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.

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.

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.

No Stories, but Envy
 

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.

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

Here's Ellen, minus the blonde pubic hair,

More?
 

She looks like my first girlfriend. lol.

{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 :(

Karlhein's story
 

Please finish your story

My second relationship was with an 15 years older woman. I was 22 at that time when we met. A year and half later we got into a relationship.

She is a widow and have 2 kids that I never met. She lived temporaily with her co-workers. She is a beauty and some guys in the company we work with (we were both in-house contractors) would try to hit on her. She has slim figure with long legs which I prefer on women.

Weirdly to say, she was my first blowjob. When she felt and confirmed it with me, she made sure to do it everytime we had sex and even allowed me to do a facial on her one time. Obviously, her experience on sex taught me a lot but I liked her openness to some of my sex/naked bucket list. I managed to influence her to have sex on the beach but we ended up both not liking it and almost got caught lying naked on the sand. The best moment I will share on a separate post.

The relationship lasted for almost a year until some weird scenario happened. I got reassigned far away then lost my phone. I went back to visit 6 months later and her company got replaced due to cost cutting.

Here's for you Jellyman

She grabbed my cock, and pulled me over to and up the stairs, saying eat me, fuck me, make me cum, again and again and again. The upstairs of her house was well appointed, well made up, with soft beige carpets, Her bedroom was big and airy, with a huge bed. She plopped down on her back on the bed, her legs, and the wet pussy between them, pointinng at me. I kneeled between her legs, leaned over her, and began to kiss her. Her tongue was lively, probing in response to my probing. I was laid out full length on top of her, I could feel the wetness of her pussy with the head of my cock, which was pressed up against her.

She pushed on my shoulders, pushing my head down, first to her tits, with those marvelous nipples, then to her flat stomach, then to her nearly hairless mons, then to her pussy, which already had a wet spot of the bed beneith it. She opened her legs wider, causing her pussy lips to open, I pulled back to admire it's pinkness, and the little head of her clitty peaking out. Lowering my head, I began to lick up the length of her slit, from nearly her asshole to over the head of her clit. Shhhhhhhhiiiiiittttt......oh god, that feels good, don't you ever stop. As instructed, I continued the long slow, deep probing licks up her pussy. Oh, shit, oh shit, oh shit, suck my clitty, suck it hard. I did, and it got noticeably bigger and more protruding. I put my hands under her hips, and pulled her pussy up to me, and she started shuddering, and moaning, ohhhhh, ohhhhhh, ohhhhh shit, I'm cumming, and she flooded my mouth with her secretions, drenching both my cheeks and the sheets, her hips bucking up against me. I held on, and continued to suck her clitty, for a couple of minutes, while she orgasmed.

Eventually, she calmed down a bit, saying kiss me softer, let me catch my breath, pleeeaaase, oh yes, oh yes, kiss softly, come kiss me, I slid up her body, kissing mons, tummy, nipples, neck then mouth. Eventually she caught her breath, saying, I haven't cum like that in 20 years, and that was an affair shortly after my hubby lost interest in fucking. And eh was a young guy too. I can't wait for you to put your cock in me. But, first I want to go 69 and taste your cum again, and get you to where yuo can fuck for a long time.

We rolled over, into the 69 position, her on top, her nearly hairless pussy 2 inches from my mouth, her starfish level with my nose. I felt her take my cock in her mouth, and began licking her slit from clit to the edge of her ass. As I licked, she began to squirm, she lifted a bit and I could see drops of her secretions hanging from her pussy lips.
Using my fingers, I pulled her bottom open, and used my middle finger to t e ace around the edges of her starfish. Her ass began to wink at me as she neared cumming. I pushed my finger into her ass, first to one knuckle, then to the second knuckly, and began to fuck her with my finger while sucking her clitty.

She began to cum, her ass gripping my finger as fluid poured into my mouth.

Thank you Karlhein
 

Do you have anymore pics of her?

In her mid-40's, on the deck of a cruise ship I watched as my then-girlfriend now-wife gave two young (just turned 18) men a very graphic and explicit lesson in female vaginal anatomy, demonstrating with her finger what they should do with their tongues once they found their own girlfriends.

