The Self-made Millionaire

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This story is completely fictional. The company is NOT real, the company owner is NOT real, the High School is NOT real, and all the characters are totally made up and NOT based on real people. All characters engaged in sex are over 18.

The Self-made Millionaire CH. 01

A Young Man’s Invention Makes Him a Multi-millionaire ©

My name is G. Randall Winston, III. I know. It sounds really nerdy. The fact is, I have been a nerd all my life. It wasn’t so bad growing up though because I was a rich nerd. While a lot of nerds are picked on and bullied, and the “cool” kids didn’t want to be friends with them, it’s different when you’re rich. The so-called cool kids actually wanted to be friends with me because they knew I could afford to do things that they couldn’t unless they were with me. For instance, if the hottest band was having a concert, I could afford to buy tickets on the front row, and if you treated me right, I might take you with me. And unlike most nerds, I didn’t have any trouble getting dates. Of course, it didn’t hurt that I didn’t look like the stereotypical nerd. No black-rimmed glasses and no pocket protector full of pens. When I was a senior in high school, I was just shy of 6’2″, and I weighed 210 pounds. I guess my dad knew what it was like being a nerd, so I had been going to his gym with him since I was 15. He had me working with a personal trainer, and he helped me bulk up. I developed a chiseled chest, six-pack abs, and muscled arms and legs. Because of that, not only was I not bullied by the football players, but they actually invited me to work out with them in the school gym. And, while I don’t like to brag, I have been called handsome, and even rugged-looking by the girls.

I grew up on Chicago’s Miracle Mile. My dad was a broker with the Chicago Stock Exchange where he made a fortune. While I have never been called a genius, I was a straight A student and did remarkably well in math and science. That may be another reason I was never bullied. On several occasions I helped some of the football players and even the cheerleaders with their homework. So, even though I was a nerd, everyone considered me cool.

After I graduated high school at the top of my class, I attended MIT where I earned a degree in Engineering. I then attended the Wharton School where I earned an MBA. I was recruited by a number of Engineering companies, but after growing up in the cold winters of Chicago, then at MIT in Cambridge, Massachusetts, and finally at Wharton in Philadelphia, I decided to take an offer from a small firm located in Hialeah, Florida. I worked there for a year before I decided to open my own firm.

I had taken a course in aerodynamics while at MIT. After moving to Florida, several of the guys I worked with got me interested in golf. I woke up once in the middle of the night, and I had this idea in my head to design a more aerodynamically superior golf club. I’m not sure how that idea came to me, but I couldn’t get it out of my head and I couldn’t get back to sleep. I got out of bed and started working on my idea right away. A week later, I was satisfied with my design enough that I bought an empty factory in Coral Gables and went to work. After I had my first prototype, I went to the driving range to try it out. I was very pleased with the results. I then had a dozen more drivers manufactured and gave them to some guys at the golf course to try out. A week later, I met up with them and asked their opinion. Most of them were very pleased and admitted they had improved their drive. Some of them made some recommendations like using graphite shafts and improving the grip. I then made some new prototypes and asked some professional golfers to try them out. They were all very pleased. I talked some of them into using my new design and to wear my hats and golf shirts with my logo. As the old saying goes, the rest is history. My golf clubs can now be found in almost every pro shop in the country.

* * * * * * * *

It is now a couple of years later, and with the money in a trust fund my father had given me, and the money I had made from my new golf club business, I was a 25-year-old multi-millionaire. My dad taught me the importance of owning real estate, so I purchased a penthouse condo in a luxury high-rise on Miami’s south shore. Besides a beautiful ocean view, it had a great pool, and there was never a lack of beautiful women wearing skimpy bikinis. Oh, did I fail to mention that I’m hyper-sexual? In other words, I love pussy and can’t stand going a day without fucking someone. Luckily, I never had any trouble talking one of the girls at the pool into going up to my bed, even though I discovered most of them were married.

When I started my business, I hired a secretary. My first thought was to find the youngest, sexiest, most beautiful girl I could find. However, my business sense told me I needed someone who was experienced and competent. After interviewing several candidates, I ended up hiring Kathy. She was 42 years old and divorced. casino oyna However, she was very experienced, and according to her letters of recommendation, she was very capable. Despite her age, she appeared very fit and slim with a 36C bust and an amazing ass. During her interview, she revealed that after her divorce, she decided to get in shape, so she joined a gym, did Pilates, and ran three miles every morning. She said she was very self-conscious since her husband had left her for a younger, prettier, and sexier woman. I said, “Well, Kathy, if it was your intent to look younger, prettier, and sexier, I can tell you that you succeeded.”

