A Trucker Makes an Offer I Cant Refuse

My heart was thumping as I pulled into the roadside stop on I77 just 10 miles south of town. I slowly locked up the car and looked around for an Atlas Moving Van.

Time seemed to be in slow motion as I walked to the rest room. I wondered if Sir Jack was watching. I leaned over the fountain for the first of three drinks – signaling Sir Jack that his new “boy” had arrived. After each I did the stretching demanded, and then the arm and leg flexes, and the bent over toe touches with my ass facing the van.

I thought the drinks and exercise would relax me, but my anxiety level was too high. My mind raced between thoughts of thrilling adventure, warnings of tremendous danger, and guilt for shunning my respectability and turning off my responsibility gene. My needs for a kinky adventure, surprisingly over came all the odds in winning the battle of my conscience.

I just had to play out my fantasies, or be tormented forever by what might have been the adventure of my life. If Sir Jack didn’t come on too strong – I most certainly would crawl into his truck and go off with him as his boy.

As I finished the toe touches, I went on to the building to relieve myself in anticipation of what could be a long journey into the unknown. As I did my business, I suspected Jack had run. I was disappointed, I was sure he had seen my age, and portly figure and just driven off.

When I stepped back into the sunshine, and saw that the Van was still there, my anxiety returned three fold. I think I waited by the fountain as instructed. I was so nervous, and I was eyeing every solo guy that walked my way. Seeking to identify Sir Jack, and then decide if I should run.

A deep, husky voice from behind, said, “Hey boy, don’t turn around, just go get in the truck. You’ll find the cab unlocked, and instructions on the dash.” The frog in my throat answered “yes, Sir” as I walked toward the truck and pondered thoughts of running. Perhaps, because Jack did not follow, I kept going toward the van. Soon my chances to run would be gone. It was a thrilling walk on the edge.

There was only one Atlas Van. I had never been near such a big truck, a Navistar. I assumed I’d be a passenger, but that door was locked, so I checked the driver’s side and found it open. Jack wasn’t there as I sighed took a deep breath and climbed in the cab and sat behind the wheel. I was awed by the impressive rig, and was thinking of locking the door more than of pretending to be a truck driver.

Eventually, I looked up and saw Sir Jack standing impatiently in front of the truck. He was a tall, rugged, weather worn, middle-aged man most assuredly either a trucker or a Hells Angel. Besides the worn jeans, tee shirt with leather vest, and belt with keys on a long chain, he was wearing a no-nonsense look. He was athletic, obviously fast enough to prevent my escape, and strong enough to hold me. He could easily whip-my ass. My laugh was shallow as I realized I had searched the web for someone to do that, and he had eagerly volunteered. “Damn, be careful what you wish for.” I thought.

I found the instructions and started to read them. It said do each item before reading the next. Don’t stall, or your ass will be very sore the whole trip.

1. Strip completely, and hang your briefs on the mirror.

“Oh my god”, I thought. “It starts here, in public!” I sighed, slowly started stripping. I was glad to be hidden by the tall rig. I picked up the pace once I had committed, and further realized the delay warning might come in to play. I was embarrassed as I hung the briefs on the mirror. They were so easily recognizable. I looked around to see if anyone in the cars and trucks around had noticed, and then I looked at Sir Jack for some sort of approval. He just stared, and looked impatient. I was sure his stance and glare would draw other to see my embarrassment. “What now”, I thought, then I remembered there were more instructions, and I couldn’t stall.

2. Put everything you own except your briefs, wallet, and car keys in the garbage bag and throw it out the window.

I felt very vulnerable as I complied with this request. Sir Jack took the bag, carried it to the dumpster, and threw it in.

I realized this was getting to be a serious commitment, I couldn’t run away naked. I took comfort that my trucker Dom had saved my keys and wallet. Undoubtedly, when I returned I would be searching through the dumpster in the buff before I could drive home. Was Jack expecting to enjoy that comedy? Always hopeful, I took this as a sign my trucker had a sense of humor. Then I started wondering about when they emptied the dumpster, or how much trash might be added before my return.

God I hope I was returning. I had trusted my cyber feelings about Sir Jack, and was realizing I was betting my life on my judgment. Sir Jack was tapping his foot, and looking at his watch, I had better move on. Subs shouldn’t think too much.

