First Time Training Session Ch. 02

"Hands up. In the air" he said. There goes that idea. I did as told and he lifted my white undershirt up, pulled it over my head and threw it in the truck bed. Finally I was totally naked except for my shoes. Then he pushed me so that my bare chest fell down onto his tailgate, and bending down he grabbed one of my ankles at a time to spread my feet apart so my ass was out, pointing at the highway. I heard a car cruise by. Fuck fuck fuck.

The man gave me a spank and then walked around his truck to step on his back right tire and climb into the bed. He grabbed my right hand and pulled it away from me towards the wheel well. There was a chain there hooked to the rail of the truck bed, and he clipped the ring on my leather cuff to the chain before pulling it tight, making the right side of my body jerk forward a couple inches. Then he took my left hand. Clipped it. Pulled it towards the front of the truck too, tight. My bare chest was getting scratched up by the rough metal of the tailgate, and my ass leaked out a drop of my own spit that slowly ran down my inner thigh towards my knee.

"Look at this whore" he spat at me, "How are you supposed to fight back?"

"I'm not..." I whimpered. My voice came out higher than it usually is, more raspy-it was the whore speaking.

"Very good! So smart for such a cock-hungry slut." My face smiled a tiny bit before I could stop it.

Then he stepped closer to me, and squatted down in front of me with his feet wide, bringing his cock in front of my face. He grabbed my hair and lined my mouth up with his punishingly hard cock, and there was absolutely nothing I could do about it. He shoved it in my mouth. I gagged in the new position, and he loved it. He tried to make me gag again. It worked. The metal of the truck was hot on my chest, and if he had pulled my hands any further forward in the truck bed, my cock would have been under me on the metal. Instead it was dangling just below the tailgate, so hard.

He started face fucking me again, making lots of noise, getting my spit all over. I couldn't move. I twisted my feet a little, tried to adjust to get more comfortable, but it didn't work. All it did was make my ass wiggle. I wondered what this would all look like from the highway. He started letting out hoots and yelling what a good slut I was. A car flew by behind me. Then I heard another, and was sure that it slowed down as it went by. It was torturing me that I couldn't see what was happening behind me. Im on display, I thought.

That's when what sounded like an 18 wheeler cruised by and the driver honked his loud ass horn at us, clearly taking a good long look, and the stranger pointed to the driver of the truck, smiling while pumping my face. I heard the engine of the truck idling. Please please please...don't let me hear his door open. If it did I wasn't even sure I'd be able to hear it over the slurping noises coming from my mouth. And luckily the engine picked up again and I heard the truck slowly pull away.

Then the stranger decided he was done with my face. He got up and hopped out of the truck and went behind me. He squatted down behind me and I felt his strong hands grab my ass and spread it hard. He spat on it. Then again. I felt his spit roll down the top of my ass crack, then onto my hole, pooling there, before some leaked down onto the back of my ballsack. Then I felt something I thought I would never experience. His tongue flicked onto my asshole. Then all around it, then back on it. It was so fucking amazing, almost better than getting my dick sucked. I couldn't believe how good it felt, and that I'd never really wanted it before.

Without asking he pushed one of his fingers right into my hole and started flicking his tongue around it, moving it around inside me. I heard a girly moan escape through my tired-out dick sucking lips. The next one was louder. My eyes rolled back in my head. He put a second finger into me, and it didn't even hurt. It felt incredible. It joined the first, bumping on my prostate as his tongue explored my rim. I seriously thought I might cum for a moment, and I forgot that I was chained to an old pickup truck in plain view somewhere in the country, getting my pussy licked out for the first time. I forgot how bad my throat hurt. I was going to cum.

Then he stopped, removed his fingers and walked away. I heard him head back over to the shack and I stood there chained up, all by myself. I heard a car go by. Then another. I wondered if they saw my whore ass up in the air, ready for what was coming to defile it.

When he got back I heard him place something next to my ass on the tailgate, and then I heard an unwrapping sound. It stopped, and he tossed the condom wrapper in the truck, next to my face. All of the sudden I felt so stupid. Before I came here, I never even considered that I would suck him again, much less have him try to pop my virgin cherry asshole, so it never even crossed my mind to bring condoms. I was glad he had. The condom was a magnum-mine wouldn't have fit him anyway.

