Mature Becoming a Cougar

My father died when I was 10 years old. I never forgot what he told me just before his death, "Sonia, despite our flaws, always love your family members. On the other hand, certain others will pretend to be your friends, and trusting them might turn out to be a mistake. Money by itself will not bring you happiness, but the chances are much better with it than without it." He expired the next day. We knew he wouldn't survive the summer. His end-stage cancer was too advanced, but we hoped he'd stay with us longer. Mom and I cried together for days. We were fortunate Dad had generous life insurance, which allowed us good living for several years.

When I started high school, Mom found work as a secretary at a lawyer's office. Two years later, in my first week at junior high, I noticed Mom looked more smiley than usual. I asked her if she got a bonus or a promotion. She said, "Something better. My employer asked to date me. He claimed he was smitten by me and wanted to go out with me. He got a divorce 3 years ago and said he found me irresistible."

I grinned, "Good for you, Mom. I've never met him, and I hope he is a good man."

"Honey, I Invited him for dinner on Friday. Please be here."

"OK, I'll stay for dinner."

Mom knew she had to beg me to remain at home; most Friday evenings, I was out of the house early.

By then, my body had undergone substantive changes: I was 5'4", 128 pounds, with long, dark brown hair, C-cup breasts, narrow waist, and hips that were slightly wider than I liked. I was a good student and very social. I kept in touch with a few girlfriends, with whom I frequently went out to Starbucks, movies, or shopping downtown. My face became prettier compared to the ugly duckling appearance of my youth. Boys, my age and older, noticed the changes in me and attempted to get my attention. At 17 I had my first boyfriend. It was Jay. He was a senior, very handsome, and on our football team. I went out 4 times with him. On our 5th date, he suggested we should get intimate. I said it was too early for me. It was the last time he talked to me. Jay's behavior reminded me what my father said, 'others will pretend to be your friends, and trusting them might turn out to be a mistake.'

In retrospect, the fact that Jay could leave me just because I was not ready for sex, probably affected my behavior later in life. My trust in other people was shaken, and I became more suspicious.

I had my second boyfriend, Sergei, 6 months after turning 18. He was the son of a Russian oligarch, who chose to study in America. He was good-looking, loved partying, and was very rich. Sergei persuaded me to use weed and drink vodka. I fell for his charms, and soon we started having sex. He showered me with presents and complimented me on my gorgeous body and my skills in bed. I fell for him and thought one day we would get married.

One day, at one of his parties at home, Sergei got drunk. He pulled me to his bedroom and undressed me. I thought he wanted to have sex with me and smirked, "Sergei, can't you wait to fuck me after all the guests have left?"

He stuttered, "No I caan't. In fact, I invited Steeeve and Oleg to jooin us."

He barely finished, and his 2 friends barged in. I tried to cover myself, but to no avail. The 3 guys were stronger. They pushed me to bed and forced themselves on me. I was so shocked, that later on, I could not remember details except that I left the house partially dressed, crying. At home, I stayed in the tub for hours. My mother tried to find out what happened, but I refused to talk. In the following days, Sergei attempted to apologize, but I avoided him.

Once again I learned the hard way that my father was right. ONLY family members deserve full trust.

After ending my affair with Sergei, I stopped drinking and using grass. I concentrated on achieving good grades in school, and finished in the top 20% of my class. Mom suggested I register at the local college, but I chose to become a flight attendant. I passed a background check, and following 7 weeks of rigorous training, I graduated. After 6 months of being on probation, I became a regular attendant for United, working mostly from Newark.

I was now 20, eager to exploit life. My dream of the glorious life, traveling abroad was soon crushed by reality: Most of my flights were in the USA, my service hours were unpredictable, my sleeping times were frequently interrupted, and many passengers were annoying. After my first full year on the job, I began regretting my decision.

One afternoon, I was assigned to a nonstop flight from Newark to San Francisco. Many seats were empty, and our job turned out to be much easier than usual. I was assigned to the first class passengers. When I finished serving dinner, I noticed a middle aged passenger staring at me. I approached him, smiled, and asked if he needed something.

He mumbled, "Yes, I'd like to talk to you. Please sit down for a moment in the empty seat by me."

I continued smiling, "Sir, it's an unusual request. We are not that busy now, so I can do it, but for a short time only."

He said, "Lady, it will be very short."

I sat down and gazed at him. He blurted, "I have never been married. I am very wealthy. I arranged a big party for tomorrow night to celebrate acquiring a startup company for 1.2 billion dollars. My sister was supposed to join me, but she got sick. I hate to go there by myself. If you join me at the party, I'll introduce you as my girlfriend. We'll sit together, and probably have a couple of dances. My private driver will bring you to the party and back to your hotel. You will not be required to do anything else. If you agree, I'll pay you $20,000. What do you say?"

