Those guys who started experimenting anal in high school

All of the above, including the cheerleader.

Truth. It was the cheerleader (Captain) who introduced me to anal both ways, as a college freshman (we were both "legal age" at that time.

She was "saving her V for marriage" and didn't want to mess with birth control. She was also an anal wild-woman, and introduced me to giving (she wanted my fingers, tongue and penis in there on EVERY date, every time). She also introduced me to her finger, tongue and a couple crude toys of the day (that was nearly forty years ago!!!!).

I must say, to this day I wonder where on earth SHE learned to be so "proficient" with this activity, but she was really a class A expert. Even as a hormone raging young man, she was almost too much, sometimes, as she simply would wear me out, and still want more. Okay, at this point, I may as well give the whole story...the wildest weekend of my life.

Her parents went away one weekend, and she wanted me to "come over and stay at her place". I made an excuse about going camping with my best friend, to my parents and showed up on her doorstep on Friday evening. She promptly informed me...in exactly these words "I want to feel you in my ass, in that nice warm place, all weekend". She wanted to stay in bed...with me inside her...literally, all weekend. She wanted my ERECT penis there, and also to keep it there when flaccid between romps!!!! Other then a few trips to the bathroom, she wanted me there...at all times!!! The times when it just would not stay, my fingers "had to do". She had FOOD, reading materials, a TV, all positioned so we could STAY IN HER BED. When I had to urinate...yes, you got it, she wanted me to "stay in her" and just give her a "urine enema". Even when she was on the potty, she insisted I come into the bathroom with her, and I would stand in front of her, with my penis in her mouth, so she could get me hard...again, then it went right back into her butt...even before leaving the bathroom, and she walked "in front of me" impaled on my tool, to the bed, where she leaned over and said, "HARD...do it HARD".

I am NOT making this stuff up. That was, without question, the wildest sex weekend of my life and nothing before or since comes close. I am sure nothing will.

When her parents arrived home late Sunday night, I was just leaving and as they smiled and "thanked me for helping keep an eye on their house and their little girl while they were gone", I almost felt guilty for all that they DIDN'T, I'm sure, have a clue about.

Sadly, her family moved across country and to this day I have no clue what became of her.

I still appreciate the incredible "schooling" she gave me, and think of her fondly still...despite being happily married for over 3 decades now. I can honestly say I got to live one weekend of total insane sexual abandonment and fun. My own personal porn movie to replay in my head, for life.

Thanks Mary, wherever you are.

Using these items on yourself or the cheerleaders?

Fingers first, then a hair brush handle. I had heard that there was a "Spot" that would make you come faster and I was curious to see if it was true. Yup, it was. I used my fingers every once in awhile when I wanted to get of fast, a little over a year ago I started using toys. Never going to look back.

Thinking back, I always had a fascination with my butt.
I recall using an electric toothbrush with a perfectly smooth and tapered handle when I was in grade eleven. It vibrated a little when it was turned on, too. I had used other things before then, but certainly nothing very safe, in retrospect.

Of course, I have since found the joys of silicone and steel (and would like to try glass).