Mistress' Cute Cocksucker

You're going to look so cute with a cock in your mouth.

Those words still haunted me, days after Mistress gently whispered them, kneeling in front of her, chin cupped in firm, comforting hands. I still blushed thinking over that night, and the implications it came with.

I met my Mistress a few months ago, sharing with her all of my desires to be Rory. The outfits, humiliation, goals, interests, "firsts", I held nothing back from those dominant, brown eyes. Smiling, saying she'd be happy to help, I found myself back in her house, a collar around my neck. All night she showed me what it was to be owned, used. I was taught how to curtsy, walk in heels, serve my Mistress, and be her good girl.

I left that evening hooked, still wearing the collar she placed on me, knowing I wanted to serve her. Months of training, conditioning, and feminising had led me to the previous evening, on my knees in front of my Mistress, agreeing and begging for the chastity cage she'd bought for me. Even knowing the cost of earning a release, I accepted further control, wanting nothing more than to be her good girl.

Fifty.

Five. Zero. It was a daunting number, more so in the context of my release. As I knelt before my Mistress, sucking on her fake cock as I had been trained to do, she informed that I owed her fifty blowjobs for my release from her cage. Fifty cocks. Fifty blowjobs while I was denied the ability to be erect at all. Fifty times I would be her sissy cocksucker. Her good girl. I knew it was a hefty price to pay, but staring up at my Mistress, the excitement in her eyes as she showed me the cage, the desire to see me with a cock down my throat. I mean, how does a girl say no to that?

Each Saturday Mistress said I would come over to her place, spending the day being her maid and slut. She would provide a cock for me to suck each week, optional if I wished to agree or not. But my cage would not be removed until I had sucked fifty cocks, whether under her scrutiny or not, sending her proof in the form of a film or picture. Doing simple math, I knew that it would take almost a year to finish earning my release, unless I found ways to be a cocksucking sissy on my own.

That first week I barely slept, straining against the tiny pink cage that now controlled my cock. Whimpering as I tossed and turned, desperation beginning to sink in. By the time I found myself dolled up at Mistress' house on Saturday, my little maid outfit constantly brushing my new "clit", as she liked to call it, I could of nothing else but the ache between my legs. Mistress thoroughly enjoyed the effects the cage was having on me, gently running her fingers over my denied balls, savouring the tiny moans escaping her little slut.

All afternoon I minced around her house as I had been trained, dutifully doing each chore as I had done many times. Yet, my clit, and the desperation I felt, made each task feel that much harder. Not helped at all by the giggling woman who controlled me, running her hands over my stockings any chance she could, bending me over to play with my plug, feeding me the excitement leaking from my poor clit. I could barely think when I had finally finished my list, so lost in my own denial.

As I curtsied for Mistress, I heard a knock at the door. Wide-eyed, I whimpered when the smiling face that controlled me motioned for me to answer it. Blushing, so embarrassed and yet not daring to misbehave, I found myself curtsying for a strange man as he eyed me up and down. Greeting him warmly, Mistress invited him in, taking my shaking hand as we followed into the living room. I felt her hands all over me, lifting up my uniform to play with my ass and clit, playfully telling me it was time to start earning my release.

Eyes wide and mouth watering, I watched as he slowly unbuckled his pants, casually taking out his cock. Mistress' hands never left me, whispering encouraging words as her fingers gently circled my clit, the ache ever present, the need to cum stronger than I had ever felt before. Asking if I was ready to be her good girl, I could only nod, my eyes fixated on his growing, beautiful cock.

Bigger than I had ever seen, I knelt down in front of him, hands shaking as I reached out. Firm and growing, I moved my hand up and down, slowly gaining confidence, Mistress never leaving my side. Lips in my ear, she told me to ask nicely if he'd allow me to suck his cock. If he'd help with my release, and how appreciative I should be that he is. My own cock locked away, giving pleasure to the very thing stolen from me, and she wanted me to beg to do so.

And I did.

Staring up at him, hands more firm as his cock hardened, I begged to suck his cock, to make him cum in my mouth, to be a good girl. A good sissy. He smiled, taking out his phone, saying I had to show me his cum before I swallowed, and listen to his every instruction. Whimpering, not knowing what he would do with that phone, I agreed. After a red light appeared on the back, he nodded, and with an encouraging squeeze from Mistress, I lowered my lips onto his cock.

