Adventures of Hollywood Jim Ch. 94

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Dakota Territory.
3.5k words
4.6
10.6k
11

Part 96 of the 101 part series

Updated 02/26/2024
Created 08/06/2008
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The perks of a business like mine still surprised me sometimes. I was accompanying Jackie Morrison and key members of her staff to New York City for a quarterly board meeting. I had been to a couple of these when I was with Artists Unlimited, but for low-level employees like me, they seemed more an excuse to steal cigars or bottles of booze out of the bosses' liquor cabinet than to discuss any big business, much of which had no impact on people like me. The Morrison Group seemed a different story, but in a good way. We were all flying on the company jet (naturally) and Jackie was deep in discussion with lawyers and assorted types. I wasn't sure what my role would be in all this, but hey, a free trip to the big apple isn't something you turn down, right?

"Jim, come over here, we need your input." Jackie said just as I'd refilled my drink and hoped to settle in for the rest of the trip "You've worked with Demi Lovato before, right?"

"Oh yes, she's a real sweetheart."

"They all are until it's time to negotiate contracts." She said without looking up from her paperwork "What we're working on is a pilot deal for her."

"A TV series for her, really?"

"It's only in the early stages. She did a guest spot on 'Blue Bloods' last year. The producers and the network liked her work and we want to work this into a series deal for her."

"So where do I come in?"

"While we're in New York, you'll be in Atlantic City. She's performing down there and we need you to schmooze with her."

"I think I can handle that."

"Oh, I know you can handle it." She replied with a look that showed that perhaps she knew all about my past with her. The others around her only snickered.

When the jet landed, Jackie and her crew changed to a helicopter which would fly them into Manhattan, while I was in a limo heading for Caesar's Palace Atlantic City. It was a bit of a thrill for me to pull up to the hotel and see her name and face on the huge billboard outside. In black and white she looked incredibly sultry wearing a low-cut white nightgown and lying on a brass bed with "DEMI" in giant gold letters above her.

"I know her." I said with a smile to myself as I looked at it.

"Oh...my...God!" Demi exclaimed when I walked into her dressing room after her show "So good to see you babe!" She gave me a generous hug and her body felt beautifully warm against mine, even with the terrycloth robe she had on. She was meeting certain VIP's and would soon be going out to meet fans in a backstage room. "So what're you doing here, anyway?" she said as she sat down at a makeup table.

"Official business, I hear you're looking to get a TV series."

"Yeah, might be time for me to get back on TV. It's still just a thought." She said as her brunette hair was touched up by a stylist. Demi quickly checked her hair and makeup one last time and nodded her approval to the stylist. Into the room entered 4 women, one of them a willowy blonde who looked familiar. Her near-porcelain skin tone made her look almost like a doll and her eyes were a delicate shade of hazel. She wore beautifully stylish black jeans and a red satin blouse topped with a black leather jacket that looked more designer than biker. Demi greeted all of them and then turned the blonde to me.

"Jim, this is a friend of mine, Dakota Fanning. We used to hang out on the Disney lot when we were kids." Which made them both giggle at the thought of days gone by.

"Hi, Jim. Good to meet you!" she said in a bubbly voice

"Jim's the best photographer I've ever worked with." Demi said with a sly look in my direction. I think her definition of "best photographer" meant more than just my prowess behind the camera.

"No kidding? I'll have to remember him next time I do a movie."

"Jim's with Morrison Group now, you know, that big outfit in L.A."

"Oh, yeah...I think my manager mentioned some call from them."

"Jim, do your job and get a photo of us!" Demi said as she handed me her cellphone and I quickly got them together and Demi flashed that million dollar smile of hers.

"Ah, yes. We all need to get those selfies, don't we ladies?" I said which made them all laugh. Demi chatted with Dakota and her friends for a bit and then we were escorted out to the meet and greet. The dozen or so fans gathered got a big surprise when Demi introduced Dakota to them, who were clearly star struck.

When the meet and greet was done with, Demi suggested we all go get dinner somewhere. But she wasn't in the mood for anything fancy.

"Oh! I know where we should go, there's this pizza place on the boardwalk that's got the best slices." Dakota suggested.

"Perfect! Let's go!" Demi said with that big smile she was famous for "It's on me, c'mon Jim! We need someone to document this."

