Adventures of Hollywood Jim Ch. 17

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An adventure with Alyssa Milano.
4.6k words
4.59
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Part 19 of the 101 part series

Updated 02/26/2024
Created 08/06/2008
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It was inevitable.

My excesses would catch up with me sooner or later and I'd have to see a Doctor.

I was a nervous wreck that morning, my performance just wasn't right.

"Aches and pains?" I was asked.

"Yep, got those." I answered.

"Unusual discharge?" was the next question.

"Yep, that too." I answered.

"Come right in." was the suggestion.

So I headed for the clinic down the road. It handled me and several others that day. I now place myself in the hands of the best in their business. I sit and wait, wondering what the others are here for.

"Wonder what he's got?" I thought looking at one.

"Things don't look right with her." I thought about another.

And then the specialist comes in, and calls my name.

I tremble as I raise my hand, and he comes over with a clipboard and sheets of paper.

"So what's the prognosis?" I asked fearfully.

"Oh, your cars' gonna be fine." He answers.

The color returns to my face.

He goes on to explain that the overheating problem and general creakiness in my Honda's performance was due to a leak in a coolant pipe that needs to be replaced. Hence the unusual discharge. He's surprised it held up as long as it did, considering the mileage.

I'm just waiting for the price of all this diagnosis and treatment.

Luckily I find out that having Chris as a friend gets me a nice discount.

"OK, set it up." I say.

That's when I get the zinger.

"It'll be about three hours to fix everything." He says.

The color leaves my face.

Well, it's gotta be done, might as well make good use of my time.

I walk up the road to a McDonald's and get breakfast and newspapers for the long wait.

As I'm sitting there, biscuit crumbs dropping around me, I see a pretty brunette on her phone, a sports magazine in hand. She's wearing pink sweatpants and an LA Dodgers shirt.

"Right, I'm at the dealer now...Um, I'm not sure, they said about an hour. So I'll meet you there...OK, bye." She says with a crisp, business-like tone before hanging up.

"These guys can always keep you as long as they want, huh?" I say.

"Looks like it. What are you here for?" she asks.

"Oh, my Accord's been overheating, needs some kind of coolant pipe." I answer.

"I had the same thing on my car." She says.

"You have an Accord too?" I ask.

"Oh no, BMW convertible." She says with a proud smile "I love it."

"Man, I would too." I reply.

"Oh, I'm Alyssa." She says.

"Jim." I try to wipe off whatever grease I have from the biscuit before shaking her hand. It feels ever so soft.

"Sorry, darn McDonald's sandwich." I say apologetically.

"Oh, no, don't. I love those, I could eat them every day, wouldn't be good for this though." And she pats her perfectly flat stomach.

"I know what you mean." I said.

"But I've gotta give them credit, it was my first job." She said.

"You worked there?" I asked.

"Well, sort of. I did a commercial for them in Japan." She said.

"Really? How'd that happen?" I was surprised.

"Well, that usually happens when you're an actress." She said.

"Oh, I get it." Then it hit me. "Wait a minute, wait a minute." I said slowly.

She looked at me and smiled.

"Uh, are you-?" I said nervously.

"Right, Alyssa Milano." She said with a "now you know who I am" smile.

"Whoa! I thought you looked sort of familiar." I said, smiling now.

She smiled back at me.

"I guess your car isn't quite as charmed as you, huh?" I joked.

"Not quite!" She laughed heartily in response.

Just as she said that, she was told her car was ready.

"Oh, I'm sorry we didn't get to talk more. It was nice meeting you Jim." She stood up and went outside to her car.

"Yes, good luck in your future." I said.

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

And I spent the remaining time alone, oh well.

Well, even "Hollywood Jim" isn't as 'charmed' as others are sometimes.

The next day, Chris was all excited about an invite he'd gotten to The Eagle.

"Derek's having his birthday bash there and we're invited. And I know you hate this sort of thing, but you really should go. It's invitation only and it'll be a smaller crowd anyway." He said.

"Well, OK, I'll go. That place isn't so bad now that I think about it." I replied.

Now usually a night out with him was something I avoided at all costs. But this was different, Derek Adams was a friend after all, and Chris had told me how they'd helped one another out at different times.

"How'd he get that place anyway, I thought he owned Red Light District?" I asked.

"Well, he used to own both. He always had the Eagle and thought he could run both places. But he got bored and Red Light was burning him out anyway, so he sold his interest and stayed with Eagle. It's like he woke up one day and said 'I've had it'." Chris explained as we headed out to his Porsche.

