Started solo and ended together
Happened last night so I figured I might as well write it out since it is still 'fresh' in my mind; even though I don't think I will ever forget it .. I work at home so pretty much anything goes . Well I was sitting here surfing because I finished what had to be done for the day . Well ya know what happens .. So I start stroking feeling more and more aroused and I start rubbing my asshole as I stroked .. Deciding to get out my small thin butt plug I started using it like a dildo and stroking . Because of this I was in a position where I couldn't really see my door .. Anyway I am having a great time edging my ejaculation when I hear this Ahemm .. I froze, butt plug in, dick in hand,and face down away from the door. I slowly look over hoping to see my Ex who still had a key .. When BAMM it was the cleaning lady I also had given a key to. It seems I forgot what day it was. I turned so flush like a little school kid not sure what to do first.
I decided the butt plug was the immediate thing to remove as I pulled it out she said to me in the softest; sweetest; almost motherly voice, 'Are we enjoying ourselves??' Seeing the position I was in I had to answer so I said Yes very confidently .. With that she said Well can I watch? 'I have never seen a man who enjoyed his ass played with like that'. I was floored here she was 50+, a bit larger and all. I became more flushed with embarrassement if that was possible . So I just asked are you serious ?? She said 100% if you don't mind. I told her I didn't as long as she didn't mind if I looked away cause I was not sure I could 'perform' for anyone. She said. 'Of course I understand .' So with that I got back to where I was before. By this time my cock had gone limp so I just started slowly rubbing it and playing with my ass again, after about 5-10 minutes of this I started to get erect almost forgetting she was even there until I heard a soft moan! I never stopped what I was doing but I turned my head to face her and there she was with her dress hiked up rubbing her noticably wet panties . Man was that sight hot for me! I started moving my hands faster, stroking and moving the toy in and out of me. Watching that must have really got her cause she started almost pushing her panties in her soaked pussy. I moved faster and faster until finally I shot my load all over the bed .. She gasped and moaned .. Well afterwards we had some silence and we were not sure what to say to each other. I pushed the butt plug all the way in and sat up. She said 'Well I guess I have laundry to do today', removed her soaked panties and tossed them at me. 'Maybe you can use them later to help, Now let me get your sheets'. I stood up, panties in hand and speechless. She just stripped the bed and started to do her normal chores. Nothing happened between us but her panties did help later that day and she did watch me one more time . Then like nothing happened she told me to have a great night and went on her way. I am sitting here today still unsure what to do or say but I know I am sniffing her panties and stroking again thinking about it LoL .. I know who is getting a great Xmas Bonus this year ;)