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Do you drop an article of clothing at intervals until you just can't go on for one reason of another. Then do you go back and retrieve them before going back home?

I pictured this traveling down an interstate highway. The return trip would be going back on the other side so you would have to make some switchbacks to collect them. Even if this were done on city streets you would need to switch back to be on the correct side of the street or exit the car to cross and get it.

So I imagine traveling to a far off location for business or pleasure. You have estimated the time of travel. Divide that by the number of arrivals (plus or minus 1 or 2). Drop at this intervals. If you have a safe place to stop once you get there then arrive undressed. Otherwise put on clothing somewhere near your destination. The second set of clothing might be in the trunk/boot of the car.

On the way home (maybe a week or weekend later)start undressed as you arrived. Do whatever switchbacks are needed to reaccquire your clothes. You have to decide how long to search for each one. Someone or the rain may have taken it away? How important is having that shirt when you arrive home?

Would you risk leaving a chastity key?