I've already done it several times for single guests at our gîte. Here are my ideas and what has been done in real life: 
- Game space: several were done on our private land so, no risk of being bothered by the police. No restrictions on nudity or dress. 
One of them did it as a dog (legs tied bent + wrists handcuffed to his neck chain). 
Below is what you can adapt to your region/country:
- Game area in the countryside (on foot) 
Visible clothing: trousers fastened with a chain belt + a padlock + closed rainwear. In the trousers there were nappies / plugs / Ballstretcher / tights / female underwear. 
The handcuffs were attached to the waistband of the trousers (in a chain) and were not visible as they were hidden by the raincoat. 
- Space game in the countryside (by bike)
I hid the keys in the countryside, then gave out the treasure hunt AND lent a bike. 
Visible clothing: trousers fastened with a chain belt + a padlock. In the trousers there were nappies / plugs / tights and female underwear.
- In Urbex
We have some Urbex sites near us. I go cycling early in the morning. Twice on this leisurely ride I've hidden keys in an abandoned hotel to please a nice guest (I don't do it for everyone). 
Then I took the people in the car and dropped them off behind the ruined hotel, they gave me their clothes and had to close the handcuffs --> Hands in front for safety. One of them was dressed as an adult baby, the other as a woman. We took the opportunity to take a few photos once they were free.
NOT TO BE MISSED: 
I'm a pervert but that's why people love me LAUGHING. 
I did selfbondage when I was young, and I've been dominating men and women for over 35 years. 
I've been using the principles of self-bondage in my domination for a long time. 
I guide, advise and help our customers who want to play and lend them equipment. I have a spare key in case of problems. 
What I say is real, I don't invent my own life.