“RING, RING, RING!”
Struggling to reach over and grab the phone, I almost fell
out of bed as the phone startled me awake. Glancing at the
clock through sleepy eyes, I saw that it was 6 AM. Way too
“Hh–hello?” I managed to croak into the phone as I tiredly
lifted it to my ear. I was greeted by an overwhelmingly
enthusiastic voice on the other end.
“Dean! What’s happening baby! How’s my favorite half-
brother!” the voice said.
“Jacob, I’m your only fucking half-brother,” I replied
Jacob was the illegitimate child of my father’s, who came
along a few years after I was born. Apparently my father
Martin had kept Jacob a secret from my mother and I,
sending money from his job as a bank manager (this was
before he walked out on us and started the Hollywood firm I
now manage) to Jacob’s mother. When my father disappeared
and the money did as well, Jacob’s mother called our house
repeatedly until my mother got so frustrated and got the
whole story out of her.
Growing up, Jacob was always like that cousin you always
meant to get together with but never could find the time,
for whatever reason. He was about 3 inches shorter than me
when I last saw him 3 years ago, but he and I certainly
shared the same eyes that my father (and his) had passed
along to us. My guess now was that Jacob was right out of
high school and calling his “favorite” half-brother to try
and weasel something out of me, since I inherited
everything. We always seemed to get along all right, but
didn’t really have too much in common.
“I heard you were going to be in New York next week, I
thought we could get together. I didn’t wake you up did I?
It’s 9 AM by my watch,” Jacob said. It sounded like he was
on a street corner somewhere and there was way too much
noise. I was also a little pissed because he had obviously
called my office and gotten out of Julie, my assistant,
that I was going to New York soon for a photo shoot
featuring Jennifer Aniston for the next issue of
“Jacob, time difference,” I muttered. “9 AM there, 6 AM
“Oh shit! Sorry about that bro. But hey, after we hang up,
go back to sleep, ok?” Jacob said apologetically.
“Thanks, I planned to do that,” I replied sardonically.
“Now what is it that you wanted?”
“Oh right. Well, I heard you were going to be going to a
photo shoot with Jennifer Aniston next week because you
represent her or something and, well, I’m a huge fucking
fan. All us New Yorkers are. So how bout it? We meet for
lunch, I show you my place and then you let me tag along.
Shit, you can call me your kid brother if you want, and I
promise I will be good. Cool?” Jacob said in a hurried
breath. It had been a while since I had been back to New
York City and I had forgotten how frantic everyone seemed
to talk there.
“Sure, whatever. I could use someone to pick me up at the
airport. Call Julie back and get the flight number and
information from her. And I want your solemn promise right
now that you will do as I say and keep your mouth shut when
we are around the talent,” I said.
“Really? WOW! Thanks Dean! I owe you big time. I guess I’ll
see you next week then, huh bro?” Jacob said, the
enthusiasm in his voice almost overwhelming.
“Yep. See you then,” I said, hanging up the phone and
falling back to sleep.
A week later and sure enough, Jacob was there waiting for
me at the airport. He hadn’t changed too much since I last
saw him. He was still around the same height, although much
bigger. I think I vaguely remembering hearing about how he
had been a star tailback for his high school football team.
He looked it too. I think I am in pretty good shape, but
Jacob’s arms were massive, almost twice as big around as
mine were, and I have to admit I felt a little intimidated.
However, it was all for naught because when Jacob saw me,
he gave me a massive hug and took my bags from my hands.
“Welcome to New York City,” Jacob said with a broad smile.
“The city that never bathes…I mean sleeps,” he grinned.
“Thanks. I don’t have any other luggage so let’s just go
back to your place now, alright?” I said.
Walking outside to the parking lot at LaGuardia airport,
the weather was surprisingly warm and nice. Being April,
the city had just started to lose some of that winter
chill, although it wasn’t into the scorching New York
summertime yet. I was also amazed at how clean the air in
the city seemed to be. When I had been there last was the
pre-Guilani period and I guess he had done a pretty good
job of cleaning up the pollution.
