DISCLAIMER #2: Themes of this story revolve largely around humiliation, black mail, and voyeurism. If you are not interested in these themes, please do not read. Of course, in real life much of what is portrayed in this story is despicable, and should not be tolerated under any circumstance. Hence, why this is a story of fantasy, and should not be taken seriously.
DISCLAIMER #3: While themes of the story certainly can be dark, I do try to keep things light with a certain “comic book” style. Again keep in mind that this is a work of fantasy and not everything will be fully realistic.
Enjoy! Please leave comments on what you want to see next as much of the following chapter is a work in progress. Cheers
My life was almost like a comedy at this point. I’m a single, 63 year old high school Math teacher at the worst school in the district. My best days were clearly behind me. Unlike most teacher’s with as much seniority as me who would have their pick of what class they would like to teach, I didn’t have such privilege. The asshole of a principal, made me teach junior remedial math, which was filled with the 10 dumbest kids in the school. These kids really were hopeless.
I couldn’t much blame the principal though. I knew how him, as well as the rest of my ‘colleagues’ viewed me. They knew I was a socially awkward pushover who would accept whatever demeaning job they gave him.
I was on the verge of falling asleep, when I heard a stack of papers hit my desk.
“I’m all done my assignment Mr. Wilson!” a cheery voice squeaked
I looked up at Katee Owens, who was at this point, the one highlight in my life. She was the lone girl in the small remedial class, and really looked like she didn’t belong. She was the only one in the class that actually cared about her education, and had a genuine desire for learning. She was hard working, and always turned her assignments in on time.
But no, this wasn’t what I meant when I said that she was the one highlight in my life. What I meant was that she was drop dead gorgeous. She was a petite brunette with light skin with some freckles on her cheeks, big hazel eyes, and striking facial features.
I met her eyes as I took the papers from her “Oh that’s great Katee.” My eyes quickly dropped down to her bust. Even in a full sleeve sweater, her tits seemed to pop out impressively for a girl with such a petite frame otherwise.
“Thanks!” She beamed, before turning around and prancing to her desk. I took a moment to appreciate her round ass jiggle up and down through her jeans as she walked back to her desk. I looked around and saw a few of the other boys checking her out as well.
“Those bastards” I thought to myself, at least they could try to pick up a girl like that and fuck her. I could only day dream.
I looked down at the paper and chuckled. Despite trying hard, the poor girl just had no clue. I figured she must have a learning disability or something. I could tell by first glance that even the simplest problems on the first page were horrendously incorrect.
I parked my beater of a car in the old apartment building that I lived in. I made my way up to my studio flat. I got undressed and went straight to the computer. Despite the life I’m painting to you, I’m actually not that poor, from a financial standpoint, atleast. I lived below my means, allowing me to invest diligently in the stock market, which has allowed me to build up quite the nest egg. Having no children, family and few friends, I didn’t really have much to spend it on either.
I did find an interest in technology as I lived through the dot-com era, and as a result have become quite savvy for a man my age. I spend most significantly on my home computer, and related accessories.
Being as tech savvy as I was, and as desperately lonely as well, I inevitably grew an increased affinity to online porn. Through my years, the perverse fantasies progressed, and I soon crossed over from mainstream porn to porn found only on the dark web. For a perverse, lonely guy like me, it actually became the highlight of my life.
The fantasy of late for me, of course revolved around the sexy jailbait teen in my class. I would browse the web for as long as it took to find a girl that looked like Katee, doing depraved acts. I would pretend that it was my little student that I was watching.
Today I was having a hard time finding some new videos that fit this fetish. As I became increasingly horny, I became increasingly frustrated. As hot as the girls that I would find online were, none of them compared to my Katee. Nothing was close to the real thing.
Just then, a thought hit me. What if I could film Katee in real life? At this point in my obsession, even ordinary footage of Katee, my dream girl, beat some cut-rate amateur doing even the most depraved acts.
I realized that I could perhaps get some more realistic footage of her myself to fuel my fantasies. It would be a gutsy move, but hey, as an old loser with no social life to speak of, what did I have to lose!
A week later, I came home to a parcel in my mailbox. I practically ran upstairs to my flat and opened it up.
This was perfect. I had to pay a pretty price, but it was going to be worth it. I had opened the package to find five high definition spy cameras. You guessed it, I was planning on planting these bad boys to get candid footage of my girl at school.
I got to work the next day 2 hours early. I moved the desks around so that Katee’s was front and center. I spaced the desks far apart, so that no other kids would get in the way of the cameras. I placed a camera on all four walls and focused them in on Katee’s desk. I then stacked a couple desks on top of each other and climbed on top and placed the final camera on the ceiling in hopes of getting a direct shot down Katee’s cleavage.
