Homework Incentive

My sister and I lived at home with our parents. I started community college that year, and my sister the year before, being a year older than me. I was now 19, and my sister Amy was 20. My sister and I were quite different. Amy was the smart one, the athletic one and the popular one, as well as very beautiful, at least in my opinion. While being athletic and poplar, she was also a bit of a hippie.

Mom had been into fashion and nice clothes and always had just the right make-up. Mom had been into everything looking perfect, owning the right things, having everything at home look nice. Whereas Amy never wore make up. Instead she wore either jeans and t-shirts or often those flowery dresses, skirts, and peasant blouses that you picture hippie girls in. Mom and her had often grated on each other some. I always wondered if her hippie thing was a rejection of my mom and her materialistic values.

I guess I always looked up to Amy. As kids we fought a lot, teasing each other, but once we hit our teens, we kind of just had our own orbits.

I was kind of geeky, just not the smart kind of geeky. I made it through high school with mostly Cs. Amy on the other hand, got all As, always. While she spent her non-school hours and weekends in school clubs, sports and seeing friends, I was usually home watching stuff or playing video games with online buddies.

About 8 years ago, our mom got colon cancer, and after a year, died of it. It was, of course a very hard period for us. My sister sort of stepped up to being the responsible one in the house, and after that I think in my dad's eyes she could do no wrong.

On the other hand, dad ragged on me even more about not doing well, and we sometimes fought. I think he felt now the total weight of responsibility for me on his shoulders. I often just retreated into my room and my video games.

Of course, at that age, I also thought about girls a lot, but think about it was about as far as I got. It is not that I am bad looking. I am about average height and build. I do not work out, so I am not muscular. But I am not fat or odd looking either. Of course, there were girls in my classes, but I did not have the nerve to approach them, and could not see why any would be interested in me, not any that I was interested in anyway.

But things were soon to change in an unexpected way.

As I think I mentioned, Amy had gotten through high school with all A's, while I just squeaked through the year after.

Now in the local college but still both living at home, it was the routine that after dinner Amy and I would sit at the dining room table and do our school work, usually for an hour or so. Dad would wander off to do whatever.

This was a usual day and I was working on an algebra class. It was now about mid-semester, and I was falling further behind. I guess I was making grunting noises in frustration as I worked. Amy was sitting across from me, as usual, reading and her English assignment.

Amy always dressed really nice in her flowing skirts and blouses, and just looked good. She wore her wavy sandy blond air on the long side. She was about five-foot-seven, and athletic without looking muscly, and nice curves and full breasts. I guess as a young man, I could not help but always notice her breasts. And at home she never wore her bra. I do not know if she knew the effect it had on me, and I wonder what dad thought. I guess he figured since Amy was so perfect, it was okay if she dressed like that.

That evening she was in a white skirt and a loose white sleeveless peasant blouse. I did not want to glance at her as I could make out her boobs swaying under it if she moved, which seemed to happen a lot.

"What is all the grunting over there?" Amy called over to me

"Oh, sorry, this algebra stuff, just confuses me!"

"You need a tutor or something."

"I'm just stupid," I whined.

Amy sighed, "No, you are not stupid, I think you need some help, though," and with another sigh, "Come over here, sit next to me, and I will help you."

She sounded a bit grudging about it, but after some back and forth of her assuring me she meant it, I did. She opened my book and started to study the pages, the problems, then started to ask me questions about what I knew. She was slowly leading me through it, helping me see it. Then I was noticing as we leaned over the text book and my notebook, that I could see right down her blouse, to her firm breasts and fully even see her nipples. I lost track of what she was saying, mesmerized by what I was seeing.

It took her a bit to realize it then, "Enjoying the view?"

I turned red, so embarrassed to have been caught. It was not like I had not thought of what they looked like, but I never had the nerve to actually try to spy or peek. I guess really, I respected her too much, or maybe I was too chicken and afraid of how she would react if I got caught.

