The Town Sissy Pt. 05

I whimpered openly, my brain temporarily shut down from Jon's beautiful cock vigorously thrusting in and out of my ass. We hadn't had as many nights like this as before, my duties pulling me in so many directions around town. But fuck me did I miss it, that intense need I felt radiating out of him, the hunger in his grip around my waist, and the energy in his roar as his cum filled my eager little hole.

Still on my hands and knees, my clit leaking underneath me, I giggled as Jon collapsed onto the bed. I squealed as he pulled me to him, wrapping me in his strong arms, whining softly as he hadn't been able to make me cum, still feeling that urge trapped in my cage, my body brimming with desperation for my own release. But I pushed it down, knowing I was here to serve, here to be a good girl, The Great Oaks Town Sissy.

Jon ran his hand gently running through my real hair, now long enough where Mistress Caitlyn felt I didn't need my wigs outside of certain outfits. Madame Vesper had directed the stylist how to cut it, constantly complimenting on how naturally feminine it made me look, ensuring I blushed through the entire endeavour. Although I had to admit, I looked pretty fucking cute.

I snuggled up to Jon's chest, playfully stroking his spent cock, silently hoping he'd continue fucking me to the orgasm I desperately wanted. But he just sighed contently, simply enjoying the small moment of having me to himself on nights like this, the freedom to unleash that assertive and dominant energy he somewhat feared in himself. After all, to the rest of the town (and to me most of the time) he was the cheerful Butterfly Inn owner, always willing to lend a hand, a smile on his face, and a cheerful disposition to his actions.

But give him a willing sissy, some black sheer stockings, a tight shapely corset, and beckoning eyes to use her as he saw fit...well it was a different story altogether for the often lonely, kind man. Just the way I liked it.

Jon laughed looking down, seeing the look in my eyes. "You can play all you want Rory, but I'm afraid I won't be able to offer you any more for the evening." Pouting, I playfully growled at him, but eventually sighed, resigning to my denial as I so often did, resting my hand on his chest. He brought his other hand over mine, giving me a comforting squeeze as we rested in silence, savouring the calming moment after such intensity.

An entire day being an adorable sissy maid for him and the Inn, played with and tormented by the staff and guests, not to mention the session with Gregory that always left me breathless. Listening to him drift off to sleep, I tried my best to ignore the storm surging through my body, currently held hostage by my own aching imagination, unable to calm myself down for some rest.

Jon let me sleep in the next morning, eventually coerced downstairs with the smell of coffee and bacon. I sat at the bar in silence, shooting a tired, frustrated glare at anyone who dared interrupt my solitude. When Mistress Caitlyn finally arrived to collect me, she laughed at the state of her poor sissy.

"Oh dear, someone is grumpy." I whimpered as she ran her hands through my hair, softly kissing my forehead. "Did someone not get to cum last night?" I shook my head, clit already straining in her presence, my evening of denial not helping in the slightest. She pretended to pout, smirking at the desperation evident in my eyes. Reaching down, Mistress Caitlyn cupped my cage, forcing a string of tiny moans out of my lips, aching to be played with.

"Tsk tsk, you poor thing. Well, if you're a good girl today maybe I will take care of that for you." I nodded eagerly, knowing that despite all my adventures around town, no one came close to making me cum as hard as my Mistress. Toys, vibrators, plugs, or one of her many cocks, Mistress Caitlyn just seemed to know exactly what I needed, tearing me apart at times with her expertise.

After saying goodbye to everyone, I followed behind Mistress Caitlyn to her cruiser, my eyes glued to her in uniform. She wore it so effortlessly, her strong frame shown off, demanding attention from all that she passed. Not exactly new for someone to be drawn in by a powerful presence in uniform, but for the life of me I could never get over the effect it had on me.

Dressed in some pink leggings and a cute top, I blushed as we drove to Madame Vesper's shop, letting myself be marched in to hear her telltale voice booming loudly off the walls. I truly hadn't met anyone that came close to the dramatic energy emitted by Madame Vesper, always there to take you by storm.

"Rory! Ah, there you are darling. Just in time." I scrunched my face up in confusion, still unsure why I was here. Mistress Caitlyn offered no answers, winking at me before quickly leaving, probably terrified Madame Vesper might make her try something on. An arm found its way around my waist, guiding me over to her staging area, one I had found myself standing on many times since that first encounter for Mayor Sophia's party.

