Cassie Ch. 06: An Upskirt Battle

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Authors’ note: A warm virtual hug and a big thank you for all of your kind ratings and helpful comments. We’ve learned a lot from this gracious community and we hope to contribute even more down the road. And as usual, all persons who write for, and participate in these stories are at least 18 years of age.

I honestly can’t believe I’m adding to this big, messy situation, but here we go! My name is Tessa and I’m Will’s little sister. I have long brown hair and green eyes, just like my mom. I’m a little taller, but not as curvy as her, and that’s okay! Maybe over time I’ll fill out some more? I dunno, but I’m happy with my body and I’m waiting for that special guy who feels the same way. 🙂

Anyway, I felt like I needed to share my side of the story because I’m the most TRUTHFUL person in my family! I’ve read the previous stories and I can tell you right now, while they are fun to read, there has been some serious exaggeration going on! Y’all probably guessed? Some of you even commented at the end of their chapters and yeah, you are totally right! Anyway, y’all can thank me later because I’m here to set the record straight. 🙂

For example, you probably remember that “milky” sex scene between my Aunt Cassie and Will in the bathroom? I think that was chapter 2? Well, I saw the whole thing happen. Yup, I’m a nerdy, peeping tom and I put a hidden camera in that bathroom (btw, remind me to tell you about some of the other crazy stuff I’ve seen happen in there!). Anyway, luckily I recorded Will and my aunt and watched the footage later that night. And yeah, I’m sorry to inform you that, while their sex was super hot, it didn’t happen exactly how my aunt said it did. Want to know what actually went down?

Well, after Will joined Cassie in the bathroom, they didn’t waste any time. She sat up on the counter, lifted her shirt, and Will quietly sucked on her nipples. But did I see any squirting milk? NOPE! I couldn’t see him swallowing anything either, but I guess I’ll never know! Anyway, Cassie lifted her blue skirt and pulled her panties to the side. Then Will pulled down his shorts and they fucked in silence. Even though he came pretty fast, it was really hot to watch alone in my room. I put the video on repeat under the covers and masturbated like crazy, at least until I fell asleep.

So there ya go, like I said earlier, all of their original stories aren’t 100% true. But, don’t you think they were fun to read?! I think so too! Anyway, now back to my story. Like I said earlier, I’m part of this really messed up family, and I’m also the introverted, nerdy one. Hey, I embrace my identity, okay? I wear black rim glasses and I love math and computers. The only problem is that I’m also cute and curvy. In fact, I must be decently hot because even though I wear regular (not necessarily sexy) clothes when I’m at school, all of those damn guys (and girls too) keep undressing me with their eyes. It’s like they have x-ray vision or something! Even my history teacher, Mr. Ashton keeps checking me out. High school is supposed to be a time of learning, but the only thing that these horny bastards seem to think about is sex, and I’m certainly no exception. I’m also a sex-hungry teenager, but I also love to study and learn, so it makes it hard to do both, ya know?

Okay, so why am I writing down what happened to me? Well, because I want to talk about math of course! Naw j/k haha! Seriously though? It’s because I’ve had some stupid-crazy experiences lately and I need a mental outlet. This stuff is just too intense to hold inside. My thoughts and feelings are like an orgasmic volcano, waiting to erupt.

Alright, so if you can’t already tell, my sexuality has been really suppressed since I started puberty. I’ve always felt like I needed to be a good little girl, like if I just focus on my grades, that my female needs wouldn’t become a nuisance. In other words, I’ve chosen other priorities that have kept my growing sexual fire under control, that is, until just a couple weeks ago.

It all started when I was studying in the school library early one morning. I was sitting in my usual spot, working on my laptop, when I saw Mr. Ashton walk in. We sometimes call him “Mr. A” for short. He’s a good looking guy, tall, tan, muscular, but also pretty smart. He was wearing some slim fit dress pants and a button down shirt with a tie. I tried not to stare, but damn, he looked so fine! Before he could notice me from a distance, I pushed my glasses back up my nose, fixed my posture and adjusted my bra. My shapely girls barely fit in a c-cup, and so I can feel pretty self conscious sometimes, especially if I wear a revealing shirt. It was already warm outside when I left my house, so I decided to wear a light cream polo and a short purple skirt. My red lips accentuated my cute outfit and my outfit accentuated my young curvy body.

