I grew up in Phoenix. We had outdoor, 3 wall racquetball courts in all the parks which my brothers and I used to play at all the time.
Once, we were playing and I hit the ball over. Went to retrieve it and an "old" guy was standing just around the corner just going to town. It took me a minute to realize what I was seeing, but then realized he was probably getting off watching my brother and I in nothing but our shorts playing racquetball.
I was freaked out at first, but later thought it was kinda hot that he would be stroking over us.

A much older guy

The pupil at secondary school who introduced me to wanking

Frotted with other boy's experimenting when younger. But an actual stroke show happened with a female family friend while she jilled. Posted the story in a few threads here. If interested in reading the story it can be found in my profile as I care not to copy and paste it again. And I think it was one of my best orgasms ever. (Edit) I have witnessed and joined in on much masturbation over the years. But that was simply the best.

I grew up in ireland. Porn ws illegal. But I got some mags from England. My friend found them by accident when we were 16. There was an immediate Emergency build up of sexual tension. I was surprised by the fact that I was turned on by how turned on he was. Hard for people to imagine here, but at 16, these were the first time he saw images of pussy. He didn't know what to do.

I decided to help him out And dropped my own pants and started to masturbate. I have never seen such a look of happiness and relief on anyone's face.

We became 100% reliable jack off buds after that. If alone, we're would cum. Porn. Or no porn. No exceptions, until I left the country. I met him for the first time in 25 years a few months ago, but he was with his wife.

I was rock hard the whole time. I miss having a bud

I grew up in ireland. Porn ws illegal. But I got some mags from England. My friend found them by accident when we were 16. There was an immediate Emergency build up of sexual tension. I was surprised by the fact that I was turned on by how turned on he was. Hard for people to imagine here, but at 16, these were the first time he saw images of pussy. He didn't know what to do.

I decided to help him out And dropped my own pants and started to masturbate. I have never seen such a look of happiness and relief on anyone's face.

We became 100% reliable jack off buds after that. If alone, we're would cum. Porn. Or no porn. No exceptions, until I left the country. I met him for the first time in 25 years a few months ago, but he was with his wife.

I was rock hard the whole time. I miss having a bud

My mum's best friend.... I had the blinds shut and was wanting to an old skool clothing catalogue. Parents were away so I thought I would have a lunchtime tug in the kitchen. I didn't know that a plant pot was holding a blind open and as I wanking i suddenly see a face peering at me. She was furious and gave me a lecture about having no respect and claimed she watchhed the whole thing. She wasn't fit, very irritating so no follow up wanks.

Later in life I'm sure the mother in law knew I wanked to her sunbathing, that's in another thread on hear somewhere.

It was the School Captain at School.

First person I ever saw was the girl who lived behind us. We were very young, maybe 11 or so. She showed me her pussy and rubbed it saying it feels good when I rub myself like this. Me being at such a young age did not know what to do but I liked watching her do it. She did it a couple of more times for me and then my family moved out of state. I want to say this was probably third or fourth grade. Looking back I am wondering if she was sexually abused. But you never know she could have also explored on her own.

I looked her up online a few years ago (and the last time I saw her was probably 1980). She never married and had the same name. Has had a very tough life and it does not look like things have gone her way.

But anyway that is the first person I saw masturbate in person and even though we were the same age I did not understand what she was doing other than I liked to watch her and she would do it for me without me asking her to do it. I think she did it 3 or 4 times for me during that summer.

Old guy I used to visit to watch porn with. I'd be 16/17yo at the time

I was 11 he was 12. We were having daily conversations about sex, I had a lot of questions. I was not jacking off yet, did not know what that was. I said something about what I thought sperm was, he told me that was wrong and he would show. We went to a place he sat down, open up his pants and pulled his cock and started stroking. I remember being a little put off, not watching the whole time, then he told me to watch and as I did he squirted his load.

Free happy childhood. Me and some neighbour boys strolled around in the fields and bushes around our houses even before school age. So the question came up necessarily. I cannot remember the first time. But something like pull our trousers down or even show our pissers. This was the name of them.
A mystery is that I and most of them were already able to do it that age. There could have been some teacher amomg them. Very unusual. I had discovered it by myself very early.
Usually we stood in a circle trousers down. Some dirty talk and dirty laughters and then the pumping started without any more word. But everyone by himself only.

My sister. I was around 11 or 12 and she was a year younger. She didn't realize that her bedroom door wasn't fully closed. She was fully clothed but it was still the hottest thing I'd ever seen.

She was lying face down on the bed with one hand underneath between her legs and her ass was humping away rubbing her pussy against her hand. I watched as her pace and intensity increased. The movement of her body, the expression on her face and her whimpers and gasps and moans were so hot, I still vividly remember them.

But the hottest was when she began humping frantically and grunting until her legs stretched straight out and her whole body stiffened. Her body started shuddering and she was gasping and moaning until her body relaxed and she let out a sigh of relief. It was obvious that she'd just had an incredibly intense orgasm and it seemed like this was far from the first time she'd done it. Unfortunately, I never got to peek in on her doing it again.

I was 15 and my best friend was 16. We were watching a porn movie and after much affirmation that "we aren't gay" we got naked and started jacking off. Soon we weren't watching the movie, we were watching each other. That led to us stroking each other and eventually to sucking.

edited