She blushed, but she didn’t make a comment. I did catch her quick smile though.

For the first two weeks, she wore very conservative clothes that didn’t reveal anything, but try as she might, there was no way to hide the fact that she had great tits and an equally great ass. Every time she sat down I admired her shapely legs. My office consisted of my desk and chair, and two chairs in front of my desk for visitors. There was a sofa against one wall, and Kathy’s desk, chair and filing cabinet were all located across from my desk. I’m sure she was unaware of it, but she would normally cross her legs after she sat down, causing her skirt to ride up to about mid-thigh. I couldn’t believe that I was having thoughts of fucking a 42-year-old woman, but I definitely was.

The fourth week she was there, I asked her to come over to my desk and sit down in one of the visitor’s chairs. Instead of sitting in front of my desk, I asked her to move the chair so she was sitting in front of me. As was her habit, she crossed her legs, causing me to have impure thoughts. I started by asking her if she was happy working for me. I think she thought I was going to fire her because she immediately answered, “Oh, yes sir, Mr. Winston. I’m very happy here. The working conditions are good, and the pay is excellent. I hope I haven’t done anything to displease you.”

I smiled and answered, “No, Kathy, you haven’t done anything to displease me. In fact, I’m very pleased with your performance so far. I do have a few suggestions, though.”

“Yes, sir. Of course. What would you like me to do differently?”

I was thinking, “You can get on your knees and suck my cock”, but I didn’t say that. Instead, I said, “Well, first, I would like for you to drop the sir, and Mr. Winston. Please call me Randy.”

She looked surprised, but she answered, “Of course, sir…. I mean, Randy.”

Next, you may have noticed that I don’t always take lunch, but I have never seen you take a lunch break. Do you ever eat lunch?”

She said she did, but she didn’t want to leave the office unattended when I was gone in case someone called. I told her that was why we had voice mail. I told her, “From now on, I would like for you to join me for lunch at least three times a week. Would that be OK with you?”

Again, she seemed surprised. She answered, “Of course. If that’s what you want.”

Humm. Did I detect a somewhat submissive tone in her answer? She asked, “Was there anything else, sir, um, Randy?”

“Kathy, I know your work history. You have worked for several high-end businesses, most in a high-rise building. Now you’re working in a one-story factory. This office used to be the manager’s office and they had several people working in this same office. I know it’s not fancy like the other places you have worked. You may have noticed that we don’t have a lot of corporate types coming here for a visit. I guess what I want to say is, you don’t have to worry about impressing anyone. You dress very professionally. Don’t get me wrong, I think you look very nice, but what I’m trying to say is, I would like for you to dress a little more casually. I’m even going to implement casual Fridays, so if you want to wear jeans, that would be fine.”

She didn’t say anything, so I asked, “Any questions?”

“Um, just one. What type of clothes would you like me to wear during the week?”

There it was again. That hint of submission. “Kathy, don’t take this the wrong way, but you said you were self-conscious after your husband left. I want you to know that I think you are a beautiful, vivacious woman, and you have a great body. I think you should show it off. I’m not going to tell you what you have to wear, but I think skirts and sundresses would be fine. After all, this is Florida. If you want to wear sandals, that would be fine, but I have to tell you, you look great in high heels.”

She blushed again, and I again caught a hint of a smile.

“Now, would you like to go to lunch with me?”

“Okay.”

We walked out to the parking lot to my red Corvette where I opened the passenger door for her. I walked around to the driver’s side, and when I got in, I was pleased to see her dress had ridden up to mid-thigh. Either she didn’t notice or didn’t care because she sat there with her hands in her lap, looking straight ahead. I started the car slot oyna and then asked, “What type of food do you like?”

“Oh, I’m not too picky. Anything would be fine with me.”

“I usually just have a salad or a sandwich. Would Panera Bread be good for you?”

She looked at me and smiled, and then answered, “Anything that you would like would be okay with me.”

