The Town Sissy Pt. 03

Part 3: Anniversary

It had been a week since my little journey at Mayor Sophia's party, the unofficialunveiling of the Town Sissy. If there had been anyone in town that didn't know about me before, they did now. Bunch of gossipers! Each day a new face and name teased me, emboldened by my adventures around town, and the knowledge of how I was used that night. I kept a permanent blush on my face walking into town, glaring back at the laughs and smiles.

Jon was by FAR the worst, always smirking as we walked past one another during the day. He even had me wear the pink outfit from that night for work one shift! I never thought I'd be changing bedsheets, praying for my maids dress and corset. For a week I'd march up to his bedroom, fuming at this treatment, only to be quickly melted into a puddle of ecstasy at the end of his cock.

I just couldn't win...

Officer Caitlyn and I continued our little walks into town, introducing me to more of the local business owners. Usually our trip always started at the bakery, Darlene and Glen eagerly waiting to drag me into the back. Two gentle, old souls, charmingly encouraging me while I made them both cum. It was always so heartwarming to see the couple embrace and kiss, trapped between them on my knees.

Sitting in my room, I sat on my bed exhausted after a week of being paraded around. The town seemed to come alive, as if it had been waiting for a new Town Sissy. I certainly wasn't used to this level of attention, even if it was such a wonderful mix of heartfelt, exciting, and positive. My clit was snugly wrapped in a pair of light blue panties, wearing a tight pink top sporting the phrase,I left my boobs in another shirt...My keyholder had a terrible sense of humour.

One whole month. I couldn't believe it had already been that long, seeming like only yesterday I had been minding my own business before being pulled in front of a judge. My clit, outlined perfectly in panties, pulsed at the thought, a physical reminder of my captivity. This was easily the longest I'd ever worn a cage, even if I let myself have breaks! Chastity by yourself was difficult, even knowing how much you enjoy it, crave it, and the mindset it puts you in the longer you stay denied.

Turns out, it's much easier when it isn't your choice.

A month where I could count the amount of times I had been unlocked on one hand, teased relentlessly each time, not even able to touch my own cock. Having a tiny little caged clit was so normal to me now, the aching feeling between my legs a constant in my life. Harness around my waist, straining against it with every exciting thought, whimpering as I watch it leak with frustration, only cumming from being fucked. How long would it be until I started to forget what a "real" orgasm felt like?

Feeling the bed shift, the beautiful face of my keyholder brought me out of my reflection. Officer Caitlyn placed a finger under my chin, demanding every inch of my attention without a single word. Smiling, her thumb tracing over my lips, I whimpered as she leaned in to kiss me. My mind fogged over, happily falling easily under her control, moaning as her touch became more forceful. An assertive but gentle grip on my throat, she pulled away, staring at the sissy under her control.

"What was my good girl thinking about?" Those big eyes locking onto me, stealing the ability to speak, I could only softly moan, wishing she'd kiss me once more. But Officer Caitlyn pressed, the stern look demanding an answer to her question. I told her about everything, the doubts and revelations I had been thinking about.

"Mmmmmm, yes. It is indeed a one month anniversary of you coming to Great Oaks, isn't it? How exciting." Officer Caitlyn smirked, pulling a package from the floor. "If only I had thought about that..."

Eyes wide, I giggled as she handed me the box. Opening it slowly, I gasped as I saw the collar inside. Sleek black leather, soft material sewn on the inside. It felt sturdy in my hands as I pulled it out, the ring on the front heavy steel. Officer Caitlyn smiled, motioning for me to turn around. I whimpered slightly as I felt the material tighten around my throat, comfortably sitting against my skin. A perfect fit, the clasp at the back clicking shut with its own built-in lock, my clitty strained as I ran my hands over it.

