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In January of 2012, I semi-retired from the small, but highly lucrative software engineering company I’d started in 1986. I’d developed several highly specialized security suites used by the Department of Defense and Department of Energy, as well as private clients. It had been quite a ride in those 26 years, but I was beginning to feel the strain it had taken on me. For the first time in my life, I was beginning to feel my age. I’d made a pile of money and with some smart investments, I became rather wealthy. Not Warren Buffet or Bill Gates wealthy, but money was something that I hadn’t thought of in many years.

The first week of January, I called my ten employees together for a meeting. It was the usual time I gave everyone their yearly bonus checks, as well as a little pep talk about hard work and perseverance. This time though, I gave them their bonus checks and told them from here on out, they’d be working for themselves. The company would now be employee owned. My very first employee, Eric Jensen, would be the new president and CEO. He had started with me as a young, bright eyed engineer, twenty-two years before. He was the sort of person that would have been successful at anything he tried.

The existing employees would buy me out over a period of ten years, which could be extended if necessary. Knowing Eric, the earnings capacity, and growth potential, I knew I would be bought out as early as possible. That was fine with me, as I wanted the bulk of the company in my loyal employee’s hands as soon as possible. I added one small caveat, I would retain 25% of my shares that would return to the trust upon the death of both myself and my younger sister, Amanda. The resulting balance would go to my niece, Kassie. I wanted to ensure good income for Amanda and me during our older years, while keeping the majority of my assets to take care of enjoying retirement, charitable contributions and unexpected circumstances. I also planned for Kassie to have a nice nest egg.

My retirement would be official February 1. Everyone was very excited by the opportunity I had suddenly given them. Eric was obviously the most excited. I knew he’d do just fine.

When it finally arrived, there was a huge sense of relief. I still planned to work one or two days a week, just to keep myself familiar with what was going on. The first two weeks were tough breaking the routine of being at the office at least 12 hours a day. The change really hit home as Eric took over my old role. I reminded myself that everything was in good hands and that he would do just fine. By the 3rd week, I was getting accustomed to sleeping in and taking a leisurely ride on one of my bicycles five mornings a week.

I’d worried more about the transition from a personal standpoint than a business one. I was 48 years old, single and suddenly had no real focus in life. My personal life was complicated to say the least. The only two women that were a constant presence in my life were Amanda and Kassie. They were my world, and there was nothing I wouldn’t do for the two of them. But there was more to it than that.

Amanda was 14 months my junior. We’d finished raising one another after our parents were killed in an auto accident the summer after my freshman year of college. Neither Mom or Dad were particularly close with their families. So, Amanda and I found ourselves suddenly alone. It was a tough time considering I had a year of college under my belt and she’d just graduated from high school.

We ended up selling everything Mom and Dad owned, plus using our college funds and their life insurance policies to cover their business debts. Little did we know at the time, this was due to my dad’s business partner transferring mutually shared and his own debt onto my dad’s ledger. He’d also taken several of my Dad’s patents as his own. We were just kids, and after almost twenty-five years of partnership with my dad, he’d really fucked us. My dad’s accountant finally figured it all out, but we certainly didn’t have the money to hire an attorney at the time. I swore to Amanda that I wouldn’t rest until we got Mom and Dad’s money back from the bastard. As soon as my software company was going well enough I could keep my head above water, I hired the best attorney I could find. A few years later, Dad’s former business partner ended up settling with Amanda and I for approximately $7.5 million dollars.

Unfortunately, that wouldn’t come until much later and we had to get through college first. Amanda and I shared a bedroom in a house I’d rented with four other guys. I had a job as a research assistant, and I was moonlighting writing all the code I could get my hands on. The programming was good money, but never enough to completely cover our tuition plus room and board. I finally relented and she got a job at a local bar that had just opened. I was not a regular at any of the college bars, but I thought I’d go in one night and see what it was like. To my surprise and horror, it was a strip joint. Thankfully, Manda wasn’t hack forum on the stage, but she was waiting tables in just tiny panties and a cut-off shirt that barely covered her breasts. I was immediately determined to make her quit.

The next morning, I talked to her about it, but she was adamant.