"Yeah, yeah..." he said, sounding totally crazed behind me, rolling the rubber over his dick. Then he spread me and gave one more big spit on my asshole before I felt his cock head on my hole. Despite my fantasies, I never thought in a million years that I would actually take a cock in my ass. And especially not like this. In my dirtiest fantasies I had pictured giving my ass up in a shower at the gym, or in some random businessman's hotel room downtown, but not like this, dirty and exposed, literally chained up and staring at the pebbles and scratches in the bed of an old pickup, sweaty and sore. And now there it was, the cool touch of the lubricated condom stretched around his big fat cock head putting pressure on my defiantly tight little hole. And it did feel big. Like, way, way to big.

"Relax your cunt baby," he said, "relax, relax, relax it!" he shouted.

The moment when the end of his cock first touched my puckered hole was probably the best part of the entire ordeal, but what followed wasn't. I would like to pretend having my asshole stretched further than ever was the most amazing feeling ever, like I would if this were some ridiculous fictional tale of first time anal sex. But it wasn't, this actually happened, and when you take a dick up your ass for the first time and it is an especially large, thick one, it hurts. A lot.

I yelped as it pushed in just a bit, and the stranger backed away for a moment, which surprised me. He gave me a few seconds and then placed the end of his cock back on my hole. I tried so hard to relax it, and he put pressure on it. I felt it move a little and my hole strained. He had done me a favor, making me shove that butt plug in my pussy before even though the size difference was absurd between the two. His dick slipped in a bit and pain shot through me. I bucked a little and my arms pulled the chains tight. I whimpered and let out a squeal. It hurt.

"Almost, bitch..." he said to me. He gave one more abrupt little push, shooting a pain through me and then stopped there.

"Out...fuck oh my god, please let it out," I said in a scratchy voice. He didn't listen.

"There, stay right there baby," he said. We stood still for just a second, silently, as the pain gradually subsided. My focus went away from the pain and on to what had just happened. "Hows that for ya?" he said to me, "Congratulations, you've officially started." So much had already happened, I had a hard time thinking it had just begun. "You, slut, have my entire cock head in your dirty. Little. Cunt." He spanked my right ass cheek and gripped on it, pulling my ass apart and looking at his dick in me. I wished so bad I could see. I heard him pick up whatever he had put down next to me, and then that camera sound that phones make when you take a picture with one. He had taken a photo of this. Maybe I would see it. My cock swelled even more.

Slowly, he pulled the head back out, and my asshole relaxed. He gruffly grabbed both of my ass cheeks, spread them wide, and spit on my hole. Then he brought his cock back up to it and smeared it all around with the end of his dick. Again, slowly, he pushed on it, and this time the head slipped back in and my tight o-ring was back gripping around the start of his cock shaft in just a few seconds. It didn't hurt quite as bad, but didn't feel ok yet. He pushed a little more. Another bit went in, I couldn't tell how much. The friction on my asshole felt kind of good, then all the sudden fucking amazing as his dick head moved over my prostate.

"Its prom night for you girl," he said. "Not what you pictured," he continued, gradually pushing more of his shaft in me, "but what does it matter where or how its happening, what matters is that your cute little pussy is getting the stretching it deserves."

"Yes...sir," I spat out. It came out quick because I had been holding my breath. I took a few big fast breaths, and he pulled out a little. And it was true...I had waited way too long. This was so fucking hot, and now that I thought about it, it was feeling good, but not in a relieving way, I don't know how to describe it. It may sound stupid but it felt a little like the feeling you get when you are about to sneeze and it just won't happen...I couldn't tell if I had to pee or cum, or if precum was just oozing out of my dick, there was so much pressure. It felt like I was on the cusp of some insane release, and it just wouldn't let go. I could only imagine what it was like for him, it must have felt incredible. Just so tight!

And finally, I realized, I was actually the slut I had always wanted to be. Sure, I had the same thought in the stranger's apartment while he had felt me up against the wall and then squirted his jizz into my open mouth, but this was different. My virginity was gone, my cherry popped-no, wrecked. He was making my ass his toy, making all the decisions I had been too big a pussy to make on my own for me, and changing me forever. Im a true bottom. I'm a sissy cock-loving bitch, and at this point, he didn't even need the chains. I wanted him to do it.

For an instant Christy popped into my head. Then his left hand came down hard on my ass. Smack, smack! I lost her, and I was back to being owned.

Under my breath, in a slutty little voice I muttered "Oh fuck yeah...".

