paddedlittleparadise
patreon
Sugar and Spice and Everything… Naughty – Part One
🕑 Added 2021-12-04 00:01:01 +0000 UTC"You can't be serious, Hannah. Really?"
Rory slid from under his girlfriend's arm and gave her an exasperated glare. "I mean, don't get me wrong – I'd love to spend the holidays with you! It's Christmas, after all, and your birthday, too. But you really think I'd be willing to- to-"
Hannah flashed a smile and laid one affectionate hand on Rory's shoulder, stroking reassuringly through his shoulder-length black hair. "Relax, bud! It's not that big a deal, okay? Listen: it's just to keep my parents happy, okay? Please?" She bent closer, her blue eyes pleading. "I really don't want them freaking out – and believe me, they'd definitely freak out if they knew I was dating a guy without their permission…"
Rory frowned. "Hannah, I dunno. I mean, what kind of folks don't let their twenty-three-year-old daughter date whoever she wants?" "Whomever," Hannah corrected with a toss of her dirty blonde hair. "And my fucking conservative-ass folks, that's who." She heaved a little sigh, her eyes traveling thoughtfully down to the worn carpet of her little apartment. "Listen, I guess I don't talk about it much. But I'm from a crazy conservative community, Rory. I know you think you know what old-fashioned means… but lemme tell you. You ain't seen nothing…"
Struck by her suddenly melancholy tone, Rory scooched back closer. "Well, okay, maybe not. But maybe if you'd tell me, babe? Like, what? Do they still think some bearded dude up in the sky created the world in seven days?" He snorted at his own attempt at humor, but stopped short in surprise at Hannah's next words. "Well, actually, yeah. And that men and women shouldn't work together, or sit together in church. And that the radio and the TV and smart phones are sinful devices of the devil. And of course that sex before marriage is absolutely horrible…"
Rory scratched his head in confusion. "Wait… really? You're serious?" "Dead serious," Hannah nodded, rising and motioning him to follow her into her little bedroom. "Come on, there's something I want to show you." She swung open the door to her closet, then thrust the row of halter tops and t-shirts and tattered blue jeans to one side. "That's all my normal stuff, of course. But over on this side…" She motioned at a handful of oddly-cut, floral-printed dresses that reached down perilously close to the carpeted floor. "Well, that's what I wear the rest of the time… when I'm not here at med school."
Rory eyed them curiously. "Wow – just, wow. You really wear those?" "Have all my life," Hannah affirmed, plucking a light blue one off the hanger and holding it up to herself with a lopsided grin. "How do I look, hmm? Not quite the edgy chick you thought you knew?" To which her boyfriend, glancing from the high, simple collar to the wrist-length sleeves and down to the skirt hem that was brushing against her ankles, could only chuckle in disbelief. "Um… yeah? Good god, it's like something out of Little House on the Prairie!"
"Now, don't you be laughing too hard, mister," Hannah cautioned – and now the knowing smirk was back on her rosy lips. "Like I said: if you want to come home with me, you'll be wearing one, too! And believe me, I think you're gonna look amazing…"
The plan was simple, and devastatingly logical – for the most part. Hannah had explained it all. She was dating Rory without her parents' knowledge because they simply wouldn't have allowed her to date anyone not from their church. She couldn't possibly show up with him as "just a friend" – all the neighbors would talk, and her parents would be suspicious no matter what she said. The only way, she insisted with not a trace of irony in her voice, was to have Rory dress as a girl… for the entire two-week holiday.
"Go on, strip," she urged now, playfully dealing Rory's rear a little smack. "I wanna see just how sweet my pretty boyfriend looks in one of my dresses!" Rory opened his mouth to protest, but found the spirit only to mutter a few choice words and screw up with mouth in distaste. "Oh, come on!" Hannah smirked, watching in amusement as he grudgingly slipped out of his jeans and began tugging his t-shirt over his head. "Babe, I happen to know you're more than happy to wear things that are way more embarrassing than one of my dresses. Let's see… how long ago was it that you told me about that crinkly underwear you like to wear sometimes?"
Rory flushed, as much from mortification as from the exertion of shrugging out of his clothes. "Hey, you said you wouldn't make fun of me!" he spluttered, to which Hannah only giggled and patted his cheek. "Oh, of course not. But I also like how red and embarrassed you get, babe. You do like it when I tease you, don't you? You silly little baby!"
Maybe it had been Hannah's strait-laced upbringing, Rory mused now as his girlfriend's laughter rang in his ears. Maybe not. But damn, it never failed to surprise – and yes, secretly delight – him to see just how spectacularly kinky she was.
"Aww, look – Mister Jellyman's out to play!" she tittered as Rory grudgingly tugged down his briefs and revealed his slender, dangling member. "You know, that reminds me – I think there's one or two more things we're going to need to do before we go. Lemme see, I think I've got just the thing…" And then she was rummaging in her nightstand while the naked Rory looked on, more conscious than ever of how pale and slender and un-muscular his body was. Good grief. Maybe he really could pass for a girl…?
