Shemale Street Hooker
- 2 years ago
- 20
- 0
My Night As A Hooker free porn video
My Night As A Hooker
by Tanya Fly
Comments welcome.
Let me tell you a story about a girl, a cheap motel, the hooker
stroll, and some very sleazy clothes in my size.
Natalie is the kind of girl you see in some rock video or beer
commercial. Great T&A, tall, lots of long blond hair, and a wild,
kinky imagination. We met in the city. I was a junior advertising
"executive" (read go-for) and she was the knockout administrative
assistant going to night school to finish her business degree.
The flashy advertising guys were all over her, but their bedpost
notching reputations preceded them and Natalie politely declined all
overtures and discretely reminded the office wolves of the company's
policy on harassment. These sleazeball advertising guys may lie,
cheat, steal, and cheat on their wives, but even they knew better
than to get pinned with a harassment charge. They deemed her an ice-
queen and some protected their egos by inferring that she must not be
into guys.
As for me, whenever she was around I just avoided even looking her
way. My philosophy is to not even look at something you know you
can't have. I'm not rich, flashy, and was so junior that even the
senior secretaries looked down on me. In fact, I'm kind of short and
a little skinny, but wiry. People have often teased me that I'm too
pretty to be a boy, and that I'd better stay out of prison.
There are many things that I am not at, but I am good at accounting.
That may not be a real turn-on to you, but to a certain struggling
business student with a great rack it was like a magnet. Once Natalie
found out that I'd graduated tops in my class with an accounting
degree, something that came out once I'd hung my diploma over a
strangely colored spot on the fabric of my otherwise
indistinguishable cubicle, she was on me like glue. When I say "on
me", I mean that she asked me lots of accounting questions and had me
review her homework. One thing led to another and before you know it,
we're dating. Turns out that she was just a really cool and nice girl
that was "plagued" with a hot body and great looks.
Guys at work couldn't believe that she would even allow herself to
be seen with me. No one could figure it out. But she was like magic
for my career. The bosses began to notice me since I was "friends"
with the hot admin-girl and before long my responsibilities, title
and pay increased. Oh, I was still plenty junior but at least the
secretaries stopped ordering me around and I had a few extra bucks in
my pocket.
The perks were great, but I would have lived homeless and washed
windows for a living if that it was what it took to continue having
sex with Natalie. Some guys, mostly those who get rejected by women a
lot, think that a pretty girl must be bad in bed. They think a pretty
girl just lays there and relies on her looks, and it may be true in
some cases, but not with Natalie. She was some kind of wild woman.
Took it, gave it, came back for more. Whatever.
Now to my story.
One Saturday night, after aceing her accounting final earlier in the
week, Natalie promised that she had something special planned as a
way of saying thank you for all my help. She told me to pick her up
in my car, a beaten down old wreck that was perfect for the city
since no one would ever steal it, and to plan on a wild night. She
said we were going to somewhere dirty, literally dirty, and to wear
nothing but old shorts and a tee shirt, cheap sandals and to leave my
wallet and money at home. She said that it was better to risk the
cops than to risk having my license and credit cards get lost, or
stolen. I asked a lot of questions, but Natalie didn't answer any of
them. I protested, but she always gets her way and Saturday evening
found us looking like tramps as she drove my car to a really bad
section of town.
It was still light out when Natalie unloaded the overstuffed paper
bag she had brought with her. We had parked in front of a decrepit
old bowling alley, where there were at least a few other cars parked,
the only sign that the place was even still in business. But we
weren't going bowling. Instead we set off up the street, our flip
flops offering bare protection against the broken bottles and
assorted discarded scrap metal that littered the sidewalk. There
wasn't much traffic and only a few, very scary, looking people walked
past us. Natalie just pushed on, very excited.
We walked for about a mile up the strip and by the time we reached
the seedy hotel that rented rooms by the hour, it was pretty dark and
traffic was beginning to pick up. When I say "traffic" I mean guys
prowling in cars looking for hookers. Natalie had me wait outside the
sleazy hotel while she went in to make the arrangements. Apparently
renting a room in this joint didn't require much paperwork since she
was calling me in about a minute, a very scary minute, later. I told
her that we could afford a place a bit better than this, but she
laughed and said it wasn't the price, but the location.
