Enter the Cougar Ch. 02

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Doing business, having kinky fun and getting a portrait.
14.2k words
4.6
13.9k
12
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Part 2 of the 2 part series

Updated 06/09/2023
Created 11/12/2019
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I would like to thank Georgia Alice for helping me to name and dress the characters.

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If you're impatient you might want to get right to the story, because what I'm about to say here is irrelevant to its content.

There's an issue about anal sex in erotic stories that somewhat bothers me. I'm well aware that anal sex requires thorough preparations which takes considerable effort. At the same time I also feel that describing such preparations disturbs the pacing and kills the mood. For that reason in most of my stories I'm assuming that the digestive system of characters in erotica has only the beginning and its other end is used solely for sexual purposes. ;-)

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THE MORNING

Knock, knock. The knocking was soft but audible.

"Come in" said Julia "I'm already awake."

Maria opened the door and walked into the room, as always inside of the mansion she was wearing a naughty maid uniform which revealed more than it covered. The hostess was awake, but she was still lying in her bed. When the maid opened the curtains she sat up and outstretched her arms, the quilt slipped down and exposed her huge breasts; as usual she had slept naked, but neither of the women were bothered by the nudity.

Maria took a mat from a wardrobe and laid it on the floor. Julia got up from the bed and began her customary morning exercises, still completely naked. It was just a short five minute workout to stretch the sinews after the night and get the blood pumping. The maid meanwhile made the bed.

"Did you sleep well, Missus Julia?" she asked politely with her cute Spanish accent.

"Yes, thank you. I'm ready to welcome a new day."

"You look fresh and beautiful as always."

"You're sweet, but that's a lie. I might be fresh, but without the makeup I look terrible."

"You know it's not true."

Maria finished making the bed and added:

"I'll lie out the clothes for you while you're in the bathroom, Missus Julia. Please, get down soon, I'll have breakfast ready."

"Thank you" replied the hostess "I'll be right there."

Washing her face and brushing her teeth did not take that much time, but applying the makeup was much more time-consuming. Maria was partially right, Julia did not look bad in the morning with her face somewhat sleepy, but clean. Despite her age she still looked relatively youthful and had barely any wrinkles on her face. It did not mean though that she could not look any better, properly applied makeup turned her into a real sex bomb, a hot cougar. She usually wore a natural one, but with slight additions of bimbo aesthetics, red lips were the most prominent such feature.

Her outfit was already lying on the bed when she returned to the bedroom, although the term "outfit" might be an overstatement. There was a pink lacy bra, one which would support Julia's breasts, but not cover them because it was cupless. Next to it was an equally pink lacy thong, but the cougar did not put it on yet; first she reached for a small anal plug and a bottle of lubricant. With experienced moves she lubricated her backdoor and the toy, then carefully slid it inside; a red jewel began to sparke between her full buttocks. Next to put on was a suspender belt, of the same set as the rest of the lingerie. Julia then carefully rolled stockings up her long legs, the nylons were sheer, pink and had subtle pattern running up their side; with almost theatrical motions she attached the stockings to the belt. Only then she put on the panties. There was one more item to be worn - a nipple chain; it was light, delicate and made of real gold. The clamps held firmly to her nipples, but their squeeze was not overly hard; this was an ornamental item, not a part of bondage gear. Julia picked the rest of the jewellery herself, it was tasteful and subtle which contrasted with the naughty lingerie. The outfit was completed by a pair of purple patent heels on fifteen centimetre tall stilettos; they had also been laid out by the maid and there were no more clothes prepared.

When the hostess got downstairs Maria was finishing the breakfast preparations. She brought the plate into the room and laid it on the table.

"I laid the panties already?" the maid asked almost apologetically "I'm sorry, Missus Julia, that was my mistake. Please, bend over the table, so I can help you take them off, so you can fully enjoy your breakfast."

Without a word of complaint the cougar obediently bent over and Maria pulled the lacy thong down her long legs.

"There you go" said the maid with a smile as her employer stood up "much better now. Please sit down" she added as she pulled away the chair.

A large realistic penis-shaped dildo was attached to it.

Everyone acted as if their morning behavior was perfectly normal. The maid carried in the rest of the meal, then finally brought a tea kettle, she poured it into an empty porcelain cup. Julia loved coffee almost as much as tea, but she rarely drunk it in the morning.

