The Night That Would Never End Pt. 06

Warning: this series depicts rough and degrading sex with some offensive language. If that's not your thing, then please move along.

As my car rolled to a stop on the dark highway shoulder, I began to panic.

"No no no, this can't be happening," I said out loud as I tried to start the dead car. It coughed and puttered and went silent. "Fuck me! What the hell am I going to do now?"

Goose bumps began to form on my nearly naked body. I couldn't believe what was happening. I looked down at myself, my black bra, my pink panties with my little sissy clit tucked in them, and I was terrified. I was way to far from home to just walk, and I certainly wasn't going to be able to push my car in my high heels and underwear. Maybe I could call a tow truck. It would definitely be embarrassing, but at least it would just be the truck driver who sees me.

I grabbed my cell phone hoping to Google a tow company, but to my horror I didn't have a signal. I was apparently in a 'dead zone.'

"Oh shit," I couldn't believe my bad luck. "Now what?" I turned on my hazard lights and just sat there, my brain turning a million miles an hour trying to think of something, anything. I didn't know what to do.

Just then, I noticed headlights in my rearview mirror. At first I was excited, maybe they could help me, but then I remembered how I was dressed and I was very aware of the tiny pool of semen that was leaking from my freshly fucked bum. As the vehicle closed in on me I could tell it was slowing down. Then, it veered onto the shoulder behind me and suddenly bright flashing red and blue lights lit up my car and blinded me.

"Ohh no," my jaw dropped, "it's a cop."

Honestly, a cop pulling up behind me was probably one of the best case scenarios in this situation. I mean, I wasn't actually breaking any laws and he could easily radio in a tow truck for me. I just wasn't entirely sure how to explain to him why I was dressed this way. I was trying to mentally prepare myself when someone loudly tapped on my driver side window.

I looked up and my eyes met a very gruff and salty looking sheriff's deputy. I quickly rolled my window down as he scanned my near naked body with his flashlight.

"Hi there officer."

"What in the world are you doing out here dressed like that?" The tone in the deputy's voice was very condescending and judgemental.

"I'm sorry, sir. I was driving home from a party and my car broke down," I explained with a shaky voice.

"A party huh?"

"Yes, sir," He continued to look me up and down, until finally the beam of his flashlight stopped right between my thighs.

"I need to see some ID."

"Of course," I grabbed my clutch, pulled out my driver's license, and clumsily handed it to him.

"Why you acting so nervous?"

"Sorry, sir."

"Haha," he chuckled as he looked at my driver's license. "This can't be you. It says here that you're a man, and clearly," the deputy looked at me with menacing eyes, "you ain't no man."

I sat there with my mouth wide open, not sure how to respond. "Uh.. well.. you see I'm a crossdresser, sir."

"You mean you got a little dick tucked away in those panties?"

"Uhh ye-"

"Get out of the car," the deputy ordered.

"Y-yes s-sir."

I got out of the car and he motioned for me to follow him to the back of my vehicle. I obediently proceeded on wobbly and nervous legs. I felt so humiliated standing there on the side of the highway in the bright light of his SUV. Questions were flooding into my mind. What was this cop going to do to me? Why did he make me get out of the car? Finally, I spoke up.

"Umm officer, I really just need to get a tow truck. My phone is dead but if you could just radio one for me I would appreciate it."

The deputy had a look on his face that said that he didn't give a shit about my problems. I was only just now getting the full measure of the deputy. He was about six three and brawny, and looked to be in his mid-forties. He had a very domineering presence and I had the distinct feeling that he was not going to help me.

"Stand here," the deputy pointed at the ground. "I am going to search your car. Don't you dare fucking move."

"Yes, sir"

I was genuinely bewildered. Searching my car? Why? I stood there with my arms crossed watching as he leaned into the driver's seat of my car and began rummaging around. I felt so on display and humiliated standing there in my heels and lingerie under the bright glow of the police lights.

The deputy didn't search for long before he came back around to where I was standing.

"Find anything," I asked with a defying tone.

He looked at me with a sly grin. "Not yet sissy boy, but from the looks of the wet sticky spot on your front seat cushion, seems you been puttin something up your ass. You wouldn't be hiding drugs up your butthole would you?"

"What!" I genuinely was not expecting such an accusation. "Of course not, that's ridiculous!"