"I'll pick you up at your place in an hour." Chris said as he drove away.

When he showed up I walked out to the car and as I opened the door got a surprise.

"Hi, 'Hollywood'!" yelled Candy and Mandy with a giggle.

Chris had the girls from Tigress crammed into the back seat of the Porsche.

I laughed, but groaned at the same time. Chris had this mischievous smile on his face.

"Well, you didn't think we were going alone did you?" he asked innocently.

I climbed in and immediately got a kiss on my cheek from one of them.

The Porsche roared off to the Eagle.

The Eagle was crowded but it wasn't a wild crowd, Derek invited just anybody famous there. It was Derek's night, and he controlled everything. The drinks flowed freely and the music was what he wanted to hear, quite a change from the norm.

My plan was to get a few in me, wish the birthday boy well and then bum a ride home from somebody. Chris was bound to be there all night. And I could see a few friends of ours there, so I figured I had my ride all set.

I wandered about the club, checking out who was there. It seemed like a lot of supermodel-types whose names escaped me. Chris was deep in conversation with 2 of them, and Tigress was up in the DJ booth.

And I was bored.

"Hey, Jim!" I turned and there was Derek.

"Hey, happy birthday Derek!" I said shaking his hand.

"Thank you, thank you. It's always a joy turning another year older." He said with a touch or sarcasm. "I didn't get to talk to you much last time. I have to give you a lot of credit for this place."

"Me?" I asked, stunned.

"Right, the last time I saw you was at Red Light, remember?" he said.

"Well, yes. But I didn't stay all that long..." I said.

"That's the thing, there was all that chaos with Lindsay, stuff got broken, it was just a mess. That's what gave me the incentive to walk away. The fact that you chose to leave. You could've stayed. But you didn't. You just didn't seem like the kind of guy for a place like that. So I figured, neither was I."

I was stunned to hear all this.

"So the next day," he continued "I called my partners, said 'I'm out!' and came back here to stay." He said stretching his arms out.

He put his arm around me now.

"And you're the reason I did that." He said.

"Well, thank you." I said hesitantly.

"Aww, come on. Don't get all weepy on me, let me get you a drink pal. Corona, right?" he pointed at my beer.

"Yes, no wait. This should be special, get me a Jack and water." I said with sophistication.

"You got it!" and he went off to get my drink.

As I stood at the bar, I looked down one end and saw Alyssa there talking with another girl. She saw me and her face brightened up. She immediately came over to me.

"What are you doing here?" she asked excitedly.

"My friend and I run a photo business, we're friends of Derek's." I said.

"So, how'd you car make out?" she asked.

"Oh, not bad. I'll probably get another 50,000 miles out of her." I replied.

"That's good to know." She said with a smile.

"Can I get you another drink?" I offered.

"Oh, sure. A glass of red wine." She said.

I placed her order as Derek arrived with my drink.

"Hey, chatting up the guests, huh?" Derek said to Alyssa.

She laughed and Derek told her about my connection with him.

I was actually blushing while Alyssa was looking at me with a smile.

As the night wore on, I sat at the bar and kept an eye out for who was leaving or about to leave. Alyssa returned to the bar area and sat next to me. She looked simple, yet so pretty in a blue fitted Dodgers t-shirt and black jeans.

"Hey, you." She said jovially.

"Hey back." I replied, raising my glass and toasting her.

"What are you drinking?" she asked.

"Jack Daniels and water." I said.

"I should get one of those." She said looking for the bartender.

"No, no, allow me." I said

And 2 more jack and waters came to us.

As we sipped our drinks, we both talked about our work, she seemed to have an endless amount of gossipy stories about her work and people she knew. Her thick black hair looked so pretty and she began to idly twirl it while we talked. Her eyes gazed into mine.

"How'd you get into the photo business?" she asked.

"I always liked it, the pictures, that is. I'm not a businessman by any means!" I said.

"So you take the pictures and Chris does the business?" she asked.

"Well, little of both." I replied. "I like the pictures more."

"Me too." She said.

"Excuse me?" I asked, a little unsure.

"I like taking pictures, and being photographed. Heck, it goes with this business." She said.

"Oh! I see." I said.

"You'll have to see my photo collection sometime." She said.

She then looked at her Tag Heuer watch.

"Oh, man I didn't realize how late it was."

I looked at my Rolex watch (OK, it's really a Timex, but from afar it looks like a Rolex).

"Geez, I wonder if Chris is still here, he's my driver tonight." I said.

"You didn't drive here?" Alyssa said.

