Joe's weight pressed Greg into the pink satin, the corset crushing his ribs with each breath. His stockinged thigh burned where Joe's hand slid upward, palm rough against the nylon, fingers finding the damp heat at the top of his leg. Greg's hips tilted up before he could stop them—seeking something, hungry for something his body knew but his mind refused to name.
"No," Greg whispered. The word came out weak, barely a sound.
Joe laughed, low and easy, and grabbed Greg's wrists. Pinned them to the mattress. His weight settled heavier, grinding down, the denim of his jeans rough against the satin gown bunched between them.
Greg turned his head. Emmy stood at the foot of the bed, half in shadow, her hand sliding between her own thighs. She was watching him. Watching Vanessa. Her lips parted, her breathing quick, and Greg realized—she wasn't just observing. She was getting off. On him. On this. On the sight of him becoming her fantasy.
Joe ground his hips down, his erection pressing against Greg's through the satin. Greg felt his own cock strain upward, trapped and aching, the fabric wet where precum had soaked through. Joe thrust against him, slow and deliberate, the pressure building, building, and Greg's mouth opened on a sound he'd never heard himself make. A whimper. High and thin. A surrender he couldn't take back.
His hips bucked. Chased it. Friction through wet satin, his cock throbbing, the edge closing in—
"Not so fast, sissy girl!"
Emmy's voice cut through. She grabbed Joe's shoulder and pulled him off, and Greg gasped, empty, his cock still straining, aching, denied.
Emmy hauled Greg upright. He sat on the edge of the bed, shaking, the corset digging into his ribs, his cock wet against his thigh. Emmy positioned Joe in front of him. Standing. His crotch at eye level.
"Now," Emmy said, her voice low and sweet, "open his pants, Vanessa."
The name hit like a slap. Greg's cock pulsed. More precum leaked, warm and shameful against his stocking.
Greg looked up. Joe stared down at him, a predatory grin spreading across his face. Greg's throat tightened. He turned his head, searching for Emmy's eyes, finding them. Pleading.
Emmy's face was calm. Matter-of-fact. "This is the deal, Vanessa. You agreed to learn what it's like to be a woman. This is part of it." She paused. "You will suck Joe's dick. You will take Joe in your cunt like a good sissy. And if you're lucky, he will make you cum."
The words landed like stones in his chest. His cock pulsed again. He moaned, a sound of pure humiliation, and the moan only made him harder.
Joe grabbed Greg's head, fingers twisting into the blonde wig, and pulled him forward. Pressed Greg's face against his crotch. The denim was hot, the shape of his erection pressing against Greg's cheek, his mouth.
Greg felt Joe's heat through the fabric. Smelled him. Denim and sweat and anticipation.
Joe pulled Greg's head back, giving him space. Giving him a choice that wasn't a choice. He looked down at Greg, still grinning, and waited.
Greg's hands trembled. The corset pressed against his lungs. His cock ached between his thighs, wet and desperate.
He reached for Joe's belt buckle.
Greg's fingers found the buckle. Cold metal. His hands shook so hard the prongs rattled against the leather. Joe's grip tightened in his wig, holding him steady, and Greg fumbled the belt open one-handed.
"Yes, Vanessa." Emmy's voice came from behind him, low and encouraging, a purr that made his stomach clench. "That's it."
Greg's thumb pushed the button through its loop. The zipper teeth parted under his touch, and Joe's cock pushed against the fly of his boxers—a dark stain spreading through the cotton, the fabric stretched tight. Greg's throat closed. He could smell him now. Musk and salt and heat.
He looked up. Emmy stood beside the bed, her hand still between her thighs, her eyes dark and hungry. He tried to send her a plea with his eyes—please, stop this, I can't—but she only smiled, soft and knowing, and crossed to him.
She knelt beside the bed. Her face came close to his, and for a moment Greg thought—she's going to save me. A wave of relief washed through his chest.
Then she kissed him.
Her lips pressed against his, warm and slow, her tongue sliding along his lower lip. Greg's eyes fluttered shut. Her hand cupped his jaw, tilting his head, deepening the kiss, and he melted into her—into the familiar taste of her, the softness of her mouth, the way she always kissed him like he was the only thing in the world. He breathed her in. It's over. She's pulling me out.
She pulled back. Her eyes were half-lidded, her lips slick and red. She took his hand—the one that had just unbuckled Joe's belt—and brought it to her mouth. Pressed a kiss to his knuckles. Gentle. Almost reverent.
Then she guided his hand downward.
Greg's fingers brushed against fabric. Denim. Then cotton. Then—hot skin, pulsing, wet at the tip.
