2 comments/ 53808 views/ 11 favorites The Prostitute By: Bones Malone Josh walked slowly down the city sidewalk. It was late – one o' clock or so. His heart was already racing somewhat, which didn't surprise him. Josh had never done anything like this before. He had downed some vodka earlier to help him calm down, even though he wasn't much of a drinker. Obviously it hadn't worked too well anyway. But he was finally going to do it. He had made up his mind and now, the time had come. He rounded the corner and saw them, about a dozen or so, all looking rather bored. Josh knew that whichever one of them he ended up with wouldn't be bored for long, because he doubted that he was going to be the type that they usually dealt with. He saw that one of them was sitting alone, away from the others. She looked rather young to him. He figured she was about 22, yet she looked quite experienced in spite of her age. She was pretty small, but built quite nicely, which, Josh figured, must be one of the requirements for the job. He decided he wouldn't find anyone better, so he started heading in her direction. Josh was so nervous. He didn't even know how he would begin, but there was no turning back for him now. He stopped a few feet away from her. She glanced at him briefly, then turned away again. Josh was shocked; he didn't know a prostitute could be so beautiful. He wasn't sure if this fact would make it all easier or harder. "Well," Josh thought, "here we go." At last, he spoke, "How much?" She was filing her nails. Without looking up she replied, "Depends. How much have you got?" Josh checked his wallet, "About 120." She looked up finally. She seemed to be calculating in her head. "That could get you a pretty decent blowjob, with a few extras beforehand." Josh could already sense movement in his pants. "Uh… extras?" She smiled at him. "I could introduce you to several of my body parts… if you get on my good side." Josh felt very warm rather suddenly. "Ok," he managed. Without a word, she got up and began heading in the opposite direction. Josh's feet seemed to be stuck to the ground. She turned around, "Coming?" He finally started to walk. They turned into the building they had been standing in front of and started climbing the stairs. Josh's mind continued to race, "Oh God, what am I doing here? I must be crazy." Before he knew it, Josh was standing in a small hotel room, and the woman who had brought him there was sitting on the bed, taking off her shoes. It was all happening so fast. "Wait," Josh said, "can't we just talk a little first?" The young woman looked rather surprised. "Interesting idea. What do you want to know?" "Well… what's your name?" "Forget it, mister; names aren't important here." "Well how old are you?" "I'll be 20 next month." Josh's mouth dropped open. "What about you, mister?" "I'm… 31." "Ok, good for you. Do you want me to suck your dick, or what?" Josh wanted nothing more than to have this beautiful young thing suck his dick, but there was still more to be said. He wondered what would be the best way to say it. "How often… have you done this?" She laughed a little. "Wondering if I'm qualified? I've had sex 1428 times. How's that for qualified?" Josh sighed. The time had finally come to tell someone. "Well… the thing is… that's 1428 times more than me." It took a few seconds to sink in. When it did, the girl said, "Wow. And you've got eleven years on me. Now that's ironic." Josh was amazed how well she took it. He figured after 1428 men, nothing surprised her anymore. "Well we'll have to change the plan then, won't we?" she said with a smile. Josh's heart skipped a beat. "Come sit here," she said. Josh sat down on the bed as she got to her feet. He couldn't seem to keep his legs still. "Oh you poor thing. Try to relax, ok? I'll take care of you." She stood in front of him in an outfit that was barely legal to be worn in public. She stripped off all her clothes with Josh watching in awe. She turned around until she was facing him again. She held out her arms, displaying herself. "You like?" she asked. Josh saw that she had so many wonderful curves. He found it difficult to think clearly at all. "Yes. Of course. God you look amazing!" She knelt down in front of Josh and began opening his pants. Josh was burning with anticipation. The young prostitute found his cock and quickly put it in her mouth as if it were a melting Popsicle. It felt more wonderful than Josh could've imagined. Her well-trained tongue and lips were so very soft and smooth. Josh was glad that he had shot his load earlier that day so he would last longer now. While continuing to lick his dick in long, slow strokes, she asked, "Ready now?" "For what?" In a whisper, she answered, "For… my… pussy?" Josh was sure his heart would break through his chest. He nodded his head to show that there was no doubt. She helped Josh out of his clothes and onto the bed on his back. She straddled his legs and slowly guided his wet cock into her pussy. "Finally where it belongs," she said smiling. She placed her hands on his chest and started riding him. "Put