When I first considered anal, I was around 9, and the 8-year-old neighboring farm boy would come over to build hay bale forts with me. We would take turns laying on each other with our pants down while rubbing our penises against each other’s anuses while inside of a bale fort. It was more of a game of playing grownups, than it ever was sexual.
My first time of actually having anal was with a younger hispanic girl. It happened in the grass behind the schoolhouse in a neighboring small town. I was 14, and she was a couple years younger. (It was her idea). I sprained my penis something horrible, and it was temporarily disfigured and very sore for over a week.
My girlfriend of 10 years while in my 30’s would alway offer her ass up to me on my my birthday. I have to say it was one of my favorite gifts! She seemed to enjoy it too.
In my 40’s I received my first anal fucking by a gay buddy as a part of a threesome. He knew what he was doing, so it was pain-free. It was amazing, and I really enjoyed it once I let myself fully accept it and him! I had my moments over the years of feeling some regret about that night, but if I had it to do over, I would, and probably more that once! I’m still not gay or bi, but life is way too short to not experiment. If a guy ever gets that chance to get fucked in the ass by another handsome man, JUST DO IT.
With all of the “anal education” leading up to my present wife of 10 years, I feel safe to say that she would say I’m pretty good at it. She never complains. Having anal sex with my wife is definitely better than my first time!
~“It’s only kinky the first time.”~