and have a seat."

She quickly closed the door behind her and sat down awkwardly on the edge of the chair in front of my large desk. Like all the furniture in my cramped office, the desk and chair were old and made of sturdy wood. They say dog-owners end up looking like their dogs; I contend that the same applies to academics and their offices. As a typical middle-aged professor in a tweed jacket, I was indeed starting to look sturdy and a bit worn around the edges. And my brown skin tone harmonized splendidly with the dark wood.

She, however, must spend her days in a very stylish and modern office, with black and white furniture. Her short, dark hair and dark lipstick made her look rather severe, especially with her contrasting porcelain-white skin and slender build. Combined with her black crop-top and steel-gray miniskirt, the overall effect was quite stunning.

"I'm Barbara, from your Creative Writing class..." she blurted out.

Ah, quite the coincidence. Another Barbara. Did that mean the "woe is me" meowing would come next?

"...and I was surprised and upset to see my grade on the latest assignment."

Oh boy, and now she's going to list the reasons why she really needs a good grade in this course.

"I realize this is still early in the semester, but this course is important to me and I really want to get a good grade in it."

"Give me just a sec while I pull up your story. Now, as you know, the assignment was to write about a makeout session gone bad... Yes, here it is. Now I remember. It's true, I gave you a C minus, but quite frankly that's a very fair grade."

"But why? I'm sorry if my writing was rather explicit, but I was proud of myself for pushing my limits. I thought you wanted us to push limits in our writing?"

"Absolutely! This assignment is all about getting out of your comfort zone. And I have nothing against explicit writing, so long as it's done with feeling. But that was exactly what your story was missing."

As I skimmed through her writing, I was amused by how it was just as bad as the writing the other Barbara had done for the same assignment a year ago. And then she had sat in that same chair, defending her work just like this Barbara. But surely things wouldn't work out the same way again?

I continued, "Here for example in the third paragraph: 'He kissed me for a few minutes. Then he reached for my breasts. After squeezing my breasts through my bra, he reached around behind me. Then he unhooked my bra.'"

I gave her a determined look, and noticed that she had started blushing.

"Where are the descriptions of how this made you feel?!? Not one word so far about whether you enjoyed his kissing! Before we even get to discussing your breasts, there are all these unanswered questions: Was he a good kisser? Did he turn you on? Had you wanted him to kiss you? Were you even ready to be kissed?"

Barbara was looking at her lap and fiddling with the strap of her purse. That looked like an expensive purse. In fact, it looked just like the Bottega Veneta purses I'd been researching for my own writing. Those could cost thousands of dollars. So she was clearly not short on money.

Getting no response, I continued, "And then you describe how he pawed your breasts and pinched your nipples. But nothing about how that felt. Did he pinch hard enough to make it hurt? What was your reaction? Were you upset, scared,... or turned on by it? And even though you're writing in first person, you could have speculated about his motivations too. Was he just fooling around and teasing you, or does inflicting pain turn him on?"

Blushing more, she finally responded, "I understand what you're saying and I'm sorry I didn't include that in my writing. I was a bit caught up in... in writing... oh, I might as well tell you. I was writing about experiences I've never had."

That caught me by surprise. I had told the class that they should weave their own experiences into their stories, if they felt comfortable with that. Hers had been one of the most sexually explicit stories in this assignment. It had made me wonder if she was describing actual events, but it was so badly written I couldn't tell.

"That would make the assignment a bit more challenging for you, but that's what research is for. And I could tell you didn't do your research. For example in this part: 'I grabbed his uncut cock and pulled on the foreskin to get him hard.' Do you know any uncircumcised men, and did you check with any of them if foreskin-pulling would make them hard?"

"No, I'm too shy to ask questions like that."

"I can give you a bit of research for free. Pulling on a guy's foreskin does not make him hard. Pulling the foreskin back is another story, since that can be a precursor to inserting the cock somewhere nice. And yes, I'm uncircumcised, so I know what I'm talking about."

