tagCelebrities & Fan FictionAdventures of Hollywood Jim Ch. 33

Adventures of Hollywood Jim Ch. 33


The ocean sounded like the beautiful soft breaths of a sleeping woman as it awakened me that morning. My eyes and ears told me I was still in Hawaii. And the previous night was still a little hazy in parts but the ending I remember quite well. I turned slightly and could see my naked companions were still here, still asleep, and still beautiful.

One was a redhead named Ashlee, and the other a blonde named Jessica.

They had a last name in common, Simpson.

How they got here was quite a story, I probably should back up and tell it all from the beginning. Perhaps it'll make more sense.

The previous morning I'd awakened alone. Kim and I had gone back to her place for dinner, she had a family commitment that she was nice enough to invite me to. Waking up here alone didn't make me feel used; her devotion to her family was something that didn't make the gossip rags. And it was something I fully respected. I was still getting acclimated to this lifestyle that was suddenly mine, if only for a week. I sat out on the deck and watching the ocean, unable (or unwilling) to move, the endless waves gave me a sense of tranquility I'd never experienced. It was my cell's ringing that brought me back to reality.

"Aloha, pal!" it was Chuck calling from LA. "Great place, huh?"

"You said it, man." I said lazily.

He laughed on the other end.

"Well, it gets a little better, remember Marty O'Bryan?" he said.

"Um, yeah, wasn't he the guy who produced Tigress' albums?" I replied.

"And he also developed the Soundscape software." Chuck continued.

"No kidding, He did that?" I said, surprised.

"You bet, look up the beach, do you see a huge house down there?"

"Yeah, I see it." I said looking at an enormous stone and wood home about a mile down the beach.

"That's his place." Chuck said.

"Whoa!" I was stunned.

"Yeah, whoa is right." Chuck said. "Anyway, go down there tonight, Marty heard you were in town, he'd like to see you."

"Me?" I said, still stunned.

"Right. Head over there tonight, a guy like him is someone you should know. You'll have fun." Chuck said.

"Well, uh, okay I'll be there." I said hesitantly.

"Aloha, pal." And he hung up.

Marty O'Bryan was indeed the producer of Tigress' albums and a recording company software mogul. He'd developed the Soundscape system that became the industry standard for recording. He luckily patented the technology before someone like Microsoft could steal it from him. He now received a generous lifetime royalty from them and built an enormous Hawaiian estate that was the envy of every other millionaire worldwide. And this place seemed like an endless party. Marty and I had met a few times when we worked with Tigress, but I never got to know him that well. As evening came, I walked up the beach, unsure what I'd find when I reached this Hawaiian version of Citizen Kane's "Xanadu" house. As I approached the home, I could hear music blasting and heard Marty's voice from the second floor balcony.

"Hey! Jimbo! You made it!" he called.

"Well, I couldn't turn down an invitation from the king of the islands." I said.

Marty laughed and showed me inside.

His house was a palace inside, and he had many guests roaming in and out, and many bikini-clad beauties.

"I'll tell you Jim, it's good to see a familiar face here. I know your partner's gonna be in next week, right?"

"Right, he'll be here Friday night."

"Good, Chris' always around but I never see that much of you."

"Well, I'm glad you invited me." I said.

"Get yourself a drink, I'll see you on the beach." Marty said as he followed a nubile beauty outside.

I wandered around checking out the place. I recognized a few people from the Tigress staff. There was a multitude of food and drink options. I thought I saw Kendra Wilkinson from Playboy heading out to the brightly lit volleyball court, she shot me an "I know you from somewhere" look that made me smile in return. Nah, it's probably someone else she was looking at, I thought. I found the bar and got a bottle of Corona. The beach was calling my name though. As I headed out I bumped into a laughing blonde who was heading in the same direction.

"Hey! I remember you!" she said happily.

I was trying to adjust my eyes in the semi-dim surroundings.

"Remember that Mercedes you got to drive?" she said with a smile.

It was Jessica Simpson. She looked great in a Hawaiian print dress and flip-flops.

"Oh, wow! Yes, of course I remember you." I said suddenly

"What are you doing out here? You know Marty?" she asked.

"Um, somewhat, he works with Tigress and..." I started.

"Oh! The tour, that's it!" she said excitedly. "You look great!"

"Well, so do you. I guess Hawaii will do that to a person." I was just surprised she was here and remembered me.

"Oh, you bet! Hey, I know somebody you'll want to meet. I'll be right back." And she disappeared into the party crowd. I went out onto the deck and joined the people who were watching the sun sink into the ocean. Kendra soon reappeared.

She was somewhat shorter than I imagined, but very blonde and busty, with her hair tied in a tight ponytail, and wearing a form-fitting tank top and shorts.