"Bon appétit" Maria's French accent was surprisingly accurate.

"Thank you, Maria" replied the hostess and began to casually eat her meal.

As soon as she did that the dildo inside of her pussy began to vibrate slowly. She let out a soft moan, but continued the meal.

Julia ate her whole breakfast with appetite and without any signs of discomfort, even though the sex toys were impossible to fully ignore, especially the sizeable dildo. The vibrations were constant but not strong enough to even bring her close to the edge. When she was sipping the remnants of her tea Maria showed up again.

"Mister Jonatan will be here in thirty minutes" she said "I've laid out the rest of your clothes on your bed."

"What would I have done without you, Maria?"

"Funny you say that" the maid made a small but devious smile "half an hour is a lot of time and I thought that you could remain in your chair for a few more minutes."

"I take it that you had already thought of ways to entertain me" replied Julia with a smile.

"Nothing too fancy" with these words the maid turned the vibrations up.

"Mhmm..." the hostess moaned audibly.

"Missus Julia, you're such a slut" Maria turned the toy up even more.

"MHMM."

"Aren't you?" she asked, the devious smile grew larger on her pretty young face and suggested that she was expecting an answer.

"Yesss..." the hostess closed her eyes, but the expression of delight remained on her face.

"Yes what, Missus Julia?"

Up went the vibrations.

"MHMMM! YES, I'm a slut!" she opened her eyes and grinned back at the maid.

Maria turned the vibrator to maximum, but soon turned it back down; she did not turn it off though. She put the remote on the table in front of the hostess and went behind her chair. She put her arms around it and grabbed Julia's breasts, gently at first, but then her small palms began to grope the large orbs more possessively. Slowly Maria's hands moved towards her employer's nipples. Once she reached them she grabbed the clamps, she pulled and twisted them slightly.

"Ahh" there was little sign of pain in Julia's voice, mostly excitement.

Maria suddenly squeezed the clamps harder between her fingers.

"AHH" Julia cried out.

The maid pulled the clamps forward.

"AHHH!" the pain in the hostess' voice was audible, but she did not move or protest in any form.

Maria let the clamps go, the chain dangled for a moment causing more discomfort, but the pain was gone. The maid returned to the table and took back the remote; she turned the vibrations to maximum.

"MHMM!"

"Would you like to cum, Missus Julia?" she asked with the devious smile returning to her face.

"Yesss..."

"You're such a slut, Missus Julia."

"MHMM YESS"

"But that's not the right time to cum" the maid turned down the vibrations to minimum "Mister Jonatan will be here soon and you should get ready" she feigned an innocent look.

The hostess was breathing heavily for a short while, but composed herself quickly.

"You little devil" she said with a grin "just wait till evening. I'll deal with you appropriately."

"But you have a meeting with the painter in the evening, Missus Julia" Maria was a personification of innocence.

"Sometimes I think you're too smart" Julia winked.

"Thank you, Missus Julia. Let me help you get up."

With the maid's assistance the hostess got up from the dildo and then began to walk to her room. Maria's voice stopped her.

"Don't forget about your panties, Missus Julia."

The maid was dangling the thong on her finger, the innocent expression remained on her face. The employer returned, took the panties and finally went upstairs; she did not put the thong on until she reached her room.

The outfit Maria had prepared was, just like her maid uniform, a naughty version of a professional business suit. The light purple blouse would have been more suitable for a party than office. Not only it had a relatively deep cleavage, but also was semi-transparent; it would leave no doubt as to what kind of bra Julia was wearing. The dark purple skirt was not professional either, it was incredibly tight and ended only several centimetres below the buttocks; it could be considered flirty at least. Julia took off the nipple chain, but kept the plug in; she put on the panties and the other two items and went down to meet Jonatan.

THE BUSINESS

Jonatan was Julia's right hand in her branch of her husband's company. He was ten years younger than her, but had a brilliant mind and at the age of thirty two he was perfectly suitable for his responsible position. The man had a youthful appearance and a boyish charm which caused many to consider him too young for his job; Julia knew better and quickly learnt of his skills and talents. Jonatan was aware of his employer's... extravagances, but just like she could see beyond his youthful appearance, he could see beyond her slutiness. They made a really good team and surprisingly enough had never had sex; although that restriction might have been the reason why they cooperated so well on a professional level.

