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Authors: Lillian Jacobs

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BOOK: Fifty Shades of Gatsby
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It seemed like forever since I had seen Gatsby, strangely, as I had tried unsuccessfully to remove him from my thoughts. It took me a while before I finally found him, looming in the background, sitting in a corner watching
me in his tuxedo. I was dancing with a nice gentleman, and was trying out the latest dance craze. Gatsby watched me, ignoring the other beautiful women – models and actresses twirling about – keeping his gaze focused solely upon me.

I made it a point to not approach him, yet many times he seemed to be near me or by my side, as if waiting for me to be the first to say something. When Gatsby talked with others, enthusiastic as they were to speak to him – he seemed distract
ed, his eyes unable to withdraw from my direction.

“He’s obsessed with you, you know,” Jordan said. “All he has been talking about tonight is Daisy-this and Daisy-that. It’s getting annoying. Go talk to him already and spare us all.”

“I’m sure you’ll do just fine with or without me,” I said to her as two men in three piece suits grabbed her by each arm and she happily followed them into an empty room.

As the evening turned into another night of debauchery, I wandered towards the courtyard.

“Are you so captivated by my party that you must walk away from fear of overexcitement?” Gatsby said, emerging from the shadows with a sly smile.

I smiled back.

“You got my number,” I said.

He smiled and lingered on my eyes, sending chills down my spine. I was feeling reckless tonight and decided to press on.

“I assume that is why you are here as well?” I said.

“You got it. I
guess we are both just a little excitable,” he laughed.

We flirted back and forth before I found myself drawn to a dark room. I felt his lips against mine and returned his kiss, unable to resist.

“It was my fault. I disrespected you and made you angry,” he said, softly and genuinely.

“I’m not just
one of your flapper whores,” I said.

“I know. I felt horrible making you feel that way.”

He seemed genuine and didn’t seem to mind me looking into his deep eyes. I wondered what secrets were behind them. I felt they were true in this moment, no matter the lies he had told in the past.

“I wasn’t mad for that long,” I said. “Besides, I can’t be that sensitive if I can handle the flogger.”

“It was still wrong of me to try and use you like that. I guess I just got crazy with power.”

“It’s okay,” I said, stroking his cheek. “I am starting to understand how powerful men think.”

“But that’s just it,” he added. “I’m not really that powerful.”

“What do you mean?”

He sat down with me on his lap and spoke quietly as the party raged outside.

“I was born in North Dakota, like I told you before. But it was on a farm. We were very poor. I dropped out of a low-level college after two weeks because I no longer wanted to be a janitor to pay for my tuition. So you see, I am not from a successful background.”

“But you are successful now,” I said and kissed him. He kissed me back.

“I feel successful being with you at this moment,” he breathed out.
“I just want things to go back to the way they were yesterday.”

Gatsby moved his mouth down my neck before pulling my dress over my head. He moved to my breasts and sucked and licked my nipples as I writhed beneath him. I tried to pull off his
bowtie, but he stopped me, before moving even lower, plunging his mouth between my wet lady-lips, bathing them with his hungry tongue. I moaned loudly and thrust my hips towards his face as his rapidly licked and sucked, covering his face with my juices. He used his tongue to spread my lips and find my clitoris and focused his attention on the little nub, teasing it until my leg began to shake uncontrollably. I shuddered and groaned as he grasped my buttocks with his hands and rapidly devoured my core. I yelled out in climax, though my screams were drowned out by the rowdy noises of the party outside.

“Fuck me, Master!” I yelled. He got up quickly and grabbed his trunk of toys.

He pulled out two clamps and kissed me before placing them on my nipples. I yelped at the pain before feeling a growing excitement. Between the clamps was a gold chain that he pulled on to stretch out my nipples. I whimpered and lunged at his mouth. Gatsby, now dripping with sweat and my juices, was no longer the clean and dapper gentleman of last night. He pulled out his member and inserted it within my awaiting opening. It squeezed in slowly and we moaned in unison as it slid in wetly. Gatsby grabbed the gold chain with his mouth, grunting and pulling on it as he pumped into me, staring at my chest glowing in the moonlight.

He pulled on the chain, lifting my breasts up, as I inhale
d deeply and softly moaned. Another tug and my nipples became taut and the pain became pleasure as his manhood engulfed my being. His thrusts became more rapid and I felt him climax before we fell asleep in each other’s embrace.


I woke up that morning alone on the couch. I had spent the night! I ran outside to see a huge mess. There were wild animals running around and people passed out naked all over the lawn. I managed to run back to Jordan’s house in ten minutes, but Tom was awake. He had been up all night waiting for me. He was furious and threatened to kill me and Gatsby.

“He’s a bootlegger! That’s how he made all of his money!”

“No, that’s not true!” I said, unbelieving.

“You are associating with a criminal. The lowest scum of the earth! I swear if
I ever see you with him again I’ll kill you both!”

If it wasn’t for Jordan running to protect me, Tom might have killed me right then.

I didn’t visit Gatsby for a week, and Jordan reported to me often that he had not stopped thinking about me. That he wanted to see me. That he loved me. She showed me letters he had written, but I could not read them. I was married and there was no escaping that life.

One day, Gatsby showed up on our doorstep, to my shock.

“You can’t be here,” I said to him.

“I have to see you, Daisy,” he pleaded.

