The Worst Day of My Life

I felt a little cold. I reached to pull up some covers and found none. Things seemed so hazy. I realized my hand was brushing over a nude body, my nude body. I never sleep nude. The stupor and haze were still not clearing. For some reason, I couldn't get my left arm to move. It was over my head and I felt a sharp pain every time I tugged on it. It was twilight wherever I was, and only half-light. How could I not know where I was? I started to feel more aches and pain. I was shivering slightly. My head would move so I began to look around. I was in a bed. The covers were in a pile below my feet. I was indeed nude. This was not my room. It looked male. Sports posters and swim suit girls on the wall. A general mess wherever I looked. I looked up to see why my arm wouldn't move. My wrist was circled in shiny steel. I was handcuffed to the bed. I began to panic. I forced my self to take deep breaths to calm myself. I needed to clear my foggy mind.

As I lay there it began to come back. Jennifer Darlington, newest english professor at Steadman Academy. I was well liked and respected and I had worked hard for this position. My wild college days were behind me. Ito be honest, I had felt the bite of handcuffs before but by the police. So I was sure I wasn't dreaming. How could I be in a strange room nude and cuffed to a bed? What had I done last night. I struggled to clear my head. A familiar pain centered deep behind my eyes. A telltale cotton dry mouth sensation in my mouth. Drugs. I hadn't touched them in years but I still remember the horrible aftermath of so many miss spent nights.

That was behind me now. I was conservative and upstanding, a model teacher. I didn't flaunt or tease my students. I was tough but fair. How did I come to be here? Slowly it came back. This was the Jenison house. Mr. Jenison had invited me out to tutor his son. Cory was one of those spoiled rotten jocks. All the girls adored him all the teachers made allowances for him. I wasn't stupid. You didn't fail akid witt that name, not at Steadman. I know I would have made sure he passed my course but Cory was a senior. Destined for the Ivy leagues. He didn't have me. He was in Smythe's class. He Wasn't going to get by get by crotchity old Professor Smythe. That was the reason I was Tutoring him.

His dad, Mr. Jenison, was a bigwig alumnus. His family had an entire wing named after it. I had come over to help Cory with his English at the request of the Jenison family. Cory and I had been at it for an hour or two. I was almost getting used to the little snob., here at the estateas I was just trying to make some brownie points with the family and now here I lay in a drug induced stupor, hung over and nude.

I was cuffed to what must be Cory's bed. I wasn't stupid enough to sleep with him so how did I get here. The last thing I remember was taking a break and having a glass of iced tea. Cory had been anxious to be done. His family had gone to the Hampton's for the weekend. The little prick must have drugged me.

Just then the door opened. I recoiled by instinct. It certainly wouldn't do me any good. Cory stood there in nothing but flannel shorts. For eighteen he looked rugged and cute. He had six pack abs and guns that woudln't quit from all the sports he played. Why me? He could have all the girls he wanted. He had millions of dollars and was a blonde, handsome Adonis. He laughed and scratched his chest.

"Good Morning MS. Darlington." He said in a mocking tone.

I tried to say something stern and demanding but it rolled off my thick tongue like a bunch of guttural grunts. He sat in a nearby chair and picked up a remote control. With a flick of his finger a nearby television came to life.

"Don't worry I wont make you watch all of it. I queued up a good part just to give you an idea."

The picture started. It was of me of course and young Cory. I was riding him like a stallion, his cock slick with our combined juices. I was making a chorus of moans. I knew the sound. It was an approaching orgasm. I shut my eyes and Cory clicked off the TV.

He looked at me and said. "You look like a little whore don't you Jennifer. I have three hours of this. I didn't expect you to be such a hot fuck. All I wanted was a little leverage. I am going to pass English and go to Harvard just like ole dad. You are going to guarantee it. I don't care if you have to let shit head Smythe fuck you in the ass I am going to get a good grade in his class."

I had been drugged and humiliated and raped for an English grade. If that was all it would take, I would have been happy to do it for the asking. I was planning on having a little chat with good old Professor Smythe anyway. Not for this little stuck up prick but for his Dad. I had nothing against playing politics with the big boys.

The problem was I knew better. This little prick didn't have the brains to stop there. In a matter of a month or two he would be pimping me to his school buddies. I was caught and had nowhere to go. I could see the look on his face. He was about to fuck me again just to prove he could anytime he wanted. Luckily Pharmaceuticals intervened for me just at the right moment. I opened my mouth and puked right on the floor. Cory jumped up and yelled at me but I was to busy throwing up to hear what he was saying. I had to guess at what he had given me but it must have been Roofies. He must have given me to many and afterward, Alcohol. I had been clean and sober for to many years.

I certainly performed well for his show and didn't remember even a little bit of it. He finally produced a key and I jumped up and dashed for the bathroom. The next hour I was racked in spasms of nausea. Cory left me alone. Finally he threw me a bunch of towels and told me to clean up and get the fuck out. I felt miserable. Not just sick but totally humiliated as well.