His eyes snapped open. His hand was wrapped around Joe's cock.
Emmy's fingers curled over his, squeezing, adjusting his grip around the shaft. The heat of Joe's flesh burned through his palm. Precum slicked his fingers, warm and sticky. Joe groaned above him, a low, rumbling sound.
Emmy held Greg's hand steady, then leaned in close, her lips brushing his ear. Her breath was hot, her voice a whisper that cut straight through him.
"Now kiss the tip, Vanessa."
Greg's lips brushed against the tip. Hot. Soft. Wet with precum. He felt the pulse of Joe's cock against his mouth, a living thing, hungry for him. Joe groaned low and pushed his hips forward, his hand tightening in Greg's wig, forcing his head down. The tip pressed against Greg's lips, parting them, sliding inside before Greg could pull back.
His mouth was full. Full of heat and salt and the taste of precum, bitter and thick on his tongue. Joe's cock throbbed against his palate, spreading, claiming the space. Greg's hands flew up to push at Joe's hips, but Emmy caught his wrists, gentle but firm, holding them at his sides.
"Go ahead, Vanessa," Emmy murmured into his ear, her voice honey and steel. "Open your lips. Let your tongue taste Joe. Take him in your mouth."
Greg's jaw trembled. The corset crushed his ribs, forcing his breaths shallow and quick through his nose. Joe's cock filled his mouth, not deep yet, just the head, but it was enough. Greg's tongue touched the underside, felt the vein, tasted the salt. He wanted to gag. He wanted to pull back. He did neither.
He opened wider.
Inch by inch, Greg took Joe deeper. The shaft slid across his tongue, past his lips, filling the hollow of his cheek. Joe's hand guided him, steady and patient, not forcing, just presenting. Greg's eyes watered. His throat worked around the intrusion, trying to find a rhythm, trying to breathe. The satin of his gown whispered against his thighs. The corset pressed. His cock ached between his legs, wet and desperate, trapped against the pink satin sheets that screamed sissy at him with every fold.
"Stroke him, Vanessa," Emmy said. Her hand brushed his hair back, gentle, almost motherly. "Use your hand."
Greg's fingers found the base of Joe's cock. Thick. Hot. He wrapped his hand around it, feeling the pulse, the stretch of skin, the slick of precum making his grip slide easy. He moved his hand up as his mouth moved down. A rhythm. A blowjob. He was giving a blowjob.
Deeper. The tip touched the back of his throat. Greg gagged, a reflexive, ugly sound that made Joe groan louder. Joe's hips twitched, pushing deeper, and Greg's throat convulsed around the head, and then—somehow—it slid past. Joe's cock filled his throat. Balls deep. Greg's nose pressed against wiry hair, his lips stretched around the shaft, his eyes streaming tears.
He was swallowing Joe's cock. All of it.
"Good girl, Vanessa," Emmy whispered. "You're such a good cocksucker."
The words hit like a bullet. Greg's cock pulsed, leaking another hot rush of precum into the satin. Good girl. Cocksucker. Vanessa. The names ran through his skull, each one a spike of shame that only made him harder. He moaned around Joe's cock, a pitiful, muffled sound, and the vibration made Joe's hips jerk.
Joe grabbed Greg's head with both hands, fingers twisting into the wig, and started to thrust.
In. Out. In. Each stroke pushed Joe's cock past Greg's lips, along his tongue, into his throat. Greg gagged, choked, spit running down his chin, but Joe didn't stop. He fucked Greg's face like a toy, holding him still, using his throat. Greg's hands pushed at Joe's hips—stop, can't breathe, please—but Emmy brushed them away, her fingers cool against his skin.
"This is what you call a throat fucking, sissy." Emmy's voice was thick with arousal, her breath hot against his ear. "You wanted to know what it's like to be a woman. This is part of it."
Greg gagged again. Joe's cock filled his throat, held there, cutting off his air. Black spots swam at the edges of his vision. His hands clawed at the pink satin sheets, fisting the fabric, his lungs burning. Then Joe pulled back, and Greg gasped, coughed, sucked in air, and the cock slid back in before he could close his mouth.
Emmy's hand slid down Greg's body, past the corset, past the damp satin of his gown, until her fingers found his cock. She grabbed it, squeezed, and laughed—a low, delighted sound. "Still hard, Vanessa. Look at you. You love this. Your sissy cock is aching for more."
