Anal Only

Story Info
Rory's bet with a friend to help with a personal goal...
3.3k words
4.62
14.6k
36
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
RoryRouge
RoryRouge
621 Followers

I groaned in frustration, lifting off my dildo with heavy breathing, exhausted legs no longer able to support me. Another night of trying, riding the edge, and failing to cum, my caged clit between my legs tingling with a desperation that only came through that perfect mix of denial and anal play. Months of trying to cum like this, each attempt always met with the same, frustrating result. It felt amazing, but I couldn't find my sought after release.

Pouting, my lock still set for a few more days, I cleaned and put away my toys, tossing in bed as my imagination flooded into me. Thoughts of being fucked, cumming hard while my clit leaked in its cage, body quivering from the intensity of it. I whimpered, my cage tight as always after a week of denial coursed through me, already knowing I'd be awoken later in protest.

The next night I sat down with friends to watch the game, drinking coffee to stay awake from my restless sleep. Chuck, the only other kinky friend in our little group, smirked at me, knowing exactly why I was in such a foul mood. I blushed under that knowing grin, refusing to acknowledge his subtle nods. However as we walked home together later that night, I knew he wasn't going to let it go.

"Still no, huh?" I pouted, staring ahead while I pretended to ignore him.

"I don't know what you're talking about..."

Chuck laughed, pushing my shoulder after seeing my glare. "Why don't you just let me help?"

"No! I can do this, I know I can!" I huffed, blushing once more at his continued smirking, enjoying my torment far too much for my liking.

"Oh come on,Rory...I'll even pick out a cute outfit for you to wear." My glare intensified in his direction, fighting the urge to give in. But Chuck sensed my hesitance, knowing how desperate I was after being locked for so long. He lingered in front of my building, pushing me up against the railing, making me softly moan against his body.

"I'll tell you what, if I can't make you cum in your cage then I will drop it completely, never bother you about it again. I'll even buy you that pretty maid's dress you've been saving up for." My eyes went wide, secretly hating myself for ever telling him about that! The cutest pink uniform you've ever seen, a little heart cut-out on the chest to show off my breast plate, tight latex with ruffled sleeves, petticoats, and a beautiful pair of pink heels to match. I wanted it so badly...

"But," Chuck continued, seeing he now had my attention. "If I do make you cum, then I am going to keep those keys to that cage of yours...as you will no longer need them." I whined, my clit straining from the very prospect of his deal.

"H-how long is the bet?"

"Hmmm, let's say three months." I gasped, eyes wide staring at him.

"THREE MONTHS!?" He nodded, a finger brushing some hair off my face, getting closer and closer to my body. I couldn't help but push back against him, my poor clit aching intensely between my legs, unable to resist his touch. Blushing, I tried to look away but his finger shifted down to my chin, keeping our eyes locked.

"Do you agree, baby girl?" I knew he had won, had appealed to my feminine submissive side far too well for me to avoid. Pouting at him, throwing in a bit of a whine, I happily relented, nodding my head in defeat. Three months of being his good girl, serving him how he saw fit, with the promise that he'd teach me to cum from anal only. As much as I wanted that pretty maid uniform, I knew deep down that I hoped he succeeded.

Chuck smiled, lightly brushing his lips to mine, before dragging me upstairs. I handed him my keys, feeling part of me screaming in protest, but already committed to my word. He smirked, letting them fall into his pocket, pulling me in for another kiss. "Now, your first lesson begins tonight. Go put on that pink number you showed me last week, and come back out here on the couch."

I whined at my new keyholder, but dutifully stormed off to my bedroom. There wasn't much to the outfit, just a cute set of suspenders and stockings, with a tiny waist corset held together with clips. I quickly did up my eyes a little, throwing in some cute pink shading for fun, before slipping into some heels and walking back out, the sound of them on my floor always giving me such a rush of confidence.

