Sissy vs Sissy vs Sissy Part 3

 5/25

“Wait!” Jared burst into the room in a mass of fabric and curls. In contrast to Rory’s scantily clad approach, he was awash with folds of satin and wearing an ornate flowery headdress atop a dark blonde wig. “I am Aunt Clarissa’s most adorable little sissy. Her fortune is mine!” He attempted to stride towards the still seated Mr. Gregory, but the hem of his long dress caught between his high heels and he stumbled headlong into the opposing wall. Anna watched as he balanced himself and slowly looked up into a round mirror that was hanging there. It was as if he didn’t recognise the cosmetic laden face staring back at him and she got flashbacks of the first time she had seen Jared feminized all those years ago.

“You’ll need a lot more than a pretty dress to prove that!” Rory had dropped his gown back over his inked ass and was now facing off across the room at Jared like a gunslinger in stilettos. “She branded me because I was her favourite,” he spat, “you are just…” he turned to face Anna too, “…both of you, you’re just a pair of wannabes.”

“Not true!” Jared pushed himself off the wall. “Not true at all!” He tottered over to the desk where Mr. Gregory was seated with a face full of shock. Reaching the urn, Jared suddenly lifted the folds of his skirt and pulled something from the waistband of a pair of silk panties. “This is my proof!” He dropped a pile of official looking papers into Mr. Gregory’s tray. “That is a contract. No, it is a deed! It names Aunt Clarissa as my official owner and conservator and states in ink that I and only I, am her one true most adorable sissy and heir!” The room fell into a stunned silence as Mr. Gregory slowly picked up the papers and began to leaf through them. Anna kicked off her own heels and padded over to the desk.

“Is it real?” she asked the executor.

“Seems legal and binding…” he replied, his eyes never leaving the page in front of him. Things happened in a blur after that. The door to the office flew open once more and Rory and Jared stared in horror as Aunt Clarissa entered the room. Rory reacted quicker but still too slowly and when he turned to retrieve the keys to his bonds, they were already nowhere to be seen. He whirled back around to see Anna snapping a kind of leash around Jared’s neck. It only served to distract him as Aunt Clarissa clipped one around his own throat while Anna scooped up the legal documents from the desk. A soft tug on the chain was enough to bring him off balance and to his knees beside an equally helpless Jared.

“Rumours of my demise and all that jazz!” Aunt Clarissa cackled gleefully high-fiving Anna, who had already begun to remove the dress she clearly resented wearing. “It has been a long time, hasn’t it my little sissies? But don’t worry, I still have all my old toys!”

Whatever Happened to Mason? (Creative Control)

 Original Caption 

Mason was still in his cheer uniform as he started sobbing. He didn't care how he looked dabbing his tear streaked makeup with a handkerchief. He was so far past that. Next year. The words echoed like a sentence. He’d be here another year, and maybe another after that. Every semester pulled him deeper, erased more of the boy he’d been.

The college acceptance letter should have felt like a victory – an escape from his high-school cheer hell where his ex-girlfriend's mom had sponsored the squad and insisted on a new all female image. The college had given him a full ride. A cheer scholarship. Now, as he cried tears of frustration at the end of his senior year, he remembered sitting cross-legged on his bed, reading that letter, the words blurring on the page. His stomach knotted tighter with every sentence he reread.

The scholarship hadn't just been for him. It was for the squad. For the all-female squad. The same one his ex and her mother had orchestrated to trap him in this nightmare. His squadmates had arrived at school the next day, squealing. “We made it!” “Can you believe it?” “Free college!” They crowded around him, spraying glitter hairspray, already planning Instagram posts about a scholarship that, as much as he wanted to, he knew he couldn't turn down.

And now, thanks to his grades, he was trapped for another year.

He shoved the handkerchief aside and looked at himself in the mirror across the room. The reflection that stared back wasn’t the swaggering boy who’d once strutted down the halls of high-school with Tanya on his hip and Carly watching him admiringly from near the lockers. Instead: smooth legs, spankies under a pleated cheer skirt, hair fully grown out into a feminine style. A girl. A convincing one.

All those late nights practicing the “female” parts of routines had wrecked his coursework. He knew how to nail a perfect herk and keep his lipstick from smudging mid-chant — but he couldn’t tell you the last time he’d finished a physics assignment. The balance had tipped, and the scales weren’t ever coming back.

Another year, he thought miserably. Summer would fly past and fall would come quickly. Another year of tucking his crotch so when he cartwheeled, noone could see the bulge in his spankies. Another year of half-time shows. Another year of group photos with the football team.

