The Night That Would Never End Pt. 01

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

It was a random Tuesday night and I was all dolled up and horny as hell. I was wearing a cute purple dress, hot pink thong, and my favorite heels. I had been watching porn and playing with my favorite dildo, bouncing up and down on it, but that just wasn't doing it for me anymore. I needed a real dick from a real man.

I checked my Grindr account and, lucky for me, a guy had messaged me just a couple of minutes earlier. I opened the message to see a picture of his perfect seven inch circumcised penis along with the following message: I read your profile and I need you to come service this cock. I'm at the Red Roof Inn room 222.

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I should point out that my profile says that I'm a depraved sissy slut that likes to be used and abused. Degrade me and humiliate me. Spank me, slap me, choke me, spit on me, and piss on me. Use me as your fuck toy.

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I checked out his profile and saw that he was probably in his forties, slim, muscular, and scruffy looking. He even looked just a little dangerous and mean. In other words, he looked like he was just my type. I responded back to him: Are you into crossdressing sissies?

He immediately replied: I'm into throat and ass.

I assumed that was a yes and I told him to give me a few minutes to get ready. After about ten minutes, I was putting the finishing touches on my make-up when he messaged me again: Have you left yet?

I told him I was doing my hair and make-up to which he replied: Fuck that, just get your ass over here.

Wow! I thought. He must really just want to pound out a load! Not wanting to keep a hard cock waiting, I quickly made my final touches and headed for his room.

After arriving at the motel, I thought it would be fun to walk across the parking lot in my short dress and whore heels, so I parked in the middle of the almost empty lot and sashayed my way across the black top, signaling to anyone who was looking that I was horny and on the prowl. His room was on the second floor so I headed up the stairs. I felt incredibly cute and a little slutty as I climbed the stairs in my short dress, breeze tussling it around. My heels clicked on the hard concrete and as I approached his room the door flung open.

"About fucking time. Get in here," he commanded. He wasn't wearing anything but his boxers and I could see his semi-erect cock already forming a tent, straining against the white fabric as if it were desperate to come out and play with me.

"Yes, sir." I replied, stepping over the threshold and into the room. His room smelled strongly of cigarettes, but before I had a chance to really take in anymore of the surroundings, he barked at me to take my clothes off as he quickly dropped his boxers and got on the bed.

"Hurry up," he said. "You've already kept me waiting long enough." He voice was the kind that demanded to be taken seriously. my heart was actually racing as I quickly dropped my keys and purse on the dresser and pulled my spaghetti straps off my shoulders letting my dress drop to the floor. I then kicked off my heels and started to walk over to the bed when he, in a booming voice, said, "remove the fucking bra and panties too!" I guess he really wants me completely naked, I thought, as I quickly took off my undies and climbed up on the bed.

He was laying in the middle of the bed with his legs wide apart and his torso against the head board, so I climbed up right between his thighs, heading straight for his already hard cock.

"Suck this dick, bitch." I love it when guys call me dirty names!

I ran my tongue from the base of his cock all the way up to the tip, taking in his musk and body heat along the way. After teasing the head by swirling my tongue around it for a few seconds, I licked up and down his shaft lubing it up with my saliva. Then, without using my hands, I sucked the head of his penis into my mouth and started sucking him off.

I could tell he was enjoying it by all the noises he was making and by the upward movement of his hips. I thought I was doing a great job masturbating him with my mouth, but he wanted me to go deeper. He grabbed my head with both of his hands and started to aggressively push my face down on his cock, while bucking his hips up.

"Swallow it, whore!"

As he thrust his cock down my throat I gagged and coughed up saliva all over his dick. He did it again, and again, my body retching with every thrust causing me to cough up more and more saliva. Finally, he started to fuck my throat. In and out he pumped his cock, holding my head steady while thrusting his hips up. Before long tears were running down my cheeks as I gagged and whimpered at his assault on my throat. I was a slobbery drooling mess. He drilled my throat for what felt like an eternity until finally, sensing that I couldn't take anymore, he pulled my head off of his prick.

"Lick my nuts," he ordered me, as he shoved my face into his ball sack. "What kind of sissy doesn't know how to deep throat a dick, huh?"

I tried to say that I was sorry, but he probably couldn't understand me since my words were muffled by his big hairy balls in my face. He pulled my head off of his balls and slapped me hard, "answer me, sissy faggot!"

"I'm sorry, sir."

"Sorry for what?"

"I'm sorry I couldn't deep throat your cock."

"You mean you're sorry for being a worthless whore?"

"Yes, sir."

Then, he gave me another open-handed slap across the face. "Your ass better be a better fuck than your throat, bitch." The man then rolled off of the bed and walked around behind me grabbing my ankles and pulling me all the way back until my legs were hanging off of the mattress. With a very hard smack on the ass he said, "Get that ass up and spread those cheeks!"

Planting my feet on the floor I lifted my ass up while keeping my torso down on the mattress. I then reached back and grabbed my plump white butt cheeks spreading them open and giving him access to my tight sissy pussy. As soon as the flesh was parted I could feel him spit right on my butthole and then, much to my surprise, I felt the warm tip of his cock pressing against it.

"Wait!" I shouted, "I have lube in my purse!"

"Nah, bitch. I'm good."

I couldn't believe what I had just heard. He wasn't going to use any lube. What!?!? I started to protest, but before another word left my mouth he pushed his engorged cock against my anus and POP!

"FUUUCK!" I cried out, as his mushroom tip breached my sphincter. Releasing my ass cheeks, I grabbed at the sheets as I tried to get away. He latched onto my hips and held me in place. "Oh shit!"

