Mistress Rory

About two months into being owned by my Mistress, she introduced me to her friend, Anna. Very shy, quiet, yet obviously curious about Rory, Anna and I didn't have many interactions at first. Mistress told me she was very nervous around men, thinking that maybe meeting Rory would be a nice way to help her overcome her nervousness.

At Mistress' request, I was always friendly to Anna whenever she came over, smiling as I said hi, but for the most part ignoring her. More often than not when I was with my Mistress, Anna was there. Sometimes she would hang out with Mistress while I cleaned or did my chores, or pretend to be reading or on her phone while she snuck glances at me. I would just smile, that girly part of me enjoying the attention, continuing to be a good girl and go about what I was told to do.

Weeks past and Anna got more and more bold. Moving to sit closer while I cleaned a certain room, those sneaking looks becoming longer and less subtle. All the while trying to pretend she was ignoring me. It was all I could do not to giggle, finding her utterly adorable. When Mistress had me in a girly mood, I would tell her how cute Anna had been that day, making her smile and call me a good girl for being so patient with her.

One day Anna accepted the invite to attend a little gathering from my Mistress. I was serving dressed in a nylon crop top with stockings and garter belt. High heels made me tower over all the women there, yet I had never felt more subservient. Just a good girl who knew her place. However, my clit was exposed in this outfit, tiny cage pushing it against my body the way Mistress (and I admit, myself as well) liked it. Cute jewelled plug adorned my little hole, completing the ensemble Mistress enjoyed dressing me in for these outings.

Anna sat quietly all evening, as the other women swapped back and forth from teasing and humiliating me, to outright ignoring the "help" for the evening. Both interactions made me blush, clitty excitedly throbbing at the treatment of these wonderful women. Seeing how docile I was, how attentive, Anna seemed to loosen up, no longer afraid of this silly sissy.

And her eyes never left my caged clit.

My next outing as Rory, Anna walked right up and hugged me. Dwarfed by my tall body in heels, I hugged her back against my tummy, my hand running through her hair. Smiling, the ever so quiet Anna very quickly became a chatterbox, following Rory around Mistress' house the entire time she did her chores. We became fast friends.

She began to thoroughly enjoy my teasing and humiliation at the hands of others. Giggling as I was spanked and fucked, she would tease me about cumming from Mistress' big cock. Blushing I would always shush her, but that only made her laugh. Anna even graduated to teasing me herself, softly running her hands over my caged clitty. She enjoyed sitting on my lap in my maid dresses, lifting up the frilly hem, cupping my poor balls in her tiny hands. With big eyes she would stare at me, mischievously rubbing as she watched me being tormented.

One day Anna confessed that she wanted more from our friendship. Being a submissive herself, but finding it hard to trust people, she wanted Rory as her Domme. Her Mistress. This, naturally, made my Mistress burst out laughing, in a tone I did NOT appreciate! But Anna was committed, knowing what she wanted. I had never thought of Rory being dominant, leaving that part of me in "boy-mode". Yet, staring at her big beautiful brown eyes, that adorable pleading expression, I knew there was no way I could say no.

Initially we took it slowly, only playing under the supervision of Mistress. My clit was no longer my own, and its unlock and usage was not up to me, but Anna wasn't really interested in it. She enjoyed it caged, enjoyed playing with my denied and aching balls. Rory also was more interested in pursuing Anna in other ways, a sissy with her own sub. We started out with a lot of kissing, Anna sitting on top of me, rubbing herself into my clit. It left me feeling deeply aroused after each session, which my own Mistress took full advantage of.

Slowly we pursued our dynamic further, learning this new territory together, with me growing more confident as a Mistress, and Anna growing more comfortable as my sub. Mistress would help, giving me tips and advice, while continuing to humiliate me as her sissy, which always made Anna giggle. After one play session at Mistress', I had Anna screaming to cum on my fingers, her begging pretty eyes fixated on me. As she had come down from her orgasm, cuddling in my arms, I knew I would not be able to let her go. The next day I collared her, to a chorus of happy squeaking and hugs.

