Sissy Stories: Sissy’s Lunch Break Chastity Time

February 1, 2024

In navigating my distinctive journey, I derive fulfillment as a sissy, willingly taking on the submissive role in spontaneous connections with men. Acting as a conduit for their desires, my purpose is to alleviate their tension, enabling them to tackle the challenges of their daily lives. While ideally, their wives and girlfriends should cater to these needs, reality often presents a different scenario.

I willingly step into the shoes of women who may not consistently fulfill these roles, discovering a sense of purpose in the process. However, it leaves me feeling like a mere instrument for their pleasure, embodying the desires of every sissy.

Sissy Random Male Partner

Not too long ago, a guy reached out, expressing his desire for a lunchtime blowjob. Eager to assist, but with my house too far, we agreed to meet in a nearby Walmart parking lot. His truck had dark-tinted windows, and the plan was simple – I’d pleasure him in his truck, allowing him to swiftly return to work. Always ready to swallow a load, I eagerly embraced the opportunity.

Already dolled up for a day of servicing, I wore a plaid skirt, black stockings, boots, and a white floral top. Beneath my thong, a pink cage adorned me, and a red heart-shaped butt plug graced my rear. Quickly heading to the store, I aimed to minimize any extra time he spent away from his lunch break.

Easy to spot in the vast Walmart parking lot, his truck displayed a big Confederate flag on the back glass and a Trump 2024 bumper sticker. Despite a momentary hesitation, I decided cock was cock, and I was craving some cum. Parking on the passenger side of his truck, I climbed into the front seat to fulfill our impromptu encounter.

Chastity Encounters With Burly Men

Having never requested pictures during our chats, I was uncertain about what to expect. Upon opening the truck door, I glanced into the driver’s seat, and there he was – a robust working-class man with sizable biceps and a thick salt-and-pepper beard. My attention then shifted to his crotch, where I noticed his jeans already open, revealing his thick, uncircumcised cock lying there semi-erect, patiently awaiting the attention of a cock-sucking faggot like me.

I swiftly climbed in, shutting the door behind me. A smirk appeared on his face as he, in a deep, manly voice, gestured towards his penis, saying, “There it is. Start sucking.”

Passion in the Truck

Eager not to waste any time, I decided to indulge in the taste of his cock. I swiftly pulled up the center console, knelt in the passenger seat, and leaned into his lap. Grasping his heavy member, I guided it into my mouth. A deep sigh escaped him as my warm lips enveloped his eager cock head. Reveling in his sweat-soaked taste and the distinct musk of a working man, I skillfully worked his cock.

His penis swiftly became rock hard, throbbing within my mouth. Initially, he sat back, enjoying himself, moaning intermittently. After a few minutes, I felt him lift my skirt, his rough hands fondling my ass cheeks. His touch grazed the butt plug in my asshole. Leaning over to inspect it, he inquired, “you got a plug up your ass?”

“Mmm hmm,” I replied, continuing to suck his dick.

“You’re a real fuckin slut, huh?”

That’s when I popped his cock out of my mouth and declared, “you have no idea!” Giggling, I attempted to deep-throat his member. Though I only made it about two-thirds of the way down before gagging, he didn’t seem to mind. Placing his hand on my head, he thrust his hips, enjoying my efforts while continuing to play with my ass. As I moaned on his cock, he suddenly exclaimed, “fuck work. I need some of that ass.” I began to lift my head, but he firmly kept his hand on top of my head, pressing me onto his shaft.

A Sissy's Unexpected Twist

Suddenly, the man declared, “Fuck work. I need some of that ass.” As I began to lift my head, he firmly kept his hand on the top of my head, holding me down on his cock.

“Keep sucking. My house is close by. I’m going to drive us there and fuck you real quick.” With my mouth full, I mumbled my consent from his lap. The drive was fast, filled with turns, and my mouth busy, leaving me clueless about our destination. He instructed me to keep my ass in the air, occasionally smacking my bare cheeks hard, which I thoroughly enjoyed.

In what felt like a short drive, we arrived at a garage. Clicking the garage door button, darkness engulfed us. “We’re here,” he finally said. I sat up, wiping my mouth, as he quickly exited the truck. Stepping out on the passenger side, I surveyed the surroundings—his large garage cluttered with tools and boxes, a typical setup. I anticipated being led to a bedroom, but he had different plans.

Pointing at a small metal desk against the wall, he commanded, “Bend over that desk and drop your panties.” Stammering out an ‘okay,’ I followed his instructions, lifting my skirt, dropping my panties to my ankles, and bending over the cold metal surface. Locked inside his cold, dark garage, I felt vulnerable, completely at his mercy. The situation aroused me to the point where I could feel cum leaking out of my chastity cage. As he moved up behind me, I handed him some lube from my purse.

