The Prostitute & I

June 2, 1999

My name is Claude Simmons for those who are wondering. Last week I got to recollecting my sex life and decided it was pretty decent. Good enough to write about in fact. Reviewing my life this past week has been exciting, and now I want to share these stories with some strangers. I'm going to tell these erotic tales to the best of my abilities.

I was eighteen years old when I lost my virginity. I know that's kind of old, but I was never really the type of guy who liked girls all too much. I preferred a good book and ESPN over tits and ass. Thinking about it now, I can't believe I was that kind of geek. I was an honor roll type student who didn't try hard enough. School was a constant bore. My life was heading nowhere and I was traveling that path at one hundred miles an hour. Things seemed very bad at the time. I searched for that bright spot at the end of the dark tunnel, but I could see only darkness. Many times I did contemplate suicide. If all a person could enjoy in life was books and sports, then there really was no point in torturing myself with life. By the time June 1st rolled around I had developed a nice sized gut, flunked my senior year and lost most of my self-respect. The darkness was getting heavier. The next day, June 2nd, my birthday, I found some light.

Her name was Kitty. If she had any other name I never learned it. I met her at a bar where my father was working. She was sitting at the end of the bar talking to two drunk guys. The two guys were black, one tall, the other fat and short. Nothing about her caught my eye at first. She was about forty years old. Her face was decent, but not astonishing in any romantic novel way. Her hair was bleached white and cut really short, she wore dark red lipstick and baggy clothes. Her face was too white and her were big and hazel. I couldn't tell if she had a nice body or not, the clothes she wore were that baggy. I did see her expensive leather boots though. Her feet were really small from where I sat.

I was sitting on the pool table of the bar waiting for my dad's shift to end. Every night at eleven o'clock it was my responsibility to pick him up from work. Usually I arrived at the bar early. I remember sitting on the pool table looking at my watch and seeing that it was only ten-thirty. The bar was empty accept for Kitty and the two black gentlemen. The owner, a man they called "the Dipster" for some reason, was in the back. The back of the bar was his home. I felt absolutely miserable. It was my birthday and I was sitting in the smelliest bar in Chicago wanting to impale myself on a poolstick. At least at home I could've been reading a book. At the bar I wasn't allowed to bring books. My father didn't want any of his drunken friends to know that I was some kind of nerdy freak who was afraid of pussy. In many ways I blamed my pathetic life on my wife-beating, beer abusing asshole for a father. He was never there for me and when he was he came with a belt and beer breath.

The time passed slowly as it usually does when you're not having any fun. A new customer had dropped by, a man I knew. His name was Kyle. My dad and Kyle went to school together. I watched them from the pool table. Kyle walked behind the bar and shook my dad's hand. It was the lamest greeting in the world. He handed my dad a yellow envelope. My dad opened the envelope and took out what appeared to be pictures. My dad wasn't into pictures, he never looked at our family photo album once, so I was a little surprised to see him show so much interest in these pictures. After he'd looked at each picture he put them back in the envelope. Kyle helped himself to a free beer and began sipping it. It was ten-forty.

At ten-forty five my dad gave Kitty and the two black gentlemen refills. They paid him in quarters and my dad pocketed the money. The Dipster was born drunk and most of the brain cells had burned out long ago. My dad made more money as bar tender than the Dipster did owning the bar. My dad took about sixty percent of what the bar made on a given night. I never saw a penny of it. I worked at a little grocery store after school to make my money.

My eyes burned and the smell of beer and smoke was burning was nostrils. I had an urge to walk out the bar and drive off, but I wasn't the rebellious type. Kyle and my dad walked toward the pool table and gave me a discouraging look. It was my dad who spoke first. He was drunk as usual.

"Move out the way, peckerhead," he said. "Me and Kyle here is goin to play pool for a while." I got off the pool table and watched them set the game up. Neither of them spoke while they played. Kyle won the game easily. My dad broke the stick over his knee. He was a sore loser just as much as he was a drunk. Kyle set the balls up again. While he did so, my dad came over to me. He handed me the yellow envelope of pictures he looked at earlier. "Instead of sitting around looking like an idiot, take a look at these. And for Christ's monkey don't embarrass me." He walked away.

