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
"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
CLICK "Hello? Dean? You still there?" rang out her sweet
voice. My heart jumped into my throat, but I regained my
"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
"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 hurriedly. "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
"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
"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
"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 hallway to admire one of the paintings on
"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
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 hairbrush 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
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 its 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
The rest of the weekend we made love and talked, and our
relationship and connection grew. I hadn't felt so close
to a person in years, and I could only think that she
felt the same way. Over the next few weeks we saw each
other almost every day and I stayed true to her, as she
did to me. I felt that our relationship was headed to a
next level until I had a moment of weakness one day that
threatened to rip us apart...