mr-caldwell
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Mr. Caldwell

Mr. Caldwell

by Luvsishyp
19 min read
4.45 (20100 views)
older mananaloralcumanal sex
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Senior year of High School was coming to a close and for me it was bittersweet. The promise of an exciting college experience awaited. Of course I would miss my friends and fellow classmates. That said I was looking forward to going to a co-ed college. You see, I went to an all boys high school. One can imagine how mundane that is when you're 18 and a walking talking erection. Little did I know that the mundane clouds hiding sensual possibilities were about to part.

My best friend Dave and I were going to separate Colleges and I think subconsciously we were both trying to hang out as much as possible during our remaining time in school. After last period we met at his car as usual. I noticed a perplexed look on his face as he approached.

"Dude fuckin Caldwell." Dave said.

"Oh shit now what?" I replied.

To say that Mr. Caldwell had a "reputation" at our school is a bit of an understatement. A guidance counselor in his early 50's, he had never married and had no children. To some that would be reason enough to be suspicious. But some of my fellow students had more "hands on" experience with him. It was an open secret that Mr. Caldwell was very touchy feely with the young men on campus. A point that Dave had just experienced first hand.

"So I'm in his office last period and as I'm leaving he comes up behind me and puts his hands on my hips before he opens the door for me. The fucker bumped his crotch right into my ass."

"He tried to play it off like oh excuse me David."

"Oh my God!" I said before laughing uncontrollably. "Dude your his bitch now!"

Dave smacked me in the arm. "Yea real funny asshole. If you tell anyone about this I'll kill you."

Looking back I realize this is how Mr. Caldwell operated. First off he could plausibly deny wrongdoing by claiming his bodily contact was an accident. Mostly though, no student wanted to raise a fuss and risk personal embarrassment. Any administrator aware of the situation just figured Caldwell was harmless or was unwilling to get involved.

Dave and I made plans to hang out that night at his house as his parents were out of town. I was hoping this meant we would be enjoying our favorite pastime.... watching his Dad's porn collection. Back then porn wasnt as readily available and "at your fingertips" as it is today. Us poor perverted souls actually had to rewind and fast forward VHS tapes. Imagine the horror.

So there we were in Dave's room hanging out. I think both of us wanted the other to ask first.

"Sooooo what do you want to do." I asked with a mischievous grin.

"God you're a perv." Dave replied as he pulled the tape out of his dresser drawer.

"Oh yea I'm the perv. You're the one that took it from your Dad's room already."

"Ok we're both pervs." Dave said as we both smiled.

Dave popped the tape in and pressed play. The scene on screen made my heart pound. A blond was riding a big dicked stallion as two other men stood over her spewing shot after shot of thick creamy cum on her face. What stood out to me the most was how much she genuinely seemed to be enjoying herself. Moaning wildly and smiling as they covered her face with their rich loads. This bitch was in ecstasy.

At the conclusion of the scene Dave fast forwarded through some dialogue and landed on a blow job part. The cameraman must of been 6 inches from the guys dick because that 9 incher was definitely the focal point as the girl on her knees sucked furiously.

"Ewww I'll fast forward this part." Dave said, clearly not liking the focus of the scene.

"No!" i said before softening my tone. "Just let it play."

An awkward silence ensued as I realized Dave might suspect that I was enjoying looking at this guys huge dick. Was I?!?! Suddenly I realized I was looking less at the women in the movie and more at the dicks and cum. The women seemed to be the lucky ones as they were getting fed all that hot meat. The sheer depravity of these sluts excited me and simultaneously.... inspired me to be like them?

I was confused but my cock wasnt as it strained in my jeans and pulsed. One thing was for sure. I desperately needed relief. Dave must've had the same Idea because he went to the bathroom just off his bedroom. This meant that I had to use the facilities on the other side of the house.

On the way there I noticed Dave's sister's bedroom door wide open. Just before I passed I caught a glimpse of her hamper and I immediately had a devious thought. Knowing Dave usually took his time in the bathroom I crept into her room hoping to find gold.

To my utter joy and lust I found a pair of Jennifer's worn panties on the very top of the hamper pile. Without hesitation I buried my nose into the crotch section and was rewarded with a wonderful scent of musk and lady stink. My cock was rock hard as I enjoyed my own deviance.

