Still holding Greg's erection through the emerald satin, Natalie's other hand found his ass—palm flat, fingers digging into the curve through the dress. She squeezed, hard, and he felt the seam of the panties bite into him. "Let's see how good of a sissy Gina really is," she said, her breath warm against his ear. Her grip tightened, possessive, and his cock jerked against her palm, damp fabric clinging to the head.
Amy appeared beside them, a bottle of lube in her hand—a clear, thick liquid that caught the yellow cone of the lamp. She unscrewed the cap with a soft pop. "Lift the dress," she said, and Natalie did, bunching the satin up around Greg's waist. Cool air hit his exposed ass, the waistband of the pink panties pulled taut. Amy squeezed a generous dollop onto her fingers, then reached under the elastic, working the slick gel into his hole. Her touch was gentle, practiced—she'd done this before, on many nights. He felt his body yield, the muscle relaxing under her fingers, and he let out a shaky breath.
Natalie shifted behind him, and he felt the silicone press against his thigh—the strap-on, slick with lube. Amy withdrew her fingers and wiped them on the hem of the dress. "Lean forward," Natalie murmured, her voice low. "Hands on the vanity."
Greg obeyed, his palms flat on the dark wood of Caroline's vanity table. The edge bit into his thighs as he bent, the dress riding higher, pooling around his waist. The mirror in front of him caught his reflection—the blonde wig tangled, the lipstick smeared, his eyes wide and glassy. He looked like a stranger. He looked like Gina.
The cool silicone pressed against his slicked hole. He felt the resistance, the slight give of muscle, and then Natalie pushed—slow, deliberate, her hip pressing against his ass. The stretch was a shock, a fullness that made his breath catch. He gripped the edge of the vanity, knuckles white, as she sank into him inch by inch. A sound escaped his throat—a high, thin whimper that didn't sound like his own voice. It belonged to Gina.
"There we go," Natalie breathed, her voice thick with satisfaction. She bottomed out, her pelvis flush against his ass. He could feel her heartbeat through the silicone, or maybe it was his own, thundering in his ears. He was full, so full, and his cock throbbed against the satin, dripping onto the inside of the dress.
From the bed, Caroline's voice cut through the haze. "Look at her take it."
He glanced sideways, catching her silhouette in the half-light. She was propped against the headboard, one hand between her legs, her green eyes glittering. Her fingers moved under the fabric of her skirt, slow and unhurried. "Like she was made for it," she murmured.
His shame was a hot coal in his chest, but beneath it, something else stirred—a warmth that spread through his belly, loosening the knot of humiliation. He met his own eyes in the mirror again, and behind him, he saw Amy. She'd moved to stand at the foot of the vanity, arms crossed, watching. When their gazes met in the glass, she smiled—soft, proud, her brown eyes warm. She nodded, almost imperceptibly.
The shame cracked open. The gratitude that flooded in was dizzying. She wasn't disgusted. She was proud. She wanted this. She wanted him like this.
He rocked back onto Natalie's cock—a tentative roll of his hips. The silicone slid deeper, and he felt a sharp jolt of pleasure that made his thighs tremble. "Good girl," Natalie said, her hand firm on his hip. "Again."
He obeyed, pushing back against her, finding a rhythm. The vanity creaked under his weight. The wig swayed with each thrust, its synthetic strands brushing his shoulders. In the mirror, he saw himself—a tall, broad-shouldered figure in a too-small dress, bent over, impaled on a black strap-on—and the heat of it, the wrongness and the rightness, made his cock ache.
Caroline's hand moved faster, her breathing audible now—soft, rhythmic gasps. "Fuck her, Natalie," she said, voice rough. "Make her remember."
Natalie's grip tightened on his hips. She pulled out slowly, until only the tip remained, then slammed back in. The sound—wet, obscene—filled the room. Greg's knees buckled, but the vanity held him upright. He let out a moan, low and trembling, and heard Amanda's laugh from somewhere behind him—a breathless, surprised sound that made his face burn.
