Miss Willie and Me

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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 Çanakkale Escort 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.

I probably came a little bit.

Miss Willie had the biggest tits of any woman I had been with at that point in my life. She encouraged me to suck and lick and worship them — she REALLY liked having her tits played with. She literally “served” them to me, holding one up for me to suck and then the other. I teased those big brown nipples for what seemed like hours. I put my hand up her skirt and she got herself off grinding against my palm.

She gave me a blowjob after that, but I was so worked up that I didn’t last long. I shot my loud into her hands and mouth after only a few strokes and sucks. She promised me that we would take things a lot further the next time.

She invited me back to her place three days later. We talked and ate and watched some television. I gave her a foot massage and we kissed and touched. Things really got started while Çanakkale Escort Bayan I was helping her clear the dishes.

She was wearing a housecoat — under it she wore nothing else. I was on my knees putting something into a lower cabinet, and when I turned back her crotch was just inches from my face. I lifted the front of her housecoat and put my face up into her pussy. Miss Willie laughed at first, thinking I was just playing around, but we both got serious once I started licking her. She backed up against the counter and spread her legs for me, lifting one over my shoulder.

Miss Willie never had a problem guiding and encouraging me in ways to please her. She told me how she wanted her pussy licked and I did my best to follow her instructions. She removed the housecoat and pinched and teased her nipples while I ate her out.

That was the first time a woman came on my face — I loved it.

She then gave me an amazing blowjob; luckily, I didn’t immediately blow my load this time. We eventually made it to her bed and she showed me how flexible and limber the yoga exercises had made her. We tried to fuck each other silly. That was the first time I spent the night at her place. I went to work the next day wearing the same clothes, so she suggested that I start leaving an extra set.

I went back to her place three more times that week.

Miss Willie was a very adventurous, free-spirited, open-minded woman. She thoroughly enjoyed sex and had a very strong sexual appetite.

On one of our movie dates, she was insistent on giving me a blowjob (I think we were seeing “Bull Durham”). It was a matinee and there weren’t very many people there, but I was convinced that someone would see us. I was right — some uptight lady saw and went to snitch. Luckily we left before a manager showed up to kick us out. That was the last time we went to the Uptown Theater.

Once, she suggested that we not physically touch, besides kissing. Instead we both got naked, looked at porn and watched each other masturbate. It usually takes me a Escort Çanakkale long time to reach a climax when jerking off, but Miss Willie came three or four times.

One weekend, she suggested we get “freaky” while she showed me a few yoga moves. We used an entire bottle of massage oil. That was also the first time she asked me to fuck her ass (another of her favorites).

And (of course) we eventually had sex at the church. As an administrator, she had a set of keys to the building and asked that I meet her there one evening. I went with the intention of helping her carry some files home, but we ended up fucking on the leather couch in the minister’s office.

About a year later she asked if I wanted to go to a party with her.

This was my first swinger’s event, Miss Willie had been to more than a few. It was at a hotel suite in downtown DC. We went, but it turned out to be boring — the people throwing the party seemed more interested in flirting and talking about sex, telling sex stories or making sexual innuendos, than actually “having sex”; so we left.

The next party she took me to was fucking mind blowing! This one was at a private home in Takoma Park and she seemed to actually know everyone. There were probably 20 people, and we were the only Black couple. I was the youngest male as far as I could tell. Miss Willie introduced me to the hostess, a 40-something blonde (I think her name was “Maris”), and a few others. I think some of the other party-goers were her co-workers.

I had a threesome with Miss Willie and Maris (my first time with a white woman). This was also how I found out that Willie was bi-sexual — watching her go down on another woman was so fucking hot! A month later she invited her friend over to join us for another threesome. We would attend at least two more parties at her place in the next year.

The last time that Miss Willie and I got together was the week before I moved to NYC for a job. As expected, she made it memorable.

By this time we were experimenting with bondage. We took turns tying each other up, teasing and fucking each other’s brains out. Unfortunately, after I moved to New York, circumstances and timing prevented us from ever hooking up again — but we definitely tried.

By far, those three years with Miss Willie were among the most sexually memorable and satisfying times of my life.

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