Where is the riskiest place you have masturbated?

in the woods and in my van on lunch breaks

 

Work bathroom and at a big family event at someone's house (lots of people, door open). I don't think I have ever masturbated outdoors. Sex is another story.

 

A rest area on I-80, I stopped to take a leak. There was only one other car, nobody in the car. I walked into the restroom and there was a guy, pants around his ankles, fully erect stroking it pretty fast.

he said sorry and turned away. I said, don’t be sorry I was thinking about doing the same.
He turned back around and kept stroking, slower though. I guess he wanted to wait for me. When I finished taking a leak I washed my hands then, pulled my cock out and we jerked off in front of each other.

 

I did it in class. Just rubbed my penis super slowly on the outside of my jeans under the desk and came into my underwear/jeans. Am I proud of every place and circumstance under which I've masturbated? Of course not. I have some less than glorious moments in my past. But... men of a certain age are not well known for their self control. I sure ain't excusing it. Absolutely not! I'm just saying, if you have a son or a brother who's just started masturbating, get... fuckin'... ready, 'cause you're gonna see some shit. I know it's not the most delightful thing to be brushing your teeth and find some conspicuous white gunk stuck around the side of the drain. Or walk into the living room to see him covered with a blanket even though it's August and one arm is not on the side of the blanket you'd like it to be... But, he's not necessarily doing it "to you." Or getting off on it being seen. He's just figuring shit out. I assure you, he's probably not any happier than you are that he needs to do it everywhere all the time. EVERYWHERE. All... The... God... Damn... Time...

 

There has been a few places…hard to say which was the riskiest.

In college I was alone in a in town student lounge. There was a magazine left behind that had nude men and women. In that era, most magazines showed tits but no bush. This magazine showed bush and hard ducks!
OMG!!
In a flash my cock was in my hands as I stared at bush, tits and cocks. It didn’t take long to cum. Almost immediately after shooting my load, I heard someone’s hand on the door handle to the lounge. I shoved my cum covered dick into my pants, pushed the mag aside. There was no time to zip. I put stuff in front of me and left. The gal who almost caught me mid act was someone I was acquainted with but didn’t know very well. It’s amazing to me today that I was so horny as to jackoff and cum in a public area….the door being closed (but unlocked) is all that saved me from being seen as I came.
I still wonder what would’ve happened if she had seen me jacking off. Stand and enjoy the view? Help out? Run and call campus police?

 

I'd bet good money she would have just quickly shut the door and never mentioned it. I do find your story interesting because at my parents house, I was allowed to masturbate pretty much everywhere and they never bugged me about it. But when I got to college, from day one, I felt utterly flustered about how I would masturbate in a single shared room with a bathroom that didn't lock and was shared with two guys in the connected room next door. And I just couldn't think of anything to do but tell myself, "Well, there goes that!" Then, after that first year, even though I moved into more private dorm rooms and eventually an apartment with my own bedroom, I'd just stopped caring. I shit you not, in my first three years of college, I masturbated twice, three years apart. But I mention this because I'll never forget the thing that made me break that first time in my freshman year was seeing some fashion ad in a magazine in a friend's dorm room and asking if she was done with the magazine could I have it? I rushed back to my dorm room, made sure no one was in my room or the other connected room and rubbed one out to that ad as quick as I possibly could.

 

I jerk off alot while driving anywhere...schools...pools...mall parking lots fun and exciting

 

I have been thinking about a risky place, on the other hand I really don’t want to get arrested. You can’t even masturbate on the trail to the clothing optional beach, off the trail of course, even that is illegal.

 

Thats what makes it risky

 

I have taken a couple of my wife’s sport skirts and cut out the liner so it’s just a skirt now. I wear it while driving around town so I have easy access to my cock to stroke it .

 

Just a side comment….
OMG do I hate SKORTS!!
Skirts, especially short ones, always have made me think for easy it would be to pull down my wife’s panties and fuck her.
SKORTS are like a chastity belt!

skorts are to skirts as granny panties are to thongs!

sorry…I’ll find my beer and calm down