“Look, John. I go to bed and you’re on your computer working to support us. I wake up and it’s the same thing. I can do my part, I don’t mind.” She argued.

“Manda, I just don’t like it. You’re fucking half naked.” I said. It was quite the departure from her personality. She was amazingly intelligent and beautiful, but also very shy. She dressed conservatively and looked the part of the book worm.

“I know, but I made enough in tips the first week to cover the rest of our rent. I can have our utilities this week.”

“I still don’t like it though. It’s just not you.” I persisted.

“I know, but you’re already working yourself to death just to keep up with our tuition. I really don’t mind it. It’s actually really fun working there.” She said. I loved her and trusted her. If she was okay with it, I could be too and I let it go at that.

“Please, promise me you won’t start stripping there.” I said, as I conceded.

“I promise, John.” She said as she hugged me. We both had a good laugh about that.

One night in late October that first semester, Amanda was studying and I was working on some code. I was focused on my work and hadn’t been paying much attention to her, until I heard her softly sobbing. I immediately walked over and put my arm around her.

“Hey, what’s wrong?” I asked.

“It just hurts, John. We’re completely on our own now. Sometimes it really hits me hard.”

“Manda, I know, but we still have one another. I’ll always be there for you.” I promised.

“Yes. I don’t know what I would do without you.” She stood up and hugged me tightly.

“I feel the same way. We’re just going to have to get through this together, honey.” I said.

“Yes, we will.” She kissed me on the cheek. I smiled at her as she pulled back. She surprised me by then kissing me on the lips. I was shocked, but I didn’t have long to contemplate it, before she did it again. This time I felt her tongue trying to fight its way through my lips.

“Uh, Hey. What are you doing?” I asked in confusion.

“John, I don’t want to feel this way any longer tonight. I want to feel something else.”

“Manda, we can’t do that.” I protested, knowing exactly what she meant.

“Yes, we can. Kiss me, John.” Her lips returned to mine. I hesitated. She was upset and didn’t know what she was thinking, I told myself. Our lips met and she held me even tighter. Her tongue once again probed my lips. I granted her entry and our tongues met and twirled.

I was surprised to learn that my own little sister was the most passionate kisser I’d ever met. She released me from her embrace and quickly unbuttoned her blouse revealing her perfect, bare breasts. She took my hands and pulled them to her chests. Her breasts felt almost electric in my hands. I rubbed them gently and teased her hard nipples with my fingertips as we continued to kiss. She frantically pulled my t-shirt over my head and pulled me close to her again. I loved the sensation of holding her against me.

I found that despite our relationship, she had me more turned on than I think I’d ever been. Her right hand was between us and unbuttoned my Levi’s. They were soon around my ankles, along with my briefs. She stoked my throbbing cock briefly, before removing her shorts and panties. She led me to my bed and pulled me on top of her. I felt her reach between us and grab my rock-hard cock, directing it toward her warm, inviting wetness.

“Manda, are you sure about this?” I asked, between passionate, lusty kisses. I felt like I had to give her one last opportunity, even though I was well beyond the point of no return.

“Mmmm yes, let’s just do it, John.” She replied.

“I don’t have any condoms.” I said.

“I’m on the pill.” She replied. Her hands grabbed my hips and she pulled me deep inside her.

“Oh,” we gasped in near unison as I bottomed out.

“God, that’s really good, John.” She moaned.

“Yeah, it is honey, but you’re sure though?” Despite feeling the need for confirmation, my hips were thrusting, sliding my cock in and out of her wonderful, silky wetness.

“Yes, I am. We love and care about one another, I’ve wanted this for a long time.”

“You have…” I started. She raised her index finger to my lips.

“Shush, let’s just enjoy it. We can talk later.” She said.

I knew we would need to talk, but satisfying our needs came first. I was pumping in and out of her with vigor. She wrapped her shapely legs around my waist and smiled as she looked up at me.

“Thank you, John. I love you so much. You’ve always looked out for me and took care of me.” We were staring into one another’s eyes. I could only nod, as my mind swam with thoughts of what we were doing. “Oh, god, you feel so good inside me!” She groaned.

I was panting as I thrusted in her. “You feel really great, too. Oh Manda. So, fucking good!”

