My YouthChapter 10 Caroline Part 2 Caroline s house
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Old Caroline Loves Helping Young Men free porn video
Not in her entire life did Caroline, a comfortable looking, grey haired and sensuous plump widow of nearly 70, ever think she would become a sex goddess! But , that is how her select band of followers described her!
The secret to Caroline’s late sexual popularity was born in her younger days when she discovered and really enjoyed steamy and sometimes unusual sex. She knew what turned her on and how to turn on men to such an extent that she began to only get really hot orgasms when she was in control. That approach had been very satisfactory for her and her two previous contented husbands.
Now she was a volunteer at a charity shop with similar older ladies and two unemployed young men who still lived with their parents. In her opinion they were just saddos. They were friendly and courteous and always took a very, what she thought was, an unusual interest in her appearance.
Unlike virtually all old ladies, Caroline took great care to make sure she looked smart with discreet make up, perfume, good hairstyles and whilst plump she still could not, and would not, stop wearing clothes tightly fitted – dresses, skirts, blouses, jumpers. Although overweight Caroline kept everything together with high class foundation garments which accentuated her bust and bottom.
One regular Thursday she chose to wear a jersey knit dress and although it clearly showed the outline of her girdle and suspenders, she looked good for an old un. And seeing the reaction of the saddos she was not wrong. So, being mischievous she decided to put on a show for her enjoyment.
In the back room making tea one afternoon, she took off her panties, undid a stocking, sat down and pulled up the dress to girdle suspenders and called “Peter can you help me please?”
“Peter, I am awfully sorry and this is very embarrassing, but I was changing this stocking as it had a ladder, but the arthritis in my fingers came back with a vengeance. Could you be dear and clip it to my suspenders”.
He kept fumbling with the suspenders but that was because his focus was her fat hairy fanny. Of course, Caroline, enjoying this admiration, even raised up her leg allowing him a better look.
“Oh Peter, you don’t seem to know what to do, do you?”
Stuttering, he responded, “Caroline, I don’t have much experience of ladies undergarments or women in general. I never know what to do or how to do it, so to speak.”
Coaxing him gently, Caroline found that Peter was and still is, influenced by his relatively religious upbringing and straight-laced parents which he added were an extra burden as he had to do more and more for them around the home.
“Oh that is a shame, Peter. You should get out more. There are lots of women who would love to meet a decent man like you”.
Peter then blurted out, “Could you help me Caroline? I don’t mean being my girlfriend or anything but, say, like an aunt who would help me understand what ladies like”.
“Me, I am far too old, Peter”.
“I don’t think so, I hope you don’t mind me being personal but we all think that you are smart and clever and dress and smell nice. Think of it as a nice aunty who wants to help her nephew”.
“Well, if you really think I can help you, you will have to do everything I ask, as it will make the lessons much more enjoyable. Are you happy with that?” Peter nodded and it was agreed that he would call round Saturday evening for dinner and a chat.
Saturday afternoon and Caroline was seriously thinking how best she could help Peter. From the stocking incident – although for her own pleasure – she knew he liked what he saw. What he lacked was confidence and when it came to fulfilling a woman’s needs, he seemed to be very naive. So there and then she decided to teach him for the good of womankind.
Around 4, she took a bath and a long-time selecting what to wear. To keep her size 18 nice and firm the white transparent open bottom all in one body former, with sheer 10 denier seamed nylons did the job. Pants, she thought, would only get in the way. Putting on a tight fitted deep V neck cashmere jumper that highlighted her 34 DD beauties and conservatively shortish pleated skirt, she looked very respectable and... nice.
On the dot at six, Peter presented himself, with a modest bunch of flowers. Caroline gave him a tight hug and kiss on the cheek. “It’s lovely you came, I didn’t think you would.”
In the living room he replied, “Caroline, I have been really looking forward to this. Thinking about it I don’t know how you can help me really.”
“Oh I do, Peter. Now settle down over there and I’ll get some us something to drink – tea, coffee?”
“Coffee please, Caroline”
Seated opposite him in her comfy armchair and slightly raising her skirt, Caroline said “Peter, for me to help you I want to understand you and your life. You might think the questions rude but anyway here goes”.
She then asked him if he got a hard on when looking up her skirt. (Yes). How many women he has had sex with (only professional ladies once every 3 months this last year)....In all she asked about 20 intimate questions.
