Read Fifty Shades of Gatsby Online

Authors: Lillian Jacobs

Fifty Shades of Gatsby




Fifty Shades







Lillian Jacobs

© 2013 by Lillian Jacobs




Daisy’s dream comes true when she has a chance to meet the wealthy and mysterious Gatsby, a notorious playboy known for his wild parties and indecipherable past.


Her desire to discover his true nature, and his urge to dominate in and out the bedroom - in any way possible - ignite the sparks of their passionate affair.




The jealous rage of Daisy’s husband and Gatsby’s uncontrollable obsession converge in this erotic parody of The Great Gatsby.






In my younger and more vulnerable years, my mother gave me some advice.

“Whenever you feel the urge to give into rich and powerful men, don’t.”

I was very vulnerable back then, and had only been with one man, my husband. His name was Tom, and he was a lecherous drunk. You know the type. For me, Daisy Carraway, one man for my entire life was my chosen path. I did not care if other girls lived differently than I. From a young age, I learned not to judge others. My father taught me that, not my mother. I was taught to not hold them up to the same standards as myself, because I do not know them. You never know what their past was like – and until you know that, you can never know them. We all come from different backgrounds. Therefore, I have become highly tolerant.

Gatsby, one of great wealth, success, and power was the best and worst thing that could have happened to me – but
never judged him. I tried to never judge him – no matter what happened. It was hard, no doubt. The fact that he was completely gorgeous helped in many regards. I am not superficial, but there must always be attraction. Did I mention how gorgeous he was? You know the type.

The year was 1922, and I just came from New York. I was an innocent, young girl, with hopes and dreams, like anyone else my age. I wanted to get into journalism and hoped to write a story on the rich members of the aristocratic West Egg. This was a very wealthy neighborhood and the subject
matter had always fascinated me, as I had no money of my own to speak of. Those that lived in the West Egg were those that were “new rich,” and had just gained their money, as it wasn’t inherited, unlike those in the East Egg. They were the ones who were not used to the power – to them it was something new and exciting. They were also the ones that made fortunes themselves – so you knew that they were special, smart, and had a hunger for power. Those in the East Egg did not do the work to acquire their fortune; it was given to them.

The mansions in the West Egg made my mouth water
and my loins tingle with the thought of rich men; though I told myself to not be a typical gold digger with dollar signs in my eyes, I could not help it. This was an age of decadence.

My husband, Tom, and I were staying with a friend of mine in W
est Egg. Tom was a handsome man with gravely facial hair, and always wore the most striking three piece suits. His weakness, however, was his temper, and it often got the best of him. He played football in high school and college and was a typical athlete. The qualities that attracted to me to him in the first place were the ones that I soon grew tired of. One of them – his aggressive nature towards women – didn’t end with our marriage and I was sure that he was seeing others on the side. He was certainly not rich, but he always tried to take control of a situation, and that was enough, most of the time. Though, in the bedroom, many times his attempts to gain control only ended in flaccid results.

“Now, just because I’m more successful than you, doesn’t mean I want to push you down. I want you to get your story. I’m here to help,” said Tom.

“Thanks, honey. I appreciate it,” I said, sarcastically.

“Now what is the name of th
is magazine, again?”

I told him.

“Never heard of it, before,” he said, and the conversation ended.

at really pissed me off.

We arrived at my friend’s mansion in West Egg. Her name was Jordan and we knew each other
from university.

“Daisy!” she yelled as she ran down the steps and hugged me. I noticed
that in front were fountains and luscious foliage that would look great for my story pictorial, if she allowed me to photograph them.

“So this is the one I’ve been hearing about,” Tom said, sizing up Jordan. “I can see why you didn’t want
to mention too much of her. You’re obviously jealous, and rightfully so.”

Jordan just rolled her eyes and introduced herself. She could see my cheeks turned red and smiled in acknowledgment of Tom’s rude behavior.
Jordan was beautiful, though a typical flapper who married rich. I wasn’t jealous – her husband had one foot in the grave. We finally got time away from Tom and walked in the garden. I was enamored with her palace.

“You have been doing quite well, for yourself, haven’t you?”
I said so that she could detect no jealousy.

“Well, not me, but my husband. Sure, behind every great man is a great woman. But still, he’s the one responsible, mostly. That’s why I told you to marry rich.”

“Yes, well it’s too late for that now,” I said, trailing off.

“It’s never too late for anything. Look around you. There are all sorts of incredibly wealthy bachelors around here.”

“Well, I want to make a name for myself. I don’t want to be completely at the will of a man. Not that you are.”

“Well, my husband does need me to provide him that much needed release at the end of the day.”

“Oh, Jordan, stop!” I laughed.

don’t be such a prude. I’m the one that knows want he wants. Powerful men can be pretty kinky behind closed doors. Sometimes they even like to be dominated because they are so used to being in control in every other part of their life. My husband likes it when I make him crawl around and ride on top of him.”

I laughed, as I couldn’t picture such a thing being possible. “How could I dominate a powerful man?”

“I didn’t say all of them were like that,” she added. “Some of them like to dominate completely. Like Gatsby.”

