Celeb Tour ’99–featuring Britney Spears,
Jennifer Love Hewitt, and many more
By [email protected]
This story is about two friends who go on a summer road trip
and the sexual adventures they have
with some hot celebs. I know that some stuff might not make
sense but its just a story so relax.
For my other stories, an illustrated
version of this story,
xxxcelebs mailing list, and a chance
to be in a Phreak921 story visit
Tommy approached the door of Meg’s room. It was the beginning
of the summer, school had
only been out for a day. The sixteen year old was already
bored out of his mind. But at least
his best friend Meg was just as bored. Tommy opened the door
and entered her room.
Meg was lying on her bed with her eyes tightly closed
completly naked. She was finger
fucking herself. Tommy was extremly aroused but not at all
surprised. He and Meg were very
honest about everything to each other. Meg had masturbated in
front of Tommy before. She knew it
really turned him on and it turned her on too. The two were
comfortable that they sometimes
even took showers together. The one thing that they were not
honest to each other about was how
much they really wanted each other. Tommy sat down on the
edge of the bed, trying to hide his
hard-on. Meg stopped masturbating and opened her eyes.
"Forgot to lock the door." He said. Meg quickly noticed how
turned on Tommy was. She
wanted to take his cock in her mouth but they’d been friends
for so long she didn’t know how he’d
react. She put her clothes on.
"Sorry. I didn’t expect you for like another hour." She
"Yeah I know but theres nothing to do…other than that."
"It’s gonna be a long summer." She said. Tommy turned on the
small television in Meg’s
room. A Britney Spears video was on. This did not help to
reduce Tommy’s erection. But suddenly
a thought popped into his mind. Meg and him had just gotten
their drivers licenses and they had
the whole summer and lots of cash (Tommy’s parents were rich).
"Hey I got an idea," Tommy said, "We could go on a summer road
"Yeah that sounds fun. But i’m sure we’d just get bored of
driving around all summer."
"Well how about during this road trip we try to see how many
celebrities we can fuck."
"Sounds good." Meg responded. They spent a few days working
out all the details. Finally
it was time to leave. They got in Meg’s van and began their
journey. Their first stop was at a
Britney Spears show in NYC. She was the one who gave them the
idea so she was going to be their
first fuck. Once they arrived where she would be playing they
went to the back door. It was
guarded by three big security guards. Meg could take care of
them. Meg flirted with the guards for a few minutes before she
finally talked them into letting
her and Tommy backstage in exchange for a blowjob. She wasted
no time and dropped to her knees.
She unzipped one of the guards pants and pulled out his
already hard dick. She began to suck on
it right in front of Tommy and the other two guards. Tommy
had seen Meg naked and
masterbating before, but he’d never see her do anything with
anyone else. He got immediatly
hard. While she was giving head to one of the guards she took
the other two and began to jerk
them off. One shot his his load all over her shirt and the
other guy followed shortly after.
The guy in her mouth was begining to moan and tense up. He
shot his load down her throat. Meg,
being the good cocksucker that she is, swallowed it all.
Now they were backstage. Tommy felt a bit overwhelmed by
being in this off limits area.
He also had a raging hardon after watching Meg suck dick. She
was also feeling pretty horny.
Both of them were really hoping Britney would want to do this.
They walked down a few hallways
looking for her dressing room. Finally they found it. One
little door stood between them and
sex with a pop star. Tommy knocked.
"Who is it?" A voice from behind the door asked.
"Umm we’re here to see Britney." Meg responded. Britney
answered the door.
"Well here I am." She said.
"Hi i’m Meg and this is my friend Tommy. This is gonna sound
really weird, but do you
"Yeah sure. I don’t really get laid too much while i’m on the
road. I could use a good
orgy." Britney responded.
They all entered her dressing room. As soon as the door was
shut Britney kissed Meg on
the lips. Tommy’s dick was begining to hurt it was so hard.
He took off his clothes and
approached Meg and Britney. Britney took his dick in her hand
and began jerking him off. She
was really good with her hands. Meg’s tongue intertwined with
Britney’s as she massaged
Britney’s perky tits. Within seconds all of them were naked.
