After my first ride dropped me off I walked into the town of Vincennes for some food and to seek shelter from the rain. Hoosiers have a saying, "If you don't like the weather, wait a few minutes and it will change." I sat in the café pondering my predicament waiting for the Indiana rain shower to subside. I was looking for the cheapest, yet most nutritious thing on the menu, trying to be frugal, conserving my meager funds. The two specials of the day were chicken club sandwich or BLT both came with a small bowl of soup. I settled for the chicken club sandwich for lunch along with a glass of ice water.
I was lingering over the bowl of split pee and ham before I began my sandwich. As I sat there watching it rain I was starting to question my decision to leave home. Had I made a mistake leaving home that morning in June? I didn't want to finish eating before the rain let up for fear of being shooed out of the restaurant, so I was nibbling at my sandwich. I was aware there would be no more home cooked meals or warm bed to sleep in, but I'd made the decision to hitchhike across country and was not about to turn back. I had a little less than a hundred dollars in my jeans and was hopeful I could make it last for the duration of my cross-country adventure.
Before I departed on my journey I'd calculated the trip to take five maybe six days and how much money it would take to reach the west coast. That was if I could make good connecting rides. Not being wasteful with my money I'd determined about $60.00 dollars would buy two meals a day for six days. My bedroll was where I'd sleep. I was hopeful I could find shelter in some public place or a truck stop. Truck stops are where I figured my best bet for rides. I was on no time schedule to reach the coast, so I was in no hurry. The one thing that was weighing on my mind were the many what ifs.
What if I ran across trouble along the way, who could I call? Who would come to my rescue? The least of my concerns was running out of money. I figured if I ran out of cash I could stop and work along the way doing odd jobs to make a few extra dollars. My main concern was trouble in the form of a person or group of people who wanted to beat me up and then rob me, maybe even kill me. I was big enough to fend off one or two tough guys, but not a large group. What if the local police stopped me in one of the small towns along the way and began questioning me. What would I tell them? All of these what ifs were starting to provoke a modicum of anxiety.
Suddenly, I noticed a large man in his mid twenties enter the little eatery located next to the truck stop. He looked around the crowded café for a vacant seat then sat down across from me. He waved the waitress over who it would appear he knew and then said to me, "You look a discombobulated bub."
"Probably, when I left home hitchhiking this morning the sun was shining. Now it's raining and I'm trying to figure out the best way to get to the west coast."
"You want a ride?"
"How far are you going?"
The waitress interrupted setting two cups down and began pouring coffee in them. I told her that I didn't order coffee. She replied that if I was going to ride with Dan I would need a cup to steady my nerves. She laughed after saying that and took Dan's order.
"I got a load destine for Albuquerque," the man said. "I can get you that far."
"What kind of load?"
"A load of shit," the man laughed, "What difference does it make? I'm offering you a free ride."
"I guess I can go that far with you," I replied.
"Well hell, don't do me any favor," the man said.
"I apologize. I don't mean to be sarcastic."
"No need to apologize kid. I think I understand your apprehension. You're a newbie to the road."
"Yeah, my first trip."
"I'm leaving just as soon as I get something in my stomach. So, if you want a ride be ready when I'm finished eating. I got to be in St. Louis to drop my trailer before five."
"I'm ready now," I said.
"So, how old are you?" the man asked, "Do you drive?"
"Be eighteen in a few weeks, and got my drivers license too. I can drive a car or truck and can also drive a tractor."
"Good," the man said, "I figured you for maybe eighteen maybe nineteen." He said reaching across the table to introduce himself. "I'm Daniel Grabber; most folks just call me Dan The Man or Dan for short."
"I'm Roy Longfellow."
As we shook hands I noticed his hand was large, engulfing mine as we shook hands, but there was a feel of tenderness to his firm but not vice like grip. By the time Dan's order arrived I'd finished my sandwich and was sitting back sipping my coffee waiting for the big man to finish his meal. As I sat there I was studying Dan. About halfway through is meal he asked, "So, where you from Roy Longfellow?"
"Seymour. What about you?"
"All over the US of A. I'm kind of like a nomad, but I was born and raised in Carbondale, Illinois."
Once all was said and done Dan had the waitress fill his thermos with fresh hot black coffee, and then tipped her.
"You want a coffee to drink on the ride Roy?"
"Sure, you buying?"
Daniel ordered me a large coffee with cream and sugar to go and as soon as the waitress returned with it we were off to his truck in the parking area. The first thing I noticed as we stepped outside was the rain had stopped. Dan said, "The red and blue cab over White Freightliner over there is mine."
We both climbed up into the crowded cab by way of opposite doors. Once inside Dan pulled out of the parking area onto US 50 where he began driving west. I was intrigued watching him shift gears. He shifted the twin sticks with the adroitness of a maestro conducting an orchestra. As we sat together in the cab rumbling down the highway the conversation began, "So what kind of tractors have you driven?" Dan asked first off.