3. Put your keys and wallet in the glove box, and get the new toy and wear it. Then show me you’ve done this.

I was glad Sir Jack was considerate enough to give me a safe place to store my valuables, that is all except the family jewels. But my pleasure was short lived as I discovered the butt plug and Astroglide in a brown bag. Fortunately, a Mistress had given me some practice wearing this device, so my concern was primarily with how long I might have to wear it, and discretely showing him it was used in this public place.

“Yeowwww” I forgot how it burned when you hadn’t done it for a while. I looked up. “Oh shit”, Sir Jack has company. He was talking, obviously sharing my predicament with three other voyeur truckers. They were howling, over my reaction as I slid the butt plug in and yelped like a dog. When I finished, they were making “binocular” gestures and pointing to their butts. The wanted to see it in me, and Jack was again looking at his watch. “Oh shit.” I said. I took another deep breath, looked about to avoid glares from innocent strangers, and the turned and gave them a shot of my ass. I wiggled my ass for their enjoyment, and then sat back and watched them laugh.

4. Climb in the back, put on the handcuffs. Snap the locks shut. Don’t think of untying the ropes securing the cuffs to the cab roof.

I found two padded cuffs each with a “D” ring attached to a rope. There were two padlocks, with no keys. My arms were soon locked with rope bindings forcing me to sit in the middle of the back seat. I was busy trying to figure out how to close the cuffs and lock them with my teeth and hadn’t noticed the voyeurs standing on the running boards watching. As the last lock snapped, Sir Jack opened the cab door, and said, “Are you comfy boy?”

I don’t know whether I was slow, or I mumbled, but my answer wasn’t satisfactory. He smacked my face, and said “Speak when I ask you a question boy!” He then reached back to adjust the ropes so my arms were spread and raised high above my head.

I was embarrassed as he pinched my nipples, and then tied a small rope around my cock, and balls. The rope separated and confined the balls holding them away from my body. He tugged pulling them up and away. He saw me getting hard, and said, “You like that boy? I was embarrassed, and hesitated. He again slapped my face and said, “Sure you do boy – but you don’t learn easily.”

With that he slipped, a chain with nipple clamps on me, and asked, “You comfortable boy?” I quickly said, “Yes Sir” to avoid the smack, but I got it anyhow. “Don’t lie to me boy! these hurt good.”

As he climbed into the driving seat, my mouth smarted and I was glad he wasn’t going to mess with me any more for a while, and he wasn’t asking me any more questions.

The voyeurs, still watching from the running boards, wanted in to the cab to play with me, but Sir Jack told them to buzz off, he had to get going, he had a date with destiny.

He gathered the rope from my nuts and one to my nipple chain and tied them to his gearshift. He started the truck and pulled out on the free way. As he shifted gears, the attached ropes tugged at my nipples and nuts.
Some shifts were quick and the pull much too far for my liking. When I yelled, he chuckled, pleased with himself. I was surely off on an adventure, and my comfort wasn’t too important to Sir Jack.

As we drove south on the highway, he interrogated me, and trained me as his boy. I learned my name was now “Asshole”, and that I was his pain slut with no rights. I learned to answer, loudly and quickly so, he wouldn’t yank on my tits any more. And I learned to always call him sir. I was to thank him for his punishments. I was not to speak, unless asked a question, and I was never to speak to others without permission. I was to ignore others and do as I was told.

He was going to whip my ass soundly as soon as he had a chance, so hard that I wouldn’t want him to do it again. But he would do it again. In fact, he would test my obedience again while my ass was still flaming. But the second whipping would be nothing compared to what I would get if I ever showed disrespect in public

He had me worried, but scared me further, when he started talking about having me suck his cock, and letting his buddies all fuck my virgin ass when he was done with it. He mentioned some whores at a truck stop up ahead that would want to play with me wearing strap-ons. They would show me how big a dick a man’s ass could take.

We had some slow time, and I reminisced about what I knew of him. When I met him on the web, we had said neither of us wanted sex and so our relationship would be non sexual. . But now I was worried. He may have lied; I was in no position to negotiate.

I started to remind him I was worried about aids, and this sexual activity. He said “Shut Up: Boy, I didn’t ask a question. I don’t need your fucking permission.” He had me scared to death. My conscience piped in ” What were you thinking Asshole.”

