Chicago Escorts For Hire

"Chicago Escorts For Hire"
by CoolAl27

WARNING: This story contains adult material not suitable for minors
or immature minors. If you are under 21 and cannot handle this,
please do not read further.


The skinny, brown-haired girl entered the hotel with sunglasses and a
hat trying not to be seen as the big celebrity she was. She was
wearing a t-shirt that was purposely two sizes small and tight jeans
that showed off her teenager ass teasing any guy who walked by. She
walked to
the lobby elevator, waving goodbye and calling out to
Jennifer Love Hewitt, who had gave her a ride to the hotel.

"All right. I’ll see ya later," said the voluptuous
teenage girl.

As the elevator bell rang, the girl went to her hotel room and
immediately went to lay on her bed and turned on the TV, exhausted
from her hard day’s work. Upon closer look, this girl was no
girl, she was the beautiful Lacey Chabert from Party of Five and Lost
in Space. While watching the TV, she ran her fingers through her hair
wondering what she wanted to do tonight. A commercial came on, and
she called Jennifer Love Hewitt, who she had became friends with ever
since she started Party of Five.

"Hello. This is Lacey. Is `Love’ there?"
"This is she. Hi Lacey, I didn’t expect your call! What’s
going on?"
"Nothing much. I was just wondering, I’m not doing anything
would you like to see that new movie that just came out?"
"I’m sorry Lacey, I’m seeing a friend of mine tonight.
"Bummer. All right, see ya tomorrow at the airport."

Lacey finished the conversation with `Love’ disappointed.
wondered what she was going to do tonight in the Windy City, because
it was her last night taping Party of Five on location, and tomorrow
they were going back to Los Angeles, and Lacey wanted to make this a
night she’d never forget. As she racked her brain, thinking of
to do, another commercial came on that caught her attention.

"Are you bored? Do you want to have a night on the town
you’ll never
forget? If so call my number and I’ll show you a tour of the
City and dinner for a low price. Call the number now at 1-800-CHI-
TOWN for Joe’s Escort Service." the commercial quipped.
"Hmm. That sounds cool," Lacey said as she looked for the

Lacey dialed the phone quickly, almost making a few mistakes with the
number. The man in the commercial, who she thought was pretty cute
too, intrigued her.

"Hello Joe’s Escort Service, can I help ya?" the Chicago
accent voice
"Yeah, I saw your commercial and I’m interested in seeing the
Lacey replied.
"Ok, uh what time would you like me to meet you? The supper that
comes included takes about an hour, and the tour of the town takes
about an hour also."
"Hmm. How about 9 o’clock? Could you see if I could meet that
guy in the TV commercial?" Lacey asked hopefully.
The man on the phone laughed.
"I am that guy you saw in the commercial, I’m Joe. I’ll
be glad to
escort you, you’re very nice. I’ll need your name and your
for the reservation."
"My name is Lace-," she stopped in mid-sentence trying to
think of a
different alias. If the tabloids had heard the young and innocent
Lacey Chabert was with an escort they’d rip her to pieces with
"My name is Lucy O’Dell. I’m at the Chicago Hilton, in
Room 1202. I’m
not sure what street the hotel’s on. Is that ok?"
"Oh ok. Yeah sure that’s fine, I know where that is. I’ll
see you
about 9:00 PM tonight, Ms. O’Dell."

Lacey hung up the phone with Joe and was eager for tonight’s
"Oh my god! What am I going to wear?"
Lacey raced to her closet wardrobe looking for something classy and
pretty for the special occasion.

On the other end of the phone, Joe looked through his appointment
book, about to write down the appointment with Ms O’Dell.

"Oh man! I double-booked again. That girl does sound excited
Chicago and I’d hate to disappoint her. Ryan? Ryan come here, I
got a
job for ya and there’s some money for ya if you do it right."
"Yeah dad, what is it? Do I have to wash the car again?"
"No, it ain’t that. You know how I always tell ya that
I’d like you
to carry on the business when I retire?"
"Yeah. So what does that mean to me?"
"Well I double-booked again, at 9:00 I’m supposed to go with
Jennifer Love Hewitt who’s taping that show of hers and I
this, uh, Lucy O’Dell I’d give her a tour of the town. So are
you up
for it?"
"Yeah. That beats sitting around here all day."
"Oh yeah, take some money and dress nice, will ya? Last time you
almost scared off a customer. You kids have no respect…." the
man rambled on and on.

It was 8:50 PM, and both Lacey and Ryan were nervous about meeting
each other. Ryan was hoping that Lucy was good-looking and hopefully
get some action too. Lacey, on the other hand, was dressing up as
much as she could, definitely a twist from her usual clothes. She had
chosen a tight silk black dress and decided to show off her teenage
cleavage and not wear a bra. The fabric of the dress was so smooth it
was making Lacey’s tiny teenager nipples hard and making her wet,
she was hoping that this escort was a stud because she was so horny.

Lacey started getting hornier and she rushed to her suitcase where
she had secretly put her new toy. She grabbed the toy and started to
turn herself on, she started massaging her tits and brought one up to
her mouth and she started to suck it biting the nipple. She took the
vibrator and teased her pussy exposing the clit, then slowly moved
into her pussy, which was easy because it was well-lubricated. She
started shoving the vibrator in and out, almost shoving the 8-inch
vibrator all the way in.