Britney stopped kissing Meg so
that she could take Tommy’s cock in her mouth. His cock slid
easily down her throat. While
Britney was sucking, Meg bent down and licked at his balls.
Tommy began to freak out. It was
too good having Britney Spears and his best friend both giving
him a blow job at the same time.
"Ohh shit i’m gonna cum." He yelled.
"No don’t, its been a long time since i’ve had a nice cock
inside me." Britney said.
Tommy layed down on the couch and Britney mounted him. She
slid his dick deep inside her
and began to fuck him. While she was bouncing up and down on
Tommy, she started to eat out Meg.
Britney’s cunt was really nice. She felt great, easily the
best fuck Tommy had ever had. The
sight of the teen star enjoying his cock while going down on
Meg was too much. Tommy began to
scream as he shot a load deep inside Britney. The feeling of
his cum being shot inside her made
Britney come to a quick orgasm. She began to lick and suck at
Meg’s pussy with intense passion.
Meg was soon screaming as well. All three rode out their
incredible orgasms before collapsing
onto the couch.
Tommy and Meg got dressed after a few minutes and left.
Britney thanked them for the great
fuck. They left the building and got back in their van.
"One down." Meg said as they sat in the parked van.
They now had to decide where to go next. They looked through
a newspaper and discovered
that Leelee Sobieski was in town doing some publicity. It was
late and they were tired so
they decided to get some sleep and head to the set tomorrow.
They figured it would be cheaper
to just sleep in the back of the van so they rolled out two
sleeping bags and got ready for bed.
Meg removed all of her clothes. She put them in a pile in the
corner of the van. When she
turned around she noticed that Tommy had a huge hard on.
"Wow Tommy why so excited?"
"It’s just that you have an amazing body." He replied. "I
never realized I turned you on that much."
"Well you do."
"Do you want some help getting rid of that thing?" She asked.
Meg took Tommy’s pants off and took his big cock into her
mouth. She twirled her tongue
around the shaft and began moving her head back and forth.
She could suck dick really good.
Tommy couldn’t last more than a second because she was too
good. He exploded in her mouth. She
swallowed it all.
"Your really good at that." He said.
It had been a busy day so they both feel asleep pretty fast.
The next day Tommy woke up
early. He looked around the van and quickly came to the
realization that Meg was not there. He
panicked for a second. Where could she be? But before he
could totally freak Meg opened the
van door holding two cups of coffee and a bag of donuts.
"Thought you could use some breakfast. We’re gonna need lots
of energy for today." She
Tommy and Meg ate their breakfast then headed for the NBC
building. Leelee was going to
be on Conan ‘O Brian. Once again they found the back door.
Tommy was suprised to find that
there was no security guarding it. They walked right through
it and into the halls of the NBC
building. Everyone around them was so busy preparing things
for the various shows taped there
that no one realized they weren’t supposed to be there.
Eventually Meg and Tommy found their way into an empty studio.
This was definatly not the
Conan set. There were little pieces of scenery everywhere.
Meg recognized a few of them. They
were in the Saturday Night Live studio. Tommy happened to
remember that Natalie Portman was
hosting that week. They returned to the busy hallways,
looking at every door until they saw one
with a big star painted on it.
They knocked. No answer. They entered the room to find
Natalie asleep naked on a couch
in the dressing room. Meg tapped her on the shoulder.
"Hello Natalie." She said.
Natalie woke up, saw Tommy and Meg standing there looking at
her and she freaked. She
jumped to her feet, trying to cover herself up with her hands.
"Who are you? Why are you here?" Natalie asked franticaly.
"I’m Tommy and this is my friend Meg. We don’t mean any harm.
We’re just big fans."
"Do you want some autographs or something?"
"No actually we’d like to give you something." Meg said. She
dropped to her knees in front of Natalie. She looked a
little stunned at first but
as soon as Meg’s tongue made contact with her young pussy lips
a smile crept across her face.
