A Long Ride Home

PART TWO

I climbed up and tapped on the driver side window. Dennis checked his clock as he came out. "Damn, that's making good time. There's a green Peterbilt two trucks that way pulling a van. That'll be Doug. He's a country boy and probably just wants to unload in something warm." I was about to climb down when Dennis raised his voice, "Where's that fifty?" I slipped off my shoe and retrieved the bill for him. "Good boy. Remember, get the money first."

"Alright, alright. See you in a bit."

I walked over to the green truck as my well-used insides gurgled and sloshed with the cum of two men. Well, the last two men at least. Doug had the passenger door open for me before I could knock, and I climbed into his cab. The cab was lit with the same amber light dotting the trailers in the lot and accentuated his ginger qualities. He stood well over six foot with a Fu Manchu moustache, a light dusting of ginger fur, and the baggiest boxer briefs I'd ever seen on a man. He must have bought at least two sizes too large. His muscles and tattoos told a tale of having been in the Marines and his smile was genuine. "So, your Dennis's," he paused thinking what to call me, "coworker?"

I smiled at his awkwardness, "I guess you could say that. You got the fifty?"

He handed me over two twenties and a ten and I stuffed them into a little zipper pocket in my shorts probably meant for condoms.

"So, what are you into?"

He smiled shyly and sat on his bed. "Um, I've only ever done it with one other dude. Pretty basic stuff, really get off on fucking. Not really into blowjobs as a rule."

I looked down at his briefs for any signs of life and found a half hard cock starting to come around. I slipped off my shoes, turned around, and slid my shorts down, bending myself in half in the process and opening my ass.

"Fuck, that's sweet. You got a better ass than most women." He ran his index and middle finger down my crack and slipped them into my hole. Then he placed his thumb on my perineum and massaged my prostate releasing a small moan from my depths. I looked between my legs to see a nice cock tenting his loose briefs and a set of ginger balls falling out the leg hole.

He slipped his underwear off, grabbed my hips, and guided me into a seated position on his dick. While my hole was swollen from the last two dicks, the loads inside helped him to penetrate me with ease.

"Ah fuck yeah," Doug said as I started riding him.

His dick was a decent girth and slightly larger than average and I was able to twist my nipples and make my hole work his cock. Every time I raised up, I'd twist and pull and feel my hole grab and milk his cock. Doug's hands stayed on my hips as he repeated 'fuck yeah' over and over.

I thought I was getting close to making him come when he decided to change up the position. He stood up with his cock still inside me, holding me under my thighs, and drew my attention to a grab bar across the entrance to the sleeper. "Grab that bar and then turn towards me."

As I performed this mild acrobatic, he placed my calves on his shoulders. Once we were secured in our position, he started pounding away in me. The cum from previous men squished around between us and created smacking sounds when our bodies met. He looked down at my caged cock. I knew the instant he saw it from the sudden swelling in my ass. Doug wiped a gob of precum of the metal and licked it off his thumb. "Can you cum with that on?"

"I haven't so far, but it's a new addition. Dennis wanted to make sure I only had my mind on the customer's cock instead of my own."

The thought appealed to Doug and his cock swelled just a smidge more inside me. "Can you do me a favor?"

"Within reason," I replied.

Doug pulled me off the bar, spun around and threw me onto the bunk. His arm reached to the very back of a deep cubby and he pulled out something red. "Will you wear this?"

I separated the items to find a red satin nighty and two red thigh high sheer hose with little pink bows at the top. My dick ached for the first time as I felt the cheap fabric in my hand. "Sure." I put on the nighty and the hose, making a big production out of pulling them on and snapping the elastic at the top. On my little legs they almost reached my crotch.

Doug rubbed my legs and looked at me with an almost romantic eye. "Fuck yeah! That is fucking hot!" He bent my ankles back towards my ears and slammed his rigidness inside my ass. The pounding he gave was other-worldly, like the sissy outfit had released a demon from within him. He pounded my hole while his facial hair nuzzled in the nape of my neck. And then, suddenly he froze, and I felt that familiar warmth filling me. He gave a couple finishing thrusts and then collapsed on top of me for a moment. His heart was beating so fast and hard in his chest, I could feel the cab move with it. Eventually he pulled himself off me and laid next to me.

I laid there for a moment, wondering how long I needed to stay. Surely, I had given him fifty dollars’ worth of my time and body. I slowly got up and undressed...and then redressed in my own clothes. I kneeled on the bed between his legs, steadied myself by putting a hand in the middle of his chest, then kissed his clavicle. "Are you good?"