"There we go, it looks even better than I thought it would on you, Rory." Blushing, I thanked my keyholder, unable to stop running my fingers over every inch. Smiling, Officer Caitlyn pulled me close to her, a finger gripping the ring of my collar. "I'm glad you like it, baby girl." She left another kiss on my lips, floating a little while I was undressed. In a slight daze, I felt myself being helped into some pink lingerie, garters and stockings encasing my legs. Clit and ass left exposed, she gently tightened the transparent top around my waist.

With a determination in her eyes, Officer Caitlyn was far from finished, pulling out a thick bundle of rope. Soon I found myself tied tightly, arms stuck behind me, ankles secured to my thighs. Happy with my predicament, I felt encouraging spanks on my exposed butt, making me growl and giggle at my captor. Turning me over, soon face to face, feeling her strong naked body against mine, I once more fell into my submissive self.

Tracing a finger along the side of my face, her other hand rubbing and playing with my caged clit, Officer Caitlyn watched as I moaned, feeling the urgent need starting to rise inside her sissy. Smiling, staring right into my eyes, she informed me that the new collar came with a cost. A symbol of ownership, of control. While I may be the Town Sissy, in service to Great Oaks however it shall need me, I would obey first and foremost her. My keyholder. My protector. My chaperone. My lawful guide. My constant tormentor.

"Your Mistress." Her lips whispered that word into my ear, a soft kiss sealing it inside of my head. Moaning, her hands teasing my poor aching clit, straining desperately to cum. Staring up at the most beautiful woman in the world, her eyes locked onto mine, I was helpless to do anything but nod, knowing even after a single month, I wanted nothing more. Pushing me down, she placed her pussy right near my lips, asking me who she was.

"Mistress Caitlyn." I barely got the words out of my mouth before she pressed down, moaning as her pussy grinded against my tongue. Each time she lifted up so I could breathe, my Mistress had me repeat it, again and again. Never letting her eyes leave mine, she growled with each orgasm, leaving me gasping for breath, demanding those words from my mouth with each precious break. I was here for her, and here to be used.

Exhausted, my newly minted Mistress slid down to rest on top of me, hand returning to my now leaking clit. Out of breath, I whimpered with need, straining the entire time she had used me. Smiling, she simply played with my clit and balls, rubbing and teasing while I whimpered in her arms, softly begging to cum.

"Beg me," the sternness in her voice returned, the determined look in her eyes solidified. "Beg me my little sissy. Beg me to fuck you."

I moaned, my clit nearly exploding from hearing her talk like that. "Please Mistress! Please...Please fuck me." Over and over, I begged, whimpered, and pleaded. Through it all she rubbed my clit, listening intently, ushering me on with no indication for me to stop. Her hand sliding down to my plug, she made it pulse with her fingers, ever so slightly pushing on my prostate. Smiling, she watched as I slowly lost the ability to speak, mumbling as I felt the familiar tingling in my clit, trying desperately to cum.

Mistress Caitlyn's hands returning to my clit, she gently patted my balls, calling me a good girl. Leaving me on the edge of the bed, I shifted and groaned in my binds, watching as my Mistress slid her cock up those strong, powerful thighs, straps tightened in place. Soon she straddled my tied legs, rubbing her cock all over my caged little clit, smirking at the distinct difference.

She climbed on the bed, and I was soon flipped on my knees, face buried in the mattress. Ass high in the air, I let out a muffled scream as I felt the plug leave my ass, brimming with anticipation and need. I shivered as she teased her cock up and down my exposed hole, needing it inside of me. Placing her foot on my head, pushed even further down, I moaned as my Mistress fulfilled my begging wish, and slid her cock inside of me.

Hard.

Holding my hips, calling me her little slut, Mistress Caitlyn pounded my eager little ass. In and out, I felt her slam into me with each thrust, shaking as my clit tingled and strained in its cage, ready to cum in the only way it was allowed. But she stopped quickly, bringing me to the edge of the bed, staring into my excited eyes as she continued to fuck the desperate need out of her sissy. Tied, helpless, fully under her control, I succumbed to the effects of her cock, her bondage, her outfit, and her collar.

