Oh Carole

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Simply the life of Carole.
8.3k words
4.59
45.8k
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Part 1 of the 3 part series

Updated 06/08/2023
Created 01/25/2018
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Croony
Croony
750 Followers

Carole and her friend Val met up a couple of times a week for lunch to have a catch up and a moan about life in general, usually their sex life.

They normally met on a Tuesday and a Thursday and had at least one night out together every two weeks or so, usually on a Friday.

They had been friends for over ten years from when they had first met at their local yoga class.

Carole was an extremely glamorous forty year old. She was five feet six inches tall, slim with thirty six DD breasts and blonde hair that hung over her shoulders and many people said she could have still been a model.

Val, on the other hand was of Caribbean decent, five feet ten inches tall with extremely large forty DD boobs and long black hair. She was slightly more voluptuous but carried it very well because of her height. At forty five she looked younger even though she had been married three times.

Her first two divorces had secured her a healthy bank balance and when her third husband died of a heart attack she was left a large house in St Johns Wood, North London and a large portfolio of shares.

She worked as a part time self employed interior designer for wealthy patrons. Even now she missed her husband who was an industrialist although he was twenty five years her senior.

If his flight hadn't have been cancelled and if he hadn't arrived back home he wouldn't have walked in on his wife naked except for black thigh high stockings and heels screwing the delivery boy on the sitting room floor then maybe he wouldn't have had a heart attack.

Carole also lived in St Johns Wood although under different circumstances. When she was twenty years old she was working in the Houses of Parliament as a secretary for a then Tory MP who was also a Knight of the Realm and twice her age.

As, in those days, it was almost normal to have an affair with one's secretary, the pull of a powerful man was hard for Carole to resist and they screwed each others brains out at his flat in Mayfair while his wife resided at their stately home in Oxfordshire.

Their affair came to an abrupt end when she told him she was three months pregnant. He hit the roof, demanded she have an abortion and threatened her with whatever he could think of.

He panicked as he knew if the scandal was to get out he would have to resign from his Government post.

After a month of threatening, pleading and begging he finally accepted Carole was going to keep the child and so he told his wife.

He was surprised at how calm she seemed to be taking it.

His wife, Lady Barbara was forty eight but never could have children and so she was secretly pleased that there would be an heir to their fortune and home when they both died. A meeting was set up for them to meet up with Carole in a restaurant in Mayfair to discuss a way forward.

Carole was extremely nervous at meeting Sir Charles's wife but took a deep breath and entered the restaurant to be greeted by Charles who in turn introduced his wife. After a few minutes of niceties with drinks having been ordered Carole excused herself and went into the ladies toilets.

She was leaning over the sink redoing her make-up when the door opened and in walked Lady Barbara.

Barbara was a tall handsome woman with a slim figure. She walked up to Carole who had turned towards her and placed her hands on the young woman's shoulders.

'If I'd known how sexy you were I would have fucked you myself,' stated Barbara. 'You really are a pretty slut aren't you?' she said sliding a hand between Carole's thighs and over her silky cream panties.

Carole gasped as the older women stroked her pussy.

'Maybe when the baby is born I'll come and visit,' she said as she buried her hand inside Carole's knickers before sliding two fingers inside the young woman.

Carole groaned.

'Nice and wet. I guess you've not had sex with my husband for well over a month now. Are you going to cum for me?' Barbara asked as her thumb rubbed over Carole's clitoris.

'Oh God.' moaned Carole as she felt her orgasm approaching.

When Barbara kissed her full on the lips and slid her tongue inside her mouth Carole came hard, moaning into the older woman's mouth.

Barbara washed her hands and told Carole to get herself together and come back to join her and her husband.

'Right,' said Barbara when Carole returned to the table.

'This is what is going to happen. Charles will buy you a house and provide a trust fund for the child as well as pay maintenance until the child reaches the age of twenty five. The trust fund will be accessible when the he or she turns thirty years of age. Do you agree Carole?'

She was stunned but murmured her acceptance.

By the time Josh was born a house had been provided and Barbara did visit twice a year on her trips to town where she took advantage of Carole's pretty mouth with her juicy pussy while the boy was sleeping.

When Josh was four Carole was advised that Lady Barbara has been killed in a helicopter crash as she was being flown to the Derby at Epsom to meet up with her husband.

Fortunately Sir Charles continued with the arrangement even though five years later he remarried.