He didn't look at her. He couldn't. He kept his eyes on the mirror, on Amy, on the girl he loved watching him become someone else. Her smile hadn't wavered. She mouthed something—he couldn't read it, but it looked like I love you—and his heart lurched.
Natalie fucked him harder, the rhythm fast and punishing. The wood of the vanity bit into his palms, and the satin rustled with every thrust. His own cock was a desperate, leaking thing, trapped against his belly, untouched and aching. He wanted to touch it. He wanted someone to touch it. But no one did. They let him hang there, full and empty at once, on the edge of something he couldn't name.
"Please," he heard himself say—a broken, breathy plea. "Please, please—"
Natalie's fingers dug into his hip, and she leaned over him, her body warm against his back. "Please what, Gina?" she whispered. "Tell us what you need."
He couldn't form the words. His mouth opened, but only a sob came out—a sound of surrender that shook through him. His hands slipped on the vanity, and he sagged against her, letting her hold him up.
The room dissolved into heat and laughter and the rustle of satin. Caroline's gasps rose in pitch; a moment later, she let out a long, shuddering sigh. Amanda giggled, a nervous, excited sound. And Amy—Amy crossed to him, reached past Natalie, and brushed her fingers across his cheek. "You're doing so well," she said, her voice soft. "Just a little longer, baby. Just a little more."
He nodded, tears blurring his vision, and rocked back onto Natalie's cock again, letting the rhythm take him, the shame and the gratitude and the love pinning him in place like the satin dress that clung to his skin.
"Alright, princess." Natalie pulled out slowly, the silicone dragging against his walls, and Greg gasped at the loss of fullness. "Let's take this somewhere more comfortable."
She gripped his hip and guided him off the vanity, his legs trembling, the emerald dress bunched around his waist. His cock jutted out from the damp satin, slick and swollen, the head glistening under the lamplight. Amy took his hand and led him toward the bed, her fingers warm and steady.
"On your knees," Natalie said, her voice flat and commanding. "Face the headboard."
Greg climbed onto the silk sheets, the fabric cool against his shins. He dropped to his knees, his thighs spread, the dress pooling around his hips. The wig slid forward, brushing his cheeks, and he pushed it back with a trembling hand. Behind him, the bed dipped as Natalie climbed on, the leather harness creaking.
"Look at her," Caroline said from somewhere to his left, her voice thick with derision. "On her knees like a good little cocksucker. Bet she's done this before, haven't you, Gina?"
"I—" Greg's voice cracked. He swallowed. "Yes."
"What was that?" Caroline's tone sharpened. "I couldn't hear you, sissy."
"Yes," he said louder, his face burning. "I've done this before."
"Of course you have." Amanda's voice was softer, but no less cutting—a sweet, mocking lilt that made his stomach clench. "You were made for this, weren't you, Gina? Just a big, dumb cockslut in a prom dress."
Heat flooded through him, and his cock twitched, a bead of pre-cum sliding down the shaft. He heard Amy's quiet laugh, fond and knowing.
"Look at that," Natalie murmured, her hand finding his hip. "You like being called a slut, don't you, Gina? Your little cock is dripping for it."
He couldn't answer. His throat was tight, his breath coming in short, ragged gasps. The silicone pressed against his slicked hole again, and he braced himself, his fingers gripping the rumpled sheets.
"Yeah, fuck her doggy style," Caroline said, her voice rising with glee. "Fuck her like the bitch she is."
Laughter rippled through the room—light, cruel, intoxicating. Greg's cock jerked, and he let out a moan, high and involuntary, as Natalie pushed into him in one smooth thrust. The stretch was sharp, perfect, and his elbows buckled, his forehead dropping to the sheets.
"That's it," Natalie breathed, her hips pressing against his ass. "Take it, Gina. Take every inch like a good little sissy."