Moving across and next to him, Caroline, putting her arm around his neck and face really close, whispered, “ Peter, the first thing you have to learn, is how to properly kiss a woman. Let me be honest, I don’t love you or you me. But kissing is an art-form that women really do like. Now kiss me”.
He gave her a very brief peck on the mouth. Even that, was making his cock uncomfortable. But when she pushed her tongue in hesitantly pushed right back – slowly but firmly. She knew how to make men hot and after a good few minutes of increasing passion, she leaned away and looking at the surprisingly large bulge in his trousers, thought, that was a quick lesson learned.
Over the enjoyable dinner, and Caroline explained the details of petting. “Peter when we kissed, I saw your erection. Don’t be shy. By the looks of it, you have nothing to complain about down there.
But do you know that it also makes us ladies horny? That’s where petting comes in. There are many, many ways couples please each other depending on what they prefer. Normally, it’s a case of exploration and communication. Be honest, what do like doing?”
Peter, did not realise that she would be so blunt and was fearful of telling as Caroline might think he was perverted.
She seemed to sense this but knew her luscious fat hairy cunt held a clue. “Don’t worry pet, we can work around that for the time being.
Moving from the table back to sitting opposite, Caroline gradually pulled her skirt up and legs slowly apart, “Don’t look away Peter, look at this". You really do like looking at ladies undergarments, don’t you”? I bet you’ve never seen such a big hairy juicy swollen one as this. Well, that’s because I pumped it every day for 20 years and now it’s fat and very wet. Now, you show me just how big your cock is”
He took down his trousers and pants, allowing his very thick and rigid 8incher to spring up.
“Peter, now we are going to enjoy what I call visually stimulated wanking. Go on grab it and gently rub but don’t shoot your load as I want to show how to make a lady have a really good orgasm. So keep your eyes right on my fanny.
Putting her fingers around her protruding stubby clit she showed him the art of clit stimulation.
She was getting really worked up plunging three fingers in and out, and Peter was loving it. “Caroline, I can’t hold it much longer” and then a great wad of spunk shot from his circumcised dick onto the carpet. Caroline was not far behind. With sticky juice running down her chubby thighs, she let out a stifled groan and threw back her head.”
After cleaning up Caroline said “Peter, I’m really sorry if I shocked you but I had to get to let go of your inhibitions". Now tell me, what made you like seeing up ladies skirts in the first place”?
He outlined to her that as a only c***d he always was made to be present when his three aunties visited his mother. And up to about the age of 12 he often sat on the floor which gave him really good access to looking up their skirts and dresses. Seeing their garter belts, knickers or girdles excited him. He recalled that his aunt Dorothy was not so straight laced and over time, was all too aware of his ‘hobby’ and every so often when at the table, would deliberately open her legs to provoke him.
It got to such a stage that when he went to see her, she would often be dressed in just a dressing gown, which she allowed him to ‘accidentally’ see her bras and girdle. “And in those days, as women never bothered to shave, I was fascinated by her very bushy vagina”.
“Peter, there is no shame in that. Everybody and I mean literally everybody has one or two special sexual interests or fetishes.
Mine, are varied: number one is very prolonged foreplay. When my husband was alive we enjoyed role playing with lots of fanny and arse fingering, which kept us really horny...which incidentally, triggered off pumping up my fanny and his cock. And as you now know, I am exhibitionist – especially in public. Mind you I can think of several more things we could experiment with, would you like that”?
“Well that would be fantastic – see you next week”
One of Caroline’s fav role-playing scenes was based in a unisex hairdressers. She was the hairdresser and Peter was going to be the customer.
On his arrival Caroline was dressed (just) in short low cut white coat to show off her ample tits, and short skirt slit up the side. She stood by an upright chair and small table by the side.
“Peter we are going to play – the randy hairdresser. Imagine the scene, you are the last customer and I have locked the door so as not to be disturbed. You have always wanted to have your way with me but there has never been any previous opportunity. But today there is. You can say and do what you want to but it must be realistic. I’ll start”.
“Hello Peter, you’re lucky to catch me. I’ve had a terrible day, sit down.
Peter sat in the chair the protective cloth around him and her standing beside. He slid his hand up her skirt and fondling her fanny casually said, “Really Caroline, maybe this will cheer you up”.