He replied with his most use phrase of the evening, "fuck yeah."

I climbed down from the truck and headed back to Dennis, tapped on the window, and he crawled out from the sleeper, yawning and scratching his furry chest. "Jose is in that white day cab over there with the belly dump. He'll probably be pretty quick, but you'll have to wake him up."

I slipped the fifty from Doug to him. "Okie dokie smokey."

Approaching Jose's truck, I wondered two things: one, where was he sleeping in a day cab with no sleeper, and two, where was he going to get off with me? My first knock on the door went unanswered, as did my second, but when I tried the door handle, and he heard the door unlatch he was up in a flash. "What the fuck?"

"Dennis sent me."

His sleepy scowl stretched into a smile. "Oh yeah. Hold on, I'll be right down." The truck shook and trembled as Jose reassembled himself and came down. In his hand was a thick padded jacket he threw to me as his booted feet touched the ground. He was short, only slightly taller than me, with a thick moustache, a five o'clock shadow, and a nice thick muscular body covered in a layer of fat that gave him a cuteness anyone would want to cuddle. He was like a warm teddy bear with a Mexican accent. "Put this on."

The jacket was oversized with a canvas outer shell and a satin diamond stitched interior. "It's not that cold."

"Not for warmth, for comfort. Put it on. I ain't had the truck washed in a while." While none of his words made any sense to me, I did as he told me to. He handed me a fifty-dollar bill, which I placed in the little pocket in my shorts while he led me to a spot behind the cab. He pushed me until the small of my back was firmly against the frame of the truck. In one smooth motion, he grabbed the waist of my shorts, lowered them, and then lifted my legs onto his shoulders, using the truck frame as a cantilever. He reached down undid his jeans and then I felt his thick stubby cock press into my hole. He pounded feverishly with a look of pure joy on his face, like a stud breeding a bitch. With my back rubbing back and forth on the steel frame, all his words from before now made sense. It couldn't have been more than ten minutes before he sped up and then slowed and his thick moustache framed the perfect circle his mouth was making. When he'd unloaded his nut in me, he pulled out, retrieved my shorts from his back pocket, slipped them over my feet and slid them onto me, my feet rejoining the ground.

He zipped up his pants, squeezed my ass while he kissed me, slipped his jacket off me, smiled, and said "gracias" before unceremoniously climbing back into his cab to go back to sleep.

I stood in amazement for a second as I recalled the last fifteen minutes of my life. I shrugged my shoulders and headed back to learn my next assignment.

Dennis rolled down the window laughing, "Told you he'd be quick. I always call him Speedy Gonzales. You got my money?"

I handed over his fifty dollars.

"Cool, over half done. Pat his in that dark Kenworth with all the shiny chrome and all those fucking marker lights. He's an older guy, super nice. Don't know if he's ever had a guy before. You might have to wait twenty minutes while his little blue pill takes effect."

"I'll practice my conversation skills."

I climbed down and headed over to Pat's truck. Dennis wasn't kidding about the marker lights and the chrome. Any part of the truck not reflecting the truck stop lights was giving off an amber hue. Inside the cab a red light glowed from behind the curtains. I tapped on the door and got quite the surprise.

Pat wasn't 'older,' he was old. Seventy if he was a day. The man stood over six foot with skinny limbs, a gut, a dark black dick starting to respond to his pills, and massive pendulous balls dangling quite a way down his long legs. He grabbed me, hugged me, and kissed me. "Let's get them clothes off you." He placed his fingers on my waistband, and I placed a hand on his chest covered in swirls of grey hair to convey he needed to pause.

"You got the entrance fee young man?"

He laughed in his deep rich tone. "Yeah baby, here you go. Don't want to get you in trouble with your handler."

I almost took offense to Dennis being described as my handler, but the way his throat vibrated his words made something in my ass vibrate too. I slipped the money into my shorts and then slipped out of what little I was wearing.

Pat squeezed my little balls with his big fingers. "Damn, Dennis has got you locked down. Almost like getting a real woman."

"You don't like boys?"

"Nah, I like em just fine. A long time ago before my wife and all the kids and all the grandkids, used to have a boyfriend. Of course, back then, I was the woman in that relationship."

"The bottom?"

"Yeah, whatever you want to call it." Pat played with my cage a little as I noticed his dark cock growing. It was uncut with a shiny veiny shaft. He was easily nine inches with a nice girth to him. Dennis hadn't been in me for hours at this point and I was pretty sure this cock was going to stretch me out again. He pulled me close again and kissed me.

