I have done a few times with wives and girlfriends, but probably one of the most memorable occasions was when I answered an ad on Craigs list, back when they still had ads for meetings.
The ad was from a lesbian who wanted me to watch her as she masturbated. There was to be no touching, but I was encouraged to masturbate at the same time if I felt comfortable.
She was a woman about thirtyish. Quite butch in appearance, but not unattractive. Smallish breasts, but nice hips.
If I remember we met at a motel she had rented. It had two single beds, and after we dispensed with the small talk she told me to pick one.
She lay on one and I took the other. She quickly undid her belt and unzipped her jeans and slid them and her boxers down her legs and kicked them off.
She wasn't shaved, but fairly short clipped so that I could see her pussy quite clearly.
I quickly discarded my jeans and shorts in the same manner. I was already quite hard at just the thought of what we were doing. I think she was already aroused too because I could see her fingers were fairly slick where they were sliding through her labia.
She kind of turned partially on her side to watch me. She told me she had never seen a man's hard cock. This certainly helped me lose any inhibitions about being too small in that department, and I redoubled my attention to my throbbing erection. I could tell pretty quick I was going to have to slow down or I would come too soon.
She noticed this and told me to hurry up as she was close to coming. That was all it took. A couple of quick hard strokes and I was coming and groaning like a person in agony. 😃
She started saying "Fuck" Fuck" Fuck" and her hips were rising off the bed as her fingers were vigorously attacking her clit.
As I watched, she went rigid then gradually sank back down on the bed. She was still slowly circling her clit with her fingers and shuddering every now and then.
I was getting hard again just watching her. It was very erotic. When she opened her eyes and noticed I was getting hard again, she laughed and said she had to go.
I tried to get her number and told her I would love a repeat performance, but she said it was just a bucket list thing.
I put "Stiffy" away and we cleaned up and she gave me a quick hug before shooing me out the door.
I kept checking Craigs list but never saw her again.