I couldnt take it anymore. My head was in a haze as I replayed the scenes of the big cocks I just watched and savored the scent of Jennifer's pussy. The combination was driving me crazy.

Putting the panties down I raced into the bathroom. Locking the door I pulled out my raging erection and jerked 5 times before blowing an enormous forceful load all over the floor.

I stood there panting looking at myself in the mirror. What came over me? Was I Bi? I couldn't believe I took that risk in Jennifer's bedroom. I thought it wise to quickly clean up my mess and return to Dave's room. Unsurprisingly, we both had sudden appetites and agreed we should order a pizza.

As I sat there in Dave's room contemplating my recent deviant activities a wave of excitement came over me. Though I wondered what this meant about my sexuality I didn't dwell on it. Instead my wonder was focused on the sheer eroticism of my experience. I was perhaps never so turned on before in my life. It was safe to say I was changing.

That Monday school began uneventfully. I daydreamed through my classes in a hyper-sexual headspace. Following classes I had wrestling practice. I arrived at practice late which meant I was getting changed in the locker room all alone. I was down to my underwear when I heard the door open and dress shoes clacking on the floor.

It was Mr. Caldwell. Part of his duties as an administrator were to be available after classes to supervise activities. I definitely felt him "supervising" me at this moment.

He approached me with a smile and asked "Runnin late pal?"

"A little bit sir." I replied.

"Naughty boy" he said as he moved closer putting his hands on my bare shoulders.

He stood about 6 inches taller than me. His big thick hands conveyed strength and overall he was in good shape though a slight belly protruded over his belt line. He wasnt handsome by any means. Nor was he unpleasant to look at.

He rubbed my shoulders and looked right into my eyes. My heart pounded yet I didnt look away. I looked like a deer in the headlights as this much older man touched me inappropriately. I felt small and vulnerable in this position. And I liked it! Suddenly my face formed into a slight smile signalling to him that I was enjoying this intimacy.

My smile emboldened him as he moved his crotch right into mine and trapped me against the locker. I could feel his large hardness up against my growing prick. There was nothing I could do but just submit to his control. I put my hand on his chest further signalling my compliance and he smiled as he realized he hit a jackpot.

I was a nice fresh young piece of meat just there for the taking. I let out a slight moan as his grinding assault continued on my dick. I was rock hard and dripping for him. I was in an erotic haze. This felt so dirty and wrong yet sooooo right.

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I decided to escalate the situation as i spun around. I began to grind my little ass into his big bulge and was rewarded with a low manly groan. He bear hugged me from behind as we continued to grind. i was in lust and wanted to do whatever this old pervert commanded. I felt Mr. Caldwell's warm hands on my bare hips as he pulled me further into him. He now began to pump as if he was fuckin me.

Just then our forbidden contact was disrupted by the sound of a door opening! Mr. Caldwell calmly walked to the opposite end of the locker room and exited through that door. I quickly put on my sweatpants and shirt just before another student walked by me unaware of the depravity that had occurred just moments earlier.

I was still rock hard and in no condition to go to practice. On my way home I marveled at the risk I had just taken. It occurred to me that for the first time in my life another human was aware that I was Bisexual. Needless to say, upon arriving home

I went straight to the bathroom.

I sat on the toilet and started to jack my 7 inch dick thinking about what had just transpired. It was so dirty. So forbidden. My head was in an erotic haze as I thought about how hot this experience was. Bent over for an older man who was simulating his intentions. He wanted to fuck me! It occurred to me what that meant.

He wanted to penetrate my hole. A wave of adrenaline came over me as I realized he wanted to be inside me. My free hand crept towards my smooth puckered hole as if it had a mind of it's own. I started to insert my pointer finger inside when I realized that some lubrication was in order.

Quickly grabbing some lotion I squirted a big gob onto my finger. The cool lotion felt great at the edge of my sensitive hole. I pressed in further with one hand as I jacked with the other. I had never experienced anal penetration before but I realized it would be a big part of my sexuality moving forward.

I fingered my hungry hole rapidly as I thought about Mr. Caldwell. I wanted him to fuck me I realized! With that I inserted another finger. It hurt and I loved it. I started pounding my slutty hole hard, trying to punish it. It was all too much to take as I blew my load all over myself.

