Addison and Penn
by BigJW
Copyright© 2025 by BigJW
Incest Sex Story: Addison loses her job during the COVID-19 pandemic and needs help from her brother Penn to help her start a new career as a day trader like him. The best way to survive the pandemic was to quarantine themselves together for her training. Their relationship would never be the same.
Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa Reluctant Romantic Heterosexual Fiction Incest Brother Sister Cream Pie Safe Sex .
My cellphone vibrated on my dinner table just as I was completing my evening dinner. I was glad to see my sister Addison’s smiling face on the display rather than an unknown number. “Hey sis, what’s up?”
“Hey, Penn! Just catching up. You doing okay? Are you keeping yourself quarantined?”
“Are you kidding me? I haven’t seen a human being for at least two weeks. I even make the local supermarket delivery driver leave the boxes on my front porch without opening the door. I tape their tips to the door in an envelope.”
“Yeah, we need to find an answer to this pandemic immediately,” she said. “That’s kind of the reason I’m calling.”
“Oh, my god. Are you okay?”
“Yes, I’m fine, I’m not sick. But two of the senior partners just tested positive.”
“Is your firm sending some of the lawyers to work from home? I read that a lot of law firms are doing that.”
“Yes, they sent me home. The problem is, I was sent home permanently. They laid me off. I was hired in January and three months later I’m gone. I saw it coming, and I get it. I was the last one hired. It still hurts, though.”
“When did this happen?”
“About three weeks ago. I was in shock for a day or two and after that I started looking for something to do. The probability of getting hired by another law firm right now is pretty low. My old stats professor would have said ‘the probability of continued unemployment is approaching one.’ But, I’ve gotten through the panic stage and I think I might have a solution. That’s what I’m calling about.”
“Okay? Consider me intrigued. What are you going to do?”
“Are you sitting down?”
“Yes,” I said.
“This is a big ask, Penn. Before I even say anything I want you to know that you are not obligated to do what I’m about to ask you.”
“Okay, I’m listening.” I was certain at that point that she was going to ask me for a loan.
“Here goes. It’s a two part request, really. The first part is that I’m asking you to coach and train me to be a day trader like you. After I thought of it I just knew that I need to do this. Remember, my undergrad major at UVA was finance. That’s why I went into corporate law. I can do this. I just need a coach.”
“Wow, that is a great idea. I know you have bills to pay and a student loan to repay. However, I need to warn you that you shouldn’t expect to start seeing substantial income for four to six months. It is definitely not instant cash flow. I hope you are prepared for that.” There was no response, which worried me. I let it drop. “But, I’d be happy to be your coach. What was the second thing? Wait, let me guess. You need the $25K seed money to open the brokerage account?”
“Well, I guess there are actually three requests. Yes, I definitely need a small loan from you to open that account. But the third ask is the one that I’m most concerned you might not be willing to do.”
“Just spit it out, Addison. What is it?”
“Would it be possible for you to let me live there with you for a while? In your house? Just say no if you don’t want me to! I mean it. I can do this on my own from here in Dallas but my roommate just bailed on me right after I got laid off and I’m not sure I can cover my rent for more than three or four months.”
I immediately knew that it was a great idea. I also knew that this was a great opportunity to give my sister a little bit of a hard time before giving in and agreeing. Sibling rivalry in action. “Hmmmm, I don’t know,” I said doubtfully.
“Awww. Why not? Do you have someone else living there? Even if you do, I promise to be quiet. The two of you won’t even know that I’m there most of the time. Only when I’m in the pool. I promise.”
“No, it’s not that,” I said. “No roommates here. Actually, the last girl I dated had a situation similar to yours. She was a waitress, and you know that service industry employees were the very first to be let go. She moved back into her parent’s house in Chicago. No, it’s not that.”
“Then what? I know that your house has at least three bedrooms, and even if you use one as your office, that still leaves one for me, right?”
“Actually, the house has four bedrooms, plus I have a study downstairs where I have my office ... It’s not that.”
“Then what is it? I really, really want to get out of Dallas. It’s only late April and it’s already like a furnace here. I’m really looking forward to New England weather again. I should have never taken this job here in the first place. Come on, what is it?”