“Opps, why Peter, how did you guess that is exactly what could cheer me up”
She placed her legs apart giving him free access. His hands roamed up and into her now damp cunt fingering he clit and then when under her girdle smoothing her large butt cheeks. She then gave him strong hints that her bottom was itchy and could he see to it. “Get right up there, sweet man”.
He didn’t take long to catch on. He hesitantly caressed her shit hole and then slowly pushed his finger up to his knuckle.
“Peter, how did you know that I am very sensitive there?”
By now, with his finger giving her arse a good going over, she knew that his raging hard cock would be in need of help, but she was not going to waste that 8 inches in wanking.
“Peter, you are really naughty but my bottom is getting sore”. Peter disappointedly took out his finger, allowing Caroline, to get her favourite lube from the draw.
“Now, Peter, I think it’s time I introduced you to anal sex – I am sure you will enjoy it. You see, honey, don’t be silly and think your dick won’t fit up here. It will, but first you must ensure it is really slippery. Let’s get undressed and I will show you.
Peter was naked in double quick fashion and it took just seconds for Caroline to take off the jacket and skirt. He thought she looked magnificent. Her lovely see through girdle and soft fat tummy looked great never mind her generous and shapely tits. “Will you take off your bra as well Caroline?”
Turning around, she said. “You undo me, then”. Standing close with his cock pressing against her girdle he unclipped it and gently rubbed them and rolled her nipples between this fingers. “Ah, that’s nice”, she sighed.
Passing him the lube over her shoulder, she bent down. “Ok big boy, lube up your cock and stick some up my lovely arse you’re looking at”.
Well, it was a really horny sight. Her big and hairy pumped vulva encased by her girdle, nearly had him shooting his load as he lubed up his cock. Calming down, he then got her arse nice and oily.
“No Peter, one finger is not going to get me really ready, put three in and make sure it’s everywhere. They slipped in and out easily.
“Now big boy, sit down and let aunty Caroline take over”. Straddling over him, she placed his dick into her shitter and pushed it all the way in.
“Fucking hell, Caroline, that is really tight” Seeing that he could also go to town on her tits, he really squashed and pulled her big nipples”.
Caroline was bucking up and down and wanked her engorged clit to the extent that she nearly passed out when she came. Then feeling his cum shoot right up her arse she slumped down onto his lap.
“Did you enjoy that you naughty boy?”
“What about you, aunty”.
The secret to Caroline’s late sexual popularity was born in her younger days when she discovered and really enjoyed steamy and sometimes unusual sex. She knew what turned her on and how to turn on men to such an extent that she began to only get really hot orgasms when she was in control. That approach had been very satisfactory for her and her two previous contented husbands.
Now she was a volunteer at a charity shop with similar older ladies and two unemployed young men who still lived with their parents. In her opinion they were just saddos. They were friendly and courteous and always took a very, what she thought was, an unusual interest in her appearance.
Unlike virtually all old ladies, Caroline took great care to make sure she looked smart with discreet make up, perfume, good hairstyles and whilst plump she still could not, and would not, stop wearing clothes tightly fitted – dresses, skirts, blouses, jumpers. Although overweight Caroline kept everything together with high class foundation garments which accentuated her bust and bottom.
One regular Thursday she chose to wear a jersey knit dress and although it clearly showed the outline of her girdle and suspenders, she looked good for an old un. And seeing the reaction of the saddos she was not wrong. So, being mischievous she decided to put on a show for her enjoyment.
In the back room making tea one afternoon, she took off her panties, undid a stocking, sat down and pulled up the dress to girdle suspenders and called “Peter can you help me please?”
“Peter, I am awfully sorry and this is very embarrassing, but I was changing this stocking as it had a ladder, but the arthritis in my fingers came back with a vengeance. Could you be dear and clip it to my suspenders”.
He kept fumbling with the suspenders but that was because his focus was her fat hairy fanny. Of course, Caroline, enjoying this admiration, even raised up her leg allowing him a better look.
“Oh Peter, you don’t seem to know what to do, do you?”
Stuttering, he responded, “Caroline, I don’t have much experience of ladies undergarments or women in general. I never know what to do or how to do it, so to speak.”
Coaxing him gently, Caroline found that Peter was and still is, influenced by his relatively religious upbringing and straight-laced parents which he added were an extra burden as he had to do more and more for them around the home.
“Oh that is a shame, Peter. You should get out more. There are lots of women who would love to meet a decent man like you”.
