Naked in the cool air, Andy held up the bra, inhaling its faint trace of Becca's scent—musky, feminine, intoxicating. Mary's voice echoed in his skull, "Clamp it over your flat chest, imagine her firm tits bouncing while some frat boy pounds her from behind."
He hooked the straps over his shoulders, fumbling with the clasp at his back. It pinched his flat chest, the lace scraping his nipples into stiff peaks, a humiliating frill that made his reflection in the mirror look like a pathetic drag queen. His caged genitals dangled below, the steel ring biting into his dick, emphasizing his excitement.
Mary laughed, a sound like tinkling bells, a sound that sent a shiver down Andy's spine. "Oh, Andy. You look so pathetic, so ridiculous. But don't worry, we're just getting started. Now, put on her panties. I want you to feel the fabric against your cock, I want you to imagine her wearing them, I want you to imagine her knowing that you're wearing them, that you're crossdressing in her underwear."
The thong was pure torment. He stepped into it, pulling the flimsy string up his legs. The back vanished between his ass cheeks like an insistent probe, teasing his virgin hole with every shift. The front pouch strained over his confined package, the translucent material outlining the cruel device imprisoning his limp shaft. Precum seeped steadily, staining the spot where it pressed against Becca's stolen thong. He pictured her discovering the theft, her face twisting in disgust as she realized her pathetic brother had soiled her panties with his desperate leaks, jerking to thoughts of her getting brutally fucked.
He nodded, his hands shaking as he put on the bra, as he felt the lace against his skin, as he imagined Becca's body, her curves, her humiliation.
Andy felt a pang of humiliation, of shame. He knew that he had to obey Mary's commands, that he had to put on his sister's panties, that he had to cross-dress, that he had to imagine Becca's humiliation, her anger, her shame. He nodded, his hands shaking as he put on the panties, as he felt the fabric against his cock, as he imagined Becca's body.
Snap. Mary captured the full-body shot, face blurred but body exposed in its degrading glory. "Pathetic. Twirl for me, bitch. And stuff those cups with balled-up socks—fake some udders like the whore you're pretending to be."
Andy obeyed, cheeks burning with humiliated fever, grabbing crumpled socks he had been wearing. He wedged them in, creating lopsided mounds that jiggled absurdly as he pivoted, the thong's string digging deeper into his crack, nudging his sensitive rim.
"Good girl," she mocked and threw him her shoe, hitting him in the torso. "Now hump it. Pretend it's Becca's ass, and beg out loud to watch her swallow a guy's load in her tight cunt. I'll be filming every second."
Humiliation surged like acid through his veins, a toxic mix of self-hatred and lust. He dropped to his knees, pickling her shoe from the floor, the stuffed bra sagging like overripe fruit. Grinding forward, the friction on his trapped dick sent jolts of frustrated pleasure, the string's bite irritating his puckered entrance.
"Please, Mary," he whimpered to Mary, voice cracking, "let me see Becca get fucked. Let her spread those athletic cheeks for a thick dick, let it stretch her sloppy hole while I watch like the useless cuck I am."
His hips bucked wildly, smearing pre-cum across the insole, ass clenching around the intruding fabric. The fantasy ignited: Becca bent over her desk, shorts yanked down, a burly muscled guy slamming into her from behind, her short hair being pulled as she yelped, pussy lips gripping his veiny shaft, cream coating his balls with each brutal plunge.
Suddenly, Mary's hand shot out, snatching the shoe from his grasp mid-thrust. She yanked it away, leaving Andy frozen on his knees, his hips jerking futilely into empty air. His balls throbbed with unmet need, swollen and heavy in the tight confines of the lace panties, the cage around his cock pulsing with denied pressure. Pre-cum dripped steadily from the barred tip, soaking the fabric further, but the abrupt halt left him panting, edged to the brink without mercy.
Mary snapped, "Stop, Andy. You're not to move another inch." Her voice was stern, her eyes flashing with amusement.
Andy froze, his body shaking with need, with desire. He nodded, his voice a mere whisper. "Yes, Mary."
"Look at this, Andy. Look at what you've done. You've stained my shoes so much. You were humping my shoe like some feral dog. You already came close disobeying me again—rubbing that pathetic caged clit to point you came without permission. Andy remember, you don't get to cum. Not now, not ever, not unless I decide you're worthy. Your balls are going to ache for days, leaking like a broken faucet while you beg for relief that won't come. Imagine Becca laughing at you, knowing her big brother is just a denied sissy, blue-balled and desperate, jerking futilely against his prison every night."
Andy's face twisted in desperation, his voice rising in a weak protest. "But Mary, please—I was just—"
Before he could finish, Mary's foot lashed out, her bare toes connecting squarely with his aching balls. The kick landed with a dull thud, pain exploding through his groin like fire. He doubled over, gasping, clutching at the cage as his vision blurred, the sharp agony radiating up his spine. His cock twitched involuntarily inside the metal, a fresh spurt of pre-cum oozing out in response to the brutal denial, but the pain silenced him completely, leaving him wheezing on the floor.