I popped my laptop open to ensure the cameras were working. The quality was stunning. I zoomed in each of the cameras using my laptop to focus right in on Katee.
I gleefully waited for the class to start. I practically started to salivate as I saw Katee walk in and take her seat. I explained to the class that I shifted tables around to increase productivity. They either bought it or just didn’t care, and they took their seats.
I put on a pair of dense sunglasses, explaining to the class that I have developed an eye problem. Again, they didn’t care. Of course, this was all so that I could stare at Katee as much as I wanted without anyone being the wiser.
Today, Katee was wearing a pink spaghetti strap top, exposing her cute shoulders, neck and most of the upper half of her back. Unfortunately the front part didn’t plunge too far down to show her cleavage. Her tits projected proudly forward as usual. Katee was a good girl, she didn’t really dress slutty like a lot of the other girls at the school, much to my dislike.
After doing 15 minutes of obligatory didactic teaching, I asked Katee to hand out today’s assignment and watched her sexy body walk up and down the room. I drooled watching her tits and ass bounce with each step she took. Each of the boys checked her up and down before taking the paper from her. She seemed too oblivious to notice.
Class seemed to fly by as I was lost in reverie watching Katee unabashed throughout the hour. The kids ran home, and I did too almost as fast. I quickly undressed and logged on to my home computer to watch the footage I had snared.
The footage was flawless. I couldn’t believe I was able to look at this teen goddess from all angles as much as I wanted. I felt like I was powerful for once in my life. I cropped out clips that were especially racy. The best clip from today was when Katee handed her assignment to me and bent over at my desk, her top crept lower for just a couple seconds, exposing a modest bit of her generous jailbait cleavage to the camera at the front wall. I saved this, and eventually masturbated to my dream girl’s youthful round tits.
I continued to collect clips throughout the week. I was putting together quite the compilation of my sexy jailbait obsession.
My favourite was when she dropped a pencil, and then got on all fours to look for it and pick it up. Her mid length skirt rode up her, exposing some of her sexy inner thigh. The front camera caught her delicious tits spill forward, exposing more of her cleavage as she was wearing a white blouse with one button undone. I masturbated to this clip furiously.
While these clips fed my perverse fantasy more than any porn did, it also fueled my obsession. After seeing more of Katee, from all angles, I was feeling more lustful than ever. I was feeling that I needed to take a risk to get more of what I wanted. I knew I had to take this to the next level.
After perving out looking at Katee all class, I called her to my desk at the end of the day.
“Yes Mr. Wilson?” she innocently beamed.
I looked her up and down. She was wearing a simple pink T-shirt that clung tightly to her bust and ended an inch or two below her waistline. She wore black yoga pants, that modestly showed off her juicy ass.
I talked to her sternly. “Katee I’ve looked at your assignments so far.” I said as I handed them to her “I’m afraid you are failing the class very badly thus far.”
Tears immediately began to form in the teen’s big hazel eyes
“W-What?” She whimpered “But I’ve been trying so hard.”
A part of me felt bad for her. But a part of me was happy as I knew I had her right where I wanted her.
“Now now Katee, no reason to get hysterical. It’s only the beginning of the year, there is time to turn it around. But I’m afraid you’re going to need serious help.”
“Like a tutor?” she sniffled “some of the boys in class offered to tutor me for free!”
I chuckled. Like any of those idiots would be able to help her.
“No Katee, I’m afraid you need a lot of help. You need professional help, from an expert.”
She looked up quizzically
“Mr. Wilson, would you be able to help me?”
“Well I guess I could Katee, but I am a very busy man. And this would have to be after school, an hour and a half each day, I don’t know if I have time.”
I looked down at her.
“Please Mr. Wilson.” She begged “There is no way I can fail this class. If I fail then my dad won’t let me go to camp with my friends!” she went on to explain “That camp is the only place I feel happy. It has all my old friends from my old school.” She whimpered
I feigned consideration.
“Katee, I guess I could, but would your father be able to afford $100 dollars an hour for tutoring? That is the going rate for professional help. After all, after school end each day, I’m no longer your teacher, I am a professional tutor.”
Katee looked deflated “No sir, he is working two jobs and is barely able to make ends meet.”
“Oh well, I’m sorry to hear. Because you know, if you work with me, I would personally guarantee that you pass the class.”
With this she put her hands together “Please Mr. Wilson, isn’t there something we can work out!?”
I paused for seemingly forever. She looked at me.
I knew that I would never have this opportunity again. I went full steam ahead.