Something none of the three of you will ever forget.

Would love to hear the long-form version of this story!

Early 70s as a young boy when it was normal to get washed in the kitchen sink, mother yelled when i experienced my first cigar as she washed me, father respnding to her yell and viewing the situation declared from now on ill bathe myself, i miss the kitchen sink .

As we relaxed, my finger still in her butt, she said, I've only done anal a couple of times, and it hurt, but I've never cum that hard before. What were you doing? Nothing special, just using my fingers. Would you like me to put my cock in your butt? Women who like anal, often really like anal. Ooookkkk, I'll try, but be gentle. Of course I will until you ask for more.
I got her flipped over into a butt up position, my cock naturally found the opening to her pussy. First, let's see if you like doggy style fucking. She did, and came several times. Eventually I had my thumb in her bum and my cock in her pussy. Eventually, I replaced my thumb with my cock in her ass, gently at first, then she started screaming...harder, harder, harder, and started cumming, and cumming, and cumming, draining all the juice from my cock.

It took up 3 weeks to finish moving, a nominally 1 week job. We only finished because he hubby cane back from Hong Cong, so we couldn't fuck the day away. She taught me how much ladies like to be appreciated, and how much the will tolerate young guys coming quick, as long they are happy to go again, and again and again. I also learned how to be gentle with anal virgins, some of whom are destined to really like anal. I also learned a lot from her, but also from other Mrs Robinson's that older ladies are often really multiple orgasmic. I "worked for her" often during the next 3 years until I moved permanently away from home.

You asked for it...
 

https://forum.oneclickchicks.com/sho...93#post2650593

I think the link goes straight to the photos, you'l;l have to scroll a bit upwards to get to the text.

She was in her forties at the time, so I think that qualifies her for this Thread.

[QUOTE= I think the link goes straight to the photos, you'l;l have to scroll a bit upwards to get to the text.

She was in her forties at the time, so I think that qualifies her for this Thread.[/QUOTE]

Thanks for the link to the story. Would love to find a smaller C/O cruise, most of the advertisements are for mega cruise ships.

One of the regular ladies who I did chores for, and moevd things for, was Mrs Derrick. She was the mom of one of my friends, and I had even had a few dates with her youngest daughter, we made out and I got to feel her tits but never even got my hands in her pants. Any way, the kids were grown, Mrs Derrick was 50, just divorced, anto move to a smaller house in a different city. She heard that I was "the kid who moved stuff". I suspect, but don't know for certain, that she also heard from some of the neighbor ladies (I had fucked about 15 of them by this time), that I was a good fuck, and she was getting to an age where between the divorce and her age, her opportunities for getting laid were diminishing. Anyway, she hired me to pack up things in her house, and then go with her to the new city, where she had relatives and a new house, to unpack. It was several days of really good money, so I didn't care if I got to fuck her, it really covered my savings for college. She wasn't the kind of woman with the body of a 30 year old, sort of an aging face and a bit of a dumpy body, and I had no previous experience with her, so I wasn't going in with any expectations.,

The first three days at her house in my city, I worked my butt off, packing boxes, taking stuff out to the trash, moving furniture to friends' houses. I was sweating all the time. But, I was wearing cut off jeans .and half the time wasn't even wearing a shirt, as it was hot. BTW, I had been a high school football star, and was playing quarterback for a D3 college, so I was 6 ft 1 inch of muscle, probably easy on the eyes for a lady of a certain age". I noticed, midway through the first day, that she would occasionally be staring at me, at my arms and shoulders certainly, but also at my shorts, which held a very nice 7 in + "package". She didn't know it at the time, but my dick also had a very large head, tended to point very high, and could recover quickly. Also, by that time, between a few willin,g girls at school and quite a large number of older ladies, I was experienced enough to last quite a while when my dick got wet.