"What did you say bitch?" He grabbed my hair from the back and pulled my face up so I was staring at the back window of his truck. "Fuck yes I saaaaaid!" The word "said" got stretched out because as I said it he pushed another couple inches into me, deeper than he had been yet, before pulling out about an inch. My moans were almost squeaks. Then it started.

He pushed it in, then pulled out, in then out. I was getting fucked. His cock was so thick it was pulling my o-ring out with it a little as he dragged his cock out. He spit on it again, and it got more slippery. That allowed him to quicken his pace. He let go of my hair and my face fell back down to the hot metal of the truck bed. He put his hand on my shoulder, pulling me back towards him, keeping the chains tight, the cuffs pulling on my wrists. He started thrusting. I moaned with each new entry into my core. It felt so fucking intense, mostly good. Mostly.

Whoosh. A car flew by. Followed by two more. If they looked they would see his ass now, not mine, but would see my feet spread wide and my thick legs in front of him. From that angle and in this position they would probably think I was a girl, some no-limits slut. It felt like he must be up behind my bellybutton with his dick, it was so deep in me sometimes. Then, after what felt like an hour of having been tied down to his truck, he bottomed out in my ass. I felt his hip bone hit my ass cheek before he pulled his dick back out some.

"Yea...yeaa..." I said. I sounded like a girl. "Fuck your little slut daddy...fuck me like that..."

"You like it?" he said.

"Mmm-hmmm," I said, over dramatically nodding my head up and down before returning it to the metal of the truck, feeling coarse on my cheek.

Another car drove by. The driver honked twice, signaling he'd spotted us, but didn't slow. I felt so naughty. I spread my feet a couple inches further apart, as far as I could, and had to get on my toes to keep my ass high enough for him, making it bulge and showing him I wanted it more.

Clap. I thought I heard it, but I wasn't sure until a second later when he pushed back into me. Clap, clap. Clap. Clap. Cap. He wasn't being so careful now, fucking me like he wanted to, and his hip bone and groin were slapping against my sweaty ass cheeks, making that tell-tale, lustful, anti-romantic sex sound every ass makes when its getting plowed hard and deep enough. As the clapping sound got louder, his huge balls started swinging enough to slap up against my taint and the base off my ball sack. His nuts were so sweaty-I distinctly remember that part, when I first felt his balls hit mine, leaving some of his cool sweat on them before coming right back.

"Ahhh! Ahhh! Ahhh! Ahhh!" I couldn't help it. The combination of his rod dragging over my o-ring, stretching it, and the intense rhythmic pressure on my prostate was making me scream out like a 10 cent whore. The stranger grunted behind me, spanking me hard every now and then. He grabbed my hair again roughly and pulled back on it, bringing my shoulders up and making my back arch. Then he just pounded. I don't even know what noises or nasty words came out of my mouth then, I was so focused on the feelings coming from my slut hole. It was much more intense than anything I had felt while having sex with a woman, there was no doubt about that. I still couldn't tell if I was about to cum at any moment or if precum was already dripping out of me. My cock stayed hard. Cars were still passing. They couldn't see my face of course but it would only take a moment for one to slow down and turn in. That was terrifying, but I actually didn't care. I'm a whore now, I thought, and good whores don't care who sees. Good whores put on a show.

The stranger pushed all the way in and stopped, his balls smashed against mine, all wet. Then he pulled his rod all the way out. Now it actually felt weird with it out, like I was too empty. It was ok though, because an instant later he just shoved it back in, all the way. I cried out with a moan in the most innocent voice I could. He pulled it all the way back out again. Then jammed it all the way back in me, clearly enjoying himself. Then all the way back out. Then balls deep once more. Then out. Only this time he didn't immediately place his cock back in me. He paused, long enough for me to hear him let out a couple big breaths.

"Fuck," he said quickly and quietly. I didn't know what was going on. He fumbled around a little. "Well," he said, "I guess thats the problem with bringing only one," he said, tossing something onto the right wheel well by my right hand in the bed of the truck. Before I realized what it was, several inches of his dick where sliding back up into my boi pussy. Then I realized what it was: the condom, and it clearly had a big rip in it. What the fuck?! But it was too late. His bare cock was already inside me and I was already melting again, slipping back into my whore trance. The smart, responsible part of me was so shut out by the dumb, impulsive whore part of me, and I barely thought of the risks and instead got even more turned on feeling the skin of his cock on the skin of my fuck hole. The moaning came back.

