The Town Sissy Pt. 04

Two months after moving in with my Mistress Caitlyn, my new life had finally seemed to settle down. Well, as much as the position ofTown Sissy could be 'settled', I suppose. After all, I technically was serving out a sentence (that I most certainly didn't deserve!) that I had completed half of. Six months of service to this little town of Great Oaks, providing new experiences, wonderful people, and exhausting fun so far. I often caught myself forgetting that this was supposed to be a punishment.

My clit, however, was more than happy to remind me. Rude.

A mandated pink cage, firmly held in place by my mandated pink harness, the constant feeling of being constrained keeping me company day in, and day out. Each morning, straining from my own imagination, whimpering as I squirmed back and forth in bed. Staring down between my legs, seeing my adorable clit pulsing with a desperate need, I often worried that I would forget how to have an erection at all...

Mistress Caitlyn is always happy to remind me.

Strapped into a special chair she had made just for me, I would spend hours in her expert, relentless, and tormenting grasp, begging for a release. But she always just smiled, letting her poor girl ride that thin edge of denial, only to guide me once more to that constant state of desperation.

Even at my worst, when I feel like my poor clit is going to burst from its cage, the need coursing inside of me chewing away at my sanity, I pray she keeps me locked tightly and secured. The teasing was far worse, borderline evil! Whimpering, my body quivering with an insatiable urge to cum, wordlessly staring down at my Mistress, while she gleefully denied me...over and over again.

So I welcomed the ache between my legs, the constant reminder to be a good girl, to fulfill my role to the town. Instead of a traditional release, I sought distractions from my own mind. Thankfully, my job provided just that.

Twice a week I still helped out at The Butterfly Inn, buzzing around in my cute maid uniform under the watchful eye of Jon. Sweet, adorable, caring Jon. He always had a smile for me, or a gentle pat on the butt as I walked by, always forcing a blush on my cheeks. Of course, until I visited him at night, a vessel for him to pour out his frustrations and cravings into. I had lost count at this point how many nights I had fallen asleep against him, cum leaking out of my ass and clit, softly moaning as he kissed me.

My weekly visits to Gregory continued as well, they had to. He was already so grumpy, imagine if I stopped helping!? His collection of rope, leather, and gags had been exhausted on me over the last three months, intimately familiar with all of it. Many people in town enjoyed holding power over me, using me for various reasons. But few did it so completely, intently, and mind shatteringly well as quiet Gregory. My poor clit always strained with more difficulty when I went to serve him, as well as my throat...

However my role had expanded over the last few months from simply being a maid. After moving in with Mistress Caitlyn, the town seemed to warm up to its new sissy. Walking through main street I felt like a celebrity, with people waving and greeting me at every shop. Rarely did I not feel hands exploring whatever outfit had been chosen for me that day, pulled behind counters or walls, sometimes even bushes! I was a busy girl.

And I loved it.

My favourite change was most certainly and definitively being able to serve Mistress Caitlyn more frequently. Sometimes I stayed at the inn if I worked late, or I was requested at a party. But typically a familiar cruiser would arrive to bring me home, often with a smirk on her face as she used the handcuffs on her belt. One time she bent me over the hood of her car in the center of town, claiming I had to besearched. All I could do was blush, burning red as I felt hands explore my body, legs spread willingly, listening to a chorus of cheers and laughter behind me.

For the most part, however, Mistress Caitlyn just took care of me. Oh sure, I did all the chores, a pair of hungry eyes following me as I pranced around the kitchen. But at every turn I felt her tender touch on my body, squeezed from behind as she called me a good girl, bringing me water and snacks after being used like the sissy plaything I was becoming. Falling into her arms after one of her many cocks tore several orgasms out of my poor, desperate little ass, a sense of contention so overwhelmingly powerful always washing over me.

I wanted this, all of it, I realised. I was happy.

That didn't stop me from pouting in front of the mirror, growling as Mistress Caitlyn shushed me, continuing to perfect my 'uniform'.

"Why do I even have to wear this stupid thing?" I asked, stomping my black three inch heel on the hardwood floor. I quickly apologised, looking down at my fumbling hands, as a strong eyebrow was raised in my direction.

"Because Mr. Amadi requested it, Rory." Her stern response resonated in me, the brattiness I felt earlier chased away by that commanding tone. Bringing her lips close to my ear, I felt her hot breath against my skin, softly whimpering anytime she did this to me.