As I came back down to Earth reality set in. I had been dry humped by my Guidance Counselor. I was going to see him the next day at school. Another human being was aware that I was hot for cock. So hot for cock. I wanted to be the slut in my favorite porno scenes. This was going to get interesting,

I was nervous the following day as I entered school. Was I going to see Mr. Caldwell? How would he react? How should I act? Still our previous day's grind session was in my thoughts making me hard and horny. It was fun to walk around classes with this sexy secret.

I walked into 4th period English and then....an atom bomb. My teacher Mr. O'Connell informed me I had a Guidance session scheduled and I was to proceed to Mr. Caldwell's office! I tried to appear calm but I think my voice cracked as I said "Ok" and took the hall pass from Mr. O' Connell's hand.

A nervous excitement overcame me. I knew where this was going to go. Our locker room antics were risque and even sexual I suppose but now we were going to officially cross the line. I considered chickening out and going to the nurses office to be released but then I had a realization. I get to be a cockslut. I get to suck cock!

My adrenaline levels were at maximum as I approached the his office door. I knocked lightly and heard Mr Caldwell's deep voice. "Come in." I walked in to find Mr. Caldwell sitting behind his desk with a confident smile.

I sat at the chair in front of his desk staring into his eyes with a lusty smile of my own.

"It's a shame we were interrupted yesterday boy" he said as he stood up. To my utter shock and delight he was naked from the waist down. A beautiful 8 inch hard cock jutted out from underneath his dress shirt. His full and tight big balls showing me the massive load he was holding.

"Lets make sure we have privacy this time," he said walking past me to lock the door.

He returned to me and I was mesmerized by his sexy lewd cock that dangled before me. A smooth thick shaft with a slightly bulbous head framed with bushy salt and pepper pubic hair.

My mouth salivated and my body trembled slightly. He read me like a book.

"Nothing like a first time cock sucker," he said as he put his thick finger in my hungry mouth. My heart pounded as I sucked on his finger not breaking eye-contact. He seemed pleased as I sucked wantonly and whimpered. "On your knees son" he said.

I got down in front of him, his tool inches from my face, and enhaled his manly scent. I licked from the base to his head before pressing the bottom of my tongue into his piss slit and was rewarded with a low manly groan.

Attempting to mimic my favorite porn sluts I took him deep into my throat. Inexperience took me too deep too fast and I gagged on his manhood.

"Haha an eager cocksucker too, eh boy?" he said.

I coughed as my eyes welled up from the choking. I took a big inhalation as I began to jack his big cock looking up at him. "Very eager sir" I said.

"I've got you figured out from the start." he said putting both hands on the back of my head. His cock impaled my mouth as he began to thrust mercilessly. I took his assault as best as I could before grabbing his wrist and backing off for a breath of air.

"Hands behind your back!" He commanded.

"Yes Daddy" I whispered in a submissive voice.

His eyes lit up at my dirty compliance. He began to fuck my face again as I tried to hold on. "Gulg,gulg,gulg" was all that could be heard in the room. There was no doubt about who was in command now. All I could do was kneel there and take it as my nose was now buried in his musky pubes.

Suddenly he pulled out his dripping wet tool. I gasped for a deep breath. "hughhhh"

before smiling at him. His cock looked amazing. Rock hard with my thick saliva dripping off. This whole scene was amazing. I felt like I had been transported into one of those porno scenes I liked so much.

I tried to get back on his dick but he drew it back. "Uh uh" he said as he jacked his manhood. "Not til I tell you." And with that he smacked my face with his heavy cock.

So humiliating,so hot. He was training me! He continued to jack before laying his dick on my face. I understood totally. This was the tease. This was designed to drive me wild.....and it was working.

"Pleeaaaase Sir!"

"Please what?" my Master said. "Tell me what you want."

"Ohhhh please let me suck it! I love your big cock! I need it in my mouth!"

I shook my head back and forth rubbing his big dick all over my face,

"Sir pleeeeaaaassse."

I think he enjoyed my desperation. He rewarded me by filling my mouth with his cock and I accepted it greedily, whimpering and moaning and slobbering on it. He quickly backed me of again and started to unbutton his shirt. "Get those clothes off." he said,

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I immediately stood up and began to strip for him. Looking back it would have been problematic if anyone had knocked on his door. Granted it was a thick door that muffled sound well. But the delay of us getting dressed would of been suspect.