I tried to scream as I finally came, but it soundlessly escaped me. Mouth open, I quivered as Mistress bottomed out in me, holding tight as my clit pulsed and leaked cum. Barely able to stay conscious, I finally sucked in what air I could, breathing heavily as I came down from the unbelievably intense orgasm. My new Mistress smiled, staring down the entire time, watching the fruits of her labour.

After I stopped squirming, she continued slowly fucking my still eager little hole, forcing tiny moans out of me with each thrust. I felt her rub my cum over my lips, sucking on the rest off her finger, tasting the orgasm she fucked out of me. Leaning down, she kissed me in her arms, making out passionately as she picked up the pace once more. Wrapped in her embrace, I came again staring into the beautiful eyes of my Mistress, never wanting this moment to end.

However eventually we both collapsed, Mistress untying me slowly with one hand while we cuddled against one another, spent and both a complete mess of sweat and cum. I rested my head on her chest, listening to her heartbeat starting to slow after the excitement. Once again she ran a finger along my clit, spreading cum across my lips. Staring down at me in her arms, she caressed my face.

"My good girl." I blushed, unable to take my eyes off of her. Smiling, Mistress Caitlyn continued to run her fingers over me. "You'll wear that collar all the time now, even when I'm not here. Every weekend I will be picking you up to bring to my place. You're still going to be working here at the inn, but eventually it will be part-time as Jon won't need as much help." That stern, intense look returned to her eyes, my poor tired clit pulsing under that powerful glare.

"Yes, Mistress Caitlyn."

Her smile returned, staring down at me. "I will simply never tire of hearing you call me that."

That week was fairly uneventful, aside from my usual duties for Gregory and Jon. I knew from being fucked and used as much as I was, that I'd have a VERY hard time going back now. Sex as a sissy was just so...addicting, enticing, and mind melting. Feeling someone's cock slowly slide inside of you, regardless of what hole they choose, just seems to feel right. As if this is how my body was designed to receive and give pleasure. Often I found myself staring down at my clit, silently hoping it never was used ever again...

The only excitement that took my mind of Mistress Caitlyn and her devious weekend promise was my trip to the local bar, Hank's. It was about as typical as you could imagine a small town bar being, having regulars, a small central room, old wooden tables, and of course your scruffy mysterious bartender. Dressed in a ridiculous tiny pair of shorts, my clit perfectly outlined in them, a matching black crop top holding my fake breasts in place. Black stockings and heels, my collar, and a sill amount of eye shadow and mascara, I followed patiently behind my Mistress as I was led into the bar.

Mistress Caitlyn smiled, waving to Hank as she tugged my leash to bring me into the basement. Dark, slightly cold, and what looked to be a storage room, I blushed as I saw my Mistress wordlessly hold out her hand. Slowly, I peeled my tiny shorts down my legs, handing them to her, my clitty already straining from being exposed in public, unsure what was in store for me. No questions were answered as she placed my hands on the wall, my plug replaced by a large vibrator, tiny whimpers of fear starting to escape me.

Another inevitable tug, I gently sat down, feeling the toy in my ass push up as I hit the ground. Moaning like a little whore, my clitty leaked slightly as it settled against my g-spot, desperately wishing it was on. Legs spread, I watched as she cuffed me to a low bar, similar ones for my wrists right in front of me. Exposed, bound, and only a little excited, I looked up at Mistress Caitlyn's smile, that devious excited look in her eyes, caressing my cheek as she stared down at me.

Wiggling her phone at me, I moaned as the vibrator turned on, a low humming that instantly drew all my attention. My hands stolen from me, forced down and stretched as far as I could be, there was no escaping whatever torment she'd planned for me. A kiss on my cheek, a sassy little wink, and Mistress Caitlyn was gone, back upstairs to the bar. I whimpered after her, but I knew that this was going to be a long night.

