Can't wait to hear more!
This is perfect.. slight hill, snow, helpless rwd car.

@So-Very-Stuck3 Sounds fun

@gabe I know woman stuck is almost taboo here, but I don't intend on posting them here but, I've been having the same issues, no matter how it's phrased or described, or even just using commas to separate the various criteria... I get the terms of use violation warnings.
I've been able to get some results but not the desired results or it's as some say, the girl is like part of the car or something stupid like that.
I personally think it's because the terms of use is written in a sexist manner and describing a woman in a stuck situation is objectifying her and it triggers the warning. Just my take on it
Might try the Bing AI generator

Anyone else getting their requests kicked back saying "something in your request might have triggered Microsofts terms of use" and im only describing a stuck scene, not sexual... then when you try again it says "we're experiencing a lot of guests right now, try again later"

I certainly liked the long skirt and the boots... excellent combo. Casual dressy

@Blackadder261 How was your outfit recieved?

I love the long skirt and the boots! Dressy yet casual.

There ya go... one tiny moment of inattention and zzzzzzzz oops

If a "certain outfit" is a bit outta your comfort zone, start out dressed down.
Perhaps jeans, a nice sweater, and heeled boots, then work your way into maybe a longer casual skirt, sweater and mid height heels and then when you're more comfortable with it go all out for the office attire or formal attire.
Play the "lost real estate agent" or the "real estate agent on assignment"

Just a simple " I made a wrong turn and pulled in here to find my bearings" would suffice perfectly.
Maybe an evening drive out nto the country is in order... would serve two purposes... 1 locate some possible locations to revisit, and 2 help build your confidence with being out and about while dressed. ( which you're gonna have to get used to pretty quickly given the info you've shared with us)

I completely understand the anxiety. And its easier said than done, but just doing it helps ease that too. Once that stuck cherry is popped and you see it's no big deal, you'll naturally get more daring.
But maybe until you get more bold, a simple "pulling over to check my GPS" type of stuck is best.... something you can easily rock yourself out of in a few mins as apposed to a pulling into a soft wet gateway and both your drive wheels are in it then... much harder to get out of

I think you'd be just fine.
Specially in this day and age.. people are much more accepting.
I'd love to stumble across you helplessly stuck.

Well, if you're in the beginning stages of transitioning, and it sounds like you present as a woman well, don't worry about getting unstuck. Most guys would trip over themselves to help a well dressed damsel in distress. Just hike your skirt up a touch and show lots of leg to an oncoming vehicle

Sounded like quite the adventure

Tbh... I'd rather her of been driving

@scotsman I bet! Sounds like fun