[Contributor's note: In 1994, this author published a different story with the same title in Advocate Men. I've added "1993" to the file names for this one to differentiate it from the other story. The 1994 story was posted to the archive in 2012, and you can find it in the archives.]
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We had only gone a mile or so when he asked if I'd like to "earn" five bucks. What he wanted me to do was to haul out my dick--and I did it!
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The guy who had been sitting in a booth across from me at a burger joint got to his feet and came over to my booth. He nodded and slid in across from me. "How old are you?" he asked. His voice was nice, smooth.
"Nineteen," I answered.
He nodded again, then pulled out his wallet. Opening it, he pulled out a hundred dollar bill. "This will be yours if you come spend the night with me."
He laid the bill on the table. I stared at it. Geez, I'd never had that much money at one time in my whole life. Then I raised my eyes and slowly looked him over. He was an older guy, at least in his fifties. Dark hair beginning to streak with gray framed a thin but handsome face. Gentle brown eyes. He was wearing a suit that had obviously cost some bucks. Like he was a businessman, or maybe just a rich guy who liked to dress well. It was on a body that looked like it would be in good shape. About five-eleven, maybe a hundred and sixty pounds. I wondered what a guy like that would have in his crotch.
I raised my eyes to his. "What would I have to do?"
"Nothing you wouldn't like," he answered.
I looked at that hundred dollar bill again and nodded. "Okay." Fuck, for a hundred bucks there probably wasn't much that I wouldn't do! And the guy's age didn't bother me. Shit, for the last couple of months I'd been letting a guy older than him swing on my dick for only two bucks a throw!
But then I got curious. "How come you picked me?"
He looked me straight in the eye. "Because you're young, handsome and well-built," he answered.
And, I said to myself, because I've got a prick and a fuck-hole. I envisioned him sucking my dick or fucking me. My pecker started stretching out long and hard down my leg.
I spotted his car the minute we stepped out of the building. It was an almost new, shiny Porsche, sitting smugly between the Fords and Chevies. "My name is Paul," he said as we got in.
"Mine's Fred," I said, "but they call me Freddie."
He started out of the neighborhood. I kept expecting his hand to creep into my crotch, but it didn't. He kept both hands on the wheel. I kept expecting him to suggest that I send my hand into his crotch, but he didn't. He didn't even mention sex. Even with that, I was looking ahead and still had a boner, my hand draped over it.
He lived in a condo in a fancy neighborhood called St. James Woods. Once we were inside he didn't waste any time. "First thing," he said, "I'd like for you to take your clothes off."
We were still in the entry hall. I was wearing Levi's, a T-shirt, battered leather jacket and Keds. I took them off.
Paul studied me carefully. My entire body. My cock. He nodded again. "Nice. You are indeed a handsome, young, well-built ... and, I might add, well-hung male. Have you ever measured that dick?"
"Well, yeah, I have," I admitted.
"What did you get?"
"Eight and a half inches."
He nodded again. "Yes, I figured about that, and slightly bigger around than a four-bit piece. As I said, nice." Then he led the way into a richly furnished living room. "Make yourself comfortable," he said. "I'll fix us drinks."
He crossed to a bar and mixed the drinks, then sat in a comfortable chair across from me. His eyes went straight to my stiff whang sticking out from my bush. "As fine a specimen as you are, I imagine that you've had a lot of experiences. A lot of men after you. I'd like to hear about them."
"You're kidding!" I spit out.
"No, I'm not kidding," he answered easily and seriously. "I'd like to hear what you've done with that beautiful male body, that beautiful hunk of meat."
I was beginning to think that, nice as the guy was, he was turning into some kind of weirdo. But for a hundred bucks ... Yeah, if he wanted to hear sex stories, I could tell him some! I started digging back into my memory. "Well, the first time ..."
The first time had been simple. I'd gone into the crapper at the bus station to take a leak. Another guy had come in and moved up to the urinal next to me. A guy in his thirties, dressed sort of so-so. He had hauled out his dick and then, just as I finished pissing, reached over and took hold of my cock. Just that much stimulation and the fucker had shot out to a full hard-on. "Let's go into one of the booths," he'd said, "and I'll suck this for you." We had gone into one of the booths. He had sat on the crapper with me between his legs and sucked me off.
Paul leaned down and took off his shoes. "Did you like that?" he asked. "Did you like shooting off a load into his mouth?"
"Oh, fuck, yes! All I'd done before that was beat off. That guy's mouth was a hell of a lot better than my hand!"
His shoes off, Paul leaned back into the chair again. "Go on."