Anyway, back to my story. I was sitting at a table at the far end of the library and I don’t think Mr. Ashton saw me right away. He sat down at a similar table that was in my direct line of Girne Escort sight, and started to grade a large stack of papers. He yawned and stretched, and then we briefly caught eyes from across the room. I had an innocent crush so I felt sorta funny seeing him here. I awkwardly dropped my attention back to my laptop but I could feel him smiling at me. When I didn’t look up he boldly called out in a breathy voice, clearly defying universal library rules.

“Hey Tessa, good morning!”

A smile crept onto my face and I waved shyly, again adjusting my glasses.

“Sorry! I forgot we have to be quiet in the library!” He bantered in such a gregarious way, that he put me at ease and I felt my shoulders relax a little. Another student in a different section looked up briefly and scowled, but then quickly went back to work. Mr. Ashton gave me a cute thumbs up, and I remembered that he is a really nice guy, and genuinely cares about his students. So, even though I thought he was gorgeous and only a couple other people were in the library with us, I felt comfortable and knew I could be myself around him.

After his funny little joke about being quiet, I returned to studying and shifted to get comfortable. But, as soon as my butt moved in the chair, I felt my neck and face flush with anxiety. I buried my head, trying to hide my panic, because I suddenly realized that if I wasn’t careful, he would be able to easily see up my purple skirt from his position. How did I know? Well, I could clearly see his feet, legs, and the outline of his male parts, so I was pretty sure he could see under my table as well.

I complained to myself, “Couldn’t he have sat somewhere else? Good grief! If I don’t keep my legs crossed the whole time, he might get an eyeful of my light pink panties!” And, just so ya know, girls learn from a very young age how to cross their legs in discreet ways. That’s so they can guard themselves from any pervy roaming eyes. So, because I was trained from an early age to protect myself, I instinctively felt anxious that a teacher might try to look up my skirt. I glanced down nervously and adjusted my clothing, and made sure that my legs were securely crossed.

I again returned to my laptop, trying desperately to focus, but the stress of creating an unplanned voyeur situation for my teacher kept rising. Little beads of sweat started to form on my forehead and chest, and I squirmed in my seat, wrestling with increasingly naughty thoughts. And, as I continued to entertain these naughty thoughts, my anxiety slowly began to morph into this white-hot burning question:

“So…what if he saw me? What then?”

My mind raced and I asked myself further, “What if I were to give Mr. Ashton a little show this morning? What’s the worst that could happen? So what if we have a little fun together? But would he get in trouble? Would I get in trouble? What if I spread my legs and then later claimed it was an accident?”

As I thought about these questions, the rational side of my brain said, “He’s a really nice teacher, he’s married, and I don’t want him to have any issues with the school or his wife. He might also not like what he sees? What if he reports me to the administration for lewdness?!”

But then the horny side of my brain protested and I remembered all of his subtle double-takes in class, especially when I was wearing something cute. My dearest friends/readers, it was at this critical juncture that I lost all self-control! I know, I know, I’m just a terrible, naughty, incorrigible teenage girl, and I need y’all to spank me for it! 😉

So anyway, when it came to Mr. Ashton, I couldn’t control my brilliant, yet dirty little mind as it ran for the hills and envisioned my sexy teacher getting turned on by an accidental glimpse under my skirt! This pornographic thought sent a sudden rush of blood into my tight virgin mound, and with zero self-control, my legs opened slowly like a Venus flytrap under the table. I looked down and blushed again as I realized what my teenage hormones were forcing me to do. My vagina took over at that point, and I suddenly realized how desperately I wanted a hot teacher like Mr. Ashton to fondle my pussy with his eyes.

I spread my legs wider and tried to pretend that I was studying. But, I also needed to keep close tabs on my teacher, so about every 30 seconds or so, I would glance over my black rim glasses with pouty lips, hoping to see him check me out. But no! This was so dumb! His eyes were glued to his papers, and so I eventually stretched and yawned sort of loud. Still nothing? Come on man! I even tried a silly fake cough, but he was apparently very good at focusing, even when a hot little student like me was giving him the sexiest view of his life!

I desperately looked around on my table to see if there was something I could do to draw his attention, and that’s when I saw my phone. An alarm! Yes! I could set a fake alarm, and that would surely get him to look! I searched and found the loudest, most obnoxious alarm Magosa Escort sound possible, and set it for 1 minute into the future. I smirked at my stroke of genius. HA! I could feel my heart pounding with anticipation in my perky-breasted chest and felt my pussy juices flowing even faster. Then, just as I put my phone down, I swear I saw Mr. Ashton move in my peripheral vision! I looked up and watched his face quickly drop, as though I had caught him checking me out! AHA! I examined him further and he definitely seemed a little uncomfortable as he shifted in his seat and loosened his tie with a big gulp.