She pulled back and slammed forward, and the bed creaked beneath them. Greg's moan dissolved into a gasp, his mouth open against the silk. The rhythm built fast—hard, punishing thrusts that drove him forward with each impact, the wig sliding over his eyes.
"She's moaning like a whore," Amanda said, her voice somewhere between amazed and delighted. "Listen to her."
"Because she is a whore," Caroline shot back. "Amy's personal little cocksleeve. Our personal little cocksleeve now."
Amy's voice cut through, soft and amused. "She's yours for the night. Do whatever you want with her."
Greg's hips rocked back to meet Natalie's thrusts, the angle driving the silicone against something deep inside him—a spot that sent sparks across his vision. He cried out, a broken, shameless sound, and his cock throbbed, untouched, leaking onto the mattress.
"Oh, she found her spot," Natalie said, her voice a low purr. "Look at her, riding my cock like she was born for it. You were born for it, weren't you, Gina?"
"Yes," he gasped, the word torn from his throat. "Yes, yes, yes—"
"Pathetic," Caroline muttered, but her voice was thick with arousal. "So fucking pathetic. I love it."
The room spun around him—the laughter, the heat, the relentless rhythm of Natalie's hips. He was nothing but a body, a dress, a wig, a slut stretched open on a silicone cock. The thought should have broken him. Instead, it made him harder, made him push back harder, made him beg with every thrust for more.
The rhythm built toward something frantic—Natalie's hips slapping against his ass, her fingers digging hard into his hips, the laughter and the jibes blurring into a single cresting wave. His cock leaked against the sheets, untouched, aching, and the pressure in his belly coiled tighter, hotter, a thread about to snap.
"Oh my god—I think she's gonna come."
Natalie's voice cut through the haze, breathless and sharp. The thrusts stopped. The silicone slid out of him slow, dragging against his walls, and the absence was a yawning emptiness that made him gasp. He sagged forward, his forehead pressed to the silk, his whole body trembling.
"No—" The word escaped him before he could stop it, a whimper, a plea. His hips rocked back, searching for the fullness again. "Please, please—"
"Holy shit, she's desperate." Caroline's laugh was bright and cruel. "Look at her, grinding on nothing like a bitch in heat."
Amanda stepped forward, her hazel eyes wide, her breath coming shallow. A dark stain had spread on the front of her pink sundress where her thighs pressed together. "Can I try?" Her voice was soft, almost shy, but there was hunger beneath it. "I want to see what it feels like."
"Make him come from his ass." Caroline's voice rang out, sharp and delighted. "Make him come like a bitch."
Laughter rippled through the room—Amy's warm chuckle, Caroline's cackle, even a nervous giggle from Amanda. Greg's cock throbbed, a bead of pre-cum sliding down to the sheet.
Natalie stepped back, breathing hard, a sheen of sweat on her forehead. She unbuckled the harness with practiced fingers and held it out to Amanda. "All yours. Go slow at first—she loosens up fast, though."
Amanda took the harness, her hands trembling. She fumbled with the straps, her eyes darting to Greg's spread thighs, the pink, wet hole glistening under the lamplight. "How do I—"
"Here." Amy rose from the edge of the bed and crossed to her, her movements calm and assured. She guided Amanda through buckling it, adjusting the silicone cock until it jutted out at the right angle. "There. Just like that."
Greg watched through the curtain of blonde wig, his breath ragged, his arms shaking. The cool silk of the sheets pressed against his cheek. He was on his knees, exposed, empty, waiting.
Amanda stepped behind him, the leather creaking. Her hand found his hip—smaller than Natalie's, softer, trembling—and she pressed the head of the silicone against his slicked hole. He heard her take a breath, heard her whisper something under her breath, and then she pushed in.
Slow. So slow. The silicone stretched him inch by inch, and he let out a shuddering moan, his fingers twisting in the sheets. Her other hand came to rest on his lower back, steadying herself, and she pushed deeper until her hips met his ass.