By now Carole had found work as a personal assistant to the wealthy owner of a successful financial services company at Canary Wharf, London. It helped he was in his mid sixties and both Brian and his wife Cynthia treated Carole with the love and respect as if she was their own daughter.

It was the following Tuesday that Val and Carole met for lunch. Carole didn't seem to be her normal happy self.

'Hey, are you OK?' Val asked.

'Yeah, sure,' replied Carole but Val knew otherwise.

'Come on, spit it out. What's wrong?' queried Val.

'Well, if you must know, and this goes no further right?' demanded Carole.

Val nodded solemnly.

'When I got home on Friday night Josh was still up watching the television. I'd taken my shoes off so not to make a noise and wake him then quietly padded into the sitting room to find him sprawled on the sofa masturbating to a porn film.' confessed Carole.

'He's eighteen babe, most boys at his age watch porn,' added Val.

'It wasn't the fact that he was watching porn, it was er...' stammered Carole.

'Go on,' demanded Val.

'Oh hell. It was the size of his cock,' blushed Carole. 'It was huge.'

'How huge?' asked Val excitedly.

'Must have been about eight or nine inches and thick. It didn't look right on such a small frame,' said Carole.

Josh was only five feet seven inches tall and quite slim.

'I rushed away before he could see me but the next night as I walked past his room I saw he'd left his door ajar and as I went to close it I peeped in to see him reading a magazine stroking his cock. I wasn't mistaken. It is huge.'

'Oh my God. Did you say anything to him?' asked Val.

'No. The next day when I went to tidy his room I looked under his mattress and found the magazine he was reading.'

'Top shelf?' asked Val.

'Not quite,' said Carole. 'More on the lines of mature women in fetish wear, you know latex, PVC, leather, that kind of stuff.'

'Bloody hell!' exclaimed Val. 'Are you worried he's turning into a perv?'

'It's more than that,' said Carole. 'I'm wondering if he meant me to catch him?'

'I know you've said he tried to catch you in your undies before but do you think he actually sees you in a sexual way?' asked Val.

'I don't know. I'll just have to see what happens next,' sighed Carole.

'Don't worry about it. I'm sure he'll end up taking his frustrations out on a girl his own age soon,' said Val.

'But I do worry Val, He's never had a proper girlfriend yet. I'm sure he's still a virgin,' replied Carole.

Val smiled and her brain went into overdrive.

'I think we need another night out,' she said and so one was arranged for the following Friday.

Val knew the owner of a new venue in Camden and scored them VIP tickets for the club. Carole wasn't really in the mood but went along but by the time she'd downed three glasses of champagne she was in the mood to flirt.

A tall dark haired Italian in a sharp black suit was sitting next to her and trying his hardest to pull. Carole was lapping up the compliments and began stroking the top of his thighs.

'God they are so easy to get excited,' thought Carole as she could feel his erection straining at his trousers.

'Caro, let me take you home where we can be more comfortable,' he asked.

'Your home? What about your wife?' asked Carole cheekily after spotting his wedding ring. The Italian looked a little uncomfortable.

'Unfortunately we can't go to mine as I have a fourteen year old son who is a light sleeper and I am very vocal when I'm being fucked,' she lied while squeezing his cock. 'And I'm sure to go wild riding this big monster.'

The poor man didn't know what to do. There was a gorgeous blonde woman playing with his cock saying how wild she was in bed and he couldn't answer her.

Carole stood up and said, 'maybe next time.' before she sauntered over to the ladies room feeling very smug with herself.

On the way out she was stopped by a young black guy who was wearing a cream polo shirt, black jogging bottoms and leaning on crutches. Carole noticed his foot was in plaster and even in the dim lighting she recognised the young footballer who had just been signed for an enormous fee by one of London's top clubs.

'Well hello gorgeous!' he said.

'Hi stud,' she shot back.

He struggled to move to a more secluded bit of the club and motioned Carole to join him. She smiled to herself thinking. 'What's he going to do in that state?'

'I saw you knock back the smarmy old guy,' he said. 'I wondered if you'd like to come back to my hotel suite and party?' he said confidently.

'Oh you are sure of yourself Mr Big Shot?' laughed Carole. 'I'm old enough to be your mother!' She stroked her hand down his hard chest and down to his silky tracksuit bottoms.