I hoped that was true. I planned to find out soon. We chatted during lunch and she seemed to loosen up a bit. I had a sandwich and she had a salad. We talked about fitness and I found out she worked out and ran every morning. I told her my building had a gym and I worked out most days and ran on the beach a couple of times a week. I had a thought, so I suggested she meet me at my place every morning, we could work out together, and then go for a run. She seemed reluctant, but I told her it was ridiculous for her to pay gym fees when she could work out with me for free, and, since I only ran about twice a week, she would be doing me a favor by encouraging me to run every morning. When she couldn’t come up with a cogent argument, she agreed. On the way back to work, I stopped by my condo and showed her my fitness center. She seemed impressed.

When we got back to the office, I asked her if she was okay with having lunch with me occasionally. She said she enjoyed having lunch with me and our casual conversation. I asked, “So, if you were okay with lunch, would you have dinner with me?”

She blushed again before answering, “Randy, you’re a nice guy. Probably the nicest boss I have ever had. It’s not that I wouldn’t enjoy going out to dinner with you, it’s just that I’m old enough to be your mother. Why on earth would you want to be seen in public with me? I’m sure you could have your pick of beach bunnies.”

I laughed before answering, “Yeah, you’re probably right about that, but like I told you before, I find you to be a beautiful, vivacious woman, and age is just a number. I would be proud to be seen with you in public. So, how about it? Would you like steaks, Italian, Chinese, or something else?”

“Thank you. You made me feel good about myself again. You’re the boss, so you choose. I would be happy with anything you choose.”

“Great. Since we’re trying to stay in shape, and we had lunch today, how about if we skip lunch tomorrow, and go to dinner tomorrow night? We’ll go to my favorite Italian place. Can I pick you up at 7:00?”

She agreed, and the next night, we had a great meal. I was happy to see she laughed a lot, and she seemed to be enjoying herself. When we got in my car, I convinced her come up to my condo for desert and wine. She seemed hesitant, but she finally agreed. When we got to my place, I told her to make herself comfortable while I poured us a glass of wine. I sat next to her on the sofa, and we clinked glasses before taking a sip. Since we had already shared a bottle of wine at dinner, she seemed to be feeling more comfortable with me. She took another sip of her wine before asking, “So, what did you have in mind for desert?”

I looked her in the eyes and answered, “You.”

She didn’t say anything. She just looked at me with a shocked look on her face. I asked, “Can I ask you a personal question?”

She just nodded her head. I asked, “Kathy, how long has it been since you’ve had sex?”

She was silent for a minute before answering, “Not since my husband left me. It’s been over two years. Not that we had much of a sex life before that. Well, I guess he did, just not with me.”

“Kathy, I don’t want to pressure you. I’m not speaking as your boss, so please don’t think you have to agree, but I would very much like to make love to you.”

She looked down with an embarrassed look. When she lifted her eyes to look at me, she sat her glass on the table. I took that to mean that she didn’t want to spill her wine when I reached for her. I took her hands in mine, then leaned forward to kiss her luscious lips. She didn’t resist when I put my tongue in her mouth. In fact, she returned my kiss. I kept our lips pressed together while I slowly ran my hand over her breast. Again, there was no resistance. I reached behind her and unzipped her dress to let it fall loose off her shoulders. She was wearing a black lacey bra. I again reached behind her and unsnapped her bra and let it fall forward revealing a beautiful pair of tits. When I started to slowly massage her left nipple, she let out a low moan, and her nipples hardened. Her large pink areolas responded by becoming tight, and I noticed little bumps appear around her now fully hardened nipples. When I leaned forward and sucked her nipple into my mouth, she responded by moaning again and arching her back, pushing her tit further into my mouth. I was rubbing her right nipple while sucking on her left one when I felt her put her hand on the back of my head as she pulled me in closer.

I now had a raging hard on. I reluctantly pulled my mouth off her tit and returned my mouth to hers for a very canlı casino siteleri passionate kiss. I said, “Let’s go to my bedroom.”

She responded by nodding her head. I noticed she was breathing heavily, almost panting. I helped her to her feet and led her to my bedroom where I finished undressing her. I sat her on the edge of the bed where I pulled her black lace panties down. She had a nice, trimmed patch of dark pubic hair, and I could smell her arousal.