"Oh," she breathed. "Oh my god."
"How does it feel?" Amy's voice was soft, curious.
"Warm. Tight. She's—she's clenching around me." Amanda's voice cracked. "She's so tight."
"That's because she's a sissy who was born for this," Caroline said from the bed, her hand moving between her own thighs again. "Now fuck her. Make her come."
Amanda pulled back and thrust forward, clumsy, unpracticed, but the angle caught him just right—sent a spike of heat through his groin. He cried out, his elbows buckling, and his cock jerked, untouched, desperate.
"Yeah, like that," Amanda muttered, finding a rhythm. Her hips rocked against him, faster now, the slap of skin filling the room. "You like that, Gina? You like being fucked by a girl who's never done this before?"
Greg could only moan in response, his mouth open against the silk, his vision swimming. The shame and the pleasure tangled into one bright, unbearable thing, and he felt himself hurtling toward the edge again.
Amanda's hips found a rhythm, faster now, less hesitation in each thrust. Her breathing quickened against his back, small gasps escaping her lips with every forward stroke. Her hand slid from his hip to his waist, fingers digging into the bunched emerald satin, pulling him harder onto the silicone.
"Oh god," she breathed, her voice cracking. "She feels so—so good."
"Look at Amanda," Caroline crowed from the bed. "Look at her go. Never fucked anything before tonight and now she's pounding a sissy like a pro."
Greg's arms trembled, his forehead pressed to the silk sheets. The wig had slipped forward, blonde strands clinging to his damp cheeks. Each thrust drove the silicone deep, grinding against that spot inside him that sent electricity through his spine. His mouth fell open, a moan spilling out—louder than he meant, shameless and raw.
"Harder," he gasped. "Please—harder—"
A ripple of laughter cut through the room.
"Listen to her," Natalie said, her voice cool and amused. "She's begging for it. Like a bitch in heat."
"Please," Greg repeated, his voice cracking. "Please, please—"
Amanda's thrusts grew harder, more desperate. Her breath came in ragged pants now, her small hands gripping his hips with surprising strength. The slap of her thighs against his ass filled the room, wet and rhythmic.
"You want it harder, Gina?" Amanda's voice was breathless, almost giddy. "You want me to fuck you like a whore?"
"Yes," he moaned. "Yes, yes—make me come—please make me come—"
The women erupted. Caroline's cackle cut through the room, bright and cruel. Natalie laughed low and sharp. Even Amy let out a soft chuckle, watching from the edge of the bed with a smile that was pure pride.
"Oh my god, she actually said it," Caroline gasped between laughs. "She's begging to come on a strap-on. In a prom dress."
"Pathetic," Natalie said, but her voice was thick with arousal. "You're pathetic, you know that, Gina? A fucking fag in a dress, begging a girl to make you come from your ass."
Greg's cock throbbed, a fresh bead of pre-cum sliding down to the sheets. The word hit him like a slap—and he moaned, pushing back onto Amanda's thrusts, his body betraying him completely.
"Oh, she liked that," Natalie said, her eyes narrowing. "Did you like being called a fag, Gina? Did that make your little cock twitch?"
"Yes," he gasped, the word torn from somewhere deep. "Yes, yes—"
"Disgusting," Caroline said, but her hand was moving faster between her own thighs, her green eyes fixed on the scene. "Absolutely fucking disgusting. I love it."
Amanda's rhythm grew frantic, her breath coming in sharp gasps. Her forehead pressed against his shoulder blade, her fingers curling into the satin. "I'm—I'm close," she whispered, her voice trembling. "I don't know why but I'm—"
"Because you're fucking a fag who was born for this," Natalie said, stepping closer. She circled them, her dark eyes glittering. "Next time I'll bring my boyfriend. He's always wanted to fuck a sissy. What do you think, Gina? You want a real cock instead of silicone?"
