Date: Fri, 2 Nov 2007 16:17:13 -0700 From: Jay roberts Subject: "The Thousand Dollar John" by Jay Roberts Gay Encounters ****I absolutely and positively request, nay order you to vacant these premises if you are under 18. If you are older and if your delicate constitution can stand a story about two males having sex, then stay and be my guest for a while. I had a shitty youth. My two drug addicts who were supposed to be my mom and pop disappeared when I was ten years old. It wasn't much of a loss, they hardly ever had money for food, and we were kicked out of our room in the old hotel several times for not paying the rent. Those times we lived in abandoned cars. When they left, the county got me into foster homes. I was in five between ages ten and eighteen. Some were good and some were bad, but I always had enough to eat. When I reached eighteen I was out of the system. I tried getting a job, but had very little luck. Sweeping floors and such didn't give me enough to get a place to stay. I began lifting in stores and selling the stuff to pawnshops. That got me another small income. I say small because the pawnshops cheated you, because they knew the stuff was stolen. What finally did me in was grabbing two laptops from a computer store and tearing out, just to be nabbed by a fat security guard in plain clothes who was stationed at the exit. I landed in juvy hall. That was where I met Johnnie. He was a nice looking kid. He told me he was gay and he also told me that he thought I was gay too in spite of my tough act. We used to do some stuff together. You know I was eighteen and horny and he was there. We ended are sex together because he told me that he was in love with me and I just can't stand that shit talk. Incidentally, I know I am good looking. After all there are mirrors and I got eyes. My skin is smooth and white, with pink highlights, like on my cheeks. I have dark blond hair that is all curly and falls over my forehead and shows off my bright blue eyes. I got a nice body too, almost six feet and pretty nice muscles from working out in the little gym here. Johnnie was in the Juvy Hotel because he was a street hustler. I found out how you do this gig from him. I got all the details. For instance, he got $40 for just jerking off in front of the john. Shit I do that everyday, several times a day, for nothing. Then he got $60 for letter the guy blow him. He claimed he never gave head, but I think he was lying 'cause he sucked me off a lot. Anyway he said that you could figure on about $200 a night. Now that was the kind of money I'd like. I stationed myself in the area he said the johns go to. He said mostly they drive along slowly and size you up and motion for you to come to the car and then you setup your deal. He warned me never to let anyone get my ass. Funny thing happened the first night. There were two other hustlers. They were also young, but in their mid-twenties I'd say, but you can't be sure. All cats look good at night. These two guys came up to me and asked if I was going to operate on this street. "Why you ask?" "Because you are too much competition with that hair, face and body. Look we chipped in ten dollars if you will go a few blocks away." That was really a laugh, but it made me feel good that they were worried about me getting all the business. I told them to fuck off and that they should move. Well I had a lot of business. It was fuckin' easy. I jerked off twice the first night for two different old cats, and that was $90 in my pocket cause one guy tipped me a tenner. Then I got sucked with a condom on and I got a hundred dollar bill. The next night is when the amazing thing happened that changed my life. A Rolls Royce auto came into the street. I never saw one, but one of the queens told me what it was. A uniformed chauffer got out and came right up to me. He spoke funny, I think he was English. "Young man, how would you like to make one thousand dollars tonight?" I figured he was nuts, but as he talked more, I could see that he was serious. He told me that his master's grandson was interested in trying male to male sex for the first time and the master asked him to obtain a nice looking lad for him to, er, play with. I guess I was picked to be a toy boy for him. Frankly for that kind of money I'd do almost anything, except involving my ass. I said okay. I got into the back seat, sank into the soft leather and relaxed. The driver came into the seat with me. Uh, uh, this was the john. The story was crap. But then he said, "I must tell you more about the job tonight. First off I must blindfold you so you do not