I realized right away that I'd gone too far. This was no longer me teaching a student the basics of creative writing. It was me being a horny bastard alone in an office (and probably alone in the building) with a strikingly beautiful young woman. How old though? My first guess would have been 22 to 24, but maybe it was the makeup. Could be as young as 20.

"I'm sorry Barbara, that was unprofessional of me. I hope I didn't make you uncomfortable."

She perked up and looked like she had just made up her mind.

"That's okay. I really appreciate how you are explaining this to me. This is really helpful. I bet I could write a much better version now, especially if I did a bit more research. If I turned in a new version on Monday, would you please regrade it and throw out the old one?"

"Let's just focus on getting your next assignment in good shape. I don't allow rewrites on these assignments."

"Oh, but I can't get a good course grade with this C minus! I really want to get a good grade for the course. Also... this girl who took this class last year told me you let her do a rewrite in similar circumstances. Her name is also Barbara."

I froze. How much had Barbara told her? I couldn't believe Barbara had told anyone! Despite my shock, I found myself staring at this Barbara's lips. My dick twitched at the memory. But what if I was misreading the situation, and this girl wasn't offering anything in exchange for the second chance?

"Interesting. And what exactly did this Barbara tell you?"

"She said that she had asked you nicely, super nicely, and you had agreed to accept her rewrite. She ended up getting an A minus in the class."

Yeah, "super nicely" was one way to put it. Was I really getting another opportunity? From an even prettier Barbara? This was too good to be true. I needed to be sure.

"We've only been talking for a few minutes. No offense, but do you really think you've picked up enough to drastically improve this writing?"

"I was actually hoping we could spend a little more time right now."

She briefly caught my eye and gave me her first smile since entering the office, but then she immediately looked down and demurely fiddled with her purse.

My eyes traced the curve of her long and slender neck, her tight top covering petite breasts with no hint of visible bra lines, the tantalizing strip of exposed skin below her top, her very elegant skirt, her long nude legs, and expensive-looking black flats. I was past caring if my judgement was clouded, I was ready to jump in.

"Okay. But if we do this then you have to prove to me that you are dedicated to improving your writing. I can help you with the research, but you need to impress me with a willingness to learn."

Her smile lit up the room.

"Oh, thank you so much! I promise to try my best!"

"Let me start with learning a bit more about you. Tell me, was any of this story based on your actual experience?"

"I've had very few sexual experiences. I know what it's like to make out with a boy, and I gave a blowjob once, but that's it. Everything beyond that was just speculation."

I stood up slowly and started pacing behind the desk.

"Let's start with a simple composition exercise. Describe that blowjob in three sentences."

Her eyes widened, but she didn't object.

"This was in my dorm room with me fully clothed on my knees and him standing up. I knew we didn't have long because my roommate was coming home shortly, but he kept moaning and pushing the back of my head to get me to take it deeper. He came while pulling out of my mouth, which made it messy to clean up."

"Nicely done! Three sentences that captured the essential information. Now let's dig a bit into your emotions. Did you enjoy it? And what aroused you most? Was it the sensation of his penis in your mouth? Or was it knowing the pleasure he was getting? Did you like the helplessness when he pushed your head?"

She licked her lips before responding, "I think I was too busy figuring out what I was supposed to be doing, so I wouldn't say I really enjoyed it. But I definitely didn't dislike it. I was more aroused by the pleasure I was giving him than by the sensation of his penis in my mouth."

Shifting in her seat, she suddenly looked nervous again.

"I liked the helplessness. Him holding my head. I remember wondering if he would've gotten more demanding and forceful if we had continued."

I stopped pacing and leaned against the desk. I had an idea.

"See? Now we're getting somewhere! Now the reader is learning something about you. We've learned that you're turned on by giving pleasure, and from being helpless. It sounds like you're a natural submissive when it comes to sex. So that's where you should focus your research."

She looked curiously at me.