I quickly checked the VCR but no luck he had taken the tape with him. I cleaned up the mess as best I could and rinsed out the sour towels. I scrounged up my cloths and got dressed. My little car was still there, tucked behind the big garage. I got in and drove home. I had to stop several times on the way home both for fits of hysteria and waves of vomiting. I got to my little house and went straight to the shower. I scrubbed and washed and washed and scrubbed. My perfect little life was over. I even considered killing myself.

I finally dozed off. I woke to the sound of the phone ringing. It was that little prick Cory. I had almost convinced myself it was all a bad dream. He reminded me he owned me. I cried and begged but somehow in the back of my mind I knew Cory actually enjoyed the pain he caused and he enjoyed hearing me beg. I promised him I would do anything for him.

I got a cup of tea and my Soda Crackers and started to do Cory's homework for him. Just then the phone rang again. It was my Aunt Mildred. I loved to here her voice. Her health was going down hill and she called to tell me she was going into the hospital for a treatment on Monday. I cried again. I got on the phone and made a reservation for a flight right after class on Monday. I then called the head master and told her of the problem with my aunt and she promised to set up a substitute for Tuesday and Wednesday.

My life was coming apart. I grabbed my old phone book and said a prayer. I got ahold of a real old college friend and asked her to do me a huge favor. She said she would be glad to do it and I gave her a shopping list. She chuckled a little and asked me if it was for a Gag Bridal shower. I giggled a little and asked her how she had guessed. I felt better. I knew I could take care of myself but right now my Aunt needed me.

Monday morning I slipped into a conservative suit topped by the distinctive Academy Blazer. I had dug out black high heels and I wore smoke colored hose with a garter belt. Under the Blazer, was a thin crème silk top with no bra. I knew I had to convince Cory I had to fly to the city in the afternoon. Armed with his homework I went to school. I rather enjoyed the attention I got from my young charges but I dreaded seeing Cory. Just before free period I slipped out of my Blazer, put on bright red lipstick and sat at my desk. Right on time Cory walked through the door. I looked at him with sad eyes. I got up and took his hand. I closed my Classroom door and led him to the supply closet. I dropped to my knees and unzipped his school uniform pants. The little asshole was already rock hard.

I let his cock slide down my throat in one easy motion.I looked him in the eye as I sucked his cock. Deep throat had never been my favorite and I was out of practice but I never let Cory know it. I pumped his shaft until I felt the little give-aways that he was going to cum. Just as he started, I pulled him out and lay my head way back and pumped his seed all over my face. By the sound he was making I was doing something right. When he was done I used my best pouty voice and told him I would do anything for him. I told him his homework for the week was done and I would take care of Professor Smythe for him as soon as I could.

Cory was smiling and basking in his perceived power. I then told him I needed to fly to the side of my ailing Aunt. She was going in the hospital. He looked at me with suspicion but I told him he could even take me to the airport and I would make it up to him when I got back. He said he would pick me up after school and drive me. He told me he wanted to show me off so I should wear something sexy for the trip. I handed him his homework and gave him a big kiss. And thanked him for understanding.

As I watched him leave, I smiled. He had no idea the power had just shifted. I washed my face and removed the Cocksucker red lipstick. I finished out my classes and even went as far as sitting on the edge of my desk while lecturing and allowing my skirt to rise up. The pimply faced freshmen boys never realy saw anything I was careful of that but they sure tried. I dashed home and grabbed my suitcase. I put the red lipstick back on and threw my cloths on the bed. I changed to an Academy uniform skirt. It was a standard issue but I had made a girl give it to me before midterm because it was scandalously short. I slipped my heels back on and changed to a white silk shirt that buttoned up the front. I left it unbuttoned and tied it to show my flat tummy. It was down right indecent. I just prayed no one from the school saw me.

The doorbell rang and I stepped out and walked right past poor little Cory. I know his jaw was dropping but I just walked right to his car. I stood and waited and sure enough those Ivy League manners kicked in. Cory opened the door for me and I hopped up into his SUV. I arranged myself in the seat for affect and he ran around and jumped in. As we pulled away from the curve, I untied my shirt and let it fall open. Cory was drooling with lust. As he took me on the short ride to the airport I lifted my skirt and showed him my newly shaved pussy. I began to play with myself and Cory almost swerved off the road. shirt as I went. Cory hustled after carrying my bag. I went through the Security checkpoint and told Cory to pick me up Wednesday night. He just stared open mouthed and let me walk away.

I went straight to the ladies room and took another outfit out of my handbag. I was getting plenty of looks from the airport security staff. I am sure they thought I was an out of town high dollar hooker. I slipped on a modest sundress and boarded my plain. The trip was short, only thirty minutes. My old girlfriend picked me up at the airport. She handed me the bag of gag gifts I had asked for and took me to my Aunt's House. I stopped and talked to Mrs. Senton, the next-door neighbor, at the front porch as I got there She wished me well and gave me a card for my Aunt. I slipped in and put my suitcase in my room. I quickly repacked a dark backpack with things I would need and took off my hose and Garter belt. I changed to tennis shoes as well. I slipped my Aunt's Little Toyota out of its spot and drove to the hospital. As I got there I went straight up to her room. The surgical nurse was just administering the anesthesia. I talked to her and told her, I would wait for her.

