A Country Boy Goes To The City

I will begin my telling you that the most interesting part of my life was between the ages of nineteen and twenty nine. The rest hasn't been bad, but those years, from 1963 through 1973, gave me experiences that few other guys had been exposed to back then. I started college in Chicago with a small scholarship and a loan and had no idea how I was going to pay my tution, but knew that I wanted a formal education and would figure out a way.

My mother and father lived in rural Illinois and I was happy to get out of the country and into the city. I had been there often, but had never lived anywhere but on my parent's family farm. I knew no one when I arrived and was lucky to meet Orlan my very first day of classes.

Orlan and I hit it off immediately. We were similar in looks, both blonde, too skinny and light-skinned. We have been taken for brothers more than once, even though he is five foot eight and I am only five foot four.

I started hanging out in parks and making money by having sex with older men. I mostly gave them blowjobs, but once in a while, I got fucked. Occasionally, someone wanted me to fuck them. I was okay with all of it except that if a guy was too fat or too tall, I couldn't get turned on enough to fuck him. Fortunately, that situation only came up a couple of times.

I saved almost every cent I made but even though I tricked two or three times a night and three or four nights a week, I still struggled. Orlan had a lot of money and after a few months, I was comfortable enough to tell him what I was doing on the nights that I wasn't at my little one room apartment. He quickly told me that he had a pimp and was making more money than I could ever make out in the parks on my own. He told me it was safer to get his tricks through a pimp and almost everyone that he tricked with was well-to-do and that they were often overnighters that paid really well.

I had never done an overnighter with anyone. I usually sucked someone off in their car or in the park somewhere. When I did go to someone's house or apartment, I didn't spend the night even if they wanted me to because I needed to get back out and try to earn more money before the bars closed and the park cleared out.

Orlan introduced me to Johnny J., his pimp. Johnny J. was a typical black pimp, almost always dressed to the nines with a big hat, colorful clothing, shined shoes, and more than one Cadillac. I was scared to death when he said I would need to go to his place and service him so he could evaluate me to see if there was a place for me in his "business."

I had had sex with a very limited number of black men and they always scared me a little. When I sucked them, most of them had pushed my face down on their cocks making me choke and when they fucked me, it always seemed like they were unnecessarily forceful. But, Orlan had told me that I could make from $300 to $500 a week, which was one helluva lot of money back then. I agreed to go with Johnny for what he termed an "interview."

I rode in his white Cadillac from downtown Chicago to a high rise on the East side and he talked very little as he drove. He make a joke about "white on white" referencing my pale body against the white leather seats in his car. I tried to act confident, but I don't think I fooled him.

It turned out that Johnny J. was completely different than any black man I had ever been with. He was gentle with me and never forced his cock deeper than I could take without gagging. Later, when he fucked me, he was so sweet and gentle that I acutally blew my nuts onto his stomach while impaled on his cock as he lie flat on his back, lifting my small frame up and down as his cock made me moan with pleasure. At five foot eleven, he seemed like a giant to me. Even though I had been with bigger men, I always had a preference for men that were not so tall and muscular.

After I spewed my cum on his stomach, he flipped me on my stomach and fucked me a little harder, but not so bad that it hurt me. His cock was eight inches and thick, but I had taken quite a few that size and bigger by the time I met him, so I was pretty happy with the sex that first time. He took quite a long time to cum after he put me on my stomach, and when he did, I wouldn't have known it except for a couple of loud grunts and a hard push before he stopped, holding himself deep inside of me as he released his seed. He kept me beneath him for more than five minutes after he finished but when he pulled out and slapped me on the ass, he said nothing except that I needed to get dressed so he could "get back to work."

I got no feedback at all from him as he drove me back to my little one-room apartment. I wanted to ask him how he liked me, but I didn't have the nerve.

I didn't see Orlan at all the week following my "interview" because he had been sent along with a couple of other guys to work a party on Fire Island. I was dying to talk to him, but I couldn't. I had no information about Johnny J., so all I could do is wait for Orlan to return and see if Johnny had told him anything about me. I went back to the parks and made between $20 and $40 a night and figured that was the best I was ever gonna do. It was a lot better than waiting tables or working retail. I got by.