Soon thereafter, he was talking on the radio to other truckers. They all knew about me being in the back, and referred to me as Jack’s Virgin Ass. They asked him to put me on, and he said, “10-4″. I thought they meant the radio, but I soon found he had a web cam on the dash. Soon Jack’s Virgin was on Webcamnow and after a while, all the drivers in the country seemed to be watching my cock as Sir Jack pulled the strings. They begged Jack to show me off, to do things like suck him, take his cock up my ass, piss, swallow piss, and eat shit. Other things were much too vulgar to mention. Sir Jack just said. “Maybe later, Good Buddy”.

By the time we reached Canton it was dark, I had a sore ass inside and out, my nipples, balls and arms were numb.

Jack was talked into taking a break at a truck stop where a gang jumped on the running boards to see me. Jack jumped out and had a talk with them. Soon he came back, and as they watched he released my nipple clamps, and cock rope. Then he untied my wrist ropes one at a time, and clamped the cuffs together by using a leash.

Not too gently, he pulled the leash and pulled me out of the truck. He said, “Now we are going to find out if you learned all your lessons boy.” He walked me through the crowd towards some trees at the back of the lot. I was so embarrassed by the parade in my nakedness, and the truckers were so vile, foul mouthed, and disgusting. It was hard to ignore them. I was so vulnerable and scared. I was so dependent on Sir Jack.

Jack took me by a tree and told me to piss like a dog, lifting my leg real high, and then turning and switching legs. I did as he said, and the guys laughed. He then had me bend over with my ass facing the gang. He yanked the butt plug out of my ass. “Yeowch”, I cried.

He kept me touching my toes, and said. “Look up boy. Open your mouth, your gong to need a gag so the neighbors wont hear you cry as I whip your ass.” He then shoved the butt plug into my mouth and tied it there with a rope. The taste was awful and it extended into my throat and was truly a gag.

He led me back into the woods, and bent me over a fallen tree. Tying the rope so I stayed bent over. He then took off his belt and said, “This ass whipping is going to teach you a real lesson boy, and it’s going to be a good one to save you from these vultures that want to fuck you.”

With that he lit into my ass, as the vultures gathered around, cheered and counted the strokes. Soon I danced around and was kicking. I was dancing too much, and the crowd wanted me held, and the gag off so they could hear me beg and cry.

Sir Jack agreed. So I was sure he was going to do whatever the mob wanted.

Two guys held my arms and shoulders as jack removed the gag and had me spit out the butt plug. I noticed several guys started jacking off and they were asking Jack to let them fuck my ass when he was finished. Jack seemed to ignore them, but he really lit into my ass then. The whacks came hard and fast as the truckers counted. I was crying and begging, but he wouldn’t stop. The guys laughed and urged him on.

My strength left my body, and the guys were no longer interested in holding me up. Jack sat on a stump and put me over his knee. He said I was his boy, and deserved to be spanked by his bare hand. I kicked, begged and cried, as he kept smacking me. He wouldn’t stop. When I passed out, they tell me he stopped, and the crowd dispersed. He sat with me on his lap till I came back. “You need some more boy?” “No Sir, thank you Sir”, I said. He smiled and said, “Good Boy”!

Two guys that knew Jack stayed behind, they offered to clean me up and put me in the truck, while Jack took a break. He uncoupled my arms and reconnecting my wrists behind my back. They lifted me up and comforted me while I regained some strength. They took me to the truck stop, and bought me a shower. I got to see my red ass in the mirror, and the brutal welts. They drug me into the shower, and turned on the cold water. “Yeow!”

While I was in the shower, I heard them talking to Suzy, a woman who had heard from the other truckers about the whipping. She came to check to see if I was okay. She was compassionate, and bossy. She peeked right into the shower. “Jesus Christ”, she said as she saw the welts on my ass. “Free his hands.” she commanded. The guys said they couldn’t, as they didn’t have the keys, and I was Jacks “boy”. They said they were just caretakers, and had to put me in Jacks truck. Sue stormed out, only to return a few minutes later.

She climbed in the shower with me, and washed me, being tender with my ass. Then she gently dried me off, and put an ointment on my ass. I felt so dirty. It was nice to be washed, even in this humiliating way.

She said, ” I hate to give him back like this, with those welts. Jack had better leave his ass alone for awhile”. I resisted wearing the clean panties she brought for a bad aid, but the guys liked the idea, and restrained me and it was done. As they walked me to the truck, they schemed about surprising Jack. I was quiet; I hadn’t been given permission to speak.

By the time Jack came back to the truck their evil dead was done. I was in a red tube top, a yellow miniskirt, and black seam hose held up by a black garter belt. I wore a blonde wig and too much make-up. The guys especially liked applying red lipstick, and light blue eye shadow. They had some help from a couple of the trucker’s wives or girlfriends. I was given a shoulder purse loaded with tampons and a negligee.