'Do you have a mother fixation?' she asked rubbing the outline of his now very erect cock.

He moaned and his cock twitched when she used the word mother. Carole went for it. She slipped her hand under the waist of his pants and took hold of his substantial cock.

'Mmmm,' she thought, 'it might not be a bad idea if I was in the mood.'

'So you want Mummy to come back to your bedroom do you? she asked as she slowly masturbated the boy. 'Would you like Mummy to undress you for bed? I wonder what Mummy could do next?'

'Do you think you'd like Mummy to strip down to her black stockings and suspenders but leave her high heels on and climb up on the bed with you?' By now the young man was squirming and trying not to cum.

'Would you like to slide your big black meat into Mummy's shaven white pussy and fuck Mummy hard?'

As she said this she stuck her tongue in his ear and he exploded all over Carole's hand and the inside of his jogging bottoms.

Wiping her hand on his shirt she just said 'Oops' before walking back into the ladies to wash her hands.

Back in the club she saw the young footballer limp to the exit alone and she giggled.

She thought she should leave too and sought out Val to tell her.

Val was being chatted up by the same Italian who had tried it on with her so she just waved and nodded at the exit.

Val nodded back and raised her eyebrows causing Carole to smile.

It was Monday morning and Josh had only recently got up and was making some coffee. It was the start of the school holidays and his mother was already at work.

He padded around in bare feet wearing only a pair of sleep shorts and an old t-shirt when he heard the door bell ring.

'Hello Josh, is your mother at home?'

Val stood at the door.

'Er no, she's at work,' answered Josh a bit surprised.

'Oh I could have sworn she said she was taking today off,' lied Val.

'Never mind, I might as well come in and have some of that delicious coffee you're brewing.'

She marched past Josh and into the kitchen.

Josh couldn't help but notice the tight black leather trousers she was wearing and especially the way they moulded around her shapely bottom.

Val poured two cups of coffee and carried them to the sitting room. Josh followed and kept staring at the older woman's sexy arse. She put the cups on the coffee table in front of the sofa and beckoned Josh to sit beside her.

Val crossed her legs causing the leather to creak.

Josh couldn't help but stare at her long legs and when she recrossed them he could feel himself get an erection.

'Just as I planned,' thought Val.

Josh sipped his coffee whilst trying to hide his hard on.

Val made small talk then suddenly said, 'Josh, are you alright? You seem to look a little flushed.'

Josh garbled something about being warm and he was in two minds whether to run upstairs, lock himself into the bathroom and deal with his hard-on.

Val leaned forward and grabbed his cock that was by now tenting his shorts.

'Oh Josh! Did I cause that?'

Josh groaned as his mother's best friend rubbed his cock up and down its length over his shorts.

She then dropped to her knees and peeled down them down freeing his big fat cock.

'Oh my God, his mother wasn't joking,' she thought.

She slowly started to masturbate him.

'Was it my leather trousers that got you all excited Josh? So if you like leather you should see what else I have in my wardrobe. You will love my latex and PVC outfits so why don't you pop over on Wednesday morning and I'll wear something for you?'

Val could tell Josh was about to cum so she placed her lips over his cock and took him deep into her mouth. Seconds later Josh exploded shooting his cream down her throat as she sucked him dry.

'Well young man. That was very tasty, I hope to see you on Wednesday.' she commented as she got up then left the house leaving Josh in a daze.

'Oh, and please don't tell your mother. Let it be our little secret!'

Lunch the next day was a fairly quiet affair although they shared a joke about the previous Friday and laughed at the antics of the Italian trying to get laid. Carole told her about the young footballer.

It was a nervous yet excited Josh who rang the bell at Val's house on Wednesday morning.

He could hear the click clack of Val's high heels on her wooden hallway. The door opened and Val ushered him in.

She wore a long black silk robe that was tied tightly around her waist and leaned in to give Josh a hug.

'I'm so glad you came I've done nothing but think of that lovely big hard cock of yours since Monday,' she enthused.

She took Josh's hand before he could change his mind and led him upstairs to her bedroom. Josh gulped when he saw the four silk scarves tied to each corner of the bed.

'Right let's get you out of these clothes, shall we?' said Val.

Josh stood still as she pulled his polo shirt over his head and undid his shorts.

'I..I don't think...' stuttered Josh but Val ignored him and soon had him naked and on his back on the bed.

