Where is the riskiest place you have masturbated?

In a motel hottub once. Came hard.

 

Toilets in the cinema, behind a skip in my back lane, in the garden as a teen where I could have been seen, woods, car driving along with a mate, class room in school when it was just me in there but I didn't cum, and college, public toilets.

I remember one occasion when me and a my friend were the only ones in the classroom the others had gone on a trip, and we hadn't wanted to go, we were tidying up the classroom, we got bored so we decided to have some fun, we sat facing each other got our cocks out and had a really great group wank, be both ended up squirting so much.

Another friend in the class one day pulled his cock out, and as he was stroking it decided to show it to the girl he fancied as he was wanking she was not amused.

 

I have a ton of stories about masturbation. I travelled around the Country for years and stayed a numerous hotels. I had some that I stayed at so much I could request which room. These hotels I requested a 2nd floor facing either the street, hotels across so I could watch for other voyeurs or exhibitionist. The other was some back parking lot for guys or couples who had sex in the car as they watched the nude show in the hotel.
My very riskiest was in Macy's Portland at the mall. I was in the women's lingerie dept and usually the clerks didn't bother me after I said I was looking for a gift for my wife. I'd intentionally pick up a few items so they thought I was serious. This one time I got in the slip, girdle section. The store had a few large hanging rows of women's slips half and full. I love the feel of nylon on my cock, so I was jerking off in a half slip and a teenage girl and her mom came and surprised me. I was as hard as a rock and ready to shoot when they were right nest to me. I held up a slip with my one hand and continued to cum as they talked and looked at slips. When I let go of the slip full of cum, I let my raincoat drop to hide my still hard cock. I slid the slip back where it was and walked away still horny like I wish they saw me and helped me cum. Didn't happen but someone certainly found a stuck together stiff slip.

 

In my sister's bed while she was downstairs. Also in the upstairs hallway while my whole family was downstairs for Thanksgiving. Also English class. Also the back seat of an Uber. Also the chair in the living room right next to my sister. Also the shower with two friends who did not give me permission to do that. Also the lobby of my old apartment building. Also the middle of Stuyvesant Avenue at 1 a.m. Also my parents bed while my dad was in the shower. Also my friend's shower stall in a bathroom with no locks while both her kids were home. Also my parents' backyard at 7 p.m. on a Tuesday. Also the park behind a middle school at 10 p.m. Also a train station 15 minutes before a train arrived. Also my friend's bedroom while he and his girlfriend were just a couple feet away from me. Also under a jacket in my friend's apartment living room while all our friends were sitting around me playing video games. Also hell. Also heaven. Also New York City in the 1970s. Also my own head. Also my parents' bed while my mom was lying next to me reading a book. Also my hand. Also space, where there is no atmosphere and the lack of pressure would tear apart every fiber in your body one sinew at a time. Also the White House.

 

So you re saying pretty much everywhere lol

 

Bingo!

 

Public restrooms for sure. Beach at night. Were a couple of my risky ones.

 

long road trip with family in van . I went to back that laid out to bed and slowly humped to release . Took nearly 2 hours .

 

Easier for women to sneak in an orgasm . Often wonder how many do and I’m none the wiser . Especially at movie theaters

 

You do get around.

 

More than the average bear bobo.

 

when i was in high school the girl in front of me sitting in here desk would hump her foot during class.It was cool till the teacher said to put both feet on the floor i know he knew what she was doing.

 

on a plane night flight from jamaica

 

About 20 years ago, I'd been living in Arizona, and things just hadn't worked out. I was getting ready to move back east, on the edge of bankruptcy thanks to a gambling problem.
I'd packed up a rented trailer and was on the way out of town when I stopped at a Scottsdale casino for a last fling at the gods of chance. I'd also wanted to say good-bye to a couple of blackjack dealers whom I'd befriended.

But especially Dani. I'd nearly fallen in love with her and I could tell she liked me quite a bit, but she was taken and, I wasn't going to wreck her life by putting a move on her.

And man, was she beautiful ... 5'10", perfect (to me) figure, ice-blue eyes auburn hair, and a sweet face said a man might die for.
Not surprisingly, Dani was and remains a member in good standing of my mental “spank bank".

As I played at her table for the last time, our conversation went from bittersweet to flirty to downright risque. Then she announced it was lunchtime. I walked her to her locker and we said our goodbyes, a little sadly, and hugged. In no time, I was as hard as a rock, and she noticed, showing me by grinding her hips lightly against my crotch area.

Dani said there was no way she could slip away today or she would take me into an empty lounge and have her way with me - her boyfriend was bringing her lunch - but, she suggested, one of the mens' bathrooms was closed for cleaning. While I was masturbating there, she would take care of herself in the neighboring stall.

Sounded like It might be fun.

Nope - as it turned out, it WAS a LOT of fun.

As I went into the mens' room, I grabbed a handful of paper towels and dropped a little hand soap into my palm. I sat down in the end stall, and started massaging the head of my dick in a slow circular motion at first, then back and forth along the length of my shaft. I closed my eyes and could see Dani's beaufiful face and pursed lips. I heard her moan, and knowing she was pleasing herself a short distance away added immeasurably to my pleasure, and she admitted to me later that it took her up a couple of notches to know what I was doing.
Suddenly…

…. I felt my cock swell and pulsate, and I moaned Dani's name and blasted at least half a dozen jets of cum into my paper towels.
"Oh, Dani...aaahh". My head swam and I nearly fainted.

I put myself together and walked out the door.

On the way I saw Dani emerge from the next stall. With tears in her eyes, and in mine, we waved goodbye for the last time in our lives.

And incidentally, I haven't gambled on anything more than a six-dollar lottery ticket since that day.

But I do masturbate to her memory an awful lot so, if you'll excuse me, I have some sentimental stroking to do...

 

Out on our deck one summer afternoon as the neighbors 19-year-old daughter was topless in their hot tub. She clearly saw what I was doing as she was purposely showing off her gorgeous tits. As I stood and shot my load through the rungs of the deck she clapped, then walked into the house. Neither of us ever spoke of it.

 

Last night in a parking ramp, as I was exiting, I noticed a car x few spots away, bouncing away, clearly I have found a good public spot for sexual activities. Gonna make this a regular stop, who knows what I might see next time

 

I used to jerk off under my desk at my office after hours. Was always alone but risky because the cleaning lady would arrive and if I didn't hear the door chime I was definitely at risk of being caught but my cock was under the desk so wouldn't have been terrible. I would also keep stroking while she was there working...can't tell you how many times she came into my office for the trash and we made small talk while I was hard and exposed under the desk.

We had porn mags in the bathroom so she obviously wasn't offended. In hindsight, I should've let her catch me. Who knows, maybe she knew...

 

Maybe she would help lol

 

I remember times doing so at a local public park. With blanket and lounge chair in hand I would walk out in this big open field in the summer to enjoy suntanning nude. Well, within 10 minutes my cock was raging hard, so I'd begin stroking myself and blew my load all over my stomach. I'm really surprised I was never caught as many cars drove past about 200 feet away, who knows maybe they did see what I was doing.

 

I don't know how risky it was, but this morning I had to drive into town early for a grocery pickup. I was only wearing sweatpants and a t-shirt. I had been playing with myself on the drive in, so I made the pickup and heading back home I stopped to look at one of those metal framed carports. While I was looking around I walked into one of the shops that they had on display and decided this would be a good place to rub one off. The sun was just coming up, so i got in the back of the building, that does not have any doors on it, but it was dark where I was. I pulled off my pants and started fingering my ass and jerking off while watching to cars go by on the hiway. Left a nice load on the ground and went home.