Totally Worth It

“Hey man, I won a new Xbox and was wondering if you wanted it?” Josh perked up immediately, eyes lighting up. “Wait, seriously? Hell yeah, dude!”

Chris just smirked. “Of course, bro. I just need a little favor in return first…”

That was how Josh found himself seated in front of Chris’ sister’s vanity, blinking at his reflection in horror. His lips—plump and glossy. His eyes—framed by thick lashes and shimmering eyeshadow. His cheeks—perfectly contoured to give him soft, feminine angles.

And his outfit… dear god, the outfit. A tight, heather-gray crop top that barely covered the absurdly large fake breasts strapped to his chest, paired with a curve-hugging mini skirt that made his freshly shaved legs look way too good.

Josh shifted uncomfortably, wincing as the falsies pressed against his chest. “Dude… what the hell is this?”

Chris leaned casually against the doorframe, arms crossed, grinning like the devil himself. “Do you want the Xbox or not?”

Josh gritted his teeth. He could deal with this. It was embarrassing, sure, but they were just messing around at home. No one else would see him like this.

Except—

“Alright, time for dinner,” Chris announced, tossing Josh a tiny purse.

Josh blinked. “Wait. What?”

Before he could argue, he was being ushered into Chris’s car, his barely-there skirt riding up his thighs as he nervously smoothed it down. The restaurant was nice—dim lighting, romantic ambiance, a place meant for dates. And that was exactly what this was.

Sitting side by side in the booth, Chris’s hand wandered over Josh’s smooth thigh, his touch light and possessive. Slowly, his fingers crept higher, tracing soft circles against bare skin before teasing the hem of Josh’s skirt—dangerously close to his panties.

Josh tensed, swallowing hard as his breath hitched. He leaned in, voice a furious whisper. “The hell is this?”

Chris just smiled, squeezing his thigh. “Do you want the Xbox?”

Josh exhaled shakily. He was in too deep to back out now.

Dinner was torture—Chris ordering for him, the waiter calling him ma’am, the subtle expectation that he giggle and play along. He had never felt so small, so powerless. By the time they left, Josh thought the worst was over. He kept his eyes down the whole ride home, barely speaking, already dreaming of locking himself in his room and forgetting any of this ever happened.

Chris pulled into the driveway, shifting into park just as Josh reached for the handle. “Hang on,” he said casually, that same cocky grin tugging at his lips. “There’s just one thing left before I hand it over.”

Josh turned, confused—then froze. Chris’s pants were around his knees, his thick cock standing hard and ready, shamelessly on display in the dim interior light. Josh’s mouth fell open.

For a split second, he was ready to throw the door open and bolt. Just run—screw the Xbox, screw the makeup, screw the whole thing. But he didn’t. His stomach churned as he thought about everything he’d already endured. The lashes, the breasts, the dinner. The way Chris’s hand had crept so high under his skirt. And now… the Xbox was so close.

He swallowed hard, then turned back slowly, defeated. Lowering his head into Chris’s lap, his glossy lips parted and slid around his roommate’s meaty cock.

Chris finally handed it over, the sleek black box practically glowing in Josh’s arms. “Go on,” he said, smirking as he raised his phone. “Pose with it for me.”

Josh didn’t hesitate. Still flushed, still breathing hard, he sank to his knees on the hardwood floor, clutching the Xbox like it was some kind of trophy. His fake tits spilled out of the tight top, cleavage front and center, glossy lips still slightly parted, smeared just a little.

He held the pose, arms wrapped around the box, his skirt riding high, knees spread just enough to keep balance. His chest heaved with each breath, the faint, lingering taste of Chris still coating his tongue.

And yet, as the shutter clicked—he couldn’t help but smile.

Totally worth it.