I remembered the second time for a simple reason. It had been the first time that a guy had offered--and given me--money for my dick. A young guy, not bad-looking. Fuck, I'd have let him suck me off even if he hadn't offered me money.
I didn't mention that part to Paul, but I told him the rest. I had been hitch-hiking and the guy had picked me up. We had gone only a mile or so when he asked if I'd like to "earn" five bucks. What he wanted me to do was to haul out my dick--and I did it! He played with it while we rode along. Finally we reached a side road and he turned off onto it. Way off the highway, he told me to pull my pants down. Paul's eyes seemed to have brightened. "And he sucked you off, right?"
"Yeah. He made me come three times."
Paul scrounged around a little, taking off his coat, then leaned back again. "Go on."
After that I couldn't remember a sequence. I could at least vaguely remember the guys and the kind of sex they had wanted, but not in order. But I told the stories, and two things happened. Thick pre-cum oozed out of my piss hole and Paul took another article of clothing off after each story.
Paul was finally naked, and I saw I'd been right. He was an older guy, but he had kept himself in shape. There wasn't an ounce of excess weight on his strong-looking, well-proportioned body. Except for the gray streaks in his hair, he didn't look old at all. And I got the answer to my other question. A seven-inch dick, almost as big around as mine, stuck up toward his belly. The tapered head was as slimy with pre-cum as mine. Medium-sized balls hung between his legs.
We were sitting across from each other, two naked guys with stiff, pre-cum-covered pricks sticking out of our crotches.
Paul reached down and pushed his dick off his belly, straight out. "Would you want to suck this thing?" he asked.
"If you want me to," I answered.
"Yes, I think I'd like that," he said.
I pushed myself up and crossed over, dropped to my knees between his legs and reached for his joint. I pried it out of his hand and leaned down, licking that thick, sticky cock-juice off his dick head, then sent my mouth down his shaft. I sucked slowly, using both my lips and my tongue, and reached for his balls. "Hmmm," he murmured, "yes, that feels good. One of the real joys of life, getting your cock sucked, especially by a handsome young stud." But still, a couple of minutes later, he put his hands on my head and stopped me. "That's enough for now," he said.
I pulled my mouth off his prick, let his knockers fall back between his legs, and went back to my chair. Truthfully, I felt a little disappointed. Fuck, if you suck a guy's dick you want to make him come!
"That one story ... You said that young fellow made you come three times. Can you still have multiple orgasms?"
"You mean, can I come more than once?"
"Yes, that's what I mean."
"Well, yeah, with a little rest in between. You want the truth, I sometimes shoot off seven or eight times a day."
"Well, then, for now... I'd like to watch you masturbate."
I almost gasped out, "Are you kidding?" I didn't because he obviously wasn't kidding. Instead, I scrounged down to get my butt lower on the chair and spread my legs a little more. I'd never jacked offin front of anyone, but he was paying the bill! I took my balls in one hand and wrapped my fist around my hard pecker.
I leaned my head back against the cushion, closed my eyes and tried to pretend that I was alone. I started whacking off the way I always did it, slowly at first, running my hand up and down the entire eight and a half inches, playing with the head once in a while. Paul murmured, "Hmmmmm," almost as if it was his prick getting the treatment. Before long I stated whacking on it harder and faster, and then finally I started spurting strings of hot, white cum. "Oh, fuck! Look at that thing shoot!" Paul cried out. "Jesus, look at that big prick dumping its load!" He sounded excited, almost as ifit was his prick doing the shooting.
Once I'd finished shooting off, I reached for the paper napkin he'd put under my drink. "No," he said, getting up, "I'm going to do that for you."
He went into another room, then came back with a wet washcloth. My dick had gone soft by that time, but that didn't bother him. He washed it gently, even squeezing out what juice was left in it. He washed the stuff off my hand, too, and my balls. His own prick was still hard and a new batch of pre-cum had oozed out.
Paul mixed us fresh drinks. He wanted to hear more stories, so I told him more. Over the last couple of years a lot of guys had wanted me to fuck around with them, so I had a good supply!
Most of the time Paul held his cock in his hand. Once in a while he'd give it a few strokes, but nothing serious.
Then my dick started to stir again. It hadn't gotten far when Paul jumped up, crossed over and dropped to his knees between my legs. He lifted my dick and wrapped his mouth around it and went to work on it. Sucking, licking. It didn't take long before it was up to its full eight and a half inches again, and Paul was sucking on several of those inches. He sucked on the shaft, tongued and sucked on the head, sucked on the shaft again. He sucked pretty good. I leaned back in the chair ready to enjoy a blow-job.
