The Sissy (Patreon)

Thanks to our Silver-Tier patron Sam for suggesting a story along these lines!

***

"This is going to be such a big day for you, isn't it, Sissy?"

I'm sure I was blushing at the condescending tone in Jennifer's voice, but underneath all the foundation and blush there was little to no chance anyone could have noticed. I squirmed quietly, shivering now and then at the feathery touch of the makeup brushes caressing my brows, my nose, my freshly rouged cheeks. I had to hold still – let Jennifer have her way with me – submit to her feminizing and infantilizing treatment…

Just like the good sissy she and Kevin had been training me to be these last months.

I blinked, my mind flashing back to the first time they'd brought it up. Jennifer and Kevin were getting an apartment together, they'd told me. Only made sense for two queer, kinky folks like them to stick together, right? And hey – why not join them and help everyone save on rent? It would be a hell of a lot of fun…

I'd known both of them from the events and clubs we all frequented, so it wasn't quite akin to hopping into the white panel van of a wheedling, candy-flourishing stranger. Kevin was a cutie – a "soft boi", as he liked to term himself – and was all about being sweet, and cuddly, and as far as a fellow could be from the stereotype of rough-and-tumble masculinity. As for Jennifer? Well, she'd transitioned years before, and was known primarily for her strong personality, her foul mouth, and the ferocity with which she defended her friends. Oh, and of course her amazing makeup skills.

So when I – a young fellow recently graduated and looking for a place to call home – had gotten the offer, it hadn't taken long before I'd decided to take them up on it. It would be good for me, I told myself. I needed to become more confident, to embrace the queer and sexy and kinky sides of myself that I'd kept locked away deep inside for so long…

It hadn't been more than a week into my new life with them that Jessica proposed it. "Hey, you told me once you're into sissy stuff, right? Like, chastity and plugs and shit like that?" I'd blushed and hemmed and hawed… and then nodded. "Anything else?" "Um, well–" I still remembered the heart-pounding moment when I'd finally stammered out my other secret. "I kind of like the idea of- you know- of, like, baby stuff. You know, d-diapers…"

Jennifer had chortled and patted my back and exclaimed, loudly and proudly, over what a fun and perverted guy I was. "Don't worry, we'll help you out, dear!" she'd winked at Kevin. "If you want, just say the word and Kevin and I will make sure you get all the help you need. I'm sure you'd love to help me train this pretty sissy into a sweet little diaper baby, right, Kevin?"

Oh, he had. I'd stammered out my whole-hearted and blushing consent, and before I'd quite known it my entire world had slid inexorably into the stuff of my fevered fantasies. Day after day, one item after another of my adult masculine wardrobe had gone missing, only to be replaced by the sort of frilly and feminine garments that for years had made my heart pound with mingled joy, adoration, and shame. My few pairs of boxers had quickly given way to flowered and frilly panties. The baggy T-shirts I'd worn as part of my masculine veneer slipped away and returned as tight-fitting crop-tops. And into my closet crept flats and sneakers in the prettiest and most girly shades of blue and pink…

Yes, I was well on my way to being the sissy I longed to be. Not a woman, and not something inbetween, either. Still a self-proclaimed man, but squirming and blushing to be trapped in the beautiful feminine clothes that a flawed society said only belonged to supposedly soft and vulnerable women.

And then the baby stuff had come in. Oh, there was no hypnosis, no accidental bedwetting or punishment, no catastrophic visit to a diaper factory in which the malevolent AI seized me and dragged me down screaming into an incontinent, padded hell. Nothing remotely like those hot stories I'd loved to read for years. No – Jessica and Kevin simply decided one day that I had been big long enough, and that their sissy simply didn't need to be adult anymore. Period.

The first diapers, thick and pink and ever so crinkly, had set me quivering with shame and arousal. I don't think I'll ever forget the sheer pleasure and humiliation that swept over me when Jessica first taped me into a diaper and laughed down at me, calling Kevin over to see what a pathetic little sissy baby I was becoming. "And he fucking loves it, too," she'd chortled, rubbing my diapered crotch suggestively. "You should have seen how fucking hard he was – before I locked him in his diaper where he belongs, of course. Who needs a cage when you've got diapers, am I right?"

