Older Ladies Who Teach Us to Be Men

[karlhein]

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.

[indym]

Great story and I'd love to read more.

I have a few that I'll write up when I get a chance. One involves a lady that was probably 15 years older than me (me being 18, at the time). She worked at a big retailer and was friends with a mutual group that I occasionally hung out with. She slipped me her phone number while we were at a group gathering (she was with a date), and we had quite a bit of fun together. One very interesting time was getting a hand job under a crocheted blanket while her teen daughter (she had her driver's license, so she was 16 or 17) sat across the living room from us. The mother slowly jacked me like nothing was going on, but the daughter had to know what was going on. I'll type up a more complete story later, but things ended when the mother wanted to get really serious...which was completely ridiculous and I'm glad I didn't go along with that.

Another was a lady (20+ years older than me) that worked at the same company my father did. I worked there during the summers (the company would temporarily hire employee's college-age kids), and I somehow learned about a lady that was having an affair with a permanent employee. For some crazy reason (ok... I was a horny kid), I started flirting with the lady, and she eventually came by my apartment to help me decorate or something like that. I ended up fingering and going down on her that visit, and that started a few times a week visit from her that lasted 6 months. She was a shift worker and would come by my apartment before going home. At that point in my life, I could last a long time, and I would do my best to wear her out :-). There was 0% chance that she would become pregnant, and I completely enjoyed every minute of my time with her. I'm putting this here so that I remember to write about it (if anyone is interested)... My mother was mad at me for something and came to my apartment to give me grief. My mother had a key and walked in on me balls deep in my friend (closer to my mom's age than me). It was a one-bedroom apartment, and I lived by myself, so the bedroom door was wide open. My friend was semi-out of her mind from fucking, and I was just climaxing as my mom spoke up. I half came in my friend and half on her spread eagle pussy as I was pulling out (with no idea who was behind me). My mom gave no ground and got to see her baby boy's cum covered cock and some lady's cum covered pussy spread eagle on the bed. It seemed like it took my friend 30 seconds to realize I had stopped and drop her legs. My mom never said a word about it, and my friend was afraid to leave my room (LOL).

For some reason, neither lady enjoyed giving a blow job, and they were both reluctant for me to go down on them initially. Maybe it was their age (this all took place in the early 90s) or some type of stigma they had, but they were both fit and nothing that they should have been concerned about. They both could come multiple times when I went down on them, so they certainly enjoyed it as part of our normal routine.

[karlhein]

Late in HS and throughout college, I worked periodically near my home, as the "kid who moves things". Mostly it was boxes, or stuff on the lawn, but occasionally it was the middle aged ladies who wanted something moving between their legs. I figured out later, that I was actually "passed aroung" within the neighborhood, but I never felt used, and indeed I learned a lot about pleasing ladies from the experience. Plus, it paid pretty well, better than working at the grocery store.
On one particular day, I was called to the home of an slightly older (55ish) lady, who wanted to reorganize how things were stored in her basement. She was thin, sort of pretty, with a very slim figure, dressed in sort of a frumpy zip up housedress, as she planned to help and didn't want to get her good clothes dirty. Her hubby was an older banker, on a trip to Hong Kong, their kids were grown with their own families in a different part of the country.
The plan is that I would move the boxes, or make space for the boxes, and she would often sort of move them into final position, or start the process of moving them from where they were stored. As a result, I got a lot of views down her housedress. I hadn't thought much when I first met her, but she had small, nicely shaped tits, with long pale nipples, consistent with her blondish hair and fair skin. I began to position myelf to her side, to get the best possible view of her boobs.
One time, she took a long time to get a box strarted for me to move out of the way, and I got a bit mesmerized, as I could seen the shape of her aereola quite well, and was beginning to wonder if I could see even further down her dress, and was that a hint of her bush that I could see. Anyway, I finially looked back up, and she wasfo looking at me, with a big smile on her face. She asked if I saw anything I liked? To which I repliied that I certainly did. This game had been played on me before by other Mrs Robinson types, so I knew I would get either a mild scolding, with the admonition to pay attention to business, or asked if I wanted so see more, so I smiled back, and said, that she was quite an attractive lady. She got a very big smile, and said, I hoped you would like it. I like that tent that seems to be growing in your shorts.