We get to the room which was, to my amazement, even worse than I'd
expected. How the authorities let a firetrap like that stay in
business, I'll never know. It smelled like stale beer and used
condoms. After I finally wrestled the door closed, Natalie was all
over me. Hugging and kissing and generally getting me all worked up.
I thought we are just there to have an unusual sex night, kind of
seedy and slummy and dirty, the way great sex should be, but no.
Natalie breaks the embrace and hands me a razor. She tells to shave
everywhere. "Everywhere?" "Yup, everywhere, neck down." "Even legs?"
"They're below your neck, aren't they?" she says. I say, "What will
the guys think?" She says, "The guys already think you look like a
girl, and besides they aren't here for a special sex night with you
and I am."
Good enough for me.
So I suck it up, go take a shower and shave baby smooth, everywhere.
I get out of the bathroom, which was even worse than I could have
imagined, and find Natalie dressed in some of the sleaziest clothes I
have ever seen. She looks like a streetwalking whore, only like a
beauty queen version of a streetwalking whore.
Natalie runs her hands over my legs and hairless crotch and tells me
that I did a good job and to get dressed. She tells me that my new
clothes are in the bag. I dump them out and find a few scraps of
glittering material that somehow can be configured into a dress,
something that looks like two fake breasts, which do turn out to be
two fake breasts, and a pair of metallic gold high heels. There is
also a blond wig, a cheap purse, lots of makeup, and a few other
necessities.
"Hurry up," she says, "get dressed." I start to protest but she
tells me it'll be fun, and she looks so fucking sexy that I'm pretty
much willing, (who am I kidding), I am very willing to do whatever
she says. She helps me with the stockings and dress and helps me tuck
Mr. Happy into some sort of special underwear that keeps it out of
sight. She also helps me with the fake breasts, makeup and wig. I
catch glimpses of myself in the mirror and I have to admit that I
look pretty good. Natalie wouldn't let me look for long though since
she seemed to be in some kind of a hurry. She kept looking at her
watch and it was obvious that there wasn't much time to waste on
things like hugging or kissing. She was just buckling my heels on
when I asked her what is the big rush.
She said that she only rented the room for an hour and the guy at
the desk seemed to be a stickler for time. The hour was just about
up. "We aren't saying the night?" I asked. She looks around at the
room in disgust and says, "Uch, this place is too gross."
So I asked why we didn't just rent another hour or two, since it
seemed a shame to get all dressed up only to have to take it off
again because the hour was almost up.
Natalie then said: "One, we can't rent more time since we don't have
any more money. (She shows me both of our empty purses, except hers
has a car key and mine has condoms) and Two, we aren't getting
changed back into our old clothes because I cut them up into a little
pile of scraps, even the sandals." (She shows me the trash bucket,
which also has the $20 bill I had smuggled in my pocket all cut up
into little confetti pieces.) She says she told me not to bring any
money and does not apologize at all for cutting up the cash.
The phone rings and she says, "That'll be the manager, he looks like
a mean mother and we're out of money. Let's go."
Before I can say a word, we're out the door, down the steps and out
onto the street. She is very excited and says, "Look, it's completely
dark and you look great. The car is parked just a little way up the
road and we'll be there in no time. Here's the plan: We pretend we're
a couple of hookers on the stroll, we have some fun, then we drive
home and fuck like bunnies. Besides, there isn't any choice now. If
we stick together, there shouldn't be anything to worry about. Loosen
up, have some fun!"
So together we began walking up the stroll like a couple of hookers.
The high heeled shoes hurt like hell, but things got a bit better
once I'd adjusted my walk a little. We are walking against traffic
and some cars slowed down to check us out, some pass by a couple of
times. Some of the regular pros on the street give us the evil eye,
but we keep walking and don't challenge their turf. I try to get into
character and strut a bit, but I can't match Natalie for raw sex
appeal. An old Honda stops and Natalie goes over to see what he
wants. She is so hot. She leans way over at the waist and gives the
guy inside a look down her shirt, and she wasn't wearing a bra. She
does work in an advertising agency after all, so she knows how to
advertise. Not that she has to, since she is the most beautiful girl
out there.