I unbuckled my belt and let my pants drop to the floor. I almost never wear underwear, so my hard cock stood straight out. She gasped and I noticed her mouth was open and her eyes wide. “My god, Randy, that’s the biggest cock I’ve ever seen.”

That wasn’t the first time I had heard that. I’m not massive, but my cock is about 8″ long and fairly thick.

I kneeled in front of her and moved my head towards her wet snatch. She said, “You’re not really going to do that are you?”

“If you’re asking if I’m going to eat you, then yes, I’m really going to do that.”

“It’s just that I haven’t had anyone do that to me since I was in college.”

“You mean your husband didn’t eat your pussy?” I asked incredulously.

“No. He never offered, and I never asked. I know some men don’t like to do that.”

“Well, Kathy, if you will let me, I promise to make up for all the sex you’ve been missing.” With that, I put my hands under her smooth thighs and lifted them, spreading her open so I could put my mouth over her now drenched pussy. I inhaled deeply as I began to lick the tops of her thighs, then around her somewhat swollen pussy lips and then her clit. I sucked the swollen nub into my mouth. Kathy was lifting her ass and grinding her pussy against my mouth. As I began thrusting my tongue in her pussy, she started moaning loudly. My mouth and chin were getting soaked by her pussy juice. It tasted delicious.

She put her hand on my head, and moaned, “Oh my god, Randy. I can’t believe what you’re doing to me. I had forgotten how good that could feel.”

I was too busy to answer, so I just kept licking and sucking as I placed a finger in her cunt and started finger fucking her. She slammed her cunt against my mouth as she let out a high-pitched wail and exclaimed, “I’M CUMMMINNNGGG! OH FUCK, RANDY, I’M CUMMINNGGG!”

I lapped up as much of her warm nectar as I could before lifting my head and looking at her. Her eyes were closed, her mouth was open, and she was breathing hard. I marveled at the way her breasts were rising and falling, and her nipples were rock hard.

I moved up to hover over her and took a nipple in my mouth. It must have surprised her because she jumped and then chuckled before saying, “Oh my god, Randy. I can’t believe you did that. I can’t remember the last time I had an orgasm. You really know how to show a girl a good time.”

“If you thought that was good, you haven’t seen anything yet.” I took my hard cock and rubbed it up and down her pussy lips. It sounded like she was actually purring while I was doing it. I asked, “Is there anything else I can do for you?”

She chuckled again and said, “Yes please. Take that big monster cock of yours and put it in my pussy. Then fuck me like I’ve never been fucked before.” She spread her legs and smiled. I pushed my cock in about an inch and held it there a minute. I couldn’t believe how tight she was. When I felt her lift her ass off the bed, I knew she was ready. I thrust my cock into her waiting cunt and began pumping. After about four or five strokes, she moaned loudly, “Oh, god, yes, Randy! Fuck me! Fuck me hard! Never stop!”

“Damn, Kathy. You feel so good. We can do this as often as you want. I promise you will never have to wait to have an orgasm ever again.”

She was moaning and lifting her hips with every stroke I took. At first, I was trying to be gentle, making sure she could take my length and thickness, but it seemed as though she was not only able to take it, she was actually wanting more.

I started pumping my cock into her as deep as it would go. She continued to lift her hips, meeting me thrust for thrust. It only took a few more thrusts before she cried out, “YES! I’M CUMMING AGAIN. Oh fuck, I love the way you fuck me!”

That was all I could take. I felt my balls tighten. “Kathy, I’m gonna cum.”

“YES! CUM IN MY PUSSY! FILL ME UP WITH YOUR CUM!”

Fuck me! A couple of hours ago I was wondering if I would be able to talk this mature, seemingly prim and proper divorced woman into letting me fuck her. Now I was thinking I had unleashed a monster. It seemed as though she couldn’t get enough. Well, if she wanted to get fucked, I planned on fucking her as much and as often as I could.

“Oh, shit Kathy. I’m cumming baby. God you feel so good.” I then let loose a massive load of hot semen in her warm, wet, clenching cunt. I could feel her cumming again. She was having another orgasm.

I collapsed next to her and we held each other while we waited to return to normal breathing. I was looking at her beautiful face when she looked up at me and smiled. “Damn! I haven’t been fucked like that since …. Well, I was going to say since college, but I changed my mind. I don’t think I’ve ever been fucked like that.”

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