"Hey, you look familiar, have you ever been to the Playboy Mansion?" she asked.

"Uh, no, only in my dreams I'm afraid." I said with a nervous laugh. "I'm Jim."

"Kendra." She was about to say something else when she was called back to her game.

Just then, Jessica reappeared with someone in tow.

"Ash, this is Jim. Remember I told you how I met him in Dallas at the concert?" She said.

"Hi, I'm Ashlee Simpson." She said in a bubbly voice.

"Yes, hi" I replied. "I remember watching your TV show."

Ashlee was as tall as her big sister, but with straight, bright red hair. She wore a flowery print Hawaiian shirt and white pants.

"Jess told me how you helped her out that night." She said with a smile.

"Oh, well, I was just being a nice guy." I said modestly with a shrug.

"Guys like you are tough to find." She continued.

Jessica was laughing.

"Well, uh, we're out there." I said with a nervous smile of my own. "Can I get you two a drink?"

They looked at one another, smiling.

"Whatever you're having is fine." Jessica said. Ashlee nodded in response.

"Be right back." I said as I headed back to the bar.

Marty was holding court by the bar when I walked up.

"Hey, Jimbo! I saw you and Kendra out there, you make a good couple." He said with a know-it-all smile.

"Well, if saying hello makes us a couple then maybe you're right." I replied with a laugh of my own.

Marty handed me 2 more Coronas.

"How'd you know what I was getting?" I asked.

Marty put his arm around me.

"Let me tell you something Jimbo, you have fun out there. You're a hard worker and a good worker. You deserve some fun, my friend." He said in a fatherly way. "Good things are gonna be happening with you, I know it."

"Well, thanks." I replied, somewhat confused by his "advice".

It was odd that he not only knew what I was getting, but how many. As if he knew who I was with.

I walked back to the outside deck and the girls were there watching the volleyball game.

"Two Coronas, for two lovely ladies." I said. Then immediately wondered why I said something so lame and corny.

"Thanks, babe." Ashlee said.

"Cheers, Jim." Jessica said as we all clinked our beer bottles together.

"Let's get a table over there." Ashlee said.

We found an empty table off the side of the vast deck area.

Jessica and Ashlee looked incredibly hot together. I was fumbling with my words trying to say anything.

"So Jess told me you met in Dallas, right?" Ashlee said.

"Oh yeah, I guess Tony didn't feel like hanging around so I had to drive her home." I said.

"Oh man, he can be the biggest asshole sometimes." Jessica said before covering her mouth again, embarrassed at her language. Ashlee only laughed.

"Jim's a good guy, he's heard it all before, right Jim?" Ashlee said.

"Oh, I didn't hear a thing." I said with a look of innocence on my face that only made the girls laugh harder.

"So, if you don't mind my asking, uh, where's Pete?" I asked referring to Ashlee's husband Pete Wentz.

"He's on tour in Europe." Ashlee said. "And the baby's at home with the grandparents."

"Oh, I see." I said as I took another swig of beer.

"That's why we came out here, it's a good thing we ran into you, you know." Jessica said.

"It is?" I said, confused once again.

"Right, you see...Pete's away now...and Ashlee's been, well...lonely. You know, with the baby and all." Jessica said.

"Uh...right." I said, I could feel my stammer coming on.

"And since she knows about you and me...well...she was, well, I was, we were wondering..." Jessica's voice trailed off, and Ashlee's head was resting on her hand and she smiled at me.

"I think he knows, right Jim?" Ashlee said calmly.

"I-I-I-I think I do." I stammered out.

The girls looked at one another and smiled.

"How far away is your place?" Jessica said.

"It's, uh, up the..." my voice trailed off and I could only point (with a very shaky hand) to where the house was.

"Let's go up there, just to check it out, right, Jim?" Ashlee said.

I could only nod in agreement.

"I'll go get some more beers." Ashlee said.

We all stood up and Ashlee went inside to the bar.

Jessica stood close to me and held my shaking hand.

"You're so nervous, why?" she asked.

"Well...it's not every day some...something like this goes on and I-I-I..."

"Hey, it's just us. You're gonna be fine babe." Jessica said calmly, with a small kiss on my cheek.

Ashlee reappeared with an entire 6 pack of Coronas, which made Jessica laugh even more.

"Oh, sure Ash, let's get him drunk too!" she laughed. "Come on, let's go."

I felt bad not saying goodbye to Marty, I caught Kendra looking at me with the Simpson girls. I think she was smiling. Maybe she was envious or maybe she knew what was going on.

