Lovely Misadventures

"D-Derpy! What are you...ooooohhh." I gasp and then moan as my own employee wraps her lips around my dick.

Oookay, I guess I'm getting a blowjob from my part time delivery mare whether I like it or not. For the record, I love it. Fuck it all, you only live once. Ahh, fuck, it's throbbing so hard it almost hurts. There are so many factors contributing to my boner and i've never once in my life seen it get this big. Okay yeah, I'm not about to tell Derpy to stop, the thing's begging for a soft, warm pair of lips and a soaking wet tongue to get it all slicked up.

She's so good at it! Derpy's kind of a clutz but she's sucking me off like a champ! I would have thought she'd nick me with her teeth but she's not kidding around here! My eyes started rolling back into my head and my tongue hung out of my mouth as I leaned back against my nearby work bench and let her go to town.

After a few minutes of her bobbing her head up and down on me, I get the urge to stroke her mane so I gently place my hooves on her head and proceed to doing just that. Wow, she uses some premium shampoo. At this angle, I get a slight whiff of her silky smooth mane and I daresay it smells like some sort of honey shampoo. I find it quite odd that I notice such things while she's busy going back and forth shampooing my dick and balls though. Finally, she pops my left nut out of her mouth and looks back up at me like I'm her favorite new boy toy.

"Caddy?" Derpy panted as she looked up at my with stars in her eyes and drool all over her mouth.

"Yeah, Derps?" I cooed as I continued to stroke her mane.

"What's the standard running temperature of your engine?"

That's...huh, random. why would she ask that as she's giving me head. Eh, fuck it, I know the answer so I might as well just tell her.

"Erm...eighty-five degrees celsius." I replied.

"M-metric! Ohhh my god." Derpy squeals with glee. "What's the compression for the cylinders?"

"Fifty-nine kilograms, baby."

"S-sooo smart."

I'm starting to like this. Holy shit, she's turned on by intelligence. Why can't more mares be like that? Maybe there wouldn't be so many dumbass mother fuckers in the world if only the smart ones could breed. Here's something I know about Derpy that not many others do and it pisses me off that she doesn't get the credit she deserves. Derpy is not dumb like just about everypony in town thinks she is. I have applicants do an IQ test when I hire them and My newest little knob polisher here is one smart cookie. I wouldn't have her working for me otherwise.

"Caddy? C-can I ask you something a bit personal?" Derpy panted.

"We can't get much more personal than this." I cooed with a smirk. "Fire away before my dick does."

"I've always wanted to know. What's your IQ?"

"A hundred and thirty-nine, sweetheart."

"Oooooohhhh!!"

After letting out a scream, Derpy suddenly threw off her lab coat, sprang to her hooves and bent herself over my work bench with her tail as high as it could go and slightly held to the side. The look on her face was that of desperation and she began to pant to the point of nearly hyperventilating. Her winking marehood was soaking wet and begging for attention. I may have Asperger's and with that, difficulty with reading social cues, but I think I'm reading this one loud and clear.

"Oh, Caddy, fuck me!" Derpy screamed.

Without a moment's hesitation, I threw off my lab coat, hopped myself up and over top of my partner, set my fore hooves on the bench next to hers and shoved myself in. She was already soaking wet as was my cock from her sucking on it, so no lube required. Her pussy was so fucking silky but not as tight as others I've had. Derpy's a mom after all. Not complaining though, she's fucking amazing and I'm starting to like getting to know my employee on a whole new level.

As I pump in and out of this cute pegasus underneath me, she lets out some really passionate moans and squeals. I've mentioned before, when a mare enjoys it, I enjoy the fact that she's enjoying it, thus motivating me to work harder and increasing her level of enjoyment. It's a cycle that I tend to enjoy. Funny, just a couple short months ago, I hadn't had sex in years and now, I'm starting to get good at it.