Another surprise came when we got to Jacob’s car. It was a
souped up Porsche 911, all black with crystal clear
headlights, and a red stripe that faded down the side. He
could tell my look of surprise:
“Graduation gift from my mom. You didn’t get EVERYTHING
when the old man croaked you know,” he said, winking.
We got in the car and headed uptown. He lived just outside
Greenwich Village, in a building that looked to be recently
renovated. We pulled into the parking garage and headed
inside. All and all, not too bad a lifestyle for someone
just 18 years old.
Inside his 3 bedroom apartment, it looked like the typical
teenagers room though. He lived alone, but probably kept
the house in more disrepair than 4 people living there
would. He made no qualms about apologizing for the shape of
his house, and I made no comments about it. I too was like
this once…except I really WAS poor.
Jacob got us both a beer from the fridge and we sat down to
“So, when will I have a chance to meet the lovely Mrs.
Aniston?” Jacob said, that sly grin never leaving his face.
“Tomorrow. I’m heading over to Entertainment Weekly’s head
office downtown around noon for lunch with the editor of
the spread they are doing on her. Then, around 4 or so,
Jennifer is getting there for her photo shoot. Because I’m
sure you have no interest in the business end of this
thing, I’ll give you the address where they are located and
you can meet me there around 3:30. The only catch to all
this is that you will have to be my chauffer around town
tomorrow and take me to the airport the next day as well,”
I told him.
“That won’t be a problem. I’m not starting classes till the
fall, and since all I do anyways is stay out late partying
and sleeping in till 2 in the afternoon, it’s not like I
will be missing anything,” Jacob replied. “Speaking of
which, up for a night on the town tonight? I can show you
all the best spots in NYC and I promise we will have a good
time. That is, if you are not too old,” he said with a
I couldn’t help but laugh. “Too old? Boy, you don’t know
the first thing about partying when you are with me.
Remember, I’m from LA,” I said with a grin.
We went out that night and Jacob was right, I did have a
really good time. But since I had to get up and work the
next day, I didn’t want to be hung over, so I drank very
little. Jacob on the other hand got quite trashed and I
ended up having to drive him (and the little blonde hottie
he picked up named Alicia) back to the apartment. As soon
as we were in the door, Jacob took Alicia to his room and
made a weak hand motion that I took to imply “You can sleep
in one of the other rooms”. His mouth and other hand were
too pre-occupied roaming all over Alicia’s body.
I grabbed a soda from the fridge and sat down to watch
Conan, as I remembered that Penelope Cruz was going to be
on. I had developed an affinity for her recently after
seeing a test screening of “Blow” and made a mental note to
myself to check to see who her representation was when I
got back to LA.
But my television watching was cut short, as just a few
minutes after I sat down, I started hearing moans coming
from Jacob’s bedroom. I turned the TV up loud to try and
drown them out, but it was no use: Alicia’s moans and
screams kept getting louder. When I had the television
turned up all the way, and could still hear them, the moans
subsided just for a moment so that Jacob could have the
audacity to yell at me: “Turn the TV down! You trying to
blow out the goddamn speakers?”
Throwing my hands in the air in exasperation, I turned off
the TV, finished my soda and went to the bedroom. With the
door shut and everything else quiet, I finally fell asleep,
mainly from being tired from the flight.
The next morning when I woke up around 10:30, Alicia was
gone and Jacob was at the table wearing the same clothes he
had worn yesterday, minus his pants (although he did have
boxers on), eating a bowl of cereal. He looked a little
hung over, but I knew he would shake it off. I joined him
and we talked a little over breakfast, but since it was
11:00, I had to go get in the shower and get ready. I hate
being late for a client.
Jacob dropped me off at 12:05 in a rush, after I chewed him
out the entire way there about how I hated being late. I
left in a huff but straightened myself up for my meeting.