“Well Katee, if you really want to attain my services, you’re going to have to do something for me.”
“OK anything sir. Do you want me to wash your car? Clean your house?”
I paused, pretending to contemplate those options.
“You know Katee, my time is quite valuable. I can hire someone to wash my car and clean my house. You’re going to have to offer something unique.”
“Anything sir, Anything!”
“Well, if you say so.” I paused “Katee, I will tutor you an hour and a half each day, on one condition.”
“Yes??” she yelped
“Katee, if you strip to your underwear for this tutoring session, I will waive the fee.” I smiled, but on the inside I was dying. I was either going to lose my job, or was going to have the time of my life.
“What, no.. That’s gross, and you’re old.” She said softly, she was clearly petrified and confused.
“Ok dear, suit yourself.” I said coldly putting the papers back in front of her “as you can see, you are averaging 13% on your assignments, a pass is 60%. I wish you luck passing this class Ms. Owens.”
I saw her look at the papers, and almost break down and cry again. I sensed an opportunity.
“Or, take my tutoring, with my conditions, and I will guarantee you pass.”
She looked up from the paper to me, and back again.
“Think about it, would you rather go to summer school, or summer camp” I cooed
She contemplated this deeply. Finally, she looked at me.
“Fine” she whispered.
I practically felt like screaming in joy. I knew I needed to strike twice.
“Smart girl.” Go ahead then, and we can start.
She looked reluctant again.
I tapped on my watch. “We have until 5:30, time is ticking.”
She reluctantly stood in front of my desk. I could see her arms shaking as she reached for the hem of her T-shirt. She slowly grabbed the hem and started to peel it up. I groaned as inch by inch I saw the soft flesh of her teen tummy exposed.
The shirt almost got stuck on her bra, but with a tug she got it over, revealing her big round tits encased in a lacy blue bra. Her tits looked magnificent, even in a cheap bra, they looked like a masterpiece. They jiggled up and down with each movement. She took the shirt off completely.
I stuck out my hand, and gestured for her to hand me her shirt. She whimpered as she gave me her shirt, she knew she was stuck now. I looked at her sweet face, she was blushing, and looked terrified.
“Very nice, now the pants.”
She looked at me, begging me with her eyes to spare her. I was unforgiving. I watched as she peeled her yoga pants off her ass and legs and stepped out. She was had on ratty pink panties. I salivated at her youthful thighs and legs, now fully exposed.
“Very good Katee,” I took the pants from her. I put her clothes in a large drawer at behind my desk and locked it.
She was completely humiliated and was sniffling as tears were rolling down her cheeks. I told her to spin so I could look at her.
I salivated as she presented her panty-clad teenage ass to me. It was flawless. The panties were modest, and covered the majority of her cheeks, but still I could see the bare flesh of much of her luscious cheeks. Her cheeks bounced as she continued to spin and face me again.
“Good girl, this is going to be a great partnership Katee.” I sneered “Now lets get to work”
I spent the remaining hour teaching her basic math, going through work sheets with her starting with elementary level math.
Of course most of the time I would be leering at her panty clad jailbait body as she worked through the problems. I watched as her tits bounced each time she used her eraser to rub out a mistake. When she was into a problem, I felt like she almost forgot the predicament she was in, and almost started to feel normal.
Every 10 minutes or so I would have her stretch in various positions. I told her it was good for her brain to do this periodically, but her and I both knew why I was really doing it. I ogled her ass from behind as I had her touch her toes. And likewise, her tits as I made her arch her back.
Finally the time came to an end. I told Katee she did great, and then gave her her clothes back. She hastily grabbed her clothes and put them on. She quickly thanked me and then practically ran out of the room.
After she left, I immediately went home and masturbated furiously to the clips I had of her in her underwear from all angles, seeing her near naked teen body contorting in various ways. After masturbating the third time that night, I still wasn’t satisfied. I couldn’t get the thought of this teen minx out of my head. While I was ecstatic that my plan had worked and got to see her panty clad body, It was like the more I saw of her, the more I needed her, by any means necessary.
The next day, I couldn’t keep my eyes off of Katee. She was wearing a black turtleneck sweater, and, and blue jeans. However, I knew now more intimately what lied underneath. I was mentally undressing the teen in my mind, imagining what color panties she had on, and how her young tits looked in her bra today.
Katee, usually bright and chipper, was squirming around awkwardly in her chair today. She refrained looking at me. She knew that I was leering at her underneath my the veil of my tinted glasses.
I smirked as seemingly every few minutes, one of the boys in the room would sneak peeks at her. I knew that given the chance, every one of these Neanderthals would tear Katee’s clothes off of her and fuck her like an animal. It gave me satisfaction in knowing I had seen what lied underneath that sweater and jean, and they didn’t.
