A Friend in Need

"Oh come on, just one time!" Charlie smiled, eyes glinting with mischievous intent, staring at me from the other side of the couch. I tilted my head, glaring as I snatched my phone away from him, putting away the photo's I now regretted showing off.

"Absolutely not! Rory is a secret, not shared."

"But you've been out to clubs as her!" Charlie whined, not dropping his inquiry, forcing another sigh out of me.

"I've been to CERTAIN clubs with other GIRLS like me! Very different." He went to say something else, but I finally shut him up with a punch to the arm. "No." Fuck me, you show offone picture of you all dolled up. Charlie had been curious, knowing I was queer and enjoyed being feminine, but I had NOT expected him to ask to see me in some lingerie!

Smirking, Charlie crossed his arms and went back to watching TV, thoroughly pleased with himself. I groaned internally, knowing full well he wouldn't be dropping it anytime soon. It wasn't even that much of a photo! Just a pretty dress and my favourite brunette wig on a night out with some friends. The thought of him seeing me in one of my more private outfits I barely shared with anyone, my caged clit fully on display, was out of the question!

Even if it did excite me just a little bit...

A few days later my suspicions were confirmed as Charlie once more continued to drop subtle hints to see my more feminine side, met with my firm refusal. We had been friends for years, played hockey together, and were drinking buddies. He was NOT seeing me in all my feminine glory! I'd never hear the end of it.

Relentless in his new quest of life, I tried very hard to ignore him as he sent a continuous stream of outfit ideas to me in messages, asking if I had worn each one. A truly horrible friend. Not really, Charlie was a wonderfully thoughtful friend, he just suffered from being a pain in the ass. Probably why we got along so well.

Weeks of this though! Of hints, eyebrow raises, subtle glances, even going so far as to bring a ridiculous pink tutu over to my apartment, placing it down on my table just to 'see what happens'. I nearly threw him out for that little prank, his snickers of laughter seemingly endless through the night. What made it worse was how hard I fought not to look at the cute, silly thing, knowing deep down how desperate I was to try it on.

A few days after he tried to turn me into a sissy ballerina, I opened the door ready to fight off whatever new plan he had, but Charlie simply smiled, his hands held out to his side in an innocent gesture. Letting him in, I eyed him suspiciously, but eventually let my guard down seeing he had not brought any new 'presents'.

Some hours later, both of us feeling the effects of a few drinks, his new plan of attack was revealed. "You know, Claire told me that she has seen Rory all done up." I groaned, putting my head into my arms.

"She helped me with my make-up one time! I'd hardly say that counts."

"No it's fine, I just thought we were better friends than that. That's all..." Pretending to pout, Charlie put his head down dramatically, forcing another groan out of me.

"It wasn't a big deal!" I said, glaring at him for guilt-tripping me, but he simply continued his charade, even putting a tremble into his bottom lip. "Dude you don't want to see me like that, it's weird!" But he ignored me, enhancing his pout, I swear even bringing a tear to his eye. I whined, angry at his successful maneuver, knowing I wasn't getting out of this one. Claire was Charlie's sister, and if she told him about helping me, then I knew it came with a lot of rub ins.

Exasperated, I growled at him. "Okay FINE! You fucking pain in the ass. I am going to change. BUT! I warned you." With a huff, my feminine side already starting to emerge and take hold, I stormed off into my room. Purposefully, I chose not to look back, knowing a grinning and victorious smile would be shining back at me. I hated him.

Sifting through my closet, I giggled on my choice to torment Charlie with. If he was going to be relentless, then so would I, taking out my favourite pink bunny suit. After sliding on some dark tights, I stepped into the bodysuit, snugly gripping me in all the right places. It had taken many different alterations before I had gotten it to fit exactly how I wanted to, even having the perfect amount of space for my caged clit. Wig, cuffs, collar, ears, and finally my tail, I smirked in front of my mirror, stepping into some pink heels to finish my look.

I did a few twirls, trying to gain the confidence to walk outside, ready to be greeted by howling laughter, praying he didn't take any pictures. With a deep breath, I opened the door, heels clicking on my hardwood as I strolled into the living room, hands planted on my cocked hip before my friend.

But Charlie didn't laugh. He didn't smirk, stifle, howl, giggle, or anything of the sort. No humiliating teasing, no jokes, no friendly teasing, just my friend wide-eyed and shocked, his mouth open, attention torn away from the game he'd been playing.

