The Town Sissy Pt. 02

Part Two: The Party

Groaning, I woke up exhausted. My impossibly small pink clit screamed at me in its prison, straining away to the memory of Officer Caitlyn's wonderful strap-on. A part of me still didn't believe it had all fit, while a bigger part was so glad that it did. I had of course played with my ass many times in the past, quickly becoming one of my favourite ways to cum. But nothing compared to being fucked like that, being completely controlled and dominated, thrusted into the mattress while one of the most amazing women I had ever met forced orgasms out of my body. As much as I pouted, feeling the cage between my legs harnessing my freedom, the smile spread across my face made it hard to pretend I didn't love it.

Wig snugly in place, my uniform properly donned, I skipped out of my room to start the day. The inn never seemed to be too busy, always a few guests, but nothing I couldn't handle. I had in the past of course done the whole maids outfit to clean my own apartment, constantly imagining scenarios and fantasies. In reality, however, it was mostly just cleaning. Changing sheets, new pillows, vacuum, and the signature mint on each pillow. Although it certainly helped wearing tights and a cute outfit while doing so!

The guests as well were always so nice, thankfully. Some teased me about my uniform, smiling at the blush they could force onto my face. Most simply left me to my chores, asking for this and that, which I was always happy to do. My petticoats swishing as I moved, nylon legs rubbing together, heels clicking off the hardwood floor, I spent each day in my own girly heaven. Even the most mundane tasks I was more than happy to do as long as I got to be a sissy.

Humming to myself, I headed over to Gregory's cabin. Hearing the mower somewhere behind the inn, I knew he'd be a little while before returning, so I began tidying up. He wasn't really too messy (although he couldn't rinse a dish to save his life!), so I had the little cabin cleaned up in no time. Stretching, I took off my dishwashing gloves, my sore muscles enjoying the tension release.

I looked around outside, poking my head through the window, but couldn't see Gregory anywhere. I should have been content to just wait for him, kneeling in front of his bedroom door to await my weekly 'chore' of cleaning his big cock. But, I was curious what else he had in that room of his, the secret treasure trove of toys and gear. Giggling, a mischievous streak ran through my body, knowing he had told me not to go in there without him.

Clitty straining in my cute pink cage, a devilish smirk on my face, I did anyway.

I found his box of debauchery, neatly organised and packed away. Rope, cuffs, gags, as well as a plethora of toys. My eyes widened with excitement seeing all the plugs and vibrators in there! Why on earth did Gregory have all this?

My curiosity had deafened my ears, squeaking as a set of strong, firm hands gripped my arms. Pinned against his chest, I wilted hearing the growl behind me, Gregory's hot breath on my ear.

"I thought I told you never to come in here without me, sissy girl." That stern tone seemed to vibrate through my entire body, making me shiver from the effect his strong control was having over me.

"I, uh, forgot?" He responded with a disappointed grunt, making me giggle. Brought to the bed, he threw me down, quickly binding my arms behind my back. Holding each elbow from behind, the rope harnessed across my chest, comfortable but firm. I made the effort to squirm, but I knew I was trapped until he said otherwise. My ankles were next, rope looped under my heels to keep them in place. Thighs as well were soon stuck together, wiggling around like a worm as he left me on the bed.

A strong, rough hand forced my mouth open soon after, quickly shoving a ball gag passed my lips. I growled, feeling it against my tongue as he buckled it behind me. Satisfied with the state he had left me in, those intense eyes stared down at me, gripping my throat to hold me in place.

"You are going to learn to respect my wishes, Rory. Whether you want to or not." Eyes wide with excitement, I couldn't stop a muffled giggle leaving my throat. Whatever punishment he had in store for me, that certainly wouldn't help my case. But sometimes, no matter the cost, you just have to be a brat, you know?

Well the cost was revealed to me soon enough, pulled over his lap, my dress and petticoats lifted out of the way. The first spank took me by surprise, a slight sting in my cheek as I squealed. After five more my squeals morphed into a mix of moans and whimpers, my body fighting itself whether it hated or loved being treated this way. Gregory took breaks between spanks to rub my ass and legs, enjoying the control he had over a vulnerable and excited sissy.