Fierce Chastity in the Garage

“Pull that plug out of your ass,” he demanded, taking the lube from me.

I slowly removed the plug from my pretty pink hole, holding it in my hand. The sound of him greasing up his shaft filled the air. Placing the lube on the desk, he started spanking my ass with his cock—FAP FAP FAP!

“Ready for this?” he asked.

“Y-yes,” I stuttered.

“Good, because it’ll have to be quick.” He aimed his cock head at my slightly gaping hole and forcefully penetrated me.

“Gaghh! Fuuck!” I cried out as his cock slid deep inside me with the first thrust. I wasn’t fully prepared for his thick member, causing pain.

“Sorry. I’ll be fast.” The stranger grabbed my hips and began pounding away at my poor little hole.

I moaned and groaned, crying out, “Fuuuck! Oh my God! Unghh AGHHH!”

He relentlessly slammed his cock into my ass. Attempting to crawl away from the onslaught, my cheap boots found no traction on the slick garage floor, leaving my legs flailing helplessly. Realizing I couldn’t escape, I resigned myself to endure the ass pounding.

The stranger, a hefty man weighing around 230 pounds, utilized every pound of his mass to thrust as deep as possible with each motion. The tops of my thighs repeatedly collided with the edge of the desk, ensuring sizable bruises tomorrow. He grunted like a wild beast, indifferent to the piece of flesh he was using—I was just meat to him.

Short Sissy Chastity Lunch Break

Suddenly, I heard his phone ringing.

“Ahhh shit!” Clearly displeased with the interruption, the stranger reached for his phone. “It’s my boss, I gotta take it. You be quiet.”

“O-okay.” I was just relieved to get a break from the intense experience.

The stranger answered his phone, and it seemed his boss was inquiring about his whereabouts. Apparently, he had overstayed his lunch break, but he appeared unconcerned. Crafting a feeble excuse, he continued slowly thrusting his fat dick in and out of my ass. I whimpered softly, using the butt plug as a makeshift gag. He must have noticed because he intensified his thrusts while deceiving his boss.

“I shouldn’t be too much longer. See ya soon.” Then, he tossed his phone onto the desk. “Enough playing around, I need to cum.”

Playing around? Was he just ‘playing around’ this entire time? Seizing both of my hips again, he began fucking me as if he loathed me—seriously assaulting my ass with his cock. Grunting and groaning, he pounded into my helpless little fuck hole like a frenzied monster. Fortunately, my ass had become somewhat accustomed to his penis by this point, but the intensity was still overwhelming. He relentlessly pounded me with such force and passion that my head bumped into the wall in front of me.

Fulfillment and Departure

Finally, he got what he wanted. He slammed into me, penetrating deeply one final time, and with that thrust, he lifted me from the desk onto my tiptoes. Then, with a deep guttural groan, he seeded my sissy pussy. His cock throbbed and twitched inside of me, releasing shot after shot of hot semen into my guts. He quivered and shook through his orgasm, which felt incredible on my end. I’m guessing he hadn’t ejaculated in a long time because he came so much!

As soon as his orgasm dissipated and his head cleared, he yanked his cock out of my used-up ass and said, “Alright, get your shit. Let’s go.”

Then, he grabbed some paper towels from a spool on the wall and quickly wiped himself clean while I swiftly reinserted the butt plug, trapping his seed inside me, and pulled up my panties. He didn’t utter another word; he just zipped up and hopped into the truck. I did the same. Before I knew it, we were speeding down the road back to Walmart.

Self-Liberation After Parting

On the way back, he expressed that I possessed the best pussy he’d ever experienced, emphasizing my prowess in handling a cock. His compliments left me beaming with satisfaction. Upon reaching the parking lot where my car was, he mentioned the likelihood of using my holes again soon. Eagerly, I assured him of my availability anytime, sharing my phone number.

Upon arriving home, I promptly removed the plug from my ass and placed it in my mouth, relishing the taste of his cum. Subsequently, I indulged in self-pleasure, finger-fucking my asshole and occasionally sucking his creamy load off my fingers. Eventually, I introduced a dildo into the mix, sliding it into my bussy. As I bounced on it, a vibrator against my chastity cage added to the sensations, allowing me to vividly replay the brief encounter in my mind. Before long, I climaxed intensely, shooting my own sissy juice across the expanse of my bed.

I sincerely hope to hear from him again soon.

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