The Cougar of Montgomery Ch. 02

Literotic asexstories – The Cougar of Montgomery Ch. 02 by DJMiles,DJMiles
Chapter One

Tuesday, 4:35PM

My words hung heavy in the air. I leaned against the edge of my desk. My fingers fidgeted with one another in my lap, and I felt the tension in my stomach twisting like a loaded spring.

Why does it matter? This is what I’ve wanted to happen for over a year, and even if it did matter, how would she know?

My light pink v cut sweater exposed a good portion of my cleavage that my arms only mashed together more so. But Justin didn’t concern himself with my ample breasts. No. His eyes traversed my legs like a raft went down white water. His gaze washed over the dark mesh of my fishnets that covered my calves and thick thighs. They paused at where my soft creamy skin disappeared under the dark shadow of my short, red, knife pleated skirt.

It’s your job, it’s your life! He’s your student! He could say something, she could say something!

I stood fully clothed in my own office but felt exposed as he stared between my thighs like I was naked. At that moment, I realized that I was dressed like a high school slut. Like a cheerleader begging to be fucked. Just as I would be dressed 30 years prior when I was a high school and college cheerleader. Even then, I had always had fantasies of a powerful man throwing my tiny figure about before choking me with his hard dick. Other cheerleaders would giggle at my fantasies at slumber parties, calling me Slutty Sarah. So my urges were slowly repressed over the years. And as I entered my thirties, then forties and tried to rekindle those excitements, every man I happened to was too weak or too timid. They drew their lines in the sand well before my needs, which left my cravings unfelt. Over the years, my cravings intensified, though my attempts to satisfy them became- white wash… background noise…

Curbing my thirst for punishment, degradation, and control, I turned to the internet, allowing my eyes to pour over hours of hardcore pornography, and spent countless hours trapped in the imaginary fantasies of erotic literature. Role playing for years, I edged myself to gushing orgasms with various men and women in chat rooms and over the phone. I accepted defeat as I approached my fifties, having only a glimmer of hope that I held on to every time I fingered myself. The hope that I would one day be locked in the room with a wild animal of a man standing in front of me, eyeing me just as my college student Justin was now. But now I stood in silence, fighting a tremble that shook at my knees. I felt the fear of the unknown grasp its way up my throat as Justin began walking for me.

Chapter Two

Monday, 4:52AM

… 36 hours prior…

“Aaaahhh- MMmmmmm!” I groaned as I slobbered around the thick black dildo crammed in my mouth. My left hand fed the dildo into my loud slut mouth as my right pumped a cream colored 8-inch dildo into my slick pussy. The cream-colored dildo had a pair of balls at the base of it which gave me better leverage to hold on to and fuck myself with. I sat on the floor, my knees spread, and my sweaty body was shaking in the darkroom. The blue and white light that flashed from my computer screen bathed my naked curves and thick, bouncy tits as I trembled. “Mmm- ck- ack- Mmmm,” I gagged on my black dildo. I felt my throat seize and saliva poured down my chin as trickles of sweat formed around my brow, neck, and breasts.

I heard the thuds of my 8-incher pounding into my gaping hole. Fucking my juicy pussy into submission. My body was completely naked with the exception of my favorite black laced fishnets that stopped just short on my upper thigh, and a pair of red, 6-inch heels. My feet angled in such a way that every time my hips raised and lowered in motion with my dildo’s penetration, the spikes of my heels dug into my rounded ass cheeks. I pulled the dildo from my mouth and felt a string of spit fall with it to the ground. I bit my lip as I typed quickly on my laptop.

Mmmm yess, sir, fuck your slut! I thought.

I typed to Justin how I just gagged myself as he asked and told him how drenched my dildo was from my slutty twat. He corrected me and said that it was not ‘my’ slutty twat but ‘his’ slutty twat for him to do whatever he wished.

I bit my lower lip and stuffed my dildo deep into my pussy so that I could feel the immense pressure as my lips squeezed on its shaft.

‘I’m sorry, sir,’ I replied. Justin told me to pull on my chain and gave me further instructions. ‘Yes, sir.’

As my left gripped the small linked chain that lay between my thighs, my eyes flickered from the right side of my screen that had Justin’s chat window open, to the left side that had a threesome sex scene on replay. It showed a young, skinny brunette bent over and getting fucked from behind by a fat cock, while her lips were stretched to the limit by another long cock skull fucking her from the front.

Mmmmm god, I want that. Use me like the whore I am!

