The Night That Would Never End Pt. 02

Story Info
A sissy gets used at a gas station.
2.1k words
4.68
19.8k
27

Part 2 of the 7 part series

Updated 06/10/2023
Created 07/10/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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

*

Up until now I had never gone out to a public place dressed up as a girl. Sure, I went to adult theaters, truck stops, or parks, but never into a 'normal' space like a convenience store. I was super nervous. It didn't help that this was a rough neighborhood. I just wanted to get his fucking cigarettes and get out of there. As I finally began to approach the store from behind I could feel semen running down my inner thigh. Oh fuck! I thought, hoping no one would notice as it rolled all the way down and collected in my shoe.

As I rounded the corner to the front of the store, I saw several cars at the gas pumps and a couple of people exiting the store. Several of them were staring at me, but I kept my head down in embarrassment and headed inside the store eager to get my task done. Thankfully, there was no line so I went straight to the counter and said, "One pack of Camels, please."

The Middle-Eastern cashier looked at me curiously as he grabbed the pack of smokes from behind him and dropped them on the counter. I quickly fished out the money from my purse and handed it to him when, to my horror, he said, "ID."

Fuck! I thought. I hadn't considered the fact that they would ask to see my ID. I nervously pulled out my driver's license and handed it to him. Of course, in my driver's license picture I look like a man, not like the dolled up sissy standing in front of him. He looked at it, then looked at me with a baffled look on his face. Then, he smiled real big and, in broken English, loudly proclaimed, "Ohhh, you sissy crossdresser?"

I was mortified. There were at least two other people in the store, and I was trying to be discreet, but he just outed me to everyone. Paralyzed, I kept my eyes on the counter in front of me. Of course, at the same time that I was feeling this great horror, I also felt my sissy clit tingling. Did I subconsciously want to be outed? "Y-yes, I..I am." I stammered.

The cashier leaned in a bit and in a much lower volume asked, "You like suck dick, yes?"

Whoa, I thought. That was blunt, but I've always heard that honesty is the best policy, so I answered him, "Uhh, yeah."

"You want suck my dick?" He motioned to the crotch of his pants where there was a visible bulge. All embarrassment aside, I definitely wanted to see what he had under those khakis.

"Sure." I said smiling.

"Nice," He said excitedly. "Come with me."

I followed him as he walked to the end of the counter. It wasn't until we met at the end of the counter that I noticed his name was Ali according to his name tag. Ali was a middle-aged man of average height and build, and he had a neat mustache. Ali called out to another guy who was working there and said something in Arabic. The other guy then chuckled and said something back, eyeing me up and down. I imagine Ali probably said I'm going to take this whore to the back and get my dick sucked, but I don't know.

Ali led me into the back office. It was a small space, with a desk, a few file cabinets and a couple of chairs surrounded by all the typical back office paraphernalia. The man took a seat in the chair that was closest to the door and undid his pants, pulling out a big uncut brown penis. I dropped to my knees and took him in my mouth without a second thought. He placed his big hands on top of my head and guided me as I methodically bobbed up and down on his penis as it grew larger with every stroke of my lips.

Finally, his cock had grown long and thick enough that I was slightly gagging on it. I could tell he was enjoying it and I figured he would be shooting his wad pretty soon, but I was wrong. Instead of cumming, he leaned over me and lifted the hem of my dress, uncovering my beautiful white ass. Then, he gave it a firm smack and began to roughly squeeze my butt cheeks.

"You like butt fuck?" He asked.

"Mmm hmm." I mumbled, mouth full of man meat.

"You let me fuck." He said as he pulled my face off of his lap and stood up. The words felt more like a command than a suggestion, as he shoved his chair out of the way and pushed me over the desk. Then, he pulled my thong down to my knees. I quickly grabbed the lube from my purse and handed it to him. Thankfully, unlike the first guy, Ali used it. He rubbed the lubed up and down his rod and then he grabbed my hips and mounted me.

He wasn't gentle at all, and if he noticed that my hole had already been used, he didn't say anything. He just shoved his meat right into my ass pussy causing me to yelp.

"Aghh!"

Not wanting anyone to hear what was going on, he immediately reached out and placed a hand over my mouth and pulled me back against him saying, "shhhh, you shut up!" Then, as he held me like that, he began to rail my ass as though it was just a flesh light and he needed to get a quick nut.

He fucked me so hard that I could hear the desk scrape across the floor as my hips banged into it. He was grunting and groaning like an animal as he pumped my ass.

"Yes, yes, take my dick! Take my dick!"

"Mmmphh... Mmmphh... Mmmphh," I moaned through his hand as he penetrated me. He only managed to last a couple more minutes.

"Yes! Unghh.. yes, bitch! I am cumming in your ass! Arghhhhhh!"

"MMMPHH, MMMPHH, MMMPHH!"

He drilled his cock deep into my bowels and unleashed a torrent of hot ejaculate into my ass pussy. He shot so much cum inside me that I was pretty sure that this was his first time to cum in a long time. As his powerful orgasm subsided, he leaned us both over the desk and collapsed on top of me.