When Orlan finally returned, he told me a lot about his job in New York, but nothing about Johnny J. He had seen him when he got back but only for a short time. Johnny had not mentioned me.

It was another week before Orlan told me that Johnny wanted to see me again. "He says he didn't really give you a very good idea of what will be expected of you so he wants another interview."

I asked Orlan questions about what that meant, but one thing I had learned was that Orlan was very loyal to Johnny J. and spoke very little of him. When he did, it was always with praise and affection.

Orlan told me that I needed to take a cab over to Johnny's home so that I would arrive at exactly midnight that night. It was only noon on Sunday and I had all day to worry and wonder about my second interview.

Johnny J. was dressed in a silk robe when a woman that answered the door led me to him in a small, dark sitting room. I knew that most of Johnny's business was females whores and I assumed that the good-looking woman that had let me in was one of them. I wasn't sure.

Johnny told me immediately that he thought that I had potential, but that I needed training. He told me to get undressed and sit in a straight-back chair close to the big lounge chair where he sat, dressed his his silk robe and silk pajama bottoms. I was uncomfortable, but I did it.

He spent what seemed like an hour talking to me, telling me that I needed to be able to read people, to understand their needs, to give them whatever it was they wanted if I wanted any repeat business. He told me that he had been gentle with me and that he wasn't really into being forceful but that I could expect a lot of clients to fuck me hard, to humiliate me, to insist that I do really dirty things for them. I listened, getting more nervous with each breath I took. He went on and on, making it sound like sex would never be pleasurable again if I came to work for him.

When he finally stood, his tone changed and he said, "Get over here and suck my dick. I'm gonna have Delores evaluate you. She is damn good at predicting whether you have a future in this business or not."

I was surprised as I looked around and saw the woman that had led me to Johnny was standing nearby, dressed in the same short maid's uniform that she had on earlier. She didn't smile even though I smiled at her and said "Hi Delores."

"Now there's your first mistake. What did I tell you to do?" Johnny asked gruffly.

I was nervous. I thought breifely before I spoke. "You told me to suck your dick."

"Well, god dammit, what are you waiting for?" he commanded, pulling his robe open. His pajama bottoms were still on him as he slipped out of his robe but I could see the outline of his cock which was already semi-erect.

"You pull my pajamas down and get on that cock," he ordered. "And by the way, if I decided to keep you around and use you, I'm always Johnny J. or Sir. Never just Johnny. That's important," he said.

I said, "Yes Johnny J. Sir," as I dropped to my knees, pulled his bottoms down and took his cock in my mouth.

Unlike the last time, he did push my face down on his cock. I gagged only once though because I had really learned a lot in recent months about sucking big cocks. He pulled my hair alot while I was on my knees. He called me a few names, but it wasn't like I hadn't heard them before. A lot of guys like to say "Bitch" and "Pussyboy" and "Queer," as well talk about how lucky I am to be sucking their cock. A couple of times, he pulled my hair hard, taking his cock from my mouth and asking me how much I liked sucking his cock. Both time, I responded with, "Its really hot Johnny J. Sir. I love your cock."

It seemed like a long time to suck before he finally pulled away and asked me if I was ready to be fucked? "Yes, Johnny J. Sir," I responded. "If its as good as the last time, you'll make me cum before I want to." It was a casual comment, but he didn't respond with anything except that he wanted me to lay across the bed and with my feet on the floor. When he realized that I was too low for him to enter me comfortably, he told me to put a pillow under my groin. "You need to accommodate me. You need to treat me like I'm your bread and butter."

I reached for a pillow and put it under my groin and I was surprised that he put some lube on his cock and then pushed some into my ass. "He entered me hard, not at all like the first time. Before, he had paused once his cock head passed my sphincter muscle, but this time, he drove straight forward, not stopping until he pushed his hard, wiry pubic hairs into my skin.