Chuck had helped himself to some water, his eyes glinting with hunger as I stepped out, giggling as I flaunted myself to him, only slightly terrified being this exposed. He walked over to immediately cup my clit with one of his strong hands, whimpering after over a week of no release. The other hand gently gripped my throat, holding me in place while he kissed me, forcing moans out of my lips.

Pulling away, thrown into my submissive nature, Chuck pushed me to my knees. This wasn't the first time we had fooled around, dabbling in sharing our kinks back and forth the odd time. Yet knowing he had my keys, and our little bet, made the tension and energy between us almost palpable. I could taste it, my body aching to serve him as I stared up at that stern, handsome face. The intense look in his eyes told me he felt the same way.

"Don't worry, Rory. I will teach you how to be my good girl. When I'm done with you, you'll forget what it's like to even have a cock." His hand still on my throat, tightening just ever-so-slightly, I shook from his proclamation, my excitement hitting its peak under his control. With a throbbing clit, I took his big cock in my mouth, letting it slide across my tongue as he used me, never letting our eyes disconnect.

I watched later on my knees as he left, his cum still coating my mouth, filling me with the orgasm I couldn't have myself. My keys, his keys, went out the door with him, leaving only a depraved submissive slut in its stead, unsure of what to do with myself as I knelt there.

Throughout the week Chuck messaged me, demanding pictures or simply to tease, my clit aching far more intensely than before. Each time he came over I found myself on my knees, feeling so pretty in lingerie, while he used my mouth over and over to cum. I knew my brain was tormenting me, but it felt like each of his orgasms I swallowed added to my own desire to cum, as if I was being filled up by his releases. That need continued to build, until my imagination was consumed by it, tormenting me relentlessly.

After a week of being caged for him, 15 days of not cumming, I whimpered tied to a chair in the bathroom. Chuck took his time, watching me as he cleaned and shaved my clit, drool dripping down my chest from the ring gag he'd forced me to wear. It felt so good to feel my erection, throbbing and pulsing in his hands, yet he offered no chance to cum. One stroke would be all it took, already pushed to the brink of my desperation, knowing how close and easy I was to a release.

But it never came, just his smirking, evil face as he let my erection slowly fade away, locked back up in my cute pink cage before he untied me. The ache in my balls was constant now, a consistent reminder of the deal I had made with him, feeling as if they'd explode at any moment. But Chuck just continued to smile at me, laughing as he saw the fire behind my eyes. If he was worried about our little bet, he didn't show it, refusing me the use of any toys, simply offering his cock to me each time we saw each other to suck...which I had to begrudgingly admit to myself I really wanted.

Two more weeks of this torment. Two more weeks of being left denied, only able to appreciate my erection once a week, while the need inside of me grew and multiplied. After a month of not cumming, not feeling anything inside of me, I nearly broke down in tears watching Chuck lock up my clit once more, clean and shaven, returned to being ignored. He saw that desperation in my eyes, offering a kiss on my cheek before his cock slid past my ring gag, once more using his new, desperate toy.

But, as I prepared to taste his orgasm, one that seemed to always be on my tongue now, he resisted. Untying me, his cock still hard, dripping with my saliva, Chuck led me to my bedroom, freed from my gag. Wearing his favourite pink outfit, I whimpered as he pushed me back onto the bed, silently tying each of my legs separately, thighs now connected to my calves. Arms cuffed and bound behind me, I was left stretched out and exposed, only able to watch as he rubbed his cock against my clit.

"I think you are ready, baby girl." I whimpered, shaking as he pulled out a selection of plugs and toys from my collection. Soon he had me moaning uncontrollably, as I felt lubed fingers, plugs, and dildo's begin to stretch me out, pushed deep inside of me, sliding over that wonderful g-spot. I sank into that sensation, denied to me for far too long, feeling the familiar tingling in my clit.

