The origins of this story are based in reality, but it's 95% fantasy
I went to college about 75 miles from my home. About once a month I would go home for the weekend, bringing my laundry with me in a battered brown case that once belonged to my father. I'm sure my mother noticed the dried pale yellow stains on my T-shirts and briefs but mercifully never said a word.
Because I didn't own a car, I had to take a couple of buses, and then hitchhike the remaining 30 miles. Back in those days, hitchhiking was more common and safer. And so, one cold, rainy November night, I found myself standing beside the highway at my last bus stop. My breath mixed with the unrelenting drizzle and after half-an-hour I wondered if I'd ever catch a ride. But after another fifteen minutes a big, late-model Chrysler pulled over. I opened the rear door and tossed in my case, then got into the front seat.
"Helluva night for hitchhiking!" said the driver. He was a tall, heavily-built man, about 45 years old and well-dressed.
"It sure is!" I said. "Thanks for stopping."
He didn't bother to introduce himself, and neither did I. He asked where I as headed and when I told him, he said that dropping me off at my home would take him just a few miles out of his way. He explained that he was a travelling salesman and made a trip through this part of the state about every two weeks. Following an awkward silence, he offered me a hip flask he'd been holding between his thighs.
"Maybe this will take the chill off," he said. "And this might help, too" he said as he turned up the heat and directed most of it to my side of the car.
"Thanks," I said, and apprehensively took a small swig from the flask. The whiskey was like liquid fire and I almost choked, but managed to swallow it.
"Don't be shy," the man said. "I've got a fifth in my suitcase that I can always refill the flask from." So I took another swig, and noticed I was indeed beginning to warm up. I handed the flask back to him and he took a swig himself.
"You need to know something about me right off the bat," he said. "I'm very direct, some might say blunt, ... and nosy, too! But you don't have to answer any of my questions if you don't want to. I get lonely on the road, and this is a rare opportunity to talk. Are you O.K. with that?"
"Yeah, I guess so," I replied. "So what do you want to know?"
"Well, for starters," he said, "what's in the case? Laundry for your mom to wash?"
"Yeah," I answered.
"And will she find some strange, crusty stains on it?" he asked.
"What the hell kind of question is that?!", I said. He reminded me that he was direct, blunt and nosy and that I shouldn't be shocked.
"Look," he said, "when I was your age, I jerked off a lot, and my mom probably washed a ton of underclothes, sheets and pillowcases just like yours. It's no big deal, O.K.? We're a couple of strangers who will never see each other again, so why not level with me?"
"O.K.," I replied. "You're right, most of what's in that case has dried semen on it."
Next he asked me how often I jerked off, where and when, an so on. My initial apprehension had somehow diminished, probably due to the whiskey, but also due to his remark that we'd never see each other again. So I answered each of his questions less and less reluctantly, even though they grew progressively more personal and probing.
"What's your cock like?" he asked. By then this kind of question didn't faze me.
"What do you mean?" I replied. "It's like everybody else's, I suppose, except probably smaller."
He said that he wanted to know if I was cut or uncut, terms I'd never heard before,
so he had to explain what the terms meant. I told him that I was cut and he said that he was too. He took another swig from his flask and offered me some. I took another swig too, by now somewhat used to the burn and actually enjoying the mild buzz I was developing.
"If I showed you my cock, would you show me yours?," he asked. "You don't really know yours is smaller than average unless you've got something to compare it against, right? Whaddya say?"
I hesitated. This was getting very strange. But while I hesitated, he took his foot of the gas so he could brace both feet on the floor. Lifting his hips off the seat, he unzipped and pulled out his semi-erect cock.
"There," he said. "Take a good look. Then when you're ready, whip yours out."
I stared at his 8-inch cock for about 10 seconds before summoning the nerve to unzip and expose mine, which looked miniscule in comparison. Then I started looking at his cock again. We drove in silence for half-a-mile while he darted glances at my cock. The driving rain didn't allow him to take his eyes off the road for too long.
"Would you mind moving over towards me some more?," he asked. "I'd really like to have a good look at that cock of yours." So I slid towards the middle of the front seat, all the while watching his cock and wondering what the guy was up to. I soon found out.
"Will you look at that rain outside?! Man oh man, it's coming down in sheets!" he said, gesturing toward the passenger-side window with his thumb. I turned my head to look and that's when I felt his right hand seize my cock in a tight, almost painful grip.
