Sissy's Long Night

~It was a long night from the start.

The freeway lights ticked by as I drove, barely focused on the road. All the space I'm my brain occupied with the feeling of my wet ass, butt plug inside. Every throb of my crotch increasing the pressure of my thong pulling against the rim of the plug. I almost missed my exit, since a bump almost caused an orgasm.

At the time, I was probably 22 or maybe 23. Long dark brown hair, down to the middle of my pale freckled back. Five foot, seven; thin but fit. Barrel chested and very wide hipped... but, most importantly, a very nice, smooth ass.

Phoenix, Arizona is a shitshow in the right places at any given time of day. But it's the kind of shitshow that you pay good money to experience, delivered on a silver platter... if you know where to look, or who to ask. Growing up here, it took me about 14 or 15 years to actually see SOME of the seedy underbelly in my town. Not long after that, I did everything I could to find my happy place there.

So... trust me. Working up to going to one of the sleazy sex shops, with gloryholes and a theater... not a big deal.

I had spent all afternoon fully utilizing my bathroom; cleaning myself out, shaving, moisturizing my skin, smelling nice, blow-drying my dark brown, shoulder length hair, put on light makeup and trying to pick out clothes (and trying desperately not to masturbate). Finally after what felt like an eternity, I stood naked in the mirror and looked at my body... my face~ I felt more feminine and sexual each time I dressed myself up, but this was much different.

This time it was so natural, it almost felt deliberate.

My instincts were driving me every step of the way. I knew how long it would take to become as feminine as I was capable of being, naked... Let alone actually choose an outfit and dress up.

I had finally settled on my favorite tan sheers attached to a Victoria's Secret white lace garter belt and matching VS thong. I am definitely a little barrel chested so I need to have a corset if I'm ever going to look feminine. Thankfully I have a nice white lacy one. It's not a brand match for the garter belt but it's close enough on the white. I put a couple little jingly bracelets and a white cloth choker with a little bell sewn on in a little white clutch. I even put a lil white bow in my hair...

I saw my favorite butt plug, sitting on top of some clothes and I thought about wearing it out... unable to decide, I flipped a coin. Heads I don't wear it, tails I do. I flipped tails! So I followed through, squirting a bit of lube in me before I slid the plug inside my slippery hole. After I wiped the excess lube away, I looked in the mirror again. I was so sexy. Yeah I looked like a slut, but I really looked like a girl. The makeup, the hair, even my chest in the tight corset. I was a HOT girl.

By the time I was ready with my outfit on, underneath my street clothes... it was almost 8pm.

I also mostly definitely spent some (a lot) time psyching myself out and then watching sissy hypno videos to get my sex drive focused on driving out to a local sex shop and trying to engage in some very slutty behavior...

So I finally did.

The outfit I was wearing along with my baggy street clothes, was far too snug in the crotch to drive comfortably... so all I had on my mind was getting into that tight skirt that shows off my garter belt.

Mostly so I can get inside the building where the gloryhole booths are, but also... so I can get some attention from the men on the way through the shop and theater, where they're at. I figured I would have at maybe one or two dudes try to see where I was heading once inside, I very much underestimated my appearance or the appetite of the men there...

I made the horny impulse decision to get out of my street clothes in the parking lot. While I had my pants down before I put my skirt on, some guy yelled across the parking lot. "Nice ass!"

I turned around fast, it was dark and I couldn't even see my admirer. My cock tucked in the very small thong I had on over my garter, poked out because I had turned around very suddenly.

A dark car between a car and a brick wall across from where I was parked, flashed its lights

"Cute lil cock too! I bet you're ready to swallow cum tonight!"

"Come over here then!" Said a distinctly different voice from that direction.

I turned around to grab my lil bag... then slowly put my skirt on, then rolled and tied the bottom of my t shirt and I nervously started walking over to the car.

As I was walking over, smiling... the unknown men were all talking excitedly to each other and when I got to the car there were three men looking at my body inside, in a nice sedan watching porn on a tablet jerking off. I leaned in and looked at the porn they were watching... it was a brunette tgirl in white lingerie getting seriously gangbanged by a lot of guys...

More importantly it was a tgirl that looked very similar to me...