His hand on the small of my back guided me to the sleeper and I made myself comfortable on his bed covered in a quilt his wife had probably made. "So, any special requests? Role play? Costumes?"

His deep laugh filled the tiny space. "Nah, nothing like that." He reached between my legs and inserted two fingers in me. When he took them out, they were shiny with cum. "Clean that off for me?"

I sucked the cum off his fingers while he caressed my smooth skin. He slipped his hand behind my head and guided my mouth to his cock. So much heat came off his crotch as I slid my mouth over him until I felt him in my throat. He slowly started pumping his dick in and out of my mouth, never going too deep to make me choke, but going right to the edge of my gag reflex. There was nothing rushed, nothing cruel, just a man enjoying his cock in another man's mouth. He said nothing as I sucked him, not even a moan. The engine and his heavy breathing were the soundtrack to our experience.

Soon, I felt a spurt of cum on my tongue, followed by another. He saw the look of surprise on my face, "That's just precum baby, the main event would fill that belly."

My cock ached in its cage. I so wanted to stroke my cock and cum with this hot fucking daddy in front of me.

He pulled his cock away from me and pushed me onto my back, placing my ankles on his smooth shoulders. He reached into a drawer by the bed and pulled out a jar of Vaseline. I had heard of this being used for lube, but never experienced it myself. He slid two fingers into the jar, pulled out a decent sized dollop, and spread it onto and into my hole. Then, still in complete silence, he pushed his cock into me until those rough grey pubes rubbed against my taint and balls.

His silence was broken with a low deep moan, sounding like a lion purring. A contented look took over his face as he reveled in the feeling of my ass all around his cock. Then he slid a hand down my leg and up to my nipple and twisted it hard. I cried out, partially from the sensation and partially from the surprise of the action. My hole squeezed him and made a broad smile appear. His other hand took the same journey and soon both his hands were working my nipples while his long black cock glided in an out of me. Occasionally, the silence in the cab would be broken by one of his low moans or one of my more feminine sounding ones.

After a very long time, especially compared to the three men before him, his pace quickened, and his hands went from my nipples to steadying himself on the bed as he fucked me. "You want my babies in you?"

"Fuck yeah sir."

He leaned over, pressing his gut into my caged cock and started sucking on one nipple and then the other. Back and forth he teased my nipples while steadily pounding into my hole. Pat took a big inhale, paused, and then I felt him release his cum. As he released, he pushed himself back up and slowly pumped more and more cum into me. His orgasm could have easily been mistaken as piss, the streams were so long and powerful in me. A few minutes passed and he stopped with a broad grin plastered across his face, making every line and wrinkle crease. A low vibration in the form of an 'mmmm' emitted from his big chest.

He slipped out of me and pulled me to my feet into a bear hug, kissing the top of my head. "Damn baby. Thank you."

"Thank you, sir. That was nice."

I thought he'd want to cuddle for a few minutes, but I had served my purpose and now he needed to get some sleep. He handed me my shoes and shorts, "Here you go baby. You have a good night."

I got dressed and headed for the door. Pat waved to me as I climbed down the side of his truck and quickly shut and locked the door.

My nipples returned to little steely points in the night air as I raced back to Dennis. I tapped on the window, and he came out from behind the sleeper curtain with a drowsy look on his face. "How was old Pat?"

"Nice dick, huge load. I don't know how long I can keep it in me." I handed him the fifty from Pat.

"Well, do yourself a favor and try, cause Billy ain't known for being gentle. He's in that red Kenworth pulling the red reefer."

"Alright, one more to go."

I walked over to Billy's truck and knocked on the door. A giant head popped out of the window surrounded by a huge mane of long black hair. His beard was so long, the lower half of it was still in the truck. "You Dennis's?"

"Um, yeah."

"Nice. Come on up."

He popped the door open, and I climbed into a dark cab lit only by a few gauges and the lights coming in through the windshield. Billy sat in the passenger seat as I climbed over the driver's seat and stood next to the gear shift. He leaned against the door wearing only button fly jeans. His massive bare white feet sat flat on the floor and his belly jiggled as he undid the one button he'd fastened on his jeans. "Take them shorts off. Give us a little spin."

"You got the fifty?"

He grabbed a worn wallet with a chain on it off the dash and fished out a fifty-dollar bill. "Here, now get them shorts off of ya."

I placed the fifty in my pocket and took off my clothes. Doing a slow spin for him, he spied the cage on my cock. Billy grabbed my balls and rubbed a little drop of my, now constant, precum around. "Fuck yeah. You're just a hole tonight."