Greg could only moan in response, his body rocking back to meet Amanda's thrusts, his mind dissolving into heat and shame and desperate, aching pleasure.
Amanda's thrusts grew erratic, her grip on his hips tightening until her nails bit through the satin. Her breath came in sharp, uneven gasps against his shoulder blade, and he felt her whole body begin to tremble behind him.
"Oh fuck—" she whimpered, her rhythm falling apart. "Oh fuck, oh fuck, I'm going to—"
"Do it," Caroline snarled from the bed, her voice thick and breathless. "Come on that sissy's ass. Make her feel it."
Natalie stepped closer, her shadow falling across Greg's face. "Look at her," she murmured, her voice low and precise. "Amanda Rossi, sweetest girl in the room, losing her mind on a fag's hole. Never thought you had it in you."
Amanda let out a strangled cry, her hips slamming forward in a violent, uncoordinated thrust. Her whole body seized, her fingers curling into the satin as she drove the silicone as deep as it would go, a raw, guttural scream tearing from her throat. "Yes—yes yes yes—"
Her orgasm ripped through her in waves—her thighs shaking, her pelvis grinding against him, her voice cracking into incoherent sounds. She pushed deeper, harder, holding him pinned against the mattress, and the sensation of her losing control—the desperate, animal need in her movements—sent a spike of electricity through Greg's spine.
"Oh my god," Amy breathed from somewhere behind him, her voice soft with wonder. "He's going to come like a bitch."
The words landed like a physical blow. His cock jerked violently, untouched, and a strangled moan escaped his lips. "Please—please—"
"Look at her," Caroline crowed, sitting up on the bed, her hand still between her slick thighs. "Look at that pathetic little fag, about to shoot her load from getting ass-fucked. In a prom dress."
Natalie laughed, low and sharp. "Best thing I've ever seen. Amanda Rossi made a whole man come without touching his cock."
Greg's body betrayed him completely. His back arched, his fingers clawing at the silk sheets, and a long, shuddering wail spilled from his throat as his orgasm tore through him in waves. His cock pulsed, thick ropes of cum spurting onto the pale blue sheets beneath him—a hot, wet stain spreading across the fabric. His hips jerked, fucking the empty air as he emptied himself, his vision going white at the edges, his mind dissolving into heat and shame and gratitude.
The room erupted.
Caroline's cackle cut through the air, bright and unhinged. Natalie clapped slowly, a mocking applause that made Greg's face burn even hotter. Amanda slumped forward, still breathing hard, her forehead pressed to his shoulder blade as she let out a shaky, disbelieving laugh.
"Oh my god," Amanda gasped between breaths. "Oh my god, did I—did I just—"
"You made a fag come from your strap-on," Natalie said, her voice dry and amused. "Frame it. Put it on your resume."
Greg lay there, trembling, his cheek pressed to the damp silk, his cock still twitching weakly. The cum pooled beneath him, warm and sticky, and he could hear them laughing—could hear the delight in their voices—and instead of shame, he felt something crack open in his chest. Gratitude. Relief. Belonging.
He was exactly where he was supposed to be.
Amanda pulled out slowly, the silicone sliding free with a wet sound that made him gasp. She collapsed beside him on the bed, her face flushed, her hazel eyes wide and dazed. "That was—" she started, then shook her head, laughing. "I don't even know what that was."
"That was Gina taking her first real pounding," Caroline said, sliding off the bed and walking toward them. She stood over Greg, looking down at the mess he'd made on her sheets, and let out a low whistle. "Look at that. You really are a fucking sissy, aren't you? Cumming on a girl's bedsheets from a plastic dick."
Greg couldn't form words. He just nodded, his eyes closed, his body still humming with aftershocks.
From the edge of the bed, Amy's voice floated soft and warm. "You did so good, baby." He felt her hand on his hair, smoothing the tangled wig. "You made me so proud."
Natalie picked up the lube bottle and tossed it to Caroline. "Round two?" she asked, her smile sharp and hungry.