"Holy fuck..." I blushed, suddenly realising that he was checking me out. "You look fucking hot!"

"No! Shut up! Say something mean." I crossed my arms over my chest, blushing as he continued to stare.

"No way, Rory, you look amazing. Wait, is that what I call you?" He looked up at me concerned, worried about saying the wrong thing. I sighed, rolling my eyes at him.

"I usually go by Rory in girl mode, yeah." Charlie nodded, as if he made a mental note in his mind, still refusing to stop exploring my outfit with his eyes. I stomped my heel on the floor at him. "Stop looking at me like that!"

He laughed, a slight blush making its way to his cheeks. "I'm sorry! I just wasn't expecting you to look so hot. Where did you even get that outfit?" Now it was my turn to blush once more.

"I, uh, kinda made it."

"What!? Turn around, let me see."

I felt my clit start to strain, enjoying having someone to show off for. "No!" But Charlie got off the couch, now much shorter than I was in my heels, moving around my body as I stood with my arms crossed, beat red and pretending to be furious. He even tried to poke at the fake breasts I was wearing, smacking his finger away before it even got close. But he only laughed, running his hand through his hair.

"Wow. Who knew you were such a beautiful girl. Even the name Rory suits you far better." I glared at him through his compliment, but I knew this resolve I had put up was slowly melting away, firmly aware of how he was looking at me. Charlie's gaze drifted down to my crotch, seeing the cage outlined against the tight fabric.

"Ummm. Is that part of the outfit too?" My eyes went wide, suddenly remembering that some people were not, in fact, a kinky hoe like me, and didn't know what chastity was. My blush returned in full force, hands instantly covering myself.

"Y-yes. Uh-huh, part of the outfit. Mmmhmm." I walked away, sitting on the couch with crossed legs, refusing to look anywhere in his direction. I felt the couch sink down beside me, silently cursing myself.

"Liar. What is it? Tell me, aren't you supposed to like, tuck or something?" I shot him a look, but Charlie's excited eyes had returned, grinning back at me.

"It...is just something that helps me feel feminine." I said vaguely, praying he let it go.

"Can I see?"

"No you most certainly can NOT!" My glaring outrage only made him laugh, inching closer to me on the couch, feeling his leg against mine, suddenly aware of just how revealing the outfit I had chosen was.Why did I pick the bunny suit!!? Charlie carefully placed a hand on my leg, squeezing the nylons, those big eyes of his staring right at me. I gulped, completely surprised at how forward he was being, but somehow being entirely okay with the direction this evening was heading in.

He chuckled, his hand never stopping rubbing and gripping my thigh. "I just wouldn't have thought in a million years you'd be so beautiful. Especially, you know, because normally you're..."

"Don't you dare finish that sentence." Another chuckle, feeling myself starting to lean into my friend, my submissive nature taking over, melting from his firm touch on my leg. Charlie patted my leg encouragingly, beckoning me over to his lap, to my surprise I did so without hesitation. I wrapped my arms around his neck, feeling his hands holding my legs and ass, continuing his squeezing and rubbing, tiny moans already escaping through my hastily painted lips.

He stared at me. "Rory, I don't really know what's happening. You know it's been a while since I've been with someone, but man am I turned the fuck on by you right now." I blushed, brushing a few strands of my wig back that had escaped my ears, confidence growing being in his arms. Staring down at him, I took a leap, a terrifying leap, leaning in to kiss him. Charlie offered no resistance, our tongues immediately entwined, my moans filling the room.

Pulling away from him after a few minutes, I giggled, my poor clit straining harder than it had in a very, very long time. "Maybe we just...go with it?" Charlie, a little out of breath, laughed.

"Yeah. Go with it, I like that. Now please kiss me again." I didn't need to be asked twice, smushing my lips against his once more. I whined when one of his hands stopped its wonderful groping of my nylon thigh, moving between my legs in search of my clit. Whimpering, I tried to stop him half-heartedly, but Charlie persisted, patting my ass encouragingly. Relenting, I opened my legs slightly, shaking as I felt him start to rub and trace my cage with his finger.

"Are you going to let me see what this is yet?"

"Mmmmmmm, nope." I giggled, feeling that brattiness of mine starting to surface. "That is a secret I shall be keeping, thank you very much." I placed my hands on either side of his head against the couch, planting a final kiss on his beautiful lips. Smirking down at him, a surge of confidence and excitement running through my body, I slowly sank down between his legs on my knees. "However, maybe I can help you forget about it..."