you hands on my butt, sweetie," she said breathing more quickly, "I know you want to." Josh wasn't about to deny an invitation like that. He reached out and felt her soft, round buns as his penis pushed deep into her. He moved his hands up to feel her big, beautiful tits with their hard nipples. "I'm glad you're finding your way around," she responded. Josh wondered if it was all right if he were to cum inside her. As if reading his mind, she said, "I want you to cum into me. We want to be sure that this fuck is legitimate after all." Josh managed a laugh although he was breathing hard now. She was riding his dick faster and faster. He grabbed her ass and pulled her further into him as he came powerfully inside her. The young girl climbed off, opened her legs wide (giving Josh a great view), and began fingering herself quickly. Josh could tell that she loved to be watched, and he, of course, loved watching. Instinctively Josh milked his own dick while watching, causing the last of his cum to dribble out. After massaging her pussy for several minutes, the gorgeous young woman came at last, causing some of her own juice to drip from her. "That was wonderful," Josh exclaimed, "you can be sure I'm never going to forget this." "I won't either; how could I forget my 1429th?" They both laughed. "But really," Josh said sincerely, "you were perfect the way you handled this, and I'm really thankful for that." "You're welcome, mister. I'm glad you picked me." "Me too." Josh left the hotel after paying and walked down that same sidewalk, a new man this time. 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. The Prostitute & I Kitty put her boots back on, the one hundred dollar was being held in one of them, and climbed back on top the hood. "I need more cock," she laughed like a school girl. She began sucking me like before. I maneuvered her legs around my neck and looked into her soaking pussy. "Taste if for a for a friend," she begged. I'd never even dreamed of doing such a thing, but I was tempted. I stretched out my legs because do that when I'm nervous. My feet were touching the pavement. My head was against the windshield. Kitty put her pussy in my face, and I just reacted. I moved my tongue around like dog slurping water. I don't know if I was good or not, but I know that eating pussy made Kitty's blow job abilities all the more better. She was humming a melody on my cock, while fingered, tasted and licked her forty year old pussy. Her juiced dripped all over my face. She was humping her pussy into my face. I returned the favor by humping my cock into her mouth. It was my first game of 69 and I was truly enjoying myself. Than Kitty began vibrating and she came into my mouth. I almost gagged there was so much. My face got soaked, my hair, I felt like I was drowning. Kitty stopped sucking my cock and let the loudest moans I'd ever heard. Her screams of passions echoed for miles. The sound was almost deafening in the empty parking lot. She experienced three orgasms in a row. My tongue never stopped. "Fuck me," she moaned. "Fuck me now. I need it." She straddled her self onto my cock and began riding my nine inch cock. She was so wet it slid right in. I felt her pussy juices dripping all over my cock. The hood was getting dented, but I did not give on fuck. We were making a metallic dink noise that also echoed through the entire parking lot. My cock was going to be thanking me for a long time after introducing it to Kitty's sweet pussy. I grabbed her by the luscious breasts and fucked her pussy with all my strength. She drove her pussy downwards, meeting my powerful upward thrusts. I was so wild that I'd forgotten I was laying on the hood of a car. My neck was aching because it was smashed against the windshield, but just didn't give a fuck. I was enjoying myself too much. Kitty leaned her head down and we began sharing very special kisses. Are tongues met. Her tits and met my chest. We became one on the hood of a blue 95 Corolla. She rode my cock for five more minutes, then she rolled off me. "I haven't had this much fun in a long time," she said. "Your a really sport." She laughed. I rolled on top of her and kissed her soft neck. At the same time I slid my cock back into her pussy. "Do it," she moaned. "Fuck me some more. Show me what you got." I got to my knees and spread her legs. My cock was five inches in. I drove it in the rest of the length. Holding her legs apart, I rocked in and out of her pussy. I did it at a slow pace. Her breasts rocked back and forth in waves. The wind blew against her short white hair. "Harder," she moaned. "I want you to make me scream." "Your wish is my command," I said. I pace quickened. Our hot flesh smacked into each other, making a loud clapping noise. My body glistened despite the cool air. Kitty began moaning through her teeth. My eyes were stuck on the sight her beautiful bouncing like balloons in the wind. "Do you like it?" I looked into her eyes. She looked into mine. The back of her head was crushed against the windshield, but she didn't seem to notice. "I love it, Claude. Fuck