Read Fifty Shades of Gatsby Online

Authors: Lillian Jacobs

Fifty Shades of Gatsby (3 page)

BOOK: Fifty Shades of Gatsby
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My eyes scanned the rest of the document
, my mouth agape. I could hardly believe my eyes.

“If y
ou need time to think about it, that is okay,” he said in an understanding voice.

It was incredible that such a wealthy and powerful man was so into me. I couldn’t believe it.
He had gone through so much trouble just for me.

“This is very sudden for me,” I said, nervously. “Do
n’t you enjoy regular sex? Have you heard of the missionary position?”

But we all have our preferences.”

what if I say no?”

“That is completely up to you. But if you do n
ot accept, then you must leave. I am a busy man. Furthermore, you will not have your story.”

“I’d rather not go home,” I said, feeling the story slipping away. I grabbed the pen and signed it without analyzing it further. What’s done is done
, I thought.

flashed a smile.

“Now, there’s a difference between being violent and being physical within BDSM. I would never get angry with you and hurt you. I promise you. A
lso, you can stop me at any time.”

“That’s reassuring,” I said, relieved.
“I think I can trust you.”

“After this
you will trust me more than anyone else in your life.”

You enjoy BDSM?”

fits with my life, especially my business life. Over the years I have become ruthless. I take out anyone that competes with me – that desire to dominate translates to my private life.”

“I see,” I said and began writing notes in a pad.

“Why don’t you take care of that later,” he said. “Besides, I want certain aspects of my life kept secret. By revealing this part of my life, you would also reveal your own, thereby ruining your reputation. I can afford it – you can’t.”

Of course,” I said.

“Why don’t we start over?
I feel like we got off to a bad start,” he smiled. “Go outside again and knock.”

“Um, okay,” I said, adjusting my dress, which I had spent all morning stressing over – fretting over whether he would like it. He
hadn’t commented on it, but things seemed to be going well.

I walk
ed back outside and then knocked again.

“Come in,”
he said, assertively.

I walk
ed inside and saw him sitting comfortably on his leather couch smoking a cigar. I curtsied and asked whether the cigar was Cuban. But he ignored me. I felt as though I was beyond my depths and that at any moment, things would take a turn for the worst. He was just playing with me, I thought.

“How are you?” I managed to squeak out.

“Louder,” he said. “And address me as Master.”

I almost laughed until he gave me a stern look.

“Yes, Master,” I replied, not believing the words. I looked into his eyes, which were beautiful in that light.

“Do not look me in the eyes until I say so,” he said, rubbing his chin and examining my body.

“Yes, Master.”

“Good. Now stand still and put your hands behind your back.”

I did as he said. He began to walk around me, looking at me. I felt as though I was under a microscope. I was, however, glad that I had no holes in my clothing and that my hair and makeup were done. If he saw something he didn’t like, I imagine he would kick me out of my house and have me banned from West Egg.

“What shall I do, Master?” I asked.

“Just obey me,” Gatsby said, not looking at my face. “I haven’t ordered you to do anything yet.”

After an uncomfortably long time, he took a few steps back, seemingly satisfied.

“Now walk towards me,” he said and I did. On the wall I noticed a photograph of a woman who was tied up, with a gag shoved into her mouth. A chill ran up my spine, yet my body betrayed me and I felt myself becoming wet.

“Is this to the Master’s liking?” I said

He walked towards me
, looking at me with eyes of fire.

“I told you not to look me in the eye,” he said. “Now
lie down on the couch.”

I did as he said – he seemed angry.

Gatsby reached down and felt the growing wetness between my legs. I was breathing harder and whimpered. He slapped me down there lightly before squeezing my nipples over my dress. I moaned and then he walked over and grabbed an antique Moynat trunk and opened it. It flipped open after he unhinged the latches and I gasped when I looked inside. There were flogs, crops, whips, a collar, clamps, a gag, and restraints.

“Are you going to use these on me?” I asked, meekly.

“They are not so bad once you get used to them. Like I said before – boundaries must be constantly pushed.”

He grabbed the flogger and brought it to
my lips.

“Kiss it,” he commanded. I did

“Stand up,” he said. I stood up. “Now get undressed.” I got undressed slowly, revealing my undergarme
nts and garter belts. I unstrapped them and slipped down my panty hose. I felt embarrassed, being naked, while he was completely dressed, looking incredibly dapper. I felt a shiver as I complied and stood bare.

“You’re skin is milky white,” he said. “Very nice. And your legs are long and exquisite.”

My breasts rose and fell nervously as my breathing became more labored. He assessed my body, examining every inch, while I waited patiently. 

“You are quite beautiful, Daisy,” he said pulling two earrings out of his pocket. They were diamond and gorgeous. “I want you to have these.”

I couldn’t help letting my eyes widen. I didn’t want to seem impressed, but I was. I had never seen diamonds so big. I plucked them from his hands and put them on. Now I was wearing only earrings. He took a step forward and attacked my mouth, letting his tongue guide along mine. He was more aggressive than I, yet it was hard for me to not attack him as well, as my arousal was becoming uncontrollable.

“Now bend over the couch,” he said. “You must be punished now.”

“What did I do wrong?” I asked, confused.

for starters, you came later than expected. Also, you looked me in the eye when I explicitly told you not to. But I will go easy on you now since it is your first time.”

I bent over, trying to point my buttocks up, as he gently caressed my thighs and cheeks
. I closed my eyes in anticipation of the pain.