Charlie's eyes widened, and for the first time of the evening I felt as if I had the upper hand. He offered no resistance, watching as my fingers made quick work of his belt, stripping him of his jeans. Just like that, our playful friendly dynamic had shifted completely, as Charlie's big cock was right in front of my face. I ran my hands along his thighs, making sure this was what he wanted, knowing how desperate I was to please him.

"Would you like me to suck your cock?" I watched him gulp, only able to nod eagerly, seeing the excited nervousness in his face. With a giggle, I started with a kiss, planted on the head of his cock, watching it twitch in response. Kisses turned to licks, my hands finding his shaft and balls, falling into the role that I loved, the perfect sissy cocksucker. Charlie gripped the couch, groaning above me, as he watched his cock disappear past my lips.

"Oh fuck. Fuck. Fuck. Fuck. You are so good at that. Fuck. Please don't stop." I smiled around his cock, amused that he had finally found his voice once more. Charlie put his head back on the couch, my hands encouragingly rubbing his thighs as he had done for me, rubbing his cock against my tongue as my lips held him tightly. He had a yummy cock, and I wasn't letting it go anywhere.

I pouted when he said he was going to cum, thoroughly enjoying playing with him. Taking him out of my mouth, I cherished the frustrated groan escaping him, staring down at my smirking face. "Why did you stop? Are you okay?" I giggled, gently stroking him enough to stay near the edge, but nowhere near to cum.

"That's for buying me a tutu."

"What? That was a joke! This is just mean!" I shrugged, continuing my slow strokes.

"You were mean first!" I teased, enjoying finally having some sort of control. He growled at me, staring down at his friend's grip on his cock. A stern look spread over his face, instantly making my clit strain, worried I might cum from that alone.

"Rory, you make me cum right now, you little tease." I giggled again, sighing that he hadn't picked up on just how much of a brat I was in these mindsets. Locking eyes with him, my hands never stopping nor changing pace, I said two of my favourite words in the whole, wide, world.

"Make me."

I gasped as he shot up from the couch, whimpering as one of his strong hands cupped my chin. Holding my head steady, he pushed his cock firmly past my lips, encouraged by my moans as I sat back on my heels like his good girl, feeling him slide in and out of my mouth. Groaning, it didn't take long before he was back to needing to cum, now fully in control. He gripped his cock in his left hand, still cupping me with his right, shaking as he steadied himself.

Giggling, I got the hint, holding out my tongue, mouth wide opened, as he emptied himself all over me. I felt his cum start to shoot in my mouth, completely coating my tongue with that warm, yummy, familiar taste. I eagerly watched him as he moaned through his orgasm, using me for his entertainment, my eyes batting up at him while he did so. Waiting patiently for him to finish, he sighed, wiping the final remnants of his cum off on my lip, staring down at the sissy bunny before him.

"Holy fuck, that was amazing." I giggled, my mouth still full of his cum. Making sure he was watching, I happily swallowed my friend's cum for the first time, the warm thick liquid not even making me gag. With another giggle, I went back to his cock, dutifully cleaning it of any leftovers, including a few drops that had escaped onto my cheek. He sighed, content and exhausted, his hand still cupping my chin tenderly.

Leaning down, so close to my lips, listening to my tiny little whimpers, Charlie stared directly into my eyes. "Now that I know about Rory, I will be playing with her a lot more." I blushed, completely at his mercy, melting underneath his stern, controlling voice.

"I'm uh, okay with that. Like super okay with that Charlie." He chuckled, shaking his head as he held me.

"No no, Rory. Charlie is your friend, the one you play hockey with and drink beers together." Leaning in, he planted a tender kiss on my lips. "Right now, in these moments, I am your Daddy." I whimpered, almost a hundred percent certain a bit of cum shot out of my cage, nearly fainting from excitement.

"Okay Daddy..."

I sucked Ch-Daddy's cock two more times that night, lying on the couch with him in my mouth, his hands gripping and spanking my ass. It didn't feel weird, didn't feel too fast, or awkward that we were friends. It just felt right, me being Rory and him being Daddy. As he left me with the heavy taste of his cum on my lips, his touch seeming to linger on my body, I fell asleep with the biggest smile on my face, my clit happily straining away, reminding me just how exciting the entire night had been.