My questions wouldn’t stop. Did he already check me out but I didn’t notice? Did he see my light pink panties from across the room? What is he thinking right now?!

My legs were still spread nice and wide under the table, giving him every opportunity, but I still couldn’t tell for sure if he had seen anything. I played with my phone with my right hand, and then slid my left hand under my skirt to gently rub the soft skin of my inner thighs. I wanted to send a clear message when the alarm finally went off.

I looked up again at Mr. Ashton and that’s when his sexy image will be forever burned into my brain. I could DEFINITELY see a long, growing coil under his pants. His left hand (with his wedding ring still on) slowly moved down and touched his sensitive snake. He was still looking down at his papers, but that’s when I fully understood. I realized in that moment that he HAD seen me, and that he had probably looked MULTIPLE times! In fact, he had been timing his glances over the past few minutes, just so that I wouldn’t notice. That sneaky devil! Yes! He had totally been checking me out and I was clueless! Hey, I admit I’m a nerd. I never said I’m solid in the street smarts department! 🙂

The alarm finally went off and I reached to silence my phone. I looked at him and he lifted his hand to his mouth and with an impish grin, put his index finger on his lips, “SHHHHH!” I almost came right there in the library because of how excited I was. My pussy was swollen and ached for more attention, so I dramatically pulled up my skirt to give him a much better view. I looked around just to make sure no other students (or heaven forbid, teachers) could see what I was about to do.

With our eyes locked onto each other, I leaned back in my seat and spread my legs all the way. My whole body was on fire and my mind was total mush. I teased him by peering over my glasses and making pouty, “ooh” shaped lips. I even drew a little circle around my areola with one hand, and with the other I started rubbing my raised clit through my wet panties.

At this point the library was still pretty quiet, but I wondered if he was feeling nervous about being caught. Mr. Ashton cautiously paused and looked around, so I drew him back by pulling my panties to the side to let him see my steamy teenage vagina. He held his breath and rubbed his bulge a little faster, and I cheered him on by using two fingers to open my tight pink lips. My crotch was so hot now that I swear I saw some steam rising from under the table!

Mr. Ashton looked like he was going to cum in his pants soon, but I needed more. I grabbed my big black pen on the table and pushed it slowly inside my glistening cunt. I bit my upper lip and grinned like a nasty little temptress. I wanted my teacher to stand up, walk over and fuck me right there in public, but I knew that we’d likely need a raincheck on that.

Then, I gritted my teeth and inhaled deeply, and dramatically pushed the pen all the way in so it disappeared. Mr. Ashton’s jaw dropped and I shrugged my shoulders as though I had just performed an amazing magic trick. I raised my eyebrows as if to ask, “where do you think it went?” He laughed at my cute theatrics and pressed down even harder against his throbbing cock.

So now, with my pen firmly inside my pussy, I clasped the table with both hands and began to flex my vaginal muscles. My pussy magic continued to amaze my teacher as he watched the pen’s head reappear. I bore my eyes into Mr. Ashton’s desperate face, making him want me more than anything else in his boring life. I started thrusting my hips a little under the table, as though a black cock was fucking me, and even let out little cooing noises that I hoped he could hear. I squeezed hard and finally managed to push the pen all the way out!

Then, as it dropped loudly on the floor I watched in awe as Mr. Ashton performed a magic trick of his own! A big wet spot appeared on his pants! Out of nowhere! I almost shouted “Wallah!” but resisted. I gleefully watched him shudder in ecstasy and I cheered in my mind, “I got my teacher to cum! YES! In the library!” I honestly couldn’t believe it. He would need to teach class soon, and his pants were soaked! Poor guy haha!

After waking up from his sex daze and realizing what had just happened, he stood up quickly, collected his paperwork, and nervously shuffled out the door. If it wasn’t for my Lefkoşa Escort own need to orgasm, I would have joyfully laughed the whole thing off. Instead, I looked around to make sure I was alone and I found a secluded place. I got comfortable in one of those soft fabric reading chairs behind a bookshelf and spread my long, sexy legs. I pulled my wet, gooey panties down a little bit and then shifted them as far to the side as possible. I needed full access, and I needed it badly. Inappropriate thoughts of Mr. Ashton flooded my mind and it didn’t take much. With all four fingers I rapidly rubbed my engorged clit as fast as possible. My whole arm was shaking and sounds of wet flesh and my heavy breathing filled the air.