My right dropped the dildo from my pussy as I pulled the chain with my left. I felt the cool, rough, ribbed metal go taut between my pussy lips. The metal pressed against my pale soft skin between my ass cheeks, on my back, and finally I felt it tighten on my black dog collar fastened around my neck. I pulled on the chain and my pussy quivered as it ground back and forth on my swollen clit. I had been playing for 5 hours straight now, and Justin was yet to allow me to cum.

“Ooohh goddd…” My body shook in protest as the pressure built. “Let me cum.” I whined to no one. “Let me cum. Let-” My breath went short as my dog collar restrained my throat. I pursed my lips as the cool metal still ground roughly on my sensitive clit. My eyes read Justin’s next punishment, and I grasped a medium chip bag clip on the coffee table beside my laptop. My right slowly opened the metal clip as it hovered over my bursting heavy tits. I closed it around my left erect nipple and let it hang.

“Mmmmmmm!!!” I screamed in a hushed hum with my eyes closed as I bounced up and down, trying to forget the pain. My massive tits bounced, making the clip swing, and only caused a sharper pain on my aching pink nipple. I pulled harder on the chain, still able to breathe, but digging the black leather into my skin and the cold metal into my filthy cunt.

I can’t- I can’t- fuck, I can’t hold on much longer. I need- oohhhh… I need to fucking cum so bad.

My right hand shook as I picked up a second clip and slowly closed it on my right nipple.

“Fuckfckfuck!” I groaned with a restrained moan. My fat tits were on fire. My raw pink pussy was on fire. I opened my eyes, biting my lower lip and typed with my right hand slowly. ‘Done, sirr.’

‘Good girl,’ Justin typed. ‘Maybe my whore will still cum yet.

‘Yes, sir, yes,’ I replied. ‘Your whore needs to cum soo badly pleaseplease.’

‘Mmm… With the chain between MY whore’s pussy lips, I want you to clench your thighs together. Tight,’ he typed.

I did so, and as I adjusted, felt my tits sway and my nipples burn with every movement.

‘Grasp the chain behind your neck with your right,’ he demanded, and I followed. My drenched pussy lips poured on the thin chain link as they swallowed it.

‘Now pulllll the chain up with your right hand,’ he commanded.

I gulped and began to pull on the chain.

“Oh, my godyesshitfuck!” I yelled.

I felt the cold metal ribs draaag on my bulging clit, grinding on my inner pussy lips, then finally hooking under my hips and rubbing hard on my asshole between my cheeks. My ass cheeks clenched and loosened repeatedly, which made my upper body bounce and my tits flap.

“Shit shit shit shit,” I screamed.

‘Now pull up on the chain from between your legs,’ he typed. ‘Squeeze those fucking thighs together!’

I ground my fishnets together as I squeezed. My pussy and tits were on fire as I pulled the chain back through. Every rib on the chain hooked on my clit and pulled on it as I ran it higher.

Jesus- I’m gunna cum! I can’t cum he hasn’t let me fuck I can’t- please…

‘Again!’ He demanded.

I pulled it back through my tight slit and started to heave. My mature figure pulsed as my mind lost focus. My eyes went in and out of focus as the sharp pain on my pinched nipples and the fire on my wet cunt mushed with the ecstasy that pumped inside me.

‘FASTER, whore!’ I saw him say through blurry vision. ‘My fucking slutty whore!’

My hands jerked the chain between my thighs faster and faster, up and down. I felt the wetness drip down to my thighs and finally to my calves as I went silent. Furrowing my brow as I hunched over. My hips bucked and my fat tits dangled beneath me like utters on an old cow.

Oh my oh my oh my ooh my goddd I can’t-

My eyelids opened and my retinas focused after realizing my eyes were closed.

‘CUM YOU FUCKING WHORE!!!’ his letters yelled. ‘CUM ON YOUR FUCKING LEASH, LIKE A GOOD SLUT!’

I gasped and squeaked in elation. My hips ground faster against the pull of the chain. I pulled the chain harder and longer. The chain slipped from a sweaty grasp as I rode it harder.

“Oh, fuck!” I screamed, going silent. “Oh jesus!!”

My tits clapped beneath me, and I felt it.

I’M CUMMING I’M CUMMING I’M FUCKING CUMMMMMINNGG!!!

My pussy seized. My lips ate the chain. My body froze and my breath stopped.

A flush of fluids gushed from my tensed twat, and soaked my thighs, my fishnets, and absorbed into the towel below my knees.