I walked away too. I went to the bar and sat down on a broken stool. I put the envelope on the bar and just stared at it for a while. I turned around and looked at Kitty at the end of the bar. She was drinking her beer. The two black gentlemen were pretty much ignoring her now. She looked as depressed as I felt. When I'd first arrived she was laughing and chatting away like a little school girl. But that had all been an act. Kind of like the make up on her face that made her appear youthful, the beer had disguised her sadness with a blissful cheer. Now that the two black gentlemen had forgotten about her, the world had closed around her once again, and not even the beer could bring back her smile.

I turned away from her because looking at her was like looking at myself. It was ten-fifty by then and my patience was drawing near an end. I opened the envelope only to pass the time. I reached into the envelope and pulled out the pictures. The first picture in the stack was of a young woman. She was completely naked and had a finger shoved in her pussy. She was laying on a bed with her legs spread out and a smile on her face. The picture was black and white. I turned toward my dad who looked at me with a discontented frown. Than I looked at Kitty. The woman in the photo looked something like Kitty. Only younger. I kept looking from Kitty to the woman in the picture. The more I looked, the more similarities I saw. They both had the same long chin. They both had the same button nose. They both had the same little ears. The only real difference was the woman in the photo had long hair and Kitty's hair was short. And of course the twenty year age difference. Could this be Kitty when she was younger? I wondered.

I looked at the rest of the photos. They were all pretty much the same. The young woman in the photo posing completely nude. Doing a split with her long legs, doing a cartwheel, or just laying around with a thumb in her vagina. I counted over thirty-five pictures in all. By the time I was done looking I was sweating. I turned around to look at my dad's pool skills, but instead saw him face to face. He was there in front of me, looking insane and smelling foul.

"What do you think, son?" His words were so badly slurred I barely understood him. "Nice pussy, huh."

"Yeah," I agreed almost blushing.

"That's Petra," he said. "You see that whore down at the bar frolicking with them niggers. That's Kitty. Petra's younger sister. Petra would fifty something today, flabby, ugly and have pillow for a pussy. Kitty ain't bad though, for a whore." He patted my back. This was the only way I could bound with my father, which is why we never talked.

"I used to climb up an old oak tree to watch Petra undress," my father continued. I was nine then, Petra was maybe fifteen. Kitty was six. I enjoyed those nights a plenty. Kitty and Petra were like twins born nine years apart. I fucked both them. I took Kitty's virginity. She was a freshman in high school than. Petra took my virginity when I was a freshman in high school. Funny how things work out, huh boy?" He patted my back once more and walked away. It turned eleven as I finished putting the pictures back in the envelope.

I didn't think of Petra or Kitty much as my dad closed the bar down. Kyle and the two black gentlemen had left and Kitty was dancing her way out the back door. She was the drunker than my dad. I watched her walk and wondered if she was going to trip over her own two feet. She didn't. Kitty managed her way out the back door. "Bye," my dad shouted. And when she was gone he added, "you stupid nigger loving whore." My dad was quite the racist. He hated everyone that wasn't drunk I guess. He was German and Irish and he hated blacks, Mexicans, the Polish, the Italian and just about everyone else. He even hates the Irish, he won't even claim himself to be Irish.

"Go start up the car," he yelled at me. "I'll be out there in a fucken minute. I have to shit like a bitch."

I was more than happy to get out of the bar. Only my tired legs prevented me from running out of there. I went out through the back door. The air was fresh and the night's wind was cool. The moon was shining over a green house across the street from the bar. I walked over the 95 Corolla. It was a blue model. The front was bashed in from an accident my dad had with a pick-up. I guess he's unlucky to be alive. I am anyway. I walked over to the driver's side of the Corolla and there I saw Kitty. She was inside of the car talking to herself, about to cry. I opened the car door and asked what she was doing.

"Waiting for you," she said. Her voice sounded defeated. She was holding a very wrinkled hundred dollar bill in her hand. "I'm waiting for you," she repeated.

"Why?" I asked. I wondered why this older woman would be waiting for me inside my car. How had she gotten in? The car was locked. Why did she wait for me? Why was Kitty crying? Holding a hundred dollar bill?

"You mean you don't know." She sniffled and looked up into my eyes. Her hazel eyes were the most beautiful I'd ever seen.