“Hmmmm. I don’t know. Oh, I’m just fucking with you, sis. I just wanted to hear you beg a little. Of course it’s a great idea.”
“Oh! You asshole. I thought you were really going to say no. Jerk!”
“Oh, really? You knew from the first time you had the idea that I would say yes.”
“Yeah, that’s true. You’re my big brother. You’re morally obligated, and maybe even legally obligated, to help out your little sister.”
“Legally obligated? Now I’m wondering how good a lawyer you are. Maybe a move to finance is a good idea.”
“Oh, shut up.”
“So, when are you going to make the move?”
“Immediately, if not sooner. Are you okay with me showing up in a couple of days?”
I couldn’t see any reason why not. “Yeah, sure. Are you going to drive here?”
“Yeah. I need my car there. Google Maps says that it’s a little over twenty-six hours from Dallas to Worcester. My 4Runner back seat folds flat for lots of cargo, with enough room left that I can spread out some blankets to make a narrow bed. I thought I would drive eight to ten hours or so, stop for a deep sleep, and then get back on the road for another eight to ten. Lather, rinse and repeat until I’m at your door. I’ll be ripe and smelly when I get there. When I arrive just point me to a shower.”
“Definitely.”
“By the way, and this might be classified as TMI ... maybe not. I plan on finding secluded areas to stop to take a pee and poopoo. I’m not even going to any public restrooms. I’m also taking enough food from my apartment so that I won’t need to stop for meals. I know that I’m not sick right now since I’ve been self-quarantined for the last three weeks. Your email a month ago said you were going to totally quarantine, so both of us should be healthy enough that we don’t have to avoid each other like we’re lepers when I get there. It will be good to not wear a mask all the time, and to actually touch a real person again. I could really use a hug right now.”
“After the shower, please.”
“I promise.” She laughed.
“No, I know what you mean. These are strange times. I feel like a total hermit. You coming here is actually going to be really nice. It seems like we’ve hardly seen each other since you went to law school. Like, once a year or so. I’ve missed you.”
“Me too, bro.”
“Do you need anything before you leave? Need a small loan for travel money?”
“No, I’m not that destitute. I have to pay a ton to break my lease, but I will be okay. Thanks for asking.”
“Of course. Let me know.”
“I will. Okay, I will let you go. I need to call my landlord and confirm that I’m leaving. I think I can do that today and get packed. All I have is my clothes and a bike. I have a furnished apartment so I don’t own furniture. If my stuff doesn’t fit in the 4Runner I’m leaving it. I think I will be on the road early tomorrow morning.”
“Okay, but don’t overdo it. Safety first.”
“I won’t. I’ll call you when I leave.”
“Thanks. By the way, I could also really use a hug.”
“I love you bro.”
“Love you too, sis.”
I heard my cellphone vibrating on my desk a little before 11:00 AM the next day. Seeing Addison’s pretty face gave me a smile. I’d just finished research into a possible trade and was ready for a break. I answered it, “Are you leaving soon?”
“I’m in Memphis.”
“Memphis?! Wow, what time did you leave this morning?”
“I left my apartment about five so that I could get outside the city before rush hour, but there really wasn’t a rush hour. It seems like there are a lot less people on the roads these days. I’m making great time.”
“That’s great. Make sure you stop if you get tired.”
“I will. I still have most of my coffee in my Thermos. I haven’t felt any drowsiness at all. I’m doing fine. I’m thinking of taking my bike off the rack for a trail ride in an hour or so. That should get the travel cramps out of my legs.”
“Good idea. By the way, I hope you’re talking hands free since I can hear that you’re definitely on the road right now.”
“Yes, of course. Hey, I see a good place to pull over ahead. I’m going to do a search for a bike trail and maybe eat something now. Have a good morning, Penn.”
“You too, Addison. Be safe.”
