So after you talk to the guard at the gate for the first time, talking to him from the front doesn't do anything for some reason, however you can still talk to him if you stand to his left or right side. Alternatively, you can just walk up to the gate and interact with it but you'll miss the lewd scene.
Edit: Forgot to mention something. Once you go through the gate, if you're character is super slow it's a bug and it goes away once you do an attack.