Enemas and anal fascination as a little boy led to anal masturbation in my teens.
In my teens I branched out, finding other things to penetrate myself with. On summer days after swimming with my friends and seeing the girls lying on their stomachs in their two-piece bathing suits (almost like seeing them in bra and panties!), studying the beautiful curve of asses, I would come home so horny. I'd go straight to my room and close the door, stand in front of the mirror in my wet bathing suit and prepare my mind for masturbation.
Sometimes I would tease myself by pulling my suit down just a bit in the back to see a little bit of white ass below my tan line and my hard dick bulging out the front. I could hardly wait to see my whole bare ass and my bare hard dick, but that was the tease. Then I would peel off my wet trunks and just look at myself, building up the craving to get the Vaseline and start beating off. On extra horny days if I was home alone, I would wander through the house naked and erect looking for something to penetrate myself with, usually my mom's douche nozzle, but sometimes other things. A roll-on deodorant bottle with a rounded cap felt good. A hair brush handle if I was desperate.
One time the only thing I could find was a deodorant bottle with a squared off end. I pondered the shape of it, craved being filled up but wondering how I would get it in me. I had to work hard to get it in but then it felt nice and big and round in my ass.
I liked to stand in my bathroom with my balls over the corner of the sink, feeling the cold ceramic tile against them as I beat off. There was a makeup mirror attached to the window behind me, so that looking in the mirror in front of me I could see my hard dick with my hand on it AND a perfect image of my ass. As I beat off, I would bend a little over the sink and imagine my ass being fucked. That was SO thrilling and erotic!
At age 14 and 15, I would have the occasional guy sleepover where we would end up masturbating and talking about girls. One friend would talk about his exploits with a cute, smart girl from our class, and I would be amazed that SHE let him do those things. I would beat off to the vicarious thrill of his hands down the back of her panties, feeling her bare ass. OMG!
When I was fifteen, my parents were going out with some friends and arranged for their son, who was 17, to stay with us. We went to different schools and did not know each other, but we ended up beating off and talking about sex. He asked the blunt question 'Have you ever had anything like a dick up your ass?' I said no but could have added that I'd had practically everything else up there. As we beat off more and talked about it, I was craving to feel it, thinking that would be the ultimate. (The next day, I was grilled by both my parents, who found Vaseline stains all over the sheets and my pajamas. I denied everything and had to listen to a lecture. It was horrible!)
My friend and I had several more sleepovers during the next several months, including a weekend while our parents were out of town. I can't write about what happened, but those are stored in my memory as some of my most erotic (and forbidden) sexual experiences. Fifty years later, I sometimes still masturbate to them.