Soon my tights were pulled down, exposing the cute panties I had chosen to wear today. His spanks were harder on my mostly bare skin, my moans chased away by a chorus of whimpers and tears. Ass and thighs burning from the constant assault, my brattiness and sass had promptly left me, leaving a begging, docile maid. I was a mess of emotions, jumping from the stinging in my cheeks, to the aching desire every time he touched my plug, or ran his hands over my legs. Grabbing my throat, Gregory placed me on my knees in front of him, removing the gag to hear my sniffles.

"Are you ready to behave, Rory?" I eagerly nodded, not knowing if I could take another spank to my sore ass, stinging intensely behind me. My clit, however, happily leaked away from being treated so roughly. Being a sissy sometimes was very confusing. For now though, as I watched Gregory unzip his jeans, all I wanted was to be his good girl. Arms still bound, he left me to bob up and down on his cock, devotedly focused on my new task.

Working hard, pushing down until my nose tickled against his stomach, I gagged trying to breathe around his cock. Gregory groaned, his hands finding the sides of my head to keep me in place, soon pushing in and out of my mouth. I stared up, eyes wide, taking breaths where I could while he used me, controlled me. Feeling his cock slide along my tongue was heaven, and I desperately wanted to taste his cum. After Gregory's punishment, I wanted nothing more than to hear him call me his good girl. His good sissy.

Another groan, his grip tightening around me, I whined as Gregory's cock slid all the way into my mouth. My air supply was quickly replaced with cum, shot after shot seeming to be pumped directly into my stomach. Eyes watering, staring up at my captor, I waited until he finished, the final shiver and pump, slowly pulling out of my cum covered mouth. Gasping for air, choking on the delicious coating I could taste everywhere, I whimpered from the straining clit between my legs. Apparently I enjoyed being used like that.

A lot.

A content sigh, Gregory left me to clean off his cock, staring down at the eager maid between his legs. Satisfied with my work, once again I whimpered as his strong grip held my throat.

"I will happily punish you in the future, sissy. You don't need to misbehave to have fun, you merely have to ask." My eyes wide, lost in my own subspace, I could only nod. That intense stare never left me, drinking in my every movement.

"No more snooping. Next week I want to find you kneeling in front of my door, waiting patiently. Do you understand me, Rory." I softly whined, wanting to argue or be my adorable bratty self. But Gregory had won, had promptly spanked out all of my resistance. I sighed, nodding, promising to behave in the future. The smallest of smirks spread across his face, as if it was the only way he was capable of smiling, bending down to kiss me. Tiny little noises escaped my lips while he did so, not expecting him to be so comforting.

"Good girl."

I beamed as he untied me, straightening my outfit and tights. With a final, friendly spank, earning a glare from me, I was sent off back to the inn. After cleaning up, re-doing my ruined make-up, I headed off to dinner. Tonight a plate of roasted chicken and vegetables cost me two blowjobs, the cooks were more than happy to have me under the table while they worked. Between them and Gregory, I ate with the taste of cum coating my mouth and tongue.

That night as per my new tradition, I snuck up to Jon's room, my ass pulsing around my plug in anticipation. Officer Caitlyn may have asked me to take care of a charming, caring, lonely, wonderful man, but I'd be lying if I said I didn't enjoy doing so. The aggressive grip on my waist, the hard thrusts as he fucked my eager little hole, the gentle kisses along my back after I was filled with cum, and of course the mess my own clitty made every time he was inside of me. Yes, I was settling comfortably into the new role I had been forced into.

Butterfly Inn Sissy Maid. Great Oaks Town Sissy. Officer Caitlyn's Personal Slut. Okay, that last one I named myself, but it still fit! To me, it didn't matter what title I was given, I just wanted to be a good girl.

A few days later, I entered the lounge for dinner in a pretty pink dress Jon had bought for me. A cute floral pattern throughout, hugging my waist snugly, flaring out enough for me to twirl like a goof. Matching it with opaque pink tights, I smiled and giggled the entire time getting ready, patiently waiting for dinner. Lost in my own mind, I flinched with surprise as Mayor Sophia calmly sat across from me.

"Why, hello Rory." Beautiful, determined eyes stared me down through dark rimmed glasses. Straight black hair hanging down over her white blouse, professionally tight light blue slacks hugging her strong legs. I had about four lumps caught in my throat seeing the confident, gorgeous woman suddenly holding my every attention.

Mayor Sophia smiled, seeing the effect she was having over me. "What a pretty dress, perfect for a sissy like you." I blushed. Hard. Unable to speak properly, I murmured some sort of thank you. However she seemed on a warpath to torment me, soon ordering me up to twirl around, showing her every inch of my outfit. As I curtsied in front of her, my poor clit strained in its little prison, desperate for some attention.

