Jimmy's Whore

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

My brother asked me to help him out with some trouble, and I get more than I bargained for.

I love my brother Nate and have always had a close relationship with him. Because of him, I’ve never gone without. He’s always taken care of me, much better than our parents did. With coming from a poor family in the roughest part of the city, Nate turned to crime to help us survive.

Nate was the tall dark-haired good-looking bad boy that all the girls fancied, and his best friend was a boy called Jimmy Kelly. Jimmy came from a well-known criminal family that was feared in our city. I had a crush on Jimmy for years, he was a tall well-built, blond-haired bad boy that had the bluest eye’s I’d ever seen. And boy did I want him and with the way he looked at me, I knew he wanted me too. But Nate wouldn’t allow it, so out of respect for their friendship, Jimmy wouldn’t come anywhere near me.

Jimmy and my brother had a whale of a time screwing all the girls in our neighborhood but when it came to me shagging about, that was a big fat no. No one was allowed to touch Nate’s sister. I remember when his friend Shaun took me to the cinema, I sucked cock for the first time. When Nate found out, he and Jimmy beat him bad and I never saw him again.

I thought I was going to die a virgin.

A week before my nineteenth birthday, Nate came to my bedroom and stood in the doorway staring at me. I could see he was stressed. “What’s wrong Nate?” I curiously asked.

Nate rubbed his face with both hands and looked at me. “I’ve got myself into big trouble with Jimmy. I need you to come with me to help smooth things over.”

“What?” I laughed, “What’s it got to do with me?”

“Please Lizzy, he wants to speak to you, alone.” Nate looked seriously at me. “Only you can help me.”

“Ok, wait for me in the car while I get changed,” I smirked as I rolled off my bed thinking this was it, if Nate wanted my help, then I was going to get what I wanted, and that was to take advantage of being on my own with Jimmy and finally lose my virginity to him.

I quickly sorted through my wardrobe and found my little black lycra dress. I took my bra and thong off and slipped into the black dress and applied my makeup then ruffled my hair with my fingers. Standing in front of my full-length mirror, I turned around inspecting every angle of my body and smiled. I knew Nate would go crazy when he saw how I was dressed but I didn’t care. If he wanted my help, then I was going to damn well dress how I wanted to.

As I walked to my brother’s car I braced myself for a torrent of abuse, but he said nothing. Nate just side glanced at me, started the engine and we drove into the city.

Parking outside an apartment block in one of the wealthiest parts of the city, I was impressed as I climbed out of my brother’s car and gazed up at the apartment block in front of me. I didn’t think Jimmy was wealthy enough to live there.

Taking a key out of his pocket, Nate unlocked the security door and I followed him into the reception area. Nate was unusually quiet as we took a lift to the top floor. Taking another key out of his pocket, he used it to enter an apartment. As we walked in I could hear Jimmy in the bathroom having a shower. I stared in awe at the living room with its cream carpet, black leather sofa and dark wood units with expensive ornaments on. I thought to myself there was no way that this is where Jimmy lived.

I stood by the window and gazed at the city below thinking how pretty it looked at night then turned to face my brother. “Are you going to tell me what Jimmy wants to see me for?” I curiously asked.

Nate couldn’t look me in the eye as he nervously ran his fingers through his hair. “Jimmy will tell you, I’m sorry I’ve got to go.” He mumbled rushing out of the apartment.

I stood by the window and watched my brother climb into his car and drive away. Knowing that I planned to seduce Jimmy, my body tingled with excitement as I walked over to the mini bar in the corner of the living room and poured myself a glass of wine and took a sip of it.

“Do you like my wine?” I heard a deep voice growl behind me.

My heart thudded in my chest, that wasn’t Jimmy’s voice. I slowly turned around and saw a large built man covered in tattoos with short salt and pepper hair standing in the doorway with a white towel wrapped around his bottom half, little drops of water were slowly running down his bare chest.

“Hello, Lizzy.” He grinned looking me up and down. “You’ve grown quite a bit since I last saw you.”

“Mr. Kelly!” I gasped, I couldn’t believe my eyes, Nate had brought me to see Jimmy Kelly, but it wasn’t his friend Jimmy, it was his father who had the same name. “I thought you were in prison for eight years!” I took a step back as he walked towards me.

“I was released today.” He grinned showing the deep dimples in his cheeks. He poured himself a glass of wine and turned to look at me. “They let me out early for being a good boy.”

Oh god help me, I thought to myself as a took a massive gulp of my wine. My heart was still thudding in my chest I could barely breathe.

“Unlike your brother, he’s been a bit of a naughty boy while I’ve been away.” He said looking at me with amusement. “He owes me a substantial amount of money.”

