The Town Sissy Pt. 01

At first I meant for this to be a fun, quick story. But the more I delved into it, the more I absolutely loved the idea! So this one will have to be spread over more parts to come :). I hope you all like it! <3.

Part One: Sentenced

"This isn't fair!" Pouting, I stomped my heel on the ground, outraged at the injustice I was currently facing.

"You will control yourself, miss temperamental sissy. Getting caught soliciting sexual favours in this town is a serious offense." Judge Isaac stared down at me from his high horse, already having made his mind up for this troublesome 'outsider' that had been caught in town. Caught under false pretenses!

I had wandered into a wonderful small town, a village really (but they were super touchy about that!), called Great Oaks. Tightly knit community, cute downtown, I thought it was a great place to explore as Rory for the day. Wearing my favourite red dress, hugging every part of me, I donned my matching heels and some black tights, happily wandering through this tiny part of the world.

The dress might have been a tad too short, I'll admit, but I wasn't a prostitute! All of that, however, fell on deaf ears with Officer Caitlyn, who promptly stormed me off to the station. Two days later and the gavel slammed down on my freedom, pouting but slightly worried what was to be done with me. Not to mention, they had 'possessed' my belongings, which of course included my key! My poor clit ached in my cage, always so excited to be dolled up, constantly reminding me of my unfortunate situation.

"Now," Judge Isaac continued, that firm gaze making me squirm in my heels, "as for what we do with you." I huffed, still annoyed that I had been found guilty so quickly, with zero evidence. "Being a small town, we cannot house you for the extent of your sentence, and sending a sissy off to the city just doesn't seem right. So, you will serve the town instead."

"And how exactly do I serve the town?" I asked, knowing sass would not help my situation, but chastity and a cute outfit unfortunately always brought out the brat in me. Glaring, annoyed at the interruption, Judge Isaac continued.

"You are sentenced to six months of community service, which will be served at The Butterfly Inn. Recently fallen on hard times, you will help Jon, the owner, in keeping it up to date and in pristine condition. Other duties may arise, at the discretion of the courts." BANG, another dramatic gavel hit sealing my fate. Before I could complain about the ludicrous situation, I was firmly led out of the courtroom.

Outside, squinting in the sun, I was greeted by a smirking Officer Caitlyn. Stuffed into the back of her car (still wearing handcuffs, rude!), she drove off, grinning at the pouting sissy in her mirror.

"Oh cheer up," she said, smiling. "It is a lovely little inn, and the six months will go by in no time. Who knows, you may even grow to like Great Oaks!" I glared at my captor, who simply laughed, soon arriving in front of my new 'home'. It is actually a cute inn, I thought to myself, staring up at the main lobby. The rooms seemed to be spread out through an adjoining building, with a side cottage just off the back.

Officer Caitlyn opened the door, dragging me along by the arm as I tried to keep up in my heels. I softly growled at being handled this way, which only resulted in the smile widening on her face.

"Hi Jon, meet your new little 'helper' for the next six months." Presented in front of a timid, kind looking man, I refused to drop my pout as he looked me over.

"Really, Caitlyn? Was that the verdict? Oh, that is wonderful!" Smiling, Jon hugged me, pulled into his chest. Hands stuck behind me, I could do nothing but sigh, waiting for his embrace to be over. "I know it isn't ideal for you, sweetheart, but this inn could really use the help. Don't worry, a few days in your new uniform and I promise you will like it here." I huffed, sass still the only response I was willing to give, but a small part of me was glad he seemed so nice.

I was marched to my room, tucked in the back Service area beside the laundry. It was spacious enough, with my own bathroom and closet, as well as a big wall mirror. I did like mirrors. Sat down in my chair, I stared up at Officer Caitlyn as she leaned down in my face.

"Now, my little sissy, I want you to listen very carefully." Smile wiped off her face, stern and demanding, I gulped as she continued. "Jon is a wonderful man, a treasure of this town, and loves this inn. I will be by each day to check on you, make sure you are behaving and being a good girl. Any bad words from him and you will be punished, possibly your sentence extended. Do I make myself clear?"

I whimpered softly, unable to ignore my arousal from being treated like this by such a dominant woman. Even in my current predicament, I couldn't ignore how attracted I was to her, or being told what to do. Staring back at that commanding look, her tone reverberating in my mind, I could only nod, eyes wide as I was transfixed. Seeing she had my full attention, Officer Caitlyn continued.