I was in running shorts and a t shirt, I also have a slightly harger than average cock (7"), with a very big head, and the whole thinkg stands up high when I get excited, so there was a definite tent in my shorts. If you will drop those shorts, and show me yours, I'll unzip this dress and show you mine. In about 3 secconds, my shorts were at my ankles, and I was stepping out of them. As I stoood up, the head of my cock agled up to look at her face. She short of startled at the sight, saying, my my my, I haven't seen anything sand up that well in a lot of years, maybe ever. Can I touch it? She reache out with her hand, grapsing it underhanded, jerking is up and down. As she was doing this, she bent forward, so she could look at it closely, and opened he rmouth and bicked the underside of the bulbous head, just where a guy is most sensitive. And it erruped all over her face. Her mouth was already open, so she got the third, fourth and fith spurts in her mouth, but the first two went all over her face, from chin to hairline. As the spurting stopped, she pulled back, saying, oh my, oh my, oh my, I haven't had a shot in the face since I was in high school, oh my oh my, oh my, your cum tastes nice. Please tell me you can do that again. I want that cock in me again.
To be continued.

[PalmsMan]

Originally Posted by karlhein

Anyway, if others have stories, or pictures, of encounters like this, feel free to add to this string.

So, as a virgin, all I wanted was for a mature, confident, sexually aware woman to take me under her wing, and deal with my fumbling insecurities, and premature ejaculations. A woman to teach me, and turn me into a sexually knowledgeable, and confident, young man.

Alas I learned like most youngsters by fumbling my way through my first sexual encounters with girls my own age. You are, IMHO, fortunate to have had such a sexual mentor, I'm jealous. Now in my seventies I missed out on the "Mrs. Robinson" thing.

[karlhein]

I reached up and pulled on the zipper of her housecoat, all the way to the bottom. It opened, exposing her small boobs, with those marvelous pink nipples, her pale body, and her sparse totally blonde bush. I pushed it off her shoulders, leaving her totally nude. Pinching first one nipple and then the other, pointed up very hard on slighly deflated boobs, a shudder rand down her back, she closed her eyes and sighed. I put my hand on her pussy, feeling the increeadible wetness of her pussy, I stroked my finger through her pussy lips, and found the little know of her clitty. She shuddered, put her arms around my neck, saying I want you to fuck me, but first I have to suck your cock again, and feel more of your cum on my face and in my mouth. Are you hard again?
I stepped back, said look down, he hard enough for you? Now, only 5 minutes after I had cum, my dick was fully hard, pointing up at her face, the big head seemingly ready to burst. Do you like hard cocks, ready to explode just for you? Do you want to taste it all, or to have it on your face again. She shuddered, said, oh my god, let me suck it, when you explode, I want to taste it all, and then have it on my face again. She knelt, grasped my cock, and engulfed the head, begining a rapid blow job, complete with licking my cock, running her hand up and down the shaft, and in stages taking more and more of it in her mouth, until she periodically deepthroated me. In only another couple of mintues, I was exploding in her mouth, she was shuddering, my cum was leaking out the sides of her mouth, and she pulled off, letting the last couple of spurts hit her nipples.

Shit, you really like that. Does giveing head really excite you? She gasped, you have no idea, I came when you came on my facce the first time, came when you came in my mouth, and came when you hit my nipples with that hast blast. Feel my pussy, I'm so wet I' m reeady to squirt. She stood up again, pulled my hand to her pussy, pressed herself against me, and put her tongue in my mouth. She was so wet that three fingers slipped into her pussy, I began to pull against her, to where one of my recent Mrs Robinsons had taught me the g spot was, and she started to breathe heard, to say oh god, oh god, oh shit, and came massively o my hand, filling the palm of my hand with her juice.
jo
As she calmed down, through a couple of smaller orgasms, she said, I've always been a sucker to a hard cock, that I know is there just for me. In high school, I was easy, was a blow job queen. I never even got fucked until my 3rd year of college, but I had over 100 different cocks in my mouth by that time. Sort of sadly, I fell in love with, and married only the 3rd guy to fuck me. He cooled off after 5 years of marriage, so the last 30 years have been sort of quiet. The last 5 years, I've had a few affairs, but non of them young guys, none with a really hard cock. I sure hope you are planning to come upstairs to fuck me with that cock of yours. I want you to eat my pussy, and let my cum fill your mouth, and I hope you can spend the next couple of weeks :healping with this basement", because I want your cock again and again and again.

To be continued

[karlhein]

Here's Ellen, minus the blonde pubic hair,

[raysallx]

She looks like my first girlfriend. lol.

[naturistwineboy]

{sigh}

If I could only go back and truly deal with that MILF. We had two periods of dating, first was about three years, second was about two years. We literally were too competitive in EVERYTHING. Sex, education, Golf, racquetball, everything. It's literally what ruined our relationship. We remained friends even after our breakups. one of my biggest regrets, she never met my wife that I met longer after we broke up. She unfortunately passed away way before her time