Housekeeper (moms best friend)
As a k** growing up, I would often go with my mom as she visited her lady friends. At some point I began always needing to use the restroom while we visited so I could search for the ladies dirty panties. I loved to sniff them while jacking off.
One lady in particular was my moms very close friend and we use to visit her often, both at her and her husbands house and their lake house. This lady was always very hot and I was checking her out all the time growing up to the point where I use to let her catch me looking at her tits, ass and pussy all the time. I use to stuff her panties in my mouth and shoot a load all over the place every chance I got. This lady, being such a close friend of my mom, would often come to our house and do some housework for my mom as she was always very busy at work. It was just normal to have this lady around, so I was always checking her out. As I got older, she would know where my eyes were and once or twice once I got to high school, she told me I had better keep those eyes under control, but she never ratted me out to my mother. As time went on, I got a little more bold to the point where a couple of years ago, she was eating lunch at our house with just me and my s****r at home, and I was looking right at her pussy as she sat on the floor in front of me. She got sort of a red face, and said something about my “wondering eyes”.
I became pretty flirty with her once I became “legal”. When I was 18 a couple of years ago, she was I think 44, but still very fit and very hot (see housekeeper pic’s). There was just something about her that made me really horny and I would often sit in my room and jack off while she was roaming around the house doing some house work.
Early last summer, she was telling my mom one day about how big of a ass her husband was (something I already knew) and that she was thinking about leaving him. I hid out to hear them talk and at some point she told my mom that she had not had sex in two years. I thought, WOW how could some lady that good looking not have sex for so long. I knew then that I needed to find a way to try and get my dick in her. I knew there was a very good chance she would tell my parents if I did anything real dumb, so I begin thinking. I had at that time already set my s****r up to see me shooting a big load of cum, so I decided to do the same with this lady.
She always came to our house on Fridays and more often than not she would spend nearly the whole day there. Most of the time my s****r was home as well but my parents always left early together for work and never came home during the day. My room is over our garage so I can see everyone come and go so there is little chance of me missing someone showing up. A few weeks went by and I had figured out what I wanted to do, so all I needed was for my s****r to be gone.
Finally, my s****r told my parents that she was going to be gone from Thursday until Monday the next week. I made sure I did not screw around with my girl friend or shoot any loads for a few days leading up to that Friday. Like clockwork, my parents were out of the house by 6am and my s****r was two hundred miles away. At around 9am that morning the lady showed up. I had figured out that she did things more or less the same way every week so I knew she would do work and laundry downstairs in the morning and not come upstairs until after lunch sometime. I hung around downstairs more than normal and at some point she asked me if I wanted her to fix me something for lunch. I said sure and we sat down together at the bar in our kitchen and talked a little. At some point I asked her if she would be cleaning the bathroom upstairs and she said yes and that I should take a shower before 1pm if I needed to as she would be up there around that time.
So at 1230 or so I put my little plan in place. My bathroom is right across the hall from my bedroom and it has a large counter around the sink just inside the door. I stripped down completely naked and began surfing porn on the internet. Of course it didn’t take me long to get nice and hard so I began jacking off. I made sure I was really worked up well (not hard to do with this lady in the house) and from time to time, I would just cross the hall and sit on the counter with the door wide open and jack off. I could hear her still downstairs but I would just keep moving back and forth between my room and the bathroom hoping she would come down the hall.
At some point I could hear her coming upstairs with some cleaning stuff, so I hurried over to the bathroom, jumped on the counter and stroked my rock hard cock. It wasn’t long until everything feel into place. There I was with my cock about ready to bust jacking off when in she walked. She quickly stopped and back out the door, saying “I’m so sorry, I had no idea you were in there”. I could tell she had not gone far down the hall, so I got up and stuck my head around the corning and there she was. I told her I was sorry and she just gave me a sly smile and said something like “ya, I’ll bet your sorry”. At that point I stepped out the door fully naked with my cock still hard as a rock. Again, she didn’t really make a mad dash or anything to get away but she kind of turned away and said you better get that thing covered up and put away. She added something like “what would your mother think if she knew what you had done” but still didn’t rush off. At that point, I figured we had reached the point of no return so I just walked up behind her and turned her around. I had a hold of her hand and placed it on my hard cock, but she said “this is a very bad idea and it is not going to happen”. I told her how I had always dreamed about her and how hot I thought she was. I told her I was no longer a k** and that I wanted her. Again, she said this is a very bad idea. She says, you are 18 and I’m as old as your mother. I told her I could care less about that but she went on to tell me that she was also married to a guy that would kick my ass.
I placed her hand on my cock again and backed back into the bathroom, pulling her in with me. I was jacking myself off with her hand and I just leaned forward and began kissing her on the ears and neck. I didn’t take long for her to give in just enough to let me do anything I wanted without her stopping me. I continued to kiss her, rubbing her tits and finally running my hand down to her pussy. She just leaned back and let me go. Finally she buried her tongue deep in my mouth and began jacking me off on her own. It didn’t take me long, with my knees about to give and she must have known I was about to go off. She just squeezed harder and jacked faster to the point that I just started shooting shot after shot clear across the room. She ended up saying something like “holy fuck!”
At that point my mom said one night that she had left her husband and moved to her f****y’s lake house. When she came to next Friday to clean, she could help but grin at me when she saw me. I told her I would never tell and that I wanted to eat her pussy and fuck her in the worse way. She more less told me no way, but over the next couple of months I worked on her and on another Friday at our house alone, she came into my room and I ended up licking her pussy and her ass from behind. My cock again was rock hard and I tried to slip in into her but she said no fucking. She just jacked me off again that day and she told me she had never seen anyone cum like that. This stuff went on for a while, and finally she gave in at some point and let me fuck her. Since then, we have been meeting in private either at her house when her k**s are with their dad, or at their lake house. This has been going on now for over a year, and she did break it off at one point for fear my mother would find out, but we have been together again this summer.
I love girls my age, don’t get me wrong, but there is something about these older ladies that just makes me hotter than hell. With this one I’m living a dream right now.
Posted by dogg2009 2 years ago Views: