Proving He's Worth It

Tyler never imagined that one flirty DM would be the start of his total undoing.

She was out of his league—way too hot, too cool, too... everything—but when he matched with her, he took a shot. She didn't say much at first. Her messages were teasing, distant. But when he begged her for a chance, she didn't say no. Instead, she asked, “How dedicated are you, really?”

That’s when the tasks started.

At first, it was harmless: wear panties, shave those hairy legs, try some clear gloss. He'd send her a photo and she'd reply with a single emoji. 😏 Or sometimes: “Cute. Try pink next.” He told himself it was just to prove how much he wanted her, how open-minded he was. He'd do anything for a girl like her.

Weeks passed. He had an entire folder of selfies: soft skin, bright red nails, pouting in little skirts and thigh-highs. His closet was slowly becoming hers. And the more he obeyed, the more attention she gave. Flirty voice notes. Thirsty compliments. She even called him her pretty little doll. And that did something to him.

So when she finally said, “Come over. But wear something slutty,” Tyler obeyed without hesitation—even if his stomach twisted the whole time.

He stood in front of his mirror for a full twenty minutes before leaving the house. His hands trembled as he adjusted the white blouse she told him to buy, the short tartan skirt riding up every time he shifted. The stockings clung to his thighs like second skin, and the black patent stilettos made him wobble like a baby deer. His lips were glossed and puckered, cheeks dusted pink, lashes long and thick. He looked like a desperate little schoolgirl—and somehow, it made his cock throb in shame.

When she opened the door, she was wearing the exact same outfit.

Before he could even stammer a word, she grabbed him by the collar and pulled him into a kiss. Deep. Wet. Claiming. His head swam. All of it was worth it. She wanted him now. He knew it.

Until the door opened again.

Two tall, broad men stepped inside, smirking as they eyed the two of them. Tyler turned, confused, heart racing, but she just leaned in close and whispered against his ear:

"Be a good girl and follow me."

Her fingers laced through his, leading him down the hall, both of them swaying in their heels. He didn’t dare resist. His thighs rubbed together, heart hammering as they reached the bed. He barely had time to think before she bent over and gave him that look.

A moment later, he was right beside her—both of them bent, skirts hiked, heels high in the air. The men didn’t wait. Hands gripped hips. One sharp thrust and Tyler gasped, face pressed into the mattress, lips parted in shock as his hole was stretched wide. His fingers clutched hers tight as moans slipped from both their mouths, one thrust after another rocking them in sync.

She was louder than him. Shameless. Filthy. And he tried to keep up, whimpering like a needy girl as he was used right beside her.

His man grunted above him—one final, brutal thrust—and Tyler felt the warmth flood inside him, pulsing, hot and humiliating.

They were left there together, chests heaving, lips kiss-swollen and holes dripping. She glanced over and gave him a lazy, smug grin.

"You did good tonight, babe. Let’s see how dedicated you really are next time."

Tyler just nodded, still bent, still panting, still full… and utterly hers.