Chapter 6: The Crossdress
The walk back to Tiffany’s dorm was a blur of fluorescent hallway lights and the echo of their footsteps. Ed’s body felt both heavy and hollow, a vessel still thrumming from the library. He followed her into the room, and the sensory assault was immediate. The neon signs cast a sickly pink and blue glow over the chaos. That stuffed unicorn lay face-down on the floor.
“Close the door, baby,” Tiff said, already digging through a heap of clothes in the corner. “Time for the main event.”
Ed complied, the click of the lock sounding final. He stood awkwardly by the door, watching as she tossed aside lingerie and fast-fashion tops with abandon.
“Here!” she exclaimed, pulling out a tangle of fabric. She shook it out. It was a dress, if it could be called that. A scrap of cheap, shiny black polyester, barely long enough to cover his thighs, with thin spaghetti straps and a neckline that plunged to nowhere. She tossed it to him. It landed against his chest, smelling of clubbing and sweat.
“Put it on,” she commanded, grinning. “And these.” She flung a pair of fishnet stockings at him, followed by a pair of ridiculously high, glittery platform heels. “Hurry up. I wanna see.”
His hands trembled as he undressed. His own clothes—jeans, a worn-out band t-shirt—felt like a shed skin as they pooled at his feet. The polyester was cold and unforgiving against his skin. He struggled into it, the material straining over his shoulders and clinging obscenely to his chest and hips. The stockings were a battle of snags and awkward balancing. The shoes forced him into an unnatural, teetering arch.
Tiff clapped her hands, a gleeful, percussive sound. “Oh my god. YES. Look at you.” She grabbed his arm, spun him toward the full-length mirror stuck to the back of her door.
Ed—no, the reflection—was a stranger. The dress emphasized the softness of his frame, the surprising swell of his hips and the pronounced curve of his ass that the thin fabric did nothing to hide. His legs, sheathed in black netting, looked long and oddly delicate. His face, pale and shocked above the trashy glamour, completed the jaring picture.
“Who’s that?” Tiff whispered in his ear, her arms wrapping around his waist from behind, her chin on his shoulder. Their eyes met in the glass. “That’s not Ed. Ed’s boring. Ed studies code.” She ground her hips against his ass. “This is someone fun. This is Evie. Say hi, Evie.”
He opened his mouth. A dry click. He tried again. “Hi,” he breathed, the voice unfamiliar even to himself.
“Hi, Evie,” Tiff cooed, kissing his neck. “Evie’s a good slut, aren’t you? Evie doesn’t worry about midterms. Evie just wants to feel good.” Her hand slid down from his stomach, over the shiny fabric, and cupped him between his legs. He was soft, overwhelmed. “Evie’s clitty is so cute and little. Perfect.”
She released him and bounded over to her closet, pulling out a large, pink plastic case. She snapped it open on the bed, displacing the unicorn. Inside, nestled in garish pink velvet, lay a monstrosity of silicone. A foot-long, thick, flesh-colored double-ended dildo.
“Roomie’s gone for the weekend,” Tiff said, hefting the toy. It was grotesque, veined, and intimidating. “So Evie and I are gonna get… acquainted.”
She produced a bottle of clear lubricant, slicking the entire length of the toy until it shone under the neon lights. The sound was slick, viscous.
“Open wide, Evie,” Tiff said, her tone switching from sweet to directive. She brought the tip to his lips. “Show me how you throat it. Like I showed you in the library. But this is bigger. Take it. Want it.”
Tears of shame pricked his eyes, but his mouth opened. The silicone, cold and tasting chemically of fake cherry, pushed past his lips. He gagged immediately, his body convulsing.
“Relax your throat,” she instructed, pushing steadily. “Imagine it’s my tit. You love my tits, don’t you?” It was a brutal, shallow fuck of his mouth. She pushed until his nose was buried in the slick silicone, until his eyes watered and his throat fluttered wildly around the intrusion. She held it there, watching him struggle, before pulling it back with a filthy, wet pop.