A professor looked his way and he forced a smile, the kind he’d perfected while waving pompoms and doing high kicks, the kind that made his jaw ache, and the truth pressed down like a weight: he wasn’t just pretending anymore. The squad wasn’t letting him go, and neither was the scholarship. His future was sealed in spandex and glitter for another year...at least...

Doll House Arrest Part 3 [COMMISSION]

 

Lola had been the one to wear stripes criss-crossing a tiny mini-dress. She hummed like it was Christmas morning. “Showtime, doll,” she whispered following a stern knock on the door. Frank’s gut clenched.

The door swung open, revealing Detective Finn Collier - young, straight=laced, and his mouth dropped open at the sight of the two beautiful blondes. His eyes flicked from Lola to Frank, and then quickly away, as if staring too long might burn him.“Afternoon, ladies,” Finn said, already fumbling his notepad. “We’re following up on our search for a fugitive.” His gaze darted to Frank again, then skittered away. “I believe one of you was in a relationship with him?”

Lola gasped theatrically, clutching Frank’s hand. “That was such a long time ago. I have moved onto better things now...though I still swing both ways, you know?” She winked and glanced surreptitiously at the studio apartment's double bed.

Finn’s cheeks turned scarlet. “No, miss, I— I didn’t mean—” Frank fought to keep his face neutral. His palms were sweating. Lola’s nails dug warningly into his still clutched palm.

He forced a nervous laugh. “We, uh… we’ve just been keeping to ourselves.” His voice sounded higher, softer than he remembered. Lola had drilled him for a week, and damn it, it worked.

“Oh, yes, how rude of me,” Lola said sweetly, squeezing Frank’s hand even harder. “This is my girlfriend. My everything.” She turned to Frank, eyes sparkling with mischief. “Aren’t you, darling?” Lola leaned forward giving Finn an eyeful of cleavage. “You seem tense, detective. Are we making you nervous? Because we could help with that.” She smirked wickedly, pulling her hand from Frank and swatted him hard across the ass. She then slid an arm around his shoulders. “We’re very… accommodating.”

Frank forced what he thought was a flirtatious grin as his last bit of dignity trickled away . His heart hammered in his chest and Lola’s nails grazed the back of his neck. He forced a shaky wink at Finn. “She’s… not kidding. We, um, like to have fun.”

Finn nearly dropped his pen. “Oh! I—uh—no, that’s— I mean, I should go—” He nearly tripped over his feet, as he turned to the door “Thank you for your time, ladies. You’ve been very helpful.”

Lola waved sweetly as he bolted out the door. The moment it shut, she collapsed into hysterical laughter, clutching her stomach. “Oh, sugarplum! Did you see his face? He thought he’d walked into his wildest dream—or his worst nightmare!”

Frank slumped back, trembling. His reflection in the mirror across the room mocked him: flawless makeup, long lashes, glossy toned legs extending from a patterned figure hugging minidress. He was no longer a fugitive No longer even a man. Just a doll. Lola's doll.

Lola cupped his chin, forcing him to meet her glittering eyes. “See? You pulled it off. You’re all mine now. I can tell the world who you are and they will believe me. You want me to tell them you're my doll...or something else...?”

Frank felt the last of his fight drain away. He was perfectly trapped. “No... I'm your doll...” he whispered.

Doll House Arrest Part 2 [COMMISSION]

Frank adjusted the hem of the dress for the fifth time that morning, though it didn’t need it. The shiny fabric clung like it had been painted on, showing every contour he’d rather forget he now had. His legs — smooth and tanned, looked like they belonged to somebody else entirely. His reflection in the mirror didn’t look like a fugitive. It looked like a woman about to cause a traffic accident.

He groaned. “I don’t know who that is, but it’s not me.”

Behind him, Lola squealed and clapped like a proud mother. “Oh, it’s you, sugarplum. The real you. My vision, brought to life. My doll! You’re a masterpiece. Admit it.” She circled him like he was a museum piece, tugging at his hair extensions, smoothing his foundation. “Do you hear any sirens? No? That’s because nobody’s looking for a big bad bank robber anymore. They’re looking for John Doe with a shotgun. Not Jessica Rabbit in stilettos.”

Frank winced at his own reflection. A week ago he’d been a man on the run. Now he looked like a centerfold. He hated how convincing it was. Even more, he hated that part of him understood exactly what Lola meant.“This is insane,” he said, softer this time. “I can’t stay like this forever.”