The meeting and lunch went well, and I got a tour of
Entertainment Weekly’s offices for an hour or so, making
small talk with the photography editor and the writers for
a little while.
Glancing at my watch it was about 3:40 so I excused myself
for a moment and went down in the lobby to meet Jacob. I
was shocked by how he was dressed. Wearing a pair of
polished black shoes, black slacks and a light blue shirt
with a black sports coat over it, he looked nothing like
the grungy kid that dropped me off in a t-shirt, boxer
shorts and sandals this morning. He even had shaved off the
scraggly beard he had been growing and his hair wasn’t a
total mess like I figured it would be (truthfully, I wasn’t
sure WHAT to expect when he showed up). Very impressive, he
almost put me in my white collared shirt and navy blue
pants to shame. Almost.
As we got in the elevator, I drilled him again on how to
behave. He wasn’t to talk unless spoken to, not to touch or
stare and generally just act like a walking mannequin while
he was there. Jacob nodded to all this solemnly, but I
couldn’t tell if he was patronizing me or was being
sincere. The elevator dinged on the 5th floor and the doors
began to open. Taking a deep breath, I stepped out.
Walking down the hall, we found the studio where the photo
shoot was going to be. There was an assistant at the door,
but she just smiled at us and waved us in. The room was
quite large, bigger than I thought it would be. In the
center was a white backdrop, with a small table and a few
other items. On the ground was a dark blue crushed velvet
sheet, that filled in the whole space. A portion of it was
balled up, so I figured that it would play somewhat of a
role in the photos.
Looking around, I didn’t see Jennifer anywhere. However, to
my surprise, Lisa Kudrow was standing around talking with a
few of the people. I walked up to her and Jacob followed
right behind me, quiet as a mouse. I think he was star
“Lisa! What are you doing here!” I said, extending my hand
as I walked over to her. She shook it and gave me a hug.
“Dean, how are you? Jennifer and I just finished shooting
an episode earlier this afternoon and since I didn’t have
anything to do, I decided to come along. Jennifer is in
makeup, changing into her outfit for the shoot. I think the
better question might be why are YOU out here?” Lisa
replied. We had gotten to know each other fairly well when
the cast of Friends had been out once or twice to LA for a
taping or something else related to the show. I had
thought about luring her away from her agency, but Julie
had told me not to bother because Lisa had a deep
friendship with her current agent.
“I’m doing great. I came out here to see the shoot and work
with her on maybe some more movie roles, and more or less
for a visit to the Big City,” I said.
“Excellent. And uhh, who is your friend?” Lisa said,
pointing over my shoulder to Jacob, who had stayed where he
was when we walked in.
I looked over at him and motioned for him to come over.
“Lisa, this is my half-brother Jacob. He lives here in New
York so I thought I would spend some time with him while I
was here. He let me stay at his place uptown. I know he
seems a little quiet, but he says he is a really big fan of
the show,” I said, pulling Jacob towards me and introducing
him to Lisa. Jacob seemed in a daze.
“Hhhhi Mrs. Kudrow,” Jacob said with a shaky voice. His arm
was shaking as he offered it to her. Lisa shook it
vigorously. They were both about the same height, but
Jacob’s massive size seemed to dwarf Lisa, as was evident
when his hand virtually covered hers during their
“Lisa, please. Just don’t call me Phoebe,” Lisa said,
Jacob laughed tentatively and smiled at her. “Ok, Lisa.
Dean was really nice for letting me come along to see the
shoot. I never imagined you would be here. I just wanted to
say though since you are the most famous person I have ever
met and will probably ever meet, that I am a HUGE fan of
the show. All of my friends watch it too,” Jacob said, his
voice much more stable now.
“That’s great. We need all the viewers we can get, what
with Survivor and all the bimbos on that show stealing away
our ratings share. Especially that girl Elisabeth. Where do
they find toothpicks like her?” Lisa said in a half joking
I was about to say something when Jennifer walked out.
