“You look so damn hot tonight,” Jake murmured, his eyes raking over the slinky black dress, the soft waves of blonde hair, the way Riley’s delicate fingers clutched the wine glass. “I still can’t believe you used to be a guy.”
Across the table, Riley stiffened, his jaw tightening. “I still am,” he shot back, though the words felt flimsy even as he said them.
The statement might have held weight once, back when his reflection still showed something recognizable—something masculine. But now? The girl staring back at Jake from across the candlelit table was flawless. The sleek black dress hugged his slender frame, its thin straps baring his delicate shoulders and collarbones. Soft blonde waves framed his face, styled with effortless precision, the perfect balance of refinement and allure. His wide, expressive eyes—framed by long, fluttering lashes—held a subtle shimmer, his makeup applied with a practiced hand. The warm glow of the candlelight caught the soft sheen of his glossed lips, their natural pink hue enhanced to appear fuller, more inviting.
And then there was his voice. He winced at how airy it sounded, a breathy, practiced lilt that had been drilled into him until it came as naturally as breathing. No matter how much he tried to force the words out lower, stronger, they still left his mouth in a tone that was unmistakably girlish.
Beneath the table, his legs pressed together instinctively, the position poised and demure, the way any proper lady would sit. His manicured fingers—tipped in a soft, neutral polish—curled around the stem of his wine glass, the delicate way he held it betraying every bit of training that had molded him into the vision of femininity he was now.
“And I’m only doing this because you’re making me,” he added quickly, as if clinging to some last shred of defiance.
Jake just smirked, pulling out his phone and unlocking it with an amused little grin. Riley’s eyes narrowed the moment he saw that expression—that smug, knowing look Jake always had when he was about to mess with him. His irritation flared as Jake scrolled through his phone, completely unbothered.
“What?” Riley snapped, his voice sharp with impatience.
Jake scrolled for a second, then tapped a video. He turned up the volume just enough for Riley to hear before sliding the phone across the table.
“Oh God—Jake—you’re so big! You feel amazing!” Riley’s voice was breathless, high-pitched, and dripping with desperation as he bounced on Jake’s thick cock. The video showed him straddling Jake, his slender hips moving with a rhythm that was both practiced and eager. His makeup was smudged, glitter and mascara streaked down his cheeks, his lips parted and tongue out in complete surrender. His wide, pleading eyes locked onto Jake’s, utterly lost in the moment.
“Please—” Riley moaned, his voice wrecked and trembling with need. “You’re so deep, Jake! I need it—I can’t get enough of you!” His hands gripped Jake’s shoulders for support, his body moving with unrelenting enthusiasm. “You’re the best, Jake! You feel so good—oh my God, I’m gonna—”
Jake’s low, commanding voice cut through Riley’s gasping moans. “I’m about to cum, Riley. You’re gonna swallow every drop, aren’t you?”
“Yes, yes!” Riley cried out, his voice trembling with desperation. “Please, I want it all! I need it, Jake! Give it to me!”
The video shifted to Riley lifting himself off Jake’s cock, his thick length glistening with a mix of precum and Riley’s slickness. The camera lingered on the juicy imagery of Jake’s long dick slowly being extracted from Riley’s tight ass, the sight both lewd and mesmerizing. Riley didn’t hesitate, sliding gracefully to his knees and opening his mouth, ready and eager. Jake groaned as he released his load, thick and heavy, directly into Riley’s waiting mouth. Riley’s eyes fluttered shut, a look of pure bliss on his face as he swallowed every drop, his tongue darting out to catch any stray remnants.
The video ended with Riley licking his lips, a satisfied smile spreading across his face. “Mmm, so yummy,” he purred, his voice soft and dreamy.
Riley’s stomach dropped as he watched himself—so lost in pleasure, moaning, begging, giving in completely. His cheeks burned hotter with every second, his fingers tightening around his wine glass as he tried to act unaffected.
“I-It’s not—” he stammered, swallowing hard. “I wasn’t—I mean, I didn’t actually—”
Jake leaned back, swirling his drink lazily, his smirk deepening. “Oh? You didn’t enjoy it?” His voice was smooth, teasing, full of knowing amusement. “Well, I wouldn’t want to make you do something you don’t like… I guess we can just skip it tonight, then.”
Riley’s breath caught. “W-Wait—” he blurted out before he could stop himself, face burning. “I-I mean—just… w-we might as well…” His grip tightened around his glass, thighs pressing together as he swallowed hard. “B-but not because I want to…”