Journal of an Agent Ch. 04

Chapter 4: Alyssa Milano

Standard Disclaimer:

You must be 18 to read this story, be able to read erotica in your community, not be offended by the contents of it...blah blah, you know the rest.

This story may be distributed freely, for commercial or non-commercial use, but PLEASE leave my email/name on it! That's all I ask!

This is Part 4 of an ongoing series. Yes I know the celebs don't act like this in real life, but this is a fantasy after all.

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Since I took over my father's talent agency out here in L.A., I haven't really had to go chasing talent to bring onboard for the company. Thankfully, he left me a large stable of great actresses and musicians who are not only talented, but also hot as hell and sexy. And as great as the sex had been with the clients I had gotten personally involved with, I was still looking for something more. A more meaningful relationship. Sure, there was always the fall back to my personal assistant Julie (who I was almost certain had a thing for me) but dealing with an interoffice relationship like that wouldn't be the best idea.

So when I heard that Alyssa Milano, the child star who had grown up into a very beautiful woman, was looking for some one new to represent her, I jumped at the chance. We were close to the same age, and ever since watching her on "Who's The Boss" back in my younger days, I had had a boyhood crush on her. I had Julie get me her home phone number and one evening at home, I actually felt nervous as I called her house.

"Hi, you've reached Alyssa. Leave me a message and I'll call you back." said the recording on her answering machine.

"Damn," I thought to myself "She's probably out with her boyfriend. I'll just leave a message,"

*** BEEP ***

"Hi Alyssa, my name is Dean Simonds and I am from the Shooting Star Talent Agency. I heard you were shopping around for an agent and I was wondering if we could get together for lunch or dinner sometime to discuss you coming aboard. Give me a call when you get a chance. My number is..."

CLICK "Hello? Dean? You still there?" rang out her sweet voice. My heart jumped into my throat, but I regained my composure.

"Yes, hi. I thought you were out or something," I said, trying not to sound nervous.

"Nope, I just screen my calls. Ever since Charmed got so big, I have had to change my number 3 times! People keep posting my number on the Internet. It's really scary. Any ways, you are correct, I am looking for a new representative, so we do need to sit down and talk," she said.

"Ok. Well, how about we have lunch two weeks from this coming Thurs-" I said, but was cut off.

"Look, first off, I don't schedule more than two days in advance. Why don't we have dinner now? I'm free and you appear to be available as well, if you're making calls to my house at 6 on a Friday night," she said, laughing.

I was caught a little off by this, but without even thinking I jumped at the chance.

"Yes. I'm free. I can meet you virtually anywhere in about 45 minutes. Where do you want to go?"

"How about that Italian restaurant two blocks off of Rodeo?" she said.

I knew the one she was talking about. Great food, quiet atmosphere, and not a huge drive for me.

"Sounds good. I'll meet you there at 7. Sound good?" I asked, secretly praying and hoping a thousand times over in my head.

"Sure thing. I'm going to dress down to keep the fans away. I'll be the one in jeans, a green sweatshirt and white tennis shoes. I'll meet you around the side of the building," she said.

"Great. Cya there," I said. Shaking, I hung up the phone. The office was quiet now, so I shut the door to my office and then did a small jump in the air. "Yes!" I said.

Changing into a nice coat and putting on a fresh tie, I got myself ready hurridely. "Ok, calm down now Dean. This isn't junior high." I told myself. God, I felt as nervous as my first date back when I was 15.

I arrived at the restaurant 10 minutes early and went ahead and got us a table. For a Friday night, I was surprised how quiet they were. Taking a seat facing the door, I drank two glasses of water just waiting on her. Finally she arrived, 5 minutes late. She was dressed like she said she would be, although the baggy clothes did little to hide her curves. She was wearing a dark pair of sunglasses to help shade her eyes from being recognized. I motioned her to the table and she walked over towards me. Wanting to impress her and be a gentleman, I pulled her chair out for her and pushed her in to the table. The perfume she was wearing was intoxicating and try as she might with the outfit she was wearing, she had an heir of sexuality that I hadn't encountered in many women. Taking off her sunglasses, she sat down and I returned to my seat.

"Hi. I'm so glad we could get together. Since Charmed got so big, I've wanted to try moving on to movies. Do you think you can help?" she asked, smiling.