"Aha, here we go!" Hannah flourished a shining metal device and swept back to her nude boyfriend. "See, there's just one little problem with dressing you like me, babe. If someone catches on and suspects you're actually a guy…" She shrugged and glanced pointedly at his flaccid penis. "Well, my parents will hit the roof. They'll be thinking we've been fucking every night dusk to dawn-"
"And hey – maybe we are!" Rory declared defiantly, edging nervously back from the odd device in his girlfriend's hand: a device he'd never seen in real life, but which he recognized all too well. "What of it?" "Rory, come on!" Hannah exclaimed crossly, tugging him back and dropping to one knee with a look of firm determination. "Now, look. I don't make the rules. I'm just saying that if someone finds you out, it's gonna be way more easier to explain if I can show them we've got this naughty little fellow…" and here she tucked the device under his shielding fingers and slipped it firmly over his limp shaft.
Click. "…locked away."
Oh, Rory protested at that. It was stupid. Medieval. A torture device. Why the hell would he put up with such a weird, crazy- But Hannah only smiled, fingers working dexterously all the while. And before Rory quite knew it, she was straightening up, and the heavy metallic weight of his new chastity cage was now hanging between his legs, tight and cold and hopelessly secure.
"Hush with your whining, you big baby!" Hannah exclaimed, shaking her head in exasperated merriment as Rory began trying to tug peevishly at the cage. "Now, listen. I know it's a bit of a pain. But first of all…" and she bent closer and planted a kiss on his protesting lips, "I personally think it's hot as hell. You wouldn't want to deny your girlfriend a fun time for her birthday, would you?" Rory grumbled and sighed, but she went on even before he could form an articulate response.
"And secondly, babe, I know you're gonna deserve a treat for putting up with it. I know it's not easy, not getting to cum for an entire two weeks." She stepped back and met his gaze with a twinkling eye. "So that's why I've decided. You're going to come along with me as my sweet female friend… a friend who also just happens to be incontinent."
Rory's dark eyes grew wide at that one. But once Hannah had stopped giggling, she'd explained it all – again, so logically that he had no way to reasonably object. "Babe, you know as well as I do that you've got a bulge down there – and that cage only makes it bigger. I know these skirts hide a lot, of course. But pajamas don't. And believe me, the last thing we need is a hard little clunk every time you sit down on one of our wooden dining room chairs for dinner…"
"So your solution is diapers?" Rory's voice was trembling with mingled agitation, arousal, and fear. "No, babe, please! I know you like to be kinky and all. And yeah, I guess I do kinda like them. But if your parents are so freakin' old-fashioned-" "All the more reason to hide our kinky sides right in plain sight," Hannah declared, stepping over and pulling a neatly folded diaper from the depths of her closet. "Trust me: if they think it's for medical reasons, no one will suspect a thing. Now, go on. Lay down while I put this on you, little man. Or should I say, 'little girl'…?"
And so it went: first the diaper, thick and bulky around Rory's imprisoned and suddenly straining cock. Then a generously padded bra, and a ruffled cotton slip, and pantyhose over his legs and up around the bulk of his diapered rear. And then, at long last, the dress: absurdly long, all in pale green cotton, with a high collar and the simplest of long sleeves and a zipper running up the back to seal him firmly away into his new feminine garb.
"Oh, my word, you look fucking amazing!" Hannah was beside herself with glee as she finished tugging the zipper up into place. "Now, we just need to do something with your hair. Thank goodness you've been growing it out…" And then before he quite knew it, Rory's hair was being parted down the middle and briskly combed into two matching dark plaits, one on either side of his head. "I know Asian hair's kinda tough to work with, but I really think it's gonna work," Hannah murmured, almost as if to herself. "Now, just a little bit more…"
Then it was done. And as the beaming Hannah led Rory, sweating with nervousness, over to the mirror, he found himself transfixed by the reflection before him. For Rory the boyfriend was gone: erased as if by magic. In his place there stood an awkward-looking young woman, looking for all the world as though she belonged on a nineteenth-century farm tending geese. He tilted his head uncertainly, half horrified and half mesmerized by the weighty swing of his new braids and the rustle of his long dress. So long, so plain, so completely feminine…
Well, at least the rustling, voluminous skirt effortlessly obscured the crinkle of the bulky diaper beneath. That was something, at least.
"Ooh, you're incredible!" Hannah squealed… and Rory flushed as she pulled him into a gleeful embrace. "Rory, you're absolutely perfect. And I promise: we're gonna make this the most crazy fun holiday you've ever had."
Fun? Rory wasn't quite sure what sort of fun she had in mind. But despite his anxiety, he couldn't deny that he too was beginning to wonder, with a certain degree of excitement, just what sort of kinky adventures she had in store for them…
Comments
Paul Bennett
I'm looking forward to how this will continue. Thanks for sharing.
