Now Viewing: What is the riskiest/weirdest place you've masturbated?
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A river bank with no cover and no people around. Eventually some assholes had to appear on the horizon. Didn't care staying long enough to find out who's seen whom first.
When I was 13 and had hit puberty hard. I would masturbate in my room while I had my friends in the room playing video games. I would pretend to watch them play while I was in bed, under the covers. I raised my knees up so while I masturbated the sheets wouldn't move. In my dumb ass 13 year old head I didn't think I would get caught and technically I didn't. Much later to rib me a little. One of those friends brings up they knew I masturbated when they were in the room, but the weird part is he didn't care. The other one never knew.
At the height of my puberty I once did it... right next to my mom. I thought she was sleeping and her back was turned to me, and I got aroused by a particularly sexual music video on TV. We were in a hotel on vacation, so I didn't have my own room. She wasn't sleeping and asked me what I was doing; I said I was just scratching an itch, but I felt awkard af.
In a classroom waiting for class to start about 5 years ago. I remembered reading through a thread similar to this one somewhere and figured "it'll be a while before anyone shows up, so eh why not". I think I actually did it a few times.
Jacking it in class during middle school was a VERY common habit. One of the benefits of being seated at the least seat in the back corner. Of course, that was when I barely even knew what it was and likely wouldn't have done so if I did.