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Bored Brother And Sister Dilemma

Bored Brother And Sister Dilemma

by xyster
20 min read
4.63 (49200 views)
adultfiction
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"I am bored!" exclaimed Jessica, as she plopped herself down next to me on the bed. I had to move to the left to keep her from bumping into me. Her weight, and the force with which she hit the bed, caused sort of a wave in the mattress, and made my body to jump up a little.

"And...! What am I supposed to do about it?" I replied without looking away from the screen of my phone. I was busy scrolling through my social media stream, which was my way of dealing with my own boredom. I was feeling bored too. I had my clothes and shoes on, trying to decide what to do next. I was planning to just go out and be somewhere else, instead of being at home.

"Nothing. I am just saying, that's all." She seemed half there and half somewhere else.

She had plunked herself next to me in a backward sort of way. I was lying sideways on the bed, with my feet dangling on the left side and my head resting on the right side. She jumped from the right side, face down, with her head facing left, and her feet to the right. She used her elbows to support herself on the bed and to keep her weight off her boobs. Once she was settled in that position, she casually lifted her feet off the bed with her legs bent at the knees and started to sway them slowly in the air.

She was wearing her Crocks, that she had decorated with various tiny, plastic thingamajigs. As I looked up towards the ceiling, I saw the top of her shoes pointing downward in my view. It was weird to see them dangling upside down. She had no socks on, so I could see her toes with bright orange nail polish gleaming down in my direction.

"Why don't you find something to read, or watch something on TV?"

"Na! Done all that. Nothing seems to be helping."

I took my eyes off the phone and turned to look at her. I was startled to find my face right next to her thighs, looking down on her legs and right onto her butt. At first, I had this strong urge to sit up because I felt kind of strange about being so close to her ass. Then I decided to just let it be. After all, I didn't get so close to her on purpose. It just happened, kind of accidentally. It was she who had positioned herself that way next to me. Besides, I was feeling kind of lazy and getting up seemed too much of a trouble.

"Doesn't your college give you any homework to do, or something, to keep you busy?"

"Nothing is due, or urgent. I don't feel like doing any of it."

She settled herself on the bed even further by extending her arms forward and putting her chest flat on the bed. I guess keeping her weight off her boobs was no longer the issue.

She didn't seem to be aware of the intimate pose that we were in. I was so close to her thighs that I could clearly see the small, delicate hair on her legs. They were barely visible, but I could still see them.

To make matters worse, she was wearing these white, high-rise shorts that fit very snuggly around her curves. My sister has a nice, full ass, and I was looking right at it so up close. It seemed a little unsettling to have such a vivid view of it, but at the same time, there was a certain appeal to seeing it in such a carefree way. She did not know that I was looking at her ass and I didn't have to look away quickly, as I normally do when she passes in front of me on occasion.

In addition, as her feet continued to sway, her thighs would open slightly and then close gently with each move, teasing me to look right at the juncture where her thighs met and where her special parts lay hidden behind her shorts. To be honest, it was an intriguing display, a very titillating site. Sometimes things just work out in such a way that an ordinary thing becomes quite interesting.

Suddenly I felt a rush as I realized that I was looking in the general area where her pussy was. I almost lost my breath when that thought hit me. I have never had the occasion before to be looking at that view, and from that angle, and now that I was right there, the whole thing was--let's just say--confusing. On the one hand, I was looking at my sister's private area so very close, which is something I am not supposed to be doing, or even have the chance to do it; on the other hand, she put herself in front of me in such a way that I had no choice but to look at her private area so uninhibitedly. I shouldn't have been looking at her so closely, but that view was so stimulating that I couldn't resist the urge to keep watching. Since she wasn't even aware of what was happening, I was in no hurry to stop looking.

I finally had to stop, though, once the guilt of ogling her surpassed the intrigue of seeing her special area. I sat up quickly just to shake those thoughts from my head. She turned towards me with a start and asked, "What happened?"

"Nothing," I replied as I looked at her. Her hair seemed a bit ruffled; I am sure due to her jumping on the bed. I reached over and pulled them together.

"Thanks," she said, somewhat lazily.