Tommy went to work on Natalie’s upper half, sucking and
nibbling on her small yet firm tits.
Natalie’s juices went all over Meg’s face as she continued to
eat her out. Natalie was in pure
bliss. This was the most incredible orgasm the teen had ever
felt. She began to let out a
scream but remembered that she was in a TV studio. Tommy saw
her about to scream and kissed
her. He could almost feel the orgasm she was having through
the wild movements of her tongue in
his mouth. He unzipped his pants and let them drop to the
floor. Meg stopped working on
Natalie’s pussy. Tommy lifted Natalie up and slid his dick
into her. She was now suspended in
the air getting impaled by Tommy. She bounced up and down on
his dick. After about five
minutes of this Tommy coulden’t hold her anymore so he layed
her down on the floor. Meg had
taken off her clothes while Tommy was fucking the shit out of
her. She got down on the floor
on top of Natalie and the two girls began to make out. As
they kissed, they began to grind
against each other hard. Their juices mingled and their
bodies became one. Meg opened her eyes
for a second and looked into Natalie’s. They were the most
beautiful shade of brown she had
ever seen. In that moment both girls saw something in each
other. For a brief second they
shared both mind and body as an incredible orgasm made both of
them twist and moan together on
the floor. Meg rolled off of Natalie and fell next to her.
Both of them took deep breaths as
"Hey Meg I’m gonna go find the other person we were here to
see. I’ll meet you back in
the van later." A now fully dressed Tommy said.
"Ok bye." She responded. Meg didn’t want to move. She was
gonna have a little more fun
Tommy left the dressing room and headed back into the busy
hallway. He found a staircase
and went up to the next floor. His heart skipped a beat as he
realized that he was on the same
floor as Leelee Sobieski. He had had sex with two hot teenage
celebs over the past two days and
yet he was still really excited at the chance of being with
Leelee. He was also nervous. This
was his first encounter where he didn’t have Meg by his side
to help him. At least he had just
had his dick inside the cunt of Natalie Portman, so even if he
coulden’t fuck Leelee he had
already seen some action that day.
This hallway was just as crowded as the one on the Saturday
Night Live floor. This
building had a very confusing layout so it wasn’t easy to find
his way to Leelee’s dressing room.
Tommy found a set of big doors and went through them. He was
now on the Conan ‘O Brian set.
A little tired from earlier, he took a seat behind Conan’s
desk. Suddenly it hit him that he
was sitting in the chair where he saw his favorite talk show
host sit every night. He began
imagining himself as a late night talk show host. He was so
busy daydreaming that he didn’t see
the girl approach him from behind.
When she tapped him on the shoulder he almost fell over. He
thought that he’d been caught
and was going to be arrested. He turned around and his panic
disappeared. Leelee Sobieski was
standing behind him.
"Hi," She said, "I’m Leelee."
"Ummm hi." Tommy’s face was bright red with embarassment.
"Don’t worry I was doing the same thing myself before."
"Yeah, Its a little wierd to be on all these shows. I mean
I’m just a normal girl."
"I was gonna say ‘I know what that’s like’ but I have no
idea." Tommy said.
"I’m just like anyone else. I eat, I drink, I go out with my
friends, I fuck cute guys in
"What was that?" Tommy thought he was hearing things. "You
Leelee kissed him. Tommy instantly got hard. He didn’t come
in Natalie and he really
needed to. Leelee was anxious for a fuck herself. Within
seconds they were both naked. Tommy
layed her down on the desk. His dick ached for her and her
cunt grew hot and wet awaiting him.
He slid his cock inside the girl’s tight pussy and began to
fuck her. She let out a slight gasp
as he pushed all the way inside her. Her tits were hard and
Tommy attended to them, sucking and
nibbling like he had to Natalie before.
"I like it hard." She said.
Tommy began to thrust into her with as much force as he could.
Before long Leelee was
screaming in ecstacy. Her body was perfect in every way.
Tommy was having a hard time not
cumming. He devoted every muscle in his body to fucking her
as hard as possible. She was the
best fuck he had ever had. She was having just as much fun.
