A Night Out

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A new dress, a strong Mistress, and a night out on the town!
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RoryRouge
RoryRouge
597 Followers

Struggling to think, my arms shaking with effort to support myself, I could only moan as I felt the cock in my ass slide in and out of me tantalisingly slow. Mistress Carla, my partner and world, smiled behind me as she watched my futile attempts at trying to cum. For years she had enjoyed thrusting her collection of cocks inside of me, and knew exactly how to force an orgasm out of my willing, desperate little hole.

However, it also meant she knew how not to...

I whimpered, wanting to bed and plead with her for an orgasm, but my words couldn't formulate in my mind. Every attentive power I possessed was focused on her cock, her beautifully thick cock, slowly and carefully penetrating me, a gentle rub over my g-spot. I could feel how close I was, the eagerness tingling in the tip of my caged clit, straining against the 3D printed bars that had encased it off and on for years now.

Trapped under her control, feeling those strong and dominant hands grip and rub my ass, I could only moan, succumbing to her power. We both knew how I adored being her toy, her plaything, her pet. How I blushed excitedly every time she called me her good girl. How eager I was to show off for her, regardless of how humiliated I felt. Despite the desperate need for an orgasm I felt surging through my body, I knew deep down that was no longer something I had or wanted control over.

Mistress Carla pushed her cock deep inside of me, feeling her body heat against my ass, shivering as I yet again came so close. She reached between my legs, rubbing my excited clit as I whimpered, feeling the straining and futile attempt it constantly made to escape its pink prison. Satisfied with the state she had fucked me into, Mistress gently pulled out, leaving me on the bed with my ass high in the air, gaping and wishing to be filled once more.

Stripped of her temporary cock, she quickly slid a plug inside of me, sighing as I felt that familiar feeling of fullness return. Leaning against the headboard, she pulled me to her chest, running hands through my hair as I melted into her strong form, trying and failing to ignore my clit. Her wandering hands made that even less possible, as she rubbed and squeezed my cage, bringing glistening fingers to my lips. I was tormented with the taste of the orgasm denied to me once more, greedily sucking her clean as she kept the aching in my clit to a constant pulse.

"Don't worry, baby girl," Mistress Carla said, that soft whisper so close to my ear, "I'll let you cum soon enough. We just need you to be nice and desperate for our date Friday." I blushed, still unable to formulate any words, leaning against her for support. She had been teasing me about a 'surprise' date night, something she held over me about once a month. I always enjoyed being feminine for her to some degree, but nights like these were my favourite.

She'd spend hours getting us both ready, ensuring everything was exactly how she imagined it. Dresses, heels, albeit mine were always far more feminine, Mistress would drag me into all sorts of trouble. Sometimes it was dancing, drinks with friends, even just a games night. One of her favourite pastimes was finding men for me to suck, often holding me in place between her legs, watching as I looked up at both of them, being a good girl. I liked sucking cock well before I met my Mistress, but doing it for her...was on an entirely new level of excitement!

After letting me cool off from her slow, teasing fuck, Mistress gently tapped my nose with one finger. Our little fun sign that she had a need for my tongue, regardless of what I was in the middle of. I could be in the middle of cooking dinner, halfway through watching a hockey game, or even sound asleep, that meddlesome finger would tap away, and I'd instinctively sink to my knees like her good girl.

Still floating in subspace, I giggled as I slowly slid down her body, kissing as I went. Mistress Carla smiled, a happy sigh escaping her lips as she spread her legs slightly, welcoming her good girl in between them, a hand firmly embedded in my hair as my tongue found her clit. Soon I heard her moaning above me, gripping me tightly as I licked and sucked exactly how I had been taught. Like my Mistress, I too knew exactly what she liked, wanted, and needed.

As she came for the first time, shaking as she held me down against her pussy, I moaned along with her. There was something about giving an orgasm to someone who denied your own, to feeling my clit aching at the injustice, watching her breath heavily as she enjoyed what had been teased and stolen from me. Mistress smiled seeing the fire in my eyes below her, the desperation I felt watching her cum, the tightness in my clit as it strained once more.

Sighing contently, she pushed me back down, moaning once more through my licks and sucking, using my tongue to her heart's content. Eventually she relented, breathing heavily as I was pulled up to her chest once more, smiling down at her good girl. I blushed, whimpering as my clit ached desperately watching her cum over and over, listening to her happy praises wash over me.

