I grew up in a home with three older sisters. When my cousin Jay showed me how to jerk off (in the shower at age 10) I was hooked immediately. Maybe because we did it togehter the first time, maybe because I was so sexed and lived with three girls, I don't know...but I soon started strokin' it in bed with the door open a bit, hoping one of my sisters would see me. (There's something REALLY HOT about secretly jackin' off in public and hoping to be seen and wanting to be secretive at the same time....)
Anyway, it was many years of fantasy jackin'-with Awesome Orgams I might add-I used to shoot three, four feet maybe if I didn't try to catch it with a tissue-before someone actually SAW me. I lived in NYC as a teenager and I got hot thinking about seeing other people having sex too. Voila, voyeurism was born.... I would go to Central Park at night and cruise the perifery on Central Park West looking into the apartments across the street hoping to see a nude woman or a guy jackin' too. I'd find a spot in the shrubs that was hidden from plain sight, that had ehough light from a neighboring streetlamp so someone could see me if they were looking closely. I got soooo hard and hot while scanning the windows for someone looking out into the park, hoping that they'd notice something unusual going on outside. Of course, they never did and I had a mixture of fear of being 'caught' and excitement over being discovered all the while. I always came with gushing euphoria on those hot and steamy summer nights.
I had to figure out a way to get my dream to come true though. It was fun, exciting, daring and hot, but I was always left with a little disappointment and hope for the next time.... And then it occurred to me; why not try this from home?? That would be even more daring-someone might actually figure out who I was! Then the mystery of attracting someone to watch me with interest and personal excitement was mixed with the fear of someone seeing me and not being pleased. How could I safely carry this off? Could I expose myself-show off my amazing, pulsating, glistening, oiled-up penis in mid-stroke-and hide at the same time in front of my bedroom or livingroom window? Could I find someone to see me and somehow determine if they were curious, interested, turned on or outraged without openly jerking off in an uncovered window? What an interesting and perplexing dilemma!
Well, after a few months of careful observation of the courtyards surrounding my back window, I did find an interested party. She was fairly young, in her twenties or thirties I suppose, and her bedroom window was no more than fifty feet from mine, one storey higher in the next building. We both had drapes in the window so we could hide or not as the situation dictated. Sometimes, I'd just meander in my room and jack off with the blinds drawn just enough to see in and out through a sliver, sometimes I'd pull the blinds open a bit more. That way, if and when there was someone watching, they wouldn't REALLY know if I knew they could see me or not. Until the day that I saw her watching me and our eyes met!! OH, MY, GOD!!! She was naked too and she was pulling the same see-me-don't-see-me routine as I was!!! Holy crap-all bets were off and I sprayed my jizz all over the place instantly. Wow-what a thrill. What an indescribable, ecstatic, extraordinary moment. Such a long time in the offing. So long-awaited, anticipated and all at once joyful, exuberant, extraordinary moment. She, meanwhile, need a few more minutes until she exploded and collapsed out of view completely, so I was able to play into her fantasy by hiding and watching and letting her see me and know that I saw her as well. When she resurfaced, slowly, timidly peering out from the draperies, she broke into one of the most delightful and genuine smiles I can ever remember or have ever seen since perhaps.
Both of us were somewhat shy and cautious in the months to come, but that scene was repeated with delicious regularity over the next year or so, and then she was gone. We did see each other on the street one time. She was waiting for a bus and I was just getting out of a taxi across the street. As I crossed towards her (and my apartment) our eyes met. She locked her gaze on me for a few seconds and we were frozen in a moment of suspension that seemed to last much longer, until a car blared its horn at me while almost running me down then and there. When I looked up she was walking down the block, away from me and never looked back. I chose not to go after her. She must have moved out soon thereafter because I never saw her again-at least not in person. She has been in numerous dreams for many years and-needless to say-many masturbation sessions to my delight, anticipation, enjoyment and fun over the years as well.