"Here's your chance to prove to me how motivated you are about this rewrite! Let's do some research right here and now. We are both fully clothed so this is perfectly safe. How about I tie your hands together to see if you find that arousing? In other words, let's test this theory that you're naturally submissive."

Glancing down at her hands, Barbara blushed furiously. Oh man, I hoped I hadn't laid it on too thick. She was either going to agree, or run out of my office...

"Really? You think that would be okay? I mean, I'm willing to try, if you think it would help me learn about myself and better my writing."

"Excellent! Now let me find that spare tie that I keep here somewhere..."

I rummaged in drawers until I found the old necktie. Then I walked behind her chair, where she's still sitting right at the edge.

"Now please put your hands behind you."

She quickly put her hands together, pressed between her back and the vertical chair slats. At the same time, she separated her legs and tucked her ankles behind the front legs of the chair. I tied her wrists together, fairly tight. She took a deep breath as I paused, then I threaded the loose ends through the slats and tied her to the chair.

"How does that feel?"

"It's tight, but I like it. I like the idea that I have no control. For example, if you were to touch me at all, I wouldn't be able to do much about it."

I walked around in front of her and sat against the desk, fairly certain that the bulge in my pants must be noticeable. But then she continued, "Or, if I was to redo that blowjob I was talking about earlier, I wouldn't have to worry about what to do with my hands if I were tied up like this. And he could have just thrusted into me, deciding how deep down my throat to go."

"Interesting. Let's review what you just said, starting at the beginning. What you're saying is that if I do something like this..."

I reached my hand to her face and gently stroked her cheek.

"...then you enjoy it more because you can't prevent it?"

"Yes, exactly!"

"Hmm, I wonder if that translates to things that aren't inherently enjoyable. How about this?"

I reached behind her head, grabbed a handful of hair and tugged back sharply. She gasped and arched her back. As I eased my grip, she looked at me with a twisted smile.

"That felt good. Surprisingly good. I especially liked the contrast between the nice touch and the harsh hair pull. It made me excited about what's coming next. Something about you being unpredictable and in control... is definitely turning me on."

Taking that as a cue to act without giving her advance warning, I knelt in front of her. That drawer with the neck tie had also contained a pair of long shoelaces. I tied her ankles to the chair legs. This was truly the point of no return: With no warning, I reached for her breasts and started kneading them through the smooth, black top. At first, she looked taken aback, but soon she started relaxing and closed her eyes. My guess had been right, there was clearly no bra under there. I kept going till her nipples were rock-hard. Then I stopped suddenly and slapped her cheek.

Her whimper was followed by a soft moan.

"Be honest with me, did you find that arousing?"

"I found that really arousing. The fact that I'm so helpless and you can do whatever you want to me is turning me on. A lot!"

Circling her like a predator around prey, I traced my fingers up from one breast, up her neck, around her back, and down to her other breast.

"I assume you masturbate, but have anyone else's hands touched you down there? Boy or girl?"

"I do masturbate, usually once a week-ish. But no, no one has touched me down there."

I returned to her front, and knelt down again.

"Once a week? When I was your age I must have been doing it every day. How old are you anyway?"

"I'm 19. I used to do it more but I found that if I make myself wait in between orgasms, they feel a lot better. I like to edge myself in between and build up sexual energy."

She shivered when I laid my hands on her naked thighs, right below the hem of her miniskirt. I was ecstatic at the thought of being the first to finger this gorgeous teenager. Very slowly, I slid my hands up her thighs.

"How long has it been since your last orgasm?" I asked her.

"It's been over a week."

My hands were now most of the way up, with my thumbs pressed against the soft insides of her thighs. She was breathing heavily.

"It'll be my pleasure..."

Thumbs now just an inch from her crotch.

"...to help you find release."

As both thumbs touched heaven, I was amazed to discover moist, smooth skin, with no layers of material in the way. Her reaction was as if a wound-up spring had been freed. Her back arched and her hips sprung up. This caused her purse to swing around and her phone to go flying out of it and onto the floor. It landed face up. On the screen was a blinking red recording symbol, and a timer counting up minutes and seconds.

