Preppy

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Young preppy gets his comeuppance.
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I grew up a privileged preppy. My father inherited a modest fortune and managed to turn it into a substantial fortune. He did it mostly through wise investments. His investments yielded considerable income. He did not own or operate any businesses. His business was his investments.

That left my father considerable time on his hands. Time, he spent chasing and seducing women. He was quite the lady's man. My mother was content to live the life of luxury and social position. She knew of course, my father was a philander, but chose to turn a blind eye.

My name is Chatsworth Osbourne III. There will be no IV as I hate that name. Like my father, I developed a taste for pussy at a young age and entered College determined to bag as many ladies as I could. I got into a small but prestigious University, not on grades, but on my father's monetary gifts to the University. I understood completely and did not give a rat's ass. It was the rich snooty pussy I was after.

My Grandfather, the original Chatsworth Osbourne, had secured a small fortune through hard work and devotion to family and business. How his son got to be the philanderer he became is a mystery to me. I didn't know nor did I care. There was only one thing for certain, I was my father's son.

Normally my hunts for pussy were centered with girls around my age, but that changed shorty after arriving at the University. The University President had a middle age wife that oozed sex and she literally made my tongue hard. Damn, I wanted to bag that old broad.

What I didn't know was my father had fucked her many times with the tacit approval of the University President. Seems the President had achieved his position by the substantial money he raised for the University endowment fund. Helena Scarberry was a decided asset for her husband's fund-raising activities.

Helena was the chaperone for the first sorority dance I attended at the University. I quickly made my move and asked Helena to dance. She demurred saying there were many pretty young girls my age to dance with. But I persisted and took her in my arms and onto the dance floor. Soon I was grinding my very hard cock against her abdomen. She pretended not to notice and started small talk by telling me she knew my father and how appreciative she and her husband was of his generous donations to the University. Then it hit me, my father had fucked Helena.

As far as I knew my father and I had not fucked the same female before. I was now going to change that, or at least, I was going to give it the old college try.

The dance ended much too quickly for me and Helena moved away. The next dance was lady's choice and a young hottie grabbed me and out on the dance floor we went.

I had been grinding my cock on Helena, now a hot young thing was grinding her pussy on me. Normally I would be hot to fuck her, but my hots were for Helena. She had caused my balls and cock to ache. If I didn't fuck her, I was in for a serious dose of blue balls.

Helena was acting as the perfect hostess and chaperone and I was not able to get her back on the dance floor. Little did I know she was thinking the young Chatsworth had a cock even bigger than his dad. I had lit a fire in her and was totally unaware. She needed my cock as much as I needed her pussy. But this Chatsworth had no clue.

I had pretty much decided on fucking Sally Ferguson to relive my aching balls and cock. Sally was a spoiled young lady and used to getting her way. The kind of girl I had known in high school. But fate was about to step in.

Much to my surprise, when the last dance was called, Helena came to me said, "I hope you saved the last dance for me."

While dancing, my hard cock was once again grinding on Helena's abdomen. This time there was no pretense and she grinded back. I tilted my head and kissed her on the neck, followed by some nibbles. Helena literally swooned and I knew she was mine for the taking. But where was racing through my mind.

I was stunned to hear her say, "I have a small apartment just off campus. I will give you the address. Meet me there after the dance."

I headed out of there as fast as I could and was waiting impatiently until Helena showed up at the apartment. The apartment was kept as a place for Helena to meet with perspective donors to the University. I assumed my father had fucked Helena in this very apartment.

When Helena arrived, she found me in an embarrassing situation, I had my cock out and was stroking. The sight of my cock caused her to gasp.

Once inside Helena dropped to her knees and engulfed my cock. Her warm wet mouth was sending perverse thrills through my entire core. Damn, this hot old broad was a marvelous cocksucker. I stood rigid as she boobed up and down on my cock applying awesome suction. I could feel a huge orgasm welling up inside of me. This old cunt was about to taste the spunk of Chatsworth Osbourne III.

Over my moans, I could hear Helena mewing. She was enjoying sucking my cock as much as I was enjoying her sucking me.

Unable to control myself, I let loose a huge load of cum as my orgasm overwhelmed me. I pumped a copious amount of cum in her mouth. She gurgled as she struggled to swallow it all, Cum-was coming out the corners of her mouth and even out her nose. I had just received the blow job for the ages. I fell back on a sofa and could hear Helena smacking her lips. She was not wasting any of my cum.

As I was coming down from my orgasmic high, Helena said, "Chatsworth that was awesome, but now time for you to return the favor." Obviously, the old broad wanted me to perform cunnilingus on her Something I had rarely done, but was more that happy to give it a go.

Helena got off her knees and began slowly removing he clothes. She was doing a very sensual strip for me. My cock was beginning to rise again.

I jumped up and whisked off my clothes. Soon we were standing bare ass naked in front of one another.

The old broad had magnificent tits with just a hint of sag. Elongated tan nipples that stood out indicating a state of arousal. Her pussy had a closely trimmed bush with a protruding clit. Her flared hips were those of a woman built for fucking. Damn, she was awesome. I could see why my father and pursued and fucked her.

Helena dropped back on the sofa and spread her legs. "Get to eating Chatsworth," she said.

It was obvious who was in charge, but I was determined to change that, but it would to have to wait until I had my hard cock in her pussy.

Down I went snaking my long tongue out and licking the length of her pussy lips making contact with her clit. This caused Helena to lurch and cry out. I began eating her pussy with vigor and determination. When I took her clit between my lips and sucked it like a small cock, Helena flooded my lips and face with orgasmic juices as she had her first orgasm. As the old broad was in the throes of her orgasm, I could sense gaining control and the upper hand. She was mine.

I continued to eat her cunt through a series or rolling orgasms until Helena feinted dead away.

Now was time for the coup de grace. I switched positions and presented my hard cock to the entrance of her very wet pussy. I slammed my cock in one huge thrust and buried it deep in her womb banging her cervix as I did. Helena's eyes flew open and she screamed, "Oh my God."

Her cunt was on fire and the heat was obvious to me. As wet as it was, her cunt remained snug as she clamped her pussy muscles down on my cock. I was in the finest pussy of my young life.

As I began fucking her, she started fucking back. It took a few seconds, but soon we were in sync. God what a pussy I thought.

This 50-year-old broad was giving this 19-year-old young man the fucking of a life time.

We were able to achieve almost simultaneous mind-blowing orgasms before collapsing in each other arms on the sofa.

For the remaining semesters of my first year at the University, I fornicated with Helena on a regular basis in her off-campus apartment. For variety I would occasionally fuck some of the young sorority girls. I never suffered blue balls one time in my first year. Afterall I was Chatsworth Osbourne III.

During the second semester of my second year, I got a call from the Bursar's office requesting a meeting. At that meeting I was informed my fees for tuition, housing and books were in arrears and had been since the third semester of my first year. I was informed unless a prompt payment was made, I would have to leave the University.

I insisted there must be a mistake, I was sure my father's office had taken care of these matters, but I was informed that persistent attempts to contact my father's office were unsuccessful.

Then I was hit with the most devastating news, my father had committed suicide. It seemed his magical talents for investing had left him and he had reached financial ruin. My family home was taken for payment of debts. I was left with nothing.

I went to the home of University President to plead my case. He told me he would not help me one bit even if I sucked his soft cock.

I took my situation to Helena and the old bitch just laughed at me saying, "Chatsworth surely you do not think you have the only big cock around."

Fast forward two years. I live in a skid row apartment which pay for with money I make sucking cocks for rich dudes like I once was.

I'm a preppy no more.

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