She looks over and yells to me, "Hey Julia, this guy wants a
straight fuck and I'm on the rag, you interested?" I'm practically
petrified but I manage to shake my head no and Natalie tells the guy
to look for us again in about a week. He drives off, probably very
disappointed. Natalie is having a ball.
This happens several more times with guys in old Chevys, Fords and
so on. We keep going and I can just see the bowling alley sign in the
distance when this big Lexus SUV pulls over. Natalie actually looks
impressed this time. The guy rolls down the window and calls us over.
Natalie stands up on the running board and is in discussions for more
than a few seconds. She jumps down and whispers, "Oh my god, this guy
wants to pay us $1,500!" "So what?" I say. But Natalie is glowing
like a hot coal, very excited.
"So what?" she says. "Do you know how long I have to work to earn
1500 bucks? A long fucking time! And you know I'm not any kind of
virgin, and that I have been with other guys, so don't get all
Puritan on me. What's one more guy? Besides he just wants to fuck me
while you watch. You don't have to do anything. The whole deal will
take like twenty minutes, tops, and we earn $1,500! We are SO going!"
"Go ahead," I say. But she won't have that. "You have to come to,"
she says, "he wants you to watch, it's part of his kink, I think. And
besides, you have to be there to protect me in case this guy turns
out to be some kind of American Psycho-type. C'mon."
With that she hops into the front seat of the car and slams the
door. I hesitate, but she dangles the only car key we have in front
of me and I decide right then that it is better to go with my
girlfriend and some rich guy in a really nice car, than to be stuck
alone on the street in hooker clothes with no money, no id and no car
key. So I jump into the back seat before the guy can change his mind.
All the way over to the guy's hotel Natalie is rubbing his dick
through his pants and licking his ear and moaning and shit like that,
really playing up the role. Just before we get to the hotel the guy
tells me that there are two coats, an overcoat and a raincoat
actually, in the back of the SUV and tells us to put them on. The
hotel is really nice and he doesn't want to get security all over his
ass.
By the time he pulls up to have the car valet parked, Natalie and I
are wrapped in the coats. Even though we are mostly covered, it isn't
often that two hot chicks wearing way too much make-up go strolling
through this nice hotel lobby wearing coats that obviously aren't
theirs, so we still attract a fair amount of attention. Natalie is
giggling as we head through the lobby as fast as possible, up the
elevator and, next thing you know, we are in the guy's posh hotel
room and Natalie looks like a wolf who has found her prey. Her coat
falls to the floor and she is all over the guy.
Now, I had always heard that hookers don't kiss their clients on the
lips, but Natalie had apparently never heard about that because those
two were French kissing within seconds. Not sure about what I was
supposed to do, but knowing that I didn't want to attract too much
attention to myself, I also drop my coat and go to find a nice, quiet
corner to unobtrusively "observe".
The guy is pawing Natalie all over and they are kissing and saying
Oh Baby to each other, and if I wasn't so scared, I'd have been
turned on. The pouch thing that encases my own dick turns out to be
very restrictive, so that even if I wanted to get a hard on, the
thing won't let me. Natalie is soon rubbing this guy's cock with her
leg and has her hands on his ass and is pulling him in tighter. He
has her tits out of her dress and is sucking and licking them between
French kisses.
The guy motions me over and tells me to get down on my knees and get
his fucking cock out of his pants. Apparently he wants to be
"fluffed" before proceeding to the main event with Natalie. At first
I hesitate but Natalie shoots me a look and does that finger-thumb
rubbing thing that indicates that money is at stake. In a kind of
surreal dream state I find myself pulling down this guy's zipper and
fishing out his cock, which is not that easy since it is hard as a
rock. He tells me to put it in my mouth and suck it.
I notice that they now have an arm around each other and are both
looking down at me. "Suck it," he says again, but with more threat
than before.
"Make that bitch suck your cock," Natalie says. She looks me
straight in the eye and says, "Do it, whore."
"You heard her, whore, suck that cock," says the guy. "Suck it, or
I'll throw you're a right outta here and call Security. They don't
like whores in their hallway, and they'll call the cops. You'll end
up in jail, w. And who is going to bail your whore ass outta jail?"