"Well, my firm carries a whole lot of weight with the studios. If you are really serious, I'm sure that we can work out something," I replied.

"That's great. I'm thinking maybe a role in a comedy or something. After doing Who's The Boss for so long, I'd like to think I've developed a knack for comedy," she said, pausing. "You know, I must say, you are as attractive as you sounded on the phone," she said.

Laughing, I asked "Is that a good thing or a bad thing?"

She laughed softly in return. "No no, it's a good thing. I can always tell how a person looks generally by listening to them on the phone. I guess it's some sort of sixth sense or something," she said.

"Well, thank you. I probably don't even have to tell you how beautiful you are," I said, smiling.

Amazingly, she blushed a little bit. "Thank you. Something I've noticed since I've been in Hollywood, which is a long time, is that with all the beauty and glamour out here, when you actually talk to a person, you can tell how genuine they are. You couldn't have grown up here, because you seem so honest. Maybe my radar is off, I don't know" she said, shrugging half-heartedly.

"No, I'm from back east. I just got out of college about six months ago. I was going to be a lawyer until my father passed away and I inherited the agency," I said, sipping from my water.

"Oh, I'm sorry to hear about your father. That must have been horrible," she said sympathetically.

"Not really. He left us when I was young so I never got to know him. I wasn't even going to come out here but was talked into it by his lifelong assistant. I think I like it out here though, so I will probably stay for a little while longer at least," I said.

"You've got to stay," Alyssa said, smiling. "You have to be here to take care of me,"

The waiter finally arrived and took our order. Dinner arrived 20 minutes later. Throughout the meal, we continued to have a great conversation, that was hardly about business at all. Alyssa and I clicked on a personal level, sharing childhood memories and experiences of growing up. Despite growing up in totally separate ways, I felt a real connection with her, and that she understood and felt what I had gone through without a father, and I think I understood her struggles growing up in a world like Hollywood.

Towards the end of the meal, Alyssa returned the conversation back to business. As the check came, I reached to pick it up but Alyssa's hand covered mine. Her skin was exquisitely smooth and her hand was so warm and alive.

"You know, I'm a big girl. I can pay for my own dinner," she said, making a ritualistic effort to be free from the male stereotype of paying for the meal.

"I know you can. But hey, this is a business dinner, so the agency will pay for it. We both win out," I said. Reaching into my wallet with my other hand, I noticed Alyssa's hand was still on mine. Looking up into her deep brown eyes, she rubbed her fingers slowly over my hand. God, her touch felt so right.

"Would you like to come back to my place for drinks and maybe some coffee? We can talk about possible movie roles and you can look at some scripts I've been given," I said.

"I'd love to. We can take my car, if you can give me directions," she said, her gaze never leaving my eyes.

I agreed, and we got into her car. The ride back to my house was quick, as Alyssa tore down the freeway in her bright red Z3. With the top down and the cool sea breeze blowing onto her face, and the moonlight from the half moon that was out and shining so brightly over the Pacific, her beauty radiated.

When we reached my house, a small (by California standards) mansion, I took Alyssa's hand and led her to the entertaining room. She took a seat on the couch as I went to the bar to fix us some drinks.

Handing her her drink, I sat down on the couch next to her and handed her two or three scripts I had been reviewing from off of the coffee table. We spent the next few hours drinking and discussing the scripts. It was decided that I would try and get Alyssa a role in a situation comedy about a man who wakes up in a Vegas hotel and is suddenly married to three sisters. She would of course play one of the sisters. After finishing my drink, I rose to fix Alyssa and myself another round. Glancing at the clock, I realized it was 2 AM. I had no idea time had went by so quickly. Alyssa must have realized it too, for she rose from the couch.

"Wow, it's late. I probably she head home. I have an hour and a half drive ahead of me," she said, sipping from the drink I had just given her.

My heart sank a little bit, but she was probably right, she should head home. Walking her to the door, she stopped in the hall way to admire one of the paintings on the wall.

"Wow, is that a real Warhol? It's beautiful," she said quietly. I was impressed by her recognition of the art.

"Yes, it is. My father was an amateur art collector. The paintings in the house were here when he died and I moved in," I said.

"It's beautiful. The colors are so radiant," she repeated to herself.