Tom was out for the day so I knew that I had the afternoon free. But I was so fearful for not only my safety, but Gatsby’s.

“We can’t,” I said.

“You signed the contract,” he countered.

It was true that
I did want to see him, as our time together was always so very exciting. I slipped away without a word to Jordan and we made our way back to Gatsby’s mansion.

He fell on top of me upon his humongous bed. Our passion was unleashed and I felt as though we had to release what had been pent up th
e entire week. I closed my eyes as he traced my body with his mouth. Suddenly, I felt restraints strapped onto my wrists.

“What is this?” I asked.

“Well, since you won’t come visit me, I am going to make sure you can’t leave,” he said with a sly smile.

“Very funny,” I said, trying and failing to move my arms.

Gatsby then snapped them onto my ankles as well. I struggled to break free, but it was futile. I felt a shot of adrenaline and my heart rate increased. I felt a shiver as he spread apart my buttocks and rubbed petroleum jelly within.

“Oh my God,” I moaned, as he caressed between my cheeks. “Don’t stop, Master.”

I cringed as he stuck his finger in deeper.

Breathe slowly and relax,” he whispered into my ear.

firmly pushed it deeper until his entire finger was inside, moving in and out slowly. I squirmed as he inserted a second finger and groaned, pulling at the restraints.

“I am going to insert this within you. Do you understand?” he said, holding a small plug.

“Yes, Master,” I moaned, completely under his power.

I relaxed as Gatsby pushed it against my anus and slowly squeezed it inside. The pressure was overwhelming and I could not help but yell out. Before long, it had
completely disappeared within me.

If I ask you to wear this for the rest of the day, you have to,” he said.

“Yes, Master,” I responded, though I doubted I could.

I took a great chance coming there that day. I must have known that it was special, I thought. That he was special, somehow.

I felt a rush as he touched me, and took in his scent.
Gatsby’s every touch increased my pleasure tenfold, as the plug served as a constant juxtaposition of sensation. I felt an uncontrollable desire growing within as he moved and caressed his fingers lightly over my body. He positioned his throbbing manhood to my mouth, allowing me to wrap my soft lips around it. He pumped into my face a few times as I gently sucked his hardness. After some violent thrusts while grasping my hair, he removed himself and I licked my lips. Between my legs, I felt a warm wetness and begged him to enter me.

I wildly arch
ed my back, lost in the moment, as he stretched me out, penetrating me with his engorged member. The gush of my juices ran down my legs and he delved deeper than I thought possible. I felt completely filled up at that moment, as the plug was still firmly encased within my buttocks. I wiggled and writhed as he thrust within me. The rhythm of his movements were very slow and then faster, and grew in speed as the ecstasy built to a crescendo.

“Let me out of my restraints, Master,” I begged.

“You do not-”

“I want to show you
something,” I said confidently.

He took me seriously and in a strange turn, actually stopped and then set me free. I immediately pushed him
onto his back and straddled him. He smiled, staring up – perhaps in an unfamiliar situation. I pushed down on top of him and moaned as my hips rocked back and forth incredibly quickly. He grabbed onto my buttocks and I rode him like a wild horse.

“I’m gonna cum,” I deeply moaned, as we moved in unison. I felt my juices drench his expensive slacks as I bounced up and down furiously. I look
ed down at Gatsby and closed my eyes tightly, feeling his rock hard manhood ignite every nerve in my body and I came once more, flooding his slacks once again as I screamed out. I collapsed weakly, my body still shuddering and he continued to thrust into me. I felt another wave coming and I rode it to another orgasm, synchronized with one of his own. I threw myself off of him and shivered as my body was still tingling. He removed the plug and threw it across the room.

We lay listeni
ng to each other’s heavy breath.

“So what are you going to write about in your article?” Gatsby asked.

“Hmm, let me see. Floggers, whips, restraints…should be interesting. Maybe I’ll win the Pulitzer.”

Haha. No, really. I’m serious,” he said.

“I don’t know. I may not write it. I don’t really want to reveal the truth about you.”

“Why not?”

“Why reveal to the world what I want for myself?”

He smiled and kissed me.

“It doesn’t matter anyways. I own
your magazine.”

jokingly hit him in the arm and laughed.


A loud, unrelenting knock on the door could have only been Tom. Gatsby said he would take care of it and I ran to hide in the bathroom. I heard yelling and arguing before coming out myself. I could not hide any longer. I had to put a stop to this.

“Now listen, old sport. You got the wrong idea,” Gatsby said.

“Old sport-this and old sport-that. That’s all you ever say. You are nothing but a liar! I know that you never went to Oxford!” Tom yelled, obviously drunk and in a dangerous mood.

“Maybe I did and maybe I didn’t. Doesn’t matter to you, though, does it, old sport?”

“What are you doing with Daisy? She is my wife!”

“She loves me, not you.”

“Is that true,” Tom asked me. “You’re in love with a criminal? A bootlegger?”

“Yes, I am!” I yelled out.

“Fine, then stay with him and see how you like it!” Tom yelled and ran out the door crying.

Gatsby ran over to me we embraced.


I awoke the next morning to find Gatsby floating in the pool.
He was swimming so I joined him. We relaxed the entire day and Jordan even came over for a bit. We all fooled around in bed and that night during a party bonfire we burned the contract.






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BOOK: Fifty Shades of Gatsby
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