As I pick up the pace and start to go faster and faster, the more Derpy soaks my workbench with drool. I must be doing a good job. We're both getting so into it that we completely ignore the sudden commotion just a few feet away from us. The sound of what I assumed was my engine suddenly revving up followed by a loud crash would have to wait. Right now, I'm getting a sweet piece of flank and I'm gonna fuck her til her eyes are straight. I'm glad I didn't actually say that to her, I'd have to fire myself for an Equine Resources violation. Forget the fact that my dick is inside her.

"Yes! Fuck me, boss!" Derpy screams. "Fill me-ahh! Fill me up with your big, hard piston!"

I'm not really that big but I'm quite flattered. Well, as per her request, I proceed to going even faster and slapping against her even harder. Oooh, her sweet little ass is so...soft! It's a jiggly, fleshy cushion that...well, jiggles as I rut her. More cushion for the pushin'! I like it! The best part about this whole thing is that I still don't feel winded. I guess quitting smoking is paying off.

I'm not about to splooge quite yet but I'm getting close. I wanna really get acquainted with this squishy tushy of hers before it's all over though, so I pick my fore hooves off the table and grab her just a little bit behind her cutie mark. Ohhh yeah, this is good. I think I can last a few more minutes before I cum though, so I'm gonna see that she does before I do.

After another minute or two, I ended up successful in satisfying Derpy. She made it all too clear by her passionate screaming out of intense pleasure. The concrete floor in my garage was getting soaked in her juices and in just a minute now, mine too. I don't have a rubber and I don't wanna get my own employee pregnant, so I'm gonna pull out when the time is right. Remember, my seed is really fucking potent. How, I have no idea since I'm by no means a healthy male. I'd hate to think of it getting even stronger as my health improves from my better diet and lack of smoking and drinking.

I'm about to fucking explode so I quickly pull out of Derpy, aim for the spot right between her wings and let 'r rip. Now, I have an average sized shaft but my balls are a little on the larger side, that's why I tend to fire off a few more rounds. I'm a crack shot with a gat and evidently, pretty accurate with my own piece that I was born with so I had no trouble hitting right between her wings. I've always wanted to do that and Derpy just so happens to be the first Pegasus girl I've banged. The first mare I lost my virginity to at eighteen and the second one after that were both Earth ponies.

Well, finally, we were both spent and after I was done gushing out a bunch of seed, I stumbled backward and sat on my haunches as my rod retreated back into my sheath. After standing there panting for a moment, Derpy followed suit and fell backward, landing right into my waiting arms. She did that on purpose, clever girl. We were both high as fuck from the pleasure and I held her close as we slowly came down from it.

I like her. I like her a lot. I really had no idea that she admired me so much before and I say a pay raise and a promotion to full time is in order for her. You know what? Maybe screwing my help isn't so bad afterall. Maybe I can bang her over my desk in my office at the store. Whatever I gotta do, I want this girl to be able to quit her post office job and work for me forty hours a week. Who knows? Maybe something totally beautiful could blossom from this whole thing.

"Um...Caddy?" Derpy said after turning her head to our left.

"Yeah, sweet tush?" I cooed as I sniffed her mane and nibbled on her ear.

"Was that big gaping hole in your garage door there before?"

"Huh?!"

I looked to my left just as my lovely assistant had and sure enough, my steel overhead garage door had been crashed through and my creation, the Cadillac was gone. How the fuck did this happen?! There was nopony in it to shift into drive gear! Wow, Derpy and I must have been really going at it if we didn't hear my vehicle break free. Derpy and I were both quite concerned, so we sprang to our hooves and bolted over and out the big hole to see tracks from the wheels leading towards town.

It was getting dark out but not quite to the point where Ponyville's street lamps start to glow and yet for some reason, an orange glow was indeed lighting up the sky right above town. After a moment of standing there trying to put the pieces together, the faint screams from several of the townsponies could be heard from off in the distance. Great minds think alike and Derpy and I turned to each other with our ears folded back and the looks of utter horror on our faces when the sudden realization that Ponyville was on fire dawned on us.

Derpy and I had no time to bask in the afterglow and instead had to find out what was causing our town to glow. Still covered in spunk, we both flew to the town as fast as our tired wings would allow. Once we had landed right on the outskirts, we were greeted with what appeared to be judgement day. Ponies were frantically darting about in all directions and screaming in terror. Fire fighters had their hooves full as there were more buildings engulfed in flames than they were equipped to handle and medical workers were attending to a quickly growing number of injured members of our community. What could have caused such carnage?