By about mid afternoon on the first day, she was bringing me lemonaide, and finding excuses to touch my arms and shoulders, then, after helping me pack up so me "frilly" clothes she went in to change, and came back in a peasant blouse (under which there was clearly no bra) and some fairly short shorts. She wasn't exactly Bo Derreck running on the beach in "10", but she was clearly a woman showing off a bit, and by then I knew enough to know that ladys liked to be politely noticed, so I said "wow, Mrs Derrick, you look nice, that blouse suits you well". She blushed, and got a big smile on her face, and said "I'll bet you say that to all the girls", and I said "well, it's true". She was actually beaming at this point. We went back to packing boxes, but she insisted in bringing clothes (bras, panties, nighties) to the boxes and putting them in the boxes while I sealed the boxes. This meant that she was bending over a lot, which with her peasant blouse and no bra meant that I was looking down her blouse for 30 seconds of every minute. Who can turn down a downblouse, even from a 50 year old lady. Her boobs swung free and were sort of pendendulous, with pointy brown nipples. As we went on, it seemed like her nipples got progressively more pointy, and it seemed like she progressively took more time toI got a bit mesmerized, and got to staring, and she played the game of suddently looking up, smiling broadly saying " why yes, Mrs Derrick, I see that you have very nice tits, I really like looking at them, and am thinking what they would feel like if I touched them. Do you like to have them touchedd?

She got a big smile on her face, then sort of a dreamy look, and said, "it's been so long", "I used to be able to cum, just from my hubby sucking them, and my pussy even got wet when I was nursing my babies, that's why we had 3 kids in very close succession, I wanted hubby to fuck me every time I nursed." "But, the last several, maybe 10, years, he's hardly touched me. I got a little fat, and my tits sagged quite a lot and, well, I think he had several affairs, so I've played with my own pussy, and pulled on my own nipples, at least for the last 10 years, and I have half a dozen vibrators, sometimes I use 3 of them at once....mouth, pussy and ass.. So, yes, I like to have them touched, and sucked, and even bitten softly, and I can cum and cum and cum. But, hubby isn't interested any more, and is fucking his secretary, who has perkey tits. But, he's also getting a bit of a limp dick, at least he was the last time he tried to fuck me, so good riddance to him. She paused a minute, still bent over where I could look down her blouse, and looked directly at the front of my shorts, and said, "now if I could just find someone who likes to fuck, but doesn't need a 10 to get excited, and can last more than 5 minutes. Hmmmmmm, do you know anyone like that?
y
I stood up, unbuttoned the button on my cut off jeans, and let them drop to the floor. My cock was already hard, already aimed upwards tward the ceiling, and asked her "might this work for you?" She stared at it, swollowed
couple of times, said it's magnificant, please tell me that you want to fuick me." I said, I think my cock speaks for me, I want to make you cum and cum and cum. Do you want my cock?" With that, she reached out, put her hand around the girth of my cock, and brought to her mouth. She didn't try to tease it by licking or biting or anything, she just swollowed itwhole, all the way downd her throat in a single motion. She began to jack it, and tongue kiss it, and deep throat it, with intensity and purpose. She took a quick break, saying cum in my mouth, you'll last longer when we fuck, I want to taste your cum. Then, she went back to sucking, hard and wet and deep, until I filled her throat to the point where my cum began to run out of the sides of her mouth, even though she was swollowing as fast as she could.

Bosses Mistress
 

When I was in my early twenties, and in-between wife no.1 and wife no.2' have to admit I slept around a bit, partly as a reaction to the failure of my marriage.

At the time I was working for a food processing company managing their stocks etc. etc., and spent some of my time in Scotland where they had a second production plant (the other being in my hometown in England).

While I was there I spent a lot of time with the Branch Manager, and it soon became apparent that he was sleeping with one of the women, Julie, that worked in the office. It was not unusual for me to go out in the evenings with the two of them, and another younger girl, Anne, from the office, who was there to keep me company.

After I'd been there for a couple of weeks my manager went off on holiday for two weeks, with his wife and children, and I was effectively in a strange town where I really only knew Julie and Anne. So it felt normal to arrange to go out with them, as usual, over the weekend. However Anne was competing in a Scottish dancing competition on the Saturday, so it ended up with me and Julie going out.

