Adventures of Hollywood Jim Ch. 18

Story Info
Hollywood gets kinky with Kim Kardashian.
4.5k words
4.53
84k
51

Part 20 of the 101 part series

Updated 02/26/2024
Created 08/06/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"You want me to go where?" I asked Chris wearily.

"Calabasas." He replied.

"And for what?" I responded.

"I need you to deliver some paperwork to this address. They need to sign for it and approve the content." He explained, quickly adding "Hey, I'd go there myself, but my accountant is coming over and this is the only night he has free and our tax return is gonna be a lot more complex this year so I don't want to rush this."

"But wasn't FedEx invented for times like this? I'm beat, man." I protested. "We've been running around the last 2 weeks, we've got another project starting soon and I'd rather not drive all the way up to, where was it again?"

"Calabasas." Chris said again

This was one time when I was about to put my fist through a door. I was right, we'd been incredibly busy lately. Yes, that's good for a business, but not for me.

"I don't even know where that is!" I said exasperated.

"That's why I'm giving you this." And he dropped a set of keys in my hand. It was the keys to his Porsche convertible. He'd gotten it recently and proudly saw it as a symbol of his hard work.

"Take my car, it has the GPS system in it, I programmed the address in last time I was there so it won't be a problem for you." He explained.

"Alright, alright I'll go." I said.

"Thank you. Look, I know I put you in tough spots, but you have to admit that in the end it's worth it, right?" Chris really sounded sincere at this moment.

I looked around at what our work had gotten us so far. We had a successful business that kept getting bigger and better. Yep, we were big time, just like we dreamed.

"I'll even fill the tank for you." I said as I headed out the door with a smile.

The Porsche was one smooth ride as it navigated the highway. I truly felt like the king of the road with the top down, shades on, and Aerosmith on the sound system. And the GPS did work as expected. I pulled up to the contact address, a boutique called "Dash". It looked like a pretty ritzy place. I looked at the envelope and read the directions on the paperwork. It was to be signed by one Kim Kardashian, and no one else.

Gee, he's being direct in his orders to me.

I walked in to the shop and it was pretty quiet. A pretty young girl asked if she could help me.

"Oh, Hi, I'm from East Coast Image and I have some materials that need to be approved by the owner." I said.

"OK, hang on. Kim! There's somebody here for you!"

From the back of the store walked this vision, no, bombshell of a woman. It suddenly hit me exactly whom I was meeting with. And it was really her.

It was "the" Kim Kardashian alright.

She had on a dark pinstriped pantsuit that really accented her jet black hair and olive colored skin. Her hair wasn't tied back or anything, it was cascading around her shoulders. I think I might've even gasped somewhat when she walked out.

"Hi! Are you Chris' partner?" she asked sweetly.

"Yes, that's me." I replied.

"He told me you'd be coming," She said looking at her watch, one that looked almost diamond-like. "Wow you got up here fast."

"Beginners luck, I guess." I said with a shrug.

"Come on in the back, I've got all the stuff you need." And I followed her into the office area.

"I'm gonna close up Kim!" said the girl who met me as we headed into the back.

"OK, Kourtney. I'll see you at home later."

That's right! Her sisters are involved in this place too.

She sat down at a small desk and started looking over the papers and photos. They were for a new photo campaign Chris had started on when we were in London. He'd somehow met with her reps there and they'd been talking back and forth by email ever since. I hadn't concerned myself much with what he was working on. I suppose I should be, then I wouldn't be so exasperated at driving to Calabasas. The office was small, but neatly furnished with a leather loveseat and tables stacked with magazines and photos. A simple antique table served as a desk with only a laptop and a phone on it. Very simple, very efficient.

"So, how long have you been working with Chris?" she asked while reading the papers.

"Oh, uh, only a few months. But we've been friends for a long time."

"I met him awhile back, I think it was at some party Paris had." She replied.

"Hilton?" I asked

"Who else? She drives me nuts. Just promoting herself all the time." She said.

"Really?" I replied.

"Oh, don't get me started on her." She said raising her hand slightly, but still smiling. Then saying; "Nah, she's OK for the most part. She doesn't come up here all that much so it's not like I see her all the time."

"Oh, I get it. The less you see of someone, the better?" I offered.

"Right." she replied.

She was flipping through the photo sheets, then looked up at me.

"Have you seen any of these?"

"No, I only knew he was working on some project with you but nothing more." I said.

"OK, well I guess you should know. I'm starting a lingerie line here, probably only on the web site. Want to see the photos?" she asked with a sly smile.

