Bailey's reality

dansemajik

Literotica Guru
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Aug 23, 2000
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Bailey is 28, working in a dead end job that doesn't cover her rent and car payment. She is getting pressure from a so called friend to join his club. He sees her as a money maker. He is a glorified pimp. She would keep half of what she made, the other half would go to pay her expenses. He told her she could work the hours she wanted, accept the clients she wanted, and her time would belong to her. She turned him down, then began thinking, why not become her own pimp?

IC: I liked having sex. I looked good. I was 5'8, with long chocolate brown hair. My eyes were the color of honey. My bone structure was classic, straight nose, hight cheekbones, eyes had an exotic slant to them. My lips were full, and shaped by a master. I had grown tired of pushing paper in a 6x6 cubicle for nine bucks an hour. I made some discreet phone calls, and got a potential client list together. I would only accept appointments from men past their 45th birthday, and my price was five hundred dollars for straight sex, oral or anal. For the kinky stuff, I charged a thousand, and I was theirs for an entire night.

I put an ad in a certain periodical, left a number to a voice mail box. i was getting alot of responses. I began booking appointments. I didn't go to college to be a prostitute, but I was willing to give it a shot. I couldn't pay my bills by working a straight job. I would work one I could make money at.

I had returned some phone calls, and was waiting for a client to call me to tell me where to meet him.

I was nervous. My first night as a hooker....I was already getting wet.
 
"Bailey this is Jack. Jack Bronson, yeh...

I'm the painter...

Thank's, a lot of people never saw the show...

Listen it's raining cats and dogs right now why don't I pick you up
at The Plaza, side lobby...

*He laughs*

No baby, not there. I'm dropping a grand on you tonight but the Plaza's not in the picture...

My place...

Hey, look it up in the book if you want. A nice loft, East Village.
You've have nada to worry about. I got a good reputation.
I lose it and my works not worth a dime...

Ok, Nine it is...

I'll be in cab. I never drive in this town."

----------------------------------------------------------------------------

OOC:
Jack Bronson well known artist, currently working on a series
called Women of the Night. He want's sex and then a model. An all night thousand dollar gig. Sounds interesting.

Jack is medium height but heavily muscled. He will be 54 years old on Christmas day. He wears his hair long and it is salted with grey. He's been told he looks like Paul Newman.
Maybe...
 
Bailey

Jack Bronson. I looked at the background my investigator had supplied. he was expensive, but I had to be safe.

I threw together an overnight bag. The Plaza was right around the corner. I walked and sat in the lobby and waited for him to come in and get me. I was dressed in a black trench coat made of leather to ward off the rain. Under it, I wore a simple man tailored silk blouse and a pair of black linen slacks. I am wearing black low heeled boots. My umbrella is black, and my overnight case is black. I have piled my hair on top of my head, men like to watch it fall from the pins...

I take deep breaths trying to calm my nerves...I see him walking to the door....I smile...handsome...Love the hair....I stand and hand him my bag. He looks me over and smiles back, taking my bag and offering his elbow.

We get into the cab. His eyes keep running over my face, he doesn't say anything, he just looks at me. I look back at him. It is my nature to be direct. I wonder what he likes?
 
"You're almost as tall as I am."

Jack helped her into the cab,
"In heels you'd be taller."

She wondered if he wanted her in heels tonight ...had she brought any?

The cab made it's way downtown through heavy traffic.
The lights along Broadway seemed especially bright.

"Bailey, right?
Just Bailey."

She nodded.
"OK Bailey, take a look at these. "

Bronson pulled out half a dozen glossy prints of his paintings.

He tapped the cabby on the shoulder and asked if it was allright to flip on the overhead for a minute. He must have found one of the few that spoke English, she thought.

The paintings were exquisite. Done in an almost hyper realistic style yet suffused with a moodiness, a darknesss that set them apart from rote realism.
Each showed a beautiful woman either sitting or reclining on a rumpled bed. Behind them, city lights could be seen through tall windows. Most of the women were reclining, a few were sitting.
All were nude and had a...

"Freshly fucked look right?"

Jack looked at Bailey.