From out of the darkness, "Damn Billy, he's a fucking sissy with his little dick clamped down."

The voice startled me. When Billy had said 'give us a little spin' I'd assumed he was just talking about himself. A man in boxers jumped down from the top bunk of the sleeper and stared at me. Like Billy, he was in his forties, but bald and skinny. He stood so tall, he had to duck down as soon as the roof of the cab slanted down. He reached over and grabbed my ass, slipping his middle finger in me. "Shit, she comes pre-lubed bro!"

"Dennis didn't tell me there would be two of you."

"Yeah, I forgot to tell him my brother was with me this trip. Don't worry, he's cool." He stood up and slipped his jeans off then sat back in the passenger seat with his massive cock slumped between his thighs. "Get on your knees and suck me."

At first, I was going to ask for another fifty for the extra dick in the room, but Billy's massive growing cock stole all my attention. I'd heard of cocks as thick as a beer can, but Billy was bordering on being a traffic cone. Even with the huge, long black bush it still looked so thick at the base. The scent of a hard day’s work emanated from his crotch as I inserted the head of his cock in my mouth. I wasn't even halfway down the shaft when my mouth ran out of room for his girth.

I was so dickmatized by Billy's big cock, I'd forgotten all about his brother. A hand played with my hole, and I heard, "Damn, how many guys have been in this fucker tonight?"

"That pussy wet for you little bro?"

"Fuck yeah," the brother said as he slipped four long bony fingers in my ass, making me moan.

"Better get in there before I wreck that cunt."

Billy's brother didn't waste any time swapping his fingers for his fairly large cock. Judging from how it felt, I'd say he was somewhere in Pat's neighborhood for size. He didn't take any care with my ass, like Pat had. He fucked me like an animal would after smelling a bitch in heat. A quick pace turned into a quicker pace while his bony features made bruises on my ass. Maybe five minutes of this artless fucking and I heard him howl and scream as he squeezed my hips and unloaded in me.

"Damn Jake, never seen you cum in a hooker that quick."

When Billy said the word 'hooker' something electric connected my nipples, ass, and cock and again I wished I could jerk my cock and cum.

Billy pulled my head off his meat. "Come on back to the sleeper."

He unfolded his massive body from the passenger seat and hunched over until he reached the sleeper area where he could finally stand up straight. Standing next to this big fucker, I didn't even clear his nipple line. He sat on the bottom bunk with his back against the wall and his massive feet flat on the floor. His enormity made a twin bed look like a bench. "Sit on it. Earn that fifty."

I turned around and slowly pressed my ass over the head of Billy's cock. Gradually I lowered myself until I didn't think I could anymore. Jake just sat and watched his brother's cock disappearing inside of me. He was the first to notice when I had hit my limit. "Fuck Billy, this bitch can't even get all the way down on it." He directed his gaze to me. "Come on whore, you still got inches to travel."

I tried my hardest to lower more and more, but my body's sense of self-preservation prevented any further progress. This did not make the brothers happy. Billy's giant hand gripped my waist, almost meeting on either side, and he shoved me down even more. I screamed out as his cock ripped me apart. I could feel his long pubes start to tickle the back of my thighs, which meant two things, one, it was almost completely in me, and two, it wasn't completely in me. "Shut this bitch up, can't have cops coming by cause she's screaming like a little pussy."

Jake obeyed his brother and put his cock, which had become hard again from hearing me scream, down my throat, making me gag and sputter.

"That's better. Don't mind it when it's muffled."

"No prob, you want me to push her the rest of the way."

"Go for it. Maybe we'll break this whore in two."

My eyes widened, partially at the thick cock impeding my airway and partially at the thought of what was about to happen to my ass. Jake put his cold hands on my shoulders and pressed me down hard onto his brother's dick. My scream escaped around Jakes's dick as the full girth of Billy overextended me.

Billy leaned me back, yanking my mouth off his brother's cock and turned my spit covered face towards him, "See cunt, I knew you could do it."

Jake lifted my small balls up and ogled his brother's handywork. "Damn Billy, you should see this gaping cunt on your meat."

"Grab my phone off the dash and take some pics for me."

The flash went off a few times as Jake took pics and Billy started wiggling his cock a little in me. Not full strokes, just getting me used to the movement. Jake put the phone back on the dash, "Can I have my cocksucker back?"

"Yeah, sure." Billy shoved my upper body up towards his brother's waiting drooling cock.

By this point, my upper body concentrated on Jake, and I succumbed to the fact Billy was going to do whatever he wanted with my lower half. As I sucked and licked on Jake's cock and balls, Billy clasped his hands under my rib cage and started using my hole to jack off with. He lifted me halfway up his thick limb and then slam me back down to the base.