All went well. The operation was minor and she was wheeled into recovery. By know it was late. I held her hand for a minute and then on the shift change I slipped quietly out to the car. I carefully rolled it out of its spot and down the street. At the bottom of the Hill I started it and wheeled it onto the Interstate.

An hour and a half later I was sitting quietly on a fence top at the edge of the Jenison Estate. I had changed into all black and I was carrying my dark backpack. I slipped all the way into Cory's poolside room with out being noticed. The room was empty. I slipped into the bathroom and waited. Around one in the morning, Cory staggered in. He had been out drinking with his buddies. From the shadows I watched him strip out of his cloths. As he stepped into the bathroom I sprung. I landed on his back and the cloth soaked in Chloroformsettled over his nose and mouth. He swayed and tried to get me off. The drug took affect and he went down like a rock.

He was heavy and awkward but I was determined. 20 minutes and three doses of Chloroform later Cory awoke on his own bed. Of course he was nude, as I had been. His left hand was tied securely to his left ankle. His face was buried in his pillow. His ankles were tied to a convenient mop handle as far apart as they would go and his cute tight little ass was sticking invitingly in the air. His right hand was in a handcuff the other cuff was around the base of his balls and cock.

I too was nude. Well almost nude. I wore a little surprise for poor little Cory. One of the gag gifts I had my friend buy was a nice big Black lifelike penis. The kit had a harness with it and I was now sporting a 10-inch pliable rubber hardon.

As Cory started to come around I slipped behind him. I ever so carefully laid my hand over his and wrapped it gently around his hardening dick. I gently and sensuously licked his balls and helped him stroke his big cock. I trailed my tongue carefully over his asshole. The cock he was now pumping was fully engorged with blood. I slipped my hand off of his and allowed him to continue to jerk off. I took a large dollop of Vaseline from the convenient jar, and worked it around his tiny puckered hole. My fingers were now slipping in and out with ease. I slipped my free hand around the base of his cock and quickly cinched down the handcuff there as tight as it would go. He tried to scream then but must have realized the used boxers that were stuffed in his mouth muffled him. I knelt behind him and slipped that big rubber cock up his cherry ass. He again tried to wiggle free. He was tied way to tight to allow that. I reached over him and grabbed his wavy blonde hair and snatched his head back. I let the tie that was holding the boxers in his mouth loose and he spit and sputtered till he could talk.

He said to me in a menacing voice." You fucking whore when you let me go the tape is going straight to the head master. You are done here you bitch."

I just laughed at him. "Cory, my sweet little punk ass sweetheart." I crooned to him. " If that tape gets out I will tell them how much I loved you and how I couldn't resist you. They will quietly cover it up. I will move to another town and got anew job. It will be all so hush hush." The Jenison Family and SteadmanAcademy just couldn't have a scandal like that.Think of the headlines! Read all about the star athlete and a new teacher in a torrid love affair. How could they? But some early morning a month after, or a year after a maid will find you like this. With magazines like the one in front of you all over the place!"

Cory looked up for the first time and saw the gay BDSM porn magazine that was lying open on his bed. " I will have a perfect alibi. Hell you put me on the plane yourself. You will be strangled like this."

Just then I slipped the noose tight around his neck. He again began to struggle but I held his head tight and aimed it straight at the other rubber cock I had brought. It was attached to his head board by a suction cup. With the pressure of the noose and my firm hold on his hair his mouth fell open and I slammed him with my hips till the cock was wedged deep in his throat. I took a few minutes and just enjoyed fucking him. The look of him struggling around that big cock in his mouth and the big black one coated with lube sliding in and out of his ass sent waves of pleasure through my body. The base of the strap-on was putting delicious pressure on my clit. I rocked through an intense orgasm and let up on Cory just in time for him to regain his breath.

" You see Cory. We could have had fun together if you knew how to be a real man. I haven't always been the sweet innocent english teacher! But no! You had to pull that rape crap on me. Cory I am not even going to ask for the tape back from you. But just as sure as you can feel this cock up your ass, if you ever let anyone see it they will find you dead in a puddle of your own cum. They will call it a gay auto-erotic asphyxiation accident. You will be found with a dildo stuffed up your ass and a pile of gay porn magazines on the bed. Your cute little hand still wrapped around your greasy cock. The key to your cuffs just a little to far away! Poor little fag boy Cory."

He just whimpered. I basked in the feeling of power just then. The bed was moving ever so slightly and I realized the little shit was still jerking off. I laughed out loud and told him to suck the cock in front of him. He closed his eyes and gave the rubber dick deep throat as good as a twenty dollar crack whore. I rode his slick ass till I had another tremendous orgasm and then I put the key to his cuffs in his hand and slipped out his door. The trip back to the hospital was quick. I met my aunt as she came awake in recovery. No one even knew I had ever left. I slept soundly that night with a smile on my face. I was looking forward to having my little fag boy pick me up from the airport on Wednesday. I wondered if Cory had any idea that Professer Smythe had no interest in me at all. I was a girl. Actually the old man would much rather fuck cute little Cory in the ass than me. I got breakfast and wondered what Cory would be willing to do for that A in Senior English.