Riding Bitch

by ClosetCase

16 Apr 2024 5563 readers Score 9.2 (85 votes) PDF Mobi ePub Txt


I am blindfolded, naked, hands tied together and above my head, legs spread wide and lifted up and back, tied to hold me in place. I can feel the roar of the truck and every bump in the road as we travel one of America’s interstates. I’m not sure where we are, or if I’ll ever get out of this situation. There’s only one thought that is running through my mind: “How the fuck did I get here?”

I grew up as the son of a long-distance truck driver. My dad would be gone for days at a time on cross-country trips, and so my mom was my constant. Dad loved us, and his work provided well for us, but growing up, I wished that he could be home more. I once told him that, and so when I was 12 he invited me to ride with him on one trip from Georgia to California. It was an awesome trip, getting to hang out with my dad, and getting to see parts of the country that I’d never seen before. During that trip, I met other drivers and got to see a little of the culture of over-the-road truckers. My opinion of my own father was elevated seeing him among his own. He was a cool guy, and the other truckers gave him respect. I’d only ever thought of him as my dad, but seeing them respect him, I realized that his muscular build, his tattoos, and his colorful use of language made him a man among men. He was all man, and I looked up to him immensely.

After that trip, I decided I wanted to be just like my dad. I started asking for weights and exercise equipment for birthdays and Christmas, and soon enough I was set up with a nice at home gym. I worked out and built up my muscles, and by the time I went to college I was quite a stud. I had fucked just about all of the cheerleaders at my high school, and had quite the reputation as a ladies’ man. Dad told me how proud he was of my work on my body, and how glad he was that I excelled in school. I was the total package and was loving life!

During my junior year of high school, I told Dad and Mom that I had decided I wanted to be an over-the-road trucker just like Dad. He made good money and never had to go to college, and I figured I could follow in his footsteps.

Dad got really serious when I told him that. “Son, you are going to college, and that is final!” he began emphatically. “You have good grades and we can afford to send you to school. I didn’t have that luxury. Trucking was the only option for me. I’ve worked hard to give you opportunities that I never had. You are going to college.”

I was shocked to hear Dad talk that way. He’d never complained about his work, or about how he grew up. I wasn’t even really aware that he grew up poor. But clearly, he wanted something different for me. I knew enough about my Dad to know that this was the end of the conversation. So, I began applying to colleges  and by the fall of my Senior year, I had been accepted to UGA, working on a degree in  computer science.

Fast forward to the end of my Freshman year, I was looking ahead to the summer. I had done well, keeping my grades up, joined a frat, partied an appropriate amount, fucked a bunch of girls, worked out regularly, and generally enjoyed college life to the fullest! I was a beefy jock stud, smooth skinned, with a handsome smile and a nice body. I was truly young, dumb, and full of cum. For the summer, Mom wanted me to come home and work, saving up some money by living at home. Dad wasn’t there much, and I think she was lonely and wanted the company. But as a young man with my first year of “freedom” under my belt, I wasn’t ready to live at home again. Instead, I wanted to enjoy life and experience all it had to offer. I told my parents that I had gotten a job in Athens and would stay with a buddy who had an apartment for the summer, which wasn’t entirely untrue. I did have a buddy, Ben, who had an apartment. He did offer to let me stay with him, whenever I was in town over the summer. He even let me store my stuff from my dorm room in his apartment for the summer, so technically, his apartment was my address for those 3 months. And I was planning on working whatever odd jobs I could find.

What I did not tell either of my parents was that I was not planning on being in town very much over the summer. I still had the bug to travel over-the-road, ever since my summer trip with Dad. I wanted to experience it now as an adult, to see if it had the appeal that it held for me as a kid. So, with all of the wisdom of a stupid 19 year-old, I got Ben to give me a ride down to I-20 in Madison. Loaded with my backpack and outstretched thumb, I set out to hitch-hike across America without a care in the world.

I began my trek on the west-bound entrance ramp off Hwy 441. About 30 minutes after I walked onto the ramp, a red Peterbuilt tractor-trailer turned onto the ramp. I was situated about halfway down the ramp, and the driver must have seen me because he pulled off on the shoulder before he even got to me. His window was down, and he motioned me up to his truck. I jogged up to his window, as he yelled down, “Where you headed, kid?”

“Nowhere particular,” I answered back. “Just looking to travel around and see the country this summer.”

“Well, my partner and I are headed to California and back. You wanna join us?” I hadn’t seen until he mentioned it that there was another man in the cab. Up close, the driver was a beefy dude with a full beard. He was wearing a t-shirt, but I could see tufts of dark chest hair poking out of the top of the shirt. His look and demeanor reminded me a lot of my dad. This was a man’s man. I couldn’t see the other guy, but decided to join them anyway.

“Sure!” I responded.

