tagCelebrities & Fan FictionAdventures of Hollywood Jim Ch. 09

Adventures of Hollywood Jim Ch. 09


As I'd said before, leaving Hilary the way I did that morning in London, after the night that was so special to her, broke my heart. We'd spent a passionate night together and she'd fallen asleep in my arms. Then my phone jolted me back to reality, reminding me I had a train to catch. Our work with Tigress was calling. I had no choice but to hastily scribble out an apologetic note as I dashed out the door.

Once I made it down to the hotel lobby, I saw Chris there casually reading a newspaper.

"OK, let's go." I said breathlessly

"Whoa, hang on pal! We've got time." Chris said trying to calm me down.

"What do you mean?" I asked.

"Well, we've got new travel arrangements." He calmly explained


"Uh, yeah, We'll be riding up there on their tour bus." Chris said.

"I dashed...down here.. for nothing?" I said, exasperated and still out of breath.

"Well no, we've got time for breakfast. Come on, I'm buying."

Chris had arranged for us to ride up to Scotland on Tigress' bus. The idea was we'd get more shots for their website. Looking back, I suppose it was a good idea. We had a filling breakfast and then hit the road. In all my experiences with Tigress, I'd never really gotten to know the girls that well. Chris pretty much had that nailed down. I had said that they were all giggles and jiggles. The girls were very flirtatious as you can imagine and I kept my cool all the way there.

Once we settled in for the long ride, I started checking all my gear. In my camera bag, I discovered one of my cameras was still on, and the battery was practically dead.

"Oh, wonderful!" I muttered to myself.

I removed the memory card and slid it into my laptop to transfer images, like I'd done millions of times before. Even if the card was empty, it was still part of my job to check that we had every shot where it should be. For some reason, there were 3 shots of my shoes at the beginning.

Then things got very interesting.

A photo of Hilary Duff in a black camisole combo popped up.

Then another with her lying seductively on a bed, a look of desire in her eyes.

I suddenly realized where this camera had been!

I was gripped with a sense of ultimate paranoia that I tried to hide as Chris was goofing around with the girls and their crew.

"Hey, 'Hollywood'! Remember the girl you smuggled out in your car?"

"What? Oh, yeah, of course I remember. Somebody named Hilton, I think."

I was trying to figure out a way to keep the discovery of my Hilary photos secret. There were an infinite number of reasons why. The press in England would be all over me if word of these got out. The American press would brand me as some sort of degenerate. Not to mention whatever trust she had in me would be gone in an instant. As well as her career.

"Yeah! Tell 'em how you did it, man!" Chris said trying to yank me into the conversation.

"Uh, wait a sec." I said.

All the while I was furiously making a folder within another folder to store the secret photos.

"Come on, man! Get away from that laptop for a second!"

I had finished just as Chris grabbed the laptop away from me and shut it off.

"Now, tell everybody about the smuggling you did for me." Chris insisted.

I recounted the story of smuggling out Paris Hilton early on in my photo career among other tales.

Chris was his usual goofy self. And I was placed in the role of straight man, as usual.

The next 2 days would be another whirlwind for the girls and us. It was an interview here, personal appearance there. And photos snapped everywhere.

Once we got to our hotel, we were both ready to drop. I took a long hot shower and Chris hit one of the nearby pubs, with a promise from me I'd join him later. It was only fair. How often can you say you "had a pint in Glasgow"?

But before then I really wanted to review all those secret photos. They were certainly provocative, and I had taken them! Hilary was stretched out on the bed, wearing the latest from Victoria's Secret and lustfully staring back at me in each one. She did a sexy "over the shoulder" look in one that implied she was topless. And she was leaning forward in another, giving the camera a great view of her tits. I sat back and stared longingly at them. It made me wonder what I should do with them. If I sold them to a tabloid, I'd have sold out a friend. And more than likely destroyed whatever credibility we'd both built up. The mere thought of that was out of the question. I knew that Hilary should have some say in what happened to these. But how to contact her was the big question. Even if I did somehow reconnect with her, how do I tell her about these? Did she even remember taking them?

For now the photos were buried on my laptop. I stashed the memory card in an old candy tin. I decided to hold off on any action until we got back home. I felt like I was smuggling a kilo of drugs with all the security precautions I was taking.