So warm, far more realistic than the one Mistress had me practice on, I immediately loved it. Playing with the head of his cock with my tongue, I moaned with him in my mouth, savouring my first cock. I was soon lost in pleasuring him, addicted to the sensation of the cock going in and out of my mouth, to the groans coming from the man it was attached to. A few minutes into my devotion, he stopped me, placing his cock on my tongue for a picture, and select phrases to say into the camera. I shot Mistress a glare, KNOWING these were most certainly from her.

Thank you for letting me suck your cock, Sir.

It is so much bigger than my little clit.

I can't wait to feel this big cock cum down my throat.

I am a good sissy cocksucker.

Please can you cum in my mouth, Sir?

I blushed through each one, so humiliated knowing it was on camera. My tormentor smiled, nodding for me to continue, Mistress giggling behind me. My face reddened, I went back to pleasuring him, one again losing myself in sucking cock. I whimpered as a hand rested on my clit and plug, rubbing and teasing while I shoved him down my throat.

His groaning intensified, cock hardening even further. I moved a hand to his balls, massaging gently, as if to coax his orgasm into my mouth. Mistress placed a hand on either side of my face, holding me still as he grunted, the cum I had worked so hard for finally erupting, filling my mouth. Salty and warm, seeming endless, I moaned as I felt him release inside of me, coating my cheeks and throat.

Waiting for him to finish, twitching as the last bits of his orgasm shot out of his cock, I breathed heavily as I was pulled off of him, showing the camera my filled mouth. Coating my tongue, waiting patiently for his permission, I stared into the lens as he told me to swallow. It took me two tries, and a strong will, but I proudly show off my empty mouth, still feeling his cum everywhere. Smiling, he patted my cheek, calling me a good little cocksucker. I felt a shameful amount of pride hearing those words.

Making sure to clean off his cock, I sat on my heels as he dressed, talking to Mistress as she saw him out. A friend of hers, to which she never did supply the name of, I blushed as she told him to drop by whenever he wished, that I would always be happy to be of service. Coming back to find me in the position she left me in, Mistress sat down in front of me, a proud smile on her face. Kissing my cheek, she called me her good girl. Her little sissy cocksucker.

Pulling out her phone, I whimpered as she showed me the video that had just been shot. The sissy maid, eagerness in her eyes, sucking cock for the first time. Rubbing my excited little clit, she whispered how happy I had made her, how cute I had indeed looked with a yummy cock in my mouth, and how excited she was to see it again. Nearly cumming from her touch, my caged clit aching for a release after all that excitement, she left me that Saturday with a chilling, yet intoxicating statement.

Only forty-nine to go...

True to her word, each week Mistress would have a visitor arrive at her house after I had finished my chores. Conveniently, she "forgot" to leave out that they had to be different cocks, so her returning friend who enjoyed filming and using my mouth no longer counted to my release. Although I'd be lying if I said this stopped my enthusiasm to pleasure his gorgeous cock.

My third week caged she surprised me by inviting over a Dominant friend, bringing with her a collared and caged sissy of her own. I burned with jealousy and humiliation when it was revealed that I was to provide her the reward I was yet to earn, watching as Mistress' friend unlocked her clit, listening to the moans and gratitude as she came down my throat. Twice.

After a month I caved, knowing I couldn't wait a year to be released. I met some men through Mistress, or a club she had brought me to a few times. The owner, knowing about the situation of my release, decided to "charge" me for using his club to find people, soon adding another weekly evening I spent in my maids outfit. Both he and his husband thoroughly enjoyed tormenting, teasing, and humiliating me. I couldn't believe that I had to serve them, just to be able to find cocks to suck at his club!

Soon it seemed every guy I talked to knew that Mistress had me locked, and the price of my freedom. I was constantly set different tasks, outfits to wear, brought to events, all to earn the chance to suck their cock. All my whimpering and frustrations were drank in by my Mistress, enjoying the situation her new sissy found herself in. Each Saturday, after pleasing the man or cock she brought home for me, I'd find myself in her arms, aching as she rubbed my poor clit, running my own dripping excitement along my tongue.

With one more to go before my release, my clit had been locked for six months. Six. Months. Every day I could feel it, the ache inside of me, the desperation. Every day I felt the strain, fully aware of the need between my legs. As I walked towards my hunting grounds, I prayed that I found someone who didn't know about my predicament. That tonight would be the last, and final price to pay for my release.