"Oh boy! More selfies!" I said which only made the girls laugh even more.

We made for quite a sight. I was walking in between Demi and Dakota, who were quickly arm in arm with me as we strolled the boardwalk. It was a perfect night for strolling. And I gotta admit, I felt very cool with these two ladies. Dakota's friends were close by as was a hulking bodyguard for Demi. The slices place was a hole in the wall joint on the boardwalk and we all got slices of different flavors. We found 2 empty benches and I sat with Dakota while Demi was quickly chatting with her friends. Demi's eyes were on me and she seemed to like seeing me with Dakota.

"Do you come down to AC a lot?" I asked her.

"Oh, yeah! It's like a second home for me, especially on the weekends. What about you?"

"I've only been here maybe one other time. I've done Seaside Beach though, where they filmed 'Jersey Shore'."

"Really? What's that like?"

"Eh, probably like this" I said as I looked around "Not as many hotels though. Ever done Vegas?"

"Oh, my God! I sooo wanna go there. Y'know, now that I can drink."

"Ah, yes. That does change the equation doesn't it?"

"Hell, yeah!" she laughed. She took her drink and started to look at me closer while taking a sip through the straw. I was doing the same.

"Hey Jim!" Demi yelled before laughing "Get a photo of us!"

I took some candid photos of the group and they all looked like they were having fun. Dakota wanted a shot just with me and she held me close as the bodyguard snapped the photo on Dakota's phone. Demi's phone buzzed and she turned to take a quick call. Dakota's friends were checking their phones too.

"Hey, that was my road manager reminding me I've got an early flight so I need to get some sleep." Demi said to me "I hope you don't mind."

"Nah, that's fine with me."

"He can hang with us!" Dakota giggled.

"Oh, yeah! You'll be in good hands there!" Demi laughed before turning to me "I'll buy you dinner next time, how 'bout that?"

"You got a deal."

"Cool!" she said with that classic smile as she hugged me "See you soon, babe."

Demi left with her bodyguard, leaving me with Dakota and her friends. They seemed like a fun bunch and wanted to know all about people I'd met out west, it was almost like a "can you top this" of people we knew, but being a gentleman, I gave the edge to Dakota. Sure it was a little gossipy but I didn't mind.

"Hey, Jim. You ever been under the boardwalk?" she asked me.

"I don't know...it doesn't look like the safest place to be."

"C'mon, we'll just check it out for a minute." She said confidently "It doesn't look too dark."

"OK, let's go."

"I'll see you back at the hotel." She said to her friends as she took my hand and we trotted down to the beach. She casually removed her shoes and loved the feel of the sand between her toes. We approached the boardwalk pillars carefully but there seemed to be little to worry about, other than whatever trash was there, along with the feral cats whose job it was to control the rat population.

"Well, this certainly lives up to its reputation." I said "Jersey at its best."

"Yeah, so much for romance." She said as she stuck close to me.

"Oh, what did you have in mind?"

Dakota smiled at me.

"Uh, maybe we should go back to the hotel." I said.

"Good idea, Mister Hollywood."

"How'd you know about that?"

She gave me that same smile in return "Like Demi said, we're old friends. Friends tell each other things."

It was late when we arrived back at Caesar's. When we got to her room, she held me back and put her finger up to my mouth and said "Shhhh." She opened the door slightly "Wait here a sec." she said to me as we walked into the darkened suite. I stayed by the door and she went into an adjoining room where I could hear TV sound and Dakota's voice talking to what I assumed was one of the friends we'd been with on the boardwalk. Just then my phone buzzed with an incoming text message, it was from Jackie;

"Mission accomplished, Demi's TV pilot is a go. Good work, Mister Hollywood."

I was tempted to write back that all I did was have a slice of pizza with her, but

Dakota returned before I could.

"OK, we're cool. Let's go to my room." She said in a soft voice as she grabbed 2 bottles of water from the mini bar.

She led me into her room and dimmed the light a little before closing the door. She slowly removed her jacket and tossed it onto a nearby chair. Her room was casually messy. An open suitcase had numerous items strewn around it, like she had a hard time deciding what to wear this evening. I stood by the window and looked out at the nighttime lights of Atlantic City as she approached me from behind. She wrapped her arms around me and I turned around to see her.

