I am 39 year old male. My wife and I have a business that has started to do very well. We recently moved into our new home. We also decided we should have a cleaning lady that comes in once a week or so. When my wife and I spoke about it she made a comment that we didn't need a 19 year old sexy cleaning lady. I was fine with that. We ended up with a nice lady named Anne Mary. She is 59 years old. She is fantastic. She is quiet but friendly. She does a great job. So my story really starts here. I was playing and getting naughty with my wife one night. So we went to bed. I felt I needed to use the washroom and my stomach decided to rebel?! We ended up not fooling around cause of how I felt. Next morning, wife leaves for work. I stayed home. Still not 100%. It was wednesday. Anne Mary comes on wednesdays. She let's herself in. When I heard her open the front door, I went to the top of the stairs to let her know I'm home. I said I would be sleeping, but to not worry and she can still get to the ensuite to clean it. A couple house later, I got my phone and started to look through some porn. This got me to get naked and stroke myself. About 20 minutes in, my door started to open. Slowly and quietly. Anne Mary backed into the room carrying her bucket of supplies. She quietly closed the door, and turned around to face me. She stopped and stared. I was still naked and stroking my cock. She raised her gaze to my face and I winked. She returned her eyes to my cock. I continued. She looked at my face again. I smiled and said "you like what you see?". She started to fumble. She was stammering her apologies and trying to open the door. I stopped her and said, "I'm sorry. I was enjoying myself and you opened the door. I was too deep into my fun so I thought I would push my luck. I didn't mean to offend you. I just think its a turn on if you want to watch". She was saying she should go. And she said it was our secret and she should have knocked. I asked her to please not leave. And that I just want her to watch for a few minutes. All this time I stroked my cock. I was so hard! My cock was pulsating. She was alternting her gaze from my face to my cock. She put down her bucket and smirked a bit. I asked how long it had been since she saw a hard cock. She said "far too long". I said to come closer to get s good look. She tentatively walked closer. She just kept watching my cock. I slowed a little and stopped a few times to hold off cumming. At one point I let go and let it bob and throb in the air. I offered her to touch it. She shook her head no. I reached and took her hand and put it on me. She closed her grip and stroked. I was in heaven. I then said, "yes Anne Mary, please make me cum. I want you to see me cum". She looked at my face, smiled and picked up speed. I let out a groan and came. I came so hard it hit the headboard, the next shot hit my shoulder, the next my chest, and the following few landed on my stomach. She actually said, "oh my! You can really fire off a load!". I chuckled. She giggled. Then I said thank you and I was sorry to put her in that position. She said it was alright, but she didn't think it should happen again. I agreed. She isn't an ugly woman, but she looks her age. A little heavy, but not big. Grey hair. Glasses. You can picture her. She looks like a regular grandma. I'm not into old ladies, it was just 'a woman to pull my cock'. But we get along great, and she has even made a few wise cracks when my wife can hear like "do I need to clean headboards today?". I would probably do it again if the opportunity came up.