But then I realized that I was probably worrying myself over nothing. So long as the photos never left the folder on my laptop, or the candy tin, (or my big mouth, for that matter) they were safe. And when we got home, I transferred them to a flash drive and erased the laptop file. Her secret was safe with me. I fully intended to bury the flash drive away at my place somewhere. But being the paranoid type, I made a copy until I knew for certain where to store the original. Or in case I met up with Hilary again. Option two came sooner than I expected.

A week later I was tanking up the old Accord. And amazed at how she still held together. I still wondered what all those paparazzi guys would think if they'd seen Paris gliding away in my 'ol girl instead of the chic Benz she usually used.

"Jim?" I heard a voice say

I turned and saw a cute little blonde thing in a Rolling Stones shirt, jeans and vintage Converse sneakers poking her head around a gas pump.

"Yes?" I said uncertain if I'd heard my name.

"It's me!" The girl said holding her arms out.

It was Hilary.

"Hey! How are you darlin'?" I said excitedly as I recognized her.

"I'm great! I haven't seen you since London." She replied.

"Oh yes, I remember that night." I said cautiously.

"Me, too." She said with a smile.

"I got back a couple of days ago, um, I wanted to send you that photo you really liked but I didn't know how to contact you."

I was trying to discreetly let her know that there was a lot more than just that black and white photo she loved in my possession. I mean, you just don't blurt out 'Hey I got a great shot of your tits baby!' to someone like her.

"Oh yeah, right. I did like that shot." She said

"I've got it with me in my bag." I said matter of factly.

"Uh, can you come up to my house? I'm on my way home now." She replied in the same way.

"Oh, Sure. Where do you live?" I replied.

"Just up the road, follow me." She said.

And we were off.

Hilary's home was a ranch-style house in a gated community. I followed her black Mercedes-Benz into the driveway. We made for quite a contrast, this gleaming supercar next to my ratty old Honda. Her home had a real California feel to it. The rooms were large and comfortable. The windows looked out on a large backyard with a pool and patio area. On the walls were various photos, gold records, as well as a surfboard she won at the Teen Choice Awards.

Like I said, very California.

"Man, great house." I said with awe "Are you still here with your sister?"

"No, she got her own place, finally!" she said with a laugh from the kitchen.

She brought out 2 bottles of water for us.

"So, you have that photo from London?" she now asked.

"Oh, yes. I, uh, have the others too." I replied with hesitation.

"The others." She said, sounding confused.

"Yes, um, geez how do I put this." Now I was in the hot seat trying to be discreet about this.

There was an awkward silence between us at that moment.

"How much?" she asked firmly in a voice that surprised me.

"What?" I asked, stunned by her tone.

"You have the photos from London. You want to sell them to somebody. I don't want them to get out. How much?" She demanded in a voice that got scarier by the second.

"Nothing." I said, now petrified.

"Nothing? Oh, come on! I'm not stupid!" She yelled.

I held up my hands now.

"Please, hear me out on this." I said calmly

"Talk." She replied, still with an edge in her voice.

I took a deep breath, a big sip of water, and began my "defense" as it were.

"OK, yes I took those pictures. Yes, I have them with me. But no, I don't want to sell them to someone else. Or show them to anyone besides yourself. And I believe you should have final say on them. You said it was a special night for you. It was special for me too. That night was just as you imagined it would be. I don't want to be the one to ruin that memory. And I feel bad I left you like I did. I don't even remember what that note I left said. Please, here's the flash drive, do what you want."

And I tossed the drive onto a table.

She sat there with a stern look on her face that softened as her eyes went from the drive to my face and back again..

"All the photos are there?" she asked.

"Yes, all of them." I replied

"OK, can I see them?" she now asked.

"Sure, where's your computer?" I replied

"In here." And she led me to a smaller room that served as her office, as it were.

I plugged in the drive and she clicked through each one, looking intently at them.

In a calmer tone she said;

"I still like this one the best." It was the black and white shadow photo of her I took by accident.

"Me, too." I said calmly.

"The others are pretty hot aren't they?" she said looking up at me.

"Uh, yes they are." I replied.

She did a quick copy and paste of the photo to her computer and handed the flash drive back to me.

"You can keep them. I think you deserve something to remember me by. I trust you." She said in a soft, but firm, voice as she looked directly at me.