Wearing a black midriff tank top and obviously no bra (it
was pretty cold in the room), for her nipples poked against
the fabric of her shirt. She was also wearing a pair of
vinyl hot pants, and every guy in the room couldn’t help
but stare at her as she walked in. Her brown hair seemed to
blow in it’s own wind as she walked in, and it was all
tousled in different ways. Anything to avoid that “Rachel”
hairstyle that was so popular when Friends first came on.
Jennifer saw me and ran over. We hugged and I basically
gave her and Jacob the same introduction I had given with
Lisa. Jacob seemed to be much more at ease now, very
comfortable around the two beautiful celebs. Still, he
seemed sort of awestruck by the whole thing. We didn’t get
to talk long, because the photographer was anxious to get
the shoot started before it got too late in the day.
Very professional and knowing exactly what to do, Jennifer
wasted no time posing for the photographer. She seemed very
much at ease, and looked to be having a lot of fun. Lisa,
Jacob and myself just watched from afar, with Lisa making
the occasional joke about Jennifer that caused both of us
to laugh and Jennifer to give us a disapproving glare.
Gradually though, the poses Jennifer were doing got sexier
and sexier, and the spaghetti straps on the midriff seemed
to slide down her arm more and more with every shot. I
glanced over at Jacob and saw that he was breathing very
shallowly, and I knew that he would very soon have a bulge
in the front of his pants. I could tell that he was trying
to hide it by shifting his position and adjusting the belt
on his pants.
Lisa picked up on this too, but she reacted in a different
way. We were standing sort of off where the shoot was
taking place so that only someone looking would be able to
see us. Reaching down her hand slowly, acting as if she had
no idea what she was doing, Lisa slowly slid her hand down
Jacob’s hip and thigh and let it rest on his growing bulge.
I was watching all of this out of the corner of my eye, and
I could have sworn that Lisa squeezed him gently at least
Jacob was either scared or excited or just plain confused,
because he stood there like a slack-jawed idiot and gasped
rather loudly when Lisa touched him. She made no effort to
move her hand, instead just keeping it resting there on his
manhood. At first I had thought about looking over at Lisa
and signaling for her to stop, but I knew that would be no
help to any of us. Lisa and Jacob were both horny and
nothing I could say would get them to stop (never mind the
fact that Lisa was married).
Just when things seemed to be heating up in the whole
place, the shoot was over. Jennifer walked quickly back to
the dressing room, but motioned for me to follow her. I
took a step forward and turned around to look at Jacob and
Lisa. Lisa just smiled at me and wrapped her other arm
around Jacob’s chest, resting her head on his shoulder.
“Don’t worry, we will be fine. Go see what Jen wants,” Lisa
said. Jacob just stared vacantly ahead and nodded.
I shook my head and walked away to follow Jennifer.
Knocking on the door to her dressing room, I could hear her
voice say “Just a minute.”
I shifted on my feet and tried to put on my business face,
but what Lisa and Jacob might be up to was at the forefront
of my mind.
Opening the door with cigarette in hand, Jennifer smiled
exuberantly when she saw me and wrapped her arms around me.
I personally detested most smokers, but many of the celebs
I had seen smoking a cigarette, they had made it look so
damned sexy. Jennifer was no exception. No wonder the
cancer sticks had held such a smooth image for so long.
Walking into the dressing room, Jennifer had changed and
showered, her hair up in a white towel and her lovely body
wrapped in a pink kimono. The whole room smelled like smoke
and I saw an ashtray filled with cigarette butts on the
table. Finishing her cigarette with a long, slow drag,
Jennifer looked at me and said:
“What the hell was Lisa doing out there? I looked over and
she had her hand on your brother’s crotch! Is there
something you are not telling me?” Jennifer said with a
frown on her face.
“I was wondering the same thing!” I said. I was just as
surprised as Jennifer was, especially since she didn’t know
anymore than I did.