Months later, my happy sub in tow, we went out for the first time as Mistress and slave. It was a club we had both visited many times, and yet tonight was very different. As I clipped a leash to her cute little collar, I admired how adorable Anna looked tonight. Her body was entirely covered in pink latex, dress hanging down to just cover her stocking tops. Bright pink that hugged her chest, black stripes running along the end of the sleeves, hem, and her stockings. She looked like a piece of bubble gum, and completely delicious. We had giggled a lot getting ready, sliding the latex up her legs. She loved her outfit, damp panties a telltale sign of it.

I HAD an outfit to wear with her, but Mistress being Mistress just couldn't help but dress her own sissy. A nylon bodysuit, crossing pattern throughout, hugging my caged little clit. Anna had ran her hands all over me when I first put it on, giggling at her Mistress. I shot her a glare, blushing at what I was being forced to wear, which only made her smile grow wider. Over top of my garter belt, connected with tan seamed stockings, I felt completely exposed, staring at my Mistress as I hoped she wasn't going to send me out like this.

Mistress had much different plans. After all, her sissy had to be dominant tonight, in control. And she should be dressed for the part. A tight latex skirt was added to the outfit, hugging every part of me. I felt the constricting garment with every step and breath, my ass being pushed up once I put on my heels. Staring at myself in the mirror, I did strangely feel more dominant, in control. Even though my little caged clit was clearly outlined by the tight fabric. However, when I saw Anna's stare, that hunger in her eyes, drinking in her Mistress, I knew this was the right choice. I walked right over to her, heels clicking on my Mistress' floor, hooking her collar with my finger, pulling Anna in for a kiss. Brattiness falling away, she was mine after that.

With that same wide-eyed look never leaving her Mistress, we walked into the club. Anna stayed a bit behind, blushing as she was led inside on my leash. I showed her off to everyone I knew, my adorable little sub. Giggling and blushing through it all, Anna drank in the attention, loving her latex outfit, and the women fawning over her. Some of Mistress' friends congratulated me on such a well behaved sub, making a blush of my own come across my face, dropping into a curtsy as best as I could in this skirt, still showing respect to my betters. I was still my Mistress' sissy, after all.

Settling into the night, drinks in hand, I watched my little Anna excitedly scan the room with her eyes. Overtly aroused, seeing the scenes of sex and fetish wear all around her, I smiled as her legs shifted together, tiny little whines escaping her painted lips. I brought her onto my lap, her eyes latching onto mine, as I gently ran my finger up and down her very wet pussy. So desperate to cum, she moaned lightly as she held onto me tightly, that desperate and pleading look in her beautiful stare.

We were interrupted by a couple, two lovely women dressed to match. Classic black dress with stockings, they asked if they could join our table. Anna immediately burned with embarrassment, hiding in my neck. I extended a friendly invitation to our new friends, my finger never leaving her wet little panties. I could feel the humiliation in her breath, wanting to disappear, yet not wanting her Mistress to stop, still greedy for her orgasm.

The couple asked about our situation, and had quite a few questions for me. I happily told them my story, how Anna and I had met, and of course about my amazing Mistress. As we chatted, Anna became less embarrassed, still aroused and frustrated, so I helped her down beside me so she could join in. Still blushing the entire time, feeling the eyes of the two women on her, we all chatted and laughed.

We learned that they enjoyed playing with other women together as a couple, usually a sub who enjoyed being the center of attention. Direct and not subtle, I smiled as Anna's eyes went wide at the thought. Continuing their straightforward approach, I asked if they would be interested in playing with my little sub, both of them biting their lips with a nod. They drank Anna in with their stares, wandering hands hovering very closely to her latex covered body.

I watched Anna blush and squirm, seeing the intent from the women around her. Gently cupping her chin, I directed her excited stare to me, asking if she wanted to be a good girl for this couple for a little while. Soft adorable noises emitting from her surprised open mouth, barely able to breathe as I stared at her. Nodding enthusiastically, I kissed her pretty lips, telling her to be a good girl. Getting up, I walked behind the table, taking Anna head in my hands, allowing both women to slide up against her.

Her head pulled back, staring up at me, I never broke eye contact with her while I laid out some rules for our new friends. They agreed to all, promising to take care of my good girl. Openly moaning, feeling the beginning of exploring fingers gently lifting up her dress, Anna stared in to my eyes, overloaded with her own arousal. I asked the women to slowly take off Anna's panties. Each holding a leg, they slid the wet panties down her latex stockings. Handing me them, they kept her legs wide and exposed, on display for all to see. Anna was in full sub mode now, lost in her own horny little mind.