The class finally ended, and one by one the students left the room leaving only Katee behind. She slowly made her way to my desk.
“Ahh Katee, lovely sweater, time to take it off for your next lesson.”
She looked at me for a moment, before somberly taking off her sweater. I groaned as I saw her flesh revealed inch by inch as she peeled her sweater off of her. Today she had on a black polyester bra that was tearing at the right strap. That tit almost seemed to hang half an inch lower than the left.
I licked my lips, and then motioned to her jeans. I salivated as she stepped out of her jeans swiftly, revealing her round ass to me clad in some cheap black panties.
I looked her up and down, and smiled. She was looking down, again avoiding eye contact.
“Can we just start the lesson now?” she said quietly
“Well Katee, I’m afraid my price has gone up. I’m going to need the bra and panties as well today.” I sneered.
She looked at me and met my eyes for the first time all day.
“What? I can’t.. you didn’t say anything about me being naked. No one has ever seen me naked..”
“Well I changed my mind dear.”
She paused, before looking up at me fiercely.
“You know what Mr. Wilson, I don’t need this. I don’t care if I fail.. I would rather not go to camp then strip naked for a pervert like you!” she said with the most amount of conviction I have ever seen from her.
Luckily for me, I was prepared for such a response.
I looked at my desktop computer, made a simple click, and then turned the monitor her way.
“I was hoping it wouldn’t come to this dear.” I soothed
I watched as she saw the video on the monitor. It was compilation I edited late last night of her underwear clad body in various compromising positions. Multiple Clips of her perfect tits and cleavage bent over, and her round ass with her panties being sunken up into her ass crease were playing in front of her. Her eyes widened in fear.
I let the 10 minute video play as I spoke.
“One click dear, and this video is hitting the inbox of every student here, uploaded to every porn site online, and of course being sent to your poor old dad.”
I watched as tears started to stream down her face. The poor girl was petrified, understandably so. I watched as her dumb little teenage mind tried to come up with ways out of this.
“B-B-But you’d get in trouble!! You’d get fired and my dad would make sure you ended up in Jail.”
I had rehearsed for this. I smiled “You’re right dear, I would. But hey, I’ve lived a good life. I’m just a lonely old man. I don’t care if I go to jail, I have nothing to lose.
But YOU on the other hand, my dear you have your whole life in front of you. Do you really want to be known as a whore who stripped to her panties just to pass a Math class? You’d be ruined girl”
I paused before continuing. I knew my words cut her deeply.
“Just let me have what I want, do as I say, and all of this will stay between us. I get to see you naked, you get to pass the class and go to summer camp. And by next year, both of us forget that this ever happened.” I soothed
She thought about it. I could see her pondering. I knew she couldn’t believe that she was in this position, but I also knew that she really had no way out. Of course she could call me on my bluff, but the truth was I really didn’t care what happened to my life. At this point, the prize was worth whatever risk. I was so lustful for her, I really didn’t care about the rest of my life. I had to have her.
She replied softly
“Fine, but just for the rest of the school year”
I wanted to jump up in joy. But I kept my composure.
“Smart girl. Now get to it.”
I watched as she slowly reached for her bra hooks. With great trepidation, she finally unhooked her bra. I could see the release of tension on her tits the moment she unhooked it. She looked at me petrified, holding her bra in front of her tits.
With a sigh, she did so.
I almost came at the sight of her perfect teen tits. They were big, and must have been D cups, but looked even bigger as they contrasted with her slim frame. The flesh underneath her bra was pale compared to her the rest of her sun kissed skin. She had pink nipples. I was astounded how perfectly her big tits rested on her chest.
I motioned for her to come to my side of the desk.
She slowly did. I marvelled at her tits, now just a foot away from me. Instinctively I put my hands around her tiny waist. She pulled back, but I forced her in towards me with ease. I imagined that I probably had close to 150 lbs on her.
I wrapped my left hand around her waist, and with my free hand I stroked up her tummy and started groping her left tit.
“No please. What about tutoring!!” She pleaded as tears rolled down her cheeks.
I ignored her pleas, and started groping her tit to my pleasure.
“Please, a girl with tits like this doesn’t need to learn math. She just needs to learn how to be a perfect little slut.” I sneered as I played with her nipple, and squeezed her tits relentlessly.
I loved the youthful feel. It had been decades since I had big tits in my hands, and never as nice as this. At this point, I knew I was being driven into frenzy. Her pleas seemed like they were coming from underwater I was locked in on her. I pulled her in closer and engulfed her tit into my mouth. I sucked her jailbait teenage tit like a starving baby hungry for milk. It felt surreal, I couldn’t believe I was doing getting to do this with my dream girl.