In that moment I didnt care. I wanted to be naked with my new cock stud. I was down to my underwear now. I bent over and pulled them off freeing my hard cock and balls. The cool floor felt good on my bare feet. It was so hot to be naked in such an inappropriate place.

Mr. Caldwell stood there naked before me. A nice broad hairy chest with a bit of a gut below. Not the body of a model but somehow It made the scene all the more hot to me.

I put my arms behind his neck and rubbed my torso against his. I nuzzled my face in his hairy chest while I moaned with delight, his manly body sexy and comforting. His next move was the hottest experience in my then young life.

Mr. Caldwell grabbed his big tool and bent it beneath my balls before drawing it up across my own throbbing cock our heads touching.

"Ahhhh" I murmured as my legs nearly gave out. He continued to massage my cock with his, the warmth and friction driving me wild.

I was out of my mind with lust as his big hands grabbed my ass and pulled me into him. Our cocks smashed together. He squeezed my ass hard before his finger found my crack. Tickling the edge of my hole as we grinded he began inserting into me.

He forced his thick pointer into my hole hard and I shrieked in pain, "Ahhhouwww!"

He mercifully pulled out before putting it on my lips.

"Then get it wet boy", he commanded.

Desperately sucking on his dick finger I tasted my self as I lubed it up.

I finished with a nice gob of drool on its tip.

Returning to my hole, his finger slipped in nicely as I shrieked with delight this time.

He poked in and out sending waves of pleasure over my entire body.

My legs felt weak as he penetrated me so I laid back on his desk spread eagle holding my own ankles back as far as I could.

His grin seemed to say " That's right slut I got you now", as he began finger fucking me rapid fire in this new position.

"Ohhhhh shiiiittttt" I exclaimed as he assaulted my hole.

This went on for a few minutes before he stopped and walked to the opposite side of his desk. Pulling a bottle of hand lotion out of the top drawer he returned to me.

I marveled as he squirted out the lotion and jacked his majestic cock with it making delicious fapping noises. I knew what was coming next as he squirted a large amount on his finger and inserted it into my slut hole.

Quickly adding a second finger he opened me up in preparation for the challenge approaching my virgin hole. He grabbed my ankles and pulled me to the edge of the desk before putting his mushroom head at the edge of my opening.

With my ankles now on his shoulders he slowly pushed in inch by satisfying inch. With a strong push of his hips he drove in the final four inches.

In unison we let out a satisfying "ahhhhhhh".

He held it there savoring the moment as I got used to his filling girth.

Slowly pulling out to the edge of my asshole he then pounded back in. Doing this repeatedly as my words met every thrust. "Fuck. Me. Fuck. Me."

My body was flushed with heat as my cock stood up rock hard.

He pulled out and paused before driving in very slowly. I wrapped my legs around his waist trying to take in more cock as I bucked my hips desperately. This was a Master Cornholer who was strategically controlling me.

"Uhh your teasing meeeee" I said in a sissy voice.

He responded by relentlessly pounding me trying to hurt my boy pussy.

"Ah.Ah.Ah. Yeaaaaaa" I yelled as each thrust sent me into further ecstasy.

This was perfection.

I looked into his eyes as he pounded me. It was evident he knew he was turning me into a butt slut. He had introduced me into the world of anal and in that moment I think I actually loved him for it.

His breathing became heavier now and I knew it was close. My first cum shot!

"Please cum in my mouth Sir! Please!" I begged.

My desperate pleading seemed to put him over the edge as he pulled out.

I quickly jumped to the floor on my knees in front of him.

The anticipation was divine as he pointed his rod at my face. His cock began to pulse as his jacking resulted in a thick rope of cum that landed on my forehead. His manly grunts ringing out, I refused to waste a drop as I gobbled his dick and allowed my mouth to be filled with shot after shot of thick creamy cum.

I swallowed every drop and let out a satisfying "ahhhhh" as I savored the flavor of his sweet salty jism. But know I was desperate to cum and I hopped backed on the desk spread eagle again. I stretched my hole out and looked at Mr. Caldwell in the eyes.

He knew what I wanted. I jacked my throbbing erection as he finger blasted my hole. It was so good but I couldnt hold out any longer as I shot a huge load all over my chest and belly.

I laid there breathing heavy staring at the ceiling trying to take in what had just occurred. Mr. Caldwell stood over me smiling. "I must say", he said. "Out of all my students over the years I think you were the most "enthusiastic". he chuckled

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