It's fair to say that we were very merry when we got back to her home, and she invited me in for a "coffee or maybe something stronger"

It was at this point that I found out she was married, as her husband was sitting watching Match Of The Day - I guess the question of her being married and cheating on her husband with my boss.

One drink led o another, and after MOTD finished hubby went off to bed, while Julie made a coffee to sober me up before my walk back to the hotel.

When she came back into the room, she had unfastened a couple of her blouse buttons, and she sat down next to me. I was staring down her blouse like a dog on heat and she took hold of my hand a placed it onto her leg, just below the edge of her skirt.

It was at this point that I realised that she was expecting more from me than pleasant company, so I slid my hand up her legs, and quickly found she was wearing stockings. My hand slid between her thighs and cupped her pussy, while I pulled her head towards me and kissed her. Everything got a little blurry after that, but suffice to say that within a couple of minutes my trousers and underpants were on the floor, next to her blouse, bra, and knickers, while my cocktail was pumping in and out of her very moist, married, pussy.

We were on the floor with me on top, but she wanted to control everything and we rolled over and she rode me hard before coming for the first time. Rut that wasn't it. She took a little time to settle down from her orgasm and then she started to ride me again. Needless to say it wasn't too long before she had me right at the edge, and tipped me over in to an explosive climax filling her wet and wonderful pussy with my spunk.

We laid there together for a few minutes then she just said, very manner of factly, "Well that was good, but don't think it will happen again, and don't tell anyone, especially our boss.

And I never did.

Suffice to say that the adventure with Mrs Derrick continued for 2 more days at her house (as we packed up) and 4 more days at her new house as we unpacked. We could have probably worked faster, but kept getting distracted. She was massively responsive (which is what I really like), and the fact that she was mid 50's and a little thick in the waist wasn't off putting: nipples, giving oral, receiving oral, fucking, toys, I was even her first anal adventure. I never did find anything she didn't like.
She really liked how fast I could recover, and my relatively good "endurance" in the saddle.
And, I even got paid for all my work, and subsequently got invited to visit the new home a couple of times to "help her settle in".
Such a deal for a stupid kid who's only real skill was lifting stuff!

????
 

You mean who teach little boys... because if men need teaching, that means they only have sex w hookers ho will fuck anything for money...

Respectively disagree.
1) I've never used a hooker, so I missed that experience.
2) I had the good fortune of experiencing several Mrs Robinson types, who just wanted some sex, and I was either attractive enough or capable of being treated as an adventure rather than a committment, and taught me a lot about pleasing a lady, mostly getting past the "being too fast" stage, and learning how to wait for her to have her pleasure. I know that I'm a much better lover for their teaching.
3) while young, i was never a "little boy" (legal age and not a virgin) when i started experiencing Mrs Robinsons. 4)Maybe you don't enjoy the stories, but they come from a very good part of my experience as a young man. I thought the group might enjoy them.

karl
 

Charis
 

See my response to Karlheim above.

Mrs Manheim was another Mrs Robinson in my experience. She wasn't the prettiest lady, was rather rotund, however she had very large boobs and her nipples often poked her shirt front out. But, for her lack of physical charms, she was very sweet, very funny and very flirty. The first day I ever worked for her, she was grabbing my arm, and pressing her boobs against it, over and over again. She kept a couple of buttons on her shirt undone, but even though I couldn't see fully downblouse, I could see a lot of very nice cleavage.
Near the end of my first day of work, she really grabbed my arm, and rubbed her tits against me, and said, you really know how to distract a lady. I replied, looking directly at her boobs, that wha she was doing made it "very hard" to work, and took my mind off the job. She smiled broadly, leaned up to kiss me, and said would you like to have a look, and maybe leave a deposit? As she said this, her hand stroked my cock, it feels like you are "full".

I kissed her back, and reached down to unbutton her blouse. Her tits were really substantial, the nipples poking through her thin bra. She said, I want you to suck my nipples, and cum on my tits. The feel of sperm on me, makes me so wet.