"Good." A slight smile returned to her face. "The courts have designated me as your 'parole officer', if you will. I will report on your sentence, how you behave, and if there should be any...leniency in time." My eyes widened at that news, clinging onto the hope I wouldn't be stuck here for the full six months!

"Part of that responsibility, is taking care of that cute little clit of yours." My throat dried up as I saw her pull out a package, showing me an extremely small cage, far tinier than I was used to. I've heard of government regulated cages before, but I never thought I'd find myself in one!

"That is too small!" I pleaded, trying to convince her mine was fine. But Officer Caitlyn shushed me, arms still cuffed I could only watch as she took MY key, and unlocked my clit. Despite my terror of the cage she held in her hand, I sighed with relief feeling it removed, aching and immediately excited. Taking off my ring, she tutted, watching the blushing sissy before her grow and harden.

"Now Rory," she purred, voice soft as she stared into my eyes, "that isn't being the good girl I told you to be, now is it?" I whimpered, each word of hers slamming into me like a hammer.

"I can't help it..." I whispered, barely able to talk as she sat on my lap, straddling my legs with hers. Gently, she ran a finger along my poor clit, aching to be rubbed and played with, stuck in its cage for the last few days. Whining, desperate, I felt myself twitch, wanting more of her touch, but a taunting finger was all I received.

"I'll tell you what," Officer Caitlyn continued, her hand under my chin bringing my eyes to her. "Each week I will come by and unlock you, make sure you're okay and clean. If you've been a very good girl, did everything you're told, the perfect sissy...then maybe, just maybe, I will play with this." I openly moaned, unable to help it in her hands, her control. "Would you like that, my little sissy?" Whimpering, I nodded, feeling desperation between my legs.

"So you are going to be my good girl? No more of this attitude? No giving myself, Jon, or this town a hard time?" Her spell complete, control ironed out over me, I gulped in defeat, knowing I'd do anything for this beautiful Goddess.

"Yes..." I whispered.

"Yes Officer Caitlyn" she demanded, that stern look melting me completely.

"Yes Officer Caitlyn" I relented, bringing a smile to her face. Leaving my lap, she spread my legs, dress hiked up further so I could be re-caged. Gentle but firm spanks to my poor balls chased my erection away, ready for the new, impossibly small cage. Pink, some kind of 3D printed material, I couldn't believe how squished I was! Thin strips in the cage and ring seemed to stick to my skin, holding firm against me, helped by the leather harness Officer Caitlyn helped me step into.

Taking off my dress, she led me to the mirror, admiring my new cage, as well as the look of horror on my face. Clit once again straining, I whimpered as I got excited, but my cage remained unmoved. Seeming to grow inside of me, that familiar strain, that constant ache, seemed far worse in this cage. I couldn't think of anything else, my mind consumed by this new feeling. Pleading, staring up at my new keyholder, seeing it go around her neck and disappear underneath the uniform, met simply with a loving laugh.

"Don't you worry," Officer Caitlyn said, gently patting my cheek. "You will be used to it in no time! Besides, it looks so cute on you." Her hand moving to the back of my neck, she kissed me on the lips, stealing a moan as I melted into her. Pulling away, leaving me wanting, I was ordered to strip completely, donning my new 'uniform'.

I groaned as it was pulled out of the closet, seeing the petticoat and ruffles that came along with it. Laughing, enjoying my personal torment, Officer Caitlyn watched as I slid panties and white tights up my legs, pulling the dress over my head. Settling it around me, petticoats positioned properly, I sighed as the hem was pushed out, swishing with every movement. How was this the uniform for this inn!

White collar, matching ruffles running at the hem and top of my sleeves, blushing at the very sight of them. As I stared into the mirror, I gasped as I felt my waist tightening, seeing the apron hugging firmly. Bringing in my waist, completing the outfit, I pouted as I slid into my reasonable heels, finishing my uniform. Fairly practical, with just enough of flare, ensuring everyone knew I was a maid...but also a sissy. There'd be no hiding in this thing, that was for sure.

"Just wonderful, it is just perfect for your position here." Smiling, laughter behind her eyes, Officer Caitlyn playfully lifted the hem of my dress, letting it fall against the petticoats. Groaning, my pleading not working, I let myself be marched back into the lobby, to the excited eyes of my new boss.

