The Stipulation

Author's Note: The fictitious characters in this story are all 18 years of age or older.

It started out as an adventure, a low budget road trip as it were. After two weeks it had evolved into nothing short of a nightmare. We had been trying to flag down a ride all day. Now it was getting dark and the temperature was falling fast. How did we get stuck in this hell-hole? Freezing cold, no money, no food, and very little to bundle up with. It looked like we were in for another really cold night on the Interstate.

"Thanks for stopping, Man!"

"Just throw your stuff in the back and get in."

"Hold on a minute, my friend is coming too."

"Not him, just you!"

"What do you mean? We're traveling together so if he can't go, I'm not going either."

"Okay, he can come along...but you have to let me jack you off while I drive!"

I was dumbfounded. My first impulse was to step back and slam the door shut. I thought about it for a minute, we really needed a ride and besides, what could he do while driving? I mean, he couldn't rape me or anything. I explained the situation to my buddy and he agreed, there hadn't been any opportunities for getting a lift so we decided to accept his offer.

His car was a smaller, older station wagon with a bench seat. I crawled in first and had to scoot closer to this guy so my friend Chris, could squeeze in next to me. We took off down the highway, relieved to finally have a ride! The heater felt good on my frozen feet and I began to thaw.

At first, he didn't talk to us but after a few miles he asked me where I was from. I told him that we were both from California and we were just traveling. We were headed east but didn't really have a plan. Before long, the guy found my knee with his hand. "This is going to be really weird," I thought to myself.

"You guys better not try nothing, you hear me?" With that, he began sliding his hand along the inseam of my pant leg. I looked up and saw Chris staring at us, first at the man's hand, then at me. I could tell that he was every bit as uncomfortable as I was.

By now, our new friend was moving his hand closer to my crotch, searching for my dick that was tucked away in my jeans. "Undo your pants so I can see what you've got." I unbuckled my belt, unsnapped my pants, and lowered my zipper. He reached his hand inside grabbing my prick through my underwear before wandering down to my balls. He was cupping them with his fingertips and rubbing my dick with the heel of his hand.

His large hands were calloused and dry. It wasn't exactly comfortable. It took some time but eventually, I could feel myself getting harder. He tried to pull my dick out but just got frustrated. "Take them off!"

I lifted my butt off of the seat and slipped my jeans down to my ankles. He reached over and ripped my underwear off with one powerful tug! I was completely exposed with my penis pointing straight in the air! He wrapped his fist around my member and gave it a good hard squeeze. Looking over at my buddy, he said, "I need some lube over here, lean in and get him wet for me."

I could see Chris gathering some spit in his mouth. As he leaned over, the man released my cock and grabbed him by the hair before shoving his face to my crotch, effectively spearing his mouth with my erection. My friend couldn't escape his grasp and was drooling all over me. Once he was released, he was frantically wiping out his mouth and spitting into his shirt sleeve. He was desperately trying to erase the taste of my dick and the memory of what had just happened!

"That wasn't so bad now, was it? I'll bet you boys are pretty familiar with sucking each other off. Tell me, which one of you is the bottom?" I told him that I didn't know what that meant, we weren't gay, just friends. He grabbed ahold of my cock again and began stroking it up and down. It felt okay but he was a little rough.

He wiped some of my precum and brought it to his tongue. After lubing his fingertips, he started working just the head. It was driving me crazy! He slid his fingers down my shaft until the tip hit his palm and then back up. He was caressing the underside of my knob with his fingertips and then down to my balls. This just made me harder! Oh God, it felt so good! I could feel my balls stirring and I squirmed a little as I sat there with this stranger working me towards an orgasm. He must have sensed that I was about to cum when he slowed to a snail's pace, then removed his hand completely.

He reached for his belt, trying to undo his trousers but couldn't manage while driving. "Undo my pants for me, Son," he ordered me.

"That wasn't part of the deal!" I protested.

"I'll leave you two out here in the middle of fucking nowhere and let you freeze to death!" I complied and undid his pants for him. He fished out his cock and began fondling himself until he was sporting an impressive erection. "Put your hand here, Boy!" I tried not to look at him. He grabbed my wrist and brought my hand to his throbbing cock. "You do what I say, you hear me? Now make me cum!"

I reluctantly moved my hand up and down, caressing his thick shaft. "Give me some lube, Boy!" He wrapped his arm around the back of my head and brought my face to his lap. His cock was pointed straight at my mouth. "Lick it!" He demanded. I extended my tongue until I touched the tip. "That's it, nice and easy. You ever wanted to suck a cock, Boy?" I shook my head, no. "Well you can suck Little Henry right here, right now!" He pressed my head down sliding his dick into my mouth. "Now suck, Boy!" I drew in my cheeks and he released my head to grab ahold of my cock. I was sliding my lips up and down his shaft trying not to break the suction. "Ooh, that feels good!" he moaned. It wasn't so bad. I was in control and I liked how I was keeping him hard using just my mouth while he was jerking me off!

"Come over here, Son," he was talking to Chris. "Put your lips right here," indicating the head of my dick. "Do it, I said!" he yelled. Apparently resigned to his fate, Chris leaned towards me and bent over, taking the tip of my cock into his mouth. I was blowing this guy and my friend was blowing me while I was being jerked off at the same time! I knew he was getting ready to cum because his shaft began to pulse in my mouth. I didn't want finish him like that so I raised up and continued stroking him with my hand. "Take it Boy, take it all in your mouth!" I protested but he grabbed my head and forced me down on him. He was thrusting, harder and faster while holding my head. He was so big! I couldn't take it all. I thought I was going to choke to death!

