I'd have to say that my riskiest was while driving to work one day on a back road. Easy enough until that big O hits you, then it was a bit distracting. I wouldn't recommend it but everything worked out okay for me in the end. I've also masturbated outdoors many many times, especially while growing up in the middle of nowhere. I'd get buck naked in the woods, masturbate and just otherwise good around for hours on end. It was unlikely that anyone would find me, but it was possible, my siblings would occasionally go out into the woods. I think my next most risky experience was in my car in the parking garage at work. I did that several times, people would be walking by the car and I'd be going at it lol.
Fuck! See that’s how I grew up next to about 100 acres of woods. My friends and I would go into the woods to build forts etc. but when we got
Older we would start experimenting. One time I was out in the woods alone. I was about 15 and I started to jerk off, as one does at that age and alone
when this older guy who lived in the neighborhood was walking through the woods and must have seen me for at least a few minutes. He was watching from about 100 feet away when he suddenly said hey as I was about to cum. The, after ruining my orgasm, came down and we talked for a few minutes and then he started to grab at his cock through his pants. He asked me if I did that a lot out here and I said yeah. He then pulled his out and said “me too” and started to jerk his. Over the next few weekends we started to jerk with eachother and then move on to bj’s, until finally, and I was fucking ready for it, he wanted to fuck me and pulled lube out of his pocket. He said he wanted me to fuck him first and eat his ass. His ass tasted like he just got done using the bathroom but I didn’t care it was sweet in a way and he told me to clean his ass before I put my cock in. After I just used my spit and put my cock head into his well eaten ass. He fucking loved it and so did I. He told me not to cum though not until his cock was fucking my tight ass.
up to this point the largest thing I had put in my ass was a toy baseball bat that I got at a columbus clippers game. And his dick was at least twice the width. He at my ripe ass, I had gone to the bathroom before coming out to the woods, snd he licked up my dirty hole with pleasure as he jerked his dick and mine. After he had enough spit on my ass he fingered me to get me loose and then put a lot of lube on his cock.
This guys cock was massive compared to my 14 year old cock, even though I was above the national average at this point, I still felt small
Compared to what I had seen in porn or in my school locker room, he didn’t have a skinny or particularly muscular body but he was built and solid. I think he was a senior in high school in our school district around central Ohio; or corn country as I call it now that I live in the pacific north west. He had a musk to him that I will never forget and at one point made me smell his pits. I fuckin loved the taste of his huge cock, asshole, and pits.
he then put his lubed up rod into my ass and I almost screamed because it hurt so bad…at first. After he put it in he held it there. He told me he needed to piss and I, being as kinky as I was at 14 and loving to piss on myself told him just to piss in me! He did and that stretched and lubed me up enough that he was ably to fuck my now non virgin hole! We were maybe 20 yards away from the nearest house but fuck I didn’t care. He slammed my sloppy, wet, musky, dirty, pissy ass as hard as he could after working up to it! I was so horny I didn’t care how much it hurt or any consequences if we got caught! I was pulling on my 6 inch Cock at the same time and when I told him I was going to cum he flooded my ass hole again with his cum.
We decided to meet there everyday until he left for Ohio state university for their justice program and he became a cop
but fuck we met up at least once a month until I went to college. After that it was about once every 2 or 3 months. We would continue to fuck in the woods behind my house until I moved to the PNW. I need to go home soon though to visit. I haven’t been in 3 years and I’ve heard they are tearing down the woods to build luxury houses. Maybe we can still get away with fucking in someone’s back yard and not get arrested ( that’s a whole other story) hahah but that’s the riskiest place I’ve jerked and had sex as. Youngin. College was a different story as well