The Town Sissy Pt. 02

"Poor sissy," Mayor Sophia tutted, pouting at the frustrated little slut before her, "left denied all night while she handed out orgasm after orgasm." Officer Caitlyn giggled, seeing the state I was in, her fingers rubbing the underside of my balls. I moaned loudly as another hand gripped my throat, the force of it stealing my voice in more ways than one. I could barely breathe from my excitement, so desperate to be played with by these amazing women.

My arms were pulled behind me, soon held together as an armbinder tightened around them. A rope connected to the ceiling, pulling up and up, until I found myself bent over, arms outstretched, and very much stuck. Freed from my leash, hair hanging all around my face, I shook with excitement as I felt my plug slowly pulled out of my ass.

Officer Caitlyn's smiling face greeted me, tipping my chin to stare into her eyes, watching intently. She was rewarded as Mayor Sophia's cock was shoved inside of me, her hands gripping my hips firmly as she pushed, feeling her pressed right against my ass. Eyes wide, barely able to speak, my mind slightly broke as she began to fuck the eager pink little sissy caught in her dungeon.

It didn't take long for me to cum.

In tears, I blabbered a mixture of screams, squeals, giggles, moans, whines, and whimpers. My clit erupted, squirting and leaking cum all over myself and the floor, unable to contain myself after the constant state of excitement I was left in. Quivering all over my body, the soothing hands running up and down my back and ass, both women encouraged me to release, to cum like the good girl I was.

After recovering, Officer Caitlyn pressed my tongue underneath her strap-on, moaning as I found her clit. Soon her moans echoed mine, firm hands in my wig, giving me no room to move. I focused on pleasing her as best I could, my attention stolen from the large cock thrusting in and out of me. Mayor Sophia seemed to relish in making my job of pleasing her counterpart difficult, never relenting in fucking my eager little hole harder and harder.

After cumming on my tongue, Officer Caitlyn took the role behind me, smiling as another orgasm was fucked out of me. Mayor Sophia took a break with some wine after fucking me for so long. She returned soon enough, first sliding her cock in my mouth to tease me with, before removing the harness to make better use of my tongue. I moaned, relief spread over my entire body as the frustration was fucked out of me. I happily licked and sucked on the pussy pressed into my mouth, moaning away as I came on Officer Caitlyn's cock once more.

Soon, both women exhaustedly sat back on a bench against the wall. Chatting back and forth, they sighed with relief as I, freed from the ceiling, gently licked and soothed their pussies. Moving from one to the other as directed, I pleased them both as best I could, my own exhaustion starting to show. Cute names and praise were directed my way, making my face beam with pride. Every minute of denial all night had been worth it for this very moment.

As my eyes drooped closed slowly, Mayor Sophia led me to a cage in the corner of the dungeon. I didn't even question, crawling inside to fall asleep. Both her and Officer Caitlyn kissed me good night, reiterating what a good girl I had been for them, and the party. I quickly drifted off to sleep, the biggest smile spread across my face.

Officer Caitlyn too shared a big smile, walking up the stairs behind Mayor Sophia. Tonight had been a great test for her new sissy, and she had passed with flying colours. Being the Town Sissy was what Rory was meant for, destined for. Playing with the keys around her neck, she cherished the control the judge had given her over her adorable girl. Control she had no intention of giving up.

With the help of her friends, Mayor Sophia and Jon, she'd continue her training of Rory, transitioning her into the role of Town Sissy. There was still so much to do, but she knew her good girl was up to the challenge. Subtle changes, nudges here and there, it wouldn't be long before Rory was officially a permanent resident of Great Oaks.

A decision Rory would feel she made all on her own...