The Town Sissy Pt. 05

Mayor Sophia squeezed my arm. "We have one more event for you to take part in tonight, one we think you'll like even more than all of the others put together!" I growled at her, my ass twitching just being reminded of at least three of them. More laughter from the two women as we entered a supply shed for the festival grounds, emptied of tools for the time being. A curiously looking beam ran against the back wall, with a step coming off the front of it.

Confused, I looked to Mistress Caitlyn, who's answer to my quizzical look was to force my mouth open with a cloth, moaning in surprise as she gagged me into silence. I whined at her, but her stern look took any steam out of my resistance, placing a piece of tape to keep my mouth shut. Mayor Sophia replaced my wig with a latex hood, setting it in place so I only had access to the world through two tiny nostril holes.

I whimpered, my clit straining from being handled so roughly, slightly terrified for what they had planned next. I followed as they pulled me in place, lying down with my ass in the air, feeling my ankles tied up above me. Arms pulled tightly to either side, more rope ensuring my thighs and legs were stuck together, the block of wood beneath me forcing my ass upwards, fully exposed. Immobilised, with at least two senses stolen from me, I could only moan, waiting for my next duty.

I wasn't left in the dark for long, well metaphorically at least, as strong hands spread my asscheeks wide. A thick cock pushed its way deep inside of me, my thighs being tightly bound making it feel even bigger as I moaned and quivered, feeling it slide against my g-spot. Keeping me spread wide, squatting on the box that was forcing my ass in the air, they began fucking my little hole to their liking, forcing my mind into a haze of need. So easily turned into the desperate little slut I had been trained to be, moaning loudly against my gag at being fucked so well by this stranger.

Far sooner than I would have liked, I whimpered in protest as they pulled out of me, feeling empty after being stretched so well. Moments after, I felt drops of liquid splashing against my back, sticky and hot, running down over my shoulders. Given no time to work out what had happened, my mind was kidnapped once more as another cock pushed its way inside of me. I couldn't even push back against this new invader, stuck in place to be used. To be fucked.

Breathing heavily, the wonderfully tingling sensation trapped in the tip of my clit, I felt once more the drops of something on my latex hood, dripping down the side of my face. Closer to my nose, I definitely recognised it as cum, realising that they were emptying condoms out on me! Knowing I was being covered in cum after the fact, dropped on me after being used so thoroughly, immediately drove me wild, wanting more yet denied it.

With each cock I felt myself being covered more and more, all over my back, head, and arms. I squirmed with each condom being emptied, feeling my arousal heightened over and over, knowing I had already made my own mess beneath me several times over, my clit a constant mess of twitchy happiness. All I could do was picture the bound sissy, tied up in a shed, being used by whoever wished, covered in cum like she deserved. It was easily the hottest thing I had ever been put through...

I screamed through another orgasm, unsure how many had been fucked out of my exposed little hole, twitching and squeezing around the cock inside of me. I faintly heard laughter, along with an appreciative tap on my ass as I caught my breath once more, soon after feeling more cum being added to the collection. After I felt the floor creak as they left, I sighed with relief feeling myself being untied, only slightly wishing it could have continued, but feeling on the brink of exhaustion.

Mistress Caitlyn carefully stripped me of my hood, smiling at the wide, tired, and happy eyes that greeted her. Taking a towel, she helped clean me off, a sticky mess of cum, sweat, and dirt. Wrapped in a fresh towel, waving goodbye to the remnants of the festival, she drove us both home, soon finding myself moaning in a different light as she helped me soak into a warm bath.

Cleaned of my evening, and all that it entailed, I snuggled into Mistress Caitlyn's chest, whimpering as she started showing me photo's of being bound, watching as I slowly descended into the cum-covered cocksucker that I knew deep down I so enjoyed being. Using her other hand, she gently rubbed my clit, feeling it tighten as I whined, my mind once more tormented with need and desire.

She stared down at me, seeing the state I was in, planting a deep kiss on my lips, my chorus of tiny moans greeting her appreciatively. Putting her phone away, Mistress Caitlyn caressed my cheek with her hand, never stopping her gentle rubbing of my cage and balls.

"Rory," she started, a nervous look in her eyes I'd never seen before, "next week you will have been the Great Oaks Town Sissy for six months."

"Oh." My eyes wide, almost forgetting that I had been sentenced to this position in the first place.

"Yeah. There's a trial where Judge Isaac will look over your service, and determine if you have served it to completion." She continued her stare, a determination behind those beautiful eyes. With barely a whisper, she said the most beautiful, tormenting words I had ever heard.

"I want you to stay."

I whimpered, barely able to breathe, in the arms of the most amazing woman I had ever met. Mistress Caitlyn continued, never taking those eyes of hers off me.

"I know this has been your temporary home, and you have a life outside of this small town. I know you were thrown into this, an unorthodox position if there ever was one...but it was made for you. This town needs you, baby girl." Leaning down, she kissed my lips once more, her eyes closed as she rested her forehead on mine.

"I need you."

Mistress Caitlyn held me tightly, not looking for an answer. I could only stare at the ceiling, holding onto her for dear life, my clit straining in the impossibly small cage I had worn consistently these past six months. The prospect of staying here longer hadn't really crossed my mind, however the time had flown by so quickly under the control of so many wonderful people that I hadn't really thought about it. Did I want to leave? Was this the life that I desired? Could I give up being under the control of Mistress Caitlyn?

I had no idea, my mind a constant stream of questions. The only answer I did have, was knowing that the next week was going to be very, very, very...fucking hard.