Jessica led us out to her silver BMW X5 parked with other vehicles around the vast front of the house. I went for the front passenger side door, but Jessica corrected me;

"No, no, you sit in the back Jim."

I nervously climbed into the back and Ashlee was beside me, with a look of mischief as we pulled away from Marty's place. She slowly slid over to my side and took my hand in hers.

"Hi." She said to me.

"Uh, hi, back." I replied, still nervous as hell at what was going on.

I could see Jessica's reflection in the rear view mirror and she was smiling. Ashlee caressed my hand and softly kissed my cheek. Her hand now drifted to the crotch of my cargo shorts and I could feel myself "coming alive" as it were. I tried to think what I should do next, but Ashlee was in control of things. Jessica looked over at us.

"You okay, babe?" she said with a smile.

"Uh, I-I-I guess so." I replied nervously.

"He's gonna be fine..." Ashlee said very seductively as she began to kiss my neck.

Jessica squealed with laughter at my predicament and Ashlee's answer.

"How much further, hon?" she asked between laughs.

"Uh, turn in...in here." I stammered.

Ashlee's hand was inside my pants now and I could feel it moving around, making me shudder. She turned my head slowly and kissed me deeply as Jessica pulled the BMW into the driveway.

"God, Ash! Are you gonna do him here?" she said.

"I wish I could! He's nice!" she said with a big smile.

"I told you he was!" Jessica replied.

Was this me they were talking about? The "geek-a-zoid" from Connecticut? Or was it the guy known to some as "Hollywood Jim"? Something just wasn't right about this whole scene. It was all too dreamlike right now.

"Uh...let's...l-l-let's go inside." I finally said as I freed myself from Ashlee's hot lips. We got out of the BMW, Ashlee held me close as Jessica trotted around the other side and both girls were on my arms, and smiling.

"This is gonna be fun." Jessica said with her mega-watt smile.

"Yeah, baby." said Ashlee with an equally large smile at me.

I hesitatingly unlocked the front door of the house, wondering if I'd be attacked the instant we stepped inside. Ashlee held me close as Jessica looked around.

"Wow! Cool place Jim!" she said, her voice echoing of the high ceilings.

"Uh, let me put the beers away." I said as I headed to the kitchen, Ashlee stayed close behind me. Jessica soon followed. They each grabbed a beer.

"Where's the bedroom honey?" Ashlee asked with a sly smile.

"Um...up...up...upstairs." I stammered.

"Let's see that." Jessica said as she took a swig of Corona.

I took them upstairs to a sparsely furnished room, all in white with mahogany colored hardwood floors and a gently turning ceiling fan. A huge antique sleigh bed was close to the windows. Ashlee and Jessica were both holding onto me again.

"This is nice, very tropical, the breeze feels so good." Ashlee said as she took a deep breath of the ocean air. Jessica lay atop the bed very seductively. Ashlee wrapped herself around me and kissed me deeply, her tongue dancing with mine.

"Are you...you sure this is-is-is okay?" I said.

"Sure it is." Jessica said. "Ash, he's all yours."

"Thank you." She said quietly before turning and kissing me again. I was completely blindsided what to do now. Her lips felt so soft on mine. She stepped back slightly and smiled. She looked at Jessica who responded with a look of admiration on her face. Ashlee started to unbutton her shirt.

"Oh, I can't wait." She said as the shirt fell off and her tits were exposed. They were perfectly shaped with small nipples.

"Get those clothes off, Jim." I heard Jessica say, she was still lying on the bed watching us.

"Well, now or never." I thought.

I pulled my polo shirt over my head, and turned just in time to see Ashlee pull her panties down, exposing a totally smooth pussy.

Ashlee gasped slightly when she saw me naked.

I was fully erect now and she smiled at the sight of it.

"Oh, that looks nice!" she said.

"I told you!" Jessica said.

Ashlee looked beautiful naked. And she seemed to enjoy the feeling. She walked over to me and we kissed deeply. I gingerly felt her tits and she moaned as I touched the nipples. My hands went to her ass and it was just as soft and toned as the rest of her. I could hear a breathless sound of joy as I felt her.

"Oh yes...so good." She said softly.

I looked over at Jessica who watched all this with a smile.

Ashlee's hand went down to my dick and began to caress it.

"Oh you've got a nice dick, baby. It's beautiful."

"So are you." I impulsively said.

She chuckled at my response.

"What do you think, sis?" Jessica said.

"I think he's very hot." She said flirtatiously as she looked back at me and giggled.

"OK, my turn." Jessica said as she hopped off the bed.

Ashlee slowly led me over to it and we lay down. Our tongues, lips, and hands were touching one another all over.

"Lay back, Jim." Ashlee said.