He swung the flogger against my buttocks, yet it was gentler than I imagined it would be.
He struck firm blows and I squealed.  It began to sting and I squirmed and wriggled around. By the tenth slam, however, he was swinging harder and I knew my cheeks were getting red. Then he began to alternate soft and hard blows, so that I did not know what to expect – yet I still yelped with each blow. To ease my growing pain, he began to massage my dripping wet lips and I moaned in pleasure. He then brought his fingers to my mouth and let me taste my own juices.

He had me stand up and began to massage my breasts, squeezing and pinching my hard nipples before slapping them. Gatsby took both nipples between his fingers and slowly increased the pressure before I began to cringe in pain – then he moved one hand down and inserted his fingers within, flicking them quickly so that both pain and pleasure filled my body.

Gatsby then took out the gag and placed it within my mouth.

“Just breath
e slowly through your nose and do not panic – you will be okay,” he reassured me. “Now bring me a glass of champagne.”

I felt humiliated at the moment – but I was seeing the real Gatsby. And I would find out more when this was over. With a story like th
at, my article would be on the cover. I would be famous. It would be worth it. I poured the champagne with the gag still in my mouth and brought it to him. But before I made it over he spoke.

“Bring it to me on your knees,” he said commandingly.

I got on my knees, making sure not to spill any, and shuffled towards him. When I finally reached him, giving one last grunt, he had his member out, pointing directly at me. He began to rub it against my face, though it couldn’t enter my mouth, as the gag was still on. He grabbed the drink and took a sip, managing to spill some on my breasts, so that it ran between them and down between my legs.

“You want this, don’t you?” he said, as he r
an its hardness against my soft cheeks.

I nodded, as this was a true statement. I wanted to have power over him
sexually. If I went down on him he would be at my mercy. Also, it would be more familiar than everything else that was occurring.

“Do you really want it?” he said, as it danced before my face. I nodded again enthusiastically. He looked so gorgeous, fully dressed i
n his three piece suit, while I was on my knees, naked and gagged, dripping with wine and my own juices. He had complete control. I wondered how I got in this situation – but it was too late to go back.

He removed the gag and threw it violently against the room with the fire returned
to his eyes.

“Beg me to suck it,
” he said, passionately.

“Please, let me suck it,” I moaned. “I want to kiss and lick it all over.”

“Do you want it in your mouth?”

“Yes, Master,” I said.

He put two of his fingers within my nostrils and pulled my head back and then rubbed his member against my pouty lips before sticking it within my warm and wet mouth. I engulfed the hardness and sucked. After bathing him with my mouth for a few minutes, while he moaned and rocked his hips, I began to lick the up and down the shaft. Then in one motion I took the entire thing into my mouth until tears poured down my cheeks.

“You can look me in the eye now,” he said, looking down. I glanced up and saw his eyes raging with passion. He
began to furiously pump it inside my mouth while looking me in the eye and then climaxed. I took it all down my throat before collapsing against the couch. He sat down as well.

I was still reeling from the experience when he spoke
softly to me.

“My real name is James Gatz and I grew up on a North Dakota farm. That is all I will tell you for now.”

Then he commanded me to shower before I left.


When I arrived home that evening, Tom was furious. He ended up hitting me twice – the kind of pain that was not kinky – merely hurtful and violent. I cried for a while before thinking of Gatsby and how I was the one girl that he had chosen out of all of the hundreds of girls he could have. Tom tried to mount me in the night after he had been drinking and I tried to push him off, but he hit me again. Fortunately for me, he couldn’t get it up and fell asleep filled with impotent rage. I escaped the next morning to meet with Gatsby.

He took me out on one of his cars – a 1922
yellow Rolls Royce Silver Ghost. We sped through the barren valley and through the city. A police officer pulled us over but recognized Gatsby and apologized. I was in awe of Gatsby’s power and he knew it. We ended up getting lunch with an old, overweight man who seemed to have bodyguards nearby at all times. Gatsby warned me that he was responsible for the 1919 World Series fix. I wondered if Gatsby’s source of wealth was from criminal enterprise or organized crime, since he was not wealthy from inheritance, as I now knew.

Gatsby and the man began to have a serious conversation that became heated. Gatsby turned to me and whispered in my ear.

“We are working on a business deal right now. It involves a lot of money. As a show of good faith, you are to give him a blowjob. Now I know this wont be easy, but I am your Master. You must do as I command.”

I was stunned.

“No way,” I said, disgusted. “You’re out of your mind.”

The old man looked appalled and took his cigar out of his mouth.

“Now listen, here young girl-” he began before Gatsby interrupted, holding his hand up.

“I am your Master,” he said authoritatively in my ear, while grasping my arm tightly.

“I didn’t sign a contract to pleasure other men,” I said and stood up. “I think this lunch is over.”

I threw a glass of wine in
Gatsby’s face and stormed off. The old man stood up, infuriated and Gatsby apologized before running to catch up to me. He tried to get into an argument on the way home, but I remained silent. I had felt a strong connection with Gatsby and I thought that he had felt one as well. I guess that I was wrong.


Jordan consoled me the best she could, and Tom was his usual psychotic self. I was depressed and confused and miserable. It was only an invitation to another Gatsby party that finally broke my emotional storm. I didn’t want to go. I was done with Gatsby. He had crossed the line. Jordan convinced me to go, however. It would be bad not to try and mend things, she urged. Additionally, my invitation had a personal note from him: I was wrong. I’m sorry.

Jordan was
finally able to convince me to go, unsurprisingly, as we wanted to show off our new cloche hats. That was the straw that broke the camel’s back. We arrived to a lavish scene, as expected. The music blasted throughout the neighborhood and the dance floor and fountain were filled with people doing the Charleston.

BOOK: Fifty Shades of Gatsby
6.28Mb size Format: txt, pdf, ePub

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