"Ford, John Deer, Farmall..."
Dan cut me off saying, "I thought you meant you'd driven tractors like this one, not farm tractors."
"Nope, never driven anything this big before."
"I guess you're going to learn before we get to Albuquerque. Watch me, I'll show you how I shift gears on this beast Roy."
I watched and listened as Dan explained showing me what the two shift sticks were for and what they did. I never heard a clash or grinding of the gears as the big man's hands glided through the proper gearing as we continued picking up speed driving down the road. He was double-clutching while explaining the transition of gears. For him the process of shifting seemed almost inborn. He told me about his tractor as far as type engine, horsepower, type transmission and driving axle, all of which I knew nothing about. Then he went on explaining about the outside mirrors and how to judge the turning radius as well as the difference in driving a car and sitting up high in a cab over tractor. The ride west in the Freight Shaker, as Dan called it, was rather noisy as we drove towards St. Louis.
There was no radio to distract my attention away from Dan's instructions as we drove. I was watching his every move, so if he asked me to drive I might be able to duplicate his moves. He explained that as soon as we got to St. Louis he was going to drop off the trailer overnight, so a crew could unload a couple items and then pickup US 66 for the trip onto Albuquerque. He was going to stop for dinner and a night of rest before hitting the road west again. I had a feeling he might put me in the driver's seat once we got on Route 66 the next day.
The Mother Road was the highway I'd chosen for my cross country journey for a few reasons. The main reason was because it was the main east west corridor from Chicago to Las Angles. I'd learned about the Main Street of America in school and decided that it was the best route for my journey west. The teacher told us that within the next decade the new Interstates would overtake the smaller highways that crisscrossed America. The small towns dotting the older highways would dry up and be gone. The only place those highways and the towns they supported would be found was in history books.
After Dan's training lecture he began asking more personal questions, "So, did you leave a broken-hearted little filly behind or was she knocked up and you had to get out of town fast?"
"Nope, neither. I don't have a girlfriend and never had sex with a girl."
"Really, good-looking jock without a girlfriend? Unbelievable."
For me this was now one of those awkward moments I had to face in my life. I had been taught to never lie and I wasn't going to lie now; besides, I was never going to see this guy again. With some trepidation I opened up to Dan. I needed to spill my guts to someone; thus, I revealed my secret - I was queer. My boyfriend that I was in love with had moved away. I couldn't take being separated from him, so I'd hit the road looking for him.
There were a few minutes of silence after my explanation before Dan said, "So, I'm sure at almost eighteen you and your boyfriend got into some type serious sexual relationship."
"So, where did he move?"
"Out to Long Beach somewhere. His dad got a new job in the aircraft industry out there and being he was seventeen his mom said he had to move with the family."
"I know Long Beach, been there many times. So, that's why the hitchhiking adventure across country?" Dan queried.
"You got your boyfriend's address and phone number?"
"Yeah, in my wallet."
"So, you ever had sex with anyone besides your boyfriend?"
"Yeah, a couple other kids in the area, but the first time with Jimmy last year I knew we were going to be together for life."
"Yeah, I've heard that many times before. So, you ever had sex with an older guy?"
I turned my head towards Dan to answer and saw the biggest semi hard dick I'd ever seen. I gasp and then gulped a couple times. There, a couple feet to my left, was this monster snake growing out of Dan's open fly. I gulped again. Dan The Man was holding his huge dick in his right hand while the other hand was on the big steering wheel guiding the truck down the highway. His hands were big, but his dick was a hell of lot bigger. Unlike a lot of boys I grew up with in Seymour, I was infatuated from a young age with the male penis, especially the erect circumcised penis.
I don't know the why and wherefores with regard to my obsession with other boy's penises; however, as I grew older I was aware that some male appendages were picturesque while others were just not attractive. Dan's dick was not only very attractive it was also the biggest I'd ever seen.
"What do you think?"
I sat there at a loss for words. I didn't know what to do or say. I was spell-bound. I wanted to reach across and cop a feel of the beauty, but I didn't dare chance distracting Dan for fear of wrecking us if I touched it. I knew the pleasure of having another person touch my dick. I tended to jerk, squirm and moan under touch. Enjoying dicks from a young age I'd seen a few adult dicks at the YMCA in the town where I lived. At the Y most of us swam nude, but in all those times I'd never seen a python likes of what Dan had released and was holding.
"That's a real big dick Dan!"
"What do you think Roy? You like to play with?"
I gulped again. Here this guy I'd just met was holding this huge dick in his hand asking me if I wanted to play with it. Hell yes I wanted to play with it. I'd also like to try sucking it, so I asked, "Do you want to pull over so I can play with it?"
Dan replied, "I'm going to stop somewhere around St. Louis for the night. So, are you interested in spending the night with me for some sex play? Or do you think you'll be looking for another ride west tonight?"
"Yeah," I replied excitedly. "Damn right I want to spend the night."