As was his custom Jonatan arrived a few minutes earlier, then patiently waited for his employer by a cup of tea served by Maria; she did not let him wait too long, because being on time was her custom as well.

"Good morning, Julia. You look stunning" he said with a polite but genuine smile.

Natural bearing was an integral part of his image.

"Good morning, Jonatan" replied the employer with a warm smile "I try to do my best to match your good looks. As much as my age allows me."

"And you never fail."

They shared a firm handshake which somewhat contrasted with the flirty greetings.

"Thank you, you're such a sweetheart. Any good news?"

"Yes, a big one. Igor Karpatsky called and asked for a meeting, he wants to discuss our proposal in person."

"Isn't Igor that chauvinistic pig?"

"Yes, that's him. But he's a big fish and has one more flaw of character - short notice."

"When does he want to meet."

"Today. At eleven. This is a great opportunity for a huge contract" if Jonatan was excited he was hiding his emotions really well.

"Oh, good. I think I know of a way to ensure that we'll get it."

"Me too. I though we could propose a discount on..."

"I have a better idea" Julie place her hand on Jonatan's shoulder and smiled "one that would not cost us any money."

"I'm all ears" Jonatan was an independent and industrious person, but also knew when to listen.

Julia laid out her plan to him, it was an unorthodox one, but the young man had learnt to trust his employer in such instances. After their conversation he called Karpatsky's assistant and confirmed their presence at the meeting.

Igor Karpatsky was a real male chauvinist pig indeed; a truly dedicated one at that. He not only believed that women were inferior to men, he also felt obliged to prove it regularly; or rather to perform acts he considered to be proofs. He ran a large successful company which hired women for nothing higher than secretarial positions; and he made sure that his female employees were aware of their status. The rotation was obviously significant, but for Igor that was just another proof of his thesis.

He had first married at the age of twenty five, to a nineteen year old girl; she was astonishingly beautiful, but not very smart. Igor divorced her ten years later to marry another twenty year old, again beautiful but dumb. He repeated the process two more times and now at the age of fifty six had a fourth wife; she was twenty one, stunning and silly. Karpatsky was not a monster though, since he considered women to be inferior he believed that they needed to be taken complete care of by men. His lawyers had full control of the divorces, but the ex-wifes always received enough money so "they wouldn't have to overburden their silly little heads" as Igor liked to call it.

Karpatsky was tall and ruggedly handsome, stocky but not fat; he shaved the remnants of the hair on his head to keep it perfectly smooth. The man always wore well tailored expensive suits and watches that could buy you a small apartment. Igor considered Hank (Julia's husband) to be a fool for letting his wife have any responsibility in his company. He was not exactly content to be dealing with a woman as an equal either, but there was business to be made and he was pragmatic enough to overcome his prejudice. He might not have done so, if not for Jonatan's involvement, it was so much better to discuss important matters with a man. On the other hand maybe he could benefit even more from the business, if he decided to abuse Julia's inferiority; he would need to be subtle enough, so that Jonatan would not see through his ploy.

A woman and a kid, ha! It almost felt like taking candy from a baby. Whenever Igor asked a question that bimbo tried to answer, but it was the kid who had to finish the answer and give him all the details. Once or twice Jonatan even interrupted his employer to correct her statement. It was a shame he was working for a woman, but maybe he could turn into a man after all. He seemed a decent negotiator, but clearly no match for Igor Karpatsky. The bimbo's attempts at being a businesswoman were amusing, but she should have focused on her tits instead.

Karpatsky had always preferred younger women, but he had to admit that the mature bimbo looked pretty good. The slut almost had her tits on full display! And she had killer legs that looked marvelous in those stilettos. Igor was a leg man and he wondered how it would feel to get between them. Was her mature pussy loose or still tight and wet? At least she knew to show off her body, not the brain which she obviously lacked. Karpatsky would never marry a cougar, but fucking one from time to time was not a bad idea.

Getting a favourable deal from that silly pair was almost too easy. Igor had to make few flashy, but ultimately meaningless concessions and they agreed to his terms. But he wanted to get something more from this particular deal.

"Jonatan" Karpatsky said in a polite tone "could you leave your boss and me alone for a moment. I'd like to discuss something in private."

