Yes, but sadly only once
When I was about 30, the company I worked for decided to have me open an office in London. I packed all my stuff, vacated my apartment, sold my car and was ready to relocate when there was a hitch of some kind with my work visa? I had been living with my girlfriend temporarily, but one night a friend of mine came over and ended up fucking her roommate. That didn’t turn out well for some reason and the roommate got pissed off at him, and then me by association. She didn’t want me living in the apartment any more, so I had to find some temporary housing.
I ended up finding a room in a very large house (sort of a mansion) which was owned by a middle-aged German woman. She was taking care of her very old and ailing mother who also lived there. They put me in a large upstairs bedroom. I rarely saw my landlady and never saw the mother since the house was so big. Sometimes when I came home at night the landlady would be sitting in a downstairs living room with a glass of wine reading a book. We’d share pleasantries, but never really had a conversation, although one time she told me it would be OK if I brought my girlfriend over to my room. She gave me a knowing smile when she said that, and I took her up on it a couple of times, but I didn’t really feel comfortable since it was like I was just staying in a room in a stranger’s house.
Since I had sold my car, my girlfriend who worked for the same company would stop by every morning and give me a ride to work. She’d usually just pull up to the curb and I’d see her from the window and come out. If I didn’t show up within a few minutes, she might tap the horn to let me know she was there.
The landlady was good-looking for her age and pleasant enough. I assumed she was divorced (no ring), but we never really talked about that. This was in the days before MILFs were discovered to be an untapped sexual resource, and I considered her to be too old to pay much attention to. She was probably only in her 40’s. I remember earlier in my life not dating a girl because she was 27 and I was 22 at the time. How ridiculous.
Anyway, every morning I would spend a half hour down in the kitchen drinking coffee and having breakfast while I waited for my ride to show up. Sometimes the landlady would be there and we would chat briefly, but usually not. One morning she was there and I was making coffee with a French press that I didn’t really know how to use. I ended up pushing down too hard on the plunger and coffee and grounds shot out all over the kitchen counter and floor. My landlady saw the mess and came over and started cleaning it up with me. At some point she was standing next to me and I could smell her hair. She was wearing a pink robe with a while belt. We bumped into each other as we were cleaning and our faces ended up close to each other. In a split second we started kissing. I ran my hands over her body and she did the same to me. I was hard instantly. In retrospect I think i must of had a thing for her the entire time. I had never been with a woman this old and she knew exactly what she wanted. She reached down, undid my zipper and felt my hardon. When she opened her robe I could see she was completely naked underneath and looked much better than I had imagined. She took my hand and led me to the sofa in the adjoining living room. Somehow I got my pants down and she straddled me still wearing her open robe. As she was moving up and down on my cock I started worrying about my girlfriend showing up, which was affecting my concentration. My landlady must have had some tremendous built-up horniness because she seemed to come within a couple of minutes. She also knew how to concentrate my attention by reaching back and grabbing my balls until I came. When she got up and I saw a glob of my cum fall onto my thigh. She seemed very mater-of-fact about the entire thing.
Ten minutes later I was in my girlfriend’s car heading to work. We somehow got into an argument during the drive, and I remember thinking to myself, “I’m going to break up with you someday.” As for the landlady, we never had a repeat performance. I only saw her a couple more times and we exchanged glances, but I was either with my girlfriend or on my way out the door so nothing happened. My work visa got cleared up soon afterwards and I moved out. I did think about her a lot until I met my wife. Anyway, that’s my landlady story.
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