Mary slipped her foot back into the stained shoe without a second glance, the warm leather now slick with his sticky fluid squelching against her sole. She ground her heel down, smearing the mess across her arch, then lifted her foot slightly, dangling the soiled insole inches from his tear-streaked face. "Look what you've done, you filthy pig. My shoe's ruined with your worthless leaks. Now clean it up—with your tongue. Lick every drop of that pre-cum off my shoe first and then my foot, taste your own failure while you remember who owns you."
Trembling, Andy crawled forward on all fours, the stuffed bra dragging against the floor, socks tumbling out and exposing his flat chest once more. He extended his tongue, lapping at the warm, salty residue coating her skin. The flavor hit him—bitter and musky, his own arousal mixed with the faint leather tang—making his stomach churn even as his trapped dick strained harder.
He sucked on her toes one by one, swirling his tongue around each digit, cleaning the crevices where pre-cum had pooled, his cheeks burning with fresh shame. He could feel the texture of her skin, the taste of her sweat, the humiliation, the degradation, overwhelming. Mary's foot flexed in his mouth, pushing deeper, gagging him slightly as she watched with a smirk..
Mary laughed, a sound like tinkling bells, a sound that sent a shiver down Andy's spine. "Oh, Andy. You're pathetic, you're ridiculous, but you're mine. You're my toy, my plaything, my cuckold. And you're doing so well. I'm so proud of you."
Andy licked, his body shaking, his mind a whirlwind of humiliation, of dread, of degradation, of desire. He could feel the texture of her skin, the taste of her sweat, the humiliation, the degradation, overwhelming He felt the pre-cum coating his tongue, the taste bitter, salty, coating his lips, his mouth, as he licked.. He could feel his saliva dripping down his chin, down his neck, a testament to his degradation. He could feel it coating his lips, his mouth, as he licked.
He could feel the pride, the amusement, the cruelty, in Mary's voice, in her eyes, in her smile. And he knew, he knew that he would do anything, anything, to please her, to serve her, to obey her, to be her toy, her plaything, her cuckold.
Finally satisfied, she withdrew her foot with a wet pop, wiping the saliva on his cheek. Standing tall, she loomed over his crumpled form, her voice cold and final. "Listen up, Andy. You're not to cum or orgasm—no matter how bad it hurts, no matter how much you hump your pillow dreaming of Becca's tight pussy getting railed or Stacy's moans as her womb gets filled. I'll know if you do; I'll see it in your pathetic eyes next time. Disobey, and I'll abandon you without a backward glance—leave you locked, alone, forgotten like the trash you are."
Andy, his tongue aching from the humiliation of licking Mary's shoe clean, looked up at her, his eyes filled with a mix of shame and determination. "I... I won't cum, Mary. I promise. I'll keep my balls aching with desire, just like you want."
Mary's face broke into a cruel smile, her eyes gleaming with pleasure. "Good boy, Andy. I'm so proud of you. You're learning, you're obeying. That's what I like to see."
Andy felt a pang of pride, of humiliation. He knew that he had pleased Mary, that he had obeyed her orders, that he had completely positioned himself below her, and that she was proud of him. He nodded, his voice a mere whisper. "Thank you, Mary."
Mary's smile turned wicked, a cruel gleam in her eyes. "But Andy, I can't just let you go now, can I? No, I think you need to earn your freedom. I think you need to prove to me that you're truly committed to your humiliation, to your degradation."
Andy felt a pang of dread, of unease. He knew that Mary was right, that he had to prove himself, that he had to earn his freedom. He nodded, his voice a mere whisper. "Yes, Mary. What do you want me to do?"
Mary's smile turned cruel, a wicked gleam in her eyes. "I want you to keep wearing your sister's thong, keep the bra under your shirt all day feel them rub against you, it'll remind you you're my sissy toy, Andy. I want you to keep feeling the fabric against your cock, I want you to keep imagining her anger, her shame. I want you to keep feeling your own humiliation. And I want you to do this until I come to visit you on the weekend."
Andy felt a pang of shame. He knew that he had to obey Mary's orders, that he had to keep wearing his sister's underwear, that he had to keep feeling the fabric against his cock, feel the bra chafe his nipples. He nodded, his voice a mere whisper. "Yes, Mary."
Mary's smile turned soft, a look of satisfaction on her face. "Good boy, Andy. Now, go home. I'll be in touch soon."
Andy nodded frantically feeling a pang of relief, of unease., scrambling to gather his clothes, the weight of her words crushing him deeper into submission. He knew that he had been dismissed,, that he had to wait for Mary's next commands. "Yes, Mary. I'll wait for you."
His balls pulsed with unrelieved tension as he stumbled out the door, the lace clinging wetly to his skin, a constant reminder of his endless torment. His body aching, his mind a whirlwind of humiliation, of degradation, of desire, he knew that he would never be the same. He was bound by Mary's orders, and he would obey, he would wait, he would serve, until she came to visit him, until she gave him his next commands.