And so, with her hand and mouth providing encouragement, I placed a nice sized deposit on her titties. Afterwards, I reached down into her pants and found a very wet and slippery pussy, I think she was excited. Ifor her a few other times, always managed to cover her tits, and some of her fa.e, with my seed. Always found a very wet pussy afterwards, but she never wanted to fuck, guess that was "the line" as far as cheating on her hubby was concerned, but I'll bet he got the advantage of me warming her up.

It's easy to write stories about specific encounters with Mrs Robinson types, the somewhat older woman who sort of seduces you, and fucks your brains out. I've had my share, and then some, with Mrs Robinson, part of the best of my life.. But, are there general principles to make this more predictable, and more likely to satisfy her?

She wants to be wanted. Either hubby isn't doing it for her, or she's divorced, or maybe she's now a little less than Stifflers Mom. She still needs wanting.
The best thing you can do is bring a really hard dick to her, I think that women want hard dicks, it's mother natures way of telling her she is wanted. Maybe you should play with your dick looking at and touching her, and encourage her to touch herself. Maybe you cum too quick, young guys do, but she won't care as long as you get hard again for her.
She already has the power in the relationship (I was the college kid who moved stuff, mowed the lawn, and cleaned the pool, but I did have good arms and tight buns. She money, I was just the neighbor kid working for her. She's probably more experienced than you sexually, but she is beginning to lose her youthful charm, and her titties sag just a bit. But she's heard of things she may not have tried.....group sex, anal, toys, multiple orgasms, facials. But, you have a cock that will like her, even if she's no longer a 10, and not get bored with her like hubby did.
She can control the narrative, bring in multiple guys, bring in her girlfriends, she's more likely to leave you than you leave her, she doesn't need anything from you more than a hard cock, and willingness to wait for her to have one or more of the 37 daily orgasms she is entitled to. Remember, everyone jacks off, what else do you think vibrators are for?
What she wants is someone to notice her and whos' cock will get hard for her, and spray all that sticky stuff just for her.

I think this explains why women want 2, or more, guys at once. More hard cock that finds them attractive.
I think this explains the fascination with BBC. Yeah, cultural taboo, but yes they tend to be big, and they also tend to be really hard.
I think this explains why she's hooking up with you in the first place, it's surely not because you run the bank. She wants a hard cock, period.
I think this explains why putting her hand on your cock while you are making out is so effective, it shows her how hot she is making you.
I think this explains enjoying blow jobs, facials and cum on her tits, it shows she is making you hot. She's already got birth control figured out, and how to protect herself from STDs, while you may not even really know yet that fucking leads to babies and can't spell herpes.
I think it explains why Viagra is popular, it makes soft cocks hard, and that pleases the lady. It's not about the guy feeling better, it's about the lady feeling that you want her so much that your dick is nearly exploding just for her.

So if you are blessed with a big cock, fine, Mother Nature has been kind to you. Better to be blessed with a cock that stands high and points above the vertical, it tells her she is making you hot. Better yet, if you can cum multiple times, and give her time to cum, which doesn't require freak anatomy, Mrs Robinson will enjoy you, and teach you stuff.
.
Some evidence.

More thoughts about MILFs and Mrs Robinson, and all the delight they can bring. Although we all think about the perfect Mrs Robinson, there aren't many women out there as attractive as Jennifer Cooledge, the first official MILF on film. But, don't set your standards too high. Everyone wants to hang out with really hot women. Beyond it's inherent pleasure, like touching a piece of art, the more "average" Mrs Robinson often brings unexpected joy.