It didn't take long for the first patron to come down, a woman named Monica I hadn't met before. Moaning from the vibrations coursing through me, my poor eager hole clinging desperately to it for a chance to cum, I stuck out my tongue for her to grind on. Moving her clit back and forth, her hands firmly in my hair, she groaned using me for her pleasure. I stared up, watching as she pushed hard against my mouth, cumming on shaky legs. Seeing her cum I pouted, wanting my own orgasm, the vibrations too low to bring me to the edge.

Slightly out of breath, Monica patted my cheek as a thank you, replaced quickly by a man named Doug. I didn't get a chance to learn much about him, moaning like a little slut as I kissed his balls, getting him excited and ready to use my throat. Teary eyed, relaxing my throat as best I could, I listened to his sigh of relief as cum flooded into my mouth. He watched me swallow, the wordsgood little sissy echoing in my mind after he left, my poor clit desperately trying to break free from my little pink cage.

Person after person made their way down into that basement, finding a use for the tied up horny sissy. After each cock or pussy I felt my desperation grow, eager for my own orgasm after providing so many theirs. Mistress Caitlyn came down from time to time to check on me, teasingly turning the vibrator up and down, snapping pictures and videos. But, she always left me aching to cum, whimpering and pleading for her to turn up the vibrations.

When I finally felt my cuffs being unlocked, I was a complete mess. My pretty mascara was ruined, halfway down my face. Cum and spit covered my little t-shirt, evidence of the evening I had had. Mistress Caitlyn smiled, enjoying the sight of her sissy, those amazing hands of hers gently rubbing my balls, coated in my own pre-cum. Helping me stand and stretch, she replaced my plug, whimpering softly from the vibrator leaving me, still hoping she'd let me cum. Sliding my shorts back on, clit snugly held in place once more, I was led out through a much busier crown than when we walked in, cheers and whistles following us while I tried my very best to die of embarrassment.

Mistress Caitlyn walked me back to my room, cleaning me up while I stood in place, my mind currently held hostage by the aching need I felt in my clit, the urge to cum brimming through my entire body. But she helped me into a silky pink nightie, kissing me on the cheek with a promise to pick me up tomorrow night. I whimpered, staring into her eyes, that knowing look spread across her face, leaving me with a final wink and laugh.

Left in a state of arousal, a straining clit, pulsing my ass around my plug, I tossed and turned all night, unable to sleep as I ran my hands up and down my body, a silly desperate little sissy. As I "woke" up on Friday I groaned, feeling exhausted and drained. All day cleaning and folding I could barely focus, my poor clit stealing my attention. I even found some guests to distract myself with, draining them of all the cum they had for me. But nothing could take my mind off the desperate need I felt inside of me, the desire to cum and be a good girl for my Mistress.

Friday night I showered after work, quickly getting ready in a sparkly pink dress Jon had bought me. I'd worn it a few evenings in the lounge entertaining some of the guests and locals, and I loved it. Skin tight, with a cute little window underneath my breasts, it hugged my body perfectly in every place. Long sleeves, the shoulders poofed just enough to make me feel silly and girly, coming down mid-thigh. Matching heels, beige nylons, and of course my new collar, my outfit was complete. One last look in the mirror made me blush, my clit pulsing lightly as I left to wait outside for my Mistress.

Mistress Caitlyn arrived, smiling as she got out of the car. Taking my hand, she complimented how pretty I looked, beaming from her praise. After helping me inside, we were quickly off, arriving at her small home just outside of the town. My heart fluttered with each step, my heels clicking on her pathway as we headed to the door. Ushered inside, I took in the sight of her place, softly moaning as her hands enveloped me from behind.

Squeezing and feeling wherever she wished, Mistress Caitlyn soon had me kneeling in front of her, sucking on her thumb as I stared up at my keyholder. Smiling down at her sissy, she leaned in to whisper ever-so-softly into my ear.

"Welcome home, Rory."