Paul sucked on my hard prick for a while, and played with my balls, but then he pulled away. His fingers wrapped around my bone, he looked down and said, "Yes, a very nice hunk of meat on a very nice young stud." Then he let go of it and went back to his chair.
Fuck! I was stuck with a half-primed joy-stick! But I reminded myself that it was his party. He was paying for it. I'd get to shoot off another load when he was ready for it. But still ... Man, yes, this was about the craziest sex-thing I'd gotten into.
I wondered how long it would be before Paul would want to shoot off a load of his own. Man, his poor nuts! They must be aching to fire off!
He had sucked my dick enough, worked it up enough, that my piss hole was filled with pre-cum again. He was looking right at it again. Thoughtfully, as if he were asking himself a question. Then he got up. "Come on, Freddie. We'll go into the bedroom. I want that thing up my ass."
In the bedroom he opened a dresser drawer and pulled out a tube. K-Y. He stepped in front of me, uncapped it and went to his knees. He squired out a healthy glob into the palm of his hand and went for my fuck-stick. Lubed it like he was jacking me off. Man, a little more and I would have shot off that way. But finally he quit and crawled up onto the bed on his belly. "Come on, stud, come fuck my ass!"
I looked at that ass. It was a nice one. Fairly long, firm cheeks, a succulent dimple on each side with a dark, tight gulley between them. It looked like it would be a real cock-grabber. But I figured that he expected more than just a fuck, so I crawled on and bent my head down. I started licking that tight gulley, getting a taste of sweat. I licked it from top to bottom, then reached out and pulled is cheeks apart. That little rosebud of his was like a tight mouth, puckered--like the mouth of one of the really old guys who sucked me off from time to time. I bent my head lower and started licking it. "Oooooh, yeah!" Paul groaned out. I started tongue-fucking him. Reaming him. Eating his ass, "Oh, shit," he finally said, "you're driving me nuts. Give me dick! I want your fucking dick up there!"
I pulled my tongue out and moved up. I took my swollen prick in my hand and started running the head up and down that deep, tight cleavage, then I positioned it right at his fuckhole and grabbed him round the waist with both arms. I started fucking. He grunted when my dick head broke through, but I didn't stop. My balls swayed forward, slapping against his ass. "Oh, yeah," he groaned out, "fuck me with that young stud-cock of yours!"
I fucked him, spreading his ass with my dick, scraping his prostate with my dick head, filling his ass. Pulling it out until just the head was caught by that puckered little mouth, sending it in again. I was giving him my full eight and a half inches with each cock-stroking stroke. Oh, man, yes, that fuck hole of his was nice and tight and warm, caressing my stiff dick as I slid it in and out.
My nuts tightened up in my groin. My dick was getting a really great treatment. That tight fuck hole was like a fist around it, only better. And I wasn't worried that he would stop me this time.
"Oh, yeah, Freddie, you beautiful young stud, fuck me! Fuck my ass!" he groaned out. "Jesus, that feels so good, that big fuck-stick pounding my butt!" I didn't need him to tell me. The way my cock was feeling, nothing would have stopped me. I fucked him and I fucked him. Gave him my full eight and a half inches, pulled it out, and gave it to him again. A hot, tight, moist fuck hole jacking me off like no hand could ever do. Like no mouth had ever done it. Oh, yeah, he had a cock-loving ass. "Fuck me, Freddie, fuck me! Gimme that young-stud cock of yours!"
Pre-heated the way I'd been, it didn't take as long as I would have liked. Before long I shifted into medium and then into high gear, fucking Paul with long, fast strokes. Pounding my hard pecker in and out of his tight hole until finally ... "Oh, shit, here I come!" I felt my prick fill with jizz, then fireworks started going off in my head as it started squirting out. I filled his fuck hole with my hot spunk, humping with each shot, then fell against him. Fuck, it felt like he was getting my balls right along with it.
"Oh, yes," Paul groaned out, "that was good. That stud-pole of yours is a real ass-pleaser."
From the sound of his voice, I figured that he had shot off when I did, the way some of the guys I had fucked had done.
I started to raise up. "No! Leave it in there, Freddie. Leave it in there until it goes clear soft."
I left my dick in his ass until it went soft, then raised up, slowly pulling it out. Paul rolled over onto his back. He hadn't shot off. His dick was as hard as ever, up toward his belly. His dick head was as slimy as ever, but he was still holding his load in his balls.
"Wait here," he said, and he rolled off the bed. A couple of moments later he was back with another wet washrag. He washed my dick again, and my balls and cock-hair. Then, "Come. We'll go have another drink."
It was beginning to look pretty clear. When Paul had said "spend the night with me," he had meant a night of sex--forget about sleep.