Text message from Addison received at 7:22 PM that evening - ‘Still making gr8 time. Stopped 4 sleep at KOA in Wytheville, VA. I rode my bike for about 15 minutes and now I’m in the back of the 4Runner ready 4 sleep. Will call-text in the morning. Luv ya. Addison’
Text message from Addison received at 8:11 AM the next morning - ‘Slept like a rock & woke @ 3AM 2 get back on the road. GPS says I should be @ your house 2PM this afternoon!!!!! Ready or not, here I come!’
Knowing that Addison was going to arrive in the afternoon, I wrapped up work before lunch so that I could prepare her bedroom and the rest of the house for her arrival. The room I was giving her had been my primary guest bedroom because it has a private bath and is on the opposite side of the house from my master bedroom. Dividing them were two smaller bedrooms with a shared bath between them. The larger of those would be her office. I placed a delivery order with Wegman’s to stock up on necessities that I was low on and for special foods that I knew that Addison liked. They were having a special on fresh cod loins so I ordered a pound for a great first dinner together that night. I was actually really excited and even a little nervous about seeing my little sister again.
Just as she had predicted, I heard my doorbell a few minutes after 2PM. I pushed aside the curtain in my office front window and looked out onto the front porch. She saw me and started bouncing up and down in excitement. “Let me in!” I was happy to. When the door opened she burst into the room, leaving her carry on bag on the porch, and threw her arms around me. “Penn! Oh, my god, it’s so good to see you again.” She hugged me tightly and kissed me on the cheek. “I don’t care how smelly I am from the drive, I want a hug!”
“Me too. Wow, I can’t believe you’re here. It seems like 15 minutes ago when you revealed your great plan, and now here you are. I can’t believe my eyes. You look really good. Staying fit, I see.” She had always been athletic and fit, and it was good to see that she was still taking care of herself. “I have an elliptical and a free weight set in the bonus room over the garage so you can use those if you want. It would be great to have a workout partner again.”
“Yes! I need that! With the pandemic I’ve had to give up the gym membership and replace it with YouTube yoga, but I did find a great channel that I really love.”
“Well, it’s working for you. Hey, I know that you need to freshen up. Your room is the one at the end of the hall on the right. Cream color bedspread. You can’t miss it. Give me your keys and I will unload your car while you are in the shower.”
“Oh, thanks. Okay. Luggage goes into the room with me so just bring those inside and I can take them up later. The boxes can stay in your garage for now if you have room.
It only took a few minutes to get her unloaded. I took her luggage upstairs and placed them just outside her room. I was surprised how little there was. When I got back downstairs I grabbed a beer and went out onto the patio by the pool. When I heard the door open I called out, “There’s cold beer if you want one.”
A moment later she was sipping a Sam Adams seated next to me. She said, “Penn, you’ve really done well for yourself. Your house is amazing. In case I’ve never told you before, I’m really proud of you.”
“Thanks. I’m really happy here. When I bought the place a few years ago I knew that the mortgage was going to be a challenge but now the market has grown so much that I’m very, very glad that I took the risk. And with interest rates so low it would have been crazy not to.”
“Have you been thinking about how this is going to work with me staying here?”
“Do you mean living together, or the learning a new profession part?”
“Both! This is going to be a change for both of us. You probably more than me. I’ve lived with a roommate since freshman year, but you’ve been alone for what, six or seven years?”
“It will be fine. You’re my sister. We lived in the same house for most of our lives.”
“I can see that you’re very tidy,” she said. “You always were. Even as kids you liked to be neat and organized.”
“I’ve found that being organized helps me stay focused in my trading. Here’s your first lesson. You will learn that when you work from home in any job, one of the biggest challenges is resisting the distractions that are all around you. Laundry that needs to be done, dishes that weren’t taken care of after breakfast, mowing the lawn. Something you need at the hardware store. All those things that cry out, demanding to be done, so that you don’t focus on your job. You will see. You have to eliminate those distractions, and to do that you will need to be more disciplined than you’ve ever been. So, what I do is always stay ahead of things. Stay proactive. Do the dishes when it is time to do dishes, immediately after the meal. Pay the bills online at the same exact time every week. Cut the grass on Saturday, no exceptions. That way, when it is time to work, I work. There is nothing to pull me away and distract me.”
“I can do that. Help me get used to it, okay? Be patient with me at first until this new discipline becomes a habit like it is with you.”