Turning around to face me, our faces were less than 6 inches apart. For a moment, I sensed that she was debating about what to do, but the moment was quick and she leaned in and kissed me softly on the lips. I stood there savoring the feeling of her mouth on mine, and then leaned in to kiss her just as gently as she had kissed me. She returned the kiss, and I forced her against the hallway doorframe lightly, putting my arms over her shoulders, kissing her sweet mouth. Her lips and tongue were so warm and soft, I felt like I would die from the sheer bliss. We stood in the hallway for another ten minutes kissing, before she finally broke the kiss and put her hand on my chest.

"Maybe...I shouldn't drive..." she said, kissing me again in between words. "Having...drank...and all," she said, gasping slightly between kisses.

"No...as your agent...and friend...I don't think...you should," I said, kissing her the same way. She wrapped her other arm diagonally around my shoulders, and we were lip locked again for a few minutes.

Wrapping my own arms around her waist, I pulled her towards me. She laid her head on my shoulder, and I felt her soft hair brush across my face. The shoulder length auburn brown hair reflected the light from the outside gate light beautifully, and when she rose her head from my shoulder once more, the light caressed every curve and bend of her face. I had never seen anything as beautiful in all my life. Taking her small, soft hand in mine once more, I started to lead her upstairs to my bedroom. As we crossed the den, she stopped. For a moment, my heart sank once more as I realized how forward I was being and that she probably didn't appreciate it.

Instead, she moved towards the couch and laid down, pulling me on top of her. Resting my arms beside her side, her breathing was becoming more ragged as we kissed once more. I could feel myself getting aroused by all of this, and judging from the panting coming from Alyssa's mouth, she was too. Making my way up and down her neck, I softly placed kisses on her neck and cheek, savoring again that wonderful perfume and the radiant sexuality coming from her. Lifting her shirt up slightly at the stomach, she pulled it up, exposing her beautifully soft and firm naval area. Her bellybutton was pierced with a diamond stud, and it shone brightly in the soft light of the floor lamps of the room. Diverting my attention from her neck, I moved my mouth to her stomach, kissing and licking all around her navel and tummy, moving my way slowly up her chest. Pushing her sweatshirt all the way up to the base of her breasts, I finally got a glimpse of her bra: a light, baby blue silk pushup from Victoria's Secret. Alyssa lifted her head and looked directly into my eyes as I raised my head up from her belly. Shifting her arms just enough, she grasped the end of her sweatshirt and pulled it over her head, leaving her in just the light blue bra. Her breasts were heaving up and down of virtually their own accord as my kissing made way up to her cleavage. Kissing and licking first one breast and then the other, I slowly slid the left cup over her nipple and exposed it in it's aroused state to the air of the room. Her nipples were large, a light brownish pink. Her areolas were also large, covering the majority of the front of her breast. Taking the nipple in between my teeth, I licked and squeezed lightly, eliciting a soft moan from Alyssa. My free hand moved to the other breast as I massaged and kneaded it, rolling it around in my large hand. Her skin felt as soft as I had thought, delicate and fine on the surface, but an extraordinary heat radiating from under it. I moved my mouth from her left breast to the right, copying the same style of pleasuring I had just been doing, only this time taking it a little faster.

Alyssa seemed to like this better, and her hand grasped my hand away from her breast and moved it down to her crotch, where I could feel the wetness building through her jeans. Finally, I stopped licking her tits, and she sat herself up some on the couch, only to move her hands to her jeans and slide them down sexily. She was wearing a pair of white cotton panties that did very little to cover her beautiful little pussy. I could see the moisture from her lips wetting down the surface of her panties. Slipping a finger inside, Alyssa began to play with herself, thrusting a finger in and out of herself at a slow speed at first, then going at it tremendously. I, in the meantime, was busy unbuttoning my pants and pulling down my boxers. As I let my boxers fall to the floor and my cock sprang to attention from Alyssa's pleasuring of herself self induced orgasm arrived, and her body shuddered in pleasure as it went stiff and a soft cry escaped from her lips. Panting and out of breath, she finally laid back on the bed, with her eyes closed and her head tilted back. Alyssa opened her eyes and looked at me, smiling slightly.

"Sorry about that. But I'm sure you enjoyed the show," she said slyly.

"Oh yes, very much so. I'm just hoping the second act will be as good as the first," I said.