"I-m sorry, I--I'm sorry, blushing.

She then smiled instead, "Hey, yeah, not your fault really, I guess they were on display..." as she sat up.

"You like seeing them?"

I just shrugged.

After a little pause, she said to me, as if having decided something, "If you work seriously with me on this, and get to where you understand it and can do it on your own, I will let you see me topless."

"You are joking, right?"

"No, totally serious--you want to see them, right? And I figure it'll give you some incentive, and I'm tired of sitting here listening to you mope and whine about your school work."

I did want to. I really did want to see her breasts, so I focused, and she really helped me. It took quite a while, but I finally did it. Our dad even came by and noticed us, and I think was surprised to see us working together, and working much longer than usual.

Once we were done, Amy stated, "Okay that is good for today. Go put your books away and meet me in my room."

When I arrived, she was standing by her bed. As soon as I entered and closed the door, she pulled her shirt over her head. There I was staring at my topless sister. I was a little frozen, but then I relaxed a little, but did keep staring.

"Want to sit down and hang out?" she asked me.

I saw her sit and pat a spot on the bed next to herself.

"Um, yeah, sure."

I felt a bit awkward sitting there with her topless, in just the white pleated skirt, but she made it seem natural.

She started talking to me about her day, and what was going on with her, for a few minutes, then asking me. I didn't really know what to say, but she was pretty good at drawing me out, getting me to open up a little.

The next day, right at the beginning of our doing our school work, she invited me to sit by her and work together.

"Same deal," she told me, "If I see you are working hard, and making progress, and you let me help you, you can hang out with me again--with my top off."

We would work side-by-side, and when she saw me having problems she gave me a little tutoring session. This meant that it actually took us longer to get our work done, but I was getting stuff right for a change. She would even sometimes tell me about what she was learning. I am pretty sure she even purposely let me see down her loose top at times.

I started to notice that at home she did not worry about if someone could see down her top. I could see that dad seemed to walk by her sometimes if she was reading hunched over, or at the dinner table. If she noticed or cared, she showed no sign of it.

For the rest of that week, it continued. I was not suddenly a top student, but I was slowly catching on. I was also enjoying not just getting to see my sister's breasts, but to hanging out with her. It was like I realized how lonely I had been. With my "friends" we only talked about our games and what we were doing, or like made up dreams of a future that would not be, and the girls we would have. But with Amy, we talked about real things, feeling and she shared with me about herself, what was going on with her, in a real way.

But I did like seeing her topless, and at the end of the week I worked up the nerve to ask if I could touch them. At first, she did not say anything, but she did not get angry either, "Let me think about it," she ended up replying.

She did not say anything more about it until the following Monday, "Okay, tell you what, your reward this week will be that you can also touch my breasts."

I was ecstatic! I almost had a harder time focusing thinking about that I was actually going to get to touch them. But I did manage to keep my emotions in check enough to get my work done.

Finally, again, we did get it done, and I raced off to drop my books in my room to get to her room. She was already topless, as she had been doing. We sat down together again on the side of her bed. I asked if I really could touch them, her breasts.

"Of course. That was the deal. Go ahead," she smiled at me.

She sort-of turned toward me as we sat there and I reached out my hands to cup them on her soft breasts. They felt as wonderful as they looked, the flesh soft to the touch, giving and yet firm in their own way. I held and then sort of massaged them for what seemed like and eternity. She just let me with a sort of smile on her face.

"Why don't you try it with my back against you?" she suggested.

We shifted positions so I could be behind her, and again sideways on her bed, I had one leg up and bent and one over the side, so she could lean back against me. I then reached around her to cup them this way. It was much more comfortable, and also nice to have her whole body leaned into me like that, and to just hold her.

For a while we just were quiet like that as I felt and kneaded her breasts. However, after a little bit, without moving away to asking me to stop, she just started talking to me like we would, asking about my day, and telling me about hers, all the while letting me continue to hold her and play with her breasts.