“She’s acted like this before. Once I accidentally walked
in on her and one of the stage hands while we were filming.
There were literally 200 people nearby and she decided she
HAD to get fucked then and there. More guts than I would
ever have,” Jennifer said.
“But you know…” Jennifer continued with a devilish smile
“I couldn’t help but get a little turned on watching her. I
leaked a little pussy juice down my leg watching them,
that’s why I had to take a shower,”
I couldn’t believe how frankly she was talking to me about
her sexuality. I was torn between telling her that I too
was getting aroused but more by her than by what Jacob and
Lisa were doing. Still trying to hold restraint over
myself, I played off the comment by clearing my throat.
“So uhh…speaking of romance, how are things with Brad?” I
Jennifer gave me a sarcastic look, obviously seeing through
my weak attempt at changing the subject.
“Brad and I are fine marriage wise Dean, thank you for
asking,” Jennifer said. “But I have to tell you, he just
doesn’t satisfy me sexually. His cock is only 5 inches! I
thought I would get used to it after a while, but a girl
just needs a good rutting every now and then. Don’t you
think?” Jennifer said sultrily. She had been walking
towards me as she said this, and now I was back against a
wall, fighting every urge not to just go for her. It’s one
thing to go after a young, single celeb but a married one
is a whole new ball game ESPECIALLY when the husband was an
Jennifer’s face was now just an inch from mine, and I could
feel her warmth breath on my lips.
“You know who had a big cock though? Your father. Damn I
miss him, and his meat,” Jennifer said, her light blue eyes
staring into mine. I was still reeling from the dirty talk
she was giving as I tried to decide how far I
was going to let this thing going. “Let’s see how his son
measures up. I’ve wanted to do this since I first saw you
at your father’s funeral.”
Jennifer reached her hand down to my zipper and took it
between her fingers. But she paused. Holding my zipper in
her hand like that was torment enough, but her body and her
breasts, straining against her pink kimono were pressing
against my chest and I could feel her hard nipples jutting
into my chest. I was in shear agony at this point and the
moment I was going to lift my hands up and grab her and
kiss her deeply, Jennifer stepped away, a confused and hurt
look on her face.
“What the hell am I doing? I can’t get involved with you
Dean, I’m married!” Jennifer said to herself, covering her
face with her hands. Jennifer looked up at me with tears
in her eyes. “I’m sorry Dean, I led you on! I shouldn’t
have done that. Can you forgive me?”
I wasn’t sure what to think. I was just a few seconds away
from grabbing her and making love to her and yet now it
wasn’t going to happen, like the whole idea had disappeared
into thin air. I had to act professional so I said “Don’t
worry about it. You got caught up in the heat of the
moment. I forgive you.”
Jennifer smiled and looked relieved. She gave me a hug and
whispered “Thank you” in my ear.
I was relieved that she wasn’t too upset, but still a
little shaken at how turned on I had become.
“Come on Jennifer. Clean yourself up and meet me and Lisa
outside. Let’s all go get dinner,” I said.
Jennifer nodded and then turned around and walked over to
the couch to get her clothes on. I took that as my cue to
leave, and walked outside to find Lisa and Jacob.
The set had emptied out, and other than a janitor sweeping
up, there was no one around and the room had gotten pretty
dark. I scanned around, trying to find Jacob & Lisa. Then,
I heard subtle moans coming from way off in a corner, which
sounded like it was coming from behind the backdrop for the
Tiptoeing over there, a part of me already knew who it
would be and what was going on. I snuck as quietly behind
the backdrop as I could and peeked around the corner to
Lisa was on her knees and had pulled her hands up to her
breasts so that it looked almost as if she was in the fetal
position. Jacob was sitting on the floor with his legs
spread out around Lisa, with his pants at his ankles.
Lisa’s head was bobbing up and down on top of Jacob’s lap,
and the distinct sucking noise that could only be a killer
blowjob could be heard.