me. Fuck me. Oh, your the best friend a girl could have." I smiled at that. Her was a forty year old woman who could consider herself a woman because of one good moment. I felt good for her. I felt good about what we were doing. I felt odd about the situation. My dad pays a prostitute to fuck me, but I don't fuck until I become friends with her. How many other men did that? Was I one of a kind? "I'm cuming," she screamed. And she let go. She had nothing ground shaking orgasm. I felt her body shaking again. I looked up at the stars and closed my eyes. My cock continued to invade Kitty's wet hole. "Fuck my titties," Kitty said. "I can't...I'm too tired. Please, fuck my titties." She was out of breath. Saying them words seemed to take away all her strength. I mounted her chest and slid my cock between her titties. I didn't know how much longer I was going to last. I was getting that sinking feeling in my balls and knew I could be cuming soon. Kitty held her breasts together and began sliding my hard piece of flesh through her tits. I held on to the windshield and looked down at Kitty while titty fucked her. My balls slapped against her flesh. I felt Kitty's tongue lick the tip of my penis every time it passed through. Sometimes I'd surprise and three inches of cock into her mouth. She'd slap my leg for catching her by surprise. "Claude, baby," she said softly. "I want you to cum in my mouth." The very words drove me wild. I fucked her titties harder and was building toward my own orgasm. Her tongue swirled around the head of my cock and I almost burst there. I took my cock from between her titties. I looked into her eyes and told her to get ready. She responded opening her mouth. My cock was two inches from her mouth. She spit on her hand and stroked my cock. Her hand felt hot pressed so hard against my penis. She put the head of my penis into her mouth and sucked like a lolli-pop. It was when her teeth scraped my pisshole that I finally came. My cum shot out of my cock like a rocket. The first stream filled her mouth. Cum dribbled out the sides of her mouth. I came again and again. All of it in her mouth. She swallowed as fast as she could, but she couldn't get it all. I gave three more spurts when I thought I was done. This cum landed on her breasts and throat. Exhausted, I rolled off her. Naked, we laid next to each other for maybe fifteen minutes. "Ready to go," I asked. "Yeah." "This was the greatest night of my life," I said. I wiped my cum from her chin and below her lips. "Thanks," she giggled. "I had a lot of fun too. And next time warn me. You could of drowned me with all that cum, or choked me. You're nothing like your dad, trooper." "I consider that a complement." We got dressed and drove away. I never did see Kitty again after that. She didn't quit being a prostitute though. Rumors were she was shot by an unsatisfied man in black or she moved to Vegas were business was better. I only know one thing. My dad paid for a prostitute and made a good friend, at least for one night. She fell asleep on the drive home. I dropped her off at her house and she walked away forever. When I arrived home I was feeling good for the first time. I'd found some light at the end of my darkness. I had my first sexual adventure. And I was robbed of all energy. I fell asleep as soon as my head hit my pillow. My father never found out what Kitty and I did. But he suspects. My approach was different. Deep down he believes he did good. I know the truth though. So concludes this story. What story could be better. A dad hires the services of a prostitute for his son's birthday. So long for now... The Prostitute and Me I don't exactly know what it was that made me go buy the services of a prostitute. Well, okay, I must admit that the last statement wasn't entirely true. Actually, the truth of the matter is that I can't really pinpoint it. The obvious answer seems to be lust. I could say that the reason I did it was simply that I was driven by the pure desire to have sex, and most of you reading this would believe it without second thought. In fact, if the President were reading this he would believe it without second thought. Almost anyone would. But when I spell out the situation to you, perhaps you will think differently. Because I know it was something else. Something many of you may be able to relate to. I was eighteen and it was the summer before my first year of college. You know the summer: everyone is out raising hell, the school slut finally gets pregnant, all the athletes get DUI's, and all the band geeks finally start screwing each other. A typical summer in redneck Tennessee. Now the way I know I bought the prostitute for more reasons than one is because at the time I actually had a girlfriend. And she was a good girlfriend to have, too. She was relatively intelligent, she was fairly attractive, she smoked a little weed, and, well, she fucked. See, at the time, the number one quality a girl could have was the reputation of having sex with whomever she was going out with. Not just anyone, mind you, because then she would be