Charley came back with Jack. He climbed in to drive the truck while Jack climbed into the back with me. Jack whispered, “You going to do as I say boy?” “Yes Sir” I answered as I thought, “This is Part 2, the test”. I was scared as hell of obeying what was next, but more so of the spanking that was promised for not obeying. Jack said, “Nice outfit!” He released my hands and removed the cuffs. Now get over my knee slut.

I didn’t hesitate, and I heard a laugh as he found Sues lacy white panties on me. He said, “Leave them up boy”. He gave my cheeks 5 sound smacks, and I didn’t cry or beg. When finished he was gentle, massaging my ass. He asked me to strip him, and play with him till he fell asleep. I gently removed his shirt, then his boots, socks and pants. He wasn’t demanding, as I was doing as told. I was eager to get him to sleep.

I smiled, as I pulled off the Flintstone Speedos he wore special for this occasion. Then I gulped as I saw his huge, uncut cock start to grow. He liked me watching, and couldn’t help but get an erection. I teased his chest, and played with his nipples and watched as his cock stayed hard and became moist.

He slid his hand under my skirt and up my hose to the crotch of my panties.
He played with the moist cotton there. He motioned for me to play with him. I slid my hand down to his cock; I traced the large veins out to the wet tip. I drew circles in the precum at the tip of the head.

He whispered in my ear, “No Sex!” I responded, “More precisely, No mixing body fluids Sir. He said “Anything Else?” I said “No Sir – except I am your boy.”

He shouted, “Hey Charlie, up on the visor, there are some condoms, throw them back here.” He looked at me and said so Charlie could hear, “Suck it Boy then take it in your hot red ass,

I slipped a condom over him, and soon had lipstick all over his shaft. He stopped me, before he came, “Not so fast bitch!” He pulled off the condom, and pulled down my tube top and pinched my nipples. He pulled the condom off, rubbed his cock on my nipples and then stroked his cock. He shot his cum all over my breasts.

He then had me slide my cock out the side of my panties, and stroke it for him while he twisted my nipples. He stopped whenever I was close to coming. After, three teases he warned that if I came he would fuck my red ass. Then his teasing didn’t stop and of course I shot my load. He pulled my briefs off the mirror, and had me clean up my mess.

As I did he put on another condom, and stroked himself, while rubbing against my panties. Soon he was again hard as a rock. He ordered me over his knee and warmed my panties real good. He pulled them down, and started some serious strokes. It didn’t take long to heat my ass and make me beg for him to take me. It was the only way I could get him to stop. But Jack doesn’t stop till he’s ready, so I was soon really begging for him to fuck my sorry ass.

He put me on my back with my legs up braced above my head against the cab roof. He used the Astroglide to lube my asshole, and his condom. “My god, he is going to fuck me while I watch. I am a slut now,” I thought. He was so thick and long I knew this would hurt. He stroked a few times and thrust once, all the way in. My god that hurt, and continued to hurt – it was so filling. He fucked me slow and hard, then long slow strokes for a while. When he got close to the edge he stroked short and fast. My god, I hadn’t expected a hard on, and to cum for him, but I did cum before he did.

As we collapsed in exhaustion, I heard Charley giggling on the radio. “God Damn, I forgot about the web cam.” Charlie broadcast the whole thing to the truckers of America.

Jack and I slept. Sometime later Charlie stopped on the highway, giggled my arm, and spoke to me. “Here’s where you get out ma’am. He was by the roadside rest where my adventure started. I got out, grabbed my keys, and wallet, said goodbye, and walked past twenty trucks, parked for the night, to get to my car. No one was up, but several had a pair of jockeys hanging from the mirror. They all knew I was coming. Actually, they saw me coming and Cumming.

I didn’t retrieve my clothes from the dumpster. I just straighten my skirt, hose, garters, tube top, and wig and cleaned off my makeup. I drove home with the top down on my convertible and the wind blowing in my skirt, where it reminding me I had lost my panties and my virginity in the truck. Soon a truck passed me on the right side. The driver honked, signaling I was one real hot babe and stayed beside me.

I said what the hell, and pulled my skirt up enough to expose my garters, then I stroked my pussy while he tried to stay on the road.

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A Trucker Makes an Offer I Cant Refuse, 10.0 out of 10 based on 1 rating

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