"I won't let you down." I said just as firmly.

Hilary leaned back in her chair, thinking about what she'd just seen.

"It's so strange seeing me like that. I've never liked the way I look." She said.

"Don't put yourself down, I always thought you were-" I replied.

"Cute? Wholesome?" she said with a touch of aggravation in her voice.

"No, pretty." I said.

"Yeah, right." She said as she got up from the desk and we went back into the living room.

"I really believe that." I said, wondering if I sounded like a guy in a bad singles bar.

"OK, How sexy do you think I am?" she asked sarcastically.

I thought out my answer carefully.

"Enough to fuck me right here, right now?" she said with her arms crossed.

"You bet." I said with my own demanding tone.

We stared at each other for a long time, wondering if we just said we thought we'd said. Then we both giggled.

"Did I just say that?" Hilary said, covering her mouth and clearly shocked.

"I think you did!" I said laughing.

"Oh my god!" she laughed.

We still looked at each other, unsure what to do next.

I decided to make the first move. I walked up to her, and she to me. We slowly embraced and kissed one another. Then kissed some more. All the memories I had of London came back to me.

"Just like I remembered." Hilary said softly, almost tearfully.

I smiled and kissed her nose as she closed her eyes.

"Come on.." she said as she led me to her bedroom.

Her bedroom had a real "girly-girl" feel to it. There was a large king size brass bed with a lacy white veil around the top that looked like curtains and a matching white bedspread and soft chairs throughout. Several stuffed animals gave it that extra touch as well.

She removed her shoes and I did the same. We embraced again, I kissed her soft lips and heard a soft "Oh" come from them as I withdrew.

Hilary looked up at me with an uncertain look on her face.

"Are you OK?" I asked.

"Yes, I'm just a little nervous in these situations." She replied.

"It's OK, I am too." I said

She smiled at me. Then she bit her lip and quickly took off her shirt, revealing a silky white bra that lifted her tits up just enough. Then she quickly unbuttoned her jeans, and they revealed matching panties.

"I didn't get to show you these in London." She said with a smile.

She was about to remove these when I stopped her saying;

"Could I just, uh, look at you this way?" I asked with hesitation.

"Oh yes, I was hoping you'd say that." She replied.

Hilary proceeded to strut around the room, like a stripper would. She did a lot of slow bump and grind moves. Even without music, this was really hot!

"Whaddaya think baby?" she said in a sexy voice.

"I think I should've brought some extra singles to tip you with!" I said with a laugh.

She laughed too, then walked back over, embraced me, and whispered in my ear;

"Take your clothes off, I want to fuck you."

There's that moment in a person's life when time just stands still. Or in my case, when the ears hear something, but the brain thinks it heard otherwise.

Hilary looked at me with a beaming smile that told me I'd heard right.

"Look at this." She said pointing to her panties.

I did and she pulled them down slightly revealing she'd had a bikini wax and was totally clean down there.

"Come on baby!" she said

I took off my shirt as Hilary unbuckled my pants and took them and my underwear down at the same time. Then she quickly removed her underwear and we were naked in front of one another.

She led me to the bed and we lay down, kissing and feeling one another. Her skin felt so smooth.

"What is that you're wearing, it smells incredible." I asked

"It's my perfume, my own brand." She said as we kissed.

"What's it called?" I asked

"With love, by Hilary Duff." She replied with a smile.

"Well, I love it." I said.

She giggled in response.

It felt so good, so illicit to be with her like this. Her kisses were so soft and passionate. She felt incredibly soft and delicate, just like before. She was caressing my dick slowly, getting "the feel" of it.

"I loved what we did in London." She said looking at me. "It was sooo sexy." She said with a big smile.

"I loved it too." I said

Hilary moved down and started to lick my dick like a giant ice cream cone. She smiled at me in a mischievous way. Then she let her lips cover the head and I could feel her tongue swirling around it. Her mouth was then filled by my manhood as it disappeared into her. This was different than last time, when she was uncertain of her abilities. How people can change in such a short time.

"Oh, yeah! That feels good!" I said.

"I guess I'm better now, huh?" she replied.

"Uh-huh. Did you take lessons or something?" I said jokingly.

She giggled again.

