This is my first story posted here. hope you enjoy it as it's all true and as accurate as I can be. Comments are very welcome, even if it's just a quick one. Thanks!!!
I live in a condominium in a middle-upper class suburb. I'll explain the layout, since it's relevant. The arrangement of these condos is U-shaped, which puts me at the bottom right of it. So, if I look out my front door, I see a sideview of the frontdoor of the condo perpendicular to me. And, if you looked at my front doorway, through the second outside glass door, you'd be looking down a short hallway and into the living room, with a tv against the wall to the left.
At this time, a couple and their kids was living in the condo perpendicular. I was only in my mid-twenties, but the mom turned me on, probably in her early 40's, not incredibly hot, but attractive in a tomboyish way. A great body, shoulder length brown hair, but just not the type to be made up often.
There are always others milf's around here and I had often wondered how they'd react catching a glimpse of a younger guy masturbating through a window or just walking around naked, especially considering the attitude of the area being socially conservative. The truth, I think, is that everybody around here loves sex and kink, whether they could ever admit it or not. In fact, in general I think that's true but social conformity causes them to put on appearances. Anyway, who knows what goes on behind closed doors with the 'well-to-do'.
So, on a day off from work, it was mid-morning and I was feeling damn horny. I had seen my neighbor leave earlier while I was walking around downstairs and glanced outside. Then it occurred to me that she had a routine and usually came back soon after. I decided I wanted to get 'caught'.
What I did was open the front door, put a good porno in the vcr, and sat with my feet under me on the floor of the living room. I sat far back enough to where I couldn't look to my left and see the front door at all. But I knew that if someone were to look through the front door, they'd see my hand stroking my cock.
The plan I had was to not lean forward to see if she had come back and/or was watching me at all. The only thing I planned was afterwards, to see if her car was parked outside. Then, I could only wonder if she looked over and saw me jacking off or not. I thought the mystery of not knowing for sure would make it unique.
I began stroking and was in no time ready to come because of the risk of perhaps being seen. I cupped my balls and massaged them, wanting every drop of cum I had to shoot far if she happened to see. But I realized that rather than having a huge mess on the carpet, I'd have to cum in my hand, which she wouldn't be able to see.
Quickly, I ran to the kitchen and grabbed a large, serving plate. This way I could just aim at the plate and let it shoot all over. After getting the plate, I took a quick glance out the front window and sure enough, saw her car pulling in the entrance. I figured I had no more than a minute or so before she was at her front door. So much for not knowing, but that warm feeling came over me entirely, knowing I'd be 'caught'.
I got situated again in the same spot, laid the plate down in front of me, this time standing on my knees and scooting forward a little to make sure she'd see my entire cock and balls. I remember that I had the big window to my right open, which from her point of view, was behind me, so she should be able to see everything well.
I started jerking again furiously. Faster and faster I stroked my cock, trying to time it just right. I glanced around the corner out the door. She wasn't there and in that moment I wondered if she had just gone in without noticing at all.
I got to the point of no return and felt a very intense orgasm begin. I aimed my cock at the plate and large streams of cum splattered all over it. My body convulsed a lot and I lurched forward. I caught myself with my left hand, my head hanging down as I kept milking all my cum out. As my orgasm subsided and my hand slowed down, I looked to my left...
I felt like I was dreaming, cause she was right there, standing and holding her outside front door open, looking right at me. I was still slowly milking my cock as we stared at each other, as if waiting for one of us to make a move or something. Then she smiled, followed by a friendly wave. It wasn't anything more than an everyday 'hello', really. I just smiled back and laughed a little to myself because of the causal way she acknowledged what had happened. Then, she went about her business of unlocking her door and going inside.
Of course, I wasn't sure how much she'd seen, but she sure seemed to have been waiting for me to come. And she did!
She and her family moved a few months later. But until then, every time I saw her, whether it was passing in cars or whatever, if she was with her family, she didn't look my way at all. But if she was alone, she would glance over and smile.
To this day, I can't help but wonder if she masturbated while thinking about seeing me that time.