“What’s that got to do with me” I nervously asked trying hard not to stutter.

“Come on Lizzy, you know why you’re here,” Jimmy grinned taking a step towards me placing his hands on my waist. “It’s been a lonely four years inside,” He deeply sighed gazing into my eyes. “You can ease my loneliness and clear your brother's debt.”

I nervously swallowed as I looked up at Jimmy. He was built like a monster compared to his son, but the way my stomach was swirling, I wanted him. “Ok,” I sweetly smiled. “So, my brother's debt gets cleared and you get me, but what do I get out of this?” My heart raced as Jimmy leaned forward.

“You get the hardest fuck of your life.” He growled in my ear.

Oh god, my legs turned to jelly. “But I’ve never done it before,” I whimpered.

A growl rumbled in Jimmy’s chest as he breathed in deep and closed his eyes, “It’s been a long time for me Lizzy, I nearly shot my load then.” He grinned as he opened his eyes.

I dropped my glass as he grabbed me around my waist and pushed me against the wall and let out a moan as his deliciously warm lips crashed against mine. I could barely breathe as he roughly kissed me, grinding his body against mine. I could feel his hard-on through his towel. Jimmy suddenly moved away and looked at me, he grabbed my arm and marched me out of the living room towards his bedroom. He pushed on the bed and opened his towel to reveal his huge thick hard-on. “Come here,” He growled, “Suck it.”

I didn’t need to be told twice. My heart raced with excitement as I crawled across the bed towards him gazing into his eyes that were full of lust for me. I gripped the base of his cock and massaged it feeling every throbbing vein then rolled my tongue around the end of it tasting his salty pre-cum. Jimmy groaned raising his hips as I slowly licked up and down the sides of his rock hard shaft then slowly sucked his meat as far as I could into my mouth gagging a little as it touched the back of my throat. Jimmy wrapped my hair around his hand and held my head down, he groaned loudly and began to thrust into my mouth. He suddenly stopped and forced his cock deep into the back of my throat. I relaxed taking it deeper, I wanted to please him. Struggling to breathe, I choked as Jimmy forced his dick deeper down my throat as he fired his hot seed into it, groaning and jerking until every last drop had spent. He released my hair gasping for breath as I gripped the base of his cock, sucking and licking it until he went soft.

I kneeled on the bed and looked at Jimmy, “What would you like me to do now,” I sweetly smiled glancing down at his flaccid cock thinking that maybe it was all over now.

“Don’t worry about that,” Jimmy grinned when he saw me looking at his limp dick. “It won’t be long before its ready to go again.” He laughed. “Now take that dress off.” He ordered stroking his large warm hand up and down my leg.

My body began to shake, I’d never been naked in front of a man before but there was something about the way the tattooed older man was looking at me that made me want to obey his every request. I hooked my fingers under the hem of my dress and slowly raised it and pulled it over my head then threw it across the room. His eyes widened at the sight of my naked body in front of him. I squealed as he sat up and grabbed me by my waist and pulled me over him. Jimmy laughed as he lay back on the bed, gripped my hips, and raised me over his face like I was a feather.

I could feel his warm breath between my legs as he kissed and sucked on the inside of my thighs. I let out a loud moan as his hot tongue slowly licked along my slit sending shudders down my spine. I held onto his head and ground my pussy against his face moaning with pleasure as his tongue hungrily licked my soaking wet hole. My stomach tightened at the feel of Jimmy’s muffled groans vibrating through my core. It felt like electric shooting through my body when he latched onto my clit, my core was on fire, I could barely breathe. Grinding harder onto his face, I threw my head back and howled with pleasure as my orgasm raged through my body like wildfire. Jimmy gripped my hips pulling me down onto his face groaning with pleasure, drinking my juice as it gushed over him.

“That was fucking sweet.” He growled as I flopped onto the bed.

I just giggled I had no strength to move, I was a quivering mess.

Giving me no time to recover, I stared wide-eyed at Jimmy as he opened my legs and kneeled between them stroking his rock-hard shaft. My heart pounded in my chest as he rubbed the tip of his cock along my slit searching for my entrance. “Relax Lizzy or it’ll,” he stopped talking and groaned as he eased the tip into me. My body tensed with the pressure of my virgin hole stretching. “This is going to fucking hurt.” He grinned thrusting his steel hard cock into me, grunting with aggression forcing me to take every inch of him in one thrust.

I held onto Jimmy’s arms crying in pain trying to push him away from me as he held his cock inside me stretched my virgin hole to its limit like he was savoring the moment taking my virginity.

