I was wondering what some of our members boldest or riskiest masturbation sessions where? Here's one of mine

When I was a teen our family and my Hot aunt's were all camping together. We were at the beach when my Aunt asked me if I could
Go to her trailer and grab her sunglasses. Seeing her in a bathing suit had me horny as fuck. Once I got into the trailer, I grabbed some tissue, layed down on her bed, pulled my trunks down and went to town. The windows were open but only someone right at the trailer looking on could see me so I felt I was safe enough.

Only took a few minutes before I shot all over myself. Cleaned up, grabbed the sunglasses and as I walked out, my aunt was standing right outside door!

I muttered "sorry" and handed her the sunglasses. She just looked at me with a say grin and said "it's ok, I was just waiting for you to finish"

How long she watched? No idea. We never spoke of it and I spent much of my youth jerking of imagining she watched the whole time and liked it.

Now, I got caught but what's your boldest move you got away with (or got caught as well)

I enjoy driving around and jacking off. On one occasion I cut through a mall parking lot, as I was waiting to turn a group of teen girls walked right by me, I had my window down, arm on the door, I could have easily touched them they were so close. So fucking hot as I made eye contact with them while stroking my cock and shooting my cum.

Another I had was a legal age family member and I were watching a movie together and she fell asleep on couch next to me. Tight colored wife beater shirt on, tits bulging out so I put a blanket over my lap, snuck my cock through my Pajamas and slowly and quietly jerked off.

I grabbed a paper towel after a bit and came into it while she slept within a hands reach. At least this time I didn't get caught!

After returning on a bumpy flight from Vietnam to LAX, I needed to relieve the tension so I went into a busy restroom in full military uniform found an empty stall dropped my trousers and had a pleasurable jerk off session before catching a connecting flight to my destination.

Sitting in my car in a parking lot ogling two HOT young (legal) girls talking outside their car parked across from me.

Getting super stoned with a mate, exploring an old abandoned mill and ending up cocks out with porn blasting on our phones. The obligatory weirdo appeared not log after we shot our loads over an old table so no idea if we got caught or not.

My gf jerked me off in the bed of a pick up truck while her dad was taking us fishing

I'd have girlfriends who jacked me in the back seat of their parent's car with their parents in the car.
The psycho I went with in high school demanded I learn to jack off. Cause I never had. Sometimes she'd suck my cock and abruptly stop telling me I had to jerk off. On a few occasions she let one of her sisters watch. And on 4-5 occasions sister was allowed to touch to see how hard my cock got. Yes they watched as my cock spurt for them.
I was fucking the witch one night when she let it slip her sister said my cum was thick and creamy. She almost got pregnant that night.

Wife's friend skyped her but she was in the shower so I answered......got to stroke for 10 or 15 minutes chatting with her and watching her get dinner.....making sure my cam stayed above waist level.....lol.

i once stroked under a pillow in the livingroom watching tv with my parents

Used to blow a load in the hot tub in the gym. Position myself so the jets moved my cock, then sit back and let the cum fly into my shorts. Three people sat in there when I did it one time.

Before my ex-wife and I were married, we had taken a weekend trip to see her sister in a nearby town and then to my aunts house a few hours away.
While at her sisters we got to sleep together on the living room couch, but no privacy, so we really didn't get to do much more than grope each other a bit.
At my aunts house we had to sleep in separate rooms because my aunt is super religious and would not allow us to share a bed in her house since we were not yet married.
Needless to say, by the time the visits were over we were really horny and could not wait to fuck, suck, masturbate or something. So on the way back home, we stopped off behind a shopping center in the town where her sister lived, got in the back seat and I put a condom on and we started fucking and it was really hot until a car came around the corner and approached us really slow, went past, turned around and slowly went by us again then sped off back around the corner from where they came from. I told her it was not very cool and that we should leave. She thought it would be fine since they had left, but I wanted to leave. we both jumped back into the front seat, I zipped up my pants with the condom still on and then a cop car came around the corner and stopped to talk to us. He asked to see ID, where we were from, where we were going and why we were behind the shopping center. We told him we just wanted a quiet place to talk about some things. He said that was cool, but we probably want to find a different spot to talk (smiling like he knew we were fucking, but he was being very nice and friendly) He explained there had been some of the stores in the shopping center broken into so it was being watched really close. Told us to be safe getting home and have a great night.
Not sure if he would have arrested us had he caught us in the act, but yeah, he knew. lol
The whole thing made us both even hornier. She was driving and when we got back on the road she told me to pull my dick out. SO I opened my pants and pulled my cock out. Still hard and still with the condom on. She laughed because she didn't know that I still had it on. She expressed how frustrated she was because we had just gotten started and it was feeling so good (which was kind of rare because of a medical condition she had usually made insertion painful for her) So she said she didn't think it was a good idea to stop somewhere else and risk getting caught again, but she had to enjoy how awesome it was feeling and get off and could not wait until we got home so she opened up her jeans and slid one hand in while keeping the other on the steering wheel and told me she wanted to see me jack off and then she was going to ride my cock and suck me off as soon as we got in the door the very minute we got back home.
I jacked off with the condom still on and shot inside of it and she came a few minutes after I did. Watching her getting off while driving got me immediately hard again and I had to jack off one more time. This time without the condom. This time, when I came, I shot in my hand and smeared it back on my cock so that my cock was covered in a thick layer of my cum just as we were pulling in the driveway. Then she leaned over and licked and sucked my cock clean as we sat in the driveway. She pulled her hand out of her jeans and put her pussy soaked fingers in my mouth.
Just as she promised, as soon as we got in the door, she fucked me on the living room floor, riding my cock until she had a few orgasms and when she was done she hopped off and sucked me until I exploded in her mouth.
Later that night she woke me up with a surprise blow job until I came in her mouth again. I was about to return the favor, but she said no. She just wanted to thank me for earlier that night and that I should just relax and get some sleep. Then she woke me up with another surprise blowjob the next morning and after sucking me stiff, she got on top of me in a 69 which must have lasted well over an hour until she turned around as if she were riding my cock again only my cock was not inside of her. She was rubbing and grinding her wet pussy and clit against my hard cock until she came and then she rolled onto her back and said to me "Do it on my face!" so I got up on my hands and knees over top of her with my cock in my hand over her face jacking off until I shot my load all over her face then shoved it in her mouth again for a few more strokes in her mouth.

Back when I was a teen, I snuck off during a camping trip into the forest, pulled my shorts down and had a nice jerk off session.

At first I kept looking around, making sure I wouldn't get caught, as I got closer though, I just closed my eyes and really got into it. Right as I was cumming I heard some giggles and rustling in the woods. I never saw anyone though, so it could have just been some girls walking and joking within earshot but I like to think I was watched by some college girls as they hiked though the forest.

While visiting a friend...we were watching porn and having a beer. When he went to the bathroom to relieve himself, I whipped out my cock and started jerking off. He was pretty shocked when he came back into the room but just watched me and never said anything until I finished, then he smiled and made a comment about making sure to clean up my mess. All this while his wife slept in the next room with the bedroom door open.

also visiting a friend. he had gone to work that day and came home to see me stroking my cock on his couch to the porn i had brought w/ me... "holy shit bud that is a fucking horse cock". i said thanks, he left me to it and I kept stroking.

next day, i found one of his dirty mags in the bathroom that he had just come out of. fun times.