“Exactly! You got it! It needs to be a habit. Stick with it for twenty eight days and it will change your life.”
“I will. I want you to be proud of me. I want to be like you, bro.”
Since I didn’t go to grad school after completing my bachelor’s degree, and with our two year age difference and her going to law school, I entered the work force a long time before she had. I know she felt there was an awful lot that I could teach her. “Aw, sis. I’m already proud of you. I always have been. And, by the way, you’ve always been an overachiever in everything you’ve done. That’s already a habit for you and it’s not going to change. You are going to do great.”
“When do we start, boss?”
“Tomorrow morning. But, now it’s beer time, and you’re one behind me. Catch up, lightweight!”
The first day of Addison’s training was Friday. She told me later that she had set her alarm for 6:30, confident that she would have ample time to prep for the opening market bell at 9:30. When she had completed her shower and marched down the steps at 7:30 on her way to the kitchen she passed my office and was surprised to find me not only in my office, but on the phone with someone and obviously working. I could tell she was surprised by the look on her face. She didn’t know my work hours because she hadn’t asked the day before. She made her way into the kitchen and poured herself a cup of coffee. I found her finishing up her first slice of wheat toast when I went into the kitchen.
“Hey, sleeping beauty. Good morning,” I said. “Sleep well?”
“Yeah, I slept great, thanks,” she said. “Penn, what time do you start work? I’m sorry I forgot to ask.”
“Don’t worry about me, kiddo. You’re not going to match my hours. For you, right now, the important thing is to learn. And, there is a ton of administrative stuff to do to set up your business. I will get you pointed in the right direction. Trust me, you don’t want my hours. Do you really want to hear them?”
“Yes, definitely. How bad can it be?”
“My day starts at 3AM.” I paused to allow her to react.
“Three?! Why? The market opens at 9:30, right?”
“The US market opens at 9:30. But when the London market opens it’s 3AM here on the east coast. When the Tokyo market closes it is 1AM, and sometimes I get up that early, but that is rare. My particular range of trades is in the international markets, and I find that being tuned in at the opening and closing bells helps me out a lot. My usual routine is to get up a little before 3AM, get a couple of hours of work in, and then get a one hour stretching and cardio workout. Then it is into the shower and down to breakfast before 7AM. I get some of my best work done before the New York market bell rings.”
“That’s insane. By the way, who were you talking to so early when I came downstairs? Some other lunatic up before sunrise?”
“Actually, that was someone in London. It was about noon there.”
She shook her head. “I’m sure you plan on working until 4PM when the New York markets close, right?”
“At least.”
“Maybe I need to reconsider this day trader idea.”
“What else am I going to do? I’m in quarantine. I’m not watching Netflix for eight hours a day. And remember; this is my chosen business plan. You don’t have to do international. You need to find your own niche. That’s actually part of my lesson for today. Find something that will work for you. You can even have fun with it.”
“Okay, I get that, and I am definitely relieved that you don’t expect me to be up at 3AM each morning shadowing you for fifteen hours. You’re a madman, bro.” She went silent for a moment and I could see that she was working on a thought. She said, “Hey, do me a favor. There’s something that I’ve been wondering about. If you feel comfortable doing it, can you tell me how much you made last year? You don’t have to, of course. I know that’s really personal, but it must be a lot for you to work this hard, and right now I can use some motivation.”
“Are you sure you want to know?”
“Definitely. Hit me.”
I accessed my 2019 tax return in my computer and opened it. I found my 1040 and expanded it so that the block with my income nearly filled my monitor. I said, “When you are ready, walk around here to look at my tax form. By the way, don’t tell mom and dad about this. Or anyone else.” I minimized the form until she was in position.
“Okay, I’m ready. Show me.”
I reopened the form and it filled the monitor. The expanded income block read: 1,320,045-.
Addison saw the number and looked at it with a confused look on her face. I believe she thought that she was looking at the wrong number. Then it hit her. She was looking at the correct number. He jaw dropped like she’d been punched. “Is that for real?!”
“Yes.”
“You made more than 1.3 million last year?”
“Yes.”