Grinning, Mayor Sophia motioned for me to sit, the bartender Chris bringing her a drink. I promptly pretended not to see him, knowing how silly and red my face looked at the moment. Still watching my embarrassment, she urged me to eat as my food arrived.

"Rory, I'd like to extend an invitation to you for this weekend. You see, I often enjoy hosting parties for friends and colleagues. Nothing too fancy, mostly just drinks and entertainment." I whimpered as she talked, her foot finding my nylon legs, rubbing up and down as she continued.

"I could really use your help with ensuring the party runs smoothly, mostly serving drinks and food." Her foot ran further and further up my legs, no longer able to focus on eating. "And of course, with entertainment. I must say, there are many people in and out of town who are just dying to meet you." I moaned as she slowly rubbed my clit, gripping the table for support.

"What do you say my dear, would you be willing to help me out?" Never taking her eyes off me, that knowing smirk on her face. "I promise to make it worth your while. Just wait until you see the outfit I have planned for you, little sissy." I whimpered, ears perking up at the mention of an outfit.

"W-What is it?" I asked, trying not to openly moan, desperately failing at ignoring the straining between my legs. Mayor Sophia responded with a tut, shaking her head with a smile.

"Oh, that is a surprise I'm afraid, my delightfully sweet little thing. You will find out when you arrive." I groaned, barely able to think, the effects of her playful teasing melting my brain just a little. We both knew I would say yes, it was only a matter of time. I nodded, legs shaking as I felt my clit nearing an orgasm.

"Excellent!" Mayor Sophia cheered, her foot quickly leaving me a tormented, drained mess. Standing beside the table, she bent down to kiss my forehead. "I will have you picked up Saturday night. Thank you Rory, I promise a fun and unforgettable evening."

Just like that, she was gone, unable to stop myself watching her go. Why were confident, powerful women so hard to ignore!? I couldn't even think around her, how was I going to help at her party...

And what outfit did she have planned!!!?

My clit ached all through dinner, groaning as I collapsed onto my bed. I tried to read, keeping my mind off the evening conversation, but to no avail. I was rewarded with a night of fantasies and desires, multiple situations continuously running through my head. Whimpering, I pulsed my aching little hole around my plug, wishing Officer Caitlyn or Jon were there to fuck the thoughts out of my head.

Waking up in the morning, one of my wishes came true. I moaned softly as a gentle hand brushed through my hair, lazily opening one eye to see Officer Caitlyn smiling down at me.

"What a tired, frustrated sissy! Did a visitor last night get you all worked up?" I pouted, knowing full well she already knew the answer to that question. Letting out a grumpy groan, I shuffled closer to my keyholder, head in her lap as she pet me.

"My poor girl. Don't you worry, today we're going to get you ready for the party tomorrow. You're going to love it Rory." Officer Caitlyn continued her soft touch, feeling me melt into her. Placing a finger underneath my chin, she brought me up on my knees, tenderly kissing my lips. My brain barely worked in the morning anyway, but after the treatment I was receiving from this beautiful Goddess, I was a submissive mess.

Officer Caitlyn gripped my arms firmly, guiding me down onto the bed. Standing, she quickly removed her uniform, climbing back on top to replace her lips on mine. Unable to contain my moans or excitement, I grinded my clit against hers, whimpering with each breath. She returned my moans enthuisiastically, rubbing her panties back and forth over my cage, hand gripping my hair firmly as we made out.

Pulling up, a wild look in her eyes, Officer Caitlyn removed the now soaked panties, pulling me down to sit her perfect pussy on my lips. My clit strained, pulsing uncontrollably from being ignored, but I happily dove into my new task, licking and sucking hard as she grinded on my face. Knees holding my arms in place, she moaned in control, delightfully using the sissy underneath her for pleasure.

It didn't take long for my beautiful keyholder to shake and quiver, cumming on my tongue. However, she was far from done, gripping my hair even more as she continued to grind hard on my face. I can't tell you how frustrating it is to watch someone cum while you are caged, clit trapped away from doing exactly that. Yet, despite my desire to be released, to feel that powerful orgasm shoot out of me, that pent up need...underneath Officer Caitlyn was exactly what I wanted. Exactly where I needed to be.