"See, that's what we do honey.
We screw like rabbits and before the juice is dry, I paint you.
That sound kinky enough?"

Bailey smiled. It din't sound kinky at all.
 
Bailey

I glanced at the photos he was showing me. Women, of various, races, heights, proptortion, some beautiful, some plain. All with that dewey eyed expression of just having had sex. the flush of desire still on their cheeks and chests, and the moist swollenness of the lips very clear in the prints of the paintings.

I looked at him, and nodded. "Its your night Jack. You are the boss." I smiled.

he was a handsome man. I could screw him and stand still for a few hours if thats what he wanted.

I thought I would ask to be sure. "Jack, tell me, whats on the agenda tonite? I like to know what I am getting into."

I gave him my direct look, with a hint of a smile. I wanted him to know that I was his for the night, but I wanted to know what was in store for me.
 
"You want specifics huh?
Say are you hungry? There's a Thai place near my
studio we can get some take out if you want.'

Jack sat back and put his arm around Bailey's shoulder.
"Guess I can do that right? The clock started when I picked you up."
She nodded.
"Okay Bailey, We're going up to my Loft. Maybe we'll have a bite to eat and drink some wine. I'll show you around and try to seduce you with my talent. I know I'm paying for you but old habits die hard see.
Then I'm going to spend about four or five hours fucking you. I plan to get my moneys worth there, I'm good for a few in that time span. And with someone who looks like you I may go all night and call you back again for the pictures."

She was aware of the Arch and the freaks in Washington square gliding by her window. It wouldn't be long now.

"When we finish and you look like your'e the most satiated woman who's ever been had. I draw you, simple stuff.
I'll do the paintings later on."

The cab pulled to the curb.
"We're here.", He said,
"Let's go."
 
Bailey

His arm felt heavy against my shoulders, but it was a good feeling. He smelled good, aramis maybe? His mouth close to my ear as he told me about our evening sent shivers down my neck, my spine right to my pussy.

His voice was smooth and silky. I enjoyed listening to him talk.

We stopped at a small bistro, he helped me out of the cab. My nerves were fairly steady already, but I figured a couple glasses of wine would do the rest.

His hand on the small of my back started the shivers again, and I knew that I was primed and ready for this man. I would give him what he paid for, and then some.
 
They split a bottle of wine at the café and made small talk for the better part of an hour, then Jack guided her a block and a half past an assortment of human oddities typical of New York night life. At the corner of a street lined with barred and shutterd shops he turned into a shallow alcove and unlocked a blank metal door. It took awhile, there were three beefy padlocks on it. He smiled up at Bailey...

"Neighborhoods gone downhill fast. I should move but I can't make myself. I've been working out of this place for twenty years."

He flipped a switch and a small lamp glowed at the top of the stairs. He led her up to a wide landing with a variety of old comfortable furniture scattered about.

"A second living room kind of...People drop by here at all hours. Sometimes I'm working and they can make themselves at home out here."

You work through the night? She asked. Do the other tenants complain?

Jack laughed as he opened the door,
"They better not. I own the building."
 
Bailey

His loft was huge. It took up the entire floor. It was completely open. His studio by the windows on the East side, below the sky lights...His bed by the windows on the West side. he had sofas and chairs and tables scattered about. A galley kitchen with all the accoutrements that a serious cook would have.

I nodded and smiled at him.."Great place" I said.

He took my bag and tossed it on the bed.....He asked if I had brought any heels...I nodded and went to my bag, taking off my trench coat. I sat on the bed, to remove my boots, and slipped my strappy 3 inch heels on. I stood and he smiled.

"Bailey at your service" I said. He was the boss.
 
"You are taller than me."
Indeed with heels on Bailey topped him by two inches. He wasn't the least intimidated. He smiled leaned up and kissed her on the lips. The gloss she was wearing tasted just fine.

"I love to stand on my tiptoes when I kiss. It makes me hot. How about you?"

He didn't wait for an answer but walked over to the counter and picked up a bottle of cognac, very good cognac and two glasses.

