This happened a few weeks ago.
So this isn't that dramatic, but it did actually happen. (Unlike some of these PHONEY but HOT stories!) But first, some background
My stepmom came into my life when I was a kid. As I hit puberty, I was DYING to have somebody look at and admire my fast-growing cock. While I was too weirded out to show my mom or dad, I found it was less taboo to find ways to exhibit myself to my step-mom. (She wasn't super hot or anything, but she has a pretty face and looked about 10 years younger than she is.)
For example, if I knew she was around, I would ask to use her shower ('It has a better spray'), which had a glass door. Then I would get myself half-hard and just slowly stroke for 20 minutes. Every so often, if I timed it right, she would eventually need to come in the bathroom to get on some makeup or brush her teeth, and then I'd pretend to be rinsing my hair and hope she'd look at my engorged cock (and hopefully think it was that big when soft all the time!)
This was OK, but she'd never give me a good long stare or anything. My first big coup, though, happened later, on a trip we took on a small boat. We all shared a room. I slept in the nude back then, and one morning, while my dad was in the shower, and my stepmom was combing her hair on a chair facing me, I sat up on the side of the bed with half-a-woody as if I was too groggy or casual to care that I was naked in front of her. In fact, I was EXTREMELY proud of my thick cock at that moment!
I think I was so bold at that moment, she reacted spontaneously. 'My god, Joseph, you have a huge cock!' She giggled.
I swear to god, I could have died and gone to heaven at that point. Really, that's all a lot of us exhibitionists want-for somebody to tell us we have a big cock (once a day).
Now, my dick is not 'huge.' But I was a skinny 14-year-old at the time, and it was already a solid 7', cut and quite handsome by all accounts since. I was so happy she had said that!
Unfortunately, I never was able to find another moment with her like that one. Perhaps she was more careful, thinking she was crossing a line.
These days, however, I again live near her-in the next door apartment. We share a backyard. She NEVER goes in it, though, nor does anybody else but my dog. Consequently, I have taken to masturbating in my living room despite the large plate windows and sliding-glass doors that face onto the large yard.
The other day, my sloppiness caught up with me. I was going at it pretty good, with my laptop porn next to me, when I saw something in the corner of my eye. It was her, of course, and she was looking in at me. I yelped!
Now I was both turned on and embarrassed. After all, the fantasy of being caught is not the same as having it happen. I yanked my pants back up and hunched into a ball on the couch to hide my stiffie because instead of turning and walking away, she had decided to come into my apartment!
She started talking to me about something about the building or bills. Did she not see me jacking off? Maybe the reflection on the glass made it hard to see in? Did she see me and think she should pretend she didn't?
I couldn't see straight. Being still horny, I wanted to pull down my pants and show her my cock, but I didn't have the guts.
She walked out and I went back to my whacking, now energized!
Since then, I have wanted to ask her if she saw me, so we could have a laugh about it-but if she didn't see me, I'll feel pretty stupid.
I even had my girlfriend go out in the yard and look in at me on the couch, at the same time of day. (I told her what had happened.) 'I can see you perfectly,' she laughed.
Of course, in my fantasy, if I ask my stepmom if she saw, she'll say yes and ask for an encore!