"Uh, sure." I said

I went over to her desk and stood in front of it, looking at the photos upside down.

"No, no, come over here." She corrected.

I hesitated slightly.

"Oh come on, I don't bite. Unless you want me to." She said with another sly smile and a raised eyebrow.

So I went behind her desk and she showed me each photo.

The photos were, well, incredible! She had on a variety of satin nightgowns, camisoles, even a series of flannel pajama sets with necklines that really accented her curves on top. It was very hard for me not to stare down at the incredible chest that was before me. Not just in photo form, but for real. There were also outfits that must've been intended for role-playing that included a schoolgirl outfit of plaid skirt and grey sweater with a private school logo.

"What do you think?" she asked.

"This one is nice." I said pointing at the schoolgirl outfit. "But this one is a little more, uh, romantic I guess." Pointing to a satin nightgown.

Kim listened intently to my thoughts and I could tell she was watching me.

"I think it will be a big hit for you." I said with confidence.

"Great!" she said smiling.

She signed all of the papers where directed.

"OK, did Chris tell you what to pick out?" she asked

"Pick out?" I said, confused

"Right, oh he didn't tell you? OK, part of the deal with him was the employees could pick out stuff they wanted from the store. You can get something for your girlfriend for free." She explained.

"Oh, well, uh.." I stammered

"You don't have a girlfriend? Come on! Really?" she sounded stunned.

"Uh, sad but true I'm afraid."

It was true. Yes, good 'ol "Hollywood" had had his share of beauties but my schedule was such that a private life really hadn't presented itself to me. It's not like I hadn't been trying. But somehow I just never really embraced the swinging single life the way Chris did. Hell, he had a master's degree in that!

"Hmm, let me think." Kim said.

"Uh, I guess a gift card would be fine." I offered.

"Oh no, this isn't a Wal-Mart store. I've got an idea."

She gathered up all the papers and photos and slipped them back into the envelope I brought them in.

"I'll give you a first look at everything. And then you can tell me what you like."

"Oh, uh, Okay." I was confused at this moment. What did she mean by that?

She led me down a hallway to what seemed like a large elegant dressing room with mirrors on all sides. A couch and some chairs were in it too and several small cabinets.

"I'll be right back." She said and left me in the "roomful of mirrors". I kept thinking of the old Hendrix song;

"I used to live in a roomful of mirrors, all I could see was me..." I sang to myself.

At that moment, my cell phone rang, it was Chris.

"Hey, did you make it up there OK?" he asked

"Yeah, sweet ride pal!" I answered, clearly envious of his wheels.

"Did you get everything signed?"

"Right, I was just about to-" I started to say.

Kim returned wearing the grey schoolgirl outfit I'd seen the photo of.

"Uh, I'll call you back Chris." I stammered.

"Well?" she asked.

"Uh, congratulations to the lucky man." I answered hesitantly.

Kim slowly walked over to me and touched her finger to my nose.

"That would be you, 'Mr. Hollywood'" she said with a sexy twist.

"What?" I answered, stunned.

"I know all about you. Chris told me how you got your name, all your adventures together. You guys are quite a team." She continued.

"Wa-wa wait a minute Ms. Kardashian. I just work for Chris, he's a friend and all but I'm not sure if-if-if this is..." I continued, stammering every word.

"Is what you want?" she raised her eyebrows as she said that. "I know what you want." She said with an even sexier tone of voice, and an even sexier look in her eyes. As she said this, she wrapped her arms around me and we kissed. Her lips were very hot and her perfume was like heaven as it swirled around me.

"..And I'm going to give it to you." She whispered in my ear.

My arms were like rubber bands at this moment.

She kissed me again and I could feel her tongue work its way inside me, it felt so slick and good. My tongue impulsively merged with hers.

"Wow, that was nice." She said with a smile.

She gingerly placed my hands on her hips, but I was too nervous to move them.

"You wanna touch my ass don't you?" she said with a giggle.

"Um, well, uh.." I stammered

"Go ahead." She said

I felt it and it was definitely there all right.

"Feels nice, huh?" she said

"Um, I, uh.." I was stammering like never before, I was so embarrassed.

"Oh, I see. You'd rather have these.." she said as she cupped her beautiful tits. "Go ahead, then."

And she placed my hands gently on them. God, did they feel nice!

Her head and body swayed slowly as if she was enjoying my touch. Her eyes were slightly closed and she was giving me a smile too. Her lips were puckered slightly and a soft "Oooooh.." came from them.