"No one I know," says Natalie, answering him.
The two of them are standing there like royalty, and Natalie has a
little superior smug look on her face. She looks at me and says, "Do
it."
I gingerly take the fat cock in my mouth and tentatively begin to
suck it. I am almost too bewildered and overwhelmed by how far out of
control the night has gone to be repulsed. Almost.
I snap back to full reality when the guy slams the full length of
his cock into mouth. Natalie is once again all over the guy, more
turned on than ever. She moves around behind me so that her pelvis is
right up against the back of my neck and starts slamming her hips
like she is fuck the guy. The two of them are having wild sex, but my
mouth is her surrogate cunt. Whenever her hips slam forward the guy's
cock goes down my throat and I pull back in time with her hips
pulling back I manage to get my mouth off his dick just before it
explodes, but not in time for it to miss spurting all over me. I feel
a wetness on the back of my neck and for one irrational instant I
wonder if somehow his cock has penetrated my skin and come out the
other side; but then I realize that the wetness is from Natalie; she
was so turned on.
I kind of crawl away, finally freed from being trapped between their
bodies. Natalie and the guy are holding each other and basking in the
afterglow. Somehow I'm getting the sense that I have missed
something. Natalie and the guy seem just a little too comfortable
with each other, I realize.
This feeling is confirmed when Natalie turns to me and says, "This
is probably a good time to tell you that I am breaking up with you."
She kisses the guy again and asks him where he put her bag. "Uck,"
she says as she digs it out of the closet, "I have got to get out of
these awful clothes. I feel so cheap, in fact, motioning to me, she
says, I feel just like he looks."
I begin stammering, unable to forms words. I'm so shocked and
overwhelmed. I don't know what to say, but Natalie is totally cool.
She turns to me and says, "I mean, just look at you. Now look at
him. Which would you choose if you were me?"
She turns to the guy and says, "Tell me Johnnie, have you ever been
a female slut whore, sucking some guy's dick for money, and had your
face all covered in cum? No?" Back to me, "Well, then, there you go."
Grabbing a handful of her stuff she heads for the bathroom but the
guy, Johnnie, asks, "What do we do with him now?"
Natalie stops and says, "Well, he did earn some money. Not the
$1500, but you should pay him something for the service. What's a
blow job from a street walker go for now? $30? $40? Tell you what,
since it was "her" first time we'll give her a bonus, make it $50.
Plus cab fare, whores always get cab fare, plus the $20 I destroyed
back in that dive hotel, makes it about, what, $90?" Turning back to
head for the bathroom she says, "Pay the bitch and get her the fuck
out of here." And with that Natalie slams the door behind her and it
just me and the guy.
He hands me the money, my purse and a coat. He tells me that he is
going to call down to the bell stand to get me a cab. He also wants
the bellhop to collect the coat, since it is really expensive and he
doesn't want to lose it. Handing me a napkin, he says, "Before you
go, you should probably wipe the cum off your face."
It is very humiliating having to hand the door man the coat before I
got into that cab. As soon as he saw me got this disgusted look on
his face. The cabbie was worse. He wouldn't let me sit in the back
seat since he was afraid I would get it messy "from leaks or
something" and was afraid that maybe I was also a dope addict who was
going to shoot up if he didn't keep an eye on me, so I had to sit in
front next to him.
On the way back I can tell the cab driver is checking me out from
the corner of his eye. I may be a whore, but I'm still a cute one. It
has been a rough night for me and all I want to do is get back to my
car and get home. But the cabbie has other ideas.
We have been driving for a while and I can tell that we are getting
close to the bowling alley where we stashed the car. That feels like
days ago. Suddenly the cab driver pulls over and stops the car. He
turns off the engine and says that although the fare has to be paid
in cash, he will take his tip "in trade". With that he pulls down his
zipper and pulls out his already semi-hard cock. I just shake my head
and whisper no and say "Please just take me where I am going." I show
him that I have money and will be happy to pay him the fare and the
tip, but he gets really mad and leans across me and opens the
passenger side door. It may be scary in the cab, but it is much
scarier outside.