...but I had stared too long at the porn, the man in the back seat reached out the back window and ran his hand up my thigh. I spooked a little bit but I stood up and looked in the back. While he had his his one hand on my thigh, he was still squeezing his thick cock... seeing this made me more horny than apprehensive, and I leaned my ass closer to the window he was practically leaning out of... once he got his hand up my skirt and grabbed my ass, I leaned over to the open window in the front and whispered to the driver, "Do you think I look like her?" He began turning around and I didn't wait until he looked to take my baggy t-shirt off, exposing my white corset. Backseat man had my skirt pushed up around the side as my shirt cleared my face, and the driver looked at me like a kid looks at ice cream. "Yeah, actually!" He said enthusiastically. He was hot, in his mid to late 30s and also had his rather large dick in hand.

I smiled seductively.

"Why don't we all go inside and make a cover album of this porn right here?" I said, grinning at my own cheesiness. Backseat man slipped a finger in me and kissed my ass cheek, causing me to moan into the front window. I turned back to him and giggled then said, "I don't wanna turn into a whore in this parking lot."

He loudly slapped my ass and said, "get in the damn car then, slut."

I thought to myself, this is what I wanted...

And opened the door holding my shirt and my clutch.

Backseat man grabbed my arm and dragged me over his lap a little aggressively. I landed with an oof, ass exposed right behind the center console.

Driver turned around and grabbed a handful of my ass and said. "Why would you want to go in there, when we know a much better place?"

"As long as I get home safe, we can go wherever you want." I practically moaned back

The passenger finally spoke, "Oh we'll get ya back safe. Safe and full of cum!" He laughed. I laughed and said, "I hope so!"

The other men laughed at my enthusiasm.

The driver was already backing out and I kinda loved the idea that I wasn't going to have sex in a dingy sex shop but I definitely had my questions about these men who were driving me somewhere all horny and compromised.

"So what's everyone's names? I'm Devin!" I said.

"Jeremy." Said the driver.

"Allen." Said the man who had me comfortably bent over his lap with his fingers inside me.

"Ryan, but think you're going to forget our names."

The guys all laughed.

I said in a playful tone, "I won't forget unless you drug me... you're not going drug me, at you?"

"No, but there are going to be a lot of names to remember." Said Ryan.

I started to get excited about the near future. I felt wary. Still, the way they joked about it all... but kinda still told me what was happening kept the suspense up.

As I was pondering my inevitable experience, Allen slowly started playing with the butt plug inside me.

I moaned and didn't fight back. Turning to look at him he was picking my waist up at the same time, so I assisted awkwardly and he moved his cock out from under my garter where it was probably squished uncomfortably.

"Oooh I'm sorry babe!" I said putting my hand over my mouth.

"You wanna kiss it better?" Allen said.

I quickly positioned myself behind the driver curled up on the floor and Allen slid up into the corner and shook his, now flaccid cock at me. Attempting to be silly, I slid over and kissed it once on the tip and laughed as I said, "There! All better!"

Allen was not amused.

He grabbed my smiling face by the hair and dragged my head over to his crotch. Then he yanked my head forward and back next to his cock and forced himself into my mouth as I was whining.

Once he was in my throat, Allen grunted out "I'm done playing, bitch. You're going to swallow at least one load before we're there!" Then, as he let go of my hair. Ryan pushed my head down keeping it in place for Allen to start roughly fucking my throat, his cock started getting thicker and hard. Very hard.

It didn't take too long for Allen to cum inside my throat. He pushed all the way into my throat and groaned loudly. I felt the thick, warm cum coat the inside of my throat and mouth. There was so much cum that I gagged with his thick cock deep in my throat. He groaned again and let more cum out as he dragged his cock out of my mouth with a pop and a cough.

The slut in me was completely awoken and I eagerly slurped the excess cum and saliva off of Allen's cock and balls. While he was a little bit too rough for my liking, I felt so wanted... so sexy. The feeling drove me wild.

After a little bit of work, cleaning up after my throat fucking... Allen was getting hard again.

