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Jessie Goes Deeper

Category: Fetish
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It wasn’t until Wednesday that I felt like I was no longer walking bowl legged. On the past Saturday I was a target for over one hundred men as the ejaculated on my head. My entire head had been wrapped in one of those cones a vet uses to keep a dog from biting itself. Towards the end of the evening I was made to drink almost a gallon of cold wet slimy cum.

After that Professor Washington, owner of one of the biggest cocks I have seen fucked my pussy and ass raw. And Wednesday was the first day that I felt normal again.

I was in Professor Washington’s class on Thursday and at the end of class he handed me a letter similar to the one he gave me the week before. I should explain that I was caught plagiarizing on my term paper and in order to avoid being kicked out of college, I had agreed to do whatever the Professor asked. Last Saturday was the first day and because I had failed the cum demonstration I was required do it again in a month. Until then I was to report to his house every Saturday at 10AM for training.

In this letter were instructions and money. I had to go to an adult shop in town and be fitted for a predetermined outfit for Saturday. Last week it was red vinyl bustier and thong. I would not know until I got there what this weeks outfit would be. Whatever it was I would be required to wear it and nothing else to the professor’s house. Last week he kept me on the porch for a few minutes in the bustier. Who knows how many neighbors or people driving by spotted me.

I should mention that both my Mom and Aunt Suzy are also under the control of the Professor. They were both caught in compromising situations and the Professor agreed to keep their secrets as long as they continued to be of service to him. In fact last Saturday, my Mom licked both my pussy and ass clean so that the Professor would be happy with them when he fucked me. Although I do not know what Saturday will bring I do know that the Professor wants a girl who can take his huge cock into her throat. I have been throat fucked and like it, my only concern is the size of his cock.

I arrived at the adult store later that afternoon and was asked to try on my outfit for the right fit. This week it was another bustier, but this one had no bra cups and there would be no panties. Instead there were garter straps affixed to the bustier and I was given a pair of sheer black stockings. Last but not least I was provided with a pair of black 6-inch high heels. Interesting outfit but no hint to what was in store for me.

Once again I dressed in the outfit in my room and because Mom knew where I would be and Dad was gone I went straight to my car in the outfit. If someone saw my tits and pussy so be it. I arrived at the Professor’s house on time and was immediately met at the door. Before I was allowed into the house a black bag was placed over my head and then I was, led by the hand into the house. I was left alone standing there blinded by the bag for what seemed like and hour. I could hear voices whispering around me but could not pinpoint exactly where everyone was or how many there were. The thought of being viewed like this in this outfit and hidden behind the bag was exhilarating and I could feel my nipples get firm and my pussy start to leak.

It was then the familiar voice of my Aunt Suzy that came to get me. She took my hand and led me down a few flights of stairs and through at least one doorway before removing the bag from my head. As I looked around all I saw were instruments for bondage. I guess I must have looked a bit frightened because Aunt Suzy said to me.

“Its’ will be OK Jessie. Both your Mother and I have been through this day and although we were scared that day we both would love to live it again. There is nothing that will ever compare to your first serious bondage scene. So relax, do what you are told and trust me, you will want more.”

Although I was not as frightened as she thought I was, her words did comfort me. We were, joined in the dungeon, by my Mom. Both Mom and Aunt Suzy were wearing very sheer white dresses and nothing else, no shoes, no panties no make up. They told me it was there job to prepare me for the professor.

And so the day began. First they asked me to bend at the waist over a padded bar and hold another bar that was affixed to the opposite wall. As soon as my hands grabbed the bar they slapped a set of wrist cuffs on me to prevent my letting go. Similar cuffs went around each ankle to prevent my feet from leaving the ground. My hair hung down in front of me and my tits were pointed to the ground. Then both Mom and Aunt Suzy began to place a soft cotton rope around my breasts at the point where the breast is attached to the chest.

They pulled the rope taught and continued to place more and more rope, round and round my tits working towards my nipples, pulling it taut as they went. The effect was to force the bulk of my tits into a slender cone and push the nipple out further. As they continued down the sides of my tits I could feel the pressure building and soon my nipples felt like they were being pounded from the inside. It went from a heavy pressure to pure pain as they finished and tied the ropes off. The longer these ropes were in place the more painful it became, I was moaning a shaking my head no and was ready to beg to have the ropes removed, when Mom said.

” I know it hurts Jessie, both of us have been there, just give it a few minutes. It will be tolerable soon, just be patient.”

If you could not trust your Mom whom could you trust? I tried to be patient and sure enough it was tolerable. Not having the pain to think about allowed my mind to realize that my pussy was gushing. Evidently my body understood before I did how good the pain would feel.

Mom and Aunt Suzy the proceeded to lie out equipment that I assumed the Professor intended to use on me that day. All of it was typical, a paddle, a whip, a blindfold all the regular bondage stuff. Then they rolled out a table with at least ten butt plugs. What was interesting was each plug was bigger then the one next to it. The last one in line was huge, at least 5-6 inches across. It would rip any asshole apart, feeling a bit of fear I asked Mom what all the butt plugs were for. She said.

“Remember I told you that the Professor wants a girl to take his cock into his throat?”

“Yes, I remember that, Mom.”

“Well the Professor’s cock is about 12 to 13 inches long. He will give you about a half hour to do your best to accommodate his cock in your throat and your Aunt Suzy and I are to measure how much cock you could not take. The inches you do not get in will correspond to a different plug. So if you get all but 5 inches you get plug number five which is this one here!”