“OOH, OOH, OOH”, faster and faster I went.

Until…YES! I peered down at my private parts as I started to cum and I could tell it was gonna be a good one. I bucked wildly into the air, closed my legs, and my abs went stiff. I tried to hold my breath and even put one hand over my mouth to avoid screaming. I pushed down on my vibrating pussy as hard as possible, and as I rode it out, I used my other hand to clench one of my tits under my cream-colored polo. I glanced around to see if anyone was close by and then moaned with satisfaction, “Well, that was incredible.” As my tummy began to relax, I watched my hips slowly lower like an airplane, and noticed a little stream of my warm juices drop onto the fabric.

But then, guess what? A new video of me bouncing on Mr. Ashton appeared in my head and I felt the rising urge for round two! I threw all caution to the wind, stood up, and snarled fiercely in my secret corner of the library, “I’mma fuck ur brains out, Mr. A!” At that point I didn’t care if someone saw or heard me. I was COMPLETELY out of control.

I turned around to face the chair and performed a little striptease, swaying my hips while bending down, as though Mr. Ashton was sitting there. I reached under my short purple skirt and slowly lowered my moist pink panties, finally laying them to rest around my ankles. Like an athlete, I squatted determinedly, and pressed my cunt down onto the soft fabric corner. I needed as much pressure as possible, and luckily the material was rough and stiff enough to quickly send me into my second orgasmic whirlwind. It felt AMAZING.

“GAWWWWD.” I cried out carelessly as I started to convulse.

I started to fuck that GD chair like a sex-depraved lunatic and felt my entire body quiver as I vice-gripped the seat-back with both hands. Then, in mid-orgasm, I shifted my body and sat down full-force and rode with reckless abandon, just like a cowgirl that was finishing with a big dubya at the rodeo. I felt shockwave after shockwave of pure ecstasy pouring down through my legs, and my knees finally buckled. When my orgasm finally subsided, I gathered myself and surveyed the damage. There were two dark areas that would likely leave a stain on the chair. “Whoops,” I whispered quietly, trying to be a good student and obey the rules of the library, “3 wet spots achieved this morning. Not too bad, Tess. I guess you’ve earned an A for today?!” I smirked as I walked confidently toward the exit and even winked at some poor kid who may have overheard a little too much? 🙂

I made my way to the restroom after that and cleaned up a little. My sex parts were relaxed, but super messy and even a little bruised lol. I had to wring out my panties in the bathroom sink, but hey, that isn’t the weirdest thing that I’ve seen girls (and guys) do in our school bathroom!

My morning classes were boring as I eagerly anticipated to see Mr. Ashton in history after lunch. As I walked into his class, my excitement was replaced with disappointment, but then humor, as the sub announced that our “teacher wasn’t feeling well and that our papers wouldn’t be graded until tomorrow.” HA! I looked down at my fruitful loins and jeered, “You dirty little whore. You made the teacher call in sick!” I snickered and felt so much power as I looked down at my gorgeous sex-machine of a body. I caressed my firm lower tummy at my desk and thought, “This body is untested, but it was definitely built for sex. Yup, it REALLY needs sex, and it needs as much as I can get.”

During history class I watched for a moment when the substitute stepped away from Mr. Ashton’s desk, and I snuck a little note into his top drawer. What was on that paper you might ask? Hmmm, well, let’s just say it mentioned an opportunity for more. 🙂

A few days passed and I started to feel less confident about our secret encounter in the library. When I returned to Mr. Ashton’s class, he didn’t acknowledge our experience or my note, not even in the slightest way! I began to wonder if he regretted our amazing moment together. Did he tell his wife and feel guilty? Did he get into trouble? All of these sad thoughts threw me back into my sexless shell, and it felt terrible. I desperately wanted to know what he thought about me.

A full week went by and I began to put the whole thing behind me. Yeah, it was an exhilarating moment, but I had relinquished any hope of an actual fuck. My demeanor had turned from confident, to hopeful, to awkward, to self-loathing pity, in that order. It was awful! If only I could read minds! Where was my superhero power when I needed it most?! (nerd alert, I know!)

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