The pacifiers and bottles and onesies and frilly baby dresses that followed were the next logical steps, and oh, how shamefully and gratefully I'd taken them on. Not that I had a choice, of course, short of using my safeword. But Jessica wanted it, and Kevin was amused by it, and I… well, I  admit it. I craved it with every fiber of my being. I needed to be a sissy baby. I dreamed of it at night and woke with the sticky shame of my desire in my flowery Goodnites. I longed for it: with every wet diaper I made, and every bottle I drank, and every night I crawled, pink and padded and pacified, into my stuffy-filled bed…

"Hey, Sissy! Go on, what do you say?"

I jerked back to the present, suddenly aware of Jennifer's stern voice in my ear. "You say 'thank you, Mommy, for doing my pretty makeup!'" I gulped and nodded, hastily repeating the groveling words in my best baby voice. "Fank you, Mommy, fow doing my pwetty makeup," I lisped, feeling myself slipping deeper into the role. I'd been made pretty now. I was my sissy self: a strong young man being forced, trained against his will to behave as a pretty baby – a pretty sissy – a pretty little diaper girl all ready for a big day-

And yes, what a big day it was, too! Pride came only once every twelve months, after all, and this parade was the highlight of my roommates' entire year.

"Can we, like, get a move-on?" Kevin called from the hall, glancing pointedly at the clock on the wall. "Parade starts in, like, a half hour!" "Coming," Jennifer responded, tugging me up from my chair with her strong hands. "The Sissy is all ready now. Go on, Sissy. Take a look in the mirror. Don't you just love seeing what a pretty little sissy baby you are?"

I gazed into the full-length mirror at last, feeling the heat rise to my powdered cheeks once more as I took in my bewigged and dolled-up self. Today I was not just a man, not just a sissy, not just a sissy baby. I was a sissy baby cheerleader, replete in the wildly humiliating outfit Jessica had gotten just for me. The bright blue top, tight and uncompromising in its display of my babyish flat chest, came only to my pale and smooth-shaven midriff. The skirt, scandalous in its shortness, did almost nothing to conceal the puffy bulk of my pink and princess-covered diaper beneath. And on my smooth legs, stretching almost up to the knee were brightly striped, pastel knee socks, each proudly proclaiming to the entire world that I was indeed a "BABY SLUT."

I opened my mouth to say something – anything – but before I could find the words I found Jessica cramming a matching blue pacifier deep into my mouth. "You're fucking perfect," she exclaimed, and pressed my two blue pom-poms between my shaky fingers. "Now, then, Sissy. Let's get going! You're gonna look fucking amazing out there!"

Oh, I was going to be a spectacle, all right. Of course, even after all this time a part of me was still unsure. Part of me whispered that no, I should just stay inside – keep this side of me bottled up – let everyone think I was the normal and bland and boring cis male everyone expected me to be. Maybe I should just safeword, change into those boring normal clothes I still kept for work. Maybe- maybe-

But no. I shifted resolutely, staring mutely back into the mirror with a final burst of determination. I might be a sissy baby today – a pretty little cheerleader dolled up and reveling in the glorious humiliation of it all. But simultaneously I was also a strong person: someone who needed and deserved to be accepted for who and what he was. Ironically, I realized with a sudden flash of insight, the act of backing out now would in a way be far more "sissy" – in the sense of cowardly and degrading – than any amount of public humiliation I might earn today.

And so, as I nodded and waddled, crinkling softly, behind my roommates and out the door, I knew despite my instinctual fear and shame that yes, I needed this. Jessica and Kevin had trained me, true. But they were also showing me how to embrace my authentic self, and how to express that in the special, consensual space of our annual kinky parade.

Yes, I would do it. Not simply because I was now their good, obedient sissy baby, but because I was a strong, confident human being… who also just happened to be a sissy baby.