“You’ll stay like this until I’m finished,” Lola sang, twirling past him to pluck a leather purse from the dresser. “And when will that be, you ask? When I’m bored. Which, spoiler alert, is never. You’re mine. My doll, my girlfriend, my—” She leaned close to hand him the purse, her eyes psychotically giddy to Harley Quinn proportions, lips brushing his ear. “—perfect alibi.”

Frank stiffened. “Alibi?”

She smiled, wide and unblinking. “Oh, I didn't mention? Tomorrow, a detective is coming over to ask little old me if I’ve seen a certain dangerous fugitive ex of mine. Isn’t that exciting?”

Frank’s stomach dropped. “You can’t be serious.”

“Oh, but I am!” She kissed his cheek, leaving a smudge of lipstick. “And when the nice detective walks through that door, do you know what he’ll see? Not Frank the bank robber. Not my runaway coward. He’ll see my stunning girlfriend. Polished. Perfect. Untouchable.”

Frank stared at the door, expecting in to burst open any moment – police filling the room. “Lola, if I slip up—”

She shushed him with a manic giggle. “You won’t. Because if you do, darling… you’ll go to prison. And between you and me? Stripes don't suit you.” She flitted toward the mirror again, admiring the two of them side by side — her in her bubblegum robe, him in the glossy figure hugging dress. “Tomorrow, sugarplum, you make your debut. And if you’re a good girl…” She winked. “I might even let you pick the earrings.”

Frank felt his stomach twist into knots. Tomorrow. The cops. Despite what Lola said about them being together, he was completely alone – with so much to hide...and what chance did he have if she kept putting him in such revealing outfits...

 

Doll House Arrest Part 1 [COMMISSION]

 A commission I did on DeviantArt

Frank adjusted his position on the floor, tugging at the top of a shiny high-heeled leather boot that stretched right over his knee. “This,” he growled, “is not a disguise. This is entrapment.”

Across from him, Lola lounged in a silk robe the color of radioactive bubblegum, sipping wine at ten in the morning. Her eyes gleamed like she’d won the lottery. “Oh, hush. Nobody’s looking for a sexy blonde with great calves,” she said. “This is a safe house!”

“This is a doll's house!” Frank threw her a look. “ And you’re insane.”

“Correction,” she chirped, leaning forward so her robe slipped suggestively. “I’m an artist. And you, darling, are my medium. I always said you’d look great with a ponytail. You just never listened. Besides where else were you going to go?”

Frank groaned knowing she was right, burying his cosmetic laden face in his hands. “This is exactly why I left you. You were trying to turn me into your...your plaything. It was like an obsession. It was like...like...”

“Foreplay,” she said. “And then you ran out on me mid-project. Very rude.”

“Can't you at least take this seriously, you crazy bitch!” Frank sat up, snapping, “I robbed a bank, Lola. The cops are everywhere. I didn’t exactly have a choice where to hide.”

“Oh, so I’m your last resort?” she said, pretending to pout, then grinned wickedly. “Romantic...for me... To you it is survival. And survival, sugarplum, costs extra.” She tapped her wineglass. “Let’s talk about that money you're going to share. You know? That big bag of cash in my kitchen. You ran out on me Frank, no postcard, no flowers, not even a text. And now—poof!—here you are, desperate... begging for my hospitality...well, you are going to have to pay for it!”

Frank stiffened. “You're not getting a dime!”

Her laugh was high and musical, but her eyes never blinked. “Oh, sweetheart, it’s all mine. I’m keeping you out of prison. That’s a full-service package. Besides”—she flicked a lock of his blonde hair behind one ear—“this is just phase one. Doll-making isn’t cheap.”

Frank glared at her. “You can’t be serious.” She pulled out her phone and snapped a picture before he could stop her.

“Insurance policy. If you get any clever ideas, imagine this on Instagram...or OnlyFemmes. ‘Bank Robber Chic’.” She giggled so hard she snorted, then clapped her hands. “Oh, I missed this. I missed us. You squirming, me improving you. Just like old times.” Lola leaned in close, her perfume a heady sugar rush. She patted his knee, nails clicking. “Now rest up, doll. Tomorrow, we get serious. You didn't think we were going to stop at a pair of pretty boots and a woollen peacoat did you? Especially not now I have a shopping budget!””

