I'm 75 and have been masturbating regularly for 64 years. That must seem amazing to some people, but, for me, it's been a way of life. I've also been married for a half-century and my wife and I still enjoy sexual relations.
My sexual fantasies frequently involve women with whom sexual activities remained unfulfilled, sometimes because of the woman's reluctance, sometimes due to my own missteps or hesitations, sometimes due to unforeseen circumstances. Because one cannot re-do the past, these episodes remain obsessive regrets. One incident, going back more than 50 years, was with Kelly.
I was in my second year of college, Kelly was in her first. We were outside the student cafeteria when a sudden downpour prompted most of us to seek refuge in the vestibule of the cafeteria. I did not immediately notice Kelly, who was standing near me, until she started talking to me. That's when I noticed her. She was wearing a skirt with straps that were pushed aside by her substantial breasts; the straps, in effect were framing her breasts, and I found that intriguing. The rest of her body, as much as I could determine, was astonishingly attractive. And her face was astonishingly unattractive: she was truly homely, and her poor complexion was unsuccessfully covered with excessive makeup. As she began speaking, and I realized she was extremely witty and clever. We spoke for a while, and in following weeks, we became good friends. I occasionally had girlfriends, often did not; I don't recall that she ever had a real boyfriend.
One day, after we had known each other for almost a year, we had been to the beach and I drove her home, where she lived with her parents. We went to the second floor, which she occupied herself, having, asides a bedroom and bathroom, a substantial sitting area, where we talked. In the course of our conversation, I happened to mention student athletes, whom I referred to as 'jocks.' This caused her to laugh, and she explained that she did not understand the term 'jock strap' when she had first heard it, thinking that people were saying 'jockey caps,' and the context simply didn't make sense. I asked if she knew now what a jock strap was, and she said she did, though she had never seen one. I took the cue. In those days, men's bathing suits did not have webbing and we wore jock straps under our bathing suits. I still had my bathing suit on under my shorts, and quickly pulled both down, standing there in my jock. She was shocked and said, 'Don't do that.' 'It's no more than my seeing you with a bra,' I said, and she looked more closely. Then I turned, and she laughed upon seeing my exposed rear. 'The treasure,' I said, 'is what's under the jock,' and proceeded to remove that.
As she had never had a boyfriend, I guess this was the first time she had seen a nude male, other than statues and paintings, and curiosity overtook any reluctance to have a close examination. She was astonished at my size, especially since I am not of particularly tall stature, and asked if she could touch, which, of course, I agreed to.
I asked if she would like to watch me masturbate, and she nodded. I said I needed some inspiration, and she would have to remove the top part of her one-piece bathing suit. (This was before bikinis.) She refused, saying she couldn't do that, that I would be disappointed. 'I've obsessed over your breasts for the past year, and must see them.' I went to pull the top of her bathing suit down. At first she put her hands up to stop me, but then allowed me to continue. I was not disappointed and proceeded with my part of the bargain.
She was astonished to see me ejaculate and said she had never had an orgasm. I had found, in my limited experience up to then, that some young women had orgasms very easily, while others required much effort on my part to help them climax. Kelly, I realized, was in the latter category, and I told her I could help.
'What could you do that I can't do myself' she demanded, skeptically? 'Someone else's hands feel much different from your own,' I said, 'and, besides, I could use my tongue.'
'Cunnilingus?' she gasped, and then became silent. She seemed to be considering the matter, when a voice came from downstairs. 'Are you home, Kelly?' It was her mother, who proceeded to walk up the stairs. We quickly assembled our clothing before she entered, I was introduced to her, and left soon afterward.
A couple of weeks later, I realized we were never to continue our adventure. Kelly had obtained her first boyfriend, and they had spent a night together in a motel. (She had told her mother she was staying with a girl friend.) I asked if she had had an orgasm, and she said she had not.
We remained friends until I graduated, but there was no more sex play between us. I last saw Kelly a few years later while registering for graduate classes. She was also registering, and told me she was now married (to that first boyfriend) and had a son. We talked while I went with her to her apartment, on a seamy side of NYC that was soon become known as the East Village. The baby sitter left, we talked a little more, and then I left, never to see her again . . . except in my fantasies.