Play up the young noble lady in need of assistance approach

You suppose this is a fairly simple attempt at using your feminine wiles to get something, so you do as the Enchantress says and go for it. With your current looks, it shouldn't be too hard to get such a minor favor by fluttering your eyelashes a little. Figuring you'll have it easier without Dennis' zombie-like presence along, you quickly find him, ordering him to follow along discretely once you leave town...he should be able to manage as much with magic, right?

Affairs in order, you approach the merchant cautiously, nervous in spite of yourself. His guards stiffen up at the approach of an outsider, but do nothing to stop you; they probably don't see the attractive young woman in a dress as a big threat. As for the merchant, he seems to be double-checking his preparations regarding the wagon, but shifts his attention to you almost immediately once it's clear you're approaching him.

"Ah, may I know why I have the honor of being graced with your presence, My Lady?" He either takes your garb to mean you're a noble, or wants to flatter you, but in either case, it works out well enough. Before you even have time to speak, he has your hand clasped in his, giving the back of it a light kiss as he bows. "Jefenir the merchant, there's nothing under the sun that I don't sell. Please, let me know how I may be of service."

You're a little taken aback, not sure if he's so friendly because he's essentially a salesman, or because you're currently an attractive woman. Maybe both. In any case, this might be easier than expected.

You pretend to act a little ****, but since he did ask... "Well...I don't want to impose, but...I've found myself devoid of coin, and somewhat far from my home in the city..." You trail off, as if unable to bring yourself to make such a 'brazen' request directly.

Jefenir slaps his chest resolutely, laughing. "Say no more my lady. It will be my honor to take you along. I'll have a space cleared on the wagon, and I insist you let me handle your meals."

You're already planning out a few more pitiful-sounding lines, and blind in surprise at Jefenir's words. W-was it really that easy? He didn't even ask any questions or imply some kind of future payment. "V-very well. Thank you for your help, good sir."

True to his word, Jefenir has a spot cleared, then cushioned for you in his wagon in a matter of minutes. With no further complications, you find yourself on the road, the horse-drawn wagon trundling along at a slow but steady rate, with Jefenir and his guards taking turns resting up near the front and walking by the sides.

Jefenir finds time to walk near you at the back, asking you questions about your destination, which you nervously deflect. You probably come across as suspicious, but he never calls you out, thankfully enough.