Jimmy painfully gripped my hips and began to thrust into me. Gasping for breath, my body shook with the power of his shaft hitting my g-spot with force. The pain slowly turned into pleasure as he drove deeper into me. I arched my body and howled as the heat of my first orgasm exploded from my core to my head.

Jimmy stopped, grabbed my legs, and threw them on his shoulders, he leaned forward almost bending my body in half and rested his hands each side of me. He was pounding deeper into me, tears streamed down the sides of my face as I looked up at Jimmy. I was going to tell him that I couldn’t take any more, but his head was down watching his thick cock pumping into my virgin hole like a well-oiled piston. I held onto his arms as leverage and raised my head to watch too, oh my god it was an amazing sight, it drove me crazy. I let out a loud moan as another orgasm raged through my body like wildfire, I didn’t want him to stop. “Fuck me harder,” I screamed.

A loud deep growl rumbled in Jimmy’s chest as he threw my legs off his shoulders and lay on me. “You fucking whore,” He groaned ramming himself into me. I bucked my hips howling in pleasure rolling my head from side to side as he crushed my body into the bed. Sweat poured from Jimmy’s forehead, the headboard banged against the wall. “Whose whore, are you?” He growled

“I’m your whore,” I squealed with a mixture of pain and pleasure.

Jimmy let out an almighty groan, took one last thrust and held himself deep inside me as he cum.

I gripped my nails into his back moaning in ecstasy from the feel of his pulsating cock pumping his hot cum inside me.

Me and Jimmy passionately kissed grinding our sweat-soaked bodies against each other for what seemed like forever.

 

When Jimmy left the bedroom to go and get a drink I searched around the bedroom for my dress and was about to slip it on when he returned. “What are you doing?” he asked placing the two glasses of wine on the bedside cabinet.

“I’m going home now,” I answered thinking the night was over.

“You’re not going anywhere,” He grinned walking towards me grabbing my dress and throwing it across the room. “I haven’t finished with you.”

“What!” I gasped in disbelief. “You got what you wanted, what more do you want from me?”

“I’ve just told you, you’re going nowhere.” Jimmy wrapped his arms around me and grabbed my ass. “I’ve still got another virgin hole to break in.” He grinned squeezing my ass cheeks.

…………

Well, I never left Jimmy’s apartment that night. In fact, it’s now ten years later and I’m still there. I never returned home. Me and Jimmy were married the following year. Everyone said it wouldn’t last with our twenty-five-year age gap, but we proved them wrong. As for my brother, he couldn’t apologize enough for setting me up with Jimmy. I told him there was nothing to forgive because now I couldn’t be happier with my life. Jimmy Kelly is the love of my life, we have an amazing life together and I want for nothing. He treats me like a princess and he still fucks me like a whore.

 

 


Submitted: May 17, 2020

© Copyright 2021 Kitty Hall. All rights reserved.

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Comments

Storywriterx

WOW!!! That was so hot and well told from the moment he dropped his towel. I enjoyed your naughty wording describing the sex and the unexpected ending.,XoxoX SWxx

Mon, May 18th, 2020 3:23am

Author
Reply

Thank you, I enjoyed writing it and I do like little twists in my stories. :)

Mon, May 18th, 2020 11:20am

Amy F. Turner

Yum, yum. I definitely enjoyed reading this tasty morsel again. Thanks for bringing it back for another sample. So hot, Kitty. So smoking hot. Older men who are bad boys are such a week was when this good. ;)

Mon, May 18th, 2020 2:18pm

Author
Reply

Thank you, I enjoyed rewriting it, Older men are definitely hotter :)

Mon, May 18th, 2020 11:59am

DampKitten

Okay, I'm sorry...I have to PM you later but I got on here for a minute and just had to see WHAT THE FUCK THIS WAS! Holy shit! I see this thing that says "here's what the people you know are reading"....so I click on it and BOOM! Your name's on it!

I absolutely love this! You're killing me with this new found erotic streak...okay, you're "Bringing Sexy Back" (see Justin Timberlake). I know this is some of your older stuff but it's new to me.

What I really like about this is how you fake me out on who Jimmy actually is...well, you fake out your main character too! And wait just a minute! This is first person narrative! OMG! Look at what you can do!

HOT AS HELL, GIRL!!!

Thu, May 21st, 2020 11:33pm

Author
Reply

Haha, thank you. With this being an old story I had a lot of editing to do. I have a whole book written in the first-person that I'm thinking of uploading soon. :)

Fri, May 22nd, 2020 5:53pm

Joex

Another great story. Very erotic. Thank you.

Mon, August 3rd, 2020 12:21am

Author
Reply

Thank you. :)

Wed, August 5th, 2020 1:13pm

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