Dating Tonight?

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Shopping for a whore.
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14 Followers

One of my favorite things about living in the city is the enormous amount of stimulus coming from every direction no matter what time of day or night. Driving down Broad Street on a warm May evening I found myself at a heightened state of awareness. The sun had just gone down and a warm spring breeze was blowing through my open car windows as I pulled up to the light on Walnut Street. The sounds and smells of the traffic, the multitudes of people on the sidewalk, even the rank odor wafting up from the subway steps, it was all being absorbed by my senses and being converted to arousal.

The light turned green and the tires of the car next to me let out a chirp as the driver rushed on to the next red light. The cab behind me blew his horn, and I purposely took my time pulling into the intersection. I knew where I was headed, and I wanted to enjoy every minute of this night.

Two blocks later I swung a left on Pine Street, hoping I wasn't too early. I spotted a heavyset black woman on the sidewalk wearing a short, formfitting, sequined dress and matching pumps, and knew I was right on time. The whores were coming out.

I slowed down to get a better look at my sequined princess and she turned towards my open window and smiled. I took one look at her rotted out mouth and automatically pushed my foot down on the gas, leaving her to continue her toothless stroll. I made a right on Twelfth Street and another on Lombard, slowing once again to get a closer look at two white girls in tight shorts and heels. As I got closer one looked directly at me and began rubbing herself through her white shorts. My cock gave an immediate jump, and I smiled at her, only to realize when I pulled along side them that both girls had their own cocks, which were hardly contained inside their tight shorts. I let out a laugh, said no thanks and continued up Lombard Street. I pulled back up to Broad, and there, on the other side of the street; I saw what I was looking for. She was standing up against a brick wall, just outside the rays of light from a nearby street pole. She was small and thin, but stood at least 5' 7 in the towering strappy platform heels she wore. Her skirt was a pale orange, and short enough that the bottom of her ass was visible with each step. As I pulled up to the curb I could see her matching mid riff top was sheer, and her small breasts and cute little nipples were clearly visible.

"You dating tonight?" she asked, letting out a stream of cigarette smoke from her painted lips.

"I am now; do you have any objections over taking a ride to the Rittenhouse? I'll make it worth your while."

"I have my own room around the corner" she said, then quickly adding, "but then again, the Rittenhouse is a nice hotel, how much worth my while?"

"I have three hundred roses for two hours....plus whatever you want from room service."

She had strolled up to my window and my eyes locked onto her face. This girl was too pretty to be walking the streets. Hookers only looked like this in Hollywood movies, and even that's pushing it. A truly beautiful face, high cheekbones, dark eyes accented by an even darker coat of eye liner, and full lips painted a deep shade of purple. Her hair was tied back in a ponytail that fell just short of her shoulders, and she was wearing the most amazing perfume.

"You'll walk into a hotel with me dressed like this? What, you want to play businessman with his little fucking whore? What is this, some pretty woman shit?" she looked at me for a minute shaking her head. "ok, four and I'm yours, two hours."

Four hundred dollars for a couple hours with a street whore was a lot of money, but there was something very special about this girl. I quickly agreed and she hopped in my car almost as quickly as I popped the locks.

We learned a little about each other during the short ride to the hotel. I told her about my business, and she told me her name was Drew, and that she danced at a couple clubs around town, but tonight she needed to make some extra money quickly.

The Rittenhouse Hotel was less than six blocks from where I picked up Drew. I pulled up to the entrance and the valet drivers ran over and opened our car doors. As Drew stepped out of the car it was if time froze. The drivers, the other hotel guests, people walking down the sidewalk, they all stopped dead in their tracks as this gorgeous woman dressed as the perfect slut stepped out of the car and accompanied me into the hotel. No one said I word, they just dropped their mouths open and stared. I have to admit it was uncomfortable walking thru the lobby of a four star hotel with this woman, but Drew wrapped her arm thru mine and gracefully strolled to the elevator.

I poured us each a drink from the mini bar and Drew walked up behind me and began stroking my cock.

"Ah yes, for you," I said, pulling out my money clip and pulling four one hundred dollar bills from the roll. "I think your going to earn this."

"You think so huh? Lets get you out of those pants and see."

I kicked off my shoes and socks and dropped my pants to the floor. My cock, so grateful at having been released, bounced up and down in front of me.

"Mmm, let me take care of this for you honey," Drew said, dropping to her knees in front of me.

She carefully took my cock in her mouth, and began lightly teasing the head with her tongue. I put my hands behind my head and intertwined my fingers, watching Drew run her painted nails along my balls as she took my cock deeper into her mouth. I reached down and lifted her chin so she was looking up at me, then gently put my hands on her cheeks and began sliding in and out of her mouth.

"You can fuck my face if you want; I mean really fuck it if that turns you on."

