Tony Stark was relatively well known at the Playboy Club. Well known and liked. Though he paid his twenty five dollar yearly membership, he probably didn't get the full value, because he didn't go often. More often than not, the bunnies could be found with him in various locations around the city that weren't the club. Still when he walked into the place, he was treated like a king. The staff knew that when Tony came there was every opportunity to pick up an extra half-week's pay just for bringing him a drink.
Tonight when he walked in, the bunny at the coat check snapped to attention after giving him the briefest of curious looks. He'd always come alone (though he'd never left that way), but tonight his new assistant trailed behind him. "Let the girls know to treat him well, would you?" he murmured to her, slipping a twenty from his wallet. "It's his first time."
He wasn't sure whether Ianto looked completely comfortable or not, but as Tony had explained to him in the car over, "if you're going to work for me, these are experiences you need to have." Why these were experiences he needed to have, Tony didn't bother to explain. Admittedly, there wasn't much of an answer to be given aside from, 'because this is what I'm doing tonight, so you're coming with me'. Didn't matter though. As he led them up to the Living Room floor where the atmosphere was set by a piano player in dim lighting, Tony was sure that both he and Ianto would have an evening to remember.
"Two whiskeys. Top shelf," he ordered for them after they'd slid into a booth. "Becky, this is Ianto, my assistant. He'll need a key." His hand brushed up against her thigh as she left to get their orders.