"From now on, getting to feel my breasts is part of you reward as long as you keep up with your work," she added before I had to finally leave to head to bed.

At night I was masturbating thinking about my sister and her body, and what I got to see, and now feel. Not only that but we were getting closer as friends. So, I could imagine her even, well, in a different way. She really was treating me not just as if she liked me because I was her brother, but that she actually did like me. I knew that if I was not her brother I was not the sort she normally hung out with. Her friends were all like smart, outgoing, like good at stuff.

The next morning, I saw her at the kitchen counter, dressed ready for school. This idea came into my head to see if she'd let me touch her breasts there. I walked over quietly and reached around and hugged her from behind, but holding her breasts in my hands as I did. She jumped sort of startled.

"Hey, what are you doing?" But she did not actually pull away,

"You said I could touch your boobs now" I said with a sort of smirk in my voice.

"Well, okay, just don't let dad see you do that."

My next surprise came when as we headed off to school together, she suggested I join her for lunch in the school cafeteria. Normally once we got to campus, we just went our own ways and did not see each other until we headed home. We did go and leave together as she had a car and I did not, so if our schedules did not coincide the other would hang out and find stuff to do around campus until the other was ready.

"Meet you at 12:30 in the cafeteria."

When I got there, I expected she meant just her and I, but she waved me over to where she was sitting with a bunch of her friends. I sat down and she introduced me, though I noticed she did not actually say I was her brother. We ate and they chatted--they did not exclude me at all, though I really did not have much to say and was a little shy. From then on, I joined her and her friends for lunch and started to feel more comfortable around them.

A couple of days later she asked me if I would like to hit with her at tennis. She said her practice partner was out that day. I could play tennis a little, but was not in great shape, and never played seriously. Amy was in perfect shape--in more ways than one, and was a really good player. She did not wear those fancy tennis outfits, but just loose shorts and a regular t shirt. Her breasts would bounce around pretty freely.

Again, I was not sure why she asked me. I guess just to be nice, or maybe she just did not have any one else to hit with last minute and wanted the practice and exercise. I was good enough to mostly keep a rally going with her. Though we could not really play points. I am not sure how much help to her game I could really be.

But then she started hitting with me regularly, finding an extra time to play. I had not been doing regular exercise for a long time, so the first few times I was a bit sore after and especially the next day, but I started to get my wind, and got more rhythm in my stokes. I was not going to be anywhere near as good as she was, but I could at least be not embarrassing at it.

My sister was including me in more and more of her life, and I was liking it. What I was finding though, is that what I liked most was just being with her. It was really nice to be included with her friends and to be treated like I fit in. It was good that I was getting out and doing stuff. I felt good about that I was doing better in my classes. I was speaking up more in classes and I could tell that at least some of the professors were noticing.

Yet, more than anything, I loved hanging out with my sister, getting to feel close to her. In part, it was that she was beautiful, smart, and popular. She treated me so well, she acted like she cared about me and what I thought and how I felt and how I did. I will not leave out the fact that her letting me hang out with her topless, and let me caress her breasts was one of my favorite parts of being with her. But it was now like having a best friend, someone I trusted and could confide in and who confided in me.

As I said, it was our routine now after dinner and our studying, to go to her room to hang out. We would just talk, and often we sat on her bed, back against the wall, and her leaning her back against my chest, between my legs, and I would cup and play with her breasts as we talked.

She never acted sexual about it, did not offer or ask to touch me, and I did not try to do anything more.

On the other hand, at school, she often put her arm around me and let me do the same with her. Sometimes she gave me a peck on the cheek in front of her friends. We never let on that we were siblings and they probably saw that we came and left together. They must have assumed were boyfriend and girlfriend, and she seemed to want them to think that. I really wanted to ask her about that, but every time I was about to, I chickened out.