Dan didn't have to ask me twice. I needed a place to stay for the night, so I might as well stay with Dan and get the enjoyment of playing with his dick. I began to wonder if he wanted me to do things that would bring him pleasure or was there a chance of reciprocation. Again, I was tempted to grab the python in my hands and then see how much of the head I could stuff into my mouth. After making a promise to spend the night I was overcome with all these crazy thoughts running around in my head.
What if this guy was a sex maniac who had picked me up just to have sex with me and then kill me? I'd heard stories about that before, but I dismissed the thoughts as I once again looked over towards Dan. He didn't look like a killer. I continued watching more of the snake growing out of his fly with each mile we drove. He continued stroking the head like someone petting a cat's head.
"So, what about your boyfriend? What would he say if he knew you were going to play around on him?"
I hadn't given any thought to Jim. I was realizing that my dick was throbbing to escape the confines of my jeans. I needed some relief, so I figured what Jimmy didn't know wouldn't hurt, and now I had the chance to play with Dan's huge dick. That was going to overshadow my feelings for Jim.
"How big is yours Roy?"
"Last time I measured, when Jimmy measured, it was almost six and half inches long, but not anywhere near as long or fat as yours."
"Well this baby measures almost eight and half inches long, but I've never measured how thick it is."
"Sure has a beautiful pink head on it."
"What all have you done with your boyfriends?"
"We jack each other off and suck each other."
"So, Roy why don't you go ahead and show me what you're packing. I'm sure you're hard by now."
Oh hell yes I was hard. My dick was chomping at the bit ready to spring out of the starting gate. I undid the front of my pants. My dick sprang free, slapping back against my stomach for Dan to see as I hooked the waistband of my underwear beneath my scrotum. There it was, I don't think I'd ever seen it so big and throbbing hard before.
"Very nice and circumcised, just the way I like them. I'd sure like to give that beauty of yours some personalized oral attention tonight," Dan said. "Go ahead, I know you want to touch mine."
I gulped again before replying, "Yeah." Dan had express interest in giving me a blowjob and my dick knew it.
"Well go ahead and move closer, examine it, hold it, play with it, whatever you want to do with it, but don't make it sick and puke all over the place," Dan said with laughter.
I knew what Dan was referring to, he didn't want to cum. He wanted to save that for later that afternoon when we got a room. I moved closer where I could get a better look at Dan's dick. As I began to fondle the monster it had grown to almost full size. I could see the texture lines in the head. He had a large piss slit, twice as big as mine. There was a pearlescent droplet protruding from the urethral opening. My forefinger reached up taking the droplet and then began circling the prominent purplish coronal ring at the base of Dan's dickhead. As my wet forefinger circled the coronal ring Dan groaned.
"When we stop in St. Louis you can get to know the head a whole lot better if you'd like."
As we drove west my thoughts were focusing on the fact that this was going to be a two way thing in the motel room. I was also still wondering what this man might do to me after he finished having sex with me. I didn't think I could fend him off do to his size if he made an aggressive move on me, but I was willing to take that chance. I wanted to play with Dan's monster snake. I want to try to suck Dan's dick and I wanted him to suck mine, but what if he wanted to cornhole me with that thing? Surely, if Dan tried to fuck my ass with that monster he would split me open like a splitting maul put to a chunk of hickory.
I was no stranger to butt fucking. I'd done it a few times before with former boyfriends and Jimmy, but none of them had a dick as big as Dan's. So, I asked, "What kind of stuff do you want to do together after we stop for the night?"
"Whatever you're comfortable with Roy."
"I mean are you going to try to cornhole me with that monster?"
"Like I said Roy we'll only do what is comfortable for you."
We drove on in silence me playing with Dan's dick. He was finally forced to put it away as we closed on St. Louis. After Dan dropped the trailer for the night for the crew to unload he began looking for a motel. I sat passively waiting for the big man to find lodging for the night. So many things were swirling around inside my head. Thoughts of me becoming Dan's sex slave for months to come and then one day he would tire of me, kill me and throw my lifeless body out in the desert somewhere in Arizona or New Mexico. But Dan didn't give off killer vibrations.
Suddenly, Dan said, "Here we are." He pulled the cab over tractor into the parking area and said, "You stay in the cab while I go get the room."
Dan got out of the truck and walked towards the neon lighted office. From what I could see it appeared that Dan knew the desk clerk from the laughter and conversation they were having. While they conversed was my last chance to make a break. I could escape into the night and never see the man I'd been riding with for the last few hundred miles from Indiana through Illinois to St. Louis again. Although I knew I should slip away I wanted to spend the night with Dan to at least jack his monster dick off and watch him shoot his huge load. I was sure he could fill a coffee cup with is semen.
Dan had me hooked from the moment I first saw and began playing with his king size dick in the cab of the tractor before we stopped. I'd become mesmerized by the beauty and size of his appendage. I just knew he was going to shoot a massive amount of semen. I sat frozen in the cab of the tractor awaiting Dan's return, wondering what the next move would entail.