"Do I look like a person who knows what's going on?" I asked. We both laughed a little. I could smell beer on her breath.

"This is a lot of money," she said. "Worth fifteen customers." She scooted over to the passenger side seat. "I hate my life. I hate what I do. But I need the money. Climb in champ. Your dad ain't coming out of there for a while."

I looked at the bar as if to prove her wrong, but the back door remained closed. "What's going on?" I asked.

"I'm your slave for the night," Kitty said. "Happy birthday slugger, your dad bought you your very first prostitute."

***

We drove around for about fifteen minutes. We talked for a while. I was nervous being around a woman who was paid to fuck me. I was also nervous because I knew that if I wanted sex, I could have it. So I kept the discussions away from sex, or at least I tried.

"I can't believe this," I said. "Why would he do this?"

Kitty was still looking her hundred dollar bill. She was smiling now. "You are nothing like your father. Fifteen minutes alone, shit, your daddy would have fucked me three times."

"Sorry," I said. "I try not to be like my father. And I usually don't chat with any prostitutes." The comment shut her up, but didn't wipe the smile off her face.

"I think it's a good thing. Your father isn't the greatest man in the world." She put the hundred dollar in her boot. "Are you afraid of me, slugger?"

"Why are you calling me slugger?"

"Nervous tension, I guess. Your a fresh eighteen year old. You've been eighteen for what-"

"Ten hours-"

"-I never got paid to sleep with someone so young. I haven't did an eighteen year old since I was fifteen."

"I won't jog your memory tonight. My dick stays in my pants." I blushed again for talking in such a vulgar language. I was pissed at my father and angry at Kitty because she was helping him win. Why did she have to agree to the deal? She needed the money, of course. Still, I wasn't in any shape to offer Kitty satisfaction. I was a virgin. I was almost suicidal. I was running through a red light.

"Red means stop."

"Thanks for the driving lesson," I said. "Do you have a home or do you live in the streets?"

"Why do you care?"

"I'm dropping you off. I can't do this. I'm a virgin and just don't feel right losing it this way. It sounds so stupid, but believe me I don't feel stupid. There's a lot of things in my life I have to fix, so I'm not worried about sex."

"The whole world seems depressed when your depressed," she said. It was the last thing I'd expected to come out of her mouth. "I've been living life on the wrong path for a long time now. Too late to change. I'm glad I met you though, kid. Until now every man I've ever known has been drunk and abusive. Your not either of them. Just trying to find your way."

"Yeah," I agreed. "Away from my house." We laughed. "Nothing personal. I think your a pretty woman, even though you're old enough to be my mom." She looked at me with a phony evil grin.

"Thanks," she said. "Park here." It was an empty parking lot. I drove into it and parked at the back of dark empty lot. There were stores all over the place, but none of them were open. The parking lot belonged to plaza. There were all kinds of stores around here, most of them private businesses.

"Why did we come here?" I asked. She opened the car door and stepped out of the Corolla. I thought for a moment about leaving, but decided to go out and talk to Kitty. I opened the door and slammed it shut. Outside the air was a little cooler. The stars were shining in the heavens. They glittered like I'd never seen them before. Chicago wasn't the place to be if you wanted to see the stars, but this location was different. "Hello!" I shouted and my voice echoed.

"This is my favorite place in the world," she said. "Sometimes I come up here at night and watch the stars. All by myself. I never take anyone up here. Looking into them stars makes me forget about my life. Sometimes I can imagine myself being a movie star or a princess and not some low paid hooker." She sat on the hood of the car. I sat next to her.

"I'm flattered you'd show me a place that means so much to you," I said. We both laid down on the hood of the car and watched the stars. The lot was empty and we could listen to each other breathing.

"You're my favorite client," she said. "I never got your name though."

"Claude," I said. "Claude Simmons."

"I'm Kitty," she said. "But you probably know that." We looked at the stars for at least ten minutes. During that time I must have forgot that this woman was twenty years older than me. We began holding hands and talking about bad times gone by. We didn't fall in love or anything like that, we just became friends really fast. Like little kids meeting each other at the park. We became close quickly.

