I live in a condo and always leave the shades open when I masturbate. The couch is right next to the windows, so I'm sure the neighbouring units would have no trouble seeing in. Not sure if anyone ever has, but it's a turn on to think that I'm being watched.

Different story when you're a teenager though. I was maybe 13 or 14 and at my grandmas house with my family. She had this inflatable manequin from work. It wasn't the sexual inflatable doll (I can remember that it was actually a male doll) but it had this hole in the right location.

So I'm all by myself in the back room, and get the bright idea to fuck the doll. I'm on top of it with my pants halfway off when my mom walks in.

She's furious, and I mumbled something to the effect that I was just trying on the doll's belt. I guess she must have gone straight back and told everyone what I was doing, because when I got upstairs my grandma was saying that maybe I just needed a belt to wear.