Jacob hesitates. Its only for a moment as Victorian sensibilities fill his head, and then he gets over himself. Yes her tail is only just above a very shapely bottom, yes she really isn't wearing very much at all right now, but she's also uncomfortable with her tail caught up in that fabric and he can clearly see she can't get herself free. Connor would think he was ridiculous if he tried to voice his uncertainty, and so what? He's literally just undressed with her in the room.

He moves closer, surveying the problem and not her backside, honest, and with one hand gently begins to shift the fabric of her dress away from her tail. And then, with the other hand, he carefully, gently, takes hold of her tail to untuck it.

"You know, I don't think any other woman I know has this problem." He says conversationally, "Then again, I don't think any of the men I know have this problem either. And Charles doesn't much go in for clothes when he has a tail. But who is going to tell a werewolf he's not properly dressed?"