We were only a few weeks to the end of the semester when she told we she was going to give me a new incentive.

"This is not like a tomorrow thing, but for the end of the semester goal. If you get at least a B in all your courses I will be yours for a weekend. You can choose what we do, maybe go somewhere?"

"Like whatever I want?"

"Yes, anything, well that I can afford."

That really got my imagination going, and my motivations well. I put even more effort into studying. I found I was rarely playing my computer games anymore, and I did not have many other hobbies or activities to keep me occupied, so I had the time to study. I was doing a few things with my sister and her friends, like playing tennis with her now on a regular basis, and even playing other times, or just hanging out on campus with her and her friends.

She was also going out less in the evening, as we were spending those pretty much together. She still hung out with her friends on campus and played tennis and had yoga classes. Evan on weekends she would spend some time working with me and hanging out, and taking me out to play tennis as well.

I was now on a mission to make sure I got the best grades. I was spending more on more of my free time studying as we got closer to the end of the semester, and at this point I had with her help learned to study much more effectively.

Then, the day finally came and our grades came out.

I had three As and two Bs, which was by far the best grades I remember ever having. My dad was more than surprised. He knew my grades were improving and that I had been working much harder, but he still did not expect that much improvement.

Amy told dad that she had promised me that we would do something together if I got strong grades and we were thinking maybe of going somewhere for a few days.

"Just the two of you?" Dad asked.

"Yes, he worked really hard, and I think a little vacation would be nice for us both."

Dad was impressed with Amy for doing that, thinking of that, and offered to pay for up to a thousand dollars of our get-away.

"Wow, thanks dad, wow!" I exclaimed.

It was a few hours drive to our destination, and I was just excited to be doing this. Not just getting away, but getting this time with just my sister and I. While we had been spending more and more time together, I was still really surprised that she would want to get away for several days with just me.

"Do you think you could go topless in the car?" I asked Amy.

Without even really much of a pause, she asks me to take the wheel as she drives, and she pulled her blouse over her head and tossed it in back.

"You like being topless?"

"Yeah, kinda"

I did not mention it again, but we chatted along the drive, talked a little about what we might do.

Amy had found a nice hotel for us to stay at. The place had a series of two story building around a grassy area, large pool and communal jacuzzi. It was only a short walk to the beach.

When we go to the front desk the receptionist asked if we wanted a single or double. I quickly said a single, my heart racing as I was unsure how Amy would react. But all she die was say "Yes, a single, please," which really surprised me.

She gave us a map to the room.

When we got to the room, it was a basic hotel room, with one king bed that filled up most of the room, a very small table, a dresser, a small closet, TV, bedsteads on each side of the bed and a basic bathroom with a tub/shower. The back sliding-door led out to a very small patio, and then to a grassy area that led to the pool and jacuzzi surrounded by five similar building.

"So, you wanted to share a bed?" Amy said to me, and I could not tell if she was annoyed or not.

"Um, yeah, I hope that is okay."

"Just teasing you, of course, it is okay. I said you would get what you wanted this weekend."

"Amy, why are you doing this?

"What do you mean?"

"I mean, well I love it, I love everything you have done for me and are doing for me, but I don't really get why you are?"

"I wanted you to do better, and I really do like hanging out with you."

"No, but really like you first help me with my homework then let me see your tits, have been spending more and more time with me, then, instead of doing something with your friends you go off with just me, and like when I say one bed, you say it is okay--I mean, up until now I was liking it so much I did not think about, like well, it seems too good to be true. YOu even seem to want your friends to think we are a couple."

"I know it kind of crept up on me too--it just started out with my being tired of seeing you all down, and, well, it felt good to see I could help you out. Then I guess, with us hanging out and sharing, and getting to know you like more the real you, I just well, I guess we just got to be closer, you know? I also found out I like being with you more than anyone else."

"And you let me play with your breasts."

"Yes, I did." She laughed.