"Hey, I know how to get you over your boredom."

"Really! How?!" She also got up and sat on the bed. I don't know how to explain it, but that sight of her sitting on her knees, her hands folded in her lap, and her eyes fixed on my face, was very attractive. She looked very sexy.

"There's a new chicken place that recently opened. Let's go check it out."

She seemed very excited at the suggestion and jumped off the bed, quite effortlessly. I grabbed my keys from my dresser and moved towards the door. Just before I passed her on the way out, something came to my mind. I stopped in front of her and said, "Let me first look at you, see how you are dressed. I don't know if I want to be seen with you the way you are dressed."

"Hey!" She protested. "There is nothing wrong with the way I am dressed. I always wear shorts and a T-shirt."

I gave her a full look and then said, "Okay, but you have to lose the Crocks."

"What should I wear then?"

"I would prefer some high heels," I said casually, but in reality, I was just pushing to see how far I could play it. Needless to say, I was feeling a bit mushy, and I was having fun with her.

"High heels?!" She seemed a bit confused. "Why the high heels? I don't even own any high-heeled shoes."

"Too bad, then." I started to walk out. "I guess you can't go then."

"Wait!" She started thinking quickly. "I think mom has some. Let me go and steal her shoes. I'll be right back."

She ran quickly to our mom's room. Mom was probably downstairs somewhere. I went out of the house and walked to my car. She came running out a little while later. She had these white, high heels on and was trying to keep her balance as she hurried to the car.

When we made it to the chicken place, it was packed. There were cars lined up in the drive-thru, stretching back quite some distance. People were standing in lines at the counter, and those lines came all the way out to the parking lot. We must have waited almost forty-five minutes before it was our turn to order. Luckily, we were able to get a small table as soon as the couple sitting there was done and we jumped on it. I couldn't believe the place was so busy, even though the food didn't quite live up to the hype.

Jessica received a lot of attention, as I had assumed she would. After we finished our meal, we sat there for a while just chilling. That's when she asked me, "So, why did you want me to wear high heels."

I was in a very pleasant mood, so I answered her just the way I felt. "You look so hot in your outfit. I knew that high heels would make you look even hotter."

She didn't expect such a forthright answer and was somewhat taken aback at my compliment. It took her a while to ask, "You think I look hot?!"

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"I am not the only one. Look at all the people gawking at you. It is not just the men who are staring at you, even many of the women are also checking you out."

"I did notice people looking at me, but I didn't think it was because I look hot. I thought it may be because I am underdressed."

I remembered the scene from earlier in my bed and replied. "You are not underdressed. Just look around and you'll see some other girls dressed in a similar way. But they don't look nearly as hot as you do."

She was quiet after that. I could see that her cheeks had turned a little red after my comments, and I could sense a smile on her lips. Even though it was not quite an elaborate one, her lips did seem a bit stretched into a smile.

About a week later, on a rather slow day, I was feeling bored again. I wanted to go somewhere but couldn't decide where. I was in my room just pacing when Jessica peeked in through the door. When she saw me, all dressed up, she asked, "Are you going somewhere?"

"I am going, but don't know where. Just trying to decide where to go." As soon as I finished saying that, a thought popped into my head. "Hey, do you want to go check out that chicken place again?" I was up for another adventure.

"Okay. I am not doing anything," she said and then she came inside my room. "How do you want me to dress this time?"

She asked me so casually that it took me a short while to realize the impact of her question. She was willing to dress according to my preference. That opened the door for a lot of possibilities. I had to think for a while before I could tell her how I wanted her to dress.

"You wore these ripped jeans the other day with a white crop top. Most of your belly was showing, and the ripped jeans were showing most of your left leg. That was an amazing look. Try that today."

"Really. You liked that look."

"Oh, it was incredible. You looked really good."

"Ok, I'll go change. I also bought my own high heels. Do you want me to wear those as well?"

I thought for a moment, then replied, "No. Let's save the high heels for another day. Today, wear your white sneakers. They go well with that outfit."

"Looks like someone's been noticing my style."

I smiled. "Sorry, I have no choice but to notice it. You always stand out and look very hot and sexy."