She's likely grateful, probably can't get pregnant, doesn't need your money. What she needs is some attention, and if you also give her a hard cock, that's all the better. She's probably more open to being fucked by you and a buddy, she's probably more open to sharing one of her girlfriends with you, she's probably more open to having her butt filed, and a load dropped on her face or tits, she's probably more open to some really nasty conversation, she may be more open to having sex in more "risky"circumstances. She's more likely open to having you only once, or a few times, she expects that you will move on, but she will enjoy the time she has with you. If you can get past a few wrinkles or a few extra pounds, or tits that sag more, you are more likely to find a multiorgasmic screamer, which for me is the sine qa non of sex partners.
How do you find her? Look for laughing eyes. You're always going to make good eyecontact, and be pleasant. If she has lauging eyes, and if she iniates the flirting, be classy, put push the boundries, she's likely telling you she wants to get laid. Eve the older women, especially the older women with older hubbies, they may want to fuck you while hubbing is watching. Never assume she's not interested. If she shows skin, low cut dresses, downblouses, giving you squirrel shotes, if she iniates the touching, if her eyes laugh, if she and her buddes flirt with you, you might get more than one pussy at a time, bottom line, pay attention to the ordinary, sometimes a little mousy, sometimes a little too thin or too heavy, with laughing eyes....your cock just might get a workout.
Some evidence

when i was single and polyamorous i enjoyed many men who were older than me but also some who were younger. when i was about 25 i was watching some college guys playing ultimate frisbee. i got to flirting with one guy. it turned out he was 18, so we couldn't go have a drink together and somehow we ended up in his dorm room. he had a great sense of humor and i was laughing so much and the next thing i knew i was naked and teaching him how to lick a clit. ;) i sucked his cock for a while but i wanted to fuck, so we did. he got worried that his roommates might come back, and i told him that if they did i would just get dressed, introduce myself, give him a kiss, and leave. lol

they didn't, so we had time to linger. it felt hot to be the almost-cougar. ;)

emily

Maybe this is just a version of "I'd fuck that", but recent posts have me thinking of who I would fuck amongst the Mrs Robinsn set. In the lower right is sort of an idealized woman for me, perfect build, perfect smile, the kind that makes my dick get instantly hard. Sadly, the kind of girl who is pretty hard to attract, and too often is very enthustiac in bed. I've "been there, done that" but too infrequently, and often a little disappointed. She wants what I "can give her", beyond multiple orgasms.

Then, I went through one of the "older ladies" strings on OCC, and picked out "yeah, I'd fuck her". I'll bet she is more likely to have several important characteristics: "laughing eyes", her hitting on me, having multiple orgasms, and to not be frantic if it was a one time adventure.

There is commonality. She's mostly pretty, and was probably a hottie back in the day, mostly fit (although sometimes a little padding can be nice), still mostly has round boobs, but a certain sag is not bad if the "laughing eyes" are there, for the most part has a very well trimmed or bare bush.

In any case, if you ever find a pretty, older lady who is friendly and touchy, and has "laughing eyes", pay damned close attention and flirt back, you are likely to get the best fuck you ever had, and learn things about pleasing a lady. Even if she's not exactly young or still a 10.

More of the ladies that might be a much better fuck than the 10 you just saw on the beach. And......she's more likely to say "cum on my face" or "put it in my buuutttttt" or "can I bring my friend along?" or "do you have a friend you could bring along" Reference hotty from the beach is lower right.

I've had my share of Mrs Robinson types. It started just before I went off to college. I was the local kid that "moved boxes, mowed lawns, cleaned pools", I had a strong back and a good work ethic, so I got busy pretty quickly.
The very first was "steadying my leg" while I was up on a ladder, then she steadied my butt, then my cock, and then fucked the shit out of me.
But, most of the rest were more subtle. The most common scenario was leaving a button undone, or wearing a low cut top while she bent over and "helped me with boxes". Guys will look down any blouse, I've been doing it since before my dick got hard. I now think that most ladies know exactly what they are showing off, but leaving a button undone or bending over gives them plausable deniability. It does seem that they like to give you a good show of their titties, then suddenly "catch you" and ask something like "enjoying what you are looking at?". Fortunately, I kept my mouth shut until I got caught, had enough sense to never make the first move, just enjoyed the show, and said "yes mam, you have really nice breasts" when they spring their trap. My dick was usually tenting my shorts by that point, so they took charge of things and taught me stuff about pleasing ladies. That usually led quickly to full bore sex, and to things I had never done with the girls in high school.. I guess I was good enough at it, and at moving stuff, that I stayed busy.

