Ashley stepped up first with a huge smirk on her face, "heya big guy, after all this ruckus. I've decided that the church route isn't for me. I'm going to take my hard earned gold and register at the guild, could you perhaps give me a discount?" She ended sweetly.
[1d20+4=14 Ashley attempts persuasion without proficiency vs DC20]
He laughs heartily, "what do you have to offer me there little miss? Maybe I could throw you a gold, I could use some company tonight."
Ashley's expression dropped, "I ain't that type of little miss, sir. But if you know what's good for ya, maybe you should at least offer to buy a girl a drink."
&[1d20+6=16 vs DC20 Ashley attempts intimidation and fails once again.]
He laughs harder, "Well aren't you a spicy one, but I'm sorry lass, my heart belongs to another way above your rank in beauty and grace."
Ashley furrows her brow and waves him off, "Pft, whatever, at least I tried" she glances at Yulya and shrugs. "So anyway, Mr. Guard, Sir, can I go? I need to get registered or I won't be able to eat right? I haven't eaten for days, I'm starving here! Do you want this incident to cause a real death?" She leaned in on him in an insistent way, sucking in her cheeks slightly, exacerbating her already gaunt appearance.
&[1d20+6=19 vs DC15 Ashley attempts to use deception to get the guard to let her go and it succeeds.]
The guard shoots her an annoyed look and throws his thumb over his shoulder, "see that you get registered without more ruckus."
Ashley winks at him, and then waves to Yulya and Cat, "See ya at the guild best buds," she said in a sing-song-y way and adds with a serious tone, "get a mask and robe and bring Alice, I'll butter them all up at the guild for yalls. Bye Felicia."
She steps past the big guy and slaps his stomach, "see ya there too I guess, maybe I'll buy you a drink."
[1d20+4=6 He clearly wasn't impressed by her charismatic charms.]
[1d20+4=7 The guard watches her go, unimpressed as well and frankly a little relieved to see that one on her way.]
The North Guard and Brutus both stare down at Cat and Yulya, buttered up as Ashley would say.
Four bells toll ominously in the distance. You hear the driver calling his animals into motion, the rogue rothe limping as he trails on a leash.
[The North Guard has asked for your statements for a start, Yulya and Cat obviously, Ashley was miraculously released without questioning and without incident and will meet you at the guild, she still has your 40gp. Though she requested you bring Alice, and in proper garb and mask, that's up to you, though it would help quite a bit if you did. - Signed, your humble, kind, and merciful DM Joy who you will do well to take advice from.]
[Again, this is your game, so do what you feel is right. I will also add as a bonus gift of knowledge you should have figured out given the previous information: the shops will sell to Yulya and they won't question Cat as the townsfolk are used to seeing refugees and many of them are walking around unregistered, many gave all they had just to enter the city with nothing left to eat never mind to pay to register at the Adventurer’s Guild or Hall of Justice.]