"Come on, bitch. Take this dick!" He then thrust more of his cock inside me. I struggled in futility, my legs flailing about, as he continued pushing more and more of his member into my rectum.

"Oh god, please... wait..." I begged, hoping for just a moment to allow myself to get used to his fat cock inside of me, but he wasn't listening.

"Take it!" He growled as he pumped himself balls-deep inside my hole.

"Ohhhhh fuuuuuuck!" I whimpered again.

He held himself there, deep inside me for just a few seconds. "Now, you're going to get fucked like the little sissy faggot you are, and you better not fucking run from me. Understand?"

As I laid there, gripping the sheets with this stranger's penis stuffed inside my ass, I realized that this is exactly what I was looking for; a rough degrading fuck.

"Yes, sir." I whimpered.

"Good whore."

The man began to fuck me hard, ramming his cock inside me with intense force, his hips slapping against my butt, as I moaned and sobbed at the brutal onslaught that I was receiving. My sissy clit, which was tucked down against the mattress, was leaking with pre-cum as his swollen phallus rubbed against my prostate.

This went on for a while before he finally drilled into me balls-deep once again and, holding tightly to my hips, pulled me up off of the bed and to my feet. He was considerably taller than me, so as I came to my feet, standing up-right on my tip-toes, I was completely impaled on his cock.

"Holy shit!" I exclaimed as I grabbed his strong forearms for balance.

"Your tight ass is definitely a better fuck than your pathetic throat." He complimented me. "But you spent so much time making yourself look like a girl you might as well enjoy it."

Then, he proceeded to walk across the room towards the vanity mirror while essentially carrying me on his cock. The feeling of walking across the room on my tip-toes impaled on this guy's fat dick was incredibly intense. When we got to the mirror, he bent me over the hard counter and, grabbing my hair, yanked my head back so that I was looking in the mirror.

"Look at yourself, fuck meat!" He growled in my ear. My face was a mess. Mascara was running down my cheeks, my eye shadow was smudged, my cheeks were red, and my face was covered in my own saliva.

The man began to fuck me slow and deep. He pulled my hair with one hand and he reached around and wrapped the other rough hand around my throat, choking me. I looked at myself as I winced with each thrust, my face turning red then blue from the lack of oxygen.

"No wonder you like to dress up and get fucked like a skank. Look at that pathetic dick." I looked down and saw my uncut penis shriveled and flopping around with a string of precum dripping from it. I closed my eyes, and just when I thought I was going to pass out, he relaxed his grip allowing me to breathe.

Slapping me hard across the face, he said, "don't you fucking pass out on me slut! Open your fucking eyes!" I did as I was told. "Look at yourself and tell me what you see."

I looked at myself in the mirror again as he continued to stab my ass with his cock. I tried to respond between thrusts. "I see, ungh... A cheap, ungh... Whore, aghh... A dumb fuck doll, ohhh!"

"That's right. You're my little sissy fuck pig aren't you?"

"Yes, sir unggggh!"

"You love being treated like trash don't you?"

"Fuck yeah! Aghhh!"

"That's because you are fucking trash, faggot!"

"I am, I am!"

"Say it, bitch!" He pulled my hair hard and rammed my ass pussy harder.

"Oh FUUUCK! I'm ungh trash unghh! I'm a trash unghh whore, ohhh!"

Then he released my hair and my throat and started pounding my ass hard and fast. He slammed me for a good five minutes before finally, gripping my shoulder in one hand and my hip with the other, he began to groan loudly and convulse as he filled my bowels with his hot cum load.

"Oh god!" I cried out at the amazing feeling of being bred by this stranger.

"Yeah that's right, you love it don't you, whore?"

"Oh yes! I love it so much!"

Then, he pulled his cock out of me causing a glob of semen to plop out onto the floor. He forced me down to my knees and shoved his cock in my face. "Clean me up slut!" I took his cum-covered dick in my mouth and sucked all of the remaining semen off of his meat.

Then, he shoved my face down to the cum on the floor. "Don't you waste my load... Eat!" I greedily licked the sticky spunk from the bathroom floor. "Good job you disgusting sissy faggot." I blushed at the compliment.

After that he released me. I knelt there for a minute as he returned to the bedroom. Then, I got up and wiped my face off a bit. I was looking at my self in the mirror thinking about how amazing the whole experience had been, when I heard him call out to me.

"I need some fucking cigarettes, bitch boi. Get your little dress on and carry your ass down to the convenience store and get me a pack of Camels." I turned to him in surprise with an 'I don't think so' look on my face and saw that he was holding my car keys in his hand. "If you want these back you'll do what I said."

"Wait, you want me to walk to the store for cigarettes?" I protested.

"Only if you want your car back you dumb bitch."

Oh my god, I thought. He's fucking serious. After realizing that I didn't really have a choice, I quickly pulled on my undies and my dress. Then, I slipped on my fuck me pumps and turned to him one last time hoping for some pity, but he wasn't even looking at me. I hurried out of the door.

Thankfully, the convenience store was just about a hundred yards away, across the motel parking lot and up the hill of a vacant lot. It was probably about ten o'clock at night and as I walked across the lot, heels clicking on the pavement and with the moonlight glistening against my wet skin, all I could think of was how I looked so much like a cheap hooker. My dress was so short that I was sure the gentle evening breeze was giving anyone who might be looking a teasing view of my freshly fucked ass and the pink thong nestled between my cheeks. I couldn't believe I was doing this, but I really didn't have a choice.