We had to find out who or what had caused such horrendous damage to our hometown and brought harm unto our friends and neighbors. Suddenly, a local police mare zipped by bound for the center of town, the lights and siren strapped to her back blaring away. It might be dangerous but if we follow her, we might get to the bottom of this and find out if there was a way we could help.

"Come on!" I called over to Derpy as I spread my wings and gave chase to the police pegasus.

Derpy and I wasted no time and were following right behind the officer as she zipped through the town and around buildings that may or may not have been spared any damage. As we neared the center of town, we could hear a series of strange crashing sounds followed by flurries of random debris and even ponies flying up in the air whether they had wings or not. Upon getting closer still, the unmistakable sound of an angry engine revving and wheels screeching against the streets.

Just as we rounded a corner, the police mare suddenly stopped midair and drew her revolver. Seconds later, the culprit who was responsible for the mayhem zoomed in and screeched to a halt as every officer in town rushed it. My own creation, the engine driven carriage I had spent years of my life, blood, sweat, and tears building and perfecting had been zooming around town and running down everything and everypony in its path.

"Fire!!" One of the higher ranking officers commanded the group.

I knew it simply wouldn't work. Though well intended, the low caliber weaponry that was Ponyville Police Department standard issue wouldn't be nearly enough to stop this beast. As the menacing machine sat there and revved, getting ready to charge, the officers pelted it with round after round leaving nothing but small dents and chipping some of the paint off. It was no use. After receiving a barrage of thirty-eight caliber bullets, my Cadillac screeched its wheels and charged at the officers who were unfortunate to have been born without wings. Thankfully, they all managed to dive out of the way in time but the next victims might not be as lucky.

If somepony gets killed because of this monster I created, I'll never forgive myself. I've got to stop it and I think I know how I can do that. Unfortunately, my means of doing so is at home, locked up in a safe. I have no other option though. I have to fly back home and retrieve what I will use to put a stop to this madness and save my town and my neighbors.

"Derpy! I have to get something from home!" I shouted as I prepared to make my way back. "Go and help any way you can! I'll be right back!"

Before Derpy could even think of a reply, I took off and bolted back the way I came, bound for home and my secret weapon I would use on my own creation. I worked so hard to build, polish, tune, and bring life to it but having brought it into this world, I would be the one to take it out.

My quitting smoking in a way may actually indirectly help save this town. Never before in my life have I flown so fast so far without having to stop for a breather. Thankfully, I hadn't locked my front door which bought a few precious seconds of time. I made my way to my bedroom, ripped one of the pictures off my wall revealing a safe and busily turned the knob to unlock it. Adrenaline was rushing through my blood at full bore and after a few failed attempts, I took a deep breath and slowly turned the knob to the correct digits and with after the telltale click, pulled the door open, revealing what would restore the peace.

A divine light and the sound of angels singing came from the safe as it opened and I wasted no time reaching in and grabbing out an obscenely massive fifty caliber magnum five shot revolver. The selling point was that the rounds from this baby could go through a cast iron engine block and I was about to put that to the test. Time is of the essence. I have to get back to Ponyville and put an end to this.

I bolted back to the town and saw something that just made my fucking skin crawl. The screaming had gone, there were no ponies on the streets everything was dead silent. On the plus side, most of the fires seemed to have been put out and the ponies of the town that hadn't yet been carted off to the hospital had all found a place to hide. Slowly and quietly, with my magnum loaded and secured in my holster, I trotted down the streets in search of the monster I created. My ears darted this way and that, trying to pick up any sound, any sign to give away the location of the beast I sought after.

Finally, the loud, angry revving of a hot V8 engine screamed in the distance. I spread my wings and took off towards the sound and it wasn't long before I found what I was looking for. The evil machine sported its fair share of dents and dings but save for that, it was pretty much unscathed. I built the think like a tank so taking it out would be especially difficult. The creepiest thing of all was it just sat there menacingly as it went out of its way to intentionally search for ponies to run over. It needed to die.

