I've jerked more to this memory than anything else that has ever happened to me. It was very hot then and it still is.
When I was finishing high school we had a cleaning lady that came in once a week because my mom worked a ton of hours & my dad was never home. One day I was off school for exams & I met the cleaning lady. She was not from a business but worked on her own for $40 cash my mom left on the table each Thursday. She was maybe 30 & smokin' hot. I was drawn in by her friendly flirting way & I'm sure she knew she turned me on my strutting around the house that day. She didn't wear the typical work clothes most maids would wear. In the house she wore a t-shirt & shorts with bare feet. She took every opportunity she could to bend over & show me her tight round ass.
I thought she was the hottest older chick ever at the time. After she left I went upstairs thinking about her while stroking my Vaseline coated cock for about 45 minutes. I had learned by my own discovery how to bring my cock to the edge of cuming then stop stroking & let my pulsing cock cool down to where I could stroke it again until the next feeling of orgasm came along.
Back then I could go for hours if I wanted to. I was very well practiced by that time. After a long stroking session like that I'd cum so hard I thought my balls would turn inside out when I blew. Did it feel good to make it last or what! The orgasms were very intense!
Once I saw her I could not get her out of my mind. Two weeks passed & all I could think about was that hottie in my bedroom half naked walking around where I stroked my cock all the time. I decided to think up a plan that would allow her to see me naked, then it grew into a plan for her to see me jerking off. It was the only thing I thought about until I made it happen.
I knew what time she arrived so I came back home from school faking a headache the following Thursday. I got home a half hour before she was to arrive then went upstairs to my room to get ready for my sneaky dirty plan. I stripped off then went to my parents room to watch for her car. I waited, slowly working my foreskin up & down over my hard cock waiting for her to arrive. I soon saw her car slowing at out house & as she turned in the drive I headed for my bedroom.
I put my headphones on without any sound, then laid on my bed. I left the door just open enough so she would see me as she came up the stairs. My heart was beating so fast & hard, that I thought I was going to pass out but I could not let this go. I was going to do it. I heard the door & as she came inside she shouted 'anybody home'. I was hoping she would start off in my parents room & work her way back like last time. She had to go right past my door at the top of the stairs if she did. My cock was hard & ready & I began to tremble with anticipation & a bit of fear. I kept reassuring myself I could not get in trouble if it was an accident & she'd never tell anyway because it would be too embarrassing.
I heard the vacuum hose come out of the closet so I clicked on my music loud so I would not hear her but she would hear the music. I quickly stuck my fingers into the Vaseline jar then started to stroke nice long lengths on my long hard cock. I closed my eyes peeking just a bit so it looked like I was deep into my music & jerking. I could not hear anything but music waiting for her head to come over the top stair. I'm not sure what she did but it took a few moments, then I saw her. What a rush! I kept stroking my cock peeking through the slit of my eyes as she came all the way up the stairs. She got to my door then stopped dead in her tracks. All she did was look so I just kept going like I didn't know. She stepped back a bit but I could still see her behind the door doing her own peeking. My cock was about to explode so I stopped pumping it & held it tight at the base squeezing it really hard. It was too much to handle & my cum started to flow. I pumped out a huge rope of cum then went right back to stroke my cock through to the end. I made sure my orgasm was a good one for her to watch. I was pumping my slippery shaft & grunting loud until every drop of semen was gone & my body was content.
As soon as I was done I felt really bad like I had done a terrible thing. I sat up & she disappeared back down the stairs. I was wiping myself off like I usually did with paper towel then I heard the vacuumed down stairs. I was not sure what to do so I cleaned up & got dressed & sat on my bed. I thought about it then decided I would face whatever was going to be now. I went downstairs & when she saw me she smiled & turned off the vacuum. 'Are you sick today' she asked. 'Yes' I said. I have a bad headache'. 'Oh, I just arrived' she said.
That was about it. She went back to work & I watched her rock from one long leg to the other lifting one bare foot then the other vacuuming like nothing happened. I turned to leave & she yelled 'I hope you feel better soon' giving me a big smile. I went upstairs thinking about what I had just done & my cock was already getting hard again. I felt awesome! I just jerked off while a gorgeous woman watched me. What a thrill!
Shortly after the vacuum stopped & I could hear her coming up the stairs. I was straightening my room out a bit & she stopped at my door. She said 'if you're home with a headache, you really should close your door on Thursday mornings. You never know who may see you, then she paused & said with a smile, 'resting'. She then told me loud music makes a headache worse, then walked away giggling.
I went to the door of my parents room & stood there while she vacuumed. She stopped & asked what I wanted & all I said was 'you know, you saw me didn't you'. 'Sure I did' she said. 'What do you expect with the door open like that'. I asked her if everything was OK & she slowly nodded yes. She said 'your secret's safe with me' then started to vacuum again. She turned it back off right away & told me it would be best if I did not have any more headaches with the door open. She looked back at me & told me I should go rest or something, with the door closed, then gave me a nice smile. I knew right then that I got away with it & she liked it too.
That memory has been a part of my masturbation thoughts almost every time that I've jerked since that day & it was almost 21 years ago. I still remember those long legs, the tight little ass & her cute little feet with bright red nail polish on her toes only. She sure made an impression on me. The only thing I can't remember is her name.