A few others would be in a swimsuit, and wound up showing off their goodies, nominally unintentionally (yeah, right). A very few just "did a sneak attack" and showed their tits or even pussies to see what I would do. All of the repeat ladies were pretty open once we had done it, but the first time, they mostly tried to tease me, and catch me......I loved it, and even if they didn't play that game, I saw a lot of titties.

Remember, Mrs Robinson is running the game, you can't seduce her like you are trying to do to her daughter or grand daughter, she wants sex (your hard cock) on her terms, so don't try to develop a romance or relationshp with her, if she wants your hard cock again then she will let you know.
Although some are divorced, there are more who are married to boring old guys who don't fuck them enough or well enough. My impression is that they want you for limited functions, not as husband who can't support her. In any case, if you play the game her way, you will get some really good fucking, and maybe she will refer you to her friends.

Ms Robinson
 

Great story, tel more.

My main access to Mrs Robinsons, all all their carnal desires was from working at their houses (the kid who lifts things, or mows the lawn or cleans the pool). It was a reliable method for me to get laid by a nice lady, perhaps past her prime physically, but skilled and insatiable sexually. And I didn't even have to spend money that I didn't have on "dates". But, there was an antecedent, one my parents got me into, without thinking of my sex life. As far as they knew, they were just forcing me to learn the social skill of dancing. They were members of the local country club back in those days. That meant access to the pool (lots of swimsuits with the occasional boob on display), the tennis courts (a sport you could play with the teenaged girls, or their moms, or even their grandmoms). If you don't want to be hyper competitive, it's a good tool for seduction. But most of all, it meant the occasional dance put on by the country club. More by accident than design, I realized that: 1) women dress up, and you can often see her tits on the dance floor, whether she is your high school classmate, or her grandmother. 2) you get an acceptable reason to put your arms arou nd a woman, and to rub up against her, which feels good. And 3) number 2 often leads to her getting excited, which helps your dick. So, my advice to any young man, is to learn how to do social dance (the kind where you put your arms around women) well. You have to have good manners, and you have to "follow her lead" relative to the contact getting hotter, but believe me, you will see lots of tits, feel lots of nice bodies, and get laid with regularity.

I can’t remember if I’ve mentioned this person here before. Her name is Iris, a girl I secretly had a crush on for a long time. It was back in college. Iris was a friend of a friend, and I first noticed her simply because I said, “She’s so hot.” At the time I didn’t think much of it, because Iris already had a husband who loved her and a cute newborn daughter. That was that.

This story takes place four or five years later. Iris had gotten divorced. She was renting a place on her own and working hard to make ends meet. I also hadn’t been in a serious relationship for a while. So a mutual friend asked me if I wanted to give things a try with Iris. My initial thought was that she was four years older than me and already had a daughter. I wasn’t sure if I could handle that. But my friend said, “How will you know if you don’t try? Maybe she’ll be the one who isn’t interested in you.”

So we started dating. One time after I dropped her off at home, we kissed in the car. That night I realized how much I fucking wanted her. So I called her again, then drove back to her place. We stayed in the back seat of my SUV talking until late into the night, kissing and touching each other the whole time.

Eventually the conversation turned to blowjobs. Honestly, I had never really been a fan. My first girlfriend wasn’t very skilled at it, so the nervousness I felt during oral usually outweighed the pleasure. Plus, I’m someone who really loves kissing. I hate the idea of a girl’s mouth being used for anything other than kissing me. Of course I told Iris all of this. She just gave me a wicked little smile. Then I watched her pull the hair tie off her wrist, tie her hair up, and proceeded to give me a complete education with her skill and experience.

That was the first time I truly understood how amazing a blowjob could feel. The way her tongue and lips worked together, and the occasional suction that created a vacuum sensation, was incredible. That night I lasted less than five minutes.

Unfortunately, my story with Iris didn’t have a proper ending. or rather, we never managed to really get started. Even now, I still occasionally think about her beautiful figure, and the mind-blowing oral skills she showed me that night.