"Of course" replied the young man without even looking at Julia.

Yep, he could still turn out to be a man.

When Jonatan left the room Igor looked Julia in the eye and said bluntly:

"I like it when a woman knows her place."

"What are you implying?" she did not sound offended which confirmed Karpatsky's suspicions about her status and intellect.

"You had made a wise choice to hire a man to do the job. But if you want the contact which we just agreed on, you'll have to do a woman's job."

"What do you mean? I'm Jonatan's boss..." she hesitated.

"You came here almost flashing your pussy in that short skirt and you're flashing your tits even more. I'm sure you know what I mean."

"Oh...I..."

She again did not sound too offended, the women were so easy to read and manipulate.

"If you're suggesting a date" Julia added with a subtle smile "I'm sure we could work something out."

"Not a date. Right here."

"What? You can't be serious. People would hear us."

And she was concerned about being heard, not about being a whore.

"They won't. The walls and doors are thick and I'll order the secretary to leave her post. Bend over the table and you got the deal."

That was a small meaningless concession, just like the ones he had made during their business negotiations.

"I... ehm..." Julia hesitate.

Her face looked like one of a bimbo who is trying to ponder on matters that are too complex for her.

"My time is valuable" Igor hastened her, this created tension caused by a sense of urgency.

"Oh... ehm... okay. I'll do it."

"Then bend over, bitch!" Karpatsky almost shouted.

When the woman complied Igor stayed true to his work and called the secretary; he told her to leave and not let anyone in. He was admiring Julia's full buttocks and long legs as he issued the commands; the cougar had a really fuckable body. When he put down the phone he spanked Julia's exposed ass hard.

"Ahh!" there was a little excitement mixed with the pain and shock in her voice.

"You love it, don't you bitch?"

He groped her buttocks aggressively while she remained silent.

"Answer me!" another hard slap landed on the cougar's ass.

"Ah! Yes..." came a weak answer.

"Yes, what?" SLAP!

"Yes, sir."

"Hm, sir. I like that. You clearly know your place" Igor's large strong palms continued to grope Julia's buttocks "but that's not what I was asking about. I want to hear you say that you love being such a slut. It already is apparent, but I want to hear it from you directly."

"Yes, sir. I love being a slut."

"Good."

There was another slap, but a playful one this time. Karpatsky opened the zipper on the side of Julia's skirt and pulled it down her long legs. When he reached the floor she raised one of her feet and stepped out of the skirt.

"You really are a well trained whore."

He caressed the nylon covered skin along her whole limbs as he rose.

"Panties over suspenders" Igor said in an amused tone "who were you planning to fuck, slut? Don't tell me it's that kid."

"N-no. I... it's my... chauffeur."

"A chauffeur? Ha! So cliché. I knew you were a whore from the first glance."

He finally grabbed the band of her panties and began to pull them down.

"A butt-plug?!" SLAP!

"Ahh!"

This hit was again hard.

"But I never guessed you were THAT big of a whore."

Slap.

"I bet you'd love to get your ass fucked" Igor stated as he began to play with the toy.

"Yes, sir."

"Yes sir, what?" Slap.

"Yes, I'd love to get my ass fucked, sir."

"Beg." Slap.

"Please, sir, fuck my ass. I'm a huge anal whore, my ass craves your huge cock. I beg you, sir, please fuck me ass."

"Not bad. I bet you do that often, slut. But no. I want pussy. You can keep that little toy of yours."

Forcing a slut to beg and then denying her the request was so humiliating and Igor loved it, even if it came so easily like this time.

Karpatsky finally pulled Julia's panties down and she stepped out of them. He again caressed her legs as he stood up. The man spanked the full buttocks lightly once more.

"Spread your legs" he commanded.

Julia obediently spread her long limbs as wide as the position allowed. Igor put his hand between them and fingered her pussy; he shoved two fat fingers inside.

"Already wet, just as I had expected. I could hire you as my secretary. I bet you're a better cocksucker than any of those dumb bitches I employ. They're only good for making coffee."

The man soon withdrew his fingers, he leaned forwards and placed them by Julia's mouth.

"Lick 'em clean. Taste your own slutiness."

The cougar submissively obeyed and wrapped her lips around the thick digits.

"Enough" Karpatsky soon said "get on your knees, bitch and suck my cock."