"What are you going to do to methis time?" I asked, my sass returning in the absence of my keyholder. Madame Vesper shot me a look, which was met by a, if I say so myself, fantastic roll of the eyes. I was getting better at it, practising for my torment of Mr. Amadi.

"Watch yourself, sissy girl. One word from me and you will spend a week in nothing but frills and ruffles!" I blushed, quietly apologising, knowing her threat was quite genuine. I had been thrown into enough humiliating dresses and outfits at the demand of Madame Vesper already, to the point that even the mention of 'poofy' made me burn a deep red.

With a huff, she moved back and forth around her workshop, pausing to take measurements or fix my posture. Soon enough I was stripped down to just my panties, groaning as a corset was tightened around my waist. Cute pink stockings, beautifully silky, held up by the garter Madame Vesper hid underneath my corset, giggling at how cute I felt. That feeling was immediately stripped from me as I saw her round the corner with a dress in her hands.

"No!" I gasped, stomping my foot at her.

"What? It is wonderful, isn't it? A traditional outfit for the annual Great Oaks Festival! Well, traditional for you anyway, dear." She hung it on the wall, carefully taking it off the hanger.

"Madame Vesper please! Pretty please? I will wearliterally anything else." I whined, staring at the monstrosity in her arms.

"Ah-ah! No fussing dear. This is the official style of dress for the Town Sissy at the festival. No buts! Now turn around and step in." I groaned, glaring at her as I felt the dress slide up my legs, feeling the dramatic collection of petticoats and ruffles seeming to make up this glorified wearable cake. I stepped into the glittery heels provided as the dress was zipped and locked into place, blushing deeply as I felt her getting everything into place.

"Mmmmm, yes okay a bit less here...take this part in...could use more here...far more on the collar...Rory stay still!" I pouted, my literal nightmare coming to life in this ball of fabric. Bright pink, with ruffled accents of white throughout, I didn't need a mirror to tell me how silly I looked. I had gotten used to all the wondrous outfits I got to wear being the Town Sissy, all the latex and uniforms. Even Mr. Amadi's schoolgirl uniform he made me wear, all prim and proper, was growing on me. But this? This!!? I couldn't let anyone in town see me wearing this.

Especially not Mistress Caitlyn, I'd never hear the end of it.

"Madame Vesper, please don't make me wear this..."

"Oh hush dear, it is a wonderful outfit. A testament to your commitment to the town if you will, and an important part of the festival. How else would Mayor Sophia be able to show you off on stage?" My eyes widened in fear.

"I HAVE TO WEAR THIS ON STAGE!!?"

"Of course, darling." I nearly fainted in her arms.

All evening was spent trying to convince Mistress Caitlyn to get me out of wearing it, met only by snickers and laughter. I whined and complained until she gently pulled a ball gag into my mouth, silencing my cries with a kiss on the cheek, feeling it buckled tightly behind my head. Tied up, stuffed into a leather armbinder, hooked to the ceiling, I whimpered being completely bound and exposed, feeling her bend down close to my ear.

"Don't worry my fussy little sissy. I'll make you forget all about that ridiculous dress." I groaned, feeling her fingers rubbing against my g-spot, melting the concerns I had tried to voice right out of my mind. Soon all I could focus on was the sensation currently trapped in my clit, remembering just how frustrated and horny I had been all day. Holding my cage in her left hand, she continued to rub and twist, listening to the noises being forced out of me with a smile on her face.

It took all of five minutes before I was shaking in my binds, cumming my little heart out from Mistress Caitlyn's fingers. My poor clit squirted and leaked with abandon, the tiny cage apart of me now, my unlocks and teases slowly becoming a thing of the past. I couldn't imagine it any other way, the intensity of my orgasms while caged far more powerful than I remembered any other way. Although, that memory was slowly fading from my mind...

Mistress Caitlyn gave my poor ass no breaks as her cock effortlessly slid inside of me. Taking off her glove, she spanked my ass hard as she bottomed out inside of me, staring intently down at her mess of a submissive sissy. No longer complaining, no longer thinking about the humiliation I'd face in the coming weeks, no longer able to focus on anything else but the touch of my Mistress, and the cock dominating my mind.