Getting onto her knees, Alyssa slid her panties off from her full hips onto the carpeted floor below. Reaching out with both hands, Alyssa grabbed me by the ass and pulled me towards her with one hand, and took my hard dick in her other. Looking up at me the whole time, she placed the tip of my dick onto her bottom lip. Extending that magical tongue of hers out slowly, licked the tip softly. The trail of her saliva, mixed with my precum, created a strand extending from her lips to my dick as she slowly pulled her mouth away. Still maintaining eye contact, Alyssa smiled up at me. Pulling my dick into her mouth once more, this time sucking in about 3 inches of my 9 inch member. I could feel her tongue swirling around all over my sensitive foreskin area, teasing and pleasing it as it moved around like a nimble serpent of pleasure. I was in heaven as she was doing this, wanting to force more of myself into her able and willing mouth, but Alyssa was setting the tone totally on this experience. Slowly I felt more and more of my dick sliding into her mouth, until I realized that the head had gone down her throat. My God was she a good cocksucker!

Alyssa let some of my dick slip out of mouth, but began quickly moving it in and out with ease, her lips and tongue sliding all around my dick. Her head was bobbing like crazy now, but she was using JUST her head. One of her hands was busy fondling and playing with my balls, while the other was busy frigging her clit. Alyssa broke her gaze with me as she closed her eyes, picking up speed on her sucking, sometimes deep throating me, other times letting my dick come totally out of her mouth and smack her upper lip or rub against her cheek. A nice drop of precum had ended up on her upper lip and it remained there while she sucked me off, glistening in the light.

"Alyssa! Keep it up! I'm about to cum!" I panted. Surprisingly, Alyssa pulled my cock from her mouth and instead ripped off her bra and placed my dick in between her beautiful breasts. Using her hands now, she grasped her breasts and began to tit fuck me with them. I helped along things by bucking my hips up into her tits. My dick would occasionally smack onto her chin and glide up it to her extended tongue. She would try desperately to lick it as it came up, like a little girl trying to get that last lick on a lollipop. Finally, I couldn't stand this tit fucking standing up much longer, so I laid her back onto the couch and put my knees by her sides. My pace was furious as I slid my dick between her soft globes. Alyssa was moaning and bouncing all around while this was going on. At last I felt my balls swelling and I unloaded a massive jet of cum onto Alyssa's tits, mouth, chin, nose and even some in her hair. Alyssa gathered up the cum from her face and proceeded to smear it into her tits.

"Old Hollywood trick. Supposedly it's good for the skin," she said dryly.

Watching her do this made my fading erection hard again, and I stroked myself back to full attention. Alyssa spread her legs wide on the couch, draping her right leg onto my shoulder. Positioning myself in front of her cunt, I slowly eased the head in, and then in one swift motion shoved my dick in to the hilt inside of her. Alyssa gasped at this sudden action, but her pussy matched my pace, as I could feel it trying to suck as much of my meat into her. Her box was warm and wet, and the walls of her canal were silky and smooth. I felt myself bottom out inside of her, this thrust eliciting an even bigger groan from her. As we laid there fucking like two rabbits, Alyssa put her hands on the side of my face and pulled me close to her, kissing me deeply.

"Dean, I want this to be more than a one time thing. I feel a connection. Please don't let this get away," she whispered into my ear.

I too felt a deeper affection than just some piece of celebrity ass I had had, and I told her so.

"Don't worry. I feel the same about you. I want to try and make this work," I said, gazing again into her deep eyes. Her face looked so innocent and sweet, the sweat lightly perspiring on her forehead as we moved back and forth in unison.

Alyssa smiled at me and whispered "I know we can. Thank you,". Suddenly her body tensed up and she orgasmed. I knew that I was pretty close to coming again, and told Alyssa so. I thought she would want me to pull out of her, but instead she pulled my body closer to hers, my chest crushing her breasts and nipples against my own. Shuddering as well, I released a steady stream of cum into her, feeling the hotness of her cunt juices coating my shaft as I finally pulled out of her.

We finally moved to the bedroom and laid together on top of the bed for a while cuddling and fondling each other. The last glance I had at the clock told me it was 5 AM. I had no idea our lovemaking had lasted so long. I drifted off to sleep with Alyssa Milano wrapped in my arms, her head resting lightly upon my chest and my arms around her perfect body.