To make it really challenging, you can do it a really nice, quiet restaurant. One time, my boyfriend had to talk to the waiter when he was about to come, and nobody around us had a clue what was going on. He kept it together. I was impressed! He thanked me afterwards, and then said he was going to get revenge on me later. I told him I understood.
Regarding the other similar thread -- what's the differences between the "craziest" place and the "weirdest" place?
Gives a whole new meaning to "self-service". Like one of the first posters to this thread, I've also done it in a high school classroom during class. It was one of those "movie" days where the lights were off and I was sitting in the back of the room. I've done public restrooms a few times, and once I just pulled my car behind some buildings late at night and jerked into the grass. I couldn't help myself, I would have exploded otherwise.
At my grandparents place a while back, well it was more of a hand job (horrible) from a girl round my age living near my grandma at the time.
backpacked out in the tetons.. waited to be totally secluded on top of a beautiful panorama of the world.. will never forget it
I remember when I was a kid & it was still a very new thing to me I would masturbate wherever & whenever I could. One particular one I recall was when on a rope swing, hanging from a tree. The swing was in the form of a Bosun's Chair (i.e. a stick tied to the end of the rope, sitting on the stick, with legs either side of the rope). I would get stroking along with the rhythm of the swing, and then when I came I would spray all over the place. Sometimes there would be several of us competing to see who could cover the widest area - we had actually been playing this version of the game even before we learned about masturbation, but by seeing who could pee the furthest from the swing - basically a variation of seeing who could pee the highest up the wall (a game which I imagine 99% of boys have played at some time or another).
Weirdest for me was late one night on hols in Portugal whilst drunk. The heat always makes me very horny and I couldnt sleep. Anyway it had been a few days since I got off and I had a raging hard-on, so I decided to sneak out to the patio area of the house we were staying in - where it was cooler and nobody could see me.. The outdoors was soo exciting. By the time I stripped off I could barely contain myself & the cold tiles against my body sent me right to the edge. A few minutes of lying on my back & fingering my a$$ had me cumming buckets
Just got back from the supermarket. Late night shopping. Went in with just trainers tracksuit sottoms and tee shirt. Took a couple of pairs of jeans into cubicle (they are unisex). Got naked and jacked off while people were next door. I heard at least three women go into the cubilces next to me. Seperated only by a thin wooden panel.
Riding a horse naked, one-handed in the rain. Like riding on a bar of soap. I got very wet but it was a fantastic, genuinely enjoyable and unique experience. Just glad I learnt to ride a horse like that when I was very young and keep my balance at the same time, LOL!!!
Waiting for a flight at Chicago O' Hare in a stall in the restroom between Concoarses E and F. It was a Monday, about 8 am, so the area was quite busy. Don't really know why I did it.... just really horny I guess.
I masturbated on the balcony of a hotel, while my wife watched, and did it, too. I could go for another round of that.
The craziest place was probably when I was 14. It was also one of the most exposed and risky experiences I've had, pretty amazing as well. I hadn't masturbated in about a week so I was a pretty horny hormone-driven teenager lying in bed at one in the morning with a raging hard-on. I lived in a bungalow with my parents, and my bedroom was just behind the front garden, so a thought came to me. I looked out the window to see that there were only a few houses with lights still on, one opposite my house and another a fair way down the road. (You can probably see where this is going. ) I opened my window and, while only wearing a pair a briefs, climbed out into the garden. I bulled down my briefs so I was fully exposed and just stood there with a throbbing hard-on in the front garden. I walked to the pavement, lay down on the cold hard floor, after having a quick look around, I just grabbed my penis and jerked off for about 5 minutes, resulting in a crazy orgasm all over my body in the middle of the street, then, at probably the most awkward moment during orgasm, was when a car decided to drive itself rather slowly down the road, and the person just either completely ignored the naked teenager masturbating or didn't see me anyway. I climbed back into the window and cleaned myself up with a big *woah* expression on my face. That was pretty fun, and after that I started jerking off in (less risky) public places, just the thought of getting caught again really turned me on. Edit - Oh, and I'm new here. Hello.