"Come on over here Bailey"
He led her past several large canvases that she would like to have seen in the daylight and into the corner of the loft. Eight foot windows ran along both walls giving a view of the park on one side and the Midtown skyline on the other.

"Empire State...Grand isn't it?, Ever been up there at night?"

She hadn't.

"Well, let's go sometime. Sometime when your not working."

Was he asking for a date? A real date?

"OK Bailey this is where we try to get a bit worked up. Sorry to say I'm not one for quickies. I love the foreplay part and I don't want to be rushed. Let's have a drink and loosen up."

There was a huge high bed turned to face out both rows of windows. A lovely overstuffed chair, a desk and a reading lamp which he turned on.

"Excuse me a minute."
He walked back towards the kitchen. She heard a switch flip and the overhead lights went off. The reading lamp provided a warm golden ilumination,
that didn't go far beyond this corner.
Then she heard music, a soft sweet voice that seemed to come from the past.

Jack stepped into the circle of light. He'd removed his shirt. His chest was broad and
muscled, no flab that she could see. Silver had begun to invade the curly balck hair that grew on it.
"Dinah Shore, showing my age...
Take a sip of the cognac, it's pretty good."
He sat down in the armchair and looked at her.

"Now Bailey can you start to take off your clothes ? I'd like to see you with just those heels on your pretty feet."
 
Bailey

I took a sip of the smooth cognac, liking the slight burn as it traveled down my throat.

He was a fine figure of a man. His body was firm, and muscular. No middle age paunch to speak of. I had seen a mini gym in one of the corners. he worked out.

I did as he requested, and stood up. he sat back in the easy chair and his eyes were watching me. I slowly unbuttoned my shirt. I left it tucked in, as I worked the buttons loose. He could see a glimps of my champange colored bra. I put my hands to my slim black belt, and I unfastened the silver buckle. I unbuttoned my slacks and then pulled the zipper down. I let my pants fall to the floor in a soft whoosh. My legs were bare. my shirt hung open as I stepped out of my pants. I let the shirt fall down my arms, and I let it drop from my hands. I turned around giving him a view of my back side my thong revealed my ass nicely, as I unfastened my bra.

I let the bra fall from my hands and I turned to him, as slid my thong down my legs. I stood before him, in those black strappy heels, and nothing else. I reached up and pulled the pins from my hair, letting it fall around my head and shoulders.

His eyes had an intensity that almost floored me. He was already painting me. I could see his erection thru the fabric of his pants.

I waited for direction.
 
Jack was surprised. Often a woman who looked as this one did in her clothes could be a disapointment outside of them. About the best compliment he could pay a woman was that she looked better naked than clothed. Bailey did and then some. There was no place he could begin to celebrate over any other. Hair, lips , breasts, legs. Perfection.
Jack was not a man easy to impress. This time he was.

She stood there against the backdrop of tall windows prismed with the reflection of passing cars and neon signs. She stood there looking at him steadily with those amber eyes and her lips with just the faintest trace of a smile.

Jack stood up.

"OK. You are blessed.
You should thank your gene givers Bailey because I've never seen a finer looking woman."

He stood up in front of her and kissed those pefect lips...cupped her breasts in his rough hands.
He had the body of a prizefighter. His arms were thick and sinewy, a working mans arms.
He began to unbuckle his belt when he felt her fingers take their place. He looked first at them. Long graceful fingers each tipped with a clear polished nail...
Then he looked in those cats eyes of hers...

"Bailey, you tell me.
What won't you do."
 
Bailey

I stood watching him look at me. Knowing what he was seeing. His words only confirmed what I already knew. I had been told my entire life what he had just told me. I had never used my looks or my body to gain anything until now. I was going to use what my parents gave me...and finally get somewhere.

I began to unbuckle his belt, after taking his hands away. His question surprised me. I looked at him and said, "Jack, this night is yours. I will do anything you ask of me. If things get too rough, I will use the word pickle as a safeword ok?" I waited to see if he understood. I always used pickle because it wasn't a word one would utter in the throes of passion. At least, I didn't think so.