I can't fire a shot while flying and hope to hit anywhere near my mark. Nopony can. Plus, if I was gonna stop this thing, I had to be facing it head on and hit it in the right spot. Right through the center of the radiator which the slug would then shear the cooling fan clean off and proceed right into the engine and lock up the camshaft. Now that I knew what I was going to do and how I was going to do it, I had to get down there and just do it.

"Hey!" I called over to my machine as I plopped back onto the ground about fifty yards away from it. "I'm wide open, big guy! Come on over!"

"Bwaaamf!!" The vehicle honked its horn as it screeched around to face me.

"Whatcha waiting for!? Outta gas!?"

"Vroom!"

"Fraid you're gonna blow a gasket?! Worried about losing a lug nut!?"

"Vroom!!"

"Whassa matter?! You scared that you're gonna scrape your pretty little polished wheels?!"

"Vroom!! Vrooooom!"

Screeeeeeeech!!

"Come and get meeeeee!!!"

I've been close to death before but the last time I was, I was unconscious and unaware of my situation. Right now, I am face to face with a three ton steel machine with mini explosions happening within enclosed cylinders keeping it running. If things don't work out according to plan, the possibility of me dying is very real. With the menacing monster screaming towards me at full throttle, I make my move.

I lean back as if I were about to sit on my haunches but instead stand up on my two back legs, my left one in front of my and my right behind me, like the stance a diamond ball pitcher would take when he's about to pitch. Like a flash, I grab my hoof held cannon and take aim. As the monster I created barrels towards me with intent on killing its own creator, I cock the hammer back and line up the sights dead center with the radiator.

This gat's gonna kick like Applejack so I held on tight and waited for just the right time and the right distance between me and my own machine that I built and now wanted me dead. I took a deep breath and as I slowly exhaled as to help keep my aim steady, I pulled the trigger. The shot from the massive fifty caliber revolver boomed and echoed through the entire town. I even saw a few windows open and ponies poke their heads out to see what was going on.

Within seconds, the speed that the Cadillac was zooming towards me was rapidly decreasing and I could see that it was leaving puddles of motor oil and coolant in its wake. As it slowed down to a putt putt, I could hear the internal metal parts of the engine clanging and clacking together as smoke poured from the back end and from the new hole I had created in the front. Finally, the three ton battering ram chugged its last cylinder stroke and sputtered to a halt a mere ten feet from where I stood. After one last backfire, fluids of every kind proceeded to gush from the now destroyed machine. It was finally over.

"Caddy!" Derpy sobbed loudly as she zoomed over and hugged me tight. "You did it! You stopped it and saved the town!"

Upon witnessing me put a bullet through the beast that had destroyed so many homes and injured members of my community, ponies began rushing out of hiding and quickly lifted me up before proceeding to cheer for me. Cheering that I didn't deserve. I was the one who brought this monster unto them, all I did was what I had to in order to keep it from killing somepony. Much to the cheering crowd's confusion, I spread my wings and hopped off of them and turned around to tell them all the truth.

"I'm not a hero!" I addressed the crowd. "I'm the one who made that thing! I'm the reason ponies got hurt! I...I'm sorry everypony!"

With my head hung low in pure shame, I re-holstered my weapon and slowly trotted my sorry ass back towards home. Ponies gave me some very confused looks as I tried to hide my face with my wings. I didn't want them looking at me. They didn't seem to be angry with me but they had every right to be. I've done a lot of hurtful things to others and I've been trying to change that and redeem myself. I caused a hell of a lot of pain today and right now, I just wanted to get home, hop into bed and cry myself to sleep.

As I slowly trotted away, I could hear the now dead machine explode and I looked behind me to see it engulfed in a huge fireball as fire ponies rushed in to put it out. It made me sick to look at it. I had to get out of there. As I shed my guilty tears, I turned around and galloped home as fast as I could so a few ponies as possible could see the pathetic loser that is Cadillac Taille Finz.

All these years...totally wasted...