I have a thing for older women, more specifically, older married women. It started when I was sixteen and it continues to this day, some twenty odd years later. I guess it's fair to say that I got an early start sexually. I was playing "doctor" with the girl next door when I was eleven and just before my twelfth birthday I accidentally got to see my parents making love. It was only natural that the next time Kay and I played doctor that I had to show her what I'd seen and even though I didn't get penetration, I did get off and it felt so damn good that I had to keep on trying. Kay must have liked it too because she kept trying with me and the day finally came that we both lost our virginity. Unfortunately Kay moved away shortly thereafter, but I still think of her and I'd like to think that she still thinks of me.
By the time I was sixteen I had managed to get myself laid a dozen or so times, almost always by a girl a year or two older than me, but getting laid as a teenager, as I'm sure most of you know, is very hard work. The success rate is like one out of fifty tries unless you are lucky enough to have a Carol Meade (school slut), but the Carol Meade's of the world are few and far between and they are always found on the arms of the older guys, guys who already have cars.
It was the summer of my sixteenth year and my best friend Tom, who lived just across the alley from me, and I were going to hop on the DSR and ride down to Briggs Stadium to watch the Tigers play the Orioles in a double header. I went across the alley and into Tom's back door (we did things like that back then - go into each others house unannounced) and called for him. He didn't answer, probably couldn't hear me over the shower that was running, and so I headed back toward his room. He wasn't there so I figured that it must be him in the shower and so I headed for the bathroom. The shower stopped just as I got to the open bathroom door and I saw Tom's mother stepping out of the tub and onto the bathroom floor.
I'd seen several naked girls in the last couple of years, but I'd never seen tits like those on Mrs. Rose. She noticed me standing in the doorway and I expected her to scream and grab the shower curtain to cover herself, but instead she just looked at me and said:
"What's the matter Dan? Never seen a naked woman before?"
The look on my face said it all.
"You haven't, have you? Well, I don't mind if you look at me. There is nothing wrong with nudity and I think that if you are comfortable with your body and with yourself you don't need to be ashamed. Why are you here?"
I stammered out about the ball game and she said:
"I thought Tom told you. He is spending a week with his grandparents. While you're here" and she tossed me a towel, "dry my back for me please."
I caught the towel and with trembling hands I began to rub the water droplets off of her back. "Thank you," she said when I had finished drying her entire back and she turned around to take the towel from me and her breasts brushed against my arm. She either didn't notice or didn't care and she took the towel from me and walked back to throw it over the shower curtain rod. I watched that magnificent ass walk away from me and my dick was harder than I could ever remember and I knew that I had to hurry home so I could jack off. I started to turn and go but she said:
"Don't run off, I need you to do something for me" and she asked me to follow her. She led me to her bedroom and said, "Just wait a minute for me to throw a few things on. I'm going to need help with the zipper on my dress."
She sat down on the edge of the bed and rolled on her nylons, stood up and put on a garterbelt and then stepped into a pair of high heels. She walked over to the dresser and bent over, digging through the drawer and leaving me to stare at that ass and her hanging tits. Her legs were slightly apart and I could see her hairy mound between them and I was hurting bad. I was torn between running for home and taking care of my self and staying to see as much as I could.
She stood up and turned, panties and bra in her hands, and walked toward me. Handing me the bra she said, "Here, hold this" and then she stepped into her panties. She took the bra from me and turned her back, "Hook me up" she said and as I stepped forward to do it my hard cock touched the cheek of her ass. She spun around, bra dropping to the floor.
"Oh Danny, how stupid of me. I'm sorry baby, I should have known better. It's all my fault. Here! Let me make it better."
She went to her knees in front of me and before it even registered on me what she was going to do she had my cock out and in her hands.
"Oh it's a nice one! Much better than Tommy's and almost as nice as my husbands" and then she took it in her mouth.
I'm ashamed to say that I came almost immediately, but Mrs. Rose had more surprises in store for me. She kept my dick in her mouth and swallowed every bit of my cum and she kept her mouth on me until I was hard again. She stood up and undressed me, led me over to her bed and for the next two hours Mrs. Rose rocked my world. Finally she said:
"You have to go now Danny. Mr. Rose will be home soon and I have to clean up. This is our little secret, right? You won't tell any one about this, will you?"
"No Mrs. Rose" I stammered, "I'll never tell any one, honest."
She gave me a smile, "Good, you keep quiet about this baby, and maybe we can do it again."
We did, many, many times over the next two years and after Mrs. Rose there was no going back to girls of my own age. Mrs. Rose taught me a lot during those two years and I was a pretty accomplished lover when I went off to college. I was also a whole lot wiser about a few things. Remember her comment " ... yours is much better than Tommy's"? It turns out that she and Tom had been getting it on long before I came on the scene. I found that out one day when I was busy pounding her pussy and we heard:
"Mom, I'm home!"
Mrs. Rose pushed me off her and rushed me into the closet and warned me to keep quiet. Tom came into the room and said:
"Waiting for me I see."
Mrs. Rose said, "I'm always ready for you baby, you know that" and then I got to watch the two of them bounce around on the bed and surprisingly enough I got a charge out of watching. When she made Tom quit, "Daddy will be home pretty soon and I have to get cleaned up" and he was out of the room she came and got me out of the closet. As she led me to the bed she said:
"We have just enough time to finish what we started before I have to get you out of here" and I got my very first sloppy seconds. "You won't say anything about this, will you?"
I laughed and said, "And ruin what I've got going here? Not a chance."
She patted my cheek and said, "You are a sweet boy. We can talk about this tomorrow."
I stood in the closet and watched Mrs. Rose and Tom a couple of more times and Mrs. Rose always timed it so I could screw her one more time after Tom was done and before her husband got home. I always wondered if Tom ever stood in the closet and watched me, but if he did he never gave any indication.
I owe Mrs. Rose a lot. I got three things from her that I carried forward into my life, a thing for older women, a desire to stand in a closet and watch, and the confidence and self-assurance that I needed to go after older women. In college instead of chasing after the girls my own age I haunted the malls and shopping centers looking for older women and I had surprisingly good luck in finding them. There are a lot of dissatisfied housewives out there if you know where to look and have the balls to approach them. Of course you do occasionally have to put up with a crying baby, but to me it was always worth it.
I went all the way through college without ever screwing a girl my own age and my senior year was spent almost entirely in the company of a thirty-eight year old divorcee. But I never got to watch from the closet while in school though I think I may have been watched a time or two. I was surprised at how much I missed it.
.... There is more of this story ...