Tight blue skirt covered my black, opaque stockings and garter. A matching light shirt which I covered with a black blouse, ruffles on the waist and sleeves. Matte pink heels, and my collar/choker, another reminder from Mistress that I was always owned. Always hers. I was ready, eager, hungry, and desperate.

Blushing at a wink from the owner, I tried to ignore the "regulars" that understood exactly why I was here. At the bar with my drink, I didn't have to wait long before a beautiful stranger approached me, taller than even me in my cute heels. We chatted for quite a bit, my face red for most of it as I felt his subtle touch getting more bold, hands resting on my legs, rubbing up and down. My poor clit leaked, no longer able to control its excitement after being caged for so long. Gripping my thigh, he leaned in to whisper about taking me home. His breath so close to me, I could only nod, wide-eyed and submissive, allowing myself to be led away.

We kissed all the way back to his apartment, breathless and on edge, wanting him in ways I hadn't really felt before. Inside, I was quickly robbed of my outfit, standing only in my stockings, garter, and heels. Strong hands found my clit, forcing loud moans out of me as I was played with. I was his now for the night, fully and completely, waiting to be told how to be his good girl.

He brought me over to a chair, kneeling in front with my eyes closed while he left. Returning shirtless in boxers, I whimpered just a little at the sight of him, and the ball gag hanging in his hand. I pouted, seeing that earning my final blowjob wouldn't be so easy, growling as he buckled the gag around my head. Smirking at my frustration, he leant down to kiss my gagged mouth, motioning me to climb across his lap. Gently rubbing my ass, I cried with a confused mix of pain and pleasure as I was spanked, the sting growing behind me. Not daring to move, tears in my eyes, I stayed still like a good girl, lost in the sensation of being spanked.

Satisfied with my reddened ass, his fingers moved towards my little hole, rubbing lube and spreading me, my poor clit confused and aching, no longer sure what it wanted. I could do nothing but moan like a whore while he explored me, played with me. I felt something stretching me even further, slightly painful but also pressing hard on my g-spot, quivering as it slid inside of me. Properly plugged, my muffled whimpers returned as he again spanked and teased me, every so often pushing on the plug, the pressure almost enough to make me cum.

Tears streamed down my face by the time he knelt me down in front of him, taking out my gag to show me the mess I had made on his leg. Blushing at the representation of my excitement, I bent down to lick my mess clean, his hands on my wig, calling me a good girl. The constant feeling of the plug, the aching in my clit, and the stinging I felt in my ass, all combining to leave me in a daze, wanting nothing more than to please and obey this man.

He led me to his bedroom, soon on my knees, ass presented in the air. I knew what was coming, Mistress enjoyed me in this position as well, and I shook with anticipation. With need. I didn't care if he was my fiftieth point, I needed him inside of me. I needed to be his good girl. I needed to be fucked. The bed moving behind me, his hands on my ass, pulling the plug out, I couldn't contain my excitement, moaning and giggling with desire.

A few gentle pats on my ass, followed by his cock rubbing up and down my eager little hole. Tauntingly close, feeling his hard cock, I begged for him to fuck me. A hand gripped my waist, his other used to slowly guide the cock I so desperately needed into my ass. Arched back, I moaned loudly as he pushed inside of me, stretching my ass further than ever before. Both hands firmly gripping my hips, he pushed all the way inside of me, feeling his warm body against mine.

His thrusts quickened, my desperation grew, and my poor clit finally relented. As Mistress had done many times over the last six months, I nearly screamed as my orgasm was fucked out of me. Clit spurting and leaking, body shaking, held still by his firm grip, I quivered and moaned as it coursed through my entire body. He gave my ass a happy pat, enjoying the effects his cock was having on me, never slowing his pace.

I came two more times before I heard him groan, cumming into his condom, collapsing on top of an exhausted and spent sissy. I whined when he pulled out of me, not ever wanting him to leave, giggling as he held the cum filled condom to my lips, pouring his orgasm into my mouth. As I lay on his chest, I didn't even care that I still needed a final blowjob for Mistress, this had been a night to remember.

