Smuggled In Your Associates' Ass

You, a shrewd businessman/woman, and your sibling, a notorious importer of many illegal "small folk" goods, decide it's better to have someone on the inside of the city to deal business rather than have your clients come all the way to the outskirts. So you ring up your associate and professional smuggler Jesse to smuggle you inside and safely transport you to the, quite literal, criminal underground.

I do take suggestions!

Art by @ghostfuckrr