“What’s a Gatsby?”

Before we could continue our conversation, the phone rang. Tom answered it before Jordan could get to it and began talking very quietly. I knew that he was talking to a lover of his that he gave Jordan’s number to. Jordan was about to interrupt him but I grabbed her shoulder and told her not to.

Tom and I
had not made love in over a month. I wondered what was wrong with our sex life – was it me? Was it not exciting enough for him? Should I ride on top of him while he crawled on the ground?

“I’m sorry, Daisy,” Jordan said.
“But you shouldn’t feel trapped. Look around!”

“Maybe you’re right. It will be a good excuse for me to check out the other
men in the area, without guilt. This Gatsby sounds enticing.”

“That’s the spirit. But be careful of Gatsby. Like I said –
he’s a bit of a control freak. A total obsessive.”

“You’ve been with him?” I asked, surprised.

She just gave a devilish smirk.

“I showed him a picture of you when I told him you were interested in interview him. He asked a thousand questions and kept the picture.”

“Interesting…how would you describe him,” I asked, intrigued.

“Where to begin? Incredibly wealthy, gorgeous, and single. Not many know of his past, however.”

We talked for a while about Gatsby and West Egg and how I could meet the man of my dreams
on this vacation. Then Jordan began to describe the different ways in which she pleased her men.

“It’s all in the kiss,” she said.

“So what is so magical about your kiss?” I asked, mockingly.

“Oh, you’ll never know,” she teased, before brushing her lips against mine.

“What are you doing?!” I yelled, shocked.

“Daisy, you are in a different world here. These kinds of pleasures are the norm for us. We get bored here – so much so that any kind of sexual deviation is a necessary
indulgence. Everything here is done to the maximum. I suggest that you expand your horizons if you really want to understand our culture. It will help your article.”

She moved her hands along my thighs and rubbed her cheek against mine.

“You are far away from home, now,” she said, planting a light kiss on my lips which stole my breath and took away my protests. I admit, I admired her touch; it was more soft and gentle than I had experienced. I brought her head close to mine and began to passionately kiss her without shame. We moved each other’s tongues past the barriers of each other’s lips, feasting on the heated caverns within. Her eager tongue easily ran along my teeth and the roof of my mouth. Our tongues seeked each other out, colliding and lazily swirling around together.

Ignoring any reservations, s
he moved her hand between my legs and mine to hers. We felt each other’s wetness before collapsing on the bed. I whimpered involuntarily and gasped as her silky skin rubbed against mine. She exposed my breast and licked and sucked my nipple wantonly before gently tugging and pulling it with her teeth. Jordan spread my legs and I moaned as her soft lips ravenously devoured my core, engulfing me in a world of wicked sensation. I opened my mouth in ecstasy, a silent cry. Her tongue ventured in further, taking me to new heights of pleasure, my toes curling and my leg shaking. I returned the favor, unmasking my own hunger, before we became engulfed in a gentle tangle of wet flesh and all sense of time was lost.


After a few hours, Jordan called out to me and I went to see what was happening. Standing on the lawn outside was Gatsby. This was the first time I laid my eyes upon him and I felt the blood rushing in my body. I had never laid eyes upon a man with such gentle, yet harsh features. A part of his slicked back hair fell upon his forehead, shadowing piercing, grey eyes that stared straight through me. He sat casually with a half smile, his fitted suit resting comfortably around his toned body. I felt as though I was about to faint, but got a hold of myself, focusing on my goal: a story. He moved his hands through the water of the fountain.

“I’m Gatsby,” he said, with a gentle, yet assertive voice.

“Oh, um, hello,” I replied, barely able to speak. My eyes wandered over his body and fine suit.

“And you are Daisy?”

“Oh, yes,” I said. “Sorry. Yes, Daisy.”

He had an understanding smile – a rare smile with such confidence. And his face seemed to concentrate only on me and nothing else. It was as if nothing else in the world existed between the two of us at that moment.

Well, Daisy – if you’re sure that is your name. I’ll see you at the party and we can discuss that article you are writing,” he said. “Let me know if you need anything.”

efore I could form words to respond, he was gone.


After he left, I talked with Jordan and we discussed Jay Gatsby and his past. She said that she had heard was a cousin of a Rockefeller. She stated that Gatsby threw huge, elaborate parties every weekend - all taking place within his overgrown mansion. To be invited to one of these parties was desired by anyone who was anyone. And by anyone who
to be anyone.

Finally, t
he day of Gatsby’s party arrived. I was going to wear something more modest, but Jordan forced me to wear one of her dresses, a scandalous, black dress that was thigh high. She convinced me when she said it would impress Gatsby.

I walk
ed with Jordan to Gatsby’s house, which was nearby. We could hear the crowd from down the street, and the lights shone into the night sky. When we arrived, we were alarmed at the excitement of the crowd and the incredible energy of the festivities. We felt out of place at first, but after a few drinks, we began to relax and roam among the crowd, learning more and more about Gatsby. Some stated that he was a spy for the Germans during the war, while others stated that he attended Oxford, while others believed he was a murderer.

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