Peter then blurted out, “Could you help me Caroline? I don’t mean being my girlfriend or anything but, say, like an aunt who would help me understand what ladies like”.
“Me, I am far too old, Peter”.
“I don’t think so, I hope you don’t mind me being personal but we all think that you are smart and clever and dress and smell nice. Think of it as a nice aunty who wants to help her nephew”.
“Well, if you really think I can help you, you will have to do everything I ask, as it will make the lessons much more enjoyable. Are you happy with that?” Peter nodded and it was agreed that he would call round Saturday evening for dinner and a chat.
Saturday afternoon and Caroline was seriously thinking how best she could help Peter. From the stocking incident – although for her own pleasure – she knew he liked what he saw. What he lacked was confidence and when it came to fulfilling a woman’s needs, he seemed to be very naive. So there and then she decided to teach him for the good of womankind.
Around 4, she took a bath and a long-time selecting what to wear. To keep her size 18 nice and firm the white transparent open bottom all in one body former, with sheer 10 denier seamed nylons did the job. Pants, she thought, would only get in the way. Putting on a tight fitted deep V neck cashmere jumper that highlighted her 34 DD beauties and conservatively shortish pleated skirt, she looked very respectable and... nice.
On the dot at six, Peter presented himself, with a modest bunch of flowers. Caroline gave him a tight hug and kiss on the cheek. “It’s lovely you came, I didn’t think you would.”
In the living room he replied, “Caroline, I have been really looking forward to this. Thinking about it I don’t know how you can help me really.”
“Oh I do, Peter. Now settle down over there and I’ll get some us something to drink – tea, coffee?”
“Coffee please, Caroline”
Seated opposite him in her comfy armchair and slightly raising her skirt, Caroline said “Peter, for me to help you I want to understand you and your life. You might think the questions rude but anyway here goes”.
She then asked him if he got a hard on when looking up her skirt. (Yes). How many women he has had sex with (only professional ladies once every 3 months this last year)....In all she asked about 20 intimate questions.
Moving across and next to him, Caroline, putting her arm around his neck and face really close, whispered, “ Peter, the first thing you have to learn, is how to properly kiss a woman. Let me be honest, I don’t love you or you me. But kissing is an art-form that women really do like. Now kiss me”.
He gave her a very brief peck on the mouth. Even that, was making his cock uncomfortable. But when she pushed her tongue in hesitantly pushed right back – slowly but firmly. She knew how to make men hot and after a good few minutes of increasing passion, she leaned away and looking at the surprisingly large bulge in his trousers, thought, that was a quick lesson learned.
Over the enjoyable dinner, and Caroline explained the details of petting. “Peter when we kissed, I saw your erection. Don’t be shy. By the looks of it, you have nothing to complain about down there.
But do you know that it also makes us ladies horny? That’s where petting comes in. There are many, many ways couples please each other depending on what they prefer. Normally, it’s a case of exploration and communication. Be honest, what do like doing?”
Peter, did not realise that she would be so blunt and was fearful of telling as Caroline might think he was perverted.
She seemed to sense this but knew her luscious fat hairy cunt held a clue. “Don’t worry pet, we can work around that for the time being.
Moving from the table back to sitting opposite, Caroline gradually pulled her skirt up and legs slowly apart, “Don’t look away Peter, look at this". You really do like looking at ladies undergarments, don’t you”? I bet you’ve never seen such a big hairy juicy swollen one as this. Well, that’s because I pumped it every day for 20 years and now it’s fat and very wet. Now, you show me just how big your cock is”
He took down his trousers and pants, allowing his very thick and rigid 8incher to spring up.
“Peter, now we are going to enjoy what I call visually stimulated wanking. Go on grab it and gently rub but don’t shoot your load as I want to show how to make a lady have a really good orgasm. So keep your eyes right on my fanny.
Putting her fingers around her protruding stubby clit she showed him the art of clit stimulation.
She was getting really worked up plunging three fingers in and out, and Peter was loving it. “Caroline, I can’t hold it much longer” and then a great wad of spunk shot from his circumcised dick onto the carpet. Caroline was not far behind. With sticky juice running down her chubby thighs, she let out a stifled groan and threw back her head.”
After cleaning up Caroline said “Peter, I’m really sorry if I shocked you but I had to get to let go of your inhibitions". Now tell me, what made you like seeing up ladies skirts in the first place”?