Leelee was having multiple orgasms
as Tommy’s dick pounded at her soft tight cunt. She began to
thrust her hips to meet his cock
at every thrust. They were in perfect synch.
"Oh god yes, fuck me," Leelee screamed, "Fuck me up the ass."
Tommy pulled out of her perfect body and turned her over. She
was now bent over the edge
of the desk with her ass facing Tommy. This was too perfect,
he thought to himself. He pushed
his cock into her tight anus. Her muscles squeezed his dick.
It felt better than anything he
had ever felt before. It took him a few thrusts to loosen her
up a little. After that he was
back to fucking her harder than before. She was screaming and
moaning loudly as he pounded
away at her great ass. She threw her head back and let out
continuous moan as the greatest
orgasm she had ever felt hit her. Her anus muscles tightened
up. It was too much for Tommy.
He shot a huge load deep inside Leelee’s ass.
Both of them quickly got their clothes on and left the studio
before the audience arrived.
They made out one more time outside Leelee’s dressing room
before they parted ways. She had to
get ready for the show. Leelee gave him a ticket to sit in
the front row during the show. She
told him that she was gonna give him his own private show
during her interview. Tommy left her
and headed into the audience.
He looked at the desk and reflected on what he had just done
on it. Before he knew it the
show had begun. After sitting through a few comedy segments
Leelee was on. She came out
wearing a stunning dress that made the guys (and a few girls)
in the audience go insane. The
interview went pretty normal until she was asked if she was
currently dating someone. She
replied that she wasn’t dating anyone but she had a crush on
someone. Then she smiled right at
Tommy. But that wasn’t enough for her. She then spread her
legs a little giving everyone an
great view of her pussy. She did it so that is seemed
accidental, but Tommy knew otherwise.
After the show was over he decided to head back to to the van
and meet up with Meg. It
had been a great day and he needed some rest. Leelee was
great but he wanted to keep up with
the plan. There was other places to visit and celebrities to
fuck. After stopping for some
dinner he got back to the van. Meg was waiting for him.
"Where have you been?" She asked.
"I got Leelee."
"What happened with Natalie after I left." He asked.
"Oh we just fucked some more. That girl can really eat
pussy." "I can imagine. So where to next?"
They’d both had enough of NYC so they decided to move on.
They started up the van and
began driving. The next morning they pulled up to the gates
of an amusement park. They were
somewhere in Virginia. Meg said she wanted to go on a
rollercoaster so they thought that this
might be a good place to stop for a few hours.
Once inside the park Meg immediatly saw a familiar face. It
was Larisa Oleynik aka Alex
Mack. She had was sitting at a table eating an ice cream
cone. Tommy began imagining rubbing
that ice cream all over her body. He became aroused at the
thought. Meg led him to her table.
Maybe this stop would be better than he expected. Larisa
looked up as they approached her. She
hated being bothered while she was on vacation. She would
have gotten up and ran away but she
coulden’t find anywhere to go.
"Hi. I’m Meg and this is my friend Tommy."
"Are you fans?" Larisa asked.
"Kinda. We were actually wondering if you wanted to have sex
with us." Tommy said.
Larisa was shocked by how foward they were. But they did look
good and she didn’t often
get to fuck in amusement parks so she agreed. The three
hopped on a long calm river boat ride,
kind of a tunnel of love thing. As soon as they were out of
view, Larisa unzipped Tommy’s pants
and pulled out his already hard cock. She bent down and took
it into her mouth. Meg got in
back of her and began to eat her out. Her young cunt was nice
and wet. Meg stuck two fingers
into Larisa’s cunt and used the juices to lube up her ass.
