@TACOENCAJ_5 I've often wondered at the actual frequency a housewife from that time actually did get stuck. If you about it, there the post war boom in the economy which meant many could afford a second vehicle for said housewife. I've also noticed that round that time there were still a butt ton of unpaved roads around, even within the city itself.
Factor in the time of year (spring thaw) weather conditions, meaning rainy season, most all women of that time looked impeccable at all times, likely meant there were very well dressed stuck victims to be found

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

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

@stuckboy awesome! What do you do... like do you just dress up and just get stuck straight away, or do you like roll play, pretending you're out for whatever reason and you get stuck

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.

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

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

@So-Very-Stuck3 Sounds fun

@scotsman I bet! Sounds like fun

Sounded like quite the adventure

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

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"

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