know the location of the house. Secondly, when you arrive and are escorted to the guest room, room, you will be required to shower and then be checked by Dr.Finch. Do you agree to these terms?" "Sure, I don't mind the blindfold. It's like a pirate adventure. And I've been stuck by doctors too many times to remember. Shower, good, I need one." After a ride of about 45 min. I knew we had arrived at our destination. I felt the limo turn sharply and then the sound of crunching gravel. The flunky opened the rear door, grabbed my arm and led me up to the front door. Once inside he removed the blindfold. Wow, what a place. The entry room I was in was all marble and had pictures of old gents leading up the stairs. It looked as big as the Met. Museum I was in once. "If you will wait here a moment, I will announce you to the master." He returned and resumed his nasty habit of grabbing my arm and pulling me along to another smaller room. This was lined with books. Suddenly I realized there was a man sitting behind a desk. Crap, he was old, maybe a hundred years or so. He had more wrinkles than a fat ladies corset. He was smoking a big cigar. Suddenly he cackled, "What's your name young man?" "Billy," I told him. "Well Billy you sure are a young looker. My chauffeur did well. Of course we have to get you cleaned up and check out, but I think you'll do well. Now you have an idea of why you're here. For one thousand dollars you are to allow my grandson, Cliff to experiment with you to see if he is really gay. I believe that he may have confused boarding school fumblings with real sexual preference. But after tonight, we'll know. Now here is your money." He handed my a leather wallet. Inside was ten one hundred dollar bills. "Thanks," I said. "Now let's get started. I sure your little boy will be ready to jump me when he sees me." Again that fuckin' chauffer grabbed my upper arm and pulled me up a long flight of stairs and stopped in front of a heavy wooden door. He selected a key from his big key ring and pushed me in. "Shower. Don't miss any parts. Doctor will be along shortly." This was the most beautiful room I had ever seen. Books of all description lined the walls. There was a big double big with silk sheets, now lit from the gooseneck lamp next to the bed. The rest of the room was dim. I took off my clothes. Before going into the marble bath, I stopped in front of the full-length mirror. I took in my strong chest and narrow waist. I turned and looked over my shoulder, there was my hard muscled ass and between the pear halves, my ass slit and ass hole, private property, no entry. What a bathroom. The shoulder had six outlets that sent needle sprays all over. I found the perfumed soap and lathered myself so thoroughly I looked like a snowman. There was special English shampoo and I scrubbed it into my scalp and washed my blond, curly hair twice. Lastly I tenderly pulled back my foreskin and washed underneath. My hairless balls got attention as well. Finally I stepped out and grabbed the giant, fluffy towel left for me. Shit, what luxury. If I left now, it would have been worth the thousand dollars. When I emerged from the bathroom, after taking a crap and piss, I found an outfit waiting for me. What an outfit! It was really doctor's scrubs, white pants, white blouse and white canvas slippers. I looked like the Good Humor man. I was just about to take a lie down on the bed when I heard a key rattling in the lock. Driver guy opened it for a doctor type. He was real old and slightly bent. He had a black bag with him, what else? Get undressed boy. "Hey I just got dressed." He didn't answer. I shrugged and complied. I stood in front of him. He just leaned down and picked up my baloney and squeezed it gently. If he wasn't so old I might have thrown a boner, but instead it shrunk. "It looks healthy," he muttered. Then he took a hypo out of his bag and withdrew a small amount of blood. He poured it into a small test tube and added a regent or some pink stuff. He shook the tube. It remained the same. "Ah good, no STD. You are prime beef and I put my seal of approval on you as soon as I speak to the old man." He left. I lay down on the bed, it was so soft and smelled good, and the room was so pleasantly warm. In a moment I was asleep. I was awakened by the sound of a young voice speaking into my face. "You certainly are hot looking. Charlie the chauffer ought to work for "Play Girl" Magazine. Of course I am only seeing your head. I wonder what the rest of you looks like and I am sure I will find out." So this was the shy boy who didn't know whether to sit