Older Ladies Who Teach Us to Be Men
Like a lot of guys, I had the normal exeriences with girls in the neighborhood, high school classmates and college coeds. I love perkey titties and tight bottoms as much as any guy I know. But, many of my most satisfying early sexual experiences were with "Mrs Robinson's", or "Stiffler's Moms" (we didn't have a word for it back then, but MILF is the current term). Many of whom were in the circle my parents ran with, or were the moms of my friends. At that age, shall we say up to about 24, my best quality was the ability to lift and carry things, or mow things or clean things.....thank heaven for college and professional training, I might have been a handy man all my life.....but that "young mans' ability'.....seemed to lead to quite a few encounters ......(my other particularly good quality was muscled shoulders and arms and legs, and a dick that stood up quickly and easily, and could recover very quickly)...... where a somewhat older woman, shall we say 30-50, led to me learning a lot of about how to please a woman. It's led to a.....minor fetish.....where I like porn with somewhat older lades fucking somewhat younger guys.....not kiddie porn, just Stifflers Mom doing her thing.....I guess you could call it nostalgia. Sadly, I don't have much of a collection of visuals, so if any readers out there have stories or visuals to share, I'd be appreciative.
One of my earliest encounters was when I was hired to "move stuff from the attic" for a neighbor lady. She was an attractive burnette, age maybe 40, old enough that I normally would not have thought about her sexually, who had lost her husband a couple of years before. She was getting ready to move, and needed a strong back. After several trips up and down from the attic, where she always seemed to want to put her hand on my leg or hip to "steady me", I was helping her go through and sort boxes in the living room. Afterwards, she had gotten me a soda, and as she bent over to go through the boxes.....to be junked (my later job) or saved....I had several nice looks down her housedress. To my surprise......who knew women in my mom's age even had titties......I noted that she had pretty boobs, that would more than occasionally separate from her bra, showing me dark brown nipples. At some poinit, after staring at her boobies for an extended time, I looked up, to find her looking at me, and smiling. She asked me if I saw anything I liked, to which I stammered out yes. She asked if I would like to see them better, which led to more stammering, but a definite yes.
To my delight, and instant hard on, she stood up, and proceeded to unbutton her dress, unhook her bra, and drop her panties. She asked if I liked what I saw, to which I could only nod, and said, "let's see what you are working with". She pulled up a chair, sat, and proceeded to undress me, which led to me cumming on her titties as soon as she pulled my underpants down. Rather than be upset, she said "Well, I see thatyou like me", after which she used her fingertip to wipe my cum off her titties and put it in her mouth, I didn't quite cum again from that, but it was the sexiest thing I had every seen. That led, of course, to another hard on, which she admired, complimented, and touched for a minute or so, then took in her mouth, and received another load of cum, which she seemd to have no difficulty swollowing. Eventually she had me calmed down a bit, and proceeded to show me how to kiss her, how to touch her boobies, how to suck on her nipples, how to touch her between the legs....who knew that such a perfect thing as a clittoris even existed?....... how to kiss her between the legs and tease that magic little button, and in due course how to put my cock into her. It took the rest of the afternoon, and more than half a dozen erruptions from my cock, but finially she had the first orgasm I had been around for a lady to have. She had two more before I left that evening. I wasn't a virgin per se, and my hands had been a few nice places, but this was the first woman, who really wanted sex, who knew what they wanted and how to ask for it, who I was really naked with, in a private place. It was a revelation.
As it turns out, it took quite a few subsequent days for us to "go through the attic, and later the basement", and almost every day of work involved another "lesson" from her, including the use of a condom.....who knew that ladies could get pregnant from fucking? She fortunately couldn't anymore, but she taught me that important lesson too. Who knew that there were multiple positions for fucking? Her favorite was riding atop me like I was her horse. I learned later, that I was her first lover after she lost her hubby, so she was as "hungry" as I was. Only later was I to understand that she needed a physical release without committment, so I was perfect for her at the time Ultimately, the house was cleaned out, and she moved, and I didn't see her any more. But, she left a memory of the still vital, somewhat older woman (maybe with boobs that had just a bit of weight, a waist that was just a little thick, that had a bit padding on her bottom), that taught me to treat a lady right in bed.
I didn't realize it at the time, but over the next few years, a surprising number of similar aged ladies needed "things moved", that was my regular weekend and summer "job", and I wound up in bed with several of them. It took me until about the time I finished college, and went off to professional school......that one of them got to talking, and from an off-hand expression, I realized that I had been "passed around", very discretely, by a circle of friends who had lost husbands, gotten divorced, or were just looking for a nice safe "side dish", and that hiring the neighborhood "boy" was an excuse to get stuff around the house done, to enjoy looking at and touching sholders, arms, legs and, of course, a tireless cock, with an increasinng knowledge of how to treat a lady. I did not feel "used", I felt grateful.
Anyway, if others have stories, or pictures, of encounters like this, feel free to add to this string.
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