“Oh, yes. Yes, John. Oh, I can’t believe it. I think I’m going to cum. I’ve never came this fast.”

“Good, because I’m about to fucking explode!” I gasped.

“Then do it. Do it John. Give it to me, baby.” She groaned as she orgasmed.

“Mmmm, oh, Manda. I’m cumming, I’m cumming.” I thrust one final time and filled my little sister with everything I had. She pulled me down and kissed me.

“That was amazing.” She smiled.

“Yeah, it was!” I smiled deliriously.

“No regrets?” She asked.

“No. Do you?” I replied.

“None. It was wonderful.” She answered.

We kissed for a long time and then she moved to get up. I watched as she put her clothes back on. Finally, she looked back at me. I was looking at her curiously.

“What?” She asked.

“I don’t really know. I mean we just made love. Now you’re up and dressed, like nothing happened.” I said.

“I need to finish my finance homework and I have a paper to write for freshman comp. You have work to do too, right? There will be plenty of time to talk this weekend. We’ll have the house to ourselves. The roomies are all going camping, remember?” She arched her eyebrows.

True to her word, we did talk, and make love, repeatedly that weekend. Manda and I were lovers for the next two and a half years. Just before my graduation, I sat her down and we had a long talk. I told her that I loved her more than anything and enjoyed every moment we shared, but I felt that we both needed to move on. I’d often felt during my last year of school our relationship was somehow holding her back. Neither of us had been on a date in all that time. I felt that she needed to explore and that with me being her constant emotional, as well as physical companion, that would never happen. I explained as much to her during our talk.

“John, thank you for saying that. I’ve been thinking I was holding you back as well, but I couldn’t bring myself to tell you. I didn’t want it to end, it’s been so special.” She gave me a big hug and a long lingering kiss. We held one another as we both cried. When we both finally stopped, there were smiles on both of our faces. We were just brother and sister again, albeit with a love and understanding that few siblings ever knew.

Little did we know, another family tragedy would reunite us again, years later.


I’d married the year after graduation from college. She’d seemed like the perfect girl. We had a lot in common and got along great. Unfortunately, she expected me to be more successful than I was at the time. Despite all my hard work, I had not instantly become the Silicon Valley multi-millionaire she expected when we’d met. She left me shortly before our second anniversary. A year or so later, I was making more money than I knew what to do with. Naturally, she called me, offering to leave her new husband for another chance. I told her firmly, I was not interested and wished her the best of luck.

I’d remained a bachelor in the intervening years. I’d met many wonderful women in that time, but I was clear with them I was only interested in companionship. I realize now, that I hurt a lot of great women, but I was callous. When I decided in my late 20’s that I was never going to remarry, I had a vasectomy. I finally admitted to myself that most of my issues revolved around the fact these women were not Manda. By the time I realized this, it was too late.

In 1990, Amanda married a doctor, Ryan, fresh out of medical school. She had graduated with a degree in accounting and was already working her way up at a large firm in Chicago when they met. Ryan and Amanda were the perfect couple. You could see it in the way they interacted, I admitted with envy. When Kassie was born in 1994, I was caught between feelings of happiness for them and sadness. Soon, I convinced myself that the past was gone and I needed to be happy for the life they were lucky to share.

Unfortunately, their happiness was not to last. Ryan was diagnosed with glioblastoma just before Kassie’s second birthday. He was gone by her third. His passing left Manda a widow at 31 and in a dire financial situation. She had spent the majority of her portion of the legal settlement from our parent’s estate on helping Ryan establish his medical practice. There were also tremendous medical bills for experimental treatments during his fight with cancer that were not covered by insurance. Regrettably, Ryan never established adequate life insurance coverage for Amanda and Kassie.

I was making serious money by then, so I stepped in to help her out. She was my sister despite what we’d shared before. I set up a fund for Kassie’s education, and to give her things that I knew her dad would have provided for her. I tried to ensure she never wanted for anything. I was the doting uncle, but in a way, she became the daughter I never had. I set up a fund to help Amanda with finances as well. About a year after Ryan passed, Amanda asked me to come to Chicago for a few days. She had a few final things to settle with his estate and she wanted me to be there as a second set of eyes and ears. Kassie was visiting Ryan’s parents in Ohio. I knew that I also needed to be there for emotional support as this was likely the final chapter of her losing her husband. She had remarked several times that the whole ordeal had been like losing Mom and Dad again, only in slow motion.

