I used to keep extensive, detailed journals when I was younger. What follows are based on some of those entries.
In 1986 I was 20. Miss "Willie" was 57. She and I had an amazing secret sexual relationship that lasted about 3 years.
It started with me running a weekly errand for my grandmother. Miss Willie was a member of the church we attended. She and grandma were friends and both members of the church Administrative Board.
We lived in the Eckington neighborhood in DC. Miss Willie lived in Parkview, which just happened to be adjacent to Petworth, where most of my friends lived. Almost every Saturday I was grandma's courier, dropping off a note or document while on my way to hang out with my boys. This started the summer after I "took a break" from school.
Miss Willie was a widow and a grandmother. She was a petite woman, about 5'6", and maybe 120 lbs. She had a nut-brown complexion and dark brown eyes. She usually dressed conservatively, and always wore cat-style glasses with her grey-streaked hair tied in a bun, which extended to her waist when she let it down. At first glance, most people would think she was a librarian or a school teacher -- Miss Willie always gave you the impression that she "knew something that you didn't".
I liked her, she was always nice to me. Plus, she was a "hugger", which I especially liked because she had really large, soft breasts.
The first few times I delivered something to her we would spend a few minutes talking about church gossip or the Redskins, or music, or whatever. The next week, she was watching a college football game and invited me to stay and watch it with her. Turned out we were both USC Trojans fans. I stayed the whole afternoon. She made fried chicken and we had a few beers. We joked and even flirted a little. We made plans to hang out again for some upcoming games.
The first time I got a hint of more than just "hanging out" was the time I stopped by after Miss Willie had finished her yoga exercises. She answered the door wearing a red leotard and black tights; she looked like a "black Jane Fonda". She was a little sweaty, her feet were bare and her hair was tied in a single, long pony-tail. I took my time that day. She knew I was checking her out and didn't seem to mind because she took her time too. I got a serious hard-on watching her massive tits bouncing around in that thin, stretchy material. She noticed, and she enjoyed it too, because her nipples were at full attention by the time I left.
In addition to football, we both also liked movies, so we agreed to go see a few together; our first movie was "Platoon". The night after seeing one of the Star Trek movies, our usual goodnight-hug, turned into a goodnight-kiss. And I do mean "KISS"! Our tongues did some serious wrestling, and we spent a while grinding and feeling each other up pressed against her apartment door.
A week later we went to the opening of the new Smithsonian African Art museum and then went back to her apartment. She made us dinner, and afterwards we cuddled on the couch and watched some TV. We kissed. Emboldened by the kissing, I took things a step further and fondled her breasts. She unbuttoned her blouse and removed her bra.