I leaned in closer as I told Anna the rules for this little play session. For each time she came at the hands of these wonderful women's fingers, I would tie her up in a playroom here, hands high above her head, and give her five strokes with the cane. A cute little whimper escaped her lips, remembering how it had felt the first time I did that to her. The marks it had left, the whimpering and tears it had left her in. Gentle hands caressed and gripped her as she listened to me, nodding that she understood.

Smiling at my good girl, I dipped low and kissed her deeply, slipping a pair of handcuffs around her wrists while she was distracted, hands out of the way for her upcoming torment. I finished with placing her soaked panties in her mouth, closing those adorable lips around them. With one last pat on Anna's cheek, I winked at our new friends, giving them full control over my good girl.

As I walked away I heard her immediately moan, muffled by her cute panties, knowing my little sub was in a lot of trouble. Smiling, I moved to the bar to refresh my drink, feeling powerful in my skirt and outfit, thoroughly enjoying my role as Mistress for the evening. However when you are a sissy of a controlling, dominant, and evil Mistress, things can change rather quickly.

I felt a strong hand grab my ass behind me, firm and commanding, making me squeak. Any feelings of power washing away as I turned to see a gorgeous large man before me. His devilish smile greeting me, saying he was a friend of my Mistress. I blushed, greeting him warmly, instantly falling into the role of my Mistress' sissy. Leaning in to whisper in my ear, he said a phrase that made me melt.

Your Mistress said Rory would be a good girl for me tonight

I moaned, knowing Mistress had set me up! She knew that I was trying to be a Domme tonight, to be in control. And yet she sent this handsome gentleman to ruin that, to take control of Rory in a way that she couldn't refuse. Eyes as wide as my Anna's, I simply nodded, letting him take me by the hand to a different room, now my Dom for the evening. He stripped me of my skirt, leaving me in my nylon bodysuit. All my feelings of power melted away, instantly turned back into a good girl. Into a silly sissy.

I was placed over his lap, spanked playfully as he reddened my cheeks. My clit began to leak immediately, always losing control when I was dominated in such a way. He brought me against his chest, rubbing his strong hands over my clit, my eager tongue cleaning his fingers when they were brought to my mouth. It didn't take long for me to cum from his torment, feeling very similar to my current subs position. He firmly made me clean him once again, before forcefully dropping me to my hand and knees, collecting my orgasm off the floor with my tongue.

Still tasting my release, he unzipped and slid his rather impressive cock into my mouth. I moaned with need around him, taking all of his cock in my throat, nose pushed deeply into his pelvis. Mistress had trained her sissy well. Both hands on my head, he fucked my face at his own pace, using me for his cock like it was my asshole, thrusting with need. I breathed where I could, not daring to tap out, not wanting this beautiful cock to ever leave my body.

Leaving me on my knees, he relented in his face fuck, allowing me to gasp for a much needed breath or two. I continued at my own pace, his cock back in my throat as I worked him over, staring up at this gorgeous man, my owner for the evening. I saw him getting close, felt it in his cock, knowing I would soon earn his cum. And earn it I did. I whimpered happily as his orgasm flooded my mouth, feeling him fill me. I eagerly showed him all the cum I had collected, waiting for his nod before swallowing, returning to clean off the big cock I had quickly fallen in love with.

My hands softly stroking his still hard cock, eyes pouting up at him, I tried my best to get him to fuck me. My asshole desperate for this cock to be inside of me, pulsing at the very thought. But he simply laughed at the horny sissy before him, instead bringing me over his lap once again. He aggressively rubbed my little hole with one finger, forcing moan after moan out of slutty Rory. The other hand rubbing my clit and balls, mixed in with playful slaps, I came once again from being handled. And for the second time that night I cleaned my orgasm off of him, the taste of his cum mixing with mine.

Smiling down at me, he told me to go back to my sub, who I had almost completely forgotten about, helping my back in my skirt, zipping me up while he pressed into me. I leaned back, grasping his neck with my hand, not knowing how he knew my Mistress, but desperately hoping it wasn't the last time he used her sissy. After touching myself up from being used so thoroughly, I went to go find Anna. And oh my what a sight she was.