“Go around and hop in on the other side, son,” he said. I walked around the front of the newer truck, arriving at the passenger door as it opened. The other man stepped down to let me in, and I got my first glimpse of him. He was a little bit younger than the driver, but just as beefy. He had a full beard, but his head was bald, and I noticed sleeve tattoos cascading down both of his arms. I was pumped! I had really lucked out with two manly dudes and the open road before us. I knew we were going to have a great time, and this was shaping up to be exactly what I wanted: a repeat of the great guy time I had with my Dad!

The younger dude held out his hand: “I’m Vince. That asshole driving is Todd.” Taking his hand, I replied, “Carter.”

“Welcome to the trip, Carter!” Vince motioned for me to step up into the cab. I climbed up and into the cab. I felt Vince’s hand on my ass as I climbed, but I assumed he just didn’t want me to fall, which was thoughtful of him. Once up in the cab, I stepped over Vince’s seat. Todd directed me to put my pack on the bed in the back, then he showed me how to raise up the jump seat that his truck had between the driver and passenger seats. “I hope you don’t mind ridin’ bitch!” Todd said, laughing.

“It’s all good,” I replied. Once Vince and I were both settled in our seats, Todd put the truck in gear and we began rumbling down the entrance ramp and onto I-20 westbound, headed toward Atlanta and beyond.

The three of us fell into easy conversation as we began our journey. They told me that they drove as a team, which meant that they could get their loads delivered twice as fast as a single driver. They would sleep and drive in shifts, and had a good system worked out. Once we crossed the Alabama state line, they told me, Vince was going to the back to sleep while Todd drove. Later that evening, they would switch places. The thing that I noticed about these two guys was how they seemed to be good friends, and really comfortable around each other. They were both very handsy, and they would regularly joke around and bust each others’ balls. Their comradery was infectious, and soon I was joining in their teasing as well, both giving and taking.

Of course, they wanted to know my story as well. I told them about Dad being a trucker, and wanting to relive the fun of our drive together. They wanted to know why I didn’t just go out on the road with my Dad. “Two reasons,” I explained. “First, Dad doesn’t want me to end up becoming a trucker. He wants me to finish college and be successful in a ‘normal job.’” I used air quotes to let them know I was quoting him, not trying to insult them. “Second, I was a boy then, and I’m an adult now. I want to experience the excitement of traveling without feeling like he is looking over my shoulder all the time.”

“So, how did you convince them to let you set off on this adventure?” Todd wanted to know.

I sheepishly answered, “I didn’t tell them! They think I’m working the summer in Athens and living with a buddy in his apartment.” They seemed very interested in hearing that no one except Ben knew what I was doing, and that I was free for the summer. I didn’t really think much about it, assuming they were just getting to know me, as I was them.

We took the mandatory trip on I-285 around downtown Atlanta, getting back on I-20 westbound about 45 minutes later. I watched the exit numbers count down as we got closer to the Alabama line. Finally, we crossed into Alabama and I was out of Georgia and truly on my adventure. Vince got me to stand up and switch seats with him so that he could go to the back and sleep. He slapped my ass as I moved in front of him, laughing as he said, “You better be careful stickin’ that round thing in my face! I might get sprung!” The Sir Mix-a-lot reference aside, I knew that I had a nice ass, and my buddies were always teasing me about it. Vince and Todd already felt like buddies, so I didn’t think anything more of it than friendly banter and crude guy humor.

I settled into the passenger seat as Vince got settled in the bed. There was a curtain that separated the sleeping compartment from the front of the cab, and he pulled that closed to darken the back so he could sleep. Once Todd and I were alone, he wanted to know about me, about growing up, about my Dad and his driving experience. Eventually we came around to the topic of sex. “You got a girlfriend, Carter?”

“Just one?” I asked back, laughing. “No, I don’t have a steady girlfriend. I’ve been too busy fucking as many girls as possible this year!”

“Nice!” he responded back, smiling over at me.

Feeling a comradery with these guys, I continued the conversation by saying, “I bet you get a lot of pussy yourself out on the road!”

“You’re right,” he responded, “but maybe not the pussy you’re thinking about.” I looked over at him quizzically as he continued, “Vince and I are both gay, so we pick up guys while out on the road. You would believe the number of dudes we’ve fucked in this truck!”

I didn’t know what to say. In my limited experience, I didn’t have a category for masculine guys who were into other dudes. I guess my face registred my shock at his admission, because he laughed as he asked, “You going to be okay over there?”

“Yeah,” I stammered, unsure of what to say to his revelation.

“I guess you don’t think we look like gay guys?” he asked, carrying the conversation forward.

“I don’t know,” I replied, “I just didn’t expect… I mean, I thought you both were, like, manly dudes who fucked women, is all…” I couldn’t find any of the right words and I felt and sounded like a complete idiot. I didn’t care about them being gay, I just didn’t expect it. I blushed as I realized just how stupid I sounded.

“Well,” Todd said, drawing out the word for emphasis, “We are in fact manly men. We just happen to fuck other men!” He laughed again.