I heard Jacob moan softly, a deep, throaty moan. Lisa’s
long blond hair was over her shoulder and I had a great
view of her cheeks bulging in and out as she sucked and
licked up and down Jacob’s cock. Jacob reached his hand
over her shoulder and began to fondle Lisa’s ass, running
his finger along the cleft of her crack. This caused Lisa
to moan in pleasure softly as her mouth remained busy on
top of his cock. After being teased all afternoon by
Jennifer, I quite easily got an erection again, and I began
to slowly stroke myself through my pants, keeping pace with
Lisa’s bobbing head.
Jacob must have been extremely close to orgasm when I began
my voyeuristic little peek, because now his hand moved from
Lisa’s ass up to her head as he guided her up and down and
side to side over his cock. Lisa sucked with all her might
as Jacob began to buck his hips up and down, slamming his
cock further and further down Lisa’s throat. With a stifled
grunt, Jacob threw his head back and unleashed his load
deep into Lisa’s mouth. Lisa swallowed what she could like
a champ, but I saw a sizeable gob leak out the corner of
her mouth and land with a splat onto Jacob’s leg.
I felt myself about to shoot my own load into my pants,
when suddenly I felt a tap on the shoulder and heard
Jennifer say “Dean? What are you doing?”
My hand froze and I turned around with what had to be a
wild-eyed look on my face, like a kid who was caught doing
something he wasn’t supposed to. My hardon was painfully
visible through my pants, but I straightened up and hoped
Jennifer didn’t notice.
“I was uhh… just looking for Jacob and Lisa. I thought
they were back there maybe,” I lied. I heard rustling of
clothes and Jacob zipping up his pants from behind the
backdrop, and then I heard footsteps as the two ran from
behind out the other side of it.
Jennifer gave me a disbelieving look, but it must have not
mattered that much to her because her face shifted to a
smile and said “Well, alright.
Let’s just go find them.”
We walked about 10 feet when suddenly Jacob came running up
right in front of us, out of breath, his hair a sweaty
“Sorry about that, we were just looking around this place
while we waited on you Jennifer,” Jacob said with a smile.
Lisa came running up behind him, giggling like a
schoolgirl. There was still a little bit of cum on her
cheek and I made as subtle a motion as possible towards her
to wipe it off. At first she gave me a puzzled look, but
then quickly caught on and rubbed her face with her right
My gesturing had caught Jennifer’s attention but when she
spun around to look at me, I was all smiles and played off
the hand signal I was giving by running my hand through my
“Well, here they are,” I said.
Jennifer seemed satisfied that we had found them so we all
headed out of the building. Getting into two cars, Lisa and
Jacob in his 911 and me and Jennifer in her Expedition, we
agreed to meet at an exclusive, private restaurant where we
could eat dinner in peace away from fans of the two ladies.
We arrived at the Silver Bell, an upscale New York variety
restaurant at roughly the same time. Getting out of the
car, it was now Lisa whose face was sweaty and her hair all
messy. I could only guess what went on in the car on the
30-minute drive over there. Jacob just gave me a sly grin
and we walked in to the restaurant.
Taking a booth in the back with a big, heavy curtain pulled
around our booth, we had total privacy, except for the
occasional waiter. Jacob and Lisa sat extremely close to
one another in the rounded booth while Jennifer and I sat a
sizeable distance from each other. I think she was still
freaked out about what had happened in the dressing room.
The waiter came and took our order and we all sat there
talking quietly. Well, Jennifer and I were talking
quietly; the conversation was occasionally interrupted by
Lisa jumping up in a start as she giggled, while Jacob sat
there laughing and grinning. When I “accidentally” dropped
my fork on the floor and bent down to pick it up, I saw
that Lisa’s legs were spread and the dress she was wearing
was up around her hips. Jacob’s hand was busily teasing
around her pussy, occasionally slipping a finger into her,
which is what I guess caused her to jump and squirm so
much. The two of them were like teenage lovers, exploring
sex for the first time and loving every minute of what they