She didn’t wipe it off. Instead, she brought the glistening, saliva-slicked end to her own mouth and deep-throated it in one smooth, practiced motion, her eyes rolling back in theatrical ecstasy. She fucked her own face with it, gagging loudly, messily, a performance of pure decadence.
Then she pulled it free, a strand of her saliva connecting her lips to the toy. “Your turn again,” she gasped. “We’re sharing.”
Back and forth it went. A violent, rhythmic exchange. The dildo became a conduit for their spit, a shared violation. In, out, gagging, popping. The air filled with the sounds of it: wet choking, grunts, Tiff’s encouraging moans. “Good girl, Evie. Take it all. Make it messy.”
Ed’s mind began to detach. The gagging reflex became a numb, automatic pulse. The taste of synthetic cherry and shared saliva was just a fact. The person in the mirror—Evie—was the one doing this. Evie was the one who craved the fullness, the humiliation, the approval in Tiff’s eyes.
“Now,” Tiff panted, her own lips swollen and slick. “The good part.” She pushed him face-down onto the satin sheets. The dress rode up. The stockings whispered against each other.
He felt the cold, lubed head of the toy press against him, not at his mouth, but at the other entrance, the one still tender from the library. He gasped into the sheets.
“Shhh, it’s okay,” Tiff soothed, one hand spreading him open, the other guiding the toy. “Evie’s ass is so hungry. It’s been empty all day.” She pushed, and the thick, unyielding silicone began to stretch him wider than anything ever had. It was a burning, relentless invasion. A low, continuous moan was torn from his throat.
Just as the pressure became a sharp, bright pain, he felt the bed dip. Tiff straddled him, facing away. He felt the other end of the toy, slick with their combined spit, press against her. She sank down onto it with a long, satisfied sigh, taking half its length inside herself in one smooth drop.
They were linked. A circuit completed.
Tiff began to move, rocking back and forth. Her motion drove the toy deeper into him, then pulled it almost all the way out, before sheathing it inside her again. It was a brutal, synchronized fucking. Each of her forward rocks slammed the base of the toy against his cheeks; each backward grind impaled him anew.
“Fuck, yes,” Tiff moaned, reaching back to grab his hip, her nails digging in. “Feel us, Evie. We’re one slut now.”
The pain in Ed’s ass blurred, mutated, melted into a deep, radiant fullness that sparked something electrical in his gut. His softness was gone; he was hard again, trapped and leaking against the satin sheets. His moans lost their edge of distress, becoming higher, needier. The dress, the shoes, the netting—they weren’t a costume anymore. They were her skin. Evie’s skin.
“Who are you?” Tiff grunted, slamming back onto him.
The answer came without thought, in a broken, gasped voice he didn’t recognize as his own. “Evie! I’m Evie!”
“What does Evie want?”
“This! I want this! I want it!” The words were a sob of release.
Tiff’s rhythm became frenzied, animalistic. The toy pistoned between them, a relentless engine of their union. The slapping of flesh, the squelch of silicone and lube and sweat, their ragged cries—it was a symphony of filth. Ed’s—Evie’s—vision whited out at the edges. The orgasm that ripped through her wasn’t centered in her trapped, ignored clitty; it erupted from the depths of her brutally filled ass, a seismic wave of submission that left her shuddering and blind.
Tiff followed with a sharp cry, collapsing forward before rolling off, breaking the connection. The toy slipped out of Evie with a soft, wet sound.
They lay in the wreckage of the bed, breathing in ragged unison. The neon lights buzzed.
After a long time, Tiff propped herself up on an elbow. She looked down at the figure beside her: smeared makeup, dress twisted, body glistening with sweat and lube. She traced a finger over Evie’s flushed cheek.
“See?” Tiff whispered, her voice husky with spent passion and profound satisfaction. “I told you you’d like it. Evie’s so much prettier than Ed could ever be.” She kissed Evie’s forehead, a patronizing, possessive seal. “My good girl.”