It seems strange that I don't remember any anal masturbation in my late teens and early twenties. It was so much a part of me, I couldn't have left it for that long. But I will tell you that after the things I did at age 15 with my sleepover friend, I went through a time of denial, so afraid that I would be gay. The word 'gay' had not yet been co-opted for homosexuality in the Sixties. The terms in use were homo, queer, fag. It was NOT an accepted lifestyle and I knew nothing about the idea of being bi-sexual. Homosexuality was not talked about then, except in negative terms. I felt I needed to shut down that side of myself to make sure I would have a good and 'normal' life.
In my mid twenties, a girlfriend and I started masturbating together occasionally. I had always done it in secret, and was obsessed with wanting to know what girls did. To kneel between her legs and beat off watching her rub her clit and move her hips was incredibly sexy! OMG, I LOVED seeing her finger disappear inside her. It gave me such a feeling in my stomach. I loved that she could see my hard dick and know I am beating off. I loved that I could come on her stomach or squirt all over her nipples.
One day, on a weekend trip to another city, we visited a sex shop and bought a couple of vibrators: a small one the size of a lipstick and a large one about the size of a penis, but without the interesting shape. I used to crave having the larger one in me. One day a friend loaned us some porn flicks. We watched them and masturbated together. When the mood had built up enough, I asked her to put the vibrator in me. Bending over the edge of the bed with her standing behind me, it felt amazingly good to be fucked like that while watching erotic scenes, my hard dick under me pushing into the mattress! And by a female! A sexy girl doing it to me; seeing me beating off with something in me. The very things I had to hide as a deep, dark secret in my teens.
We didn't use those often. Usually it was just having her finger in me. If we were doing things and I was in the extra horny mood, I would ask her to just tease me there. I knew she didn't like doing it, so I had to build up to asking, feeling almost wild with the urge and anticipation. Sometimes I would go into the bathroom and put the Vaseline between my buns ahead of time, knowing I was going to want it. Feeling her finger teasing there made me CRAVE the hot feeling of having it slide in me just a little bit. Then, I would be greedy and want it all. I loved kneeling on the bed and beating off with her finger in my ass!