She stroked him through the wet satin, slow and cruel, matching Joe's rhythm. Thrust. Stroke. Thrust. Stroke. Greg's body didn't know whether to push into her hand or push Joe's cock away. It chose neither. It just shook, trapped between the two of them, his mouth full and his cock full and his mind a white static of shame and pleasure.
Joe thrust deep. Held. His cock twitched against Greg's throat, a warning, a promise. Greg's eyes went wide. No. Not in my mouth. Not—
Joe let out a loud groan, shoved his hips forward and pushed down Greg’s head as hot ropes of cum squirted violently into Greg's throat. Greg choked and gagged, held down as Joe groaned through his climax, filling Vanessa so deep she couldn’t spit it out. The taste hit him; Salt and the bitter tang of semen.
Emmy's hand was still wrapped around Greg's cock. She squeezed. "Look at you, Vanessa. You’re still so excited!"
Greg sat there, trembling, humiliated, his throat raw, his cock aching and denied, the pink satin sheets crumpled beneath him. The corset pressed against his lungs. The wig was askew. Cum dripped down his chin as Joe pulled back.
And he was still hard.
Joe's hands found Greg's shoulders and shoved. Greg's back hit the pink satin, the impact punched out of him by the corset, the bedsprings squealing beneath his weight. He tried to scramble backward, heels slipping on the slick fabric, but Joe's knees bracketed his hips, pinning him. The satin gown bunched around Greg's thighs, cool and treacherous, offering no purchase.
"No—please—" Greg's voice cracked, high and desperate, a stranger's voice. His hands flew up, palms out, pushing at Joe's chest. Joe caught his wrists, one in each hand, and lifted them over Greg's head, pressing them into the mattress. The motion was casual. Effortless. Like Greg weighed nothing.
"Please don't hurt me." The words tumbled out, broken, barely a whisper. Greg's eyes found Joe's face, searching for mercy, finding only hunger. Joe's jaw was set, his breath slow and deliberate, his pupils blown wide in the dim lamplight. He looked down at Greg like a man looking at a meal.
The mattress shifted. Emmy crawled onto the bed beside them, her knees denting the satin, a small bottle in her hand. The lamplight caught the label—lube, clear and clinical—and gleamed off her dark eyes. She was smiling. Not cruelly. Softly. Like she was watching something beautiful.
"This is it, Vanessa." Emmy's voice was honey, low and warm, wrapping around the name like a caress. "Joe is going to take your virginity. Right here. Right now. In front of me."
Greg turned his head toward her, his eyes wet, his lips trembling. Pleading. He tried to shake his head, but Joe's grip held him still. Emmy's smile widened, a flush spreading across her cheeks. She let out a soft moan, her hand sliding between her own thighs, pressing against the denim of her jeans.
Emmy leaned in and kissed him. Deep. Slow. Her tongue slid into his mouth, claiming it, tasting the salt of his tears and the lingering bitterness of Joe's cum. Greg kissed her back, desperate for something familiar, something that felt like her. Then she pulled away, leaving his lips cold.
She uncapped the lube. The sound was sharp in the quiet room. She poured a generous amount into her palm, slick and cool, and reached down. Greg felt her fingers slide between his thighs, pushing the satin aside, finding the tight ring of muscle that had never been touched. The lube was cold. Her fingers were warm. He gasped, his hips jerking, but Joe's weight held him down.
Emmy's other hand found Greg's cock, stroking it through the wet satin, slow and steady. "Shhh," she whispered, her lips brushing his ear. "Your body wants this. You are my beautiful sissy whore, Vanessa."
Her fingers pushed inside him. Just one, just the tip, but Greg felt every millimeter. He cried out, a sharp, keening sound, his back arching off the bed. Emmy worked the lube deeper, spreading it, stretching him, her touch clinical and intimate at once. Greg's cock throbbed in her hand, leaking another hot rush of precum into the already-soaked satin.
"There," Emmy said, pulling her fingers out. She wiped them on Joe's cock. He was hard, thick, the head swollen and dark. She gripped him, stroked him once, twice, then slicked the lube over his shaft with a practiced hand. Joe groaned, his hips pushing into her grip.
Emmy lifted the hem of Greg's gown, baring his ass to the lamplight. The corset had forced his hips forward, presenting him, making the angle perfect. She guided Joe forward, her hand on his hip, until the tip of his cock pressed against Greg's waiting entrance.
Greg felt it. Heat. Pressure. The tip nudging against the tight ring of muscle, not entering, just there. Promising. Threatening. His whole body went rigid, every muscle locked, his breath caught in his throat. He shook his head, a frantic, useless motion. "No. No. No."