to piss or not. He seemed pretty bold to me. I checked him out. He was a typical sixteen-year-old preppy schoolboy. He had one or two pimples, but not enough to mar his pale, smooth complexion. His nose was a little long, but I like that. His hair was straight and cut in a bang across his forehead. His best feature that I could see was his great height. I'd say he was about six feet six. If he was that tall at his age, he might yet be a giant. I glanced down at his feet. Wow, they must be size seventeen. He caught me looking and laughed. "Yes, you guessed right." We stared at each other awhile. He had such a nice red-lipped mouth and when he smiled his teeth were pure white and perfect. Finally I said, "You want to play?" "I do, if you do, otherwise forget it." I waited, hoping he would turn back the covers, but he just stood there swaying slightly. I could see there was a slight bumping in his crotch. He smiled, seeing where I was looking. "You want to take it out?" "Usually I am the one who gets talked into sex, but since I am so well paid here, I guess I might as well make a move." I threw the covers down and then put my hands on the hem of the shirt and in one motion pulled it over my head. I distinctly heard a release of breath as my chest came into view. "Nice chest. Nice muscles for a gay boy." "Gay boy huh? I don't mind you saying that to me, at least I get paid for it. You suck cock for free, maybe take it in the ass." "Never the ass, but I fuck others." I decided to make another move to get things going. I was beginning to warm up to him. He had a nice deep buzzy voice that was vibrating my testicles. "Take off your shirt." "You want my shirt off, you take it off." I got up out of the bed and stood next to him. I was in those medical pants, otherwise naked. I took hold of the front of his shirt and slipped my hand under the row of buttons and pulled sharply. It ripped right down to his cute, white belly and exposed his inny. He was shocked at the violence and I saw that his eyes watered slightly. "You fucking ruined my shirt you street bum." "You got enough money to buy a thousand shirts." I reached for him, put my hand on his damp, hot, smooth back and pulled him toward me and put my full lips against his pink ones. He narrowed his lips to a tight line. I press hard and pushed my tongue through the tiny opening in the middle. In a moment we were kissing wildly and his boy-tongue was making love to my tongue. We separated, both breathing hard. "So what. Is that supposed to make me beg for you to have sex with me." He said, tossing his bangs cutely. "You might as well beg. I don't beg. You paid for me. You might as well get your money's worth." "Get on the bed and take off your pants." "I say the same to you. If you want them off, take them off, rip them if you want." He grabbed the waist and pulled them down. My long, slim, cock, still covered by the foreskin came into view. It was semi hard and it found a berth on my belly. "Stroke it boy. Enjoy your toy." He pulled off his shoes, pants and underwear. Shit, he had a great cock and balls. It was cut and long. He erection was starting right in front of me and that was hot as hell. His enormous ball sac hung down about six inches. This boy was full of cum. He shook his body making his cock swing side to side. "You want some? Go for it." This was a standoff. I had to think what I wanted out of this. I didn't have sex for the pleasure of it since my friend at the Juvy, but this boy was super sexy and his total control of himself and the situation had to be broken, otherwise I would come out as the girly one. Then he made a suggestion that that deep voice. "Hey, do you smoke?" "You mean dope? You got any?" "Yeah, watch." He took a book out of the bookcase and opened it. It's pages had been cut to leave a big empty square in the middle and it was filled with about a dozen thin Js. He took two out and we both sat on the bed and he lit both and handed me one. Then he turned a switch on the lamp. "That's reverse fan. The smoke goes into the flexible arm of the lamp, down and then out between floors to the outside. I had it build last year. This is my tea room here." I toked plenty, but this stuff was dynamite. I guess rich kids can get the good stuff. We each drew a deep first breath and held it. The kid was very experienced. The smoke exploded out of both our mouths. We searched each other's faces. Suddenly he broke into a grin. It made him look like a ten year old cutey. "Some shit, huh?" I nodded. We took puff after puff. His eyes were getting a little red and his smile was crooked. I