I finished unbuckling, unzipping and finally letting his pants fall to his feet. He stepped out, and I was able to admire his body. He was strong, rugged and very well endowed. I knew that even while I pleasured him, he would also pleasure me. I reached for my bag and held out an assortment of condoms. "You get to pick the color for the first round Jack"
 
Eleven...

"Premature Bailey, though if you had one in paisley I'd wear it just because."

Jack smiled and circled behind her.
"I'm paying a grand tonight and you've given me permission to do about anything I want..."

She feels his thick cock pressed between her cheeks...his lips kissing her shoulders ... her neck...strong arms circle her waist...hands warm against her stomach.

His voice, soft in her ear,
"A thousand dollar fuck, does not begin with a condum."

On the table beside the bed the clock said eleven PM.
 
Bailey

I smiled and set the packages on the table by the bed as he circled me. I felt as though I was being stalked. His eyes and his manner were predatory, and his words were a reminder to me why I was here.

I turned as he circled me. I bowed to him. "My apologies, I await your direction." I said it in a tone that was respectful and calm. Not a hint of sarcasm. My voice modulated with enough of my growing desire to make it a bit sultry.
 
She was standing in front of him totally nude without a hint of self consciousness.
She was as confident and calm in beauty as a Renaissance statue.
And in the low even ariculation of her voice, Jack found another deep chord of response. Already he was thinking of ways not to let this one go after tonight.
He ran his hands through her hair and it fell like water through his open fingers. He bent forward
and kissed the small of her back and felt a quickening in her flesh. He knelt down and circled her slim ankles with his hands then followed the long swell of her calf to the hollow behind her knees where again he pressed his lips. His fingers glided smoothly up the contours of her thighs all the way to the round curve of her ass which he cupped, squeezing lightly and rose up
crossing his hands over her tight belly, pressing again into her backside, blowing hair away fom her shoulders and kissing them. She feels his tongue and his teeth on her skin.

"Bailey," he murmers,
"Your strung like a thoroughbred, my hands are touching warm bronze. You could make a blind man
cum."
 
Bailey

His lips on the small of my back sent tremors through out my body. Ahh, his lips on the back of my knees, my ass, then my neck, teeth, lips and then the tease of his breath against the dampened spots. My nipples were erect and aching they were so hard.

His words had a peculiar effect on me. As his hands skimmed up my stomach and to my breasts, I put my hands behind me, and took his dick in my hands. I lightly held it, cupping his balls, and stroking slightly. "I think Jack, that you are more than just a master painter." I could imagine this night with him to be more than just me pleasing him. I had a feeling this night would be full of new and wonderful things.

I felt his hands turn me toward him, and I turned, looking at him as he looked at me. My hands went to his chest, splayed out, feeling the crinkly hair there the hardness of his nipples. I bent down a bit and kissed him, softly on the lips. My hands still roaming over his body, feeling the skin, and muscle and bone all fused together into some kind of living marble.

His breath mingled with mine smelled and tasted of cognac. A heady thing to breathe. My hair fell and covered one of his shoulders as I leaned in to kiss his neck. He shivered a bit as it ran like silk over his skin.
 
Jack felt the hard tips of her breasts, brushing across his chest as she kissed his neck and shoulders. She had already generated more desire than all of the other call girls he'd brought up here combined. The thought of those delicately curved lips on his naked skin was too much...

He raised her face to his and kissed her. His tongue moved across her parted lips, tracing, memorizing each curve, their heat , their texture. He felt her tongue touching his and their mouths melted together as they took turns deliciously exploring each other...

Her breasts were high and firm in his hands. They rose in splendid curves to rosey peakes.
Jack kissed his way from Bailey's throat along sweetly rising flesh until his mouth took in and gently sucked each perfect nipple...

"I want to make love to your breasts for awhile
Honey" He whispered against them,
"I hope you don't mind."
 
Bailey

I am back...thanks for the rescue Ariosto....D.

The feel of his tongue and teeth on my erect nipples was so sexy. I shivered in his hands, as he ran his tongue over the hard nubs and then gently bit them. They were hypersensitive and I felt as though I would go insane until I let myself go, and enjoy the feeling he was evoking in me.