a slut or whore. But with her boyfriend. Or her steady date. That was okay. Regardless, I was the lucky guy to be dating "that" girl. She did a wonderful job of keeping me happy, too. Friday nights I would take her to a movie, then we'd have sex in the backseat of my car. Saturday's, I would go over to her house and we'd screw on the couch after her parents went to sleep. During the week, she'd come over after school and we'd fuck in my room. The typical teen sexual relationship. My college of choice was Temple. Don't ask me why. A two day orientation was held in the middle of July that summer, and although not mandatory, my parents were so excited about getting me out of the house that they made me go. (They gave me some phony explanation about getting to know the place, but I didn't buy it). So here I was, a country boy pretending to be an intellectual, heading up to a major northern city, with absolutely no clue as to how to live in the culture, climate, and pressure of such an atmosphere. I flew up to Philadelphia one sunny morning via the ticket my parents bought for me. It is a nice city. The air is surprisingly clean, the parks are well maintained, and the city lights up beautifully at night. If you know where to look, you can find some incredible things in Philadelphia. But if you also know where to look, you can find some pretty nasty things. Dope dealers, gangbangers, bums, and... well, prostitutes. I saw them all over the place on the bus ride from the airport to Temple's main campus. Black prostitutes, white prostitutes, Hispanic prostitutes, attractive prostitutes, fat prostitutes- they were all there. I'm telling you, Philadelphia is like a shopping mall of prostitutes. And something about them turned me on. Orientation lasted all day. And, despite what Bill Cosby may have you believe, orientation at Temple really sucks. Bored out of my mind, and fresh off warnings to stay on campus, I decided to go out that night. I decided to go out and just look around. Browse some, maybe. Perhaps, for this reason I cannot explain, do a little window shopping. Nothing wrong with that, right? As soon as I hit the city streets, I saw them all over the place. In alleys, on street corners, in parking lots... everywhere. "Hey baby, you lookin' for some fun?" a brown-haired, heavier prostitute asked me. I didn't respond. I just kept walking. "Hey sweetie," another simply called to me. Again, no response. What was I doing? I was walking down the inner-city streets of Philadelphia after dark, with a slight erection, doing nothing but walking. Why was I doing this? What did I want to see? Finally, after I had pretty much cleared downtown and ignored all the offers and sales pitches, I decided it was time to head back towards campus. I turned down a street that seemed to head in the general direction of campus, and found myself alone on a dark street. I quickly grew nervous that the surroundings were so dead and empty. I picked up my pace and walked past a shabby apartment building. A figure sat quietly on the staircase. I did my best to veer away from the staircase, as to hopefully go unnoticed. "Lost?" a feminine voice asked me. I stopped suddenly, as if caught committing a crime or something. The voice laughed softly. "Obviously," it concluded. "Not really," I responded, not quite able to make out the figure in the darkness, "I'm just roaming." "Roaming, huh? I doubt that." The figure got up and stepped closer to me. I could make her out perfectly now. It was a woman in her early thirties with long, red hair. I was immediately attracted to her, even though she had a trashy look to her. She had blue rings of mascara around her eyes, she wore bright red lipstick, and her skintight skirt looked cheap and worn out. She wore a tight tank top, revealing only the fact that her breasts were teasingly large. I felt an erection slowly coming on again. Could she be? "No really, I'm just walking," I said, which in actuality, wasn't a lie. "In one of the worst neighborhoods in the city?" she asked with a look of doubt spread across her face," A nice boy like you... whatever you say." "Seriously, I'm just walking around." She stepped closer to me, dangerously close, and smiled. "So you bored?" Now, I really got nervous. I don't know why, but this was nerve racking. My erection stiffened. I really wanted to do this... why?? "Yeah," was all I could muster. "Fifty gets you a blowjob," she said and locked her hands behind my head in an embrace, "And for a hundred, we fuck." She said this with a very seductive voice, quite the saleswoman no doubt, and I was hooked. "I've got a hundred," I replied. At this, she took my hand and led me down the street to an alley, which she turned into. "What are we doing?" I asked nervously. "Oh," she said as she stopped walking, "You want a room?" I pondered this and looked at her. "Well, what do you suggest?" She again grabbed my hand, and this time led me halfway down the alley to several wooden crates next to a dumpster. The alley was dark, cold, and unfriendly. The buildings enclosing it were old and