He says, "Girlie, it's either me or the street. And if it's the
street you know you ain't never gonna make it out of here alive. Why,
if the fella's see a pretty little white girl like you shakin her ass
in this part of town, well, they be taking you someplace where
they'll line up the hard pipe brothers day and night. They be workin'
you til there ain't nothin' left to work. You can bet yo ass on that.
So what's it gonna be?"
I close the door and go to work on that driver's cock. I remember
the rubbers in my purse and roll one on him, then get back to
business. I just want this night to be over and this cabbie stands
between me and a hot shower. He's soon rubbing my "hair" and moaning.
I wrap a few fingers around the base of his cock and gently pump him
along with the rhythm of my sucking. My other hand gently squeezes
his nuts. Things progressed pretty fast after that and soon he is
shooting a load of cum into the condom. I can feel his dick pulse in
my mouth and I prayed the condom held.
When I was finished he handed me a napkin from some doughnut shop
and, indicating his dick, told me to clean him up. "I don't touch no
jism, ever," he said. So I pulled the condom off and used the napkin
to wipe off his cock. He said, And don't think you're gonna put that
shit in my trash bag, and he watched while I neatly but the napkin
and the used condom in my purse. He zipped up and said under his
breath, "Now that's what I'm talkin' about."
He had turned off the meter when he pulled over and was nice enough
not to turn it back on for the remainder of the drive back to the
car. He dropped me off about a block off the main drag, right up from
the bowling alley. He explained that he didn't like for working girls
to be seen getting out of his cab, so he preferred to let me off
somewhere quiet, but he promised he'd watch to make sure I made it to
my car okay. He even refused to be paid for the ride. "Keep it," he
said, "this one's on me. I know how hard you all got to work for yo
money."
When I got close to the car I could see that someone was inside and
that the engine was running. I figured that it was probably in the
process of getting stolen. Figures, I said to myself, not even
surprised that yet another thing had gone wrong on this fucked up
night. I didn't know whether to run or to try to fight off the
thieves.
As it turned out, it was Natalie. As soon as she saw me she came
running out with a big smile on her face and gave me a big, wet,
sloppy kiss.
"Wasn't that great!" she said.
I was totally confused. "Didn't you just break up with me?" I asked.
"Oh, hell no," She said. "That was all a gag. You are way too much
fun to break up with!"
"But who was that guy?"
"Oh, silly, that was an old friend of mine. He's just in town on
business. He's totally gay and as soon as he called me I knew we had
to do something wild."
"He's gay? That guy who had his hands all over you and was French
kissing you was gay?"
"He said it was awful and he almost gagged from the kissing, but he
said the blow job was really good."
"So we're not broken up?" I asked again.
"Nope," she said.
"So what do we do now?"
She seemed to think a minute and said, "Well, the night is young and
you can stay here and make some more money, or we can go home and
fuck like bunnies." I said that I would rather go home. "Thought so,"
she said. "But first, I have a coat in the trunk for you. You should
probably put it on so that we don't get stopped by the cops, and I
don't want to be seen driving with a hooker."
As we turned to get into the car, she said, "By the way, we told the
driver to take his time getting you here, since I wanted to be here
when you got back. What did he do, drive slow or take a "scenic
route"?"
"Actually," I said, "he pulled over so that I could give him a blow
job. He even gave me the ride for free."
"You got a free ride for a bj?" she asked, stunned.
"Yes," I said, "plus the tip."
"I have an idea," she said. "Give me the money you got from
Johnnie." When I did, she said with a sly smile, "You gave a bj to
some guy and you're giving the money to me. That makes me your pimp.
This was the easiest money I ever earned. I think I'll sell your hot
ass on the street more often."
But I say, "Wait a minute, don't you mind that I just gave a guy a
blow job?"
"Two guys," she reminds me.
The thought is not comforting.
Then she says, "Why should I mind? I've done it lots of times."
I was about to go into the whole natural order of guys and girls
discussion, but decided that it probably wasn't the time.
She opens the car door and begins to get in and says, "Let's go home
and have some hot lesbian sex." Then, winking at me, she says, "I'll
get my strap on, slut, so you can be ready the next time I pimp out
your ass."
Bree
- 12.08.2022
- 24
- 0
