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.
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