With my other hand I instinctively started groping her luscious ass. It was doughy in my hand, but also resilient. I couldn’t help but give it a few sharp smacks whenever Katee tried to pull away from me.
I brutishly tore the teen’s panties off. The cheap fabric ripped easily, exposing her naked ass to me. I continued to grope her ass, now inching towards her anus. I smacked her ass every time she resisted, causing her to squeal and momentarily give in. All the while, I continued to feast on her delicious tits, leaving my slobber all over her neck and tits. I had truly transformed into a mindless animal, focused on one thing only.
My hands were both now on her bare ass cheeks, splitting them apart, squeezing them with all my strength. I instinctively made my way to her teen pussy with my right hand. Without a second thought, I inserted my finger into her pussy. She moaned in pain. I couldn’t believe how tight she was. Just two of my fingers were struggling to move in and out of her pussy.
With my other hand I made my way to her tight ass hole and started circling it. I gently inserted my index finger. She scream out loud and instinctively tightened her ass hole sphincter on my finger. It felt like I was in a vice grip, but I managed to keep advancing my finger. She gasped in pain with each inch.
My other hand was fingering her pussy mercilessly, gently causing her dry pussy to start to lubricate itself.
Here I was with her right tit in my mouth, biting her nipple, fingering her pussy and having my index finger knuckle deep in her tight asshole. I knew it was only a matter of time til my dick was about to explode.
She momentarily gave a sigh of relief as I let all of her orifices go. This was short lived as I picked her up and forcefully put her face down over my Teacher’s desk.
“Stick your ass out whore.” I said as I gave it a smack.
She did as she was told, she had no choice.
She spread her legs wide, and stuck her ass up off of the wooden table. Her back arched, as her tits we’re smushed against the cold table. I told her to look up and keep her face pointing towards the back wall at all times.
I wanted the camera on the back wall to get a good view of her sweet innocent face during this.
“Please no, Please no, not like this!!” She wailed.
I gave her several sharp spanks “Quiet whore.” I sneered.
I split her ass cheeks apart and forced my thick 8 inch cock into her teen pussy. I felt a pop, as she screamed in pain. My generous belly rested on her ass as I started to further impale her.
Luckily the annex we were in was far away from the school, so I was hopeful that no body would hear this. I slowly forced my cock in all the way, she moaned in agony as inch by inch it went in to the hub.
I grabbed a fistful of her thick silky brown hair and yanked her head back as I started to thrust in and out of her tight pussy. She was in agony, I was in heaven. Her tight pussy was like a warm vacuum on my cock. I felt like I was impaling her.
I yanked her head back with each thrust with a grip of her hair. With the other hand I reached underneath her to grab a fistful of tit flesh. I couldn’t help but yank and squeeze harder as I came closer to orgasm.
As much as I wanted it to last forever, I knew it was going to end soon. With a final thrust, I came deep inside her pussy. I could feel the warm cum flooding out of my dick. I stayed in her for minutes afterwards. I could hear her sobbing, which I imagine was partly in relief.
Finally, as I felt my cock start to shrink, I took myself out of her. Cum, a subtle streak of blood dribbled down her thigh. I smiled in great satisfaction, as I confirmed that I took this sexy teen’s virginity.
She lied there, almost motionless. I knew her head must have been in a whirlwind. I didn’t show her much mercy.
I took her clothes out of my locked cabinet, walked to the front of the desk and threw them on the ground.
“Lesson’s over. You passed today, but I’m going to be expecting more tomorrow.” I said sternly
She looked up at me, tears in her eyes and rolling down her cheeks. She was in disbelief. I knew what she was thinking. What more could I possibly expect?
She slowly put her clothes back on in silence. I could tell she had run out of tears for today. She simply looked down.
I reached into my cabinet again, and gave her a small shopping bag. She took the contents out of the bag, with a quizzical look on her face.
One by one, she pulled out a skimpy backless ‘around the neck’ pink halter top, a pair of skinny jeans that were a size too small for her, a white lace thong and a matching strapless white push up bra from Victoria’s Secret.
“On top of being my personal sex toy every day after class, you’re going to be my play thing during the day too.” I sneered “You have terrible taste in clothes dear, so I’m going to be dressing you like the little slut that you are.” I sneered
She continued to look down in shock at the clothes, trying to digest everything that was being thrown at her.
I sneered “Don’t worry. You can keep the clothes. I’ll find ways for you to pay me back after class tomorrow.”