"Sir, I don't know you. How do I know you are legit, or that your intentions are kosher?"

He pulled his ID from his wallet and showed me. The name was Jonathan Lillard, and he was 43 years old. The name sounded familiar, but I could not remember the connotation. He said, "Now google my name on your phone and read about me."

There were several articles about him, some with his picture. He was a well-known Silicon Valley personality worth an estimated 12 billion dollars according to Forbes. In an article from a week earlier, the purchase of an unfamiliar company was mentioned. He definitely was who he said.

I grinned, "Mr. Lillard, nice to meet you, but even if I was willing to do it, I didn't bring the proper clothes for an occasion of that magnitude."

"Not a problem. Tomorrow morning, my chauffeur will arrive to pick you up and drive you to Union Square. He will accompany you to any store you choose. Take 2 sets of clothes and shoes, and he will pay for everything you selected."

"May I think about it and give my answer in an hour?"

He smiled again, "Take all the time you wish, but I need an answer before we land."

I stood up and went to the back of the plane to talk to my friend. Without giving too many details, I asked her how often she got offers from passengers. She chuckled, "Obviously, one of the guys in First Class approached you. It's fairly common to get offers of 'going out'. Of course, the pretty, young attendants get more offers than me. If you have nothing better to do while there, and the guy can prove he is serious, why not?"

I returned to Mr. Lillard and said I'd agree. He thanked me and blurted, "At the party, I'll introduce you as my girlfriend, so I'd rather you call me John. When we sit at the table, I might put my hand around your shoulder, so people won't suspect, but I promise not to do anything else to invade your space."

I gave him my phone number and told him I stayed at the Holliday Inn. When we landed, John winked at me and said that Lance, his driver, would wait for me at the lobby at 9:30 am.

The next morning, I checked several stores, and after hours of shopping around, I ended up with 2 elegant evening gowns and matching shoes.

In the evening, the driver brought me to John's house. It was a mansion in Pacific Heights. John inspected me up and down and smiled, "Sonia, you are the prettiest woman I ever saw. That is why I approached you on the flight. With this dress, you look perfect. At the party, I'll tell people we met on a flight a few months ago, and since then, we started going out together. I'll tell them you are recovering from an illness and very tired, making sure nobody bothers you too much. So your job will be to smile during introductions, now and then say a word, and once or twice dance with me. After staying at least 2 hours at the party, you can leave whenever you feel like it. The driver will bring you to the Holliday Inn and will hand you the check for $20,000, as agreed."

At the party, John and I sat at the front table with 3 other older couples. He introduced us. They stared at me curiously, and one of the guys leaned and whispered in my ear, "Every woman is jealous of you. You look wonderful, and you captured the eternal bachelor's heart. Most men ogle you, wishing THEY had a chance with you."

I grinned and whispered, "Thank you, sir. You are very kind."

John sat by me and deflected most of the questions that were directed at me, claiming I wasn't feeling completely healthy yet. A middle aged guy joked, "If this is how Sonia looks when she is not at her best, I wonder if she considered participating in the Miss Universe contest." Everybody laughed politely. There were 2 food tables with various meats, salads, snacks, and desserts. A waiter took our orders of drinks. The high society really knew how to live! John and I danced twice. In both cases, it was slow. John held me in his arms and did not try to do anything inappropriate. I liked his soft touch and the smell of his aftershave.

When I was ready to leave, John kissed my cheek and mumbled, "Sonia, I hate to let you go. What will it take to see you again?"

"John, thank you for a lovely evening and the generous check, but tomorrow I have to return to my home base in Newark."

"Do you really like your job as a stewardess with an ever changing schedule?"

"I admit I thought the job would be easier and more fun, but it pays my bills."

"If I double your salary, would you consider working for me?"

"You exaggerate. I only finished high school. What work I'll be able to do for you?"

"You can begin as my secretary, typing and answering phone calls. Once I see you get along with the rest of my team, I'll have my assistant show you other opportunities within the firm."

"You want me to move to San Francisco? Everything in the city is very expensive, and more importantly, I don't know anybody here."

"In addition to your salary, you'll get all your expenses covered separately. Send me the receipts, and each month I'll reimburse you."

"John, I am confused. I thought it was a one time deal. Why do you attempt to keep me here?"

"The truth: I like you. Yes, you look terrific, but it's more than that. Both on the plane and at the party, I observed your behavior. You are quiet, efficient, and pleasant, and I need somebody like you on the team."

I stared at his eyes, "Is it REALLY what makes you offer me the job?"

He blushed, "Well... I feel toward you something I've never felt before..."

"Are you trying to date me?"

His face turned redder, "You are very direct... I am much older than you, but I hoped that working together would allow us to know each other better..."

"How old are you?"

"I'll be 40 next month."