know that my face was getting numb and that struck me as hilarious. I fell back on the bed and rocked with gales of laughter. "You are s-o-o-o high," he said nodding wisely. "And you straight. I bet you can't even walk straight," I told him. "Hey," he said, "Want to cannonball?" "Okay," he took the final drag that was rich with oils and then did the same to the my roach and threw them in the ashtray. Then holding the smoke he pressed his lips on mine and my mouth opened to take in the personal delivery of smoke. It went from his lungs into mind. He put his arms around me and we sailed off into a dope hazy. "That was good," he said. "You're a good doper buddy. Hey" he said slurring his words, "You ever been rimmed?" "What's that." Funny that he should be more experienced sexually than me. "I'll show you. Don't be nervous, you'll love it, everyone does. Get on your elbows and knees with your ass sticking out." I got into position with difficulty I was so wasted. Once there I felt the ventilating system blowing across my naked as and gooseflesh was playing on each cheek. I felt very vulnerable. I waited, then I felt his breath on my ass crack. I couldn't help it, I let out a soft, "Oooooo." "I told you, you'll be a happy boi soon." Then I felt his tongue lick up and down my ass crack. "Oh shit, that feels good, but you are a pig boy." "I love doing it. You'll see why soon. Hey you got some cute hair around your asshole." Next I felt him lick that hair. Back and forth his insistent tongue lashed my pucker hole. I knew I was "ooing and aaahing" like a fool, but I couldn't help it. I wanted more of that good filling. Next he must have rolled his tongue into a little prick and inserted it into my asshole. I moaned loudly and began to fuck back at that tongue. "Yeah blondie, you're getting with the program. Here take a sniff of this. He had taken a little brown bottle out of the drawer of the night table and took a deep sniff of it and then held it against my left nostril. In a moment I went into orbit. My brain was whirling around the room. Then he did the same to the other nostril. While I was spinning, he put his finger into my ass and jiggled it gently. "How's that feel?" "Excellent, let me take that finger home to use." But then he moved it further in and began a slow massage of my boy clit. I knew about that spot, but had no experience with anything to do with it. "Oh Cliff, do more." "How about this bottom boi." He put the head of his dick into my asshole and held it there. It this what you want blondie? You want your male cunt fucked?" I squeaked out. "Shut your mouth and do it." I was lost to his dominant personality and I knew it. I had saved my ass, perhaps for this boy. "Do what girly? Say it Billy bottomboi." I whispered in defeat. "Fuck me Cliff." "I will if you say it louder." I shouted it and as the sound died away his prick entered me completely until I could feel pubes against my white ass. He pulled out and pushed in. I was crowing like a fool, totally at his mercy and loving it. "I think you are ready for a real fuck now." He pulled back again and slammed in hard. Over and over he did it. "Now I am going to turn you over. I want to see your gorgeous face as you slip into the cum of your life." He pulled me around and lifted my legs and put them at his hips. Then he reentered me and fucked me with a steady rhythm until I was almost senseless with electric feels running up and down my body. My balls were pulled up on either side of my cock shaft and they were vibrating with impending orgasm. Cliff fixed my eyes with his. He knew that a was virtually his sex slave at this moment. "Okay you hot ass kid, I know you want to spew. I'm close too. When you feel my hot cream hit your insides then you have my permission to slide into your cum. Do you hear me?" I grunted yes. He began a slower, luxurious fuck. It seemed to rub everywhere inside of me. "Ooh Billy, here comes the soup. It's hot. Get ready." And sure enough his body began bucking and my insides were bathed with heavy cream as his eyes rolled upward and he gave loud grunts in time to his spewing. I hardly realized that he set me off. My cock began hosing my chest with heavy cum shots. Over and over I heaved out cum cries and spooge. At last we finished. He kissed me. "You're a good fuck kid and you never knew it. I'd like to keep you around. What say?" "Sure, but first, please, need sleep. I'm fucked." "You sure are. You deserve it. Here let me get in with you." He put his long arms around me and I put my head on his young chest and we both hurled into a dreamless sleepl End