Ashlee slowly kissed her way down my chest and held my dick in her hands.

"Beautiful." She said as she took it into her mouth. I felt my head go backwards as the feeling hit me.

It got better.

Jessica stood at the foot of the bed and began to untie the straps of her dress letting it fall to the floor. She was totally naked underneath, and her pussy was shaved clean too.

"What do you think baby?" she said very seductively.

Ashlee's oral work left me speechless and I could only nod my head as Jessica walked over to the bed and stood beside me, her beautiful pussy just inches away from me, and her equally beautiful tits above me.

Ashlee came off my dick and smiled at the sight of her naked sister. She knew it turned me on.

"You like her, huh?" she said.

"W-what?" I asked.

"She turns you on, I can tell." She replied.

"How can you tell?"

"Well...your dick just got harder!" she giggled. Jessica laughed too.

"Yeah, I know what he likes Ash, slide over."

Jessica joined us on the bed, giving me a deep kiss.

"Go on, take 'em hon." She said seductively as she offered her tits to my waiting lips and mouth.

Ashlee continued to work on my dick, swirling her tongue around the head. Jessica stroked my head, gently cooing in pleasure.

"Oh...so nice...so nice baby." She said softly.

She pulled away and kissed me deeply, looking into my eyes.

"This is so hot..." she said breathlessly. "I've never felt like this ever."


I had a sensuous buxom blonde and an equally buxom redhead in my bed, in Hawaii. Could this get any better?

Yes, indeed. It could.

Jessica swung her legs over my head and lowered her gorgeous pussy to my face. She was soaking wet and tasted lovely. Her voice was a mixture of "oh's" and "yes'". Ashlee was still working on my dick but now made her move. Jessica leaned back slightly as Ashlee came up from behind her and gently cupped her tits and kissed her neck.

"Let's switch." Ashlee said "I want him now."

Ashlee and Jessica traded places, Jessica began to suck my dick while Ashlee and I kissed deeply. She offered her nice tits to my mouth and I eagerly licked and sucked them as we watched her sister work on my dick, her blonde hair made it even sexier.

"That looks so hot!" Ashlee whispered to me.

I was too lost in the moment to reply.

Ashlee now swung her legs over my face and I now had her pussy in front of my tongue.

Ashlee was more vocal than Jessica as I licked her.

"Oh yeah baby! Uh-huh...oh god eat my pussy...oh yeah!" she cried out.

Before I knew it, I exploded into Jessica's mouth. She swallowed some, then jerked the rest out of me.

Jessica came off my dick and kissed me softly.

"That was so cool, Jim." Jessica said with a smile.

"Mmmm...I can't wait for round 2." Ashlee said, somewhat out of breath.

"Round two?" I thought to myself.

Jessica lay between us. I couldn't help but lean over and kiss her gorgeous tits. She giggled, especially when Ashlee leaned over and did the same. I eagerly went back and sucked on her nipples, Ashlee did the same and Jessica's little giggles turned into moans of pleasure knowing how she was being pleasured. My hand went down between her legs and her pussy was wet again. She moaned quite erotically at the pleasure we were both giving her.

"Baby...I want you so bad." Jessica said.

"Me too." said Ashlee.

"Oh, do her first...I wanna watch." Jessica said as she sat up on her knees.

"Oh my god yes! I wanna fuck so bad now!" Ashlee said.

Ashlee's eyes widened at the thought of being watched like this. I sat up too and Jessica held my dick and softly stroked it. I could feel myself getting hard again. Ashlee watched eagerly and spread her legs wide, her smooth little pussy looked so inviting.

"Mmmm...so nice." Jessica said softly as she stroked me and I grew in size. Ashlee rubbed her pussy in anticipation.

"She's ready now." Jessica said with a smile.

I slid inside Ashlee's pussy and she gasped as I did. She felt just as hot as Jessica, who sat close to her sister and rubbed her own pussy.

Ashlee's eyes were slightly closed and soft "oh's" came from her mouth as I fucked her. Jessica watched intently, her own pussy looked just as inviting, God, I hoped I'd fuck her too!

"Oh fuck!" Ashlee yelled out.

"Doesn't he feel good Ash, huh...feel good fucking you?" Jessica said while rubbing her pussy.

"Oh fuck yeah!" she screamed.

"Jim...fuck her ass!" Jessica called out.

Ashlee and I changed positions. Her ass was up in the air and I immediately shoved my dick back into her pussy.

"Oh god, yeah!" Ashlee cried out. "Oh, god yes!" she screamed.

Jessica moved over to me and was on her knees next to me as I rammed into Ashlee. I kissed her and then fingered her pussy, making her moan in delight as we kissed.

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