"When I was a little girl I used to throw water balloons at your father," Kitty told me. "He used to spy on my old sister, Petra." She told me a lot of wacky stories. "I was a waitress before I was prostitute. That's how found this business. My boss paid thirty bucks to suck his...penis, and well I did, and decided it was easy money. And it is, but it also deprives you. It makes you feel worthless."

I talked to her about my life. I told everything I could. Secrets I will not even mention in the story. And for once in my life I could see light at the end of the darkness. Kitty rested her head on my shoulder and I felt her tongue flicking my neck. I felt her hand pressing against my crotch. The flicks turned into kisses.

"What are you doing?" I asked.

"For once I'm not thinking like a whore," she said. "I'm thinking like a woman. You are the closest thing I've had to a friend. But I won't you. I need you. And if your my friend you won't reject me."

"But I can't."

"Yes you can," she pleaded. "I'm paid for. If you can't love me as a friend, then take me as a whore." She pulled off her bag shirt revealing her round, firm breasts. She was forty, but she had the body of a twenty year old. She kissed my lips and finally I kissed her back. My cock was growing too. For the first time in three weeks I had an erection. Our breathing got louder. She climbed on top of me. We continued to kiss. I explored her amazing body with my hands. "I love the way your hands feel," she said. "I love the way you make me feel."

My heart was racing. I could smell the beer on her breath, but the night made the smell more pleasant. I pinched her nipples and she let out a soft moan. Kitty helped me out of my shirt and began playing with my nipples. The night breeze felt good against bare chest. I grabbed her breasts and slowly began bite and suck on her nipples. I felt her soft hands on my back, rubbing up and down.

Kitty began working her mouth down my throat. I felt her tongue all over my throat. She moved down to my chest, then to my stomach. Her tongue dissolving the depression away, at least for the moment. I felt Kitty unbuckle the belt on my pants and slide off. She unbuttoned my pants and slid my pants off my legs. The hood of the car was cold when my touched it. She removed my underwear too, allowing nine inch erection to become free. The wind froze the pre-cum oozing out of the pisshole. It felt incredible. She touched my hard flesh with her soft hand.

"This is the most passion any prostitute has ever felt," Kitty said.

"Is it?" I asked out of breath. She was stroking my cock.

"Oh yeah. Not to many men can make a whore feel like a queen. But you have. You're the sweetest, kindest man of them all. And you've only been a man for ten hours."

"If this is the greatest prostitute-client relationship ever, where does Richard Gere and Julia Robert's role in "Pretty Woman" rank."

"Just below this," Kitty said.

Kitty licked the tip of my penis with her tongue. She did like an artist using a paintbrush, in slow, even strokes. She was still giving me a hand job. My eyes were sinking into my head, or so it felt. I watched her lick up my pre-cum and it turned me on more than thing in the world.

"You think Julia Roberts did this for Richard Gere," I asked Kitty.

"In the uncensored version of the movie."

"Do you think Julia Robert's was any good?"

"Sure. But not as good as me."

As if to prove her point she took my nine inch cock in her mouth, almost deep throating my entire length. She let cock rest deep in her throat for at least thirty seconds, then she slowly start moving up. I felt her sweet tongue licking all over my shaft. I got to thinking of Julia Robert's deep throating Richard Gere and my cock got even harder. It felt hard enough to crack. She grabbed on to the bottom of my cock and continued to jerk me off, and sucked the top of my cock, giving me a blow job and a hand job at the same time. I could only look at the stars. Every once in a while I'd find the courage to look at Kitty bobbing her head between my legs, but not often. She squeezed my balls in her right hand, while she stroked me with her left. My head was against the windshield, her feet were dangling off the car. Her stomach and breasts were pressed against the cold hood of the car.

She slid off the hood of the car, but kept one hand on my cock. She wiped some saliva from her lips and smiled at me. "I love your cock, trooper." She had so many little boy names for me. I think the fact that I was eighteen turned her on. She let go of my cock. She bent down and took off her leather boots, then slid down her pants. She slid three fingers into her wet pussy and let out a soft moan. I leaned against the windshield and watched her masturbate for me. In the background I could see all the empty, dark stores. And further down I could see the sky and the stars. Kitty masturbated in the moonlight, under the stars she loved so much and I could see the sense of freedom in her eyes. The show lasted three minutes. I don't think I missed a second.