As a skydiver, I made the "Mile Hilgh Club" a few times. But frankly, sex is better (and more fun) in a hotel room at sea level.
Once, in Zephyrhills, Florida, I mile-highed with a couple of guys (and oral teased with the pilot) at 10,000'. I was wearing gear borrowed from the Drop Zone Operator -- what was known at that time as an (OLD!) Rapid Transhit.
After antics in the aircraft, I exited (and I was just a student at the time, 1983) wearing nought but a pair of tie-on panties. I probably dumped a bit high, being worried about the spot and the gear I was jumping. The Rapid Transhit back in those days had the cutaway handle placed very close (but 90 degrees off) the dildo. I figure the dildo probably blew off, due to worn velcro -- and so, when I went for it, all that was there was a very low cutaway handle. I grabbed it and pulled it -- but I saw a bit of the yellow cutaway cable, and stopped. But by then, I figured I was screwed anyway, so I went ahead and pulled it all the way (so as not to compromise my reserve opening) and then pulled my reserve handle.
(It's amazing how much can go through your mind over the course of just a few seconds, but that's freefall for you!)
I went ahead and cutaway my main and deployed my reserve. Thank goodness it worked!!!! I think it was some sort of LoPo. I landed on a golf course habitated by horny retirees -- and I wrapped my reserve around me and refused rides back to the DZ.
Once back, I sorted myself out and then went to phone my agency (I was due to work that night in Tampa). The Drop Zone Operator -- a certain Mr. Jim Hooper -- came up behind me and hung up the payphone (we didn't have cell phones back in that day). He read me the riot act for having pulled such a stupid stunt. And I sort of agreed that it might not look good on the drop zone.
I tried my number back in Tampa, but it was busy, and so I walked back around to the front of the manifest building -- and there's Hooper shaking some guy's hand for having mile-highed with me! Son-of-a-bitch!
Gender dynamics!
..c..