Surprisingly, Chuck unlocked my cage, the ring and straps still connected while I felt my cock grow for the second time that day. Eyes wide, I moaned louder as he stroked my cock, feeling the intensity trapped inside of it, knowing just how eager I was for a release. With a firm grip not letting my twitching go anywhere, he slowly slid his own cock inside of me. I shuddered, my body brimming with energy all over as I felt him push in and out of me, his hand constantly stroking my freed cock, slowly and purposefully.

"Oh, Chuck," I couldn't formulate anything more, voice taken once more to a moan, my mind falling away underneath his control. He simply smiled, continuing his slow, steady strokes on my cock, fucking me how he saw fit. As I got close, felt my orgasm building, I knew he could sense it, see the signs going through my body. Chuck let my cock fall on my stomach, gripping both my legs as he picked up his pace, fucking my ass hard and fast.

I forgot how to breathe, how to think, how to moan. I was a prisoner to my building orgasm, feeling it hit me hard, harder than it ever had before. Tearing through me, I barely felt the jets of cum leaving my cock as I came, my entire body on fire, quivering in the arms of my friend. Without my binds I most certainly would have fallen off the bed, unable to control anything at that precise moment, as wave after wave of pleasure crashed over me.

I finally screamed, gasping for breath as I felt his big cock continue to fuck me, my own orgasm covering my chest and parts of my face. Growling, Chuck tensed up as well, shoving himself as deep as he could, pumping cum into my little hole. Half smiling, half laughing, he collapsed on top of me, both of us a sweaty, cummy mess. I moaned happily as he planted tiny kisses on my lips, feeling his cum drip out of me as he pulled out.

After both of us had slightly recovered, Chuck stroked my cheek with a finger, collecting cum for me to suck on. "I told you, baby girl. Soon you'll be able to do it with your cage still on, leaking cum like the little whore I know you are all over, unable to cum any other way." I whimpered under his words, feeling them wash over me, knowing them to be true. He left one more deep kiss on my lips, lifting up to stare down with that stern look on his face.

"My own little anal-only toy. I cannot wait to break you." Chuck left me a sticky, bound mess as he moved about cleaning up the toys, his words echoing and tormenting my mind. After showering in his arms, securely caged once more, I was left yet again in my bed, aching and throbbing at the thought of what he had planned for me. He left my questions unanswered, only offering a smirk and a kiss on my cheek, only one thing certain in my mind.

I was definitely going to lose this bet.

All through the week Chuck continued to drop by, ensuring I was kept desperate and filled with a mouthful of his cum. Each weekend I was bound similarly as before, sometimes with my ass in the air so he could stroke me from underneath, each time cumming as he fucked my ass, always removing his hand before I climaxed. After another month of this treatment I couldn't even think of cumming without him inside of me, feeling that big cock slide perfectly over my g-spot.

Then it happened, Chuck tying me face-down into the mattress as he often did, his strong hands cupping and spanking my full, poor balls. Whimpering into my gag, I waited for him to unlock me before being fucked, feeling that erection I craved, his hands on my cock, my orgasm milked out of me. But he did none of that, simply sliding his cock inside of me, stretching my ass out in the perfect way, forcing shivers through my body.

I whined into my gag, realising that the time had come, that he had no intention of freeing my cock. Left throbbing in its cage, my clit pulsed eagerly for a release, not seeming to care that I hadn't been freed. Chuck ignored my whining protests, spanking my ass over and over as I was fucked, used, and split apart. I was his toy to use, his pet to tease, and his good girl to claim. We both knew it would happen, both knew it had been building up to this moment, and both knew I was ready.

I felt my orgasm as hard as before, legs quivering as I was fucked through my release. Trapped by both my binds and my body, I could only lie there in a wondrous torment, shaking and screaming into my gag, as my clit erupted between my legs. Not stopping until I heard Chuck groan, I was still in the throes of my own orgasm as he filled me with cum. Leaving me twitching, barely able to function, he trapped his cum inside of me with a plug, letting me recover from what just happened.

