I haven’t in my adult life (only as a kid), and it was only with 2 other guys (on separate occasions), so technically not a proper “circle jerk”, only a “mutual j/o”. I’d like to though…
I’d like to have one where you’re not jerking yourself, the person next to you is. So a circle of jerking off your neighbor.
As a early teen my friend and I did. He was far more mature and very much more endowed than I was. He loved playing with my little dick and I had super powers when I stroked his monster cock. I think some of our other friends were involved in group sessions while him and I hid the fact we ever went there. I think if the opportunity was presented I’d go there again.
It has been about 7 years. My buddy who lived next store would meet me on his porch late night. A few times, he brought one or two of his friends. It was a ton of fun. my buddy had a super thick beefy cock. One of his friends blew in under two minutes his first time. My then wife joined us twice. She did not care that we did. my buddy loved watching her rub herself out. I always wore my then wife panties. my buddy knew and he wore them also. I gave him a pair once. Nothing like walking back to my house through the yard with a load in my panties.
I haven't as an adult. When I was very young I was invited into a small club of neighbourhood kids. They had made a clubhouse out of a large overturned car, with the entire interior removed, It was in a lot behind the area we lived in. I believe it was a wrecking yard and this one was beside a fence that we could crawl into.They had big flash lights, for lighting, and some gathered cushions and blankets to sit on. The group was a couple girls, and three other boys, I was the youngest. I remember being quite excited, to be invited in, as they were a few grades older than me. First time there, I noticed the smell was of old car, mildew, and something I could not put my finger on. It wasn't long until one of the boys opened up a box and brought out a mix of sex magazines. Playboy, Penhouse, and best of all, some foreign magazines with hardcore sex. Everyone was looking at the magazines, when one of the boys unzipped his shorts and pulled them down. The other two soon followed. They all pulled out their cocks and started stroking as the girls watched. I was shocked but intrigued. They encouraged me to join in. Considering I had done it before with friend, (He was the one that introduced me into masturbation) I dropped my pants and joined them. The two girls sat there giggling and watching us stroke as a group. The girls would lean over us, watching each of our cocks, as our hands moved up and down. Soon the stroking became more intense. One at a time the guys reached orgasm and cum started to flow. I was too young to have produced any cum, but it was then that I figured out that other smell in the club house. We had many meetings. Not always the whole group. Every opportunity I had, I would try and get someone to come with me to the club house. If no one was available I would go on my own. There was no club name, but in my mind it was The Neighborhood Cum Club.
As mentioned before we did this with a volunteer girl as a “live target”. She kept her panties on but that was the target. There were quite a few of us so they were saturated at the end. As with other games of this type there was a penalty for being last. In this case having your face pushed into her panties. We did another one called “hit the biscuit” but with without a girl.
Back in the day, our attempts to pull off a circle jerk usually turned into furious cocksucking. I think we tried to do this like three or four times and just failed to do it. Hard to jerk off when the guy sitting next to you rips your hand away and starts sucking your dick, wouldn't you agree?
I agree KDaddy23, the only circle jerks that remained circle jerks were many years ago. These days it’s me giving blowjobs
Oddly, I've only done one circle jerk as an adult and... it quickly devolved into a suck-fest and it was my fault that it did. I was pulling on the guy's dick on my left and something in my head said, "Fuck this hand job shit!" and I went down on him and without even thinking if he was down like that. The guy on my right stopped playing with my dick and went down on me and it turned into one hell of an afternoon of cocksucking. I thitnk that before it broke up, I had sucked off ever guy who was there - seven other guys not counting myself. The eight of us got together one other time at another guy's place and we went straight to sucking dick and it was very much like one guy said: "I can jerk myself off!"