“Penn! Oh, my god! I knew you were doing well but I had no idea. You’re crushing it, bro! Wait, is this an anomaly? Or is this the culmination of a lot of years combined?”
“Nope. I’m on track to beat that number this year. Last year I was just under 1.1”
“Wow, maybe you really should teach me this international strategy you’re using. I could work those hours for that much money.”
“I know, right? And like I said, what else am I going to do with my time during this fucking pandemic? Travel?” I don’t think so. The pandemic will pass, and when it does life will change. I might ease up then. And the cool thing is that lately I’ve been trading with much less risk than I used to, not more. I’ve hit a sort of sweet spot with my business. You can get there also if you work your ass off for a while.”
She stood up straight, like she was a soldier at attention. “Tell me what to do, sensei.”
Addison did work her ass off. Her work ethic was off the charts. She used my seed money to get her brokerage account set up and completed the mountain of administrative requirements. We had office furniture, a new computer, and all the equipment and supplies she would need delivered to the house. She learned trading principles and strategies. She read books, took online courses, and studied the financial markets. She developed her trading plan, outlined her investment goals and risk tolerance, and came up with specific strategies. She was on her way. She had been doing this while following along with some of my trades, just to see the actual mechanics of processing real trades. She started trading with small positions. I taught her how to continuously review her positions and her resources so that she could adapt new strategies if needed.
She lost money. And then she lost more money. Thankfully, it wasn’t a lot because her positions were small. But she learned and she worked hard. She got better. She made some money, and then she lost some money. I was definitely bankrolling her in the beginning but I didn’t care. She is my sister and I love her. I knew she would get it. And the pandemic rolled on.
From a domestic perspective Addison and I were doing great. She totally came to accept my very regimented daily routines. Weekends were our fun days. We spent a lot of time in the pool, and we weren’t total hermits. We went out most Sundays for a hike or mountain bike trail ride. It’s just that we didn’t interface with anyone. If we saw someone on a trail we needed to pass, we went off trail to make the pass. We didn’t eat out or go shopping. We got everything we needed from Amazon or Wegman’s Supermarket home delivery. We were adamant that COVID-19 was not going to get us.
By late July Addison was making some money and was about even overall. That was when she had her first big successful trade. It put her $80,000 on the plus side overall. She really understood how the game was played, and how lucrative it could be if she was willing to grind it out and work hard. In the afternoon of that big day she walked downstairs and peeked into my office. I wasn’t directly involved with something that couldn’t be postponed, so I invited her in. “Hey, Addison. What’s up? Come on in. I’m ready for a break.”
She was quiet as she walked around my desk. When she was close to me she said, “Stand up, please.” She started to smile.
I stood. “What’s going on?” I started to smile also. She then put her arms around my neck and pulled herself to me in a very tight embrace. It was impossible to not hug her back. She felt wonderful in my arms.
“Thank you, Penn.” She held the embrace for a wonderful moment and then pulled back a little and looked me right in the eye. “Thank you!”
“Thank you for what?”
“For everything. For teaching me, for supporting me, for believing in me. For everything. You’ve changed my life.” She kissed me then, right on the lips. It was an innocent kiss, one of love and affection. But, it was still a kiss, and the effect it had on me was immediate. “I love you so much,” she said as she lowered her arms and took a half step backward. She wiped away tears from her eyes.
I said, “I love you too, Addison. What brought this on?” She then went on to tell me about the trade. As she took a seat beside my desk and went through all the details of the trade, her voice filled with excitement. The initial idea, then the research, the analysis, the execution. She had felt very confident in the trade so she had taken a larger position than any she had done prior, and it paid off. It was a huge success. I could see the pride she felt, and it made me proud as well. My little sister was on her way. I suggested that she print out something from the trade and have it framed for her office. She could always look at it and remember her break through trade. Sitting together with her there in my office that afternoon, we were talking not just as brother and sister, but as colleagues. As a team.
