Admittedly, I’m as gay as a guy can get and, while I’m personally not transgender or into cross dressing myself, I would respond to someone who is and has gotten stuck with great enthusiasm, kindness and respect.
That said, those who might be just starting out or feeling anxious or nervous about venturing out to get stuck alone wearing an exciting new outfit or maybe sporting a hot new style, absolutely go for it! But please, I would recommend having it prearranged so that a trusted friend is there at the site to check on you after you’ve had a certain amount of time for getting stuck and spinning your tires in high-heeled, pedal pumping ecstasy. Then you can continue on spinning as you were, or at least you’ll have someone there to help you get out of the mud when you’re finished.
The idea is not to be totally alone and stuck in the mud. Just like when meeting someone new on a first date, someone always should know where you’re planning to go, and whom—if anyone—you’re planning to meet. Have someone on their way to meet you, even if it ends up being that the person isn’t needed and you get out of the muddy situation without any help. Be safe out there: we all need to stay safe and stuck together in this!