I have done a ton of things over the years that I should probably be ashamed of. Most of them are not really in line with the topics of this forum. That said, a couple come to mind.
I sometimes catch people on one of my ranches "parked". One property was especially known as a place where young couples could go to party and get it on. We were constantly trying to keep people off because of liability and messes. More than once I caught people there and ran them off with a rifle in my hand. This one time there was this young couple fucking in the back of a pickup truck parked at the end of the drive in front of a gate. I saw the truck from the reflection of the sun when I was a long ways away. I decided to check it out before I confronted them and left my horse and went up on a bluff that ran parallel to the drive. I was about 50 yards from them. Rather than leave them alone or confront them right away I just laid there and watched with a pair of binoculars. They finished and I came down to run them off.
There was this guy our senior year of HS that was a total dweeb. How he landed one of the hottest girls in school as a GF is beyond me. Anyway one time he cut me off in the parking lot and took "my parking spot" (not officially assigned we just all had our spots and there was a pecking order which I was near the top of). I told him to move and he said something along the lines of "what are you going to do about it". Well I worked at it over the next few weeks and stole his girlfriend. She was hot but we had nothing in common. I kept her around for a month or so and rubbed it in every chance I got. Then I dumped her. That was fucked up to both of them.
The final one was the same year. There was a girl that had a reputation as being super prude and conservative. She was president of the Bible study club on campus. She looked like a young Elaine from Seinfeld. My buddy bet me $100 (a good chunk of change in 1998) that I could not get her to hook up with me. It took me over a month to get her to even go on a date with me then another 4.5 months to get her in bed. The whole thing was so wrong. I felt bad for years. I really hurt her. I also wished for years that I had not let her go. She would have made a great wife.
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