"Oh YES! OH OH OH UH UH UH ohmygodohmygodohmygod!" Lacey
screamed as
she had her orgasm and her juices flowed out of her onto the bed
making a huge puddle. She dipped her finger in the puddle, trying to
get all of her cum she could, and brought it up to her mouth where
she licked it slowly and enjoyed her sweet cum, which tasted so sweet
and enjoyed it like a connoisseur.

"Mmmmm, I love cum!" she said with her mouth full trying not
to spill

A knock at the door came, making Lacey startled as she was still
enjoying her cum. She cleaned herself up, put on her clothes, turned
off the TV, and opened the door, with the chain still attached.

"Hello, can I help you?"
"Yes, I’m your escort for tonight. Joe had something
important come
up and I’m here instead of him. If it’s ok with you, are you
for your `night on the town’? Wait…I’ve seen you
somewhere before,
where was it? Oh yeah, that Lost In Space movie, you were good in
"Well thanks, I’m always happy to meet my fans. I have to
make up
fake names `cause I’m a celebrity and all. I’m ready if
you are."

As Lacey grabbed a little black purse, she was thinking about Ryan in
the nastiest way. He had that nice brown hair, a rounded face with an
innocent look on it, nice muscles, and she noticed that he had a
large bulge in his pants. They then proceded to Ryan’s car in the
garage. Ryan and Lacey were in the car and drove down to the
restaurant and throughout the meal they talked about school, boy and
girlfriends, and current events. About 2 hours later they finished
their meal and got in the black Lincoln that Ryan drove as the
business car. Ryan was worried the whole time, thinking that Lacey
might see the huge bulge in his pants. For the first time, he met the
girl who had gave him something to think about. They both took a tour
of the town, Ryan pointing out all the landmarks of Chicago and
later, to Ryan’s disappointment, it was getting late. It was
11:30 as Ryan parked the car and he was taking Lacey to her room as
they waited on the elevator.

"So did you like tonight?" Ryan wondered.
"Yes I did, it was wonderful, especially with a nice guy like
Lacey teased. Lacey was trying to get this guy really horny for an
all-night fucking which she wanted real bad. Being on the road, she
didn’t have as many toys and she was depraved from having any
and tonight, she wanted Ryan’s. Then at the door Lacey dropped

"Oh dear!" Lacey bent down as she purposely went slow to pick
things up, as she bent over to Ryan, showing her revealing pink
panties with lace, making Ryan’s bulge grow as Lacey giggled to
herself quietly Lacey picked up the keys and unlocked the door. She
was going slow wondering what to say to Ryan.

"Hey Ryan?
"Um, I think there’s something wrong with my bedspring."
"Alright I’ll take a look at it…if that’s
"Yes, that’s fine, c’mon in."

"I’ll be back in a second."
"Ok," said Ryan struggling to find the problem and not look
like an
Lacey grabbed some clothes out of the closet and went in the
bathroom. She had picked out some revealing panties and matching bra
that she got from `Love’ as a birthday gift that was from
Secret. She put on the tight bra and panties that showed off her
cleavage and her ass more than the dress. As she walked out, she
loved the idea of being a slut, and every time she took a step the
fabric rubbed against her, turning her on more and more.

"Hey Ryan," she said seductively, "I think there’s a
problem here."
Ryan turned around casually and was in awe at the sight of this sexy
celebrity in the hottest lingerie money could buy.
"The problem is, I really want you. I want you here and now."
"Well I think I can fix that, Lacey."
He approached her and kissed her softly, creating a small moan from
Lacey. He brushed her hair back as he explored her mouth with his
tongue. Lacey was moving her hands up and down his body and had
reached his cock and felt the mountain growing from Ryan’s pants.

"Well, someone’s horny, aren’t they?" Lacey said as
she massaged the
area of the jeans.
"Well what do you call these?" Ryan said pointing to
Lacey’s nipples

Ryan carried her to the bed sitting on their legs. He took off her
pink bra looked at them hungrily, licking his lips. He then grabbed
one of her breasts rubbing slowly her nipple between his thumb and
finger, at first very slowly, but gaining speed getting her nipples
real hard, very quickly. With his other hand he pinched her nipple,
and Lacey cried out in ecstasy wanting more and more arching her back
with pleasure.

"OH Ryan! Do that more! You’re driving me wild! Give it to

He wrapped his arms around her feeling her ass up and down, feeling
the soft silky skin of the famous celebrity. Ryan then switched to
her other tit doing the same thing except now he was flicking her
nipple with his tongue, which gave Lacey so much pleasure that she
thought she was going to have an orgasm right there and then and
spoil all the fun for later.

"No, hold on, same some for later. Oh my god! That was sooo good!
C’mere and let me reward you," she panted heavily.

