Route 66: An Erotic Adventure

Beginning The Journey

After my first ride dropped me off I walked into the town of Vincennes, Indiana, for food and to seek shelter from the rain. The ride put me off course a little, however Highway 50 west out of Vincennes soon intersected with Route 66. Hoosiers have a saying, “If you don’t like the weather, wait a few minutes and it will change.” 

I sat in the café shivering as I pondered my predicament while I waited for the Indiana rain shower to subside, so I could get back to hitchhiking to California. I looked the menu over for the most nutritious food on the menu, trying to be frugal, and conserve my meager funds. The two specials of the day were chicken club sandwich or BLT both came with chips and a small bowl of soup. I settled on the BLT sandwich along with a glass of ice water. I lingered over the bowl of tomato soup before my sandwich arrived. As I sat there watching it rain I started to question my decision to leave home and how my journey had all started years prior. Had I made a huge mistake leaving home that morning in June?

My dream trip began as dreams of traveling the Mother Road west to California years prior. I couldn’t help reflecting on that unforgettable hitchhiking trip a couple years ago when the guy in a DeSoto convertible picked me up and took me down by the river where we engaged in sex. Then took me where I needed to be and vanished never to be seen again. I wondered if I might run across him or another person for more of the same on this trip. I didn’t want to finish eating before the rain let up for fear of being shooed out of the restaurant, so I sat nibbling at my sandwich aware no more home cooked meals or warm bed to sleep in, but I’d made the decision to hitchhike across country and not about to turn back. With a little less than a hundred dollars in my pocket and 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 or seven days and how much money I’d need to reach the west coast, if I could make good connecting rides. Not 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 and hopeful I could find shelter in some public place or a truck stop. Truck stops are where I figured my best bet for rides. With no solid time schedule to reach the coast and no hurry the one thing that weighed on my mind were the many what ifs associated with a trip of this scope.

What if I ran across trouble along the way, who could I call? Who could come to my rescue? I believed I’d burned my bridges when I split. The least of my concerns 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 trouble in the form of a person or group of ruffians who might want to beat me up and then rob me, maybe even kill me. Big enough to fend off one or two tough guys, but not a large group this weighed on my mind. What if the local yokels stopped me along the way in one of the small towns and began to question me. What should I tell them? All these what ifs were starting to provoke a modicum of anxiety.  

Suddenly, I noticed a large man whi appeared to be 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 next to me. He waved the waitress over who appeared to know him. He then turned to me and said, “You look a discombobulated bub.”

“Probably do, when I left home this morning the sun was shinin. Now it’s rainin and I’m tryin to figure out the best way to get to the west coast.”

“You need aride?”

 “How far you goin?” I asked.

The waitress interrupted, she set two cups down and began to pour coffee into them. I told her that I didn’t order coffee. She replied, “If you’re gonna ride with Dan I suggest you need a cup to steady my nerves.” She laughed after saying that and took Dan’s order.

“I got aload destine for Albuquerque,”the man said. “I can get you that far…Maybe along the way I can hook you upwith another ride.”

“Thanks…What kind of load?”

“Load a 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 no 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 west.” 

“I’m leavin just as soon as I get somethin in my belly. So, if you want a ride be ready when I’m finished eatin. I got to be in St. Louis to drop my trailer tonight, so it can get unloaded and I can pick up my new load.”

“I’m ready now,” I said.

“So, how old are you?” the man asked, “Do you drive?”

“I’m eighteen, just graduated from high school, and got a drivers license too. I can drive a car or truck and can also drive a tractor.”

“Good,” the trucker said, “I figured you for maybe eighteen maybe nineteen.” He said reaching across the table to introduce himself with a firm handshake. “I’m Daniel Grabber; folks just call me Dan The Man or Dan for short.”

“I’m Roy Longfellow.”

As we shookhands I noticed his hand was large, engulfing mine as we shook hands, but there was a feeling of tenderness to his firm but not vice like grip. By the time Dan’s order arrived I’d finished my sandwich, sitting back sipping my coffee waiting for the big man to finish his meal. As I sat there studying Dan about halfway through his meal he asked, “So, where you from Roy Longfellow?”

“Ohio. What about you?”

“All over the US of A. I’m kind of like a nomad, but born and raised in Carbondale, Illinois.”

 With all said and done Dan had the waitress fill his thermos with fresh hot black coffee, and then tipped her. 