She didn't have to say anything else. I wrapped her ponytail around my right hand, held the side of her face with the other, and began pushing my cock into her throat. I don't think she was ready for me to push that hard and she began to gag, so I let up long enough for her to get a breath and then pushed myself back in even harder. I felt her begin to choke again but held myself there, until I saw the first tear run from her eye, leaving a trail of smudged mascara in its wake. When I let go of her head she pulled back, still choking, and a glob of spit and pre cum came poring past her lips. I repeated the process a half dozen times, until her entire face was a smeared mess of make up and drool. Drew continued kneeling on the floor looking up at me, the sticky mess on her face hanging in globs from her chin, before it dripped down onto the carpet.

I grabbed Drew under her arms and half carried half dragged her onto the bed. I threw her onto the mattress grabbed her by the thighs and drug her to the edge of the bed where I was standing. I pulled her panties off to the side and without hesitation, pushed my cock past her meaty cunt lips. I couldn't believe how wet she was after suffering through my abuse of her throat; I was beginning to think I found my dream girl.

I stood at the edge of the bed using my calf muscles to fuck Drew as hard as I could. Drew's eyes glanced away from me for a second, and without even thinking I took my right arm off her thigh reached over and slapped her face.

"Keep looking at me while I'm fucking you, got it?"

Right away her eyes locked back onto mine and she let out a meek "yes".

I started to feel the cum boiling it's way out of my balls so I backed out of her pussy and took a couple steps backwards

."Rub your pussy for me; I want to watch to watch a beautiful little cunt like you touch herself."

I slide my hand slowly up and down the shaft of my cock, my eyes going back and forth between the pussy I was just fucking and the beautiful face smeared with make up and dried spit.

I crawled up on top of Drew, at first straddling her tits and pointing my cock towards her face.

"Let me lick your ass, I'm fucking great at that, please...let me fuck your ass with my tongue."

I spun myself around so I was facing her pussy, and leaned back until I felt Drew's tongue penetrating my ass. She licked and sucked at my hole until I was whimpering, burying her face in my ass cheeks and stroking my cock with her long fingers.

There was no way I was going to hold on much longer, I wanted to cum, and Drew's tongue in my ass was incredible, but I had one more thing in mind.

I slowly pulled myself away form Drew's face, grabbed her by the arm and yanked her to her feet. Her strappy heels caused her to stumble for a moment but she quickly regained her balance. I stopped along side the large mahogany desk in the corner of the suite and shoved Drew into the chair. I grabbed her ponytail and once again began fucking the bottom of her throat, only this time I wasn't able to make her gag. Just as I was about to cum, I pulled out and pushed her head against the cold hard wooden desktop. I started stroking my cock slowly, and the cum began shooting out in streams, covering both the side of her face and the desktop. Drew remained still, my cum running down the side of her face onto the desk.

"Start cleaning up your mess."

Without hesitation, Drew began sucking the cum from the desktop.

I pushed her legs apart and forced my fingers inside her tight pussy. As Drew licked and slurped my cum off the desktop, I reached down and began fucking her with my right hand and I instructed her to start rubbing her clit. I could feel the contractions starting inside her pussy. I bent over and whispered in her ear that she was my skanky little fuck toy, and that I owned her. I told her next time I would have a room full of men waiting to fuck her, and that they would pay me, not her. My words in conjunction with my fingers finally set her off, and Drew threw her body back in the chair, arching her back as she came. I gave her a moment to catch her breath.

I could hardly recognize her. Drew's face and hair were covered in my quickly drying cum and her saliva. Her eyeliner ran in black streaks from her eyes to the bottom of her jaw, and her lipstick was smeared around her lips like a clown. I pulled my digital camera from my bag on the corner of the desk and began snapping pictures.

"Now go take a shower you filthy ass licking whore,"

I stretched out on the bed and turned on the TV, feeling more satisfied than I ever remember feeling. Drew walked out of the bathroom a few minutes later wrapped in a towel. Her skin was scrubbed pink and she looked more beautiful than I had remembered. She lay down next to me and put her head on my chest.

"Weren't you nervous standing out on the street dressed like that?

"A little, I knew you would get there, and that you would never let anything happen to me."

"Damn straight, you're my baby. I love you more than you'll ever know."

"So what do you want to do tomorrow?"

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14 Followers
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4 Comments
AnonymousAnonymousalmost 16 years ago
I liked it

I had a friend that used to do this with his wife all the time. They both loved the role playing. They would play on the street , in bars and hotels. Added a lot of spice.

As to originality I can't comment, but as a fun little story, I thought it was great

AnonymousAnonymousalmost 16 years ago
Unoriginal

Sometimes we write for ourselves; sometimes we write for others; and sometimes, for both. I hope this one was for you. Although the story had some touches that were your own, it was a story that, for the most part, we have read time again.

AnonymousAnonymousalmost 16 years ago
What a crappy story, if you can call it that.

As a writer I think you're nothing but a creep and a moron who should get back in the closet where you belong. Please do us all a favor and give up writing.

junesmatejunesmatealmost 16 years ago
YOU NEED HELP.

You're not even an apology for a man.

Go back to abusing yourself.

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