Joe grabbed Greg's wrists again, lifting them above his head, pinning them with one hand. His other hand found Greg's hip, fingers digging into the padding of the breast forms, holding him in place. He looked down, his face half in shadow, and Greg saw the predator in his eyes.
"Shhhh," Emmy said again. She had started touching herself in earnest, her fingers moving inside her jeans, her breath coming in soft, wet gasps. "Relax, Vanessa. Let him in."
The tip pressed harder. Greg felt the ring of muscle begin to give, just a fraction, the pressure building into a burn. He opened his mouth to scream, but the only sound that came out was a whimper—a small, broken sound that belonged to someone he didn't recognize.
And then the tip pushed through.
The tip pushed through, and the sound that came out of Greg's throat was something he'd never heard himself make before. A loud, gasping moan that started in his chest and tore free, raw and broken, carrying fear and humiliation and something else—something that made his cock throb against the wet satin. His body convulsed, every muscle locking, and he heard himself whisper, "Please—please go slow—" His hips tried to crawl up the bed, a useless retreat, but Joe's weight held him in place.
"Slow," Joe repeated, and the word was a growl, a promise of nothing. He pushed deeper. An inch. Another. The stretch burned, a foreign pressure that radiated through Greg's pelvis, up his spine, into his skull. His hands clawed at the pink satin, fisting the fabric, his breath coming in short, sharp gasps against the corset's grip.
Emmy's mouth found his ear. "That's it, Vanessa," she breathed, her voice honey and venom. "Let him fill that sissy cunt. You're taking it so well. Such a good girl." Her hand slid down his chest, over the breast forms, and found his cock again, slick and hard through the satin. She squeezed. "Your little clit is still so hard. You love this, don't you?"
Joe pushed deeper. Another inch. Greg felt himself opening, the ring of muscle giving way, the pressure building into a fullness he'd never known. He moaned, a low, trembling sound, and there was pleasure in it. A thread of heat that wound through the pain, making his hips twitch. He hated it. He wanted more.
"Look at you," Emmy whispered. "Taking cock like a proper whore. You needed a real man to split you open. To teach you what it means to be a woman."
Joe's hips met Greg's ass. He was all the way in. The sensation was overwhelming—a deep, burning fullness that pressed against something Greg had never felt before. His vision swam. His breath caught. And then a moan slipped out, unbidden, pleasure roughening the edges of his voice.
Emmy laughed, a soft, delighted sound. "Oh, Vanessa. You're moaning. You're actually moaning. Listen to yourself." She stroked his cock through the satin, matching the rhythm of Joe's stillness. "You're a sissy whore. Say it. Say 'I'm a sissy whore.'"
Greg shook his head, tears spilling down his cheeks, but his lips parted. "I'm—" The words choked in his throat. Joe began to move. A slow pull, a slow push, and Greg's voice broke into a cry.
"Say it, Vanessa."
"I'm a sissy whore." The words came out a sob, and his cock throbbed in Emmy's hand, another hot rush of precum soaking the satin.
Joe's pace quickened. The slap of his hips against Greg's ass filled the room, wet and rhythmic. The satin gown rustled and surged with each thrust, pooling around Greg's waist, the corset creaking as his body was rocked forward. The pressure built, spread, and Greg found himself moaning with each stroke, his body no longer fighting.
Emmy's voice grew ragged. "You're going to come like a bitch, Vanessa. You're going to come with a man's cock in your cunt, and you're going to scream when you do." Her fingers moved faster on his cock, dragging the wet satin over the head, and Greg's hips bucked into her hand, chasing it.
Joe grunted, a raw animal sound, and drove deeper. Harder. The bedsprings squealed. The lamp on the nightstand shook, casting jumping shadows across the walls. Greg's hands released the satin and found Emmy's arm, gripping her wrist, not to stop her but to hold on.
"Oh my God," Greg gasped, the words tumbling out before he could stop them. "I think I'm going to cum—" The sentence broke apart as Joe's hips hammered into him, driving the air from his lungs, his body jiggling like a rag doll under the force.
"YES!" Emmy screamed, her body shuddering against him, her hand clamping tight around his cock. "Come like a bitch, Vanessa! COME LIKE A BITCH!"
Joe let out a final, guttural roar, his body tensing, his cock pulsing deep inside Greg. The first hot jet of cum hit Greg's prostate, and that was it. His body seized. His back arched. A scream tore from his throat, high and broken, as his cock erupted into Emmy's hand, hot cum soaking through the satin, running down his thigh. The orgasm ripped through him, wave after wave, his vision white, his mind blank, his body nothing but pleasure and shame.