“OoooOoohhh shiiiit!” I screamed. My hips vibrated again on the chain. My upper body doubled over as I fell to the side and felt my pussy cum again in hard waves. My sore, aching clit pulsed as I shuddered with every movement.

“Ohh… fuck…” I sighed. My body laid limp for a moment, awakened only by the occasional spasm that permeated from my pussy outward. I raised clumsily to my keyboard and typed to my master.

‘Thank you, sir. That was amazing. You’re amazing…’

‘Mmm :)’ he replied.

I hesitated, my eyes getting lost in a daze at the rough fucking porn on the side of my screen as I consider my next words carefully. It had been four days since I had found out the man that had been taking control of my pussy and commanding my orgasms online for the past year had been a current student. Justin Sales. Not just a student, but a young one, 20… 21 years old at best.

That doesn’t bode well for mutual affection, considering you’re five years shy from fifty, Sarah.

During our brief conversations, I had always known my online master was younger, but I thought 27 or 30. Just as he had always known I was older, but I doubt he’d guess 45 years old. I had a powerful urge to tell my Master my identity. To give him equal standing so that I could finally experience his control first hand. But my words failed me and worse yet, my courage did, too.

What if he thinks I’m too old? What if he thinks I’m ugly? What if he wants nothing to do with me? I’m sure he has younger girls, prettier, with polished skin, and firm tits…

I found myself biting my lip and finally blinked my eyes free of my porn. 5:37am

What!?

5:37am

Fuck, I’m late!

I typed with haste and respect, apologizing to my Master about my fast exit without making any confessions.

‘Yours truly, thelionessofm,’ I replied And I signed out of my personal email I used for play.

I closed my laptop and flipped the light switch on the wall. The light bathed my living room. It revealed my warm colored walls, my busy large rug in the center of the room, and the shelves of books surrounding my flat screen TV. I shrugged on my blue robe and ran to the bathroom, opened the door, and released a stampede of my two Rottweilers, Daisy and Peach. They rushed out from the hallway bathroom where I had them locked away. I twisted the shower handle, grabbed a towel, and began rushing through my morning routine.

I did not have to be in till 7:30am on Mondays for my morning online study session, but with an hour commute into Montgomery from my secluded house in the woods, coupled with an ungodly amount of time it took for me to get dressed and put my makeup on- I was very late. I threw my robe to the bathroom floor as I hung a pair of comfy jeans and a rather conservative black long-sleeved shirt on a hook. I heard Peach bark as I dangled a foot inside the shower.

“Shit,” I said, stomping out of the bathroom. Daisy was nuzzling the old beach towel that was still damp from my explosion, while Peach was chewing on my cream dildo, which I’m sure was still covered in the scent of my pussy.

“No!” I yelled and stomped my naked body at them. “You nasty, bad dogs! No!” Peach dropped my dildo, and I scooped it up and my black one up as well. I balled up my towel with my dildos and tossed them on the floor opposite my toilet.

The good thing about my class load I had this year was that it was simple enough that lesson plans, quizzes, and assignments did not need much planning or preparation. This morning’s algebra class was mostly a makeup class for students who needed the math credit but had no intentions of pursuing more education in the field. It was the same class that Justin Sales was in. He was a junior though and was pursuing a degree in Criminal Justice. He definitely had no need for math, or care, but all weekend my mind was not concerned with his care for math, but if he thought of me even when he wasn’t stroking his hard cock to me.

Mmmm… I bit my lip and fought the urge to push fingers between my swollen pussy lips as I stepped out of the shower and dried my body.

I understood how ridiculous this whole situation was. I understood how close I was to losing my job last Friday when I came in front of class. I understood that even role playing online with a student was grounds enough to have my tenure revoked and to lose my life’s work at 45 years old, I knew that. But something primal inside me stirred every time I thought of the possibility of actually being on my knees in front of Justin. Like an itch in the center of my spine, I yearned for it to be touched.

In a matter of minutes, I threw my clothes on and did a once over on my makeup. With my doors locked, I was on the road, juggling my morning coffee, laptop, purse, file satchel, and cell phone. As I started down the winding dark road that travels through the hilly woods, I thumbed a text to Amber, my assistant.

6:57am

‘Just leaving home. Will be 30 min late.’

As if Amber was waiting by her phone for the chance text, she responded immediately.

‘Ok, I’ll get your Group Chat started on the 5 problem assignments on your desk?’ Amber asked.

‘Yes. Thanks.’ I responded.