"Fuck, this bitch has so much jizz in her, it's fucking amazing."

"Hey bro, I'm about to nut again, you want me to add more lube?"

"Fuck yeah, get in there beside me little bro."

Jake pushed me back, placed my ankles on his shoulders, and stared at me with a maniacal look as he watched my face silently scream at the addition of another cock in my hole. Jake slid his cock between his brother's and my taut sphincter and wasted no time getting up to fucking speed. In about a minute I heard Billy, "Ah fuck yeah, I can feel you cumming on my dick man!"

When he'd finished, Jake yanked his cock out of me, and Billy started driving his dick into me at a pretty good pace. I looked down and, for the second time that night saw a cock moving in my abdomen.

A low growl started to echo out of Billy's cavernous chest as he repeatedly slammed me down onto his cock. The pace became so extreme it reminded me of riding a wooden rollercoaster back in high school. My body bounced around at Billy's whim as his brother looked on. "She looks like a blowup doll on your cock bro."

Suddenly, Billy slammed me down on his cock, but didn't raise me back up. His cock pulsed inside me and made the lump in my abdomen jump in unison. When he'd finished, he let go of my waist and relaxed with a sigh of accomplishment.

Jake grabbed my clothes, opened the driver's door, and through them to the ground. "Come on whore, time for you to go. We got to be leaving soon if we're gonna make our deliveries in Phoenix."

I quickly pulled myself off Billy's cock and shimmied down the side of the truck, getting dressed in the dirt. Above me the door slammed shut, the brakes released, and I moved away from the moving semi as they left.

Walking back to Dennis's my ass felt weird, like there was something extra in my crack. I climbed up and knocked on the door where a sleepy Dennis let me in. "Fuck, you smell like cum and truckers." He laughed at his own joke. "Have fun with Billy?"

"And his brother." I handed Dennis the fifty from Billy.

"Two dicks should have been two fifties. You got to learn not to give that shit away for free."

"Can I ask you to look at my ass? It feels weird."

"I bet it does after that fucking tree stump of Billy's in you."

I slid my shorts down and spread my cheeks towards Dennis.

"Damn bitch, you got a little rosebud going now."

"A what?"

Dennis grabbed his phone, took a picture, and showed me.

"What the fuck! Is it permanent?"

Dennis played with it and poked at my ass. "Nah, as long as you don't let Billy fuck you or anybody fist you, it should probably go away. I ain't never fucked anybody with one."

I looked between my legs to see him rubbing his cock. "How about you unlock me, and you try it out?"

"Did you cum yet tonight?"

"No, just precum."

"Even after Billy? Damn. Yeah, I'll release your clit."

I got on my back on the bunk as Dennis undid the cage around my cock and balls. I figured I'd have an erection that would just pop out, but I was still limp to my amazement. Dennis put my ankles on his shoulders and slid his big cock into me in one effortless motion. "Fuck, that's better than any pussy."

His cock moving in me activated my own erection. I'd never been so happy to have my thin little dick in my hands. Dennis pummeled my hole while I jerked my cock, my little balls disappearing into my pelvis, leaving just a rough patch where a real man's balls would be. Before I knew what was happening, I felt a spurt of cum hit my face and then a few more on my chest and stomach.

"Fuck yeah little man. Let's add that to the mix," Dennis said wiping the cum off me and onto his cock.

My body went limp from exhaustion after I came, and I could do nothing but let Dennis use my hole however he wanted. He grabbed my nipples and made my ass grab at his cock and soon I felt another one of his loads seeping into my guts.

He rested for a moment with his ear against my ribcage. At some point I fell asleep because the next thing I knew he was waking me up. It was early morning in downtown and he was parked in the center lane with his blinkers on. "Hope the address on your license is correct, cause that's where I've brought you."

"Yeah, it's good."

"Grab your bag and I'll get your shirt out of the side box."

He climbed down as I got dressed and found my bag. I climbed down the truck, and he handed my shirt over. He grabbed me by my ass and kissed me hard on the lips. "You ever need a ride or to make a few extra hundred give me a call. I sent you a text, so you got my number."

"Thanks. It was kind of fun."

"Whore."

He climbed into his truck, and I walked over to the entrance to my apartment complex. As I waited for the elevator, I opened my phone and there was a text from Dennis. No words, just a pic he must have gotten from Billy of my ass being stretched by his cock.

I didn't know how far into the world of sex work I'd be going, but I did know I needed to jack off again.