Satisfied with how hard Allen had become, I climbed up onto the backseat. I got on my knees and pointed my ass at Allen's lap. He wasted no time, slid my panties over and roughly pulled out my plug. I moaned a bit. Immediately, Allen shoved his tongue into my wet ass, sliding it in and out; sucking on my hole and letting it pop out loudly. This aggressive oral technique made me tingle and moan uncontrollably. I could focus on nothing else, until he suddenly stopped. For a second or two my mind swam and I felt almost dizzy with pleasure. Then, Allen pushed his cock inside me all at once.

I gasped, then yelped, "Aaahh!"

With his thick cock all the way inside my ass, Allen grabbed my throat and pushed even harder and whispered in my ear, "You're getting fucked so hard tonight, and you're gonna love every minute of it. You little whore." Allen pushed my face down into the seat and began pumping his thick cock in and out of my eager hole. Completely unaware that we had arrived, the lights outside the car got brighter. I barely noticed, and definitely didn't care. Allen was definitely rough but I was loving it... moaning and pushing back with every thrust. I must have been cock drunk, because not only had we arrived in a bright parking bay. We had pulled in to a bright parking bay with a makeshift sex club in the same room.

The door next to my face opened and I looked up at Jeremy. Naked, cock in my face, three or four naked men behind him.

Allen kept fucking my ass but pushed down on the small of my back with one hand, and yanked my hair. This put my face in the perfect place for Jeremy to shove his long cock into my mouth. I instinctively pushed my tongue out and opened my throat best I could. Jeremy slowly slid half his cock in and out of my open mouth, stopping every time he entered my throat.

As I was looking up at him, as sweetly as I could manage with Allen roughly fucking my ass. Jeremy smiled and said, "Guys! The whore is already loving this!"

There was some distant laughter and Allen pushed deep into me and pushed my head down on Jeremy's cock, forcing it down my throat. Completely stuffed with cock, I was in bliss.

Jeremy and Allen moaned. I slid my tongue up against Jeremy's cock, then all over his balls as he moaned I felt his balls tighten and he shot streams of warm cum straight into my tummy. Allen also leaked another load into my twitching hole.

Allen slapped my ass, and pulled his cock out of me. I felt wetness running down my balls and soaking my panties. Allen laughed and pushed my plug back into my loosened ass, slid my panties back and fixed my skirt.

"Get out and come please us, it's your job whore." Allen said, shutting the door on his side. Jeremy was still wiping his wet cock on my face, smearing my makeup.

Jeremy grabbed my hair, bent over and looked into my eyes. "We're not going to hurt you, if you want to stop." He pulled on my hair, walking me out of the backseat on my hands and knees.

There was a cheer and some laughter. A group of probably 12-13 naked men all roughly the same age but wide variety of build. Some fit, some a little fat. All with pretty large cocks.

The realization that I am to be a plaything for all of these hairy sweaty men, finally set in. I was so excited.

Jeremy let me by my hair onto a soft carpet rug in the middle of a sectional couch where the men were seated and let go of my hair. Once he let go, I fixed my hair, and straightened my corset. I looked at the men who were eyeing me up in the most sexual way. I began to flaunt my body, sitting on my knees I began to pull my panties off. Sliding down on my chest as I did. I ended with my ass up face in the carpet. "Wow." Said one of the men.

"Whore is fuckin tight too." Said Allen.

I put my hands down and brought my face back up to cock level and began to crawl towards where I thought the wow came from. There were three men all slowly jerking themselves on the couch. I crawled over, sat on my knees, opened my mouth and stuck my tongue out.

"You are doing all the work here, bitch." One man said.

With my task ahead of me, I put my face in between a pair of legs. The man continued to jerk off as I ran my nails up his thighs I lowered my head and licked his balls. He let go of his cock and I circled my tongue around the base and slid up to his head, then pushed the length into my throat slowly. He let out a deep moan as I started sloppily throating him. Then he said, "Shit, this bitch is hungry for cum!"

I pushed my tongue against his cock as I slid the cock out of my mouth, the head popped on the way out and I gasped for air. "Yes, sir! I want your cum please!" I said between breaths. Then I slid between two of the men on the couch and pointed my ass at the man who was just in my throat. While he was squeezing my ass and playing with the plug inside me. I started licking and kissing my way up the other mans thighs towards his large balls.

The thought occurred to me, it's going to be a very long night.

(to be continued)