Grabbing a fistful of my hair, I whimpered as she straightened me against her. "See what happens when you're a good girl? When you'remy good girl?" I nodded, her voice a drug to me in moments like this, hanging on to every word, hammering into my mind. Emphasising her control with final spank, Mistress Caitlyn dropped me back down to hang from my armbinder, gripping my hips intently, thrusting in and out of my needy little ass.

That night, I slept like a baby.

The rest of the week I continued my usual duties around town, the festival and my appearance in it constantly nagging at the back of my mind. Even the evening spent at Hank's, in my special little booth, knowing the entire bar and town could watch me being the desperate little whore I loved to be was far preferable to being seen in that monstrous outfit. But as the day came closer and closer, I knew I was doomed, with no choice but to be a good girl and suffer my fate.

The day of the festival, squirming in Madame Vesper's workshop, I blushed through the entire process of getting me ready. I glared at Mistress Caitlyn the entire time, who consistently failed to stifle her snickering as I turned and held still, practically sewn into my frilly prison. A dramatic bright blonde wig had been made for me as well for the occasion, complete with a ridiculously large pink bow. I was no longer a sissy, now officially just a cupcake. This was the breaking point for my Mistress, who excused herself outside to laugh her traitorous head off.

As Madame Vesper placed the finishing touches where she saw fit, Mayor Sophia wandered in to see the process. As she took in the sight of me I saw the smirk growing on her face, and the blush on my own deepened even further.

"Wonderful," she said, the hint of laughter in her voice. "You've outdone yourself Madame Vesper, this is a masterpiece."

"Yes, our dear Rory will look wonderful for the festival." I pouted, not daring to look at either woman in fear my bratty mouth would get me in trouble. Beautiful pink gloves were slid onto my hands, lace and ending with even more ruffles. Quite impractical. Taking my hand, Mayor Sophia helped me off the stage, made to walk around the workshop in my dress, whimpering as I felt and heard theswish with each step. I looked pleadingly at her, but was met with nothing but her signature smirk, giving my lacey hand a comforting squeeze.

"Today we show you off in your official title, Rory." Mayor Sophia whispered, a finger tracing along my chin. Holding my gaze, she continued with her little speech. "You will be on your best behaviour, do as you're told, and represent the town in the proper way you've been taught. Do you understand me, my dear?" I whimpered softly, my poor clit hidden underneath a mountain of petticoats straining hard from being talked to so assertively.

Mayor Sophia took my shocked silence as the yes it represented, her smirk returning as she took me by the arm, leading out of the shop. Still terrified, embarrassed, and utterly humiliated, my legs nearly buckled as I was led to the final 'accessory' to my outfit for the festival, the final straw breaking my resolve, destroying any hope I had of getting through today with my dignity intact.

Grinning faces greeted me as I stared at the glass box, a metal pole with multiple cuffs placed directly in the center. Still in shock, Mistress Caitlyn wordlessly helped me inside of it, staring at my face as I was locked in place. Arms demurely to the side, legs kept together, and a collar hidden underneath my frilly dress kept me perfectly still. The metal had been painted pink to blend in, creating the illusion of a sissy doll, stationary and on display, watching as the door swung shut.

Still in shock at how they would be displaying me, I barely noticed being transported to the festival, placed on the main stage before anyone had arrived. Mistress Caitlyn winked at my wide-eyed expression, throwing a thin curtain over me for, as they claimed, a grand reveal. Just a toy put in her place until she was needed, I felt myself sinking further into that submissive mindset, suddenly no longer afraid of my outfit. This was who I was, who I wanted to be, who this town needed me to be.

I watched through the thin fabric as the festival began to fill, listening to Mayor Sophia's speech. She laid out all of my accomplishments, listening as cheers erupted in the crowd, my clit beginning to strain with delight. With a dramatic flare, she pulled away the curtain, revealing me in all my glory, the very definition of being on display, the crowd a mix of gasps and laughter. I had never blushed harder in my entire life, trying to stare straight ahead as I had been taught, letting the entire experience wash over me.

After a few minutes for the crowd to die down, Mayor Sophia opened my box, freeing me of my binds. I knelt in front of her, facing the crowd, as she placed a tiara into my wig, crowned as this year's Town Sissy, that sense of pride returning once more for the role I currently inhabited. The crowd cheered, clapping as I beamed, with only a few people still giggling.

