Older Ladies Who Teach Us to Be Men

[Nudebeachlover22]

[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.

[karlhein]

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?

[karlhein]

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.

[WoodyWoodWood]

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.

[karlhein]

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!

[GRITS]

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...