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Chapter 28
by
Mr Nice Guy
What's next?
All in a Day's Work
The ring light purred beside the bed, casting a pink warmth across Riley's skin. He adjusted the camera angle with care—thighs spread just right, chest arched forward, glossy lips parted. Everything had to be perfect. Everything had to work.
Because this wasn't just content. This was investment.
He looked down at his chest—his beautiful chest—and smiled. Full, round, heavy. Soft but powerful. His new girls were flawless, and they bounced with the kind of natural heft that turned heads. He gave them a slow squeeze, and a quiet moan escaped his lips.
He'd never been so proud of his body.
Cosmetic surgery had changed his life. Changed him. And if this felt this good—this right—then why would he stop? Isabelle had explained it: one successful procedure could be a gateway to more. It wasn't even about vanity anymore. It was about becoming who he was meant to be.
He hit record on his phone.
Riley shifted on the bed, the sheer black nightie sliding up just enough to hint at the lace panties beneath. He leaned into the lens, chest forward, lips pouty, eyes lidded. He had memorized the rhythm by now: tease, lean, moan. Whisper something hot. Let the lips part like an invitation.
"I missed you today," he breathed, running a finger along the top of one breast. "Bet you missed these too…"
And yet, even as the content flowed from him, practiced and sultry, his mind wandered. As it always did.
To Chase.
The fantasy was never far. Chase's thick arms, the way his gym shirt clung to his chest, the heavy shape of him—especially below the waist. Riley had seen the bulge plenty of times. Stared at it more times than he could count. That heavy outline burned itself into his thoughts like a brand.
And late at night… or during his "meditations" in the bathroom… that was the image that always brought him over the edge. Not girls. Not even Isabelle. It was always him. Always Chase.
Riley pinched one nipple through the fabric and whimpered for the camera. Then slowly lifted the nightie, giving his subscribers a peek at what they were paying for.
He imagined Chase watching.
No—he hoped Chase was watching.
Chase had said he followed him online. Had called him beautiful. Said he loved the content. Said Riley "won the internet." The memory made Riley's pulse race.
He kissed the tip of one finger and blew it toward the lens, then sucked the same finger into his mouth, slow and needy. But even that made his thoughts veer toward kissing. Toward him.
Riley wanted it. Desperately.
He'd practiced, of course. Isabelle had let him. But kissing her felt… off. Not wrong, just wrong for him. Kissing a woman reminded him of their past. It felt too soft, too familiar, like kissing the past instead of the future.
No, the only time it ever felt good was when he imagined Chase in her place. His lips. His grip. His need.
And Chase had needs. That's what girlfriends were supposed to learn—how to understand a man's needs. Isabelle had said so. And Riley believed her.
That's why he made content like this. Why he dressed the way he did. Why he practiced his moans and perfected his camera angles. It wasn't for validation.
It was for education.
How could Riley become attractive to women if he didn't first learn how to be a good girlfriend? And how could he be a good girlfriend if he didn't understand what men wanted?
He bit his bottom lip and moaned again—genuine this time—as he imagined Chase's hands on his chest. Not just watching. Touching. Grabbing. Kissing his lips, rough and hungry, holding his waist, grinding into him…
Riley lost track of time. Lost track of the camera. One hand slipped beneath the panties, and the other groped his chest as the fantasy bloomed—Chase pinning him down, kissing him so deep it left him breathless.
By the time he came, it was with Chase's name on his lips.
Panting, dazed, sticky, he tapped the camera off and fell back into the pillows.
That was a good one. Isabelle would be pleased. She always loved it when his orgasms were genuine. Said she could tell, that it felt more authentic. She'd edit it, boost it, caption it with just the right hook to draw in more subscribers.
He needed those subscribers.
He needed the money.
Because there were so many things he wanted next. Bigger hips. A rounder butt. Laser hair removal. Vocal training. Each one would bring him closer to who he was supposed to be. Riley was on a mission, and whatever he had to do, whoever he had to become, would only bring him closer to perfection. Closer to what Chase deserved.
And then there were the clothes. New lingerie. Thirst-trap sets. Anything with lace, mesh, or latex. Isabelle said the right outfits boosted engagement, and Riley believed her. He'd need a whole new wardrobe. And tuition was coming up, too. That wouldn't pay for itself.
But it would be worth it.
All of it.
Because GirleyRiley was a work in progress—and every step, every surgery, every moan on camera, brought her closer to the real thing.
He reached for his phone. Reflexively, he opened Chase's profile.
New pic. Fresh from the gym. Tight shirt. That bulge again.
Riley's breath hitched.
It was time for another meditation.
What's next?
Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
- 5,860 Likes
- 2,189,420 Views
- 931 Favorites
- 620 Bookmarks
- 384 Chapters
- 73 Chapters Deep
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