"And because I said so." My little outburst was sealed with a spank, Mistress Caitlyn returning to her inspection. Promptly put in my place, I remained silent as she smoothed out my dress. Solid black, matching my heels, the fabric hugged my waist tightly, no doubt Madame Vesper's work. Coming just above my breast forms, hidden away by a traditional white collar blouse. An insignia was stitched right between my boobs, an intricateS with the official crest of my office. I rolled my eyes every time I saw it in the mirror.

Beige stockings were held in place by my garter belt, the straps always making me a little weak, feeling them against my thighs. I whined as I felt Mistress Caitlyn tighten my tiny little tie around my neck, tucked into the front of my dress. The finishing touch, a wide white ribbon, was tightly cinched around my waist, sighing because I knew she was going to make a ridiculous bow back there that I couldn't undo!

Why did it have to be so formal!? I loved being a schoolgirl! The cute skirts, nylons, a collar shirt tied up to show off my belly button ring. Why mess with a classic? But nooooooo, 'Mr. Amadi' demanded that I be trussed up as some vintage troubled girl, needing to be taught some manners at the end of a meter stick.

Apparently he had approached Judge Isaac, concerned over my taking this punishment 'seriously'. So NOW, I had to meet with him every other week, sitting in his classroom at night while he rambled on about ethics or something. Whenever he caught me not paying attention I was promptly placed over his lap, feeling his hand or ruler on my ass.

I won't lie...I got spanked a lot.

Sighing, I pleaded with Mistress Caitlyn to get me out of this ethics nonsense the entire ride over, not appreciating the smile on her face with each no she gave me. I gave her one final sassyhmph, before stepping out of the car. As I walked up to the school, I heard the window roll down behind me.

"Have fun at school, sweetie!" I turned, glaring at her EXTREMELY HARD, listening to my Mistress cackle at the top of her lungs as she drove away. Not nice. I walked inside already scowling, plopping down at my desk, head in my hands.

Mr. Amadi stared down at me, those bushy eyebrows and comically large glasses not doing him any favours. Without a word, just his judgmental stare, I sighed audibly, sitting up straight with my hand folded in my lap, as aproper lady would. As he turned back to look at something on his desk, I also stuck my tongue out at him, as my sassy sissy personality demanded.

"Legs together when you sit, Rory. We've been over this." Those disapproving eyes glaring at me. I rolled my eyes in his general direction, carefully picking my response.

"Did we? I don't remember that lesson."

Not even five minutes in and I was across his lap, my ass quivering as I felt my school uniform being flipped up, exposing my panties. Mr. Amadi started with his hand, forcing whimpers out of me with each spank, watching my ass redden in front of him. Satisfied with the colour, he slowly peeled off my panties, sparkling plug reflecting the light in the room.

"Why must you force me to discipline you, girl?" That stern tone of his seemed to reverberate through my body, as I failed to stifle a giggle. He sighed disappointedly, continuing with his self-righteous speech. "We are going up to fifteen today, make sure to count each one or I shall start again."

"Fifteen!" I cried, sometime later, sniffling with tears in my eyes. Mr. Amadi slid my panties down the rest of the way, assuming I'd end up across his lap once more before the lesson was over. Returning to my seat, I gingerly slid into the chair, wincing only slightly from my punishment. I felt the fabric of my dress gently teasing my now exposed clit, already leaking from being treated so roughly.

I tried to behave for the rest of the lesson, listening as he rambled on about proper etiquette at a dinner party, or greeting an old friend. However it was so boring, and I felt myself drifting off to sleep. A loudsmack! on the desk brought me out of the beginnings of a daydream.

"Rory!"

I whined in response, "I'm sorry Mr. Amadi! But who cares about all this stuff! When on earth am I going to use any of this as the Town Sissy in the next three months!?" I pouted, returning his stare in kind. "I hardly spend enough time off my knees to curtsy anyone anyway."

Then, what can only be described as a miracle happened.

Mr. Amadi smirked.

Extremely subtle, as if his mouth could only flex half a centimeter, but he smirked. I didn't think it was possible. Standing in front of the class, he beckoned me over. Eyeing warily his stick, I knelt down in front of him, looking up at that permanently frowning face.

"What do you think people see, looking at you? Looking at the crest of the office you hold, Rory?" I scrunched up my face in confusion, not sure what he was getting at. Taking a firm finger, he pointed between my breasts, emphasising his point, the embroidered patch on display at the center of my uniform.