"Hi." She said with a smile.

"Hi, blondie."

We both moved in close and kissed. She had a wonderfully soft perfume on and its scent made our kiss all the better.

"That felt nice." I said softly.

"Yeah...I like that." She said in the same tone, with a smile added.

We kissed again, stronger this time and my hands began to slowly caress her body. I could feel the denim of her jeans. They had that slightly rough feel of new Levi's not yet broken in by washing and wearing. Her embrace felt very loving.

"Would you like to lie on the bed?" she whispered.

"OK."

She removed her white Converse sneakers and I did the same. We lay on the large bed and kissed even more. Even though she was a lady in her twenties I felt like I was with a teenager. Our lips parted and her eyes seemed to give me the OK to go further. I carefully moved my hand to her breast and she breathed in a little.

"It's OK...yes...touch me there." She said softly. Her breast felt very soft through the material of her blouse "Sorry I don't have boobs like Demi."

"Why should that matter?"

"Um, I figured guys liked that." She said bashfully.

"Well...Demi's nice and all but everybody's special. That's what I always believed."

Dakota gave me a little smile "That's very sweet to say." She said as she gave me a little kiss. I returned with one of my own. I gently moved her onto her back and we kissed some more.

"Um...m-maybe we should be more comfortable?" she said in a shy voice.

"Yes, good idea." I said as we kissed again

"I'll be right back." She said as she got up off the bed and grabbed something from her suitcase and went into the bathroom and closed the door. I was unsure of what lay next. Yeah, I kinda knew, but still you never know what could happen. I got my answer when the door opened and Dakota stood before me in a lacy white satin camisole and matching shorts.

"What do you think?" she asked with a shy smile added.

"I think you look...beautiful." I said in a near-whisper.

"Thanks...um...I'm kinda nervous wearing it."

"Why?"

"I don't know...I just am." She said as she walked over to me and we embraced.

"Don't be. I think I should be the nervous one."

"Why?"

"Well, 'cause I'm a little overdressed."

"Maybe I should do something about that." She said as she began to remove my shirt. Once it was off, I got up from the bed and started to unsnap my jeans and slid them down. Dakota came over and sat up on her knees to kiss me again. Her hand went down and felt the growing hardness in my grey Calvins.

"Mmmm..."she said softly "Demi was right."

"What'd she tell you about me?"

"She told me enough." She said softly as she kissed me and led me back to the bed where we stretched out. My hands softly caressed her body. I gingerly reached for the thin lacy straps that cris-crossed the middle of her camisole and slowly undid them. The more I did, the more her breasts were exposed until I could reach inside and touch one. Her eyes closed and she let out a soft "ohhhh" as I began to caress it. I could feel her nipple get diamond-hard as my fingers touched it.

"Lemme take it off..." she whispered.

She brought it up and off her body leaving her topless in front of me. She looked even more doll-like this way and she gave me that shy smile as I took in the view. She started to cover herself up but I gently stopped her.

"No, no, you look beautiful." I said softly. Her face showed how she appreciated my reassuring words. She began to touch the bulge in my Calvins and giggled a little.

"C-can I take them off?" she asked.

I nodded.

Her soft hands pulled them down and my dick sprang out, she gasped a little as she saw it. She began to caress it, her fingers felt so good, especially while she kissed me. I nervously reached for the waistband on her red bikini panties and as I began to pull them down, she stopped me.

"No...let me do it..." she said softly as she slid them down. Her pussy was totally smooth which only added to the feeling I was with a teenager. We were both naked and I couldn't help but look at her nude body.

"We kinda look, uh, good don't we?" she said with a shy giggle.

I nodded and leaned in to kiss her again. Dakota led me back onto the bed and we now eagerly kissed and felt one another. I gently moved her onto her back and began to kiss down her neck until I got to her breasts and started to delicately lick her tiny nipples. She started to breathe rapidly and now little sounds of pleasure came from her.

"Ohhhhh...oh sweetie...oh yessss..." she sighed.

I moved down her very flat belly and felt her legs open the closer down I got. I looked back up at her, a look of bliss on her face. I softly kissed her pussy lips and she breathed in and let out a long, slow, sexy moan. But before I could go further, I felt her sit up a little.