fingered Larisa’s ass as she
lapped at her pussy. Larisa was a good cocksucker and Tommy
was already twisting in his seat as
his balls tightened and he came in her mouth. She swallowed
every drop. They all got their
clothes on just before the ride ended. They then headed for a
Tommy sat between Meg and Larisa. As the ride started he
stuck a hand down each of their
pants. His fingers found their way into both girls moist
cunts. Both of them moaned gently as
the ride went over a few hills. Meg unzipped Tommy’s pants
and began to jerk him off. Larisa
did the same. Tommy now had two hot teen girls jerking him
simutaniosly. He twisted his
fingers around inside the girls eliciting loud screams from
both of them. Between the motion of
the ride and the finger fucking both girls had orgasms rather
quickly and at the same exact
time. Although Tommy had just cum, the feeling of the two
girls pussy’s twitching with their
orgasms and the two hands massaging his cock made him cum once
again. He quickly put his dick
away and they got off the ride.
Meg and Tommy said goodbye to the lovely Larisa and got back
in the van. It was time to
move on. Four down and more to go. They drove for a few days
taking turns behind the wheel
before they finally arrived in Los Angeles. Meg wanted to get
some sleep. She’d been driving
for 24 hours straight. Tommy wanted to go out and see if he
could find some action. He told
her he’d meet her back in the van later that night.
Tommy roamed they streets for a while before he caught his
first glimpse of a celebrity.
It was Jennifer Love Hewitt. But she was with someone. At
closer look she was with Katie
Holmes. The girls walked down the street holding hands and
giggling. Tommy got nervous and was
just going to keep walking when Katie reached out and grabbed
his arm. "Hey your cute. Wanna fuck us?" She said.
Tommy quickly agreed and they led him back to their hotel.
They explained how they had
been having an affair for about a year and they sometimes
liked to get a guy to join in. He
was glad he didn’t stay in the van with Meg. Love pushed him
down on the bed and immediatly
tore his clothes off. Katie and Love did the same to each
other. Katie began to suck on Tommy’s
dick. Her tongue wrapping around the shaft and almost jerking
him off. Jennifer sat on his
face and he began to fuck her with his tongue. It was
amazing. Two hot teen celebs at once.
This was definatly the climax of the trip. Katie’s blowjob
incredible. She was far better
than anyone else. He knew that he’d find himself tuning into
Dawson’s Creek a lot more after
this. He felt himself about to cum so he stopped her.
Katie and Jennifer both lay down on the bed next to each other
and spread their legs.
"Come and get us." They said in unison.
Tommy had had lots of fun with Katie’s mouth already so he
climbed on top of Love and
began to fuck her. Her cunt was nice. He was fucking
Jennifer Love Hewitt. Tommy began to
pump harder. She was moaning and rubbing her tits as he
pounded her pussy. She was enjoying
his cock. Love came to orgasm fast. She let out a scream.
Tommy pulled out of her and
immediatly shoved his cock deep inside of Katie. Her body was
so nice he almost came as he was
pushing into her. He was able to stop himself and work up a
steady rythm. Katie had never had
a dick as big as Tommy’s and she began to scream in pleasure.
Tommy had had enough. She was
way to good. He was gettting very close to cumming when Katie
pushed him onto his back and
straddled him. She began to ride his cock, bouncing up and
down as fast and hard as she could.
Her small tits bounced as she yelled.
"Oh yeah i’m gonna cum!!!" Tommy screamed.
Katie jumped off of him and caught the load of jism in her
mouth. Love joined in and both
girls licked his cock clean. They later told him that he was
the best fuck they had ever had.
Tommy left the hotel after recovering for a few minutes and
headed back to the van. When he
opened the door he saw Meg with her head in some girl’s pussy.
When the girl turned around he
saw that it was Kirsten Dunst. He was too tired to join in
but he watched as Meg and Kirsten
69′d. Both girls moaned and screamed as they had orgasm’s.
Kirsten stared at Tommy and
imagined him fucking her. Finally both girls got tired and
Kirsten left. She gave Tommy her
number, in case he was ever back in town and wanted a little
fun. The next morning Meg and Tommy headed back home. It had
the trip of a lifetime and
neither of them were going to forget it. They knew that
probably never see any of their
famous partners again but they hoped they would. On the first
day of school Meg slipped a note
into Tommy’s locker. All that was written on it was "NEXT