"This, my dear." Mr. Amadi continued, ensuring he had my full attention. "Wearing this, holding your title, you always represent the town. Every interaction, every person you meet, every party you attend. You are a focal point of Great Oaks, young girl, an attraction if you will." He held me in that stern gaze, my lips parting to the tiniest of a moan, feeling myself sink further before him.

Leaning down, his face close to mine, eyes locked together. "Your attitude matters. Your appearance matters. Your behaviour matters." As I wilted, he cupped my chin, the first act of warmth and kindness I had felt from him in the last few weeks.

"You, my dear, matter."

I gulped, slowly realising that I had been wrong. Mr. Amadi really was trying to help, even if I found the formality of it all quite silly. Eyes cast down, I softly apologised for being a brat, for not taking him seriously. He held me there for an eternity, letting the silence of the moment sink in, ensuring I had learned this valuable lesson.

Finally he removed his gentle grip of my chin, leading me over to his desk. I whimpered, mentally preparing for another spanking. My dress was once more slowly flipped up, ass and plug exposed to the empty classroom. I felt his wrinkled hands caress my ass, squeezing every so often, exploring down my thighs, running up and down my stockings. Fear turned into moans as I felt his touch, my clit pulsing from being treated so tenderly.

Mr. Amadi's hands did return to spanking me, but they were more playful, less intense than being across his lap. I began to shake intently as my princess plug was removed, followed by his pants and underwear neatly placed and folded on the desk beside me. He directed me to spread my legs a certain amount, my arms placed on my back, holding each elbow in turn. Head facing forward, my eyes widened in shocking delight as his cock slid inside of me.

Using a consistent, but slow pace, he pushed in and out of my eager little ass. Every so often Mr. Amadi corrected my posture, quieted my moans to something more appropriate, a firm tap on my ass guiding me in my new lesson. And for this first time since being tutored by him, I listened. Intently. I could feel my clit on the verge of exploding, my orgasm seeming to always be there now after three months of cumming from being fucked. Being the Town Sissy had turned me into the perfect little whore.

But Mr. Amadi never quickened his pace, never fucked me quite hard enough to push it over the edge. When I asked him if he'd make me cum, he tutted, that guiding hand patting my ass once more.

"No, Rory. This isn't for you. Your role here is going to require you to serve on occasion, more than one I'd assume." I whimpered as I listened, breathing deeply as he continued. "You need to learn that your service is first and foremost to those around you. Not your own selfish desires. If those are given to you, then you are to be extremely grateful." I felt a hand grip my hair tightly, lifting my head while I whined, nearly shaking with the building need I felt in my body.

"Now, my dear. Tell me." Brought up to his ear, he half-groaned through his question. "Who are you?"

I panted, my mind unraveling from being fucked so softly. "I am the Town Sissy."

"Who do you serve?"

"I serve Great Oaks."

"Who are you?..." Over and over he had me repeat it.

"I am the Town Sissy. I serve Great Oaks."

Over and over, his thrusts never quickened, steadily tearing me apart with no release. I focused intently on my new mantra, suddenly no longer thinking of my own orgasm, falling into the rhythm of being used. Of being a good girl.

Of being of service.

I barely noticed when Mr. Amadi pulled out of me, neither of us cumming from the nearly thirty minutes of fucking. I collapsed on the desk after he released my hair, shaken to the core from my most important lesson. After collecting himself, Mr. Amadi dressed silently, straightening his blazer before helping me back into my panties.

Feeling like a puddle of submissiveness, I floated back to my desk, in a daze as I sat with my back straight, hands collected in my lap, legs together and slightly angled to the side. I stared up at my tutor, a newfound respect for the man, as he stared down at me.

"Never forget who you are, Rory. Never forget what you mean to this town."

I calmly walked back to the car after my lesson was over, Mistress Caitlyn noticing the change in my demeanor. Smirking, she watched as I silently sat properly in the car, blushing as she said what a proper young lady I was being.

Back home, she helped me out of my uniform, leaving me in my garter and stockings. My poor clit was leaking uncontrollably, my desperation manifesting physically before her eyes.

Grinning, she pushed me to the bed, grinding on top of me, her tongue mixed with mine. I moaned, ass pulsing around my plug, succumbing to her touches. Brushing hair out of my face, she stared intently down at me.

