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!