Untying me, Chuck pulled my body against his, stroking my hair while I cried happy tears. Years of trying, of desperately wishing to cum just as I had, done so easily by his control over me. I nuzzled into his chest, sniffling as I whimpered, my clit and plug constantly pulsing with a need that seemed to now permanently stay inside of me. I felt his strong arms surround me, pulled closer and closer towards him, never letting go.

He had won, and I couldn't be happier.

Kissing my forehead, he smiled down at me. "I told you, Rory. Didn't even take three months to make you cum like a good girl." I blushed, resting my head on his shoulder as I stared up at him. "You know you belong to me now, right?" I nodded, showing my friend just how much that thought excited me, giggling with a nervous energy. He simply laughed, pulling me close for a kiss.

"I am your Master now, Rory. Still your friend Chuck too, but whenever I require it, you are mine baby girl." I whimpered, his words seeming to travel directly to my clit, throbbing once more.

"Yes, Master." The first time I had ever used that word to mean something, and it felt so right.

Our bet had concluded, with my inevitable yet satisfying defeat. Master Chuck kept my keys, continuing to bring them over once a week to ensure I was clean and taken care of, knowing that I would never touch my own cock ever again under his control. Each week he teased and played with my ass, now able to make me cum in any number of ways he saw fit. I easily fell into being his happy little pet, eager and desperate to only cum from his hands.

I was addicted to his cock, how it felt sliding in and out of me, constantly plugged and ready for him. We traded going over to each other's apartments back and forth, seeing one another multiple times a week, often feeling I had more of his cum inside of me than my own. I couldn't be happier, serving a Master that was also my friend, wanting nothing more than to be his good girl.

Soon I wore a selection of cute chokers full-time, a subtle reminder of my devotion to him. From time to time he replaced it with a cute pink collar, the leather tight against my throat as he used me, saved for special occasions...or when I was being too much of a brat. Master's control of me continued to grow, knowing when I needed a firmer hand.

After my collar came piercings, with Master's approval and guidance I soon had my sternum, nipples, belly button, ears, and finally clit adorned with stainless steel. It was weird being freed from my cage after so long to heal, but Master and I took great care to keep me denied, not wanting to be anything but his pet, my desire to play with my clit no longer there.

As the weeks passed for my piercings to close and heal, Master showed me a new cage he purchased for my clit, the piercing sitting perfectly in the much smaller pink prison. I squealed with excitement, knowing I'd never be able to take it off. Left trapped in my cage, thrust into my submissive mindset, knowing I never, ever, wanted to leave.

When he finally caged me, seeing my clit pierced and trapped for the first time, I cried just as happily as I did the first time he made me truly cum. Another step to solidifying me as his perfect little pet, I snuggled into his lap as I felt the constant throbbing between my legs, now a welcomed companion in my life. It focused me, helped me be a good girl, and diverted all of my energy and need into pleasing my Master. My friend.

Whether I was on my own, lying in bed with my hands cupping and teasing my clit, moaning into the darkness. Or if Master was there, both of us sweaty and exhausted, my body filled to the brim with his cum, a constant taste on my tongue. Either scenario left me with a smile on my face, the constant knowledge that I was owned, collared, and happy. From a simple desire to cum anally, I had been turned into the perfect anal-only slut, patiently trained and enjoyed by my Master.

I knew he had more things to teach me, train into me, and demand of me. I knew his control would deepen. I knew my journey towards being his good girl had just begun.

And I couldn't fucking wait for more.

RoryRouge
RoryRouge
621 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Airborne - The Search Rory takes a flight for the first time in girl mode!in Transgender & Crossdressers
Rory, the Secretary Rory finds a job as a secretary, with strict conditions.in Transgender & Crossdressers
The Town Sissy Pt. 01 Rory finds herself at the mercy of the law in Great Oaks.in Transgender & Crossdressers
A New Position A friend helps Rory get a new job, with a difficult boss.in Transgender & Crossdressers
Our Shared Master: Pt. 02 The completion to a wonderful weekend.in Transgender & Crossdressers
More Stories