Her hand moved down to the crotch of my jeans and began rubbing, there was an instantaneous reaction, like a light switch being turned on. Or a "love light" as the case may be.

She embraced me and whispered,

"That feels nice."

She looked down and found the zipper and slowly worked it down.

"Are you-are you sure this is OK?" I asked, sounding petrified.

"Sure it is, I told you I know all about you." She said calmly with a smile.

I could feel her hand working its way inside.

Her hand had found it its quarry.

"Oh, I think you're ready." She said with a giggle.

She kissed me deeply, her dark eyes were like a soft laser beam as they watched me.

"Just relax, honey. I'm gonna make you feel good."

Kim knelt down and I felt my dick come out from my pants.

"It looks nice," She said looking up at me.

She softly kissed the tip and slowly licked all around the head of my dick.

"You like that?" she asked with a smile.

I could only nod my approval.

She continued to lick around it, then slowly worked it into her mouth. I could see it slide into the mouth of this Hollywood starlet with seemingly no resistance. Then slowly slide out, with a tongue swirling around it. She continued to do this and I was still so nervous, but my dick had other ideas. It was becoming more and more of a dynamite stick, about to explode. Usually I could sense this and knew when to move on to other things, but when you're with someone like her, control seems lost. And I had none. I could only let myself go.

"Oh, no Kim...Oh god Kim.." I said quickly.

Then I felt an explosion in her awaiting mouth. I just knew this was a disaster. I felt utter humiliation and shame at what had just happened.

Or so I thought.

Kim showed no resistance. I heard an "Mmmm" come from her mouth, which was still filled by my dick, and now its climax. I saw a little bit of come dribble from the sides of her mouth. But otherwise, I'd unloaded in her and she'd taken it all. She recovered enough to look up and smile at me.

"Wow, that was something." She said.

"I'm so sorry, I feel so bad, I'm so sorry." I really felt utter humiliation at this moment and wanted to crawl into a hole and die.

Kim stood up and held me.

"Don't feel so bad, honey." She said reassuringly. "I seem to have that effect on guys." She said with a smile

She "seems to have that effect on guys"? Gee, I wonder why?

"I like this outfit because it reminds me of my school."

"That would make sense." I said, now regaining some bit of confidence.

"Every guy has this 'naughty schoolgirl' fantasy. I figured I'd design an outfit for that." Kim said as she showed it off. "Is this your fantasy?" she asked in a sexy voice.

"Uh, well, uh I don't know." So much for regaining my confidence.

"Well, this schoolgirl has been very bad, and needs to be punished." She said innocently.

"Y-y-y-yes..." I stammered

"So?" she said.

"W-w-w-what?" I stammered again.

"Punish me." She said in a slightly demanding voice.

"Punish you?" I asked.

"Come here...come on...you don't have to be scared of me." She said with a calm smile.

I went over to her and she took my hand and slapped it on her ass playfully.

"Get the idea?" she said.

"Oh, I see." I replied and slapped her ass a little more forcefully.

"I must be punished." She playfully said again.

I slapped her ass again.

"Good." She said.

"Sit over here" and she directed me to sit on one of the chairs against the wall.

Then Kim stood before me.

"Mr. Hollywood, I've been a bad girl. I'm sorry for what I did." She said with an apologetic and fearful tone.

"What did you do?" I replied.

"Whatever bad thing you said I did." She replied

This was starting to sound like a bad comedy sketch!

"Oh! THAT bad thing!" I now said.

She giggled, knowing I could see how silly this was getting. But also what she was implying I do. What she definitely wanted me to do.

"So I'm ready to accept my punishment." She said in that "I'm so sorry" tone.

"Yes, your punishment." I said with mock sternness.

"Yes, Mr. Hollywood, my punishment." She said again.

"Well, Kim, you've done some bad things around this school lately." I said trying not to laugh at how goofy this was getting. "And I have no choice but to punish you firmly."

"Yes, Mr. Hollywood." She said

I have to admit, this was the first time hearing that name from someone was actually fun. Usually I just rolled my eyes.

Not this time!

"Kim Kardashian, I must take you over my knee." I said sternly.

"OK." She said trying to sound tearful.

"Remover your panties, you must be punished." I said.

Jesus! Did I just say that?

Kim stood before me and slowly dropped her panties. They were of a silky red material. Her pussy looked as smooth as silk. Her pussy folds were hot pink. I got an instant hard-on right there.

I took her hand and had her bend over my lap. Here was that famous ass the world knew and it was in front of. It was big alright, but ultra soft. My fingers went in the crack of her ass and I could see her look over her shoulder with a lustful look.