I caught a red eye flight from the west coast and she met me in a cab, which took us to her attorney’s office. We had a lengthy meeting regarding the final status of Ryan’s estate. Unfortunately, there was a discrepancy in the amount owed on the building Ryan’s medical practice was located in. The appraised value was far below the amount owed and the financing company had called the balance due, to the tune of $2,500,000. We’d expected to be able to refinance the building at a more competitive rate, not this. I looked to my left at Manda. She looked like she was about to wilt. I was about to explode, because something wasn’t right.

I switched from caring brother to shrewd asshole in an instant. I asked Manda to wait outside for a moment. I didn’t want her to see my ugly side. The attorney representing the finance company suddenly looked uneasy.

I knew that Ryan and Amanda had put a large sum of their own money into refurbishing the building in question. It was a burned-out shell in one of Chicago’s roughest neighborhoods when they bought it. Ryan’s dream had been to open a practice in an area typically underserved by quality medical care. He had recruited many younger medical professionals to join him. I had contributed, but Ryan and Amanda consistently refused to let me finance the whole project. I understood their feelings and agreed to let them seek other donors and investors to see the project through. As I sat in the office fuming, I wished they’d let me help them more. Once Amanda was outside the room, I went to work.

“So, let me get this straight,” I glared holes in the attorney for the finance company. “You say the building as it sits, completely refurbished, fully occupied with paying tenants is worth $250,000?”

“Yes, Mr. Brown, that’s correct.” He replied smugly.

I leaned forward in my chair. “You have got to be out of your fucking mind! That building is worth $5 million, period.”

He got a concerned look on his face, “Mr. Brown, the appraisers…”

“Your appraisers are intentionally trying to fuck us.” I interjected.

“No, it’s fair market value.” He added, lamely. I doubted he even believed what he was saying.

“Okay, fair market value. How about this, why don’t I write you a check right now, for $2.5 million, I keep the building, and your client goes and fucks themselves.” I said glaring at him.

“No, Mr. Brown. It doesn’t work that way. We’d have to have the property fairly appraised and….” He stammered.

“So, you’re admitting it was unfairly appraised to begin with?” I asked. I gave him an icy stare. His eyes blinked repeatedly.

“Uh, no, that’s not what I’m saying, Mr. Brown.” He sputtered. He was visibly uneasy.

“Then, what are you trying to say?” I asked forcefully.

“I’m afraid I’ll have to speak with my client about this matter.” He replied, playing for time.

“I suggest you talk to them immediately. Cole Palmer does the evening news for WGN. He’s a close friend of my mine. I’m pretty sure your client would hate to see a story about them foreclosing on a medical center located in underprivileged neighborhood. Don’t you?”

“You can’t bargain with me that way, Mr. Brown!” He insisted.

“That’s funny, I already have.” I replied. “I expect an answer in an hour. Otherwise, you will be hearing from my attorney, Harlan Samuel.”

“Harlan Samuel?” He said, surprised. “He represents you?”

“Yes, for over 20 years.” I said.

Jim, Amanda’s attorney, finally spoke. “Bob, you can use the office next door.”

Bob stood up, completely flustered. Without a word, he left the office.

I looked over at Jim, who was shaking his head. “That took an unexpected turn.” He said.

“Yeah, he thought we were going to take it lying down, didn’t he?” I asked.

“He did. I just hope his client sees it your way.” Jim said.

“It’s in their best interest. Cole lives for this sort of thing. So, does Harlan.” I smiled.

“Yes, I’m sure they do. For a California guy, you sure know how to do things the Chicago way.”

“I thought being a difficult asshole was the same everywhere.” I laughed.

Manda walked back in the office. Jim explained what had happened.

“I thought he left looking less sure of himself,” she replied. She looked at me and shook her head. I knew I was going to get a talking to, but after all she’d been through, there was no way in hell I was going to let anyone push her around.

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