You slide another coin

You slide another coin, this time a higher value, look at the man, and nodded. Without saying anything, you're asking the guard to recommend you what to do.

The guard pocketed the money and grinned. "If you fancy yourself as a deep sinner and popular with the ladies, you may try to woo Miller's wife since he's here," the guard gestured to a man flirting with the courtesans. "He's a regular and will be here until morning. Seven house east from the well."

Wow, an outrageous suggestion from the get go. Instead of fucking a whore, you try to cuckold the customer here.

The guard next gestured to a bar maid who look surprisingly decent in term of looks. "She is available, but you have buy certain amount of ale. It's the price set by the house. And if she fancies you, she'll suggest you to take a nicer room."

"How to know if she fancies me?"

"Ask her for a recommendation before ordering, and she will tell you her favorite one. But it depends on her mood. You have to engage her."

"Makes sense."

"Ask for a nicer room and you will be brought to the nicer room and a nicer whore."

"Okay. Makes sense."

And..." the guard trailed, never finishing his sentence.

You slide another coin.

The guard leans in to whisper, "If you want to be an exclusive to one of them, negotiate to do it at somewhere else. That way they don't have to pay tip for the room. You don't hear this from me."