My right hand came swiftly down and slapped her ass.

"OH!" she gasped.

SLAP!

"OH!"

SLAP! SLAP! SLAP!

"HUH-YES!" she cried.

SLAP! SLAP! SLAP!

SLAP!

"YES! DO IT!"

SLAP! SLAP! SLAP!

"YES!"

SLAP!

"OH YES!!" she cried out again.

Her dark skinned ass was getting red from my "discipline". I rubbed it softly now.

"I think you've learned your lesson Miss Kardashian." I said in that stern tone I'd been using.

"Yes, Mr. Hollywood." She replied.

Kim got up, sat on my lap and kissed me softly on the lips.

"That was fun." She said with a smile.

"First time I ever spanked someone." I said smiling.

"You do it well, did you like it?" she asked raising an eyebrow seductively and smiling.

"I think I did." I replied.

"Good." She said giving me a quick kiss. "Now, stay here, there's one more thing to do."

And she got off my lap and left the room.

"More?" I thought. How could she top what we just did?

Very easily, it seemed.

Kim reappeared a few minutes later in the white silk nightgown I'd seen earlier, she looked stunning. She leaned against the doorway in a very seductive manner and smiled.

"Whoa..." was all I could say.

"Like it?" she asked softly

"Yes, very much so." I replied in the same tone.

She reached for a light switch and dimmed the lights so the room was a soft red color. She walked over to me and we embraced again, her kisses were so soft.

"We've had our fun, and you said this was more romantic. So...now we can have the romance part." She said.

"I see what you mean." I said.

"Why don't you get out of those clothes." She said seductively as she kissed me again.

She took a step back and slowly let the spaghetti-type straps down, and the nightgown dropped to the floor.

Kim Kardashian was now totally naked in front of me.

My hands were trembling as I fumbled with the buttons on my denim shirt. Kim giggled a little, then came over and took my hand.

"Why don't you let me do this. Just relax." She said reassuringly with a smile.

My shirt was slowly removed and she rubbed her hands on my bare chest. She moved her hands down to my belt and began to loosen my khaki pants, letting them fall to the floor. I somehow stepped out of my moccasins and was now naked in front of her as we kissed deeply. I had somehow become comfortable being with this beauty.

"Let me see you." I said softly to her.

"Oooooh you're a mind reader too. I was thinking the exact same thing!" she said with a smile.

Kim took a step back and we looked at one another. She had stunning breasts, they were definitely large with pink areolas. Her dark hair gave her such an exotic look and that seemed to be the only hair on her. There was a small pussy with pink folds that seemed to beckon me. Kim was definitely focused on what was between my legs and how it was reacting to the situation before it. She smiled as she saw what she'd inspired in me. I held my hand out to her and she took it and we kissed again, before moving onto the couch. Kim lay down and draped a leg onto the floor. We were still kissing but I wanted to get at those tits of hers. They were so beautiful to hold, she smelled like a flowered mist and she tasted wonderful. I licked and sucked her tits and she was moaning and breathing hard. As much as I loved this, I knew there was more to her. I kissed my way down to her pussy, she was moaning even more the further down I got. I eagerly started to lick her, using my tongue as a miniature dick, this got her screaming.

"OH GOD!! OH GOD BABY!! YES!! OH MY GODDDD!!!" she screamed out.

I found her clit and tongued it very softly. She was still screaming out the whole time.

When I slowed down my pace, she gradually became quieter, her gasps and moans decreased. She then took a deep breath and slowly exhaled.

"Wow...baby you're good!" she said laughing.

I had put my finger inside her and twirled my finger around her nipple, then licked her pussy juices off it. She giggled at the feeling.

We kissed again, and she stood up.

"Let me get a Trojan for you." She went over to a cabinet and got one out. She tore off the wrapper and delicately placed it on my dick. Then she returned to the couch and spread her legs wide.

"Come on..." she said softly with a look of lust on her face.

I took a deep breath. I had to wonder, would I be all she expected?

I slowly pushed my dick into her pussy, it wrapped all around my dick. There was no resistance from her. Hr eyes closed just slightly, then she smiled even more.

"Oh...that feels sooo good...oh yes...oh yes...I love this..." she said, her voice trailing off as she let the waves of desire roll over her. I slowly began to fuck her, each stroke was met with a quiet "oh yes" from her. I was unconsciously doing her at a slow pace. For some reason, I didn't feel the need to do her fast, she seemed to enjoy a slower pace, so did I.

12