"Oh it is perfect!" Jon exclaimed, "It has been so long since someone has worn that uniform at the inn. Perfect." I rolled my eyes, wondering who was the last poor soul they tricked into working here. A pinch on my butt make me squeak, Officer Caitlyn reminding me of my place. Blushing, I dropped into a curtsy for Jon, burning with humiliation as he praised.

"I will leave her in your care, Jon. Be sure to let me know if she is trouble."

"Nonsense, we will be just fine, won't we Rory?" Jon said, still admiring me in my new outfit. Sighing, I nodded, still feeling the glare directed at me from my keyholder. Satisfied, she left, leaving me in the hands of my new employer, my new role for the next six months. Jon happily led me around the inn, showing off the rooms and history, pointing out things left and right. It had been in his family for generations, and a pinnacle staple in Great Oaks.

I learned that his wife had passed away some years ago, seeing the sadness behind his eyes. My heart went out to this kind man, who seemed to love her very much, squeezing his hand for support. Smiling, he bounced back to his cheerful self, continuing room to room to show me my duties.

"Having you here, Rory, will be just perfect! It's just been me and Gregory of late, not many guests to take care of. But I am sure things will turn around." Jon smiled, his tour ending back in the lobby.

"Gregory?" I asked, seeing no one else through the inn.

"Oh how rude of me!" Jon exclaimed, "Gregory is our Groundskeeper, he lives in the small cottage out back. Let's go meet him." I groaned internally, my hope of not being seen outside in this outfit diminishing as I was led hand in hand to the small house, clicking heels off the walkway.

A rough older man, grunting as Jon introduced me, very much fit the bill for groundskeeper of a small inn. Gregory seemed very much the keep to himself type, although I learned that cleaning his small cottage was also on my list of chores. Great. I was very much looking forward to those awkward interactions.

Returned to the lobby, Jon gave me another of his long hugs. "I know you were sort of thrown into this, Rory, but know that myself and the town are glad you're here." Kissing my cheek, the cheerful smile that greeted me bringing a smile to my face for the first time in days. "I promise, that if you do everything you're told, mind your manners, you will find the role of Town Sissy very enjoyable."

The role of what!?

Before I could ask, Jon headed off, leaving me with a list of chores for the day, and a heap of questions. What exactly was a 'Town Sissy'? That isn't exactly a known thing you can just throw out there like that! Huffing, my mind on fire, I went about my list, frustrated for multiple reasons now as I began cleaning the first room.

All day as I ticked items off my list of duties, the phrase 'Town Sissy' replayed in my mind over and over. I rarely said that word out loud, never mind in public. And yet, this town has a designated position for it? Does it come with benefits? Do I get a pension? Sass boiled up inside of me, feeling the effects of my new cage and uniform, needing some kind of release or distraction.

Looking at my final chore of the day, I groaned, the dreaded awkward meeting with Gregory happening sooner than I thought. Heels clicking off the pavement for the second time that day, a small blush on my face as I strolled outside in my uniform, I knocked on his door. Not getting an answer, I carefully entered, the main room in fairly good condition.

"Helloooooo?" Softly searching for Gregory, I echoed a few more times before assuming he was off doing groundskeeper things. Taking out his vacuum, I went about cleaning, finishing fairly quickly as I started straightening the kitchen. Tap running and in my own world, I squeaked when I felt a hand on my lower back, Gregory's scowling face greeting me. Heart beating from being scared, I blushed with shaky hands as I curtsied, assuming the courtesy was required for everyone.

That expression never changing, he grunted for me to finish and meet him in the bedroom afterwards. I assumed he wanted to show me what not to touch, seeming a very private man. Bathroom scrubbed, kitchen clean, I smiled at the state I left everything in. I may have been forced into this role, but I did enjoy being a good little maid.

Finding Gregory on the bed watching tv, I curtsied once more as he sat up. Beckoned to the front of the bed, he had me kneel down. Taking my wrist, I watched as he tied it to the end of his bed, doing the same for the other. Soon spread wide and stuck, I tried to protest, but he simply ignored my pleas, thighs bound as well. I squirmed against the rope to no success, glaring at the silent kidnapper in front of me.

Returning my stare, he informed me that I was never to come in here without permission. A firm hand on my jaw, ensuring I was fixated on him, I nodded that I would stay out. Those eyes never leaving me, the seriousness in them making my clit start to twitch with excitement. Forcing my mouth open, I whimpered as he buckled a ring gag behind my head, trapping my wig tightly against me.