"Place the palms of your hands on the trunk of the car."

Horrified I said, "You can't be serious!"

"I ain't gonna ask a second time."

"No, this isn't ri-" in a flash the deputy shoved me over the the trunk of my car and grabbed my left arm folding it behind my back. He had all the weight of his body against me, pinning me down.

"I said I wasn't asking again. Now, give me your other arm."

"Okay okay!"

I complied with his command, completely in shock over how quick he had just pounced on me. I reached back with my free arm and he immediately grabbed my wrist and yanked it together with the other one. Then, in an instant, he locked my hands together with handcuffs. Having subdued me, he then leaned in close to say something in my ear.

"Now, let's see if you're hiding anything up that little ass of yours." I swear I could feel his bulge grind against my ass as he was speaking, but then he stepped back off of me and put on some rubber gloves. After that, he pulled my thong to the side. I looked over my shoulder at him and begged.

"Please, please officer. You don't have to do this. I don't do drugs, I don't sell drugs, and I don't transport drugs. I've been out hooking up with guys all night. That's all."

"Eyes front sissy boy," he was determined to examine my rectal cavity. He held two fingers up, spit on them, and placed them right against my anus.

"Omg I can't believe you're doing this to MeEEEE!" He shoved his fingers right up my butt. No grace, no finesse, no interest in my comfort. It caused me to raise up off of the trunk of the car, but the deputy shoved me back down with his hand in the middle of my back.

"Come on now, you know all you sissy boys like it up the ass," he laughed as he twisted his fingers around inside me and pushed them in past the second knuckle. If I hadn't been fucked so much already it would've hurt like hell.

After exploring my ass pussy and laughing at my moans for what felt like an eternity, he finally removed his fingers.

"What's this," the deputy asks as he dropped a small baggy of white powder on the trunk in front of me.

My eyes went wide as I stammered, "what the fuck is that? That's not mine!" The little baggy clearly did not come from anyone's ass, but from the cops pocket.

"Hahaha, sure it's not, you were just keeping someone else's coke up your little sissy ass," he said, popping my thong back into place.

"What? No! You planted that on me," I cried out as I squirmed around underneath him.

"Yeah, that's what they all say. Unfortunately for you, it's my word over yours, and the judges ain't gonna trust the word of a cock loving little sissy boy like you. Guess you're gonna to be going to jail." The mean old deputy then grabbed my shoulders and pulled me to my feet.

"No wait, please! I can't go to jail... Please... I'll do anything, anything at all," I begged shamelessly.

"Hahaha, I love the way you little fagbois beg," he continued to pull me towards his vehicle, and I continued to beg as he pushed me into the backseat.

He glared at me. "You'll really do anything I want if I don't take you to jail?"

"Yes, sir. Anything at all."

He closed the door and, with his prisoner secured, the deputy went back to my car, got the keys and my purse out of it, and locked it up. I watched him as he began to walk back towards me. "This can't be happening," I thought to myself. It was all so surreal. The officer came back and climbed into the driver's seat throwing my things down next to him.

Honestly, I was feeling more hopeful now, thinking that he was probably going to drive out to somewhere more private and have me serve his cock. Then, he'd let me go. Admittedly, I wouldn't mind one more good fuck to end the night on.

The deputy started driving, pulling back out onto the highway. As he drove us away curiosity got the best of me. "So, where are we going?"

"Don't worry, I'm not arresting you."

I sighed with relief, "thank goodness."

We drove a few miles down the highway to the downtown exit. The deputy then exited the highway and drove us into this very seedy looking part of town. There were lots of old abandoned buildings with broken windows and graffiti all over them. It was very dark and dirty.

After driving a few blocks, he turned down an alley that ran between two warehouses. The alley was full of refuse and old crates and appliances. It was also very dark. This would definitely be a good place to find some privacy. Pulling up alongside a dumpster and some old appliances, the deputy parked the SUV.

I was thinking to myself, "alright let's get this over with," as he came over to my door and opened it up.

"Let's go, out."

I slid out of the vehicle, hands still secured behind my back. He immediately grabbed my arm and started walking me towards an old dishwasher that had a pallet and some cardboard laid out on top of it. As soon as we reached the junk he square up behind me and pushed me over the dishwasher.

"Don't you fucking move."