seemed uninhabited. "Money first," she said with a very business-like tone. I reached into my jeans pocket and pulled out a small wad of twenties. I gave her five of them, which she counted and recounted. Happy with the payment, she kissed me softly on the lips. But as I went to kiss her again, she backed away. She walked over to one of the crates and summoned me to follow. When I got to her, I again tried to kiss her, but instead, she turned her head away. I started to complain, but before I could, she turned around and bent herself over one of the crates. She reached back and grabbed the bottom of her skirt with both hands, and tugged it up. She wasn't wearing panties underneath, so now I was staring at her bare ass. Although it belonged to a woman at least ten years my elder, it was one of the nicest asses I'd ever seen. Smooth, thick, and very sexy. "Got a condom?" she asked me, not changing her position. "Yeah," I answered and pulled it from my pocket. "Use it no matter where you put your dick," she commanded. "Huh?" was my response. "I don't care if you fuck my pussy or my ass," she clarified, "Just make sure you use the condom." How sexy. I carefully unwrapped the condom, as a gust of wind sent chills through me. She was silent, just bent over the crate, her ass just waiting for me to touch it. So I did. After I unzipped my jeans, let them slide down my legs a little, and rolled the condom on my cock, I touched her ass. I simply ran the back of my hand across her left cheek. No response. "Sweetie, it's getting cold," she said impatiently, "You're not getting scared are you?" "N-no," I stammered, "Definitely not." "Good," she answered, "Because this would be a shitty way for you to lose your virginity." Thanks for the motivating pillow talk, sweetheart. Despite this, my erection was at full strength now, and as I looked down at her thirty-year-old ass and grabbed her hips, I pushed myself inside her. Although it wasn't hard to penetrate her, it was incredibly erotic. Her pussy was worn, but I think that was part of what I wanted. "There you go," she whispered back softly, "Good boy." I pumped my dick into her pussy again and she responded by pushing herself back towards me. The sensations were tantalizing. I thrust forward again, and she pushed back my way. Damn she was good at this. She was looking for rhythm. I thrust forward again and this time she moaned a little. She actually moaned. Something about this sent a spark flying through me. I thrust forward again, this time harder. She pushed back, again moaning. I thrust forward, she pushed back. The pace picked up. Holy shit, I thought, I'm actually fucking her. This wasn't sex, this wasn't love - this was just fucking. I picked up the pace even more, ramming her forward as she drove me back. It was a great motion, my waist and her backside interlocked, rocking back and forth. She moaned again and this drove me nuts. I could hear the crate creak with every motion. I felt myself moving closer to my peak. "Yes!" she moaned, "Fuck me, baby! Fuck me harder!" I began plowing forward harder, now nearly throwing her whole body up on the crate with each thrust. She was loving it. "Oh yeah!" she goaded me, "Do it harder, baby!" The crate was seemingly ready to break as I continued fucking her. She was no longer pushing backward. She was just impaled on my cock, being tossed forward at each thrust. Each time her only response was an "oh." So as my hips continued to smack into her ass, and as I continued to ram my cock into her pussy, all I was hearing was "oh-oh-oh-oh-oh-oh-oh." I was fucking like an animal. Like a beast. Like I was trying to hurt her. That's when I understood what it was. I could never fuck my girlfriend like that, with that force... with that brute, reckless force. But for some reason, some instinct, I had to try it. I had to fuck something solely to fuck it. Solely to dominate it. To show my manhood, to no one in particular, but expect maybe myself When I finally came, I cried out. A series of brilliant spasms shot up my cock, followed by a spray of cum that only the condom stopped. The pleasure was intense as I bit down on my teeth and squeezed my thumbs. For some reason, a conquest felt complete. I collapsed on top of her, breathing heavily. She let me lay over her for a few minutes, as I just stared down at her red hair. "Okay, honey," she finally said, "It's time to go." I got off her and she stood up and pulled her skirt back down. She kissed me lightly and smiled. "You did good," she said. "Really?" "Yes," she nodded. "Did you like it?" I asked. "Yeah," she shrugged, "I actually did." We parted ways a few minutes later, and I would never see her again. Nor would I ever use the services of a prostitute again. Call me what you want it, but I'm still glad that I did it. I mean, it was with a woman I didn't know, in a city I didn't know, and at a time when I didn't care. So why not? Frankly, to this day, it was maybe the best sex I've ever had. Except for maybe that time with the Swedish twins in the jacuzzi. But I'll tell that story some other time!