Ive always played it safe but I did have one experience that was somewhat risky.
I have a buddy who once had a gorgious mare. Weve met on the old beastforum site and knew each other for about 4 or 5 years. He lived about an hour away and getting our schedules to line up to hang out was difficult. One weekend we managed to get a saturday freed up and he took me out to meet his mare at the stables he had her boarded at. I would say this was at about 11am. He took me around and showed me the place while going to the other end of the place to meet his mare. She was a sweetheart and everything ive heard about her over the years were true. We took her out, brushed her down, ran her around. Meeting her was all i was expecting that day and was fine with that until he suggested "we take a walk."
Well across from the barn was an orange grove. To get to the riding trails you would have to cut through the grove. Im not gonna lie im sure it looked a little suspicious seeing two guys walk a mare to the grove but no one really noticed. We cut of the main trail, walked a ways deep in the orange grove until he brought us to his secret fun spot where he has a dirt mount thats the right height for standing behind her. Hes never let anyone play with his mare other than himself but i was honored to get the opportunity too. We both had our turn. Once done we took a slow walk back out sense she was walking, tail hanging high for world to see but by the time we got out of the grove she settled down. So probably the riskiest experience to do something like that in broad daylight and people around on a saturday but also the most memorable.