When he was tied spreadeagled she sat facing him toying with his now semi hard cock. She thought he looked so cute and vulnerable, an anxious expression on his face.

'I've got a surprise for you darling that I hope you'll like. I'm sure you will. Won't be long,' she said as she squeezed his cock one more time and disappeared into the bathroom.

Ten minutes later the door opened and Josh gasped as Val entered the bedroom.

She was wearing a shiny black latex girdle with black shiny latex stockings and shiny thin black latex elbow gloves. She was also wearing high heels and a black leather choker.

Her huge forty DD breasts swayed as she walked towards the bed.

'Well darling, do you like my outfit?'

Josh could only nod.

She took a bottle of lube from the bedside table and squirted a large dollop into her left hand. Putting the bottle to one side she dripped lube from her shiny gloved hand down into his hard-on . Josh gasped as the cool liquid coated his cock.

Val took hold of his erection in her right hand and his testicles in her left as she slowly masturbated him and stoked his balls.

She used her slick latex hand to peel back his foreskin and reveal the shiny head of his cock. More lube on her glove and Val slowly stroked the crown of his cock causing him to groan.

'What a nice big shiny helmet you have,' said Val never taking her eyes off his throbbing cock. 'I'm going to enjoy using this over the summer holidays. By the time you go to university in September you'll know all about pleasing women.

Josh let out a gargled moan and raised his hips to try to get himself off on Val's rubber gloves.

Val continued to edge his cock, knowing when to slow down when she felt like he may go over the top and to go a little faster to make him gasp a little more.

Soon Josh was soon begging Val to let him cum but Val just giggled and talked dirty to him, keeping him close.

Josh was panting and whimpering, quietly begging to be allowed to orgasm.

Val let go of his balls and stroked her latex finger over his little rose bud causing him to shudder. She teased her finger just inside his hole as she continued to stroke him slowly.

Josh pleaded. 'Please, please..' over and over again.

'You want to cum?' Val asked.

He was so hyper he could only nod.

'Since you asked nicely,' she said and slid her finger all the way into his arse and wanked him faster and harder.

Josh screamed as he shot rope after rope of cum up into the air that came down over his naked chest and her shiny gloves. Val kept up her pumping and it was only after Josh couldn't produce any more cum that she withdrew her finger then let go of his cock allowing Josh lay back panting having never jizzed as hard before.

Val went into the bathroom and stripped off her latex gloves.

Josh was lying quietly on the bed when she came back in.

'Are you ready to pleasure me now? I'm going to teach you how to eat pussy.'

She climbed up on the bed and straddled his face.

'Don't you love that smell? Latex and wet pussy,' she said as she lowered herself down onto his face.

'Lick me Josh. Get that tongue in me now and eat me.'

Josh stuck out his tongue and tentatively licked Val's folds. He explored her lips and stuck his tongue deep into her causing Val to groan. She started to ride his face and tell him what to do and when. Soon Josh got the hang of what excited the older woman and feasted on her pussy.

'Lick my clit. Further up. That nub. Yes. There. Suck it. Oh God. Yes!'

Val was writhing on his face as he brought her closer and closer to orgasm.

'Oh God Josh. Yes. Oh, I'm cumming,' she gasped as she flooded Josh's mouth with her juices.

Lying next to Josh in post orgasmic bliss she slowly stroked his body.

'Wow, wasn't that exciting? She asked. Josh could only mew. He'd never experienced anything like it.

She untied him and then got off the bed and went into the bathroom. When she returned she'd stripped off her latex underwear and was wearing her long black silk robe.

'I've ran the shower for you so I suggest you pop in and clean up before you go. I'll meet you in the kitchen.'

Josh saw that Val had made coffee and was sitting at the breakfast bar. She motioned him to join her.

'Well Josh, are you glad you came?' She smiled at her double meaning.

'Ye..yes, thank you. It was amazing,' stuttered Josh.

'Would you like to come back so I can teach you more?' she said.

Josh looked sheepish but nodded his head yes.

'Are you a virgin?' asked Val.

Josh blushed again nodded yes.

'Well, we'll have to do something about that,' she said with a smile.

The next day Val and Carole met, as usual for lunch.

Val told her what had happened the previous day and also on Monday. Carole listened with astonishment and a hint of annoyance that her best friend had seduced her son. However, she was also turned on by what she heard.

Croony
Croony
750 Followers