Chapter 5

The dominant gang leader escorted us into a dimly lit chamber, where an opulent four-poster bed stood proudly at the center, draped in velvety fabrics that whispered of the decadent acts that had transpired within its embrace. His commanding presence filled the room as he ordered me to perform an intimate and degrading task upon Lizzy, a voluptuous beauty whose eyes gleamed with a mix of fear and excitement.

As he spoke, he began to disrobe, revealing a manhood that was not only thick and formidable but stretched out far beyond the length of my own, which hung there pathetically in comparison. The sight of his monstrous cock made me gasp, and he smirked, using the leather leash to jerk me away from my focus on Lizzy. “You see, Sissy,” he jeered, “this is what true masculinity looks like. That sorry excuse for a dickling between your legs is nothing but a useless sissy pussy.”

With a cruel twist of humour, he pointed at my crotch and inquired about the “sloppy” appendage that hung there. “What is this?” he taunted. “It’s my ... my sissy pussy, sir,” I responded, my voice trembling with a mix of fear and awe.

He chuckled darkly. “Can sissies like you cum?”

My mind racing, I managed to reply, “I ... I believe so, sir, when ... when given permission.”

His smile grew wicked. “Ah, yes, a good sissy knows to ask for permission. Did you cum without asking, you naughty slut?”

I nodded, ashamed and quivering. “Don’t worry, I’ll overlook it this once,” he said, patting my cheek. “But next time, you’ll be punished severely.”

“Thank you, sir,” I whimpered.

“Now, tell me,” he continued, stroking his cock thoughtfully, “where does one fuck a sissy?”

My face flushed scarlet as I murmured, “My ... my ass, sir.”

He tapped his chin. “Hmm, that’s not quite right. Sissies like you don’t have asses. You have ... what?”

“My ... my cunt, sir,” I corrected, feeling a thrill of humiliation as I said the words.

“Ah, yes,” he purred, “when you’re penetrated in your sissy cunt, you may experience a sissygasm.”

He then announced that he would be the one to claim my anal virginity, a thought that filled me with a strange mix of dread and anticipation. He positioned me on my back, and Lizzy was placed back on top of my face, her scent intoxicating as I eagerly lapped at her pussy. The leader, meanwhile, took his massive cock and plunged it into her, her moans and the slap of their flesh filling the room.

I watched as he ravaged her, feeling the wetness on my face grow from her pussy juices mixing with his pre-cum. I was desperate to please him, to be a good little sissy, and so I licked and sucked as he had instructed. The leader’s stamina was unmatched, and he fucked her with a ferocity that had me drooling with envy.

Finally, after what felt like an eternity of pleasure, he pulled out of her, his cock glistening with their combined fluids. He slapped it against my hair and said, “Now, Sissy, show me you can be a good boy. Get all my cum from her pussy into your mouth, but don’t swallow until I tell you to.”

I eagerly obeyed, my tongue diving into her, savouring the taste of his seed and her essence. As I worked, he took photos, capturing my debasement for posterity. When I had gathered every last drop, I held up my face, my mouth full of his potent cum.

“Swallow,” he ordered, and I did, the taste surprisingly delicious. “I knew you’d make a fine sissy,” he said, stroking my cheek with a smug satisfaction. “Black cock is the best, and you’ll have plenty of it from my boys.”

Before allowing us to retreat for the night, he decided to initiate my sissy training in earnest. “Face down, ass up,” he barked, and I complied, feeling the cold, hard tip of an anal plug pressing against my untouched entrance. He spat a glob of saliva onto it, the only lubrication he deemed suitable for a worthless faggot like me.

With a sadistic grin, he began to push the plug into me, the sensation overwhelming and painful, yet I couldn’t help but feel a twisted excitement as my body stretched to accommodate the intrusion. Lizzy watched with wide eyes, a silent witness to my degradation.

Once the plug was fully seated, he tapped the pink crystal base. “Your cunt training starts now,” he said with a sneer.

We were then directed into a cage, our bodies spent and trembling. As we curled up together, I felt the plug inside me, a constant reminder of my new role as his sissy plaything.

The following morning, I awoke with an intense ache resonating from my rear end, the reminder of the plug’s relentless presence throughout the night making it almost unbearable to move. With a sense of urgency, I managed to crawl towards the washroom, the weight of the object in my anus a constant reminder of my newfound subservience. Lizzy, my sadistic instructor, took great care in guiding me to the bathroom, where she meticulously extracted the plug from my stretched and sore opening, allowing me a brief moment of relief before instructing me to cleanse both internally and externally.

Over the next few weeks, my transformation into a sissy grew more pronounced. My days were filled with worship and service to the gang members’ towering, dominant cocks. I became a skilled practitioner of oral pleasure, eager to satisfy each and every one of them with my mouth. As the days turned into weeks, my mediocre skills evolved into an art form, my tongue dancing and swirling around their thick, veiny shafts with a passion and enthusiasm that surprised even me.