Out of breath, both covered in sweat, she finally collapsed on top of me, an exhausted smile plastered on her face. Laughing at the obvious desire in my eyes, Officer Caitlyn gently cupped my clit, feeling the heat and strain between my legs. I made every conceivable noise in my arsenal to entice her to play with it, but she simply rubbed, giving my poor full balls the odd spank. I still didn't know how she simultaneously made me wish to be locked and unlocked. Wanting to cum, yet wanting to be her caged little sissy forever.

Tying my arms to the headboard, I finally sighed with relief as she unlocked me. My cock instantly sprang to life, eager to be free and erect, pulsing with desperation. Ignoring the constant noises coming from my mouth, Officer Caitlyn knowingly stared into my desperate eyes, cleaning and shaving what she rightfully owned. Gentle, tender, and ever careful, I moaned through the frustrated process, desperately wanting the release I had been denied for weeks.

Officer Caitlyn smiled through it all, always glancing up at the frustrated sissy in her clutches while she worked. Content, she settled into tantalisingly slow, teasing strokes. My cock lubed, aching, pulsing, and desperate, trembling in her hands. Never relenting, but neither changing speed, she was content in keeping me in limbo, not quite edging but neither allowing me reprieve. Constantly waiting for an orgasm that would never come, but the hope that it might demanding every spec of my attention.

I didn't know how long she teased my unlocked cock for, but I almost cried with relief when I felt my cage snap back into place. The familiar tightness was now more common than being free for me, as was the aching I felt in my balls. Whimpering, Officer Caitlyn leaned down to kiss me deeply once more, her beautiful voice ringing in my ears as she called me her good girl. I'd suffer through anything to hear those two words from her.

Snapped out of my submissive daze, we both showered off the morning activity. Officer Caitlyn giggled as she soaped me down, my uncontrollable moans from being touched always amusing her. Cleaned, inside and out, she replaced my plug before sliding up a pair of cute late pink panties. I sat down to do my make-up, watching in the mirror as she donned her uniform, clitty straining from the show.

My own 'uniform' today was a pair of tight jeans, hugging my ass perfectly, as well as clearly outlining my clit. When I tried to protest it earned me a slap on my new second skin, blushing at the thought of being paraded around in these. My breast forms were placed in a matching pink bra to complete my panty set, covered with a simple black top. I slid some pink sneakers onto my feet, face deep red as Officer Caitlyn placed two pink bows in my wig, smiling at the completion of the outfit.

Taking my hand, no word of where I was being led, I followed dutifully to her car, eyes wide as we drove to the center of town. This was the first time I had left the inn since my sentencing, starting to settle into a happy comfortability being a sissy maid. But in public? Under the watchful eye of all these people? I was only a little terrified. Yet, as Officer Caitlyn took my hand, squeezing it for support, I took a deep breath and resolved to follow whatever plan she had for me.

I blushed through every greeting, every friendly wave from across the street, every interaction Officer Caitlyn dragged me through. Couples, shop owners, friends, everyone in town knew exactly who I was, and my role in their little society. A few people reinforced this, casually running hands over my legs and clit, complimenting how cute I looked. A smile was permanently stuck on my face while I blushed away, so happy with all the positive attention.

My keyholder smirked, seeing the effect being in public was having on me, the realisation of what it meant to be the Town Sissy starting to take hold. I wasn't just property of her, Jon, Gregory, or The Butterfly Inn. My purpose was to serve the town, in whatever capacity I was needed, to whichever local requested my help. For some that meant showing off my outfit, bending over while they cheered. For others that was letting them feel every inch of me, poor clitty screaming at me through the constant touching.

Walking into the bakery, Officer Caitlyn sat down for a coffee and croissant, watching as I was whisked away to the owner's office. The Stevens, Darlene and Glen, an older couple, gleefully placed me on my knees. I moaned around her clit and his cock, each giving encouragement as I pleased their other half. We left the bakery soon after, Officer Caitlyn with the taste of vanilla, cinnamon, butter, and pastry in her mouth. Refused a refreshment of any kind, I was left with the reminder of cum on my breath.

The Stevens weren't the only people who took advantage of the first public sighting of the new Town Sissy. I found myself on my knees many times throughout the day, a wonderful mix of clits and cocks to suck on. Dominant, assertive, kind, embarrassed, excited; all kinds of people and emotions greeted my services. At first I felt overwhelmed a little, but after a few similar visits I fell into this role as happily as I did being a sissy maid.