"Huh, first hot and now sexy. I guess we are making progress."

With that, she left the room to go and change. I sat on my bed and waited for her. She came back after a while. She was dressed just the way I had imagined her, and she did look very hot and sexy. There was something very attractive about her legs showing through the jeans. Most of her belly was visible. Her shoulders and arms were bare as the crop top only covered her boobs, and a little bit of the area above and below them.

She stood at a little distance from me, held her hands on her sides, and made a complete turn in front of me. She asked, "So, how do I look?!"

"Perfect! Just really, really nice." I said with a smile. "Okay, let's go."

The place was not as busy as it was the first time we came there. I guess the novelty of the grand opening had worn off. Still, there were enough people around to stare at Jessica and make her the centre of their attention. I could tell that she was enjoying every bit of it.

We sat there for a while, as there was no crowd pushing us for the chairs. We talked about a lot of things. When there was a decent pause, she turned to me with all of her attention and asked, "So, what do you have in mind for the high heels."

I was at a loss, as I had forgotten my earlier comment. There were other things occupying my mind, like my uncontrollable urge to run my hand on her thigh as we sat there, especially the part that was showing through her jeans. For some reason, I wished that she had sat next to me, instead of sitting across from me, but her being my sister and all, that didn't seem like a reasonable expectation.

She noticed that I didn't know what she was asking, so she asked again, "Earlier you told me not to wear the high heels. You said let's save the high heels for another day. What do you have in mind for the high heels?"

I understood her question. I had to think for a while for the right answer. She waited.

I finally had something. "We can go to the movies and then to a nice restaurant for dinner. You can wear a short black dress, maybe with some nylons, and your high heels of course."

"Ooh, someone is trying to make me live out one of his fantasies, huh?"

I felt a little embarrassed. She noticed that I was turning a little red.

"Don't worry. I am game. But it has to be one or the other, not both."

"What do you mean?" I was a little confused by her remark.

"Either we go to the movies, or to a restaurant. I don't want to rush and try to do both. So, it has to be one or the other."

"Okay then, I'll let you decide. You pick where you want to go and I'll either buy the tickets or make a reservation."

"Huh, let me think." She sat there for a while, going back and forth in her mind about which plan she should go with. Finally, she told me about her choice, "If I am going to dress like that, I want to go to a nice restaurant. When I go to the movies, I want to dress casual."

"Okay, restaurant it is then. I'll make a reservation for next week."

"In the meantime, you can take me to the movies, and I can show you my casual look." She had this wide smile on her face, and she looked so adorable, I wanted to kiss her. She looked very beautiful when she was being so playful.

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"Okay, we can go to the movies tomorrow."

Her casual look was grey sweatpants with a white top, and a matching long sleeved hoodie. This was not a full-length hoodie. It came down to the middle of her stomach, at about the same level as her top was, and looked really sexy on her, especially when she covered her head and let her curled long hair extend over her breasts. She looked incredible, and I told her over and over as to how unbelievably attractive she looked. She kept blushing every time I complimented her.

We were standing in a line to buy popcorn, candy, and soda. I was eyeing the Nachos when I turned to face her and asked her if she also wanted Nachos. Her hoodie was not on her head, and she had moved her hair to her back. That's when I noticed it. I am not used to seeing her that way, and my reaction can be forgiven for being spontaneous and even impulsive. I grabbed the front of her hoodie, pulled the sides apart, looked straight at her breasts, and whispered, "You are not wearing a bra."

She grabbed the hoodie away from my hands and zipped it up, all the way to her neck, and said, "Stop it. I did wear one, but it seemed too noticeable with this top. So, I decided to be extra casual."

I was speechless. I didn't know what to say, other than, "Sorry, it was a surprise. I couldn't control my reaction."

"That's okay," she replied. "I can forgive your reaction. And thanks. And yes, I also want Nachos."

I asked, "Thanks for what, I don't get it."

"For the reaction, and for the look on your face. It was priceless," she said with this huge smile on her face. "Now let's get the Nachos. The movie is about to start. I am also in the mood for some popcorn. Ask for a lot of butter on them. Also, get the large drink. We can share it."