She picked up one that was about two thirds of the way from the smallest. I realized that I needed to have less then 5 inches remaining or my ass was going to be stretched so wide you could put three fat cock’s in there at once.

Soon the Professor strode in. His body still disgusted me but his cock made me drool. Just seeing it again had both my pussy and ass reacting. I knew enough to be quiet and wait to be told what to do, but I knew it was ok to stare at that magnificent cock and I did. I was so wrapped up in staring that it came as a surprise to me when the paddle smacked my ass and I yelped. I knew that would not be tolerated so I concentrated on keeping my mouth shut and taking the smacks. The next 15 smacks hurt like hell before I noticed how I was squirming and trying to get something to touch my hot pussy. The professor finished at 20 and although I could not see it, I knew my ass was bright red, I could feel heat emanating from it myself.

The professor stood in front of me and Aunt Suzy was holding his cock upright and pointing it at my mouth. I opened as wide as I could and the professor leaned toward me sliding that giant salami into my mouth. Shit he was large but I forced my mouth further open and the Professor was able to push far enough in to make me gag. As I wretched around his fat cock he pulled it form my mouth and I was able to spit out the saliva I had generated. I spit it on his cock because all my previous cock’s liked that. Evidently so did the Professor. He leaned into my Aunt’s ear and whispered an order. My Aunt called my Mother over to help and they retrieved something from a closet.

This time the Professor held his own cock and pushed it past my lips, as he was nearing the back of my throat a felt a stab of fire in my nipples and tried to open my mouth to scream. The Professor noticed this and took that opportunity to ram his thick cock into my throat. Sensing his success he started to pump that monster in and out of my throat. I was able to tolerate the pain in my throat because the burning of my nipples kept me from reacting to this huge piece of meat ravaging my throat.

My whole body was reacting, my nipples hurt like hell, my throat was jammed with cock, my pussy was wetter then ever and I was cuming. Evidently so was the Professor as I felt his cock jump in my throat and his cum shoot straight down my throat. As he pulled out and backed away I was able to look down and saw the cause of my nipple pain. On top of the pressure from the ropes squeezing my tits into a cone, my Mom and Aunt had placed clamps on my nipples. Before I could say anything my Mom said.

“Good work Jessie, you managed to take all but 5 and a half inches of the Professors cock. We of course will round that to 6 and she pulled a butt plug form the cart.”

I was afraid of trying to take number 5 and now I get the next larger size. Fuck there is no way that thing gets in my asshole. But they were going to try. After liberally coating the plug with lubrication, my Aunt coated her hand with the same and slid a few fingers into my ass. I have had some large cocks in there so her fingers were pretty normal. However when she slid all five and began to fist my asshole I was in seventh heaven. She did that for a few minutes as I reveled in the bliss of an orgasm when I felt an enormous pressure replace her fist at my back door. Oh shit they were working the plug in my ass.

It took a while and a lot of pain ad discomfort but I heard that sucker pop in I knew all of it was inside me. I had that full feeling you get when you have a large cock in your ass and I could have gotten used to it if they had just left it there. That was not to be, as both my Aunt and Mom would twist it, pull it out and shove it in again and again. Initially I continued to feel some pain but after the first few removals and reinsertions I was really enjoying it. I had already had a few mini orgasms from their play and was building to a monster when they stopped and walked away. They left me there unfulfilled for an hour or more. I was still bent over, my tits tied up with rope, clamps still biting into my nipples and a fairly huge plug in my ass. I was hot horny and getting mad, I wanted to cum damn it.

Then the Professor walked in and stood behind me. I felt more then saw him as he edged closer. His cock was free I could see it hanging as he walked past me. The next thing I felt was the head of his cock plowing my pussy open. Nothing slow and easy this time, he slammed into me putting a real strain on my ankles that were cuffed to the floor beneath me. But he continued to fuck me like a cheap street whore. He reached around and ripped the clamps for my nipples and I screamed like someone had shot me. The pain was intense but so was the orgasm that followed. When he began to slap my roped tits, each jolt sent a spark to my overheated pussy causing me to orgasm again or to extend the orgasm I was in the middle of. Who knew, all I knew was with every slap on my tits the pain ran to my cunt and it would spasm and more and more juice would trickle down my legs.

The Professor was really going to town on my pussy and he was pounding me so hard that he would also push the butt plug deeper in my ass with each thrust. I managed at one time to look up and saw that my Mom and Aunt were standing in front of us and looked like they were ready to do something. I gave it no more thought as I heard the Professor getting ready to blow his sticky white seed deep in my cunt. I guess that was the signal the ladies were waiting for because just then they reached out and grabbed the end of the two ropes and quickly unwound the ropes that had encircled my tits for the past few hours. The pain of that blood rushing back into my tits was excruciating and I was screaming in pain as the Professor unloaded his cum in me. The combination of his ejaculation, the pains in my tits, the fire still burning in my nipples and I started to cum like never before. It was the pinnacle of orgasms the one to write home about and it stormed through me for a half an hour. I was so exhausted after that my Mom and Aunt gently removed the plug from my ass and carried me to their car and took me home. I slept straight thru Sunday and woke up sore but refreshed early Monday morning.

My first thought was to count the days till next Saturday then I counted to Thursday. Then I said fuck it and stuck one hand on my pussy and took the other and tried to fist my ass. I could not wait for next week’s lessons.

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