I made a little "OOMPH" sound because he knocked the air out of me, but it didn't hurt as much as he probably thought it did. He fucked me hard and moved me into nearly every position possible. I didn't have the hardon that I had had the first time. Sometimes, my cock got a little erect and then he would order me into a new position and it would go soft. When he fucked me doggy-style, he moved me to the floor instead of on the bed and slapped my ass really hard while he fucked me. I was glad when he told me to get back on the bed and lay on my side. He fucked me some more, his breath close to my neck and ears, but never once did he kiss me. When he rolled me onto my back for the third time, he pressed into me and put his face close to mine.

"Open your mouth, bitch," he ordered.

I did as he said. It was the first time that anyone had ever spit into my mouth. It was a huge glob, it seemed, but it actually turned me on a little. I closed my mouth and swallowed his spit and he told me to open up and keep it open. I did and every few seconds, he gathered enough saliva to spit another glob into my mouth. Finally, he said, "Okay swallow it and get ready to take my cum in your mouth."

He pulled his cock from my ass too quickly and it made a popping sound as it came out. He got on his knees and told me to suck him. He had done that periodically throughout the entire session and each time, I did my best, hoping he would cum, but he always went back to fucking me. This time, I was pretty sure he would cum. I sucked him deep and held his low-hanging balls in my palm.

When he announced that he was going to cum, he pulled out and told me hold my mouth open for him. I thought I must have looked like a cum-hungry slut with my mouth open as he jacked his cock with his hand. I thought it would happen quickly, but instead, he took his time. When he finally did cum, he splattered a lot of it on my face before he stuffed it in my mouth and spewed the last of it onto my tongue.

He pulled his cock out of my mouth and rolled onto his side and told me to sit on it. It was still hard and slid into me easily. "Now, jack off. Show me how much you really liked getting fucked," he ordered.

I looked around and saw his woman, Delores standing closer than before. I had nearly forgotten about her, he had kept me so tense. She looked stern and cross, expressionless.

Now Johhny J. just laid back, breathing heavy as he closed his eyes. He seemed relaxed, but his cock was still hard and it felt good now that he was letting me control the tempo. My cock got hard quickly and I knew it was important that I cum so that he would believe that I really appreciated what he had done for me. I couldn't believed the amount of cum that I sprayed onto his chest and stomach. A glob of it even landed on his chin. He just lay back in silence and almost as soon as the last dribble oozed from my cock, he said, "Okay, get dressed. I've got a customer you need to meet in thirty minutes."

I was dumbfounded. I was completely exhausted. I was sure I wouldn't get a hardon for the next twenty four hours, I was so sated. My ass was a little tender, I know I smelled of cum and sweat and was not ready for another trick. But, for whatever reason, I didn't question him. I got dressed, he handed me an address and gave me a name and I was off to my first trick for Johhny J. I wanted to know what he was going to pay me, but I didn't ask. I just left as Delores got undressed, crawled onto the bed with him and curled up in his arms as she stroked his cock and balls.

After that, I nearly quit going to school a half dozen times. He kept me busy and I was tired most of the time. I didn't know how much money he was making, but I was making at least $300 a week, most of it tips. His clients almost always always had an envelope for me to give to Johnny J., but I never knew what was in it. Most of them gave me cash and Johnny J. never asked me about it. He rarely gave me money, but I didn't care. I made three times what I had before. When he did give me money, he usually told me to go buy some hot underwear or some tight shorts. He occasionally bought new shorts and underwear for me but when he did, it was with orders to wear it for a specific customer.

Johnny J. never fucked me again after that second "interview." He definitely had a preference for women, and that was okay with me. He often told me that I had a great looking ass, but that was about the only compliments that I ever heard from him. Mostly, I didn't see him. Delores called me, told me where to go, when to be there and each day at six o'clock, I dropped off an envelope or more with one of his girls at a bar near his home. I hated going there every day and wished that I could just take the money to him weekly, but when I brought it up to Delores once, she said, "Don't start whining you little bitch." I never brought it up again.

I began working for Johnny J. as a freshman and once I graduated and went to work as an accountant for the city of Chicago, I continued to work. Johnny J. knew that I only wanted one trick a night and only could never work during the day. Most of time, he respected that, but there were times that he insisted that I work several nights in a row, wearing me down. Still, I couldn't quit. I still made more money working for Johnny J. than the city paid me for forty hours every week.