Once we were settled in our seats, she did something that I found quite touching. She took my Nachos, mixed the cheese and chips, decorated them with JalapeΓ±os, and gave them to me to eat. Then she unwrapped two straws, put them in our drink, and put the drink in the cup holder that was between our two seats. After that she prepared her own stuff, and we started to eat and watch the previews. The previews took a long time, and by the time the movie started, we had already finished our Nachos. She put her feet up on the seat in front of us and we started to watch the movie. We shared the popcorn and the drink as the movie progressed.

I had trouble focusing on the screen. I kept thinking of her being braless and looking so sexy and sitting so close to me. Sometime later, I lifted the arm of the seat that was between us, and she scooted over a little closer. I turned in my seat a little more towards her, and whispered, "You know, the theatre is pretty dark now, so..."

She was watching the movie, so she didn't quite comprehend what I was saying. She asked, "What do you mean?"

"What I mean is that the theatre is pretty dark now. No one can see you."

"So..."

"So, you can unzip your hoodie now. There's no need to hide your stuff."

She slapped me with the back of her hand. Her slap landed on my shoulder. It wasn't a hard slap, just a little more than a touch. "Stop it," she whispered.

I went back to watching the movie, but I kept looking at her every now and then. I think she knew that I was looking at her. A while later, I noticed that she reached for her zipper and opened her hoodie. I also noticed that she went a little extra and opened her hoodie wide, so it was no longer covering any part of her front.

When we came back to my car after the movie, I went to open the door for her. As she was about to enter the car, I told her that I wanted to share something with her. She leaned back into the car and looked at me. Her arms were on her sides and her feet were pushed outward a little. Her hoodie was casually covering her front; she must have wrapped it around her as we left the movie theatre.

I reached for her hoodie and held the sides with my hands. She watched with keen interest as I opened them outward and exposed her breasts to my view.

I said, "I didn't get a proper look when I first saw you, so I want to get a good look."

She answered, "Is that what you wanted to share with me? Because that is not sharing."

I saw her breasts hanging very provocatively inside her top. Her nipples were poking through the material. She carried that look very well. After taking a long and deep look, I said, "You know that you look very sexy. We have established that part already. The way you are looking today, it is totally amazing."

She didn't say anything. She just listened. Her eyes were focused on my face, reading my expressions. I continued, "But do you want to know what is the sexiest part of your look?"

"What?!" She asked with a lot of interest.

I reached up to the front of her sweatpants where her drawstring was visible and hanging. The drawstring was tied in the front. I grabbed one end of it and gently pulled it out towards me. She just looked at my hand and let me pull it out completely.

I said, "This drawstring is the sexiest part of your look, because it holds a lot of promise behind it."

"Oh, stop." She said with mock indignation. I could tell that she really did not know how to react to my comment, or rather to my insinuation. She got into the car with her drawstring still untied. She didn't bother to tie it back up. The elastic around her waist was enough to keep her pants up.

When we got inside the car, she moved the seat all the way back, leaned it back as far as it would go, and put her feet, with her sneakers, on the dashboard. I started the car and before putting it into reverse gear, I looked at her to take in that view.

She smiled and said, "What? Taking another proper look, are you?"

I laughed, and replied, "Yes, now let me see your bellybutton. That would enhance the look a thousand-fold."

She reached down and slowly slid the top of her sweatpants down until her bellybutton was in full view. She said, "I can't believe that I am actually doing it."

"Sorry, just trying to make the most of this opportunity," I said with a laugh. "Now we can start moving."

She rubbed her hand over her belly and said, also with a laugh, "Okay, but you better be driving to a coffee shop. I am in the mood for some Starbucks."

"Yes, ma'am." I gave a fake salute and started moving. I noticed that she pulled the ends of her loose drawstring downward and let them hang right between her thighs. Whether it was just an innocent move or there was something more to it, I had no way of knowing.

She selected Friday evening as our restaurant date. I made the reservations with a nice restaurant, which was about forty minutes away from our house. The week went by quickly as she had her college to contend with and I had a couple of projects that kept me busy at my job.

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