I didn't have to wait long, however, as I was awoken in a rush, a cock shoved down my throat. Pinning my arms with his knees, I whimpered as he used my throat as he wished, barely able to breathe as he groaned, tasting his cum for the second time in twelve hours. Taking a quick video, he made sure to capture his cock in my mouth, as well as the pool of cum I swallowed. Smiling, he leant down and kissed me deeply, whispering before he let me up.

Tell your Mistress I say hi.

Showered and dressed again, only slightly annoyed he knew who I was, I called my Mistress with delight, her giggle on the other end proof that she had been deviously behind this mystery man, and received his video. She told me how proud she was, and next Saturday she'd have a special surprise for me. My mind was a mess all week, wondering just what she had in store.

All afternoon, cleaning as usual, I could barely focus. Slightly shaking, excited for what I knew was to come. Mistress didn't help at all, constantly checking on me with her wandering touch, little whispers, biting my ear as I whimpered in her hands. My final chore complete, I could feel that anticipation in my body, my clit straining hard knowing soon it would be "free". Six months of waiting, of desperation, of being Mistress' good girl.

Taking me by the hand, she led me to the living room, greeted by a weird looking chair I had never seen before. Lubed up, Mistress eased me onto the dildo attached to the seat, legs shaking from being filled. No back to the chair, just an odd half circle near my clit, confusion evident on my face. But all I was met with was a smile, gently cuffing my ankles, binding my arounds behind me. Trussed up and helpless, Mistress placed a harness gag around my head, ring leaving my mouth open, tongue out while I whimpered at her. Her only answer was a kiss on my cheek.

Kneeling in front of me with a wooden board, she slowly took out my keys from a little box, one I hadn't seen for six months. I no longer cared about the chair, what it was, or what it did, my entire focus shifting to those two little keys. Cupping my clit and balls, now feeling as if they'd break out of my cage, she made a show of slowly, ever so slowly putting the key in the seldom used lock. Silently sliding out the built-in device, Mistress gently slid off the cage, ring falling away. I nearly cried in relief, feeling my erection for the first time in six months, almost forgetting what it felt like.

Her perfect, soft hands so careful in handling me, rubbing cream and lube over my cock, knowing the desperate state it was in. Mistress grabbed the mystery piece of wood beside her, connecting it to the front of the chair, my now uncaged cock trapped in a circle, unable to pull backwards. Clipping my collar to the top, I was completely stuck, immobilised in her new device. Wide-eyed and whimpering, I shuddered at the evil smile spreading over Mistress' face.

Are you ready for your reward, my little pet?

Skilled hands found my lubed cock, stroking up and down, always perfectly leaving me on edge. I couldn't look down. Couldn't speak. Couldn't move. I could only stare into the beautiful eyes of my Mistress, feel her hands on my long denied cock, begging and moaning into my gag like a whore to cum. She just smiled, enjoying my predicament, my torment, stopping each time I hit the edge, taking any pre-cum and wiping it on my tongue.

Slowly losing my mind, thoughts simply melting from my head, I could only succumb to the control of my Mistress. Completely at her mercy, her good girl, her toy. Whimpering, pleading, begging, and moaning. I felt her hands teasing the head of my cock, cupping my balls, so gentle and yet so firm. Mistress had me exactly where she wanted me, enjoying the full control she had of her good girl. Her perfect little pet.

Another drop of pre-cum on my tongue, that evil smile staring back at me, Mistress picked up her pace, staring directly in my eyes as she stroked my cock. Feeling myself once again pushing to the edge, I whimpered yet again. I pleaded yet again. I begged yet again. Intently staring, not leaving me for a second, I heard the most beautiful words spoken to me in a very long time.

Be a good girl and cum for me, sissy.

My cock didn't need to be told twice, pushing over the edge, finally allowed to have a "real" orgasm. My entire body shook, quivering as powerful jets of cum erupted from my cock, over and over, nearly fainting in her hands. Giggling, she never stopped stroking as I erupted, moving behind me to kiss my cheek, whisper in my ear that I was her good girl. Breathing heavily, a rush of emotions coursing through me, I thanked her over and over as best I could through my gag, exhausted and happy.

Mistress cleaned my cock and her hands, one finger at a time, all being fed back to her sissy. Even the jets of cum all over her floor were carefully collected, all deposited on my eager tongue. However, Mistress continued to stroke through it all, keeping me hard. I whined when I saw her vibrator, more lube and cream, understanding that she was far from done with me. Smiling, satisfied I was all cleaned up, she went back to work.