I put my hands on his head and pushed him deeper into my chest. I leaned down and kissed one of his ears, running my tongue lightly around the outer edges, then blowing on the area. I let my hands run through his hair, feeling the fullness of it.

I closed my eyes and relaxed as he had his way with my breasts.
 
Her tongue and warm breath bathing his ear are more than a siren's call to Jack. He presses himself against her taught stomach, tensing and untensing his penis against her skin. He holds her nipples like burning jewels in his mouth, sucking them slowly, pulling them through his lips between the raking gates of hard white teeth.
His hands cup the bottom of her breasts and raise them higher, squeezing them and savoring their firm smooth weight and texture.
Bailey's long fingers are in his hair, nails on his scalp sending out tingling waves of pleasure.
He plays his tongue roughly across her sensitive tips as he draws them in deeper. Jack can imagine the taste of her milk, warm and rich as he pulls it up from a secret place...

A clock was striking midnight outside across the square
 
Bailey

I wanted to climb out of my skin. His teeth and lips and tongue were like tiny magicians weaving tiny spells over me. My breath was coming out in gasps and my pussy was dripping.

I could feel his hard dick tap-tap-tapping against my stomach. I lowered my hands and played with he tip of his dick, feeling the precum between my fingers. I couldn't reach much more due to the position we were in, but I had to do something with my hands.

I groaned and pushed his head up, taking his lips in mine, I turned around and pushed him onto the bed. I continued to kiss him deeply, and then I lowered my self, kissing his cheeks, his chin, his neck. I took my time at his nipples, biting and licking My hands following where my mouth had just been. My hair and my breasts teasing his flesh as they passed over. I nipped at his sides a bit, licked his belly button, and then I paused, letting my tits rest where his dick was nestled between them. I closed my eyes, loving the sensation, and I began to rock back and forth slightly to create a bit of friction.
 
Jack braced himself on his elbows and watched Bailey slowly and deliciously work her way across his chest and down his abdomen, leaving his nipples hard and aching, his skin burning behind her.

Now her breasts are pushing into his thighs, bulging inwards to press against his cock. He tenses his buttocks and thrusts himself forward. He feels himself sliding against the firm rounded curves of her tits, then the redened hood of his cock appears. Bailey slides down until she can tilt her head and lick. He watches her tongue caressing him, bathing him. She runs it along the sensitive rim of the glans, then takes the precum from it's tip. She slides back up, looks at him and smiles...then down again. She raises herself and allows just the hardened tips of her breasts to graze his thighs and then his twitching cock, his balls...

He groans,
"My God Bailey. I want to fuck you girl...'

Everywhere she moves, everypart of him she touches has begun to itch and burn. Jack is a patient lover but he can't take much more of this.
 
Bailey

"ahh Jack, we have all night" I said back to him, lowering myself until my mouth was full of his dick. I loved the taste of precum, and I let it coat my tongue. I licked the length of him, and then let his slide into my mouth slowly, sucking gently and letting my tongue twirl around the head of his dick.

His hands were in my hair, and I knew he wouldn't be able to take much more of this. I wasn't trying to torture him, just to bring him to the edge of torture. I would be here again, tonite, and then I would take him over the edge. I wanted him to fuck me as badly as he wanted to fuck me.

I cupped his balls in my hand, heavy, and full, I squeezed them lightly, then brought my tongue out to bathe them. I kissed and nipped the inside of his thighs. I licked the area between his balls and his anus, he spread his legs for me.

I let my tongue danse breifly on has anus, as I felt his shiver, he spread his legs wider. I smiled and put my hands on his butt cheeks, spreading them apart. I let my tongue work its way into his ass just a bit, twirling it around and around.
 
Jack had been around the block more than once but feeling this beautiful womans warm tongue moving in his ass was electrifying. Her fingers were rolling his balls around slowly causing deep stabs of aching pleasure and pain to roll through him. He reaches out and grabs his cock squeezing it..pumping it. He arches up! In his wildly cascading thoughts it registers that he wants this woman in his ass...deep in his ass.
A new desire...never before...

Jesus her tongue!
 
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