Brittany's First Time Out

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

"Ready?" he asked. I nodded. I'd never been more ready for anything. My heart fluttered as I felt the tip of his cock teasing my slutty hole. My arms turned to jelly as he began to enter me. My asshole devoured the tip of his cock and wanted more. It seemed he could tell by my girlish squeaks and my trembling how badly I needed more so he stopped there and proceeded to torturously fuck me with the tip of his cock.

"More! Please, more! I'm begging you!" I moaned desperately.

"More? More what?" He asked, being deliberately aloof.

"More cock! Please, I need more cock!" I yelled in a breathy tone.

"Aren't you a slutty little sissy bitch, begging for my cock. Tell me how much of a whore you are, and maybe I'll give you what you want" He demanded.

"I'm a sissy cock-whore! I'm a slut for your cock! I'm such a slutty whore! I need your cock!" I cried, blushing furiously. He seemed to be satisfied with my answer as he began to ram his thick slippery cock deep inside me and fuck my sissy brains out.

I was no longer in control of the sounds erupting from my cherry red lips. Each thrust seemed to force out a cacophony of girly moans and squeaks. My caged cock began to leak heavily. My arms collapsed and left me lying with my cheek caressing the cold metal of the car. I had lost all sense of manhood. I'd cast aside all ideas of dignity. All I was at that moment was what I'd just announced to the world. I was nothing more than a dirty sissy cock-whore who was getting exactly what she wanted most.

I was in ecstasy the entire time my asshole was being ravaged by the officer's thick cock. His firm calloused hands were all over my body. One kept a hold on my waist while one gripped my fake breast. One would grab hold of my cock cage while the other smacked my ass. His intense fucking didn't let up for a second, nor did my feminine squeals of pleasure.

I felt like I was on the brink of passing out when he finally asked me: "Do you want me to cum in your ass or your mouth?" My mind was in no shape to answer questions.

"Aaahhh...uhh...mmm" was all I managed to get out between thrusts. He gave my ass a hard smack and started to laugh.

"You cock-drunk slut! You can't even form words while you're getting fucked!" He exclaimed. I could only blush in response. "I'll tell you what. I'll fill your sissy ass with cum, and make you clean my cock with your mouth." He explained. I answered with an ecstatic nod. I couldn't wait. I could taste it already.

He leaned his body into me, grabbed hold of my fake titties and held me close. Once he had me firmly pressed against his toned abs and chest, he took a deep breath and started ramming my hungry asshole as fast and as hard as he could. My eyes went wide, and I squealed in pleasure. He fucked me even faster and harder until finally, he wrapped his arms around me and buried his face into my neck. One final thrust caused his breath to hitch and a groan to escape his lips. I felt his cock swell and explode, filling my ass to the brim with hot cum. We both let out exasperated sighs.

"Mm...Damn, that was hot" he sighed as he pulled his cock from the pool of cum in my ass. Without a word, I quickly knelt in front of him and looked up like a dog expecting a treat. He chuckled a bit and brought his dripping cock to my lips. I immediately took it into my mouth and started licking it clean. The taste was overwhelming. The musk of his cock and my ass mixed together with the strong salty flavor of his cum. I sucked every inch of his head and shaft dry and licked up anything left on his balls and thighs. I couldn't get enough. I leaned forward for another taste, but he placed his hand on my forehead.

"I think this sissy has had enough cum for tonight" he said as he stroked the top of my head. I pouted like a spoiled princess in return.

"Aww, cheer up. I've got a feeling it won't be too long before you're back on your knees again" he reassured me with a knowing tone. He stuffed his cock back into his pants and zipped himself up. I looked down to find my panties around my ankles. I stood up, slid them back up my legs and brushed the dirt off my white stockings. As I was inspecting my satin covered legs for any stains, I heard the door of the police cruiser shut and the engine start up. My head whipped upward to find the cruiser slowly backing away. I rushed over to the side of the car to at least say goodbye to the officer. He looked over at me through the closed window and blew me a kiss as his car began to speed away into the distance. I blushed as I stood there in the now empty parking lot with the sun beginning to reveal itself over the horizon.

I had to get back home before too many people were out and about. I couldn't have my neighbors witnessing my sissy walk of shame. I seated myself back onto the leather seat of my civic. I could feel the sticky cum oozing from my ass into my frilly white thong. I looked over to find the contents of my purse spilled out in the passenger's seat as well as the plug I'd been carrying in my ass. The officer must have stashed the plug in here as he retrieved the lube.

As I started up my car, Ariana Grande greeted me through my speakers with the chorus of "Side to Side." I smirked at the coincidence and began to make my way home. The drive was fairly uneventful. I passed some cars getting a head start on the morning commute, but no one paid me any attention. I arrived back at my house and scanned the surrounding street to ensure the coast was clear.

I stepped out of my car and teetered to the door as fast as my exhausted legs could take me. It wasn't until then I'd realized how completely drained of energy I was. As soon as my front door was closed and locked, I trudged to my bedroom. It took all that I had to kick off my heels and slide out of my dress before I collapsed onto my bed. Sleep took hold of me as I lay there in my makeup and frilly undies.

That night, I'd shed all my preconceived notions and discovered a side of myself that was hidden away for who knows how long. I wasn't sure if I was ready to embrace the cock hungry slut inside me. She was still a little frightening, but I knew she was there. From then on, she'd always be there, just waiting for another chance to come out and play.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
4Leather4Leather3 months ago

CD sissy could only dream of this happing.

Loved it

AnonymousAnonymousover 3 years ago
Shivers and extensive excitement in my prostate

When you read the content make you feel you are in the story. Loved...wants to read more from you

BrendaNWBrendaNWover 4 years ago
so hot

So well written I couldn't stop reading .. I remember my first times out of my home driving and slowly doing more and more .. so scary but so exciting also .. Tiffany

cali_fraecali_fraeover 4 years ago

Really enjoyed your story. I'll go out on a limb & say a lot of your readers have either been in a situation like this or want to take that 1st step into the world as a sissy & thats what youve captured really well, the fear, hesitation, desire, denial & realisation of that 1st time where something changes inside. I hope you'll continue writing & putting stories on here x

AnonymousAnonymousover 4 years ago
Jealous

As a sissy CD I dream of this.

Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
More Stories