Warnings include: language, prostitution, blood-sharing, not-quite-explicit sex, and constant mentioning of established Damon/Stefan relationship.

Inspiration: Damon in a leather vest.

What the hell?

Damon ran his hand over his bare stomach and adjusted his vest. His fucking leather vest. The dank odor of the wet roads and the smells he didn't want to think about coming from the ally were upsetting. This was an insipid idea. He was Damon fucking Salvatore. And here he was in tight black leather pants and an open vest whoring himself out like a cheap trick. This was the worst idea Stefan ever had. It was supposed to be some sort of experiment. Stefan was convinced Damon was getting bored with their sex life. Hardly true, but Stefan wouldn't believe him, so naturally he gave in to his brother's whims. Now here he was dressed like an escaped slave from some S&M club, loitering on the street, and supposedly picking up a new partner for the night. No trace of Stefan since his brother dropped him off and drove away in the Camero a half hour ago.

It's not like they had been remotely monogamous in their lifetimes, but this one-sided role-playing lost a little something in the translation. If this were a real profession he would have done it right. Full tailored suit, maybe a cane. Better shoes. Perched in a hotel bar, not walking the streets in the middle of the night.

Fuck.

He stopped pacing as a black sedan turned the corner towards him. There weren't many reasons people drove to this street in this part of town. They were all looking for some company but it only took half a glance for Damon to be disinterested. The car was all wrong. Generic people drove generic cars and the only reason Damon agreed to this was because Stefan convinced him he'd probably get dirt on someone interesting. He was already rolling his eyes.

The car slowed to a stop in front of him and the tinted passenger window slid down a crack. A balding middle-aged man leaned over, squinting, as he looked Damon over. Fucking pig. He looked like a suburban dad, nervous and horny. "How much?"

Damon scoffed. "If you have to ask you can't afford it."

The creep's face flushed bright red, even in the dark. "Do you take cards?"

Shit, a first timer. Bending down to look into the car with his arms crossed tight over his chest Damon practically growled. "Fuck no, I don't take plastic. What do you think this is? Besides what would you tell the wifey when 'Back Ally Fuck' showed up on your Visa statement?" The rhythm of the guy's heart picked up and tempted Damon for something entirely different. This wasn't why he came here and he briefly considered drinking the man to dust. "Get out of here. Go home."

He watched the car speed away and turned back to the tunnel under the over pass. It was boring waiting by himself and maybe he wanted to fight a little with the other whores over stupid things like territory or the proper amount of snugness for a cockring. If this was going to happen, he was only interested in a certain kind of john anyway and who knew when that would show up.

Eying the women carefully, he avoided their glares as he leaned against the wall and sighed.

Damnit Stefan.

o0o0o

He turned away seven other cars over the next two hours. His female colleagues shot him a withering glare each time. He heard their whispers about him being ungrateful and giving the spot a bad reputation, but as usual, he was massively disinterested in what people thought of him.

It was around that time a silver Porsche turned the corner towards them. The girls stood straighter, pushed their boobs out and tried to look less used-up. Damon merely crossed his arms. The car stopped and the passenger window rolled all the way down. A woman tottered forward in her ridiculous heels and leaned into the opening briefly before turning away, glaring at Damon.

"He wants you."

Damon smirked, bypassing the woman without coming into contact with her. "Of course he does." Figuring he'd be disappointing another misguided suburbanite Damon took his time. He made his way over to the window, leaning his hands against the edge.

To his surprise, the man behind the wheel wasn't at all what he expected.

"What's a guy like you doing a in a place like this?" He tried for a playful tease, but it lacked his usual bravado.

Mostly in shadow, only Damon could make out the smirk on the man's face. "Get in."

"Tsk. I don't think you can afford me, sweetheart."

"I wasn't asking." The reply was smug, like he was used to getting his way. It demanded Damon's attention, intriguing him. Instantly his plans of turning everyone away changed.

Pretending to think about it, Damon looked around the road. He had been stuck waiting for whatever Stefan had planned long enough. If Stefan insisted he do this, he might as well stop half-assing it and get into character. With a glance back to the driver he ran his tongue over his teeth. Might be worth it.

Shooting the wilted women a smug smile of his own he made the decision.

He opened the passenger door and slid in, eyeing the driver. He was young, but obviously strong. Soft hair with a firm chin and a classic renaissance beauty. There was also a roguish glint in his eyes that made Damon think about being a little worried. Just how he liked them. He supposed he should feel guiltier. If Stefan wanted him to do this, well, who was he to argue? With a blink, he flipped the switch and stopped worrying about his brother.

He turned slightly and ran his hand down the driver's strong thigh, then back up to his groin before the man slapped his hand away. So, it was going to be like that.

Damon leaned up to the man's ear, sliding a hand around his arm. He smelled like expensive cologne and warm blood. "What do I call you?"

The man only laughed. "Does it matter?"

Pulling away, Damon righted himself in the passenger seat. "Just want to know what name to be screaming out in a bit."

The man shot Damon what could only be described as a lecherous grin. "How about, 'Matthew'?"

Damon grimaced. "Nevermind, no names. We'll just have to wait and see whose name I cry out."

Looking back to the road, the man pulled the car into gear and headed off. "Guess so."