Dirty, well-rested, and stiff

The sound of the morning birds made you stir first before Mathis. Sleeping on the ground throughout the entire night resulted in more than a few annoying bug bites and the itch is insatiable. As you reach to scratch your neck, you open your eyes and see Mathis atop you. As a result of being stuck neck and neck with the gem shared between you, when he turned over in his sleep you ended up under him. Thankfully, all that weight he lost in prison made it so he isn't completely crushing you, but it is still quite uncomfortable. You try to move your legs from under him and it is then you feel Mathis' member on your thigh. You'd rather not jolt him too much from his sleep so you decide to wake up him gently.

"Ah hmm," you cough.
Mathis starts to stir and to your shame you feel him rub himself along your thigh as he comes to. "Well, Damn. This is awkward," he says as his eyes stare into yours.
"Would you mind, getting IT off me," you say in anger.
"Oh my, sorry, huh I usually wake up like that in the morning," he says as he takes the necklace off from the both of you and he gets up and sits right next to you. For a man who claimed to be spending his early youth wenching and drinking, his shame is quite amusing and you smile. Finally after his embarrassment settles down he asks, "What happened?"
You explain to him the events of the evening before and how his passing out left you both in a very exposed position. "Now that town ahead has a description of me and the soldiers are still there," you end.
"HA!" He scoffs, "It's not like we are walking through the front door, besides it's a big town, a few thousand people are easy to get lost in."
"So, how will we get in?"
"Easy, well sort-of,"
"Again with the sort-of," you respond.
"Hey, nothing in this short life is simple. The way I see it, we have two options. We can either commandeer someone's wagon and pay off the guards at the entrance or we can get down and dirty through the damn sewers, assuming they haven't changed much from my day," he says.
"By commandeer, you mean, I-assume," you are about to ask as he interrupts you, "Yes, I mean we are going to steal someone's wagon, their clothes, their money if you'd like to, and then use that plus some of your own coin to pay off the guard at the front entrance."
You are about to protest at the use of your own coin for this option when he says, "Don't worry, my brother will pay you back."
"There seems a bit of risk involved in this first option," you say, "You'll have to convince the guard of our sincerity."
"Actually, that task will be up to you as my cropped ears will get us forked faster than nicely cooked meat on a fatman's table," he says.

How well do you trust your own persuasive skills? You'll also need a hat. Would it not be simpler just to go through the sewers? You already stink so it is not like it can get any worse.