Lacey pulled him closer kissing him and moving their tongues all
around exploring each others mouths romantically. As they were doing
this, Lacey unbuttoned his shirt slowly and erotically, and felt his
chest and held him tight, trying to push his bulge as far up against
her as she could, rubbing up and down on it getting Ryan so hard, he
thought he would explode. Then she erotically unzipped his pants
releasing his cock and Lacey got wet and could feel the heat inside
her grow, wanting to have his large cock inside her.

She then grabbed his cock, and wrapped her hands all around it. She
then started to move them up and down, jacking Ryan off. Ryan was
leaning back in pleasure and was feeling his explosion rising. As
Lacey jacked him off, she knew what was coming soon, and then Ryan


Lacey had a little cum land on the sides of her face and aimed the
exploding cock in her mouth, gulping all of his seed. Ryan got limp,
but then she started to tease him just licking at the tip and
underneath his cock, which started to get Ryan hard quickly. She then
slowly enveloped all of Ryan, swishing his cock with all her saliva,
sucking him as hard as she could and fondling his balls with her free
hand. She was twisting and turning her head trying to get every piece
of Ryan into her mouth, even though he was huge, she was moving her
head back and forth on his cock while Ryan tried pushing her head
further and further onto him. When he warned her about cumming again,
this turned her on again hopefully fulfilling one of her fantasies,
to be cummed all over her body rubbing it all around herself. As she
went faster and faster licking him all over he exploded and Ryan
aimed it at her face and then her tits as the stream of cum kept
going. Lacey took all of the cum and rubbed it all around her body,
especially with her tits.

"Ryan I want more cum, give it to me, I want your seed all over
"You’re a little slut aren’t you, you whore?"
"Yes, I’m a cumslut! Give it to me! Let me jack you off!

She guided Ryan’s dick between her tits jacking him off with
quickly getting cum all over Lacey in which she started spreading moe
around her body slowly. She embraced Ryan and they moved over each
other smooth as ice. They rubbed up and down, and for the first time,
Ryan tasted his own cum, as he licked her clean of all the cum she
had on her body. He saved her tits for last, and he was licking them,
Lacey pointed his head down and he got the idea. He then started
licking her thighs and legs, also not forgetting the feet, which
Lacey had a secret fetish for. When Ryan saw the shaved pussy, he
knew he was in for a treat as he started licking around her and then
nibbling on her clit making her more and more wet. As he was doing
this he was grabbing her ass and massaging her warm thighs which
Lacey was squeezing Ryan’s head in.


Then Ryan started darting his tounge in and out of Lacey, and
occasionally would bite her clit, each time almost sending her over
the edge. He had licked every part of Lacey and inside her he felt
her walls with his tongue as Lacey pushed his head between her legs,
screaming his name. Ryan wanted to get some pussy and take
ass too and he put his finger in her virgin pussy, which caused some
pain to Lacey.

"Ouchhh! No keep going, go slowlyyy…"
"Alright you little slut, you just wait `til I pop your
cherry and
then later…"

Ryan then took out the finger and licked all of Lacey’s juices
was on his finger and licked it clean, savoring the taste of the
sweet cum. Lacey tried putting Ryan inside her but he wanted to tease
her a little more. He then looked around and found the vibrator Lacey
was using and then slowly moved towards her asshole slowly pushing
in, pausing here and there to let her get used to the pain. He knew
she was ready and started pumping it in and out of her asshole as he
slipped the condom on and then popped her cherry in one push.


Lacey was overwhelmed since she never had her ass and her pussy being
fulfilled at the same time. Ryan was puming harder and harder as he
shoved the vibrator in as much as he could and pulled it out, and
Lacey then licked like she was giving it a blowjob. She couldn’t
much more of this double penetration and started shaking as she
convulsed into orgasm screaming and yelling, still jumping up and
down on Ryan’s cock that impaled her.

"Oh Ryan…you’re so good….now shove that big cock of
yours….in my
ass!" she said gasping for air.

Before she could say another word, Ryan took out the vibrator, took
off the condom, and shoved his dick into her even tighter asshole.
She got on all fours and took his cock up her asshole, pushing back
and forth in a natural rhythm, when suddenly he had started cumming
inside her. His warm cum filled her up, and Ryan kept pumping,
knowing she was going to have another orgasm.

"Owwwwwwww, ohhhhhhh, oooooooo! Morrrrrre Ryan, give it to meeee
harderrrr" Lacey tried saying as he started to pump her as hard
as he
could, slamming into her beautiful ass with a nice slap.

He lifted her up and down on his hard shaft moving her up and down as
she screamed at the top of her lungs as she had another orgasm.

Ryan and Lacey kissed and held each other after their wonderful sex,
which they would never forget. Then the happy, and worn out couple,
exchanged phone numbers and e-mail addresses for phone and cybersex
and maybe to meet again, the next time she would be in town and need
an "escort".

Ryan tried sneaking into his house without waking his parents at 3:00
AM. His dad saw him and he knew he was busted.

"Ryan? Did you have sex with that girl I told you to escort?"
"Uh, no Dad, no I didn’t, I sware!"
"Dad, she was asking for it, it was Lacey Chabert!
"If you did that’s ok. I know a little about Lacey’s
friendship with
Jennifer and next time `Love’ and Lacey want escorting, I
have a

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