"So you are 19 years my senior. You are still young. Are you sure you wish to date me?"

"I'd love to..."

"Is it a good idea to date your employee?"

"I own the company, so I set the rules, but if you agree to go out with me, it will be up to you if you wish to work for us or not."

"John, I like you too, but I still don't understand how can we date if you live in California and my home base is on the East Coast."

"The key problem is your unpredictable schedule. Otherwise, every weekend I'd fly to New Jersey to meet you. But if you move to San Francisco, everything will be easier: Your job will be more convenient and pay you higher salary, your schedule will be normal, and we could meet whenever you feel like it. If our relationship fails, I'll compensate you for the time you wasted..."

"... can you put it in writing? You know, just in case..."

He grinned, "Now you are talking! I love to hear you'll consider my offer. You can write the agreement yourself, and I'll sign it. Don't forget to mention the amount of compensation you'd get if, after a month, you wish to get out of the deal."

John's intention sounded genuine, but after my prior disappointments, I was reluctant to take further chances. Moving from one side of the country to the other without relatives or friends there was way too risky. I scribbled a short document, stating that Mr. John Lillard offered me a daytime job at his company for $80,000 a year plus expenses. If, for any reason, I choose to cancel the deal within the first year, I'll be compensated $100,000.

John looked at the piece of paper, typed it on his computer, and changed the compensation to $200,000...

I had tears in my eyes, "Do you like me that much?"

"At the party a couple of times I was tempted to kiss your lips, but I didn't dare. I am not going to do it tonight either. I want you to think about my offer for a day or two. If you still agree, text me. I'll arrange everything you need to move here, and it will be up to you to tell me when you wish to start in town."

It didn't take me much time to accept John's offer. He seemed like a good man who liked me a lot and was ready to do everything in his power to have me around. It didn't hurt he was handsome and very wealthy... I was fond of the guy, and the age difference didn't bother me a bit.

John paid for my rented apartment in San Francisco, and I began working in his headquarters. In the first week, I shadowed his assistant, who taught me everything from filing to answering the phone and introduced me to the important members of the team. I joined her in most board meetings and slowly learned about the big firm.

During the first week, except for brief hellos and seeing him conducting conferences, John stayed away from me. On Friday, just before leaving work, he phoned me and asked me to come to his office. When I entered, he asked, "Sonia, how do you like it here so far?"

I grinned, "Everybody is very helpful and nice to me, but I haven't done much yet."

"The weekend is upon us. Would you join me for dinner at a restaurant of your choice?"

"Isn't it too late? Don't you need earlier reservations to good restaurants?"

"Try me."

"I am not familiar with San Francisco's restaurants, but if you invite me to a seafood restaurant, I'll be happy to accept."

Later he texted me he'd arrive at my apartment at 6 pm. I was in the mood to impress him and wore a short, tight black dress with low neckline. A long necklace reached the open valley between my ample boobs. I added 3" black pumps and put red hot lipstick.

He knocked on my door right in time to pick me up. As I opened the door, I watched his eyes widen, and he froze with a large bouquet of red roses in his hand. I grinned, "These are for me? Thank you."

He woke up and mumbled, "Sonia, iis it really yoou?"

"It's me in the flesh."

"I knew you were beautiful, but now you look like Aphrodite..."

"Thank you, sir. You look very handsome too." I wasn't lying; His tall stature was complimented by an expensive suit, shiny shoes, and a silky tie.

"Lady, at the restaurant everybody will ogle you, and we won't be able to enjoy private time."

"John, if you want me to change to something simpler, I'll do it."

"No, please don't. You are so pretty and attractive in this attire, that like everybody else, I'll stare at you the whole time."

"And what's wrong with that?"

"At times, my eyes may wander to areas lower than your face."

"If you mean my tits, do you think I should be ashamed of them?"

He sighed, grabbed my arm, and led me to his BMW. Half an hour later, we arrived at Fisherman's Wharf. After a short walk from the parking lot, we reached the Scoma's. John was right; along the way, millions of eyes inspected me unabashedly, with some guys whistling at me. We ignored them. The waiter led us to a nice table by a window with a great view.

I touched John's palm, "We are lucky to get a table with the best sight of the bay."

He smiled, "Luck has nothing to do with it. I called the restaurant in advance and promised them 100% tip if we got the best seats in the house."

"Is it worth it to spend so much on a sitting place?"

"Sonia, I make more money than I'll ever need. I do not have a wife or children, why not enjoy a small part of my fortune on fun things?"

"You seem to make much effort to impress me. Who am I to you?"

"Simply put, I want you for myself."

"I like you very much. So yes, we can date, but I wonder how people are going to deal with a situation if I date the boss."

"There are 2 options. I can move you to one of our affiliates, or you can stop working for me."

