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Well, I did come close to "ejecting" a ziplock bag full of freshly manufactured sewer probes over the south edge of the Chicago Class B once. Then I imagined how I would feel if I was walking to my car to go to work and an unplanned rectal abortion blasted through my windshield.
My stink pickle cargo remained in the plane until we hit Iowa City, at which point it was offloaded into a nearby trash can.
Rest assured that there were extenuating circumstances involved, otherwise I would have of course landed and deployed the toilet trouts at an FBO.
We ended up stuck off the coast for an hour by Big Sur (California), once. We were orbiting, and the USFS Baron working the fire came up along side in our orbit. Our FE removed his nomex and mooned the Lead through the cockpit windows. The lead was close enough he got a very detailed digital picture and posted it on his web site for a time.
I told the FE we should have gone aft and opened the troop door. I think it would have worked better, but then I didn't know the leadplane was snapping photo's, either.
The picture that started the thread was a skydiving 182...understandable. A few weeks ago at a DZ I saw a King Air taxi out with a load of skydivers. Someone came running from the building and caught up with them on a taxiway. I thought they'd just got on the load late, but they stopped the airplane on the taxiway, bent over and mooned the load, and then went back to the building. Apparently just a token of affection.