Dorothy - Thirty-six Years Worth

by Just Plain Bob

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, Cheating, Slow, .

Desc: Sex Story: The slut in my life.

The first time I saw Dorothy I was fourteen years old. I was working at the Wrigley's Super Market on the corner of Dumbarton and Grand River as a bag boy and I had just gotten off work. I lived with my parents in an apartment house on Dumbarton and as I came out of the store, turned the corner and started up the street I saw a woman walking up the street in front of me. A woman with great legs, wearing high heels and with a walk guaranteed to give any man a hard on. Even at that early age I had a thing for great legs and high heels. I'd had it for almost two years, ever since my mom and dad got careless and left their bedroom door open. I'd seen them going at it and mom's nylon covered legs and high heel clad feet waving in the air was a sight that was burned into my memory. I have been a garter belt, nylons and high heels freak ever since.

Anyway, I slowed down because I didn't want to pass the woman; I wanted to watch that ass and those legs for as long as I could. I was surprised when she turned in at the same apartments were I was going. Usually I took the steps from the lobby up to my floor, but when the woman went to the elevator I stayed with her. She got on and I rode it to the third floor with her. As she was getting off the elevator she turned to face me:

"I know you live on the first floor so why did you ride up with me? Was it because of my ass or my legs?"

I didn't say anything and I'm sure I blushed redder than a firetruck. She patted my cheek and smiled at me, "No matter, I appreciate the attention. Tell your mother that Dorothy said hi."

A couple of months later my parents bought a house on Taylor and we moved.

Taylor was still within walking distance of the store so I was still working there after school and I occasionally saw Dorothy walking on the street and if she saw me she would always wave, and once she even blew me a kiss. Then I heard that she and her husband had bought a house and moved.

The next time I saw her was about two years later at my mother's birthday party. She was there with her husband and she still looked as great as ever. In addition to great legs and a fabulous ass she also had a marvelous set of tits. I hadn't noticed that before because she'd always had a coat or a jacket on. That night she was wearing a low cut blouse and every time she bent over you could see almost to her navel - and she wasn't wearing a bra. It seemed that every time I was looking at her, and it was often, she would turn her head and catch me and I would quickly turn my head away, but I was not quick enough to miss seeing her smile.

Since the party was almost all adults I eventually headed up to my room. There is nothing more boring to a teenager than to be around a bunch of drinking adults. I was going through my comic book collection when there was a knock at my door, it opened and a woman's voice said, "May I come in?" I turned and saw Dorothy standing in the door. I guess I was pretty tongue-tied and when I didn't say anything she came into the room.

"I need a favor. I just went to the potty and I need to make sure my seams are straight before I go back downstairs. You won't mind, will you? I seem to remember that you like my legs."

She turned around and lifted her skirt all the way up to uncover her panty clad ass and I got an immediate hard on.

"Are they straight?" and I mumbled a "Yeah, sure" and waited for her to go so I could beat my meat. She dropped her skirt and turned around, "Thank you sweetie" and she leaned forward and kissed me on the lips. I felt her tongue briefly flick into my mouth and then she turned and left. I'd just had my first experience with a cock teaser.

The next time I saw Dorothy's ass was eight years later. I'd gone to college and following that I had fulfilled my three year obligation to Uncle Sam (ROTC had paid my way) and I had returned home to the house my parents no longer shared. I was going to stay with my mom until I could find a job and a place of my own. I got home a little earlier than expected and since I only had a back door key I went around to the back of the house. I set down my B-4 bag and was getting the key out when through the window I saw a very naked Dorothy lying on the kitchen table while a man I didn't know (and one certainly not her husband) had his face buried in her pussy.

A nice guy wouldn't have done what I did next; he would have waited for her to have her orgasm, but I owed her for that night in my bedroom. I picked up my bag and then dropped it as loudly as I could and then made as much noise as I could putting the key in the door and unlocking it. Through the window I saw both of them scrambling to get out of the room and in passing I noticed that for a woman in her forties Dorothy had a superb body.

As I was opening the back door I saw my mother pulling into the driveway. I stopped and waved at her and by the time I got in the house the man had his clothes on and was sitting on the living room couch. Dorothy was coming down the stairs in a loose fitting dress and from the way the material moved over her tits I could tell she hadn't taken time to put on a bra. My mom came in and after hugs and kisses she introduced me to her new boyfriend - the guy sitting on the couch. I looked from mom, over to the guy, and then to Dorothy who shrugged and winked at me.

Mom, Jack and Dorothy were going to go out to the airport to pick up Dorothy's husband and while they were getting ready to go I was in my old room unpacking. There was a knock on the door and it opened and Dorothy came in.

"I need a favor sweetie" and I turned around to see Dorothy standing there with her skirt pulled up to her waist. She was wearing nylons, garter belt and high heels and my cock instantly came to the position of attention. "Are my stockings on straight sweetie?"

I wasn't sixteen and inexperienced anymore and I took two steps forward and ran my hand up her leg till I reached her panty clad pussy. It was so wet that I could feel it through the material of her panties.

"God sweetie, if you could only have come home yesterday while my hubby was still in Dayton we could have had some fun together. Be nice and don't tell your mother what you saw" and she walked out of my room. Still a fucking cock tease.

Several more years went by during which time life was both good and bad to me. I found a great job, married a beautiful woman and then lost both. My boss met my wife Megan at the company Christmas party, decided he had to have her and started sending me out of town on business trips and while I was gone he seduced her. I came home early one day, caught them, broke his jaw and threw both of them out of the house. The broken jaw cost me my job of course, but I got the last laugh when his wife found out how and why his jaw got broken and she divorced him. Her financial settlement ruined him and with no money to support the both of them he dropped Megan. I found a job that was just a tad better than the one I'd lost and life went on.

One day I stopped by the house to visit my mom and Dorothy was there. She and her husband had moved to Dayton, but she came back to Michigan several times a year to visit family (and to fuck around on her husband). It was Dorothy's fiftieth birthday and she and my mom were getting ready to go out and celebrate. Dorothy didn't drive so my mom and her current boyfriend were going to go out to the airport and pick up Dorothy's husband and then come back and pick her up. Dorothy said:

"Don't bother. I'll take my shower and then Rob can bring me over to the bar and I'll just meet you there. You will, won't you Rob? Take me, I mean?"

I wasn't sure that what I heard was what she said. To me the way she said "Take me" meant that I was supposed to push her down on the floor and fuck her as soon as my mom and her boyfriend were gone. My mother said:

"Would you mind dear? It sure would save us a lot of running around."

I said I would and mom and her boyfriend left. Dorothy looked at me, smiled and said matter of factly, "Are you going to fuck me before or after my shower?" And then she gave me a wicked grin and said, "Or are you going to do both?"

Her housecoat hit the floor and I was amazed; for a woman of fifty her body would have put most twenty-year-olds to shame. She spun around in front of me and said, "You like it? You damn well better considering all the exercise I have to do to keep it this way."

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Story tagged with:
Ma/Fa / Consensual / Heterosexual / Cheating / Slow /