"I just moved here, and I do not have a college degree. How would I find another paying job?"

"Sonia, I have an idea. Let's keep it a secret for one month, during which you'll work in the main office as agreed. After a month, I'll come up with something that I hope you'll like."

I smiled, "In a short time, I started to trust you. I hope not to be disappointed."

I took the clam chowder and halibut, and John ordered Gulf Shrimp Bisque and a Pacific Snapper. We shared cannoli and had espresso martini. Everything was delicious. I took John's hand in mine and said, "Thank you for doing all of that for me."

He gazed at me lovingly and asked, "Do you wish to stroll on the nice wharf, or you'd rather go home?"

"It's cloudy and slightly cold for my clothes. I prefer to go back home and have you there with me for... a nightcap."

He eyed me intensely, "You don't have to do it. I can wait."

"Johnny, I am not doing it only for you. As I said, I am fond of you, but if YOU think it's too soon, I'll wait."

"Honey, I want you right NOW!"

He paid, and we drove to my apartment. The whole time, I leaned on his shoulder, and my palm caressed gently his closest thigh. When he parked the car, I noted a big bulge in his pants...

We barely crossed the threshold, and John turned me around, lifted my chin, and planted a sweet kiss on my lips. It was a simple, though passionate kiss.

I chuckled, "I am sure you can do better than that."

He smiled, "I tested the waters. Realizing you didn't slap me, I can kiss you appropriately."

His lips parted mine, and his tongue penetrated my mouth. He tenderly licked my palate and then pulled my tongue into his oral cavity. His mouth tasted minty; sometime during the driving, he sneaked a mint into his mouth. I pressed my body into his. my tits crushed his muscular chest, and I felt his erection growing. His hands began trailing my body, and soon his fingers found my left breast. They were warm and gentle. My cunt started leaking, and I murmured, "Let's go to the bedroom."

He sat on the bed's edge and said, "I fantasized about this moment for a long time. May I see you naked?"

"Only if later I'll see you in the nude too."

I teased him by lowering the dress's back zipper at a snail's pace. Next, the shoulder straps fell sideways, and the upper part of the dress landed on my tummy. John gasped loudly, and the front of his trousers threatened to rip the zipper. I lowered the dress further, letting it fall on the carpet. Next I unclasped my soft bra, and it flew forward, revealing my round tits. He licked his dry lips, and his eyes focused on my nipples. The mere stare was enough to cause them to harden and become pointy. I bent down and slowly lowered my low-cut panties, displaying my bare cunt. He stopped breathing and clutched his fists, likely trying to hold himself from pouncing on me.

I smirked, "Sir, are you happy now, or you wish me to remove my high heels as well?"

He blurted, "You are so stunning! I am speechless. No, don't take off your shoes, please."

Unlike me, he undressed rapidly. In less than a minute, he stood naked before me. John's skin color was lighter than mine. His muscles showed a good tone, and I liked his hairy chest. My eyes explored downward, watching his 6 pack and focusing on his tumescent dick. It was a beautiful specimen: about 7+ inches long, thick, with a large spongy helmet, and it stood in attention. His muscular, long legs completed the appearance of a younger person.

I said, "Johnny, are you sure about your age? Judging by your looks, I'd say about 30 years old."

He didn't bother answering. He came closer, raised me in his strong arms, and placed me supine on the bed. He growled, "You are so sexy, that I can barely keep myself from attacking you..."

I whispered, "I want you too. Don't hold back."

He mounted the bed, spread my legs, and invaded my pussy. I was drenched, and his cock slipped smoothly inside, even though his girth pushed the vaginal walls to the limit. As his eyes concentrated on mine, he began ramming his member back and forth at an accelerated pace. My hands trailed his shapely pectorals. My horniness heightened. His rhythm increased, and his palms tweaked my boobs. I heard myself moaning, and my fingers pinched his ass cheeks, pulling him deeper into me. His thrusts turned fast and furious as I felt I was close to cumming. I mumbled, "You feel great. I am so close..."

He roared, "Me too. Here it comes!" and then I felt him tense, and his organ started erupting in my cunt. That was the moment I lost it as well. In my daze I could feel my pussy spasm on his ejaculating pole, squeezing it and milking it for all he got. I had no idea how much time had passed; I was in my own heaven...

John gradually slowed down, and when his penis began deflating, he pulled out and lay by my side. We relaxed for a while, and then I raised my upper body and kissed his lips, "Thank you, lover. I feel great. Are YOU OK?"

"I am better than OK. I am trying to lie still, thinking it was a dream, and I hate it to end."

I chuckled, "Honey, it wasn't. Would you like a cup of coffee before you leave? I am afraid you'll have to go home because if I am late tomorrow, my boss may fire me..."

He smiled, "Right now I am at your mercy. I want you mine whether you work for the company or not."
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