The pinnacle of my humiliation was at an end, it seemed, as Mistress Caitlyn led me off stage, saying how proud she was of me. I blushed, feeling far more confident as many townsfolk started coming up to say hello, laughing as they playfully fluffed up my ridiculous dress. The next hour was spent posing for many photo's, my blushing face evident in all of them. Yet despite the humiliation I felt through it all, I couldn't help but smile, content at seeing the reactions to my outfit.

Mistress Caitlyn and I made our way around the festival, saying hello to everyone, taking it all in. Jon gave me a big hug for how, as he said, 'brave' I had been, making me squirm with happiness. Despite how embarrassed I had been all day, I did thoroughly enjoy the attention, the tiara resting in my wig never leaving my mind.

I felt her hand squeeze mine. "See? Not so bad being put on display for the festival, huh?" I pretended to glare at her, but it quickly dissolved into a smile.

"No, I guess not. I still feel so silly, though." Mistress Caitlyn laughed, offering an arm for me to take.

"Yes, well, that is kind of the point, my dear." I hugged her arm tightly as we walked, enjoying being so close. Leading me carefully through the crowd, we soon were in a large tent set up for an assortment of games. I sighed with relief as Mistress Caitlyn carefully let me out of the ridiculous dress, feeling a giant weight lifted off my shoulders as I was freed from that humiliating display of bows, ruffles, and fluff.

Left in my corset, stockings, and lace gloves, Mistress also stripped me of my panties, somehow feeling far less on display than I had earlier. Smiling at me, she playfully poked my nose. "Now, for the fun part of the evening. I think, my dear Rory, that you're going to like this..."

The festival organisers had set up booths specifically designed for me, spread out around the tent. First I found myself bent over a wooden bench, arms stretched out in front of me with my legs shackled apart. Placing a curtain to leave only my ass, legs, and clitty on display, the bedazzled pink letters above me spelling out,The Spanking Booth. Finally freed of my utter humiliation, the confidence of my role returned to me, I happily gave all in attendance the BIGGEST eye roll I could muster, sighing at the name they came up with.

Soon enough I felt the first smack against me, a playful hand, causing me to giggle. Apparently they could buy tickets to spend at my booths, each one awarding two spanks. However, more and more noise and excitement buzzed behind that curtain hidden from me, only able to squeak and whimper as I felt my ass heating up from the attention. Palms, crops, flogs, paddles, and canes were all used in a variety of ways, some even drifting down to be aimed at my poor, desperate clit. It didn't take long to start bringing tears to my eyes, on fire from my torment.

Thankfully, I was given breaks to rest and have lotion rubbed over me, but by the time I was released from the booth I felt on fire, sniffling against Mistress Caitlyn. She called me her brave, strong girl as I was led to the next source of entertainment. Barely noticing what was being done to me, I moaned happily as I felt my plug removed, sliding down onto a metallic cock attached to a pole. Once more in a similar position to my glass box, I was spread wide and on display, still whimpering from being spanked so thoroughly.

Regaining some composure, I looked to the right in horror to see a bullseye, similar to the dunk tanks I'd seen at carnivals. Not seeing a giant collection of water anywhere, I groaned as I deduced what must be buried deep in my ass. Sure enough, as the first throw made its way to the target, I squealed as an electric shot tore through me, my clit twitching consistently afterwards. I stared down at the growing line of people and whined, trying to plead with Mistress Caitlyn, only to see her smirk, waving tickets of her own back at me.

This was going to be a long, painful night.

They turned me into a human dart board, an interactive picture display, a candy dispenser, and at one point, a napkin stand. A. Napkin. Stand. RUDE! As the sky darkened I sighed with relief seeing the crowd begin to dissipate, hoping for some form of a break in my duties. Mistress Caitlyn returned from her own festival exploration, arm in hand with Mayor Sophia, both snickering at the state of the Town Sissy. I offered both of them the best glare I could muster.

Fixing my wig, which was a mess by this point, Mistress Caitlyn still unsuccessfully stifled her laughter as she patted my cheek. "Oh Rory, you did so well tonight! Everyone thought you were a hit." I pouted, trying not to show how much joy I received hearing her say that, wanting to be mad at the experience. But this just made them laugh all the more, steading me on my heels, each taking one of my arms as I was marched away from the tent of horrors, as I decided to refer to it as for the rest of time.