"Not even a word of protest!" he said, speeding up to pounding speed. "You learn so quick baby..."

Ten seconds hadn't even passed since he'd put his bare cock in my asshole and already my whole body was bouncing against the back of his tailgate, my ass jiggling and calves sore from standing on my toes. The truck was rocking forward and back a little bit from my weight being thrown on and off it, making a squeaking noise. My hands had nothing to grab onto, and my fingers moved on their own, stretching out and clenching closed as his dick bludgeoned my prostate, bringing me closer and closer to cumming. I heard another diesel engine approaching in the distance. As it got close, it slowed and then it stopped right behind us, idling in place. I felt the stranger turn his shoulders a little, looking back at the semi-truck parked there. Apparently its presence was ok with him, even a good thing, because he turned back around and started to slam my pussy with his cock even harder, making the truck move more under me, forward and backward.

I held my breath, taking his merciless pounding, holding my eyes shut and trying not to be embarrassed. I could feel my face turning red, and I had to let the breath out. It came out as a long, high pitched "Fuuuuuuuuuuck!" that ended in a drawn out, quiet moan that wavered each time he slammed into me.

Not only was he pounding me hard, but he was using his entire length. I could feel his cock head nearly popping out when he pulled back out, and his ball sack slap my own as he thrusted over and over, that slapping noise so loud. He spanked me over and over and I was wailing...it was so good and so bad. Still the sound of that engine behind me, someone just watching me take it. I hoped the site of me getting used like this had gotten the driver of the truck hard, and that he was stroking his meat in his cab, watching. Each thrust from the stranger sent a new chill up my spine. My nipples were rock hard despite the heat.

Then, without stopping his thrusts, the stranger reached down next to me in the truck bed and picked up my wife beater undershirt. He stopped thrusting for just a moment, and it was weird but I instantly got sad and said "Ohhh..." in a tone that meant no, no don't stop it! Then he leaned in over my back, and grabbed my face up off the truck by my hair, and with his other hand he put my shirt over my head, but not like it's supposed to be worn. Instead he had put my head through one armhole, and then through the other so it was coming out the other side. I didn't really understand until he took the rest of the shirt (the lower part) and twisted it up some. As he did that, it tightened up around my neck. It got tight, but not tight enough to really choke me.

He wrapped a bit of it around his fist from the bottom of the shirt, to get a good grip. Then he pulled it tight, yanking me back by the neck and my shoulders, stopping the breath I had been inhaling halfway. The little slack that had been in the chains tightened and the cuffs pulled hard on my wrists as he yanked me back with the shirt, as if it were a leash and collar. My neck was pulled back so my face was stuck looking up, and all I could really see was the back window of the truck and its roof. The semi-truck still sat idling behind us.

Holding me like that, he used me like a thing. I was getting yanked in half, my arms holding me to the truck and the strangers strong grip on my leash pulling me back, keeping me taut. Slam slam slam slam! He was going as hard as he could. My moans were quieter because my throat was being pushed on by my own shirt, twisted up tight around me, keeping me in place. I couldn't move at all. It felt insanely good. Just pure slut with no choice. I watched the air freshener hanging from the trucks rear view mirror swinging as I got pounded.

I started getting a little light headed from being choked, and my vision sparkled a little bit as my eyes bulged and my hair fell on my face, bouncing around as my head shook with each new thrust into my ass. My mouth felt like it was stuck wide open, and I started licking my lips. Part of me wished the trucker would get out and come over to put my mouth to use, but he just sat in his truck.

As the stranger pounded me, I gradually felt something change a little. I couldn't tell what it was. It was as if his dick had gotten even thicker. Then he started to get louder, puffing and grunting and I knew his sperm was coming soon. Again I thought I might cum before him, but that isn't what happened. He picked up pace, and then with a loud moan I felt his dick expand in my asshole before releasing, then again, and again, and again. He was pumping cum through his 8.5" of daddy meat straight into the depths of my newly popped cherry. He yanked back hard on my neck as I clenched around his rod as much as I could. He grunted and yelled as he squirted his load deep in me. Moans that would have been very loud left me as high pitched, wheezing whimpers. I could feel his dick throbbing, and maybe I imagined it, I'm not sure, but I thought I could feel a wet, sloshy feeling in my ass.