"Hey, I wanna try something..." she said playfully as she sat up further "You ever done a 69?"

"I've heard of it, but never tried it."

"C'mon...let's do it." She said with a naughty smile on her face. She carefully swung her leg over me and carefully presented her beautifully smooth and pink pussy to me. I could feel her soft breaths on my dick as it slid into her mouth. My tongue began to gingerly lick her pussy. I could hear small moans coming from her as her tongue worked its magic. My hands caressed her ass and brought it down closer to me. She tasted so sweet the more I licked her pussy. I started to push into it with my tongue and heard a strong "OH!" from her as it penetrated her. Her moans were becoming stronger. She finally eased off my face and sat next to me, still breathing hard.

"Oh my god, Jim...I'm so ready now...c'mon I wanna do it."

I sat up and kissed her lips, she nodded to me. She was ready.

"Um, are you, uh...protected?" I hesitantly asked.

"Oh yes, yes I am. My Mom prepared me for that." She said softly. I don't know how or why, but I remembered her telling a story about little notes her Mom left her in suitcases when she was in Budapest for six months filming "The Alienist". So the idea that her Mom "prepared" her for this seemed fitting.

Dakota lay back on the bed and I slowly got on top of her. Even in the dim light of the room, her skin looked almost white. But her legs were wide open to me and I kissed her as my dick slid into her pussy. She gasped a little as it penetrated her but quickly held me close and I began to fuck her with slow strokes. I felt her legs grip tightly around the back of my legs and it made me fuck her harder. She began to moan in rhythm with each thrust into her, her eyes were just slightly closed and she seemed lost in the sensations. We instinctively pulled one another closer and it made me thrust even harder into her. Now her breathing grew more rapid, she was close now.

"Oh yesss...oh my god...ohhhhhh godddddd!!" she moaned.

I kept thrusting into her, my explosion building. She felt so good, so soft.

"Oh god...gonna...gonna cum...ohhhhhh!" she moaned.

I could hold back no more and exploded into her pussy as I collapsed onto her, breathing equally hard. When I raised my head slightly, her sweet smile told me how much pleasure she'd just felt and she gave me a soft kiss. I slowly rolled off her and she laid her head on my chest. After a few minutes for us to catch our breath, she looked up at me and showed me that giggly smile the world often saw in her movies.

"Wow!" she giggled "That was sooo worth waiting for."

"What do you mean?"

"Well, I broke up with my boyfriend before I went to Budapest and...well, I guess it had been awhile since I...y'know...did it."

"So I'm like, the rebound guy?"

She nodded.

"I feel so cheap now." I said with mock guilt in my voice and we both snickered at that as we lay in bed, our bodies intertwined, letting the silence of the room and the ocean waves outside relax us.

We were soon asleep.

I slowly awoke several hours later and my head told me it had been quite an evening, even without alcohol. Dakota had since turned over onto her side and was still sleeping. I never noticed before what a cute ass she had. My Luminox Navy SEAL watch showed it was close to 8 am. I carefully got up from the bed and made my way to the bathroom to wash my face, hoping the cold water would help. Once that was done, I softly came back to the bed, only to find Dakota was awake and checking her phone.

"Hey, morning!" she said cheerfully as she sat up, looking cute first thing in the morning.

"Hiya gorgeous."

"How'd you sleep?"

"Pretty good, my head says otherwise." I said as I got back into bed with her and we kissed.

"Yeah, I feel the same way, and we didn't have a drink of anything."

"Maybe they put something in those slices."

"C'mon...lemme get a picture of us."

"Like this?"

"Sure, no one else will see it, I promise." She said as she got her phone on selfie mode and raised it up so we were centered perfectly. In the resulting photo, she looked fine, and I looked like a mess. But she loved it.

I guess that was all that mattered.

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4 Comments
AnonymousAnonymous7 months ago

You ARE cheap! Your sentences don't end!!

AnonymousAnonymousover 4 years ago
Where In The World Is Hollywood Jim?

I miss your stories buddy. Where are you?

AnonymousAnonymousalmost 5 years ago
Where are you

I miss your stories so entertaining

AnonymousAnonymousalmost 6 years ago

I've always had fantasies about Dakota Fanning, especially when she was younger, so found that really hot and entertaining. Well done.

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