"There's one more thing you are going to clean for me each week." I watched as he unzipped his pants, cock soon running up and down my tongue. I thought about protesting, saying this wasn't part of my job. But the phrase, 'Town Sissy' flashed in my head, as well as Officer Caitlyn's warning to do as I was told. Straining in its new prison, my clit was clearly enjoying being dominated in such a manner, mouth used to please him as he groaned, slowly pushing in and out of me.

Hard, firm, and yummy, I soon was lost in being his little cocksucker. The satisfied groans emitted fueling my pride to be a good girl, wishing I could do more to help. But Gregory, had other plans, hands firmly holding me in place. I was here to be used, nothing more. Pushing deep down my throat, he watched me gag each time, never going too far, testing my limits with each thrust. Soon my eyes were filled with tears, mascara running down my face as he continued, falling further into my temporary role.

Gregory's patience was rewarded as I felt my nose pressed against his skin, cock buried down my throat. He patted my head, calling me a good girl, gasping for breath when allowed, only to have it stolen from me once more. I didn't move or argue, simply staring up at my captor, clitty straining while he used my mouth. I couldn't believe how much I loved having a cock in my throat, suddenly knowing I'd look forward to my weekly cleaning visits.

My make-up a mess, satisfied with the messy bound sissy before him, Gregory groaned as he came inside of me, pumping cum down my throat. Pulling out just slightly, he made sure to coat my mouth as well, tasting him swirl around on my tongue. The last few shivers of his orgasm, twitching cock pulled out of my mouth, he made me swallow what I could, returning his cock to be cleaned. It was my job, after all.

Untied, Gregory helped me to my feet, my mouth coated in his cum. I knew I'd taste him for the rest of the day, blushing as I felt his hands on me. Letting me regain some composure, he patted my butt appreciatively, walking me to the door.

"See you next week, Rory. Looking forward to it." Door shut in my face, still getting out of the mindset of being used, I walked back to my room in a daze, nearly running into Jon with my mind elsewhere.

"Rory!" Jon exclaimed, seeing the state of my make-up. "Ah, I see you've been to Gregory's, good. He is a bit eccentric that one, but has a good heart. You okay, sweetie?" I blushed, nodding as he took me by the hand to get cleaned up.

"You did excellent today, Rory. Caitlyn will be very pleased, as am I." Back in my room, I blushed from the compliment, Jon's hand resting on my tights as I sat down. He helped me out of my dress, soon gently rubbing my clit. Moaning in his arms, my resolve melted completely after Gregory, I turned even more red as he noticed my excitement.

"Looks like someone enjoyed their day being a maid, didn't she?" I nodded, not wanting him to stop playing with me, touching me. Staring up at my employer, he kissed me deeply as I whimpered, falling further into my role. As my clit strained in its tiny prison, I no longer cared I had been unfairly punished. I knew deep down, this is what I wanted.

Pulling away, leaving me wide-eyed and desperate, Jon smiled at my mental state. Gently patting my face, he told me to get cleaned up, knowing Officer Caitlyn would be by soon to check up on me. Left on the bed a mix of frustration and excitement, I pouted getting ready for the shower. Clit perfectly restrained, aching with need, reminding me of my predicament. I knew I'd need some form of release soon, or distraction to take my mind off it.

Stepping out of the shower, I was greeted by my keyholder, comfortably sitting on my bed. Tight jeans and a cute white top replaced her officer uniform, those stern eyes making me melt immediately.

"I heard you were a very good girl today," Officer Caitlyn calmly stated, never letting me leave that commanding gaze. Blushing, I nodded, finishing drying myself off in her presence. Beckoned to her, I knelt naked in-between her legs, softly moaning as she gently placed my wig on, framing my face. Smiling down at me, I felt such warmth spreading through my body, a growing need of...something. I just didn't know what it was.

With a whispered voice, still feeling very subby and shy, I asked the question that had been on my mind all day. "Officer Caitlyn? What is a Town Sissy?"

"Ah, I see Jon's big mouth has been going off again." Officer Caitlyn chuckled, pulling me onto her lap. Stroking my clit, pulling whimpers out of me, she continued. "Well honey, it's a very important position in town, you see. Every once in a while we get a girl like you, some more willing than others, who helps keep things...calm." Her fingers never stopping, ensuring she had my full attention. I hung onto every word, never wanting to leave her embrace.