Amber was a friend of a friend whom I had hired two years ago. In her late 20s and had just come off a messy divorce, she was in desperate need of a helping hand. She was very shy, a trait that I could relate to having always been more reserved. Her gaining 65 pounds since the divorce did not help Amber’s confidence, either.

It was probably best that I kept my contact with the class to a minimum since both Justin and Jessica were in this class.

My car drove around the curvy road as the foggy haze of dawn warmed the horizon. I felt my panties bunched to the side under my jeans, pulling them tight around my sore, pink pussy lips. I lifted in my seat and picked my panties out from the crevasse of my thick thigh. The shift of panties across my tender lips caused an ache of pain and pleasure that washed through me as I ground my hips into the car seat. My left hand rubbed circles into my jean covered crotch, and I gasped as much out of pain as pleasure from how sensitive my pussy was.

I set my cruise and allowed my fingers to run wild, wiping wide circles into my crotch, groping my plump breast under my shirt, and fingering my nipple under my bra. I was a horny mess, begging to be touched and abused at every waking moment. I couldn’t even drive late to work without bringing myself to orgasm. The sudden proximity to a lifelong fantasy that had never been touched made every movement feel electric.

I couldn’t take it anymore. On the edge of another orgasm while driving 55 mph, I brought my hand to my side and retrieved my cell phone. In a new email box, I composed a short but direct email to Justin’s email.

The email read, ‘Sir, you made me cum most nights over the past year. You made me cum this morning with a chain attached to my collar. If you wish to meet, my office is available on Tuesday (tomorrow) @4:30pm.

Yours truly,

Prof. Sarah Mills

/The Lioness of Montgomery’

I drove for several miles in silence. My thumb is hanging over the ‘send’ button. My stomach was full of excitement, panic, pain, stress, and acidic worry. I typed it knowing with every letter clicked that I would delete it, but I just wanted to get a feel of how it would sound. My best orgasms I had, though, are ones where my fantasies are the closest to actually happening. I know I’m going to delete the email. I enjoy teasing myself by meeting him. That is until I struck a bump and my finger bounced to the screen. When I looked at my phone and realized I had just sent my career ending email by accident.

“Shit!” I yelled. “Oh my god, oh my god, oh my fucking god!” I screamed as I nearly drove off the road. My eyes jittered to my phone and looked hopelessly for an ‘unsend’ button. “Fuck! What have I done… oh my god…” I kept repeating to myself as the rush of panic washed over me. The panic of all the bad things that could happen. I imagined front-page headlines of my chats with one of my students being published. I imagined being called into the dean’s office and being fired. I think of the humiliating phone calls I would receive from friends and family members. I drove for several miles just chewing on my lower lip until I tasted blood and awoke from my state of panic.

Then, as my mind slowed after a minute, a calm resolve sunk on to me. And from that resolve, my imagination began to toy with all the other possibilities that could happen. The fun ones. The anticipation built. I unzipped my jeans, unbuttoning the top button as I pushed my hand inside. As soon as my fingers contacted my pussy, I groaned like slut. “Ooohhhmmm.”

My palm washed the surface of my raw lips. I felt the burning sensation rise as my red, raw lips grew moist. My lips trembled and my breathing was fast. The streets were empty as I slowed and sped without warning. My hands didn’t move quickly enough as they came to my fat tits and pulled my right breast free. Pinching my hard nipple till I felt the need to scream. I shoved my hand back in my pants and forced 2 fingers deep inside my juicy pussy and finger fuck myself faster and faster and fast-

“Oh shiit…” I moaned. “Oh baby- sir. Fuck- oh shit, fuck me, sir, yes. Yes! Oh, shiiit!”

My juices coated my fingers as they pounded my hole harder and deeper. I pictured all the ways Justin was going to use me, fuck me, take me- yes!

My eyes squinted, doing their best not to close as I traversed the road.

“Mmm shit- fuck yes! Yes!!” My hips raised up and lowered and raised higher as I fucked my dirty fucking cunt. “Let me cum, sir, let meee cuuum!”

My fingers pounded my abused hole. Spreading me wide, I fucked myself over the highest ledge I had ever felt. My head swam as the roller coaster dropped and I came on my fingers. My pussy seized. My eyes fought to roll back in my head. My hips bucked, and my hand went white around the steering wheel.

“OoooohhGooddddd!!!” A desperate pant heaved out of me, releasing a powerful orgasm that shocked my heart and dropped my stomach.

“Mmmmmshit…” I mouthed. My mind still ran wild with the possibility of the future.

My body relaxed, and I took a deep breath as I settled back into my seat, then smiled.