"Do I get an "A"?" she asked with a big smile.

"Oh, yes." I was lost in the moment now.

She came off my dick and sat next to me, her tits just inches from my face. I sat up slightly and kissed her cute little nipples. She gasped a little but moved down closer to me so I could get at them better. I caressed the other with my free hand. I could see her hand was down on her pussy.

"Baby, I want to show you something." she whispered.

Hilary sat up and reached for one of her stuffed animals, a large pink teddy bear. There seemed to be a little pocket in its back and from it emerged a small vibrator.

"What is that?" I said stunned.

"A little something I bought when I returned from London." She said with a big smile.

It was pink, looked like a rocket, and about five inches long. She turned it on and it made a soft humming sound. She placed it on her nipples and almost immediately started to breathe heavily. I resumed kissing and caressing the other one, which only increased her breaths.

"I want to do something." She said

She had me sit up and open my legs. She then got between them with her back to me and I could see we were now reflected in the mirror over her dresser.

"How do we look?" she asked me.

"Sexy." I said, getting another big smile from her.

She then turned the vibrator back on and moved it down between her legs, rubbing it up and down. Her chest heaved upwards and she was now moaning uncontrollably.

"You..can..watch me." she said in between moans.

My hands resumed their place on her tits. And I kissed her cheek and neck too.

"Oh god that's it!!" she screamed out.

The vibrator buzzed as she worked it all around her pussy. I was watching on the mirror as it seemed to move on its own with no assistance. My dick was super hard and it was pressing against her ass, wanting to go in. She was gasping and screaming nonstop. Then with a guttural "UH!" her body rose up and she collapsed in my arms. Her body went limp.

"Oh my god, just give me a minute." She whispered.

She slowly removed herself from me and rolled over to the nightstand, pulling out that small silver box I saw in London.

She unsealed a Trojan and placed it on my dick.

"I wanna fuck really good this time." She said with a sexy smile.

"I hope I can deliver." I said, now I was the one with hesitation.

"You will." She now said with a confident smile.

She turned around and got up on her hands and knees, shaking her ass a little before aiming it straight up at me.

"Do me this way." She said with a sly giggle.

How could I say no?

I got up and positioned myself at her cute little ass. I kissed it a little and rubbed it. She felt so soft and silky. Then I pointed my dick at her and slowly inserted it.

"OH! UH! YES!" she yelled. "Oh my god Jim!"

I began slowly moving in and out of her, her ass shuddered as I did this. Her pussy felt so tight as I did this. It just seemed to wrap itself around my dick. I reached around and pulled Hilary up and held her tits, flicking the nipples. This drove her wild. I then moved down to her pussy and my fingered it as best I could. She was screaming now, I thought she might pass out. So I slowed down and softly kissed her neck. I pulled out and she turned around and kissed me. We embraced, then I moved her down onto the bed with her legs open wide. And I fucked for all it was worth. She was screaming again.


She was like an animal with her passion. She wasn't the delicate rose I'd known in London, she wanted me down and dirty this time!

I could feel my release coming faster and faster.

"I'm gonna come Hil! I'm gonna come!" I yelled.

"Do it! Do it!" she yelled

And I exploded into her. I felt myself drop onto her as I came. Her eyes rolled back as she came as well, her mouth open but very little sound coming out. I rolled off her and tried to catch my breath.

I lay there staring at the ceiling, then turned to my left to see Hilary with a beaming smile.

"Wow, that was even better than last time." She said breathlessly.

"Did I deliver?" I asked.

She giggled.

"Yes, yes you did." And she gave me a quick kiss on my cheek.

She sat up and got off the bed, she was a little wobbly as she stood up.

"Whoa! You did me better than I thought!" she laughed.

She went into the bathroom for a minute and then emerged, still naked.

"Come on, let's get a drink." She said taking my hand.

I always feel weird walking around totally naked, even with someone like her. But I must've given her some newfound confidence about her body. She wasn't afraid to be like this.

We went into her spacious kitchen. She looked so sexy with her tits jiggling like they did. She got a bottle of water and took a deep drink of it.

"Gotta keep hydrated." She said between sips.

I embraced her against one of the counters;

"That was somethin' else!" I said.

"You think so?" She said with a beaming smile.

"Oh, I know so darlin'" I said.

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