Mistress gently brushed a hand through my hair, listening to the tiny whimpers of frustration leaving my lips, every so often leaning down to kiss my forehead. I hugged her tightly, finally able to fall asleep in her arms, welcomed by my tormented dreams as I imagined Mistress' big cock forcing every drop of cum I had out of my body.

Waiting for Friday felt like an eternity.

The next night I donned my pink maid outfit, ensuring everything was in place exactly how she wished, mincing my way around the apartment. Mistress watched with hunger in her eyes as I cleaned, barely paying attention to the book resting in her lap. Always one to play, I made sure to give extra care to all the things around her, bending over seductively every chance I could. If she was going to keep me denied, frustrated, and on edge, then I was happily going to be a brat about it!

However all my charade earned me was a place over her lap, replacing the book she had abandoned, a constant mix of moans and cries as she reddened my ass with a sound spanking. At least that night I had something other than the aching strain of my clit to keep me company. But each night leading up to her surprise I was left in the same state, whimpering against her chest as I tried to fall asleep, the need reinforcing itself and building up inside of me.

When Friday finally arrived, we both were a bit giddy getting home from work. Mistress gave me nothing but an apron to cook with, the soft fabric teasing my poor clit as I tried to focus. She was in and out of our room, making preparations, pausing only to wander into the kitchen, pinning me to the counter for a flurry of rubbing, teasing, and kissing. My mind was a fog of sexual energy, wanting nothing more than to be taken by her then and there.

But my torment was not yet over, cleaning up dinner as she disappeared once more. Eventually I was called to the bathroom, sitting me down for my transformation. Mistress gently placed the blonde wig on my head, brushing and setting it to her liking. Bangs brushed my forehead, already feeling myself fall into my more feminine persona, staring up at her longingly as she began applying mascara, lashes, lipstick, blush, and concealer. Mistress Carla wasn't one for make-up, but she adored turning me into her little doll.

Sitting in front of the mirror, the strong arms of the woman I loved carefully holding me still, I had to admit I adored it as well.

As she playfully tickled my nose with the brush for a final time, Mistress moved away so I could see her handiwork in the mirror. I gasped, always amazed at what she could turn me into, far more feminine in my mind than reality. But there I was, her pretty girl for the evening, my hair framing my face perfectly. Each time she did this reveal I had to fight back my tears, not wanting to ruin all her hard work. Mistress carefully cupped my chin, kissing my newly made red lips deeply.

"Are you ready to be my good girl for the evening, Rory?" Eagerly I nodded, enthralled with my lover, owner, Mistress, and partner. She smiled, her eyes showing a mischievous glint, as the rest of my attire had yet to be spoiled. Taking my hand, she led me into our bedroom, soon resting a hand on her shoulder as she slid stockings up my shaved legs, shivering from the sensation. My poor clit was already in wondrous agony, straining desperately as I was turned into the perfect woman for my Mistress.

A corset with built-in garters, one of our collective favourite pieces for me, helped give a more feminine form, as well as keeping my stockings nice and snug. The snug feeling around my waist, the straps digging into my thighs all evening, all of which just enhanced exactly how I wished to feel for my Mistress. She took a few teasing photos of me, forced into poses, never knowing exactly how many people she showed them to.

I moaned as she walked behind me, running her hands up and down my stockings, playfully snapping at my straps. The only consolation to how desperate I felt, was knowing just how eager my Mistress was as well. I could feel it in her touch, the excited energy built up between us, the promise of an unforgettable evening. The desire in her eyes as she stared into mine was intoxicating. With a smirk, she pulled away, moving slowly towards the closet.

With a dramatic reveal (which was mostly her waving her arms in front of the closet like a dork), Mistress Carla pulled out my dress for the evening, and for the second time I gasped in surprise.

I had several dresses she had purchased for nights like this, often tweaking them to fit my bigger form. But this one was new, and I immediately loved it. A flowing black skirt, with multiple tiers showing transparency in the silky fabric, unable to stop myself running a hand up and down it with glee as Mistress held it out for me.