He outlined to her that as a only c***d he always was made to be present when his three aunties visited his mother. And up to about the age of 12 he often sat on the floor which gave him really good access to looking up their skirts and dresses. Seeing their garter belts, knickers or girdles excited him. He recalled that his aunt Dorothy was not so straight laced and over time, was all too aware of his ‘hobby’ and every so often when at the table, would deliberately open her legs to provoke him.
It got to such a stage that when he went to see her, she would often be dressed in just a dressing gown, which she allowed him to ‘accidentally’ see her bras and girdle. “And in those days, as women never bothered to shave, I was fascinated by her very bushy vagina”.
“Peter, there is no shame in that. Everybody and I mean literally everybody has one or two special sexual interests or fetishes.
Mine, are varied: number one is very prolonged foreplay. When my husband was alive we enjoyed role playing with lots of fanny and arse fingering, which kept us really horny...which incidentally, triggered off pumping up my fanny and his cock. And as you now know, I am exhibitionist – especially in public. Mind you I can think of several more things we could experiment with, would you like that”?
“Well that would be fantastic – see you next week”
One of Caroline’s fav role-playing scenes was based in a unisex hairdressers. She was the hairdresser and Peter was going to be the customer.
On his arrival Caroline was dressed (just) in short low cut white coat to show off her ample tits, and short skirt slit up the side. She stood by an upright chair and small table by the side.
“Peter we are going to play – the randy hairdresser. Imagine the scene, you are the last customer and I have locked the door so as not to be disturbed. You have always wanted to have your way with me but there has never been any previous opportunity. But today there is. You can say and do what you want to but it must be realistic. I’ll start”.
“Hello Peter, you’re lucky to catch me. I’ve had a terrible day, sit down.
Peter sat in the chair the protective cloth around him and her standing beside. He slid his hand up her skirt and fondling her fanny casually said, “Really Caroline, maybe this will cheer you up”.
“Opps, why Peter, how did you guess that is exactly what could cheer me up”
She placed her legs apart giving him free access. His hands roamed up and into her now damp cunt fingering he clit and then when under her girdle smoothing her large butt cheeks. She then gave him strong hints that her bottom was itchy and could he see to it. “Get right up there, sweet man”.
He didn’t take long to catch on. He hesitantly caressed her shit hole and then slowly pushed his finger up to his knuckle.
“Peter, how did you know that I am very sensitive there?”
By now, with his finger giving her arse a good going over, she knew that his raging hard cock would be in need of help, but she was not going to waste that 8 inches in wanking.
“Peter, you are really naughty but my bottom is getting sore”. Peter disappointedly took out his finger, allowing Caroline, to get her favourite lube from the draw.
“Now, Peter, I think it’s time I introduced you to anal sex – I am sure you will enjoy it. You see, honey, don’t be silly and think your dick won’t fit up here. It will, but first you must ensure it is really slippery. Let’s get undressed and I will show you.
Peter was naked in double quick fashion and it took just seconds for Caroline to take off the jacket and skirt. He thought she looked magnificent. Her lovely see through girdle and soft fat tummy looked great never mind her generous and shapely tits. “Will you take off your bra as well Caroline?”
Turning around, she said. “You undo me, then”. Standing close with his cock pressing against her girdle he unclipped it and gently rubbed them and rolled her nipples between this fingers. “Ah, that’s nice”, she sighed.
Passing him the lube over her shoulder, she bent down. “Ok big boy, lube up your cock and stick some up my lovely arse you’re looking at”.
Well, it was a really horny sight. Her big and hairy pumped vulva encased by her girdle, nearly had him shooting his load as he lubed up his cock. Calming down, he then got her arse nice and oily.
“No Peter, one finger is not going to get me really ready, put three in and make sure it’s everywhere. They slipped in and out easily.
“Now big boy, sit down and let aunty Caroline take over”. Straddling over him, she placed his dick into her shitter and pushed it all the way in.
“Fucking hell, Caroline, that is really tight” Seeing that he could also go to town on her tits, he really squashed and pulled her big nipples”.
Caroline was bucking up and down and wanked her engorged clit to the extent that she nearly passed out when she came. Then feeling his cum shoot right up her arse she slumped down onto his lap.
“Did you enjoy that you naughty boy?”
“What about you, aunty”.
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