"Ohhh, thank you, sissy," he said as he heaved for air, waiting for his erection to soften. When he finally pulled his cock out of my gaping hole, cum rolled down my taint and dripped onto the panties stretched between my thighs and onto the floor below. I started to get up but he stopped me, firmly pushing me back on the desk. "Stay." Then, with a smile on his face, he said, "I see if Umar wants your ass too. Don't move, whore."

Oh my god, I thought as he left the office. I really am just a sissy fuck doll. The thought of it made my shriveled clit leak profusely. Here I was bent over a desk in the back office of a shitty convenience store with two loads in my ass and I was about to get another. I stayed there, like a good girl with cum dripping from my ass, patiently waiting for what felt like an eternity. I decided to reach out and grab ahold of the edge of the desk and stick my ass up high while arching my back. That way whoever walked in would have a fantastic view of my goods. Finally, after what felt like an eternity, the door opened and in walked Umar.

"Hi there." I said seductively, raising myself up looking over my shoulder. He looked to be about the same age as Ali, but a bit taller and definitely bigger. He seemed to be built pretty well under his polo shirt and slacks. After he undid his pants, I could see that he also had a much bigger cock than Ali, and he wasn't going to be wasting any time.

Without replying to my greeting he walked up to me, placed his hands in between my shoulder blades and pushed me down on the desk. Then, he started forcing his already hard member into my soggy hole. I tried to hand him the lube but it was too late. I was glad that Ali had lubed me up with his massive load because with one massive hand pinning me to the desk, and a deep grunt, Umar forced all of himself inside me at once.

It was intense! I grabbed the edge of the desk again, gripping so hard I thought I would break it. Then, while I moaned like a defeated whore, he pulled his cock almost entirely out of me and immediately rammed it back in.

"Fuck!" I cried out.

Like Ali, Umar needed me to be silent, but instead of using his hand, Umar pulled his cock out of me and yanked my panties all the way off. Then, he wadded them up and shoved them into my mouth. "Shut up," he said. I could taste my own cum as well as the cum of the other two men leaking out of me. Then, with very hard smack in my ass, he grabbed his throbbing penis and shoved it back in.

"MMMPHH!"

He fucked me hard and deep with more ferocity than anyone ever before. I swear the desk was tilting up on two legs every time he slammed into me, as paperwork and other office items fell to the floor. I pulled on the edge of the desk and kicked with my legs, but there was no getting away from this ass pounding.

Umar was grunting and growling like a rabid animal and making me feel like nothing more than a piece of meat, as he used my hole like it was the dirty gym sock that he beat off into. I was nothing to him. No feelings, no emotions, no pulse, just a warm hole to shove his cock into. And shove he did!

Umar plowed me so intensely that he fucked me right out of my cheap heels. I only realized this because my barefoot landed right in the middle of a small puddle of slippery cum that had been spilling out of me and onto the floor. More accurately, it was being fucked out of me as Umar's cock acted like a plunger. Finally, I gave up the struggle and accepted the inevitable. My legs no longer kicked, they just dangled. My whole body was limp and almost lifeless, as he pummeled me into oblivion. He continued to plow me like this for another ten minutes at least before he finally exploded and launched yet another massive load into my wore out little pussy hole.

He removed his cock and gave my ass two or three very hard smacks (I can't remember exactly how many because I was completely out of it at this point) leaving red hand prints on my bottom. Then, he grabbed a rag from a shelf, wiped himself off, and threw it on the floor by the mess of cum. "Clean mess," he said before walking out. I took my soaked panties out of my mouth and put them back on. Then, I sank down to the floor and began wiping up the semen that had spilled out of me, while more continued to dribble down my legs.

By the time I got it all cleaned up, Ali came in with the pack of cigarettes that I needed and handed them to me. He then directed me to the back door of the office and said, "you leave this way." I collected my purse and lube, quickly slipped my shoes back on, and exited the office on wobbly legs.

"Thank you, whore," Ali said as he waved goodbye.

"Oh, thank you," I waved back with a cute bashful grin.

As I walked across the dark empty lot towards the motel, I felt like I was high. My butt cheeks were slippery from all the cum and they slid against each other causing my dress to collect in between them. Also my foot was sticking to the inside of my shoe because of the cum that I had stepped in. I staggered along on the uneven surface like a girl who had one too many drinks, until I finally reached the asphalt lot again.

Time to deliver the cigarettes.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousover 2 years ago

I need a man to shove my face onto a desk top or bed and fuck me hard. Just fuck me and hurt me with no thought to my sissy clitty. 4yourpleasureiam

AnonymousAnonymousover 2 years ago

I wish I was you!

AnonymousAnonymousover 2 years ago

Looks like you delivered

Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
A Wild Night at the Truck Stop Kristy helps the truckers with their loads!in Transgender & Crossdressers
Shortcut to a Gangbang Sissy Kristy gets a gangbang!in Anal
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Sissy Kristy Gets Her Cherry Popped Kristy is forced to give up her anal cherry.in Transgender & Crossdressers
More Stories