He’d hoped not too many people would tune into the stream that night—maybe they’d just laugh and move on. Instead... it blew up.
By the time he ended the show, Kyle had more new subs than he’d earned in the entire last year. Notifications flooded his dashboard, the numbers climbing faster than he could process—his chat a wall of emotes, cheers, and thirsty, drooling comments.
“Wait… this is a GUY??”
“Holy shit he’s cuter than my girlfriend.”
“I’d ruin that little bunny so bad 😩💦”
“pls tell me there’ll be more streams like this 🥺🙏”
He couldn’t look at the comments without his face burning. He told himself he’d never do it again.
And yet… every stream afterward, no matter the game or topic, they begged. Demanded.
“When’s the next crossdressing stream?”
“Not you streaming as a dude again 🙄”
“No skirt today? unsubbing fr 😤”
And Jess—his sweet, devious girlfriend—was no help at all.
“All your viewers want another crossdressing stream,” she said, casually scrolling through the chat. “Isn’t this what you wanted? All those new subs pouring in?”
She looked over at him, smiling. “Just give them what they want, babe.”
Eventually, he gave in—letting her dress him up for one more stream. Then another. Before long, it was once a week… then twice… then three times.
Now? Kyle hadn’t streamed as a guy in over a month.
And Jess had leaned in. Hard. The chastity cage she bought him was always locked on now—small, pink, and secured with a tiny heart-shaped padlock.
She ordered breast forms next—large, realistic ones made of soft silicone. The skin tone was perfect, the nipples disturbingly lifelike, and once they were glued in place, they moved just like the real thing—bouncing and jiggling with every little motion.
His closet slowly shifted. First a few crop tops and thigh-highs… now? He had more girl clothes than guy clothes. Skirts, lingerie, pastel hoodies, low-cut sweaters, panties in every color—Jess insisted on picking out his outfit before every stream. Sometimes sexy and barely-there, sometimes soft and girly.
Tonight? She was clearly in that cute mood.
“Sit still, princess,” Jess said sweetly, her hand guiding his chin as she leaned in with the eyeliner.
Kyle didn’t dare move. The blush was already done—soft and rosy, blended high on his cheeks to exaggerate the innocent, flustered look she loved to see him wear. His lashes were long and carefully curled, framing his eyes in a way that made him look helplessly wide-eyed. His eyeshadow shimmered with pale pink glitter under the warm bedroom lights. A glossy peach tint slicked across his lips, giving them a soft, kissable shine.
Jess stepped back, pleased. “Perfect,” she said, her tone just a little too proud. “Now let’s get you dressed.”
Tonight’s outfit was sickeningly sweet: a tight pink top with a low scoop neckline, ribbon laced through the front, and sleeves that hugged his arms. A sheer pink skirt floated delicately around his hips, swaying gently with every movement. Of course, the soft bulge of his locked cage pressed gently against the delicate fabric of his panties.
Jess clipped on his choker last—a simple black band with a tiny silver bell that jingled softly whenever he moved.
Kyle caught his reflection in the mirror and blushed hard. The makeup, the outfit, the soft bounce of his glued-on chest—there wasn’t a sliver of masculinity left. He padded across the carpet on bare feet, his skirt rustling softly with every step. Sitting down at his desk, cheeks still burning, he slipped on his pink headset.
His finger hovered over the key to start the stream…
Click.
“Hiiiii everyone~” he said, voice soft and sugary as his stomach twisted. “Welcome back to the stream… we’re picking up right where we left off, so get comfy~”
cool
2025-07-04 12:34:06 +0000 UTC