From that day forward it seemed like our relationship changed. It seemed like her newfound confidence in herself made her even more impressive as a woman than ever. She was already beautiful, smart, funny and had a great personality, but now she was successful and accomplished. She was more alive than ever. She was bold, and strong. She was a very impressive woman, and I loved the affection she obviously had for me. She wasn’t holding back, and the love she showed for me reciprocated right back at her. Being with her every day was amazing.
One Saturday in early August we went to Leominster State Forest to tackle their most challenging mountain bike single tracks. We’re not elite mountain bike riders but we are certainly in the expert category. It was a great day. We rode for almost four hours before we decided to stop for the day. We went back to the parking lot and loaded the bikes onto the rack on my Porsche Macan.
We were both standing together by the bikes when I noticed that another bike rider was walking up to us along the side of my car. If he had continued he would have been in very close proximity to us, and it looked like that is what he meant to do. I may have reacted a little harshly but I couldn’t help it. I yelled at him, “Hey, Dude. Back off. Don’t come any closer, okay?”
“Geez, man. Don’t be a dick,” he yelled right back at me. By then he was now about six feet from Addison, who moved away from him, going behind me and around to the other side of the car.
Maybe I was overreacting but now I was pissed. “Do you really think it is okay to just walk up in the faces of people these days? What the hell is wrong with you?” I looked over at Addison and could see the fear in her eyes.
“I’m not sick, asshole.”
“Yeah, well you don’t really know that for sure, do you?” I almost returned the ‘asshole’ right back at him but held it inside. “Will you just back up? Please.”
“Yeah, yeah. I’m going. You and your girlfriend can have the whole fucking forest to yourselves. Asshole.” He turned and walked away in the direction from where he had come.
I turned back to Addison and she moved into my arms. “Oh, my god,” she said. “He came out of nowhere. Can you believe that? He doesn’t seem to have a clue. He just tried to walk right up to us without even wearing a mask. I guess we need to be more careful.”
I held her tightly to my chest. “We’ll be okay. He didn’t get too close.”
“I hope so,” she said. “Please take me home. I’m really getting hungry.”
It was a strange, scary time in the world that year. No one knew for sure how bad the pandemic was going to be, but it was already hitting very close to home for us. Of the two lawyers from Addison’s old firm who had tested positive, one of them had died, and the other had survived after being hospitalized for three weeks, but his wife had also died. One of my old classmates had died. “Maybe we should just stop going out entirely until they have a vaccine,” I said as I drove home.
“Absolutely. We have all we need at home.” She reached across the console and took my hand.
It struck me that she had just called my place “home.” I felt the same way. It no longer seemed like my home. It seemed like ours. “Let’s get showered and have a lunch, then spend the afternoon by the pool.” My covered patio has a TV that I loved using for sports events. I used to have parties for friends there to watch the Red Sox and Patriots games, but those days seemed ages ago now.
Addison put together chicken salad sandwiches for our lunch and hauled everything out to the patio table on a tray. I was eager to try out a new craft beer that I’d ordered that week. All was good in the world again. We were safe and happy in our own secluded paradise.
When we finished eating I took all the lunch dishes and trash back into the kitchen and stacked the dishwasher. When I returned to the pool I saw that Addison had taken off the sun dress she’d worn while eating lunch and had reclined in the sun wearing an incredible bikini. She was applying sunblock to her legs. I sat down in the shaded patio and started to read a book.
Addison called out, “Hey babe, will you come put some of this on my back?”
“Yeah, sure,” I said as I walked toward her. Did she just call me ‘babe?’
“Just the middle of my back where it’s hard to reach. I already got it everywhere else.” I spread the lotion on her already bronzed skin. Her skin was so soft. I thought to myself, again, that I had gone much too long without the touch of a woman’s skin. It only took a few seconds to apply the lotion.
Casually, I asked, “New suit?”
“Yes, you like it?”
“What’s not to like? Beautiful woman in a small bikini. I guess there might be better things in this world but right now I can’t think of what they might be.”
“Hmmm ... then it seems to be having the effect I’d hoped. Glad you like it.”
I moved back to my shaded chair and my book “Let me know when you need to reapply.”
About an hour later she rose and jumped into the pool. “Come on, babe, join me,” she called out when she rose to the surface. She said ‘babe’ again! What was up with that?
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