I saw Charlie a few days later, and we awkwardly chuckled at each other with me back in boy mode and him back in...non-Daddy mode? We were going to need a name for that. But thankfully nothing had changed, both of us able to keep that night separate from our friendship, still the same dynamic as before. After all, it's not every teammate who's seen me in a cute pink bunny suit...with my lips wrapped around his cock.

True to his word, the next night I found myself wearing a cute red dress, white polka-dots and ribbons all over it, with white tights and heels, playing the good housewife as I sucked his wondrous cock after work. After cumming hard down my throat, holding my hands above my head while he used me how he saw fit, I pounced in his lap to kiss him, moaning like a desperate little slut, grinding against his thigh.

Out of breath, wild with an aching need to cum, my clit strained aggressively underneath my dress. Sensing my frustration, Daddy reached underneath me, cupping my cage through the silky panties I had chosen, most definitely wet from my excitement. Blushing, I whined as he rubbed, explored, and squeezed my cage, clit responding from being fondled. Holding onto his shoulders, I arched my back, shuddering from being touched.

Pulling me back down, pinching my chin to hold me close to him, Daddy ensured he had my full attention. "Now, tell me all about this little thing, baby girl." I blushed, trying to escape away, but he held me in place, knowing I had nowhere to go. Pouting, I relented, telling him all about being caged, how it made me feel, turning me into a good girl, a desperate, needy mess. Somehow helping lock away my masculinity.

Daddy simply smiled as I blabbered on and on, interrupting the odd time but mostly letting me talk, drinking it all in. When I finally finished, pouting at him for making me tell him everything, Daddy just kissed me, thanking me for sharing. "Good. Then I want you caged whenever I see you. And I might be requiring it at other points too." I whined, begging him not to do that to me, but internally I knew how amazing this felt to lose control to my friend. Fuck I wanted to be his little slut so badly!

Another long night of cuddling and being his cocksucker, I tossed and turned in my stockings and cage, my clit aching to cum as I drifted off to sleep, tormented by my own imagination. The vague threat of him caging me randomly driving me insane, terrified just how far I would go down the sissy rabbit hole for my new Daddy.

A few nights later, Charlie let me know that I'd be getting another visit from my Daddy, and to be ready. True to his word, I spent two days caged in anticipation, the aching desperation starting to build inside of me. Blushing the night of, I even gave myself a thorough enema, wearing my very best princess plug. I had no idea if he had any interest in fucking me, but I felt like if I didn't give myself the option my clit would kill me in retaliation. Dramatic little thing.

Wearing some white hold up stockings, silky elbow gloves, and a tiny waist corset, I nervously awaited his arrival. Legs crossed, heels pushing my ass up seductively, I stared over my shoulder as he walked in, immediately staring at the view I had been planning for him all evening. Knowing he could see the plug inside of me, so much of my sissy body on display, I bit my lip as I giggled.

"Hi Daddy."

He laughed, "Oh you little fucking shit." I squealed as he spanked me a few times, gripping my throat from behind before kissing me, moaning as I fell against his chest. His other hand moved down to my clit, rubbing and feeling how desperate I was straining, how eager being caged for him had made me. "Did you enjoy being caged for tonight?"

I huffed at him. "No!" But my stern demeanor didn't last long, soon blushing underneath his smirk. "Okay, maybe a little." Daddy laughed, patting my ass, kissing me on the cheek.

"That's what I thought, my little slut." I moaned, his fingers not stopping, soon grinding my ass against his growing cock. He pulled me tightly into him, biting my ear as he began to whisper. "I've been thinking of you all week, Rory. Thinking of what a good girl you've been for me so far. Thinking of how I want to make you cum tonight."

I whimpered, my legs nearly collapsing hearing him say that. "I get to cum, Daddy?" He nodded, planting little kisses on my neck.

"Yes, baby girl, you do." I squealed, feeling as if my clit would just cum then and there. His fingers rubbed my cage, forcing my back to arch into his body, moaning from being touched and played with. I could feel the strain between my legs, the eagerness and need that had built up over two nights being caged. Two nights of tormenting, wonderful dreams, waking up aching and desperate, wanting nothing more in the world than to be used, commanded, and fucked by my new Daddy.

Barely able to breathe, I simply whimpered in his arms while he ramped up that ferocious frustration coursing through me. Turning me around, my heels towering over him, Daddy pulled me in for a deep, tender kiss. I felt myself completely fall under his control, ready and willing for whatever he had planned for me, just there to be his good girl. A leap into subspace, at the hands of someone I trusted.