Panties still in her mouth, such a good girl, poor Anna was in a delicate balance of euphoria and agony. Sweating and exhausted, she moaned and screamed through her panty gag, currently being iced down with cubes from the drinks of her tormenters. Her poor pussy looked spent, quivering as they ran ice so very close to her reddened lips. I returned to the spot I left, holding her head in my hands, tired eyes smiling as she saw her Mistress.

I removed her panties, her moans no longer muffled, asking how my good girl was. Incoherent mumbling was all she could muster, the adorable thing too spent to even speak. I giggled, staring at the couple in front of me who looked rather pleased with themselves. Gently stroking Anna's hair, they told me all about how good she was. Still spread between them, hands caressing my happy sub, I watched them touching and holding my good girl, mentally making a note to get their number. Anna had not felt their touch for the last time.

I asked how many times she came, looking back to my Anna. Immediately she blushed, being brought back to reality. I guessed the number was high if she was so scared to tell me. I leaned down beside her, lips right against her ear. I told her to be my good girl, and tell me how many times these lovely ladies had made her cum, how many times those skilled fingers had pulled orgasms out of my subs eager little pussy. Anna whimpered, barely able to audibly voice the total, a mix of fear and embarrassment in her voice as she said it.

Ten...

I gasped wide-eyed, staring at the couple for confirmation. Smiling, quite proud of themselves, they confirmed my eager and horny little slut's story. My own hands now running up and down her body, I pretended to be disappointed, little tutting noises as I scolded my terrified little Anna. I asked if she knew how many strokes of the cane she had earned. Whimpering she nodded, my fingers playfully teasing her erect nipples through the latex as I demanded her to tell me.

Fifty

Anna whined as I laughed at her, seeing a slight tremble in her body. Fifty strokes was far too many for my good girl (it was far too many for her Mistress!), and I quickly came up with a solution. Coming around the table, I helped her onto shaky heels, waiting until she had some strength under her. I told her she had ten minutes to find other subs in the club to help with her total. However she could, she had to convince them to share in five strokes from their owners, to take her punishment for her. I also told her to go get some water so she didn't collapse. Whimpering, she scooted away, a desperation in her little steps.

I sat down beside my new friends, thanking them for taking care of my Anna. I told them I would very much enjoy if they wanted to do so again sometime, a request they eagerly agreed to. They described some ideas they had for her once she was at their place, making me smile thinking of Anna being put through that. Oh, she was going to be very sore after a night with these two.

Getting my own water, equally tired from my own experiences of being a good girl, I was surprised at how quickly the ten minutes went by. Anna stood before me with two new friends, dressed in all sorts of leather, their Dom's behind them. I smiled at the cute boys, asking them if they were here to help with my Anna's punishment. They nodded, one looking far more eager than the other. Their Masters laughed behind them, enjoying the scene. We all gathered, a kinky little band, and headed to the clubs dungeon.

Waiting for our turn, my little sub getting nervous, I stroked her shoulders, telling her it would all be okay. She grabbed my hand tightly for support, getting ready to receive her punishment, to be my good girl. As the room cleared for us, we watched the other subs being teased and punished, Anna wincing with each stroke of the cane. When her time came up, I asked the small crowd that had gathered if anyone else would help with my subs predicament.

A voice said they had a sub who could, freezing me in place as the man who's cock earlier I had down my throat walked in. He said since this sub had also enjoyed two orgasms recently, surely she could receive ten of Anna's punishments. I blushed, glaring daggers at him, knowing his intention. Anna eagerly agreed, asking who the sub was, desperate to beg them for help. Smiling, without a word, he simply pointed to her Mistress. Anna gasped, eyes wide as he described just what I had been doing while she was cumming her little heart out.

Giggling, she got on her knees in front of me, pleading for me to help with her punishment. Staring down at that adorable bubblegum wrapped princess, my cute sub, I knew I couldn't say no. With a sigh, I kissed her deeply, walking up to my evening Dom so he could once again strip me of my empowering skirt. Left exposed, my excited clitty still dripping from my earlier orgasm, I let him lead me to the center of the room, hands firmly cuffed to the ceiling.