I wondered if he was one of those guys who, no matter what they did with their dick, couldn't shoot off a load. Shit, I had sucked and jacked on one guy's prick for a good hour and he hadn't come. He'd said his pecker just enjoyed the play. I hadn't minded because he'd given me twenty bucks and a blow-job. Not that I would have minded, anyway!
Halfway through our drinks Paul reached down and pushed his stiff cock off his belly again. "You feel like sucking this again?" he asked.
"Sure," I answered. I set my drink down, crossed over and went between his legs again. I took hold of his dick, pushing his hand away, and leaned over. It was re-run time. I slurped all the pre-cum off his pecker head, gave it a good tonguing, then slid my mouth down his shaft. My other hand went up for his balls, and I started pumping my mouth up and down his joy-stick. It fit comfortably; it made for good sucking. I hoped that this time he would want to go all the way. I liked the feel of his balls, and the feel of that fairly long, fairly thick dick. And it sounded again like there was hope. "Oh, yeah, this is nice. Getting sucked by a good-looking stud. Suck it, Freddie, suck it good."
I was going about it sort of slowly, to give maximum pleasure. Taking the whole seven inches, his dick head going down my throat, pulling off, taking it again. Tongue-sucking his dick head once in a while-and each time getting a little more thick pre-cum. Eating his meat with relish. Paul groaned now and then with pleasure, but then, "Do you really like sucking that cock, Freddie? Or would you like it up your ass?"
I took a couple more strokes, then raised up, pulling off his dick, and looked into his eyes. "Which do you want?" I had moved my hand up; my fingers were wrapped around his stiff prong. I stroked it a couple of times.
"Shit," he said, "even that feels good, having you jack on it. Maybe that's what I'd like, to have you jack me off."
I thought that he meant it, so I started jerking on his meat more seriously. I used the whole seven inches, the way I used all of my own dick. Stroking it from the fat base to the cock head, back down, up again, stretching it out a little on each upward stroke. He had leaned back in the chair and closed his eyes. "Hmmmm," he murmured. "Yes, that feels good. Much better than doing it myself."
Then, "Stop, Freddie. Just hold it in your hand."
I stopped. He obviously didn't want to come yet. I just sat there on my knees with his balls in one hand and his dick in the other. His dick head was shiny with slime. Then, "Your mouth again, Freddie. Use your mouth on it. Suck it."
I slid my head down to his cock-hair, leaned over and took his dick into my mouth. Licking off that sticky goo, I started sucking. "Oh, yes that's the way. Getting sucked by a nice young stud. Good!"
I sucked on it slowly but fully, working his entire cock. Using my tongue on it, too, and giving the head a treatment now and then. Playing with his balls. "Hmmrnmm!" he groaned out again.
But then, after a while, his hands came to my head and stopped me. "Let's go in the bedroom. I want to fuck your nice, young ass."
In the bedroom I crawled onto the bed on my belly. Paul got the K-Y and lubed up his own fuck-stuck, then crawled on over me. He didn't waste any time, didn't use any foreplay. He just positioned his fuck pole at my butthole, drove it into me--I let out a little yell--and started fucking.
He gave me the full seven inches, pulled it out, gave it to me again. "Oh, yes, nice young-stud fuck hole!" His balls banged against mine each time his dick went into me. It was my turn to groan. "Oh, yeah, Paul, that feels good. Fuck me, man!"
We were on our way! Fucking like that, there was no way he wasn't building up a load of jizz. His dick went in, out, in again, filling my butthole nicely each time, both of us caught in the pleasure of a good fuck. Our bodies worked like a two-part unit with a stuff rod connecting them, pumping in and out. It was even better because my own joy-stick was getting rubbed up and down between my belly and the bed.
But then ... Shit! Paul stopped again. Shoved his dick all the way into my ass and left it there, his balls hanging down over mine. Then he slowly dragged his hard cock out of my fuck hole and the truth came out. "That was lovely," he said, "but let's go have another drink. I'm not a young cum machine like you. Once a night's all I can manage, and I'm saving it for dawn."
We went back to the living room and the night went on. Paul wanted more stories and got them. He sucked me off, then more stories. He jacked me off, then more. Occasionally he had me suck on his dick or jerk on it some. Finally, dawn came. "Back to the bedroom, Freddie. This time I'm going to give you a load of spunk!"
We went back to the bedroom and he did. Man, he did! After all those false starts he flooded my fuck hole with his thick jizz. The way he howled as he shot off it was obvious that he was getting his money's worth! Then, with his dick going soft inside me, I smiled to myself. If anyone else asked me, I'd have a real sex story to tell!