“So, are you guys, like a couple?” I asked, unsure of how their relationship might work, but a little curious about what I had gotten myself into.

“No,” answered Todd. “We’re just friends who are both tops. We do pick up bottoms and fuck them together on occasion, though.”

“Tops?” I asked. My naivety was on clear display.

“You don’t know what a Top is?” Todd asked. I shook my head no. “Well, top and bottom,” he began, “are the terms that refer to gay men and their roles in the bedroom. A top fucks the ass of the bottom. The top gives cock, the bottom receives it.”

“Oh,” I said, finally understanding. “Where do you find the bottoms you fuck?” I’m not sure why I was expressing interest in their gay sex, but it was a topic with which I had no experience. My curiosity was piqued in the conversation, even if it was about sex between men.

“Well,” Todd laughed, “usually we pick them up hitch-hiking along the road, and we take turns fucking them while the other drives!”

“Oh shit!” I thought. I might not be the smartest guy in the world, but it didn’t take much to realize that they had picked me up thinking I was looking for sex with them! Worse, the jokes that Vince had made about my ass were not just male bonding: he really wanted my ass!

Todd interrupted my internal freak-out by asking, “Have you ever fooled around with your buddies? Jerked off together, sucked each other, anything like that?”

“No!” I answered, probably too emphatically.

Todd chuckled as he said, “Hey buddy, calm down! I’m not trying to threaten your manhood. I was just making conversation.”

“I’m sorry,” I replied. “I was just caught off guard by the question and the entire conversation. I mean, I would have never assumed that the two of you guys were into other dudes!”

“Well, don’t knock it till you try it!” Todd laughingly said.

He dropped the conversation there, and we had a good time talking about what we saw as we continued driving across Alabama and into Mississippi. After several hours on the road, Todd pulled into a rest area for us to relive ourselves. Vince woke up and we all stretched our legs and pissed, stopping by the vending machines to grab drinks before climbing back in the rig to continue our journey for the day. Vince wasn’t sleepy anymore, and Todd was still driving, so I rode in the middle again, but very quickly felt myself getting sleepy. I asked if I could lay down for a nap for the next leg of the trip. The two guys smiled at each other as the nodded, and I climbed into the back and lay down on the bed. The humming of the truck engine and the rhythm of the road had me asleep pretty quickly.

I awoke very disoriented. I could tell that I was in a moving vehicle, but couldn’t remember why. I couldn’t see, and realized that my eyes were covered by something tied around my head. I tried to reach up and remove it, discovering however that I couldn’t move my arms as they were tied together above my head. I was laying on my back, and an uncomfortable soreness and fullness was radiating out of my asshole. My legs were also secured, pulled back over my chest and apparently tied to the same wall that my hands were.

“Good morning, princess!” I heard Vince’s voice say. Hearing Vince and recognizing his voice caused me to realize where I was.

“What the fuck?” I asked. “What have you done to me? Let me go!”

“Calm down!” I heard Todd bark from the driver’s seat. "We're giving you a real taste of life on the road with two horny truckers!"

“Yeah,” said Vince. “Todd and I talked about it, and we decided that it was time we expand your horizons and give you a little taste of our world. Plus, we can call this the price of the ticket for your free ride across the country!”

“What have you done?” I asked, tears beginning to form in my eyes at the helplessness that I felt.

“We spiked your drink when you weren’t looking,” Vince said, “and once you fell asleep, we tied you up, blindfolded you, and we’ve worked the smallest of a series of five butt plugs up your hole. We’ve got to get you opened for your first fuck, princess!” He laughed cruelly at my predicament. “In fact,” he added, “it’s time to increase the size.”

“LEAVE ME THE FUCK ALONE!” I shouted. “SHUT UP!” Vince replied sternly. His unexpected slap across the face stunned me into silence. I felt hands moving around my groin, hearing the sound of Velcro unfastening, then feeling the plug being unceremoniously pulled from my hole. I heard the sound of a cap being popped on a bottle of some sort, and cool liquid hit my hole before I felt the end of something bigger than the first plug begin pushing at my hole.

“FUCK!” I yelled as my hole gave way and the bigger plug breached my ass. "Take it out! That fucking HURTS!" Vince ignored my request, instead fastening whatever harness he had around my waist that held the plug firmly in my ass.

When he was finished, I sensed the presence of his face near my neck, feeling his breath on my ear. He bit my earlobe, moaning in my ear, as he then whispered, “Fight it all you want, but our cocks are going in your hole soon, and I know your tight ass is going to feel like velvet around my dick. Your jock butt was made for plowing, and on this trip, we’re going to show you just how much little jock bitches like you love to get fucked! You wanted a trip to remember: you'll never forget this experience, bitch!”

I shivered in terror at the thought! This trip was not at all what I had expected, and from Vince’s words, the worst was still ahead of me. How did I get in this position? I had no idea what truly lay ahead, or how this trip would change my life forever!


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by ClosetCase

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