“You want acoffee to drink on the ride Roy?”

“Sure, you buying?”

Dan had the waitress make 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 the rain had stopped. Dan said,“The red and blue cab over White Freightliner over there’s 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. Intrigued I watched 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 meoff 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 gonna learn before we get to Albuquerque if you’re gonna ride with me. Watch me, I’ll show you how I shift gears on this beast Roy.”

I watched and listened as Dan explained the gear patterns, showing me what the two shiftsticks 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 highway. He double-clutched while explaining the transition of gears. For him the process of shifting seemed almost effortless, 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 turning radius and distance 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, rather noisy as we drove towards St. Louis. 

No radio to distract my attention away from Dan’s instructions as we drove. I watched 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, so a crew could unload a couple items that night and then he’d pickup the load 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, the highway I’d chosen for my cross-country journey for a few reasons. The main reason, because it’s the main east west corridor from Chicago to Los Angles. I’d learned about the Mother Road in school and decided on it being 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 by the turn of the century. The only place those highways and the towns they supported could be found, in history books. 

After Dan’s brief 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 the fuck 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, 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 didn’t plan to see this guy again. With some trepidation I opened-up to Dan. I needed to spill my guts; thus, I revealed my secret, “I’m queer.”

“I see.” 

“My boyfriend that I love moved away. I couldn’t take being separated from him, so I’d hit the road looking for him.”

A few minutes of silence followed my explanation before Dan said, “So, I’m sure at eighteen you and your boyfriend got into some type serious sexual relationship.”

“Yeah.”

“So, where did he move?”

“Out to Long Beach somewhere. His dad got a 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.

“Yeah.”

“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 where I live, but after the first time with JimmyI knew we were gonna 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. Surprise, déjà vu, there it was one of the biggest semi hard dick’s I’d ever seen. I gasp and then gulped a couple times. There, less than two feet to my left, a monster snake growing out of Dan’s open fly. I sensed I’d already been in this situation a couple years prior. I gulped again. Dan The Man held his huge dick in his right hand with the other hand on the big steering wheel guiding the truck down the highway. His hands were big, but his dick appeared a hell of lot bigger. Unlike a lot of boys I grew up with in my hometown in Ohio, I’d become infatuated from a young age with the male penis, especially erect circumcised penises. 

Not knowing the why and wherefores regarding my obsession with other boy’s penises as I grew older I became aware that some male appendages were picturesque while others were just not attractive. Dan’s dick, not only very attractive it was also one of 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. 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’d grown to know the pleasure of having another person touch my dick and enjoyed it. 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 only seen one other python the likes of what Dan had released and holding. The guy in the Desoto convertible.

“That's a real big dick Dan!”

“What do you think Roy? Like to play with?”

I gulped again. Here this guy I’d just met 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, tempted to grab the python in my hands and then see how much of the head I could stuff into my mouth I held off. After making a promise to spend the night I became 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 to watch the snake grow 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 realized my dick 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 packin. I’m sure you’re hard by now.”

Oh hell yes, my dick was chomping at the bit ready to spring out of the starting gate. I unbuttoned the front of my Levi’s. 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 so proud. 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 expressed 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 referred to, he didn’t want to cum. He wanted to save that for later that afternoon or evening when he got a room. I moved closer where I could get a better look at Dan’s dick. I began to fondle the monster that 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 it was, the prize, a pearlescent droplet of precum protruding from the urethral opening. My forefinger reached up taking the droplet I began circling the prominent purplish coronal ring at the base of Dan’s dickhead. As my wet forefinger circled the coronal ring Dan groaned and more precum appeared.  

“When we stop in St. Louis you can get to know the head a whole lot better.”

As we drove west my thoughts focused on the fact that this was going to be a two-way thing in the motel room. I also still wondered 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 willing to take that chance. I wanted to play with Dan’s monster snake. I want to try to suck his 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.

No stranger to butt fucking I’d done it a few times before with former boyfriend Jimmy, but he didn’t have 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 you’re comfortable with.”

We drove on in silence while I played with Dan’s dick. He finally 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 thenight. So many things swirled 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 lit office. From what I could see it appeared that Dan knew the desk clerk from the banter and laughter. While they conversed my last chance to make a break slipped away. 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 his semen. 

Dan had me hooked from the moment I first saw and began to play 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 could shoot a massive amount of semen. I sat frozen in the cab of the tractor awaiting Dan’s return, wondering what the future might bring.