Before I could say anything, he said "O.K., kid, just relax. Don't struggle and don't try to pull away. I'm not going to hurt you. As a matter of fact, I'm going to make you feel really good. But that's only if you cooperate. We're still a long ways from your home, and I could dump you out here in the middle of nowhere if I felt like it. Think how tough it would be to catch another ride out here."
He was right. I stayed still and thought about what he'd said. Meanwhile, he loosened his grip slightly, and I could feel my cock responding to his touch, growing harder and twitching occasionally.
"See that, kid?," he said. "Your cock can think better than your brain can. So I'm ready for your answer. Will you do as I say or will you take your chances out there?"
"I'll do what you say," I replied. I had no idea what this guy had in mind, but the thought of being cold and wet all over again wasn't an alternative now.
"O.K." he said. "What I want is to find someplace out of this rain where we can have some undisturbed fun. So do you know someplace around here we could park without being bothered?"
By now we were close enough to my home that I knew my way around. I said that if we drove another two miles and turned right on a dirt road, we'd soon come to an abandoned farm. The barn was still standing, and one of the sliding doors had fallen off years ago. There wasn't any farm machinery parked inside, so we could drive right in and park undetected for as long as he liked.
"That's great!", he said, finally letting go of my cock after giving it a last playful squeeze. He told me to start getting ready by undressing and stowing my clothes in the back seat. I did as I was told, actually grateful to get out of my soaked clothes. The warm air blasting from the car's heater felt good.
Soon enough we arrived at the barn. The salesman drove in and killed the lights. He told me to get out and leave the passenger side door open. While I stood outside the car in the cold, damp air, he went back to the trunk and retrieved a bath towel from his suitcase. Then he sat on the passenger side facing out through the door, with his legs spread apart. He motioned for me to stand between his legs and rest my forearms on the car's roof.
He spread the towel over his legs and the front of his suit, about halfway up his chest. Then he reached for my now-shriveled cock and began to stroke it. I didn't resist; it was pointless, and the longer he stroked the less inclined I was to resist.
"In addition to enjoying this, I want you to pay attention to what I'm doing and how I'm doing it," he said. "Because after you cum, I'd like you to make me cum the same way."
"But I've never done that, or anything like that in my life!", I protested.
"Listen, kid, it's easy. You've already admitted you jerk off, so jerking off another guy shouldn't be all that different. But for now, relax and enjoy what I'm doing to you."
And I did. My cock grew progressively harder, and the sweet, tickling sensations stronger. As he stroked, I was aware of the dried dirt of the barn floor beneath my bare feet, the lingering aroma of manure from cows long gone, and the hooting of an owl in the forest behind the barn.
The sensations in my cock brought me out of my reverie. "I'm gonna cum," I hissed and so he began stroking harder and faster, bringing me to a climax that spurted a surprising amount of cum on the towel covering his lap, more than I'd ever produced on my own.
"Attaboy," the salesman said. "That was a spectacular load for a kid your age and size. How did it feel? Did you enjoy that?"
I had to admit I did. I laid my forehead on the cool metal of the car roof, waiting for my breathing and heartbeat to subside to a more normal rate. While I was recovering, he slid back into the car and got out on the driver's side. I heard the clink of his belt buckle as he undressed. Once he was naked, he came around to the passenger side and told me to sit down where he did. When I asked for the towel he said "No, I want to cum on you. You can wipe it off later."
He stood between my parted thighs and I saw his massive cock clearly for the first time. The excitement of jerking me off had clearly affected him, because the glans already glistened with pre-cum. I grasped his cock and began awkwardly stroking it. He told me what felt best and I adjusted my grip or stroke, following his suggestions. Soon I could feel the tension and pulsing of his cock as he approached his own climax.
"O.K., kid," he grunted. "Get ready 'cause I'm gonna cum any second now!"
And cum he did. Huge ropes of sperm that landed on my stomach and thighs, one even landing on my own cock. I was strangely proud of what I'd done and envious of how much the man could spurt. The salesman rested just as I had done and I watched his cock grow flaccid, oozing a final bead of cum that sagged and hung from a translucent thread before dropping onto the dirt floor.
After he recovered, the salesman walked back to the open trunk and got some moist wipes to clean me off. He told me to get dressed and he got dressed himself. We both got into the car and sat there for several minutes without speaking.
Finally, the salesman said "I really enjoyed that. I hope you did too."
"I did," I replied, "both times."
He nodded, started the car, and backed out onto the dirt road. We didn't talk again until we got about a mile from my home. Then he asked if I'd like to do this again sometime. I surprised myself by saying that I would. We made arrangements to meet later back in the town where I went to college. What happened next is another story.