Sissy vs Sissy vs Sissy Part 2

 4/25

It was Thursday and Anna waited uneasily in the study of her Aunt’s old house. The guys hadn’t turned up and the grandfather clock in the corner ticked loudly. Her only other company was Mr. Gregory, who sat at a large mahogany desk – Aunt Clarissa’s urn at one hand and a wooden tray of legal papers at the other. Anna squirmed before him in the same prissy blue dress she had adorned two days earlier. She hoped this would be worth it and silently wondered if her own preference for baggy jeans and hoodies and factored into her taking so much vicarious pleasure from her Aunt’s torment of Jared and Rory all those years ago.

Four o’clock approached and, without warning, another figure slipped into the room. Swanlike, but without an ounce of the matching graceful pride, a feminine creature dripping in beads and lace traipsed across the study in pearl covered high-heels. Freshly adorned hair extensions swooped across a painted face and Anna caught a glimpse of the unmistakeable grimace of Rory.

Unable to hold her gaze, the feminized man turned and loped towards the seated, and now heavily blushing Mr. Gregory. Rory pulled a thin beaded necklace from around his neck and Anna saw that it held a ring of tiny keys at its centre. The sissy bent forward, a pained expression crossing his lips and slowly used one key to close a lock on one of his platform heels before using a different key to fasten the other. Standing back up, he used another to lock the back of his tightly wound corset and then with a final flourish, he pulled up the front of his flowing dress and locked what was beneath.

Anna felt at pang of disappointment that Rory wasn’t wearing panties as she watched him place the keys atop Mr. Gregory’s box of legal documents, but seeing the tiny cage that the prissy bitch had stuffed his genitals into and now locked, more than made up for it.

“That’s your proof?” Anna smirked. “That proves nothing except you are willing to humiliate yourself for money. Any sissy bitch with an OnlyFemmes account can do that.”

“No…” Rory seemed to blush even redder, “this is my proof.” He turned and this time raised the rear of his gown and Anna’s mouth dropped open. The head of baby pink buttplug winked from between his ass-cheeks, pressed tight from his position atop the towering heels – “Most Adorable Little Sissy” scrawled across it. He’d gone even further than she expected, but did the anal toy really warrant his obvious pain? She had seen her aunt use bigger on him countless times. And then her eyes shifted and she saw it. Rory had made a mistake wearing fishnets that went all the over his backside. With every small movement the white fabric moved – raking over the freshly tattooed ink emblazoning “Property of Lady Clarissa” from his left butt cheek.

Hood Ornament [COMMISSION]

 This was DeviantArt commission

“Wasn't there some guy who tried this already?” Devon squirmed in place. He was trying to rest himself on the truck in a way that supported him without burning his bare skin on the sun-beaten chrome. “OnlyFemmes I mean – didn't he pose as his girlfriend or sister or something, and she ended up putting some kind of sissy bounty on him?”

“Don't give me ideas,” Haley, his long-suffering girlfriend, spat, pointing the camera at him, “I still need to pay off that lemon,” she nodded at the flame-streaked vintage truck Devon had spent their entire savings on, “the last thing I need is to pay off some crazy bitch with whips and chains for punishing my idiot boyfriend – as tempting as it is...”

The sun continued to blaze and Devon brushed the bangs of his wig aside to wipe sweat from his brow before it could streak his makeup. The last thing he needed was another hour in front of Haley's mirror while she repainted his face.

“Hey!” He called, suddenly realising something, “shouldn't I be wearing sunscreen? Just seems like after all that plucking and waxing you did, my skins gotta be like super sensitive.”

“Look,” Haley rolled her eyes, “if we're going to be rubbing anything into your skin, it is 100% being filmed for content. Now, pull that swimsuit up a bit higher up your ass – really show off the goods! That's it – now lift up your heels as if you were in stilettos and push out your butt. Nice!” She snapped a dozen pictures in quick succession. “Our subscribers are going to love that!”

“Our subscribers!?” Devon grimaced. Haley's swimsuit was much too small and was wedged uncomfortably between his cheeks. “I don't see you here, half naked and humiliating yourself for...content...”

“That's because I didn't spend all our savings on a supposed vintage truck that doesn't even run. What was it you called it? An asset?” Haley shook her head with derision at the vehicle and her feminised boyfriend together. “Looks like I am photographing all of your assets today... The guy who sold you that thing must be able to spot a sucker a mile off...now there's an idea!” She put the camera down and grinned cruelly. “Stay there while I go and get my dildo. How is your gag reflex by the way?”

Devon groaned. He was starting to miss the idea of the car wash scene Haley had had planned. Frollicking in soapy water sounded like bliss compared to having her sextoy between his painted lips. He just worried where else it would go when Haley found out the money he had paid for the truck was just the down payment.