"Mr. Amadi's job is to teach you how to be a good girl, and he does it well." Mistress Caitlyn's smirk returned, her cock sliding effortlessly inside of me. I groaned, unable to hold up to the lessons I had just learned about serving, instantly cumming hard from her vigorous fucking. My mind on fire, barely able to breathe, I stared up at my Mistress as she continued to push me through my orgasm onwards to another.

"My job, dear little sissy, is to teach you how to be a bad one." Bending down, Mistress Caitlyn forcefully whispered in my ear. "And you'll find I am quite eager to teach you." Those beautiful, cunning eyes gripping me, holding every aspect of my attention, I moaned as her cock consumed me once more. Cumming hard in her arms, my entire body quivering with a desperate need for my Mistress, I knew which lesson I preferred.

Over the next few weeks, Mr. Amadi's latest lesson really resonated with me. I began to see what being the Town Sissy to Great Oaks truly meant, and how important it was to some of the residents. Sure, for some I was just a silly girl, curtsying around town as I chased the heels of Officer Caitlyn. But to others I was a local celebrity, a stress relief, a representation of the close-knit, special community I found myself at the center of.

Regardless of the slutty or humiliating outfits I was forced into, I walked with elegance. Regardless how many times I found myself on my knees around town, from back rooms to personal homes, I thanked each person for being allowed to serve them. Regardless of how wonderful it felt to be fucked, the often vigorous and energetic person behind me pumping frustrations into my little ass, I resisted focusing on how desperate I was to cum.

I was a good girl. I was a good sissy.

However, true to her word, Mistress Caitlyn tested my new found resolve. Terrified, I ran nervous hands up and down my legs, opaque black nylons covering me completely. Hugging my waist, a snug built-in corset giving me a delicious shape, I reveled in the bunny outfit chosen for the evening. Hot pink, the hottest pink I had ever seen, a thin coverage of transparent fabric helping to hide my fake breasts. Ears and heels matched perfectly, my ass pushed up deliciously, a cute white cottontail moving with each shake, bringing a giggle to my lips.

I even had the official cuffs and collar! A proper bunny from head to toe. I tried to keep my imagination grounded, but I couldn't help but get swept up in the excitement of this outfit. Easily my favourite, by a far margin, always pushing me furthest towards that submissive, feminine side of myself. I twirled, a large smile permanently on my face, walking up and down the hallway as I stared down at myself. I was so happy.

Mistress Caitlyn watched it all, smirking as she witnessed me fall further into that slutty persona she knew and loved. And tonight, her adorably excitable sissy would very much need it.

Looking up, seeing that all-knowing grin staring back at me, I blushed deeply, my heels clicking on the hardwood as I presented before my Mistress. Her hands found my waist, gripping and pulling me into her, whimpering as I fell into her arms.

"Are you ready, Rory?" Mistress Caitlyn asked me. I squirmed, whining at her.

"You still haven't told me where we're going!" Pouting, arms crossed under my breasts, she simply laughed in response. The only answer I was getting apparently, soon led outside to her cruiser. I shifted my thighs back and forth, the sensation of my nylons forcing my poor clit to strain underneath the multiple layers. I sighed at the small wet spot beginning to form between my legs, knowing I wouldn't be able to control it through the evening.

We arrived at Hank's, the 'best (only) bar in town'. The bar I often found myself tied up in the basement of. Cheers and whistles erupted as we walked in, blushing furiously at all the comments on my outfit, unable to meet the eyes of anyone there. Mistress Caitlyn walked me around the entire room, showing off the pink sissy bunny, fighting my inner desire to moan like a little whore as hands explored my body.

Carefully walking downstairs in my heels, I scrunched my face in confusion, seeing a new addition to Hank's basement. Behind the pole and bar I normally found myself attached to for nights like this, was a solid black booth. My clit ached, realising just what Mistress Caitlyn has signed me up for, knowing this had to be a gloryhole of some kind. Seeing my recognition, she winked at me, flicking a light switch on the wall. I gasped.

The left side lit up, bright lights illuminating a pink wall,Rory bedazzled on the wall, glittering brilliantly. I whimpered as she led me inside, kneeling down on the soft pillow, noticing immediately that the wall before me was a giant mirror. Staring back at me was my sissy self, an awestruck pink bunny, on her knees in anticipation, slightly overwhelmed at all these new developments.