A belt of spandex held the skirt to the top of the dress, a perfect juxtaposition from the gold, glittery top. No sleeves, the neckline coming right to the top, perfect for girls like me who only had access to 'temporary' breasts. I couldn't take my eyes off it, the light bouncing beautifully off of the sparkles and flecks of gold. Mistress giggled seeing my excitement, leaving me to gawk as she fitted my bra and boobs in place, hugging me from behind as they were clipped in place.

"It's...it's beautiful Mistress." I could barely contain my excitement, eager to try it on. Mistress Carla smiled behind me, gently kissing my neck, squeezing my exposed ass as I moaned against her body.

"Just a few more things and then I will let you try it on, baby girl." I whined impatiently at her, but she simply playfully spanked my ass, taking out a pink princess plug and some lube. Gripping my ankles, I bent over as requested, groaning as she effortlessly slid it inside of me, sitting comfortably right against my g-spot. Each step would send jolts of excitement through my body, especially in the heels she planned for me to wear.

Sliding a pair of silky panties up my legs, just barely sliding between my asscheeks, clit now snugly held in place. Satisfied, Mistress held the dress out in front of me to step into, watching me brimming with excitement as it slid up my body, the light fabric of the skirt already teasing my nylon covered legs. Feeling her zip it shut, trapped in for the evening, I couldn't help but giggle, twirling around to see how the skirt flared around me, only to return to its original shape.

I felt like a princess.

Mistress watched my giddy excitement, a giant smile plastered on my face. I playfully pranced up and down our bedroom, unable to stop myself from swishing back and forth. She finally put a stop to my shenanigans, needing to add some matching gold earrings and glittering heels. I squealed with excitement as she slid them on my feet, feeling complete and ready for whatever she had in store for me.

Finished getting me ready, Mistress had me help her into her own dress, a deep red that seemed to hug every part of her. No heels, no nylons, and very little make-up, I whimpered as she finalised her look in the mirror. The dress showed off her strong legs, exposed shoulders and toned arms, leaving me only slightly drooling from the wondrous sight of her.

Walking towards me, placing a hand on my fake breasts, Mistress showed me one final surprise for the evening. Taking my wrist, she calmly wrapped a beautiful thin gold chain around me, clicking the clasp shut. I giggled, gently playing with the tiny lock hanging off of it. She smiled, holding my hand in both of hers.

"I figured you could use a reminder through the evening of your status. You know, as my locked little slut." I rolled my eyes at her, failing to hide my smile.

"I think this dress will make a reminder of my cage unnecessary Mistress!" She smiled, shrugging innocently, her hands never leaving mine. Moving them to my waist, I rested my arms around her neck, feeling beautiful in her arms as she pulled me close. I towered over her in my heels, yet her demeanor always made me feel utterly small, left a submissive mess in her presence.

Mistress gripped me tighter, pulled in and pressed right against her, moaning softly as she stared deeply into my eyes. One hand made its way underneath my chin, gently pulling me down to her lips. She whispered right against my mouth, feeling her hot breath against my skin.

"Are you ready to be my good girl tonight?" I whimpered, pulled in so tightly against her. Staring into those beautiful eyes, the eyes that I could ensure I did whatever she requested, I nodded softly. Smiling, Mistress raised herself up onto her toes, planting a soft gentle kiss on my lips. Left in a daze, I felt her pull me out of the room, out of our apartment, and out into the world.

Walking downtown, our hands entwined, Mistress kept me distracted with humour, knowing how self-conscious and anxious being out as Rory made me feel. As much as I enjoyed it, and knew my Mistress did as well, I was still left feeling like a giant, wishing I could be a tiny, cute girl. Yet, holding hands with the woman I loved, wearing one of the most beautiful dresses I had ever seen, I wouldn't trade this moment with any other in the world.

We arrived at one of our local clubs, clinging to my Mistress for support. Before I could even get my bearing she dragged me to the dance floor, teasing me by pulling on the skirt of my dress. I could only giggle, following her lead and twirling away, feeling my confidence return as she spun me around. The silky fabric flowed around me as I danced, twirled, and moved, reinforcing that feminine persona I loved so much.

The night of dancing continued, with pauses for drinks and conversation. While we caught our breath at a table, sipping down some much needed water, Mistress smiled at a man casually approaching us. Taller than me in heels, I instantly blushed, unable to even look at his bearded, beautiful face.