"Yes sir, officer," I had no intention of trying to get away. Could you imagine a sissy trying to run from a cop in heels and lingerie down a dark alley? I was prepared to take whatever he gave me.

The deputy put on another pair of gloves and pulled my thong to the side just like before when he gave me the cavity search. Then, I heard him unzipping his pants. Something told me that he wasn't going to be gentle with me, so I grabbed ahold of the pallet and took a deep breath trying to relax my ass.

I felt a thick gob of the deputy's spit hit my asshole. Then, I felt something large and warm rubbing the spit around my anus. I could only assume that it was his mushroom head. I was very thankful that all the other guys had already stretched me out. Otherwise, this guy would tear me apart.

He spit on my hole again and then started pushing. My hole opened as much as it could for him as he slid his massive meat into my rectum.

"Aghhhh," I moaned and gripped the wooden pallet.

"Ohh yeah," the deputy slid his penis deep inside me with little resistance. "You've got a nice little fuck hole. I'm going to enjoy slamming it."

Then, the deputy grabbed my waist and began working his throbbing cock in and out of my ass pussy. I grit my teeth and moaned softly as he laid his thick pipe inside my little sissy body. He began to buck faster and harder, the various items on his utility belt jingling and clanging around with the motion of his body.

He was really slamming his cock into me now, as I moaned like a helpless whore. He reached forward and grabbed my hair, yanking it back, grunting and groaning from the pleasure my ass was giving him.

"You want me to shoot my load in your dirty whore ass don't you, sissy boy?"

"Yes yes please, ohhhhh!"

"Well, I'm not going to. I've got other plans for this hole."

Then, the deputy yanked his cock out of me and pulled me off the pallet down to my knees. I winced at the pain of him pulling so hard at my hair, but when I opened my eyes I saw his cock right in front of my face with his hand wrapped around it.

"Open!"

I obediently opened my mouth expecting him to shoot his seed all over me, but instead he shoved his eight inch dick down my throat. I gagged and tried to pull back, but he held me there with both of his huge hands and forced his dick all the way in. His balls were resting on my chin as I struggled to breathe, tears streaming down my cheeks.

Then, with no warning at all except for a slight twitch that I felt in his testicles, his cock exploded. I retched so hard but there was nothing I could do.

He held my head against his crotch, "don't you spit up anything on my pants, sissy! Swallow!"

I gulped and gulped the thick warm fluid down, but there was just so much of it. My cheeks were so full I looked like a puffer fish, but I didn't dare let anything leak out onto his pants. I swallowed and choked and swallowed some more.

Finally, his orgasm abated and he released me. I slumped over gasping for air as semen infused drool rolled down my chin. The deputy opened the back of the SUV and produced a towel, wiping himself up. Then, he put away his spent cock and ordered me to bend back over the pallet. I thought he was probably going to use the towel to clean me up, but I was wrong.

I could hear him rummaging through his trunk before he came back over to me saying, "Now that you're properly stretched, I'm putting your little ass to work."

Work? What the hell did that mean?

Then, he dumped a bunch of little baggies of powder right in front of me on the cardboard covering the pallet. My eyes grew wide.

"What is this?"

"I owe some shady people some money. My gambling problem will be the death of me one day, but for now, all I got to do is get this contraband into the jail house and my debt will be forgotten. That's where you come in."

"What!?!?"

"I'm going to shove these baggies up your little boy pussy and then I'm going to take you to a holding cell where you will deliver the product to the guys on the inside."

I didn't like the sound of this at all.

"What? No way, I can't do that. Please," I pleaded with him but he wasn't having it. He grabbed a baggy and moved behind me. "No! No! Wait-" The crooked deputy had no trouble getting the first couple of baggies inside my rectum.

"You said you'd do anything for me. You can either sneak this stuff in and come back out, or I can book you on possession and you can stay there. Either way, you're carrying the drugs bitch boy."

"Oh fuck," I resigned myself to his will. What other choice did I have?

It didn't take long for him to get all of the little baggies inside me. Once he was done he popped my thong back in place and warned me not to let anything fall out of my asshole. Then, he put me back in his patrol vehicle and we headed down the road towards the county jail. I sat there in fear and silence the entire ride, my ass stuffed with contraband.

"I was seriously stressin' about how to get this shit in without getting caught. Now, the risk is all yours," the deputy said, full of pride and confidence.

I couldn't believe I let myself get into this situation.