"No, he insisted on driving." I replied.

"That'll be good, I'll drive you home. Where do you live?" she asked

"Just off the Beach Roads." I said

"Oh, that's right on my way, we could stop at my place for a nightcap and I can show you my collection." She said.

"Oh, well, uh..." I said trying to figure out where this was leading. Either way, I needed a ride home.

"Let's go!" she said as she quickly downed the rest of her drink and took my arm as we walked out of the club.

Alyssa's BMW was one sweet ride as we headed for her home. We pulled off into a quite suburban neighborhood and into the driveway of a retro 60's ranch-style house.

"Wow, this reminds me of where I grew up." I said looking around at the other houses.

I turned to Alyssa and she quickly kissed me on the lips.

I jumped back a little.

"What was that for?" I asked.

"Oh, for someone special." She said with a smile as we walked in. "Let me show you around, you want a glass of wine?"

"Uh, yes, that'll be fine." I said, still a little stunned.

Could this be heading where I think it is?

Alyssa came out of the kitchen with 2 glasses of red wine.

"Salud`." She said in Italian with a smile as we touched glasses. I responded in turn.

Alyssa proudly showed me around her home, it was much bigger on the inside than I thought. There were hardwood floors and high ceilings throughout, so our voices echoed. Her bedroom was elegant with an antique brass bed. A media room seemed more like a shrine to the LA Dodgers, what with all the memorabilia in it. She then took me into an enormous bathroom with a Jacuzzi bathtub atop marble steps.

"Man, this is something. Then again this whole house is something." I marveled.

"I designed a lot of this place myself, especially this room." She said as she lit some candles giving the room a golden glow.

The more time I was with her, the more nervous I became. Should I be doing something here?

Fortunately Alyssa solved that problem.

"You wanna take a bath?" she said with a smile.

"Excuse me?" I said, stunned yet again. I nearly dropped my wine glass.

"Yeah, come on! Wine always tastes better this way." She said.

"Uh...I'm not sure about this." I stammered.

"Oh come on!" she said as she turned on the water.

Alyssa started undressing. And realizing I better do something, I did the same.

She removed her heeled shoes and pulled off her shirt. Then unhooked her bra and exposed her tits. I removed my shirt, still uncertain what was going on. She quickly unbuttoned her pants, pulling them and her panties off at the same time. She was now completely naked in front of me as I removed my pants.

We both looked at each other.

She smiled.

"You look really nice." She said.

"You look...incredible." I said in a somewhat raspy voice, I was so nervous.

Alyssa had beautifully round tits, sure they were augmented but still gorgeous. What really grabbed my attention was something some might not find attractive, but yet in a strange way, I did.

Her pussy wasn't shaved like all the other starlets.

It wasn't a wild, unruly mess, but a jet black colored area around her love nest. It was trimmed, yes, but definitely there.

It made me flash back to my youth, and now here I was, with a fantasy figure from my youth.

"You think so, huh?" she said, bring me back to the present. "Come on, let's get in the tub."

She gingerly stepped in and got acclimated to the hot water. I could tell she was watching my dick grow, and smiling all the while.

"Mmm, the water feels so good." She said gently treading the water.

I now stepped in and moved towards her. She slowly put her arms around me and we kissed. She then picked up her wine glass;

"Salud`mi amore`(salute, my love)." She said softly now.

I said the same, in my best fractured Italian.

The candles were obviously doing their magic. There was a scent of lavender and the room had a golden glow that was accentuated by Alyssa. Her body seemed to glow as well. She softly placed her hand on my head and we kissed deeper, her tongue merging with mine.

"I'm...I'm sorry, I'm so nervous right now." I said.

"It's OK, you'll be fine." She smiled and said softly. We were gazing into ne another's eyes now.

"Do you like being here with me?" she asked softly.

"Yes, very much so." I replied.

"I like you too. Just relax, I'll make you feel real good." She said in a soft and tender voice. Her hands were on my shoulders and they slowly worked their way down my chest.

Sure, I'd been with several starlets. But the first time with someone is always strange and nerve-wracking.

"Do you want to touch me? I wish you would." She said.

I gingerly placed a hand on her breast. She smiled and fluttered her eyes slightly.

"That feels nice." She said.

I began to enjoy the feel of her breast and felt it more lovingly. I felt her nipple as it hardened to my touch. Alyssa began to moan a little and leaned in to my ear. I could hear her breathing become more rapid.

"Ohhhh....baby." she whispered. "That feels good...you look so hot...touch my nipple...yes, that's it."