Damien, as we soon found out, asked Mistress Carla if he could dance with me (COMPLETELY IGNORING ME, RUDE!!), to which she happily agreed to with a laugh. My blush deepened, glaring at them both as he led me back to the dance floor, clit aching immediately as soon as he held my hand. I both hated and loved the effect handsome, confident men had on me!

His arms wrapped around my waist, pulled against his chest, I moaned into the loud music as we grinded together, soon finding my head resting against his chest. Involuntarily my hands moved behind his head, running through that short, coarse hair, my body relenting to his movements. I was swept up in our little moment, losing track of time or how many songs had passed, somewhat shaken as he led me back to my grinning, knowing Mistress.

I chose the mature route of refusing to make eye contact with either of them.

However my attention was drawn as Mistress pulled Damien down to her level, whispering in his ear, those devious eyes never leaving me. I glared back at her, unsure of what plan she was concocting, knowing it would lead to some form of humiliation on my end. Sure enough, the grin spreading across Damien's face confirmed it, finding myself being pulled along by her, with Damien in tow.

Finding what she sought, Mistress pulled the three of us into a hidden dark corner, the muffled music playing in the background. Placing a firm hand on my shoulder, I whimpered as I sank to my knees, knowing what that subtle touch meant. Brushing hair behind my ear, Mistress sent one of her intoxicating whispers coursing through my mind.

"Damien says that you teased him on that dance floor, Rory.Tsk tsk. That isn't nice." I whined, pouting and trying to protest. But she shushed me, running fingers through my wig, her other hand gently wrapping around my throat. "Such a bad girl. I think you owe it to him to fix this situation, don't you baby girl?" I whimpered, staring up at Damien, rubbing his cock through his pants, an excitement glinting in his eyes.

I played along, protesting just a bit more at Mistress Carla, before accepting I had been a 'bad girl', agreeing to pay for my transgressions. After a quick look down the hallway, Mistress nodded to Damien with a smile, watching eagerly as he freed his cock, unsurprisingly hard and ready to be played with. I stared at it hungrily, always enjoying playing with cocks since Mistress locked mine away so many years ago.

With a gentle nudge from behind me, I gripped his beautiful cock with one hand, stroking it up and down to ensure it was ready for my mouth. Moaning, I kissed and sucked on his balls, listening to the groans he emitted mixing with the music. I only lasted a few moments before running my tongue from the base of his cock to the tip, far too excited to have it in my mouth.

I could feel Mistress Carla's excitement behind me, her body pressed hard into mine, resting between her legs. She loved watching me suck cock. Whether it was hers, or a real one, I often found myself in all sorts of positions, with Mistress proudly and happily watching on as I was a good girl. Feeling her support, I eagerly devoured Damien, quickly feeling his pubic hair tickling my nose.

"Fuck me, wow." Damien exclaimed, smiling in shock as I took all of him in my mouth. I continued to service his wonderful cock, listening to Mistress laugh with pride behind me.

"Yes, my Rory is quite the slut. I am very proud of her." Damien groaned hearing this, feeling his cock harden even further inside of me. One hand gently cupping and rubbing his balls, I sucked him as deep as I could, desperately wanting his cum swirling around my tongue. He groaned, tensing up as I refused to relent, Mistress holding my head firmly still with two hands.

Damien groaned, tensing and twitching, as I bobbed my head up and down his shaft. I giggled in surprise as I felt the first spurt of cum make its way into my mouth, not slowing my devotion to his cock in the slightest. I listened with pride as he groaned, cock twitching with each jet of cum leaving his body, soon left empty and sensitive as I moved my lips back to the tip, trying to lick and suck every drop he had for me.

He finally shuddered, pulling away as I giggled, now proudly holding a mouth full of cum. I stared up, locking eyes with my Mistress, that proud look on her face. She smiled down at me, offering a gentle nod, watching as I dutifully swallowed all of his cum, showing her and Damien a clean, empty, and happy tongue.

"That was fucking amazing." Damien smiled, moaning from being over stimulated as I cleaned off his cock one final time. Satisfied, I let him put it away, pouting that my time with my new toy was over. Mistress handed Damien her card, thanking him for allowing me to service him.

"I think Damien, that my Rory would enjoy playing with you in the future." He laughed, the tiniest hint of a blush in his cheeks, admitting that he'd like that as well. With a nod, he left, Mistress hugging me from behind while I remained on my knees.

RoryRouge
RoryRouge
597 Followers
12