I pulled my hands back and stared at her phone. She opened her eyes and looked at me, not yet comprehending why I stopped.

"Are you recording me?!?"

I jabbed at the phone to stop the recording, leaving a damp thumbprint in the middle of the screen from her own juices. Thrusting the phone inches from her face, I bellowed, "Why were you recording me?"

After the initial shock wore off, a sly smirk grew on her face.

"Isn't it obvious? To blackmail you!"

I slammed the phone on the desk.

"You little rat! But you weren't very smart to let me tie you up, because now you can't stop mer from deleting the recording."

"No, it's not that simple. This app saves directly to the cloud, so it's already safe in my account."

I must have looked comically upset, because she started laughing.

"Besides, my phone is locked so you can't delete it. If you don't do as I want, I'll send the recording to the Dean and get you kicked out."

I couldn't believe I had been tricked! I knew she was right. If this recording got to the Dean, I'd be out of here and who knows if I'd find a job anywhere in academia again. I resisted the urge to yell at her.

"What do you want from me?"

Her smirk was now ear to ear.

"I want a guaranteed A in your class. And I'm not doing a stupid rewrite. You just change my grade and then make sure to give me A's on every assignment from now on."

What a relief! That wouldn't actually be all that difficult.

"Okay, if I agree, is that it?"

"Oh no, I also want $5,000."

Fuck this shit! So this was going to cost me thousands of dollars? Sure, I could cover it from my savings, but that seriously sucked. What the hell could I do?

"Five thousand dollars?! What, so you can buy yourself more expensive purses?"

She glanced at her purse.

"Oh, I didn't buy this one. I stole it."

She stared at me with an intensity I hadn't seen before, and continued, "It was your suggestion in class that we should do more stuff outside our comfort zones. I liked that. So I stole this purse. Which was fun, but I needed to go further. Then I remembered what Barbara had told me about her blowjob with you. That gave me the idea to blackmail you. I turned in a deliberately shitty assignment, figuring you couldn't resist another blowjob when you found yourself in a similar situation again. And now I have a recording of the whole thing, so you'd better do as I tell you!"

"Okay, you miserable cunt, how about this instead. You watch me right now transfer $4,000 to your account and at the same time I watch you delete the recording."

It didn't take her long to reach a conclusion.

"Okay, deal. So long as I still get my A!"

I sneered at her, "You'll still get your A."

I reached for her ankle to untie her, but she stopped me.

"Hold on, leave me tied up just a little longer. You need to finish what you started."

"You can't be serious."

"I'm absolutely serious. The thing I told you about not having come for over a week, that's absolutely true. Now kneel before me and continue where you left off. And remember, I like it rough!"

If just on principle, I can't say no to a gorgeous girl who asks me to finger her. Even if she's an evil blackmailer. So I got down on the floor again and started sliding my hands up her inner thighs. I couldn't decide whether to get this over with as soon as possible, or to prolong it and take advantage of her being tied up. The greedy bitch sure deserved that. Fuck it, I was equally screwed either way. I might as well have a bit of fun with her.

Touching her wet pussy caused her to arch her back again, and push herself against my hands. I gently rubbed up and down along the sides of her outer labia, carefully staying away from her more sensitive bits. Let's see how frustrating I could make this for her.

"That's nice, but now start playing with my clit."

I pulled up her skirt so I could see what I was doing. I've never met a pussy I didn't think was beautiful, but hers was fantastic. So smooth and very wet. And her inner lips prominently poked out, which is an instant turn-on for me. I lightly pinched her hood and slowly pulled it up and down.

"You mean like this?"

"Mmm, oh yes, keep doing that."

I let go and said, "No, I don't think so. That would make you come and then you'd just want to leave. Besides, didn't you say earlier that you were turned on by me being unpredictable and in control?"