I was helpless as he continued to ram my throat. Finally, he tensed up and "Arrrgh, Uhg, Mmmm, Ahhh," he blasted his hot load into my mouth. I didn't know where to spit. I sat up and leaned back as he kept jerking me off. I was on the verge of cumming. I think my buddy was really getting into it too. He had his pants undone and was helping himself as he followed this guy's hand job up and down my shaft with his lips. I shot my wad into his mouth while he kept on stroking himself. He slid his lips from my dick, capturing my deposit. He sat up and started shooting cum all over himself and the guy's car. "You better not spit, either one of you!" We looked at each other and gulped down the nut milk that was trapped in our mouths.

"We are going to stop up here and get some gas, so you guys get yourselves together." He pulled into a truck stop, alongside the pump island. "You boys wait right here. I'm going to go inside to pay and get us something to eat."

This was our chance to get away from him! Should we grab our stuff and run? Should we stay and risk being subjected to more of this guy's fantasies? It was a tough decision. We decided that we didn't want to freeze to death and he probably wasn't going to kill us, at least not right away. As long as we did what he said, we should be okay.

He came back to the car carrying a large pizza. After filling the tank, he parked the car and we gorged ourselves on the truck stop pizza. It wasn't bad. After eating, we both went inside and used the facilities before getting back on the road.

As we approached the car I shouted, "Shotgun!" meaning that I chose the outside passenger seat first. Chris was going to have to ride bitch this time. Once we slid inside the car, Henry decided that he was too tired to drive and volunteered Chris. He opened his door and told us to scoot over. He got in on the passenger side next to me. I slid as far over to Chris as I could but there was no escaping him.

The next few hours were uneventful as Chris drove and Henry passed out on my shoulder. His breath was overpowering so I turned away from him and focused on keeping Chris awake as he drove into the wee hours of the night. Henry had been sleeping pretty hard, even snoring at times. Suddenly, I felt his hand on my leg so I turned to look. He gazed up at me with a sinister grin and gave my leg a squeeze.

"You be still, Boy. I'm not going to hurt you." He undid my pants and pulled them off of me. He began softly rubbing his hands along my thighs and up to my balls. He reached into his pocket and produced a small bottle of lubricant. He poured some on my cock and stroked it until it was nice and hard.

He undid his pants and took them off too. He kept me hard as he worked his semi erect mast to full staff! "Get down on the floor, Son," he ordered me. I got on my knees, facing him. He was fondling his balls and stroking his big dick just inches from my face. "Show me what a good little cocksucker you are!" I brought my lips to the tip and licked it. He tensed and took in a deep breath as I covered the helmet and explored it with my tongue. I slowly took more of his manhood into my mouth, flicking and sucking. It could feel it growing as he rhythmically thrust deeper and deeper!

"Now turn yourself around and rest your head up on the dashboard." He grabbed my butt checks and spread them apart before sticking a finger up to my virgin hole. "Ooh boy, yer tight!" I cringed at the thought of what was to come. He took some more oil and worked his meaty digit into my rectum. I grabbed my cock for comfort as he pressed in more and more, widening my opening. He shoved his finger in even deeper before pulling it back out, replacing it with a larger one. He was stretching me and it kind of hurt. Pleasure and pain, what a concept! He pulled back out and took me by the waist, "Have a seat, young man," as he lowered me onto his rock hard member. "Just ease yourself on down on it, a little at a time." I was busy keeping rhythm with my hand. It was a good distraction from the burning sensation in my rear.

I felt the head pop in and the initial pressure subsided. He put his hands on my shoulders and began pressing down. I tried to resist but he was too strong. Intense pain washed over me, it felt like he was tearing me apart. "Yer doing good, Son. Now just rest like that for a bit then we'll bring her home!"

He raised himself off of the seat with me on his lap, pressing me against the dashboard and windshield. He was on top of me and under me at the same time! He was shoving his cock into my ass harder and deeper. I lost my grip on myself and just held on, trying to escape in my mind! "This isn't happening, this isn't happening!" I cried to myself as he pummeled my back door.

The burning in my asshole subsided once he came. He was still rock hard as I could feel it stretching me but it no longer hurt like before. "You feel that, Boy?" How could I not? "That was one fun ride, wasn't it?" What do you say, we do that again?" I didn't say anything. "Aw, don't be shy, let's go!"

He reached around and took my cock in his hand and slowly slid his out part way, then back in. He was keeping time. Stroking my dick with his hand while stroking my asshole with his big cock. This felt much better and I was actually starting to let myself get into it. The combination of him jerking me off while reaming my ass, I didn't want it to end!

I wanted to cum so bad. He kept it up, bringing me closer to the edge with each stroke. It was like I was being double penetrated. The feeling was euphoric. Faster and faster he went. My heart raced as the levels of pleasure stacked one intense layer on top of the last! "I'm going to cum, I'm cumming!" I was over the edge and he jammed his cock as far in as it would go and held it there. I felt him pulse over and over as he unloaded in me for the second time.

"Damn Son, yer a pretty good fuck! Now sit your ass back down and clean me up." Chris had a weird smirk on his face, grabbing himself with one hand and steering with the other. He had been spared, for now!