The basement club was a dimly lit dungeon of anticipation, the air thick with the scent of leather, lube, and vodka as Crissy’s party kicked into high gear. The stage was set—a raised platform in the center, rigged with cuffs hanging from chains, a padded bench, and a spotlight that made my skin prickle under the slutty schoolgirl outfit Jan had forced me into. The plaid skirt barely covered my arse, the crotchless red panties left my cock and balls dangling, and the thigh-high stockings rubbed with every step, the pigtail wig bouncing as I moved. The black leather collar around my neck, etched with “Princess’s Sissy,” felt like a brand, and Jan’s smirk from the crowd told me I was exactly where she wanted me. Dick was beside me, his cheerleader outfit—pink skirt, ruffled petticoats, and pom-poms—making him look just as ridiculous, his cock already twitching under his matching panties. Crissy’s “sissy competition” was the main event, and the crowd of twelve—kinky fuckers like Tara, Lee, and their mates—watched with hungry eyes, drinks in hand, ready to see us humiliate ourselves for their amusement.
Crissy, in her latex catsuit, strutted onto the stage, a wireless mic in hand, her grin sharp as a whip. “Alright, you filthy lot,” she said, her voice booming through the club. “Welcome to the Sissy Showdown! Our two sluts—Jan’s sissy and my Richard—are gonna compete to prove who’s the best fucking sissy. You’re the judges, and you’ll score them on how well they take it, beg for it, and make you hard or wet. Winner gets a special treat; loser gets… well, you’ll see.” The crowd cheered, a mix of laughter and crude shouts, Tara already filming on her phone, Lee’s leather trousers tight around his obvious hard-on.
Jan stood beside Crissy, her black corset dress hugging her curves, her Princess vibe in full force. She grabbed my pigtails, tugging just enough to make me gasp. “My sissy’s gonna make me proud, aren’t you?” she said, loud enough for the crowd to hear. “Yes, Princess,” I muttered, my cock twitching despite the nerves, the collar tight as I swallowed. Dick, beside me, mumbled, “Yes, Miss,” to Crissy, his pom-poms shaking as he shifted, his face flushed under his makeup.
Crissy laid out the rules, her voice dripping with mischief. “Three rounds, each testing our sissies’ skills. Round one: toy endurance. Round two: oral service. Round three: the fuck-off, where they take whatever we give them. You lot score each round out of ten, based on moans, obedience, and how much you want to fuck them. Highest total wins. Ready, sissies?”
“Yes, Princess,” I said, my voice shaky, the crowd’s eyes burning into me. Dick echoed, “Yes, Miss,” and Crissy clapped, signaling the start.
Round One: Toy Endurance
Jan and Crissy grabbed toys from the black velvet bag, now infamous for its endless supply of depravity. Jan held up a thick, vibrating butt plug, its buzz loud as she lubed it, smirking at me. Crissy chose a curved prostate massager for Dick, its sleek design promising trouble. “On all fours, sissies,” Crissy ordered, and we dropped, my skirt riding up, my cock swinging free as the crowd hooted. Jan knelt behind me, teasing my hole with the plug’s tip, the cold lube making me flinch. “Beg for it, sissy,” she said, her voice pure Princess.
“Please, Princess, fuck my arse,” I begged, loud and desperate, my cock leaking precum onto the stage. She pushed it in, slow and deliberate, the stretch intense, the vibrations hitting my prostate like a fucking hammer. I moaned, loud and raw, my body rocking as the crowd cheered, Tara shouting, “That’s it, sissy, take it!” Dick, beside me, was whimpering, Crissy working the massager deep, his “Thank you, Miss” chants mixing with his gasps, his pom-poms twitching as he squirmed.
The challenge was to last five minutes without cumming, the toys buzzing relentlessly. Jan leaned close, whispering, “Don’t you dare cum, sissy, or you’ll disappoint your Princess.” Her hand brushed my cock, teasing, making it fucking impossible to focus. I groaned, my moans echoing, the crowd scoring us with raised cards—eights and nines for me, sevens for Dick, who was struggling, his cock dripping more than mine. I held on, barely, the plug’s buzz driving me to the edge, my body trembling as the timer buzzed. Jan pulled it out, kissing my neck. “Good sissy,” she said, while Crissy patted Dick’s wig, his score lower but his effort noted by the crowd’s claps.
Round Two: Oral Service
Crissy announced the next round, her grin wicked. “Time to test their mouths. Sissies, you’re servicing the crowd. Make them cum, and make it quick.” Jan pushed me toward Lee, who’d unzipped his leather trousers, his thick cock already hard. “Suck him, sissy,” she ordered, and I dropped to my knees, the pigtails bouncing, the collar tight as I took him in, my lips stretching around his shaft. The taste was musky, his groans loud as I sucked, my tongue swirling, Jan’s hand on my neck guiding me deeper. “Good sissy, make him cum for Princess,” she said, her voice sharp.
Dick was working Tara, her leather skirt hiked up, his face buried in her cunt, her moans high-pitched as she gripped his wig. The crowd scored us on technique—my deep-throating earned nines, Dick’s eager licking got eights. Lee tensed, grunting, and came in my mouth, hot and thick, the taste overwhelming as I swallowed, Jan stroking my cock through the panties, whispering, “That’s my sissy.” Tara came on Dick’s face, her juices glistening, and the crowd roared, cards flashing high scores for both of us, my lead holding.
Round Three: The Fuck-Off
Crissy’s voice boomed for the final round. “The fuck-off! Our sissies take whatever we give them, and you decide who’s the ultimate slut.” Jan and Crissy strapped on dildos—Jan’s a thick, black one, Crissy’s longer and curved. Lee and another guy, Mark, stepped up, their cocks out, ready to join. “Sissies, bend over the bench,” Crissy ordered, and we obeyed, my skirt flipped up, Dick’s petticoats bunched, our arses exposed to the crowd’s cheers.
Jan lubed her strap-on, slamming it into me, the stretch raw and deep, my moans loud as she fucked me, her voice taunting, “Take it, sissy, show them you’re Princess’s slut.” Lee took Dick, his real cock thrusting hard, Dick’s “Thank you, Miss” turning to gasps. The crowd scored our reactions—my desperate moans and begging earned tens, Dick’s quieter whimpers got eights. Jan pulled out, letting Mark take over, his cock real and thick, filling me as I groaned, my cock leaking, the collar digging in as I called, “Yes, Princess!” Dick got Crissy’s strap-on next, his moans louder now, but my lead held.
The round ended with us both leaking, no cumming allowed. The crowd’s final scores flashed—me at 27, Dick at 23. Crissy declared me the winner, the crowd cheering as Jan pulled me up, kissing me hard. “My perfect sissy,” she said, her voice proud. My “reward” was to suck Lee again, his second load hitting my throat as the crowd clapped. Dick, the loser, was spanked by Crissy in the punishment corner, his arse red as he thanked her.
The night wound down, the crowd’s energy softening, drinks refilled as Jan held me close, the schoolgirl skirt still on, my cock limp but content. “You made Princess proud, sissy,” she whispered, her tone gentle now, the collar a soft weight. Crissy joined us, Dick trailing, his cheerleader outfit a mess. “Next party, we’re adding more sissies,” she said, her grin promising trouble. “You up for it, Jan’s sissy?”
“Yes, Princess,” I said, my eyes on Jan, her nod telling me we were far from done. The night ended with quiet laughs, but the door to more—wilder, filthier games—was wide open, Crissy’s plans already brewing for the next sissy showdown. |