I kissed her again, our tongues danced with one another and she smiled when we released.

"Oh man, that felt good." She said with a smile. "I can tell you like doing this."

"Oh yes, I do like it." I was now smiling.

"Good." She whispered as she looked directly at me. "Let's have some fun."

Her hand went down under the water and I could feel her rubbing my dick.

"I can tell you like that, I love it when a guy gets hard." She said looking at me with a sly smile. "Means he's ready to fuck. I like to fuck."

"Oh, do you?" I said with a sly smile of my own. And then I became bolder. "Let's see if you're ready."

And my hands went down to her pussy and felt her. She jumped a little at my move.

"Oh!" she giggled.

"I can tell you like that." I said the same way she did. She laughed and gave me another kiss.

"Sit up on the edge." She said.

I sat up on the edge of the tub and Alyssa got the full picture of my hardness.

"That looks nice." She said as she took me into her mouth and began to slide me in and out of her mouth.

"Oh, you've got a nice dick." She said between slurps. It felt so hot seeing her do this.

"I love sucking cock, you know." She said.

"I can tell." I blurted out. At times like this it's hard to talk. I was now breathing heavily and my body was swaying itself back and forth as Alyssa was bobbing up and down.

"OK, let's trade places." She said.

She didn't need to ask twice! I was so eager to see that pussy of hers close up.

We switched places and Alyssa spread her legs wide for me.

"You like my pussy?" she asked.

"Uh, there's something I want to say but I'm afraid to spoil the moment." I said hesitantly.

"What?" she looked concerned.

"It's nothing bad, I just..." I began.

"You can tell me." She said.

"I love your pussy." I blurted out.

"Oh! I was worried there for a moment." She said, sounding relieved, then intrigued. "You like that, huh?" she said looking surprised.

"Yes, I just..." I was trying to find the right words. "How do I say this?" I wondered.

"You like a full bush?" she said. "I used to get it waxed and all but it grows back fast, it's the Italian in me. I think it's sexy"

"I like the way yours is. It makes me feel like...like...I'm really with a girl." I finally said.

"Well, this girl wants you to lick her hairy pussy." She said with a giggle.

I moved in and could see the pink folds of her pussy were glistening in the candlelight. Her fingers worked their way across the opening. She was very wet, and not just because of the water. My tongue gently licked her pussy, and my fingers slowly penetrated her. Alyssa let out a low slow moan as my tongue went inside her. I could feel her hand on the back of my head as she caressed me.

"Oh god that's wonderful..." she moaned.

My dick was rock hard now, but I was too busy loving this pussy of hers. It must be that sense of trying something new for the first time and not wanting it to end. I looked up and Alyssa's head was thrown back, mouth open, and hands on her tits.

"Oh yes! Oh yes! Baby I'm gonna come! Baby I'm gonna come!" she cried out.

"Come on my face!" I said, from where I don't know.

"Oh god! Oh god! I'm coming! I'm coming!" she screamed and I felt her love juices spray on me, she tasted delicious.

"Oh, give me a minute baby." She gasped.

I leaned backwards into the water and let it flow over me, Alyssa slid in and joined me.

"Man, that was hot!" she said as she kissed me, tasting herself.

"Oh yes, yes it was." I said with a naughty smile and a lick of my lips.

"I can feel your dick." She whispered. "We've got to do something about that."

"Um, do you have any condoms?" I asked.

"Oh, yes. I'm on the pill too. I love the pill." She said as she reached into a small basket near the tub. I stood up and she placed one on me.

"Know why I love the pill?" she asked with a naughty smile.

"Why?" I answered with fake innocence

She looked at my dick, now gift wrapped for her.

"Because I wanna fuck." She said.

And I slid my dick into her pussy. It felt so tight and Alyssa was moaning and grunting as I started to fuck her.

"Uhhh yeah! Fuck me Jim! Fuck...me...." She said with an almost animal-like voice.

I was ramming into her now.

"Fuck my pussy! Fuck it!" she growled through clenched teeth. "Oh God yes!" she cried out.

I couldn't believe I was fucking this girl, she was a maniac.

"I want your ass." I somehow said.

"Oh, yeah, I love that!" Alyssa said with excitement.

She turned around and offered up her ass to me, I began to slide it back into her but she stopped me.

"No, no, not there." She said and spread her ass cheeks wide.

"I want it there." She said.

"Oh, I see." I said, now realizing what she wanted.

She had a cute pink asshole waiting for me. I started to slowly push my dick into her.

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