Jack & Jill Ch. 01

Ok, we’ve heard them all before. Our whole lives, my younger sister, Jill, and I have endured all the jokes and teases from practically everyone because of our names. Of course, grammar school was the worse. Hardly a day went by when at least one person didn’t ask, “Are you going up the hill?” or “Hey, where’s your pail of water?” or some other comment relating to the nursery rhyme. Things eased off once we got in high school though. Not too many of the other students wanted to tease a 6’3”, 230 pound starting defensive lineman for the football team, nor his sister. If one good thing came from all the teasing, it was that Jill and I became very close. I was always around to take up for her and to chase the bullies away. I was her “defender”, and my poor sister needed one.

Making the football team gave me a certain level of popularity at school, but Jill was more of the unpopular, “plain Jane”, wallflower type. Most of the other kids classified her as a “nerd”. She wore glasses, was very studious, quiet and shy. She always had her hair in a ponytail and wore baggy clothes. She had one girlfriend in school, Lisa, and I don’t think she ever had a date. When I graduated high school and went off to college on an athletic scholarship, Jill still had two years left before her graduation. I remember her calling me one night at my dorm room and she was all upset and crying because no one had asked her to her own senior prom.

But finally, the day came when Jill got out of that hellhole known as high school. Her years of hard work and studying had paid off for her and she had become a very sought-after college academic prospect. She had scholarship offers coming out her butt. Jill could’ve gone anywhere, to any university she pleased; Vassar, Harvard, Stanford, Notre Dame, they all wanted her. The summer after her graduation, Jill had some big decisions to make.

During the two years that I had been away from my sister, I often found myself lying awake at night in my room just thinking about her. I couldn’t believe how much I had missed her. It actually started the day I left, but I figured it would get easier as the time went by, but much to my surprise, it hadn’t. We had always had each other, had always been together from the time she was born. When I left for college, it felt like I had left my right arm at home. So, naturally, I tried to convince Jill into going to school with me. She told me she would think about it, but eventually she told me that it was time for her to stand on her own two feet. Eventually, Jill made her choice and that August, our parents had two children going off to separate universities.

Jill and I made the most of our laptops and our respective university’s free internet connections by keeping in constant touch via email and instant messenger, and we talked on the telephone once a week. Jill’s first semester was quite an adjusting period for her. Of course, she kept a perfect 4.0 grade point average, but through her letters and conversations I got the impression that she was having a bit of a difficult time with the other aspects of college life. We had a long talk when we returned home over the Christmas break, but I still felt a little uneasy about Jill’s future at school.

As it turned out, I ended up worrying for nothing. Shortly after the semester began, I received an email from Jill. It sounded as though she were very excited. She had met a girl in one of her classes and the two of them had really hit it off. When we talked on the phone that week, all Jill could talk about was her new friend. It was Connie this and Connie that. I was very happy Jill had a new friend, though I would not realize Connie’s influence on my sister until the following summer break.

I arrived home the day before Jill. Our parents picked me up at the airport and drove me home. I was looking forward to an afternoon of lounging around the pool with a couple of brews, but my parents had other ideas. Dad wanted to talk football and Mom wanted to talk “special girls”, as in whether or not I had met any. The afternoon was pretty well shot by the time we were done, and after one of Mom’s delicious home-cooked dinners, Dad and I sat out on the back porch for a while before deciding to watch a movie on television. During the movie, I heard the phone ring and Mom answering it. It was Jill, calling to confirm her flight info with us. I heard Mom telling her that I had arrived earlier today and I was fine. Then I heard her say that she didn’t think I’d mind at all. When she hung up, Mom came into the living room.

“Well, that was Jill. Her flight is due to arrive at eleven-thirty tomorrow morning. Jack, you wouldn’t mind picking her up, would you? She asked if you could,” Mom asked.

“Sure, Mom,” I told her. “Be happy to. Did she say why me?”

“No, but I’d imagine she probably wants to spend some time with her big brother before her father and I grill her about school,” Mom laughed.

“She probably knows you two will be leaving for vacation in a week and you’ll monopolize all her time,” I kidded with her.

“We are sorry about that,” Mom apologized. “But these are the only weeks your father could get off work all in a row.”

“Hey, Mom, that’s all right,” I told her. “It’s been a long time since you and Dad have had a real vacation. Jill and I totally understand. You two should go and don’t worry about us. Besides, it’s only for three weeks. It’s not like you’ll be gone the whole summer.”

“Jack, here, take this,” my father said, handing me a hundred dollar bill. “When you pick up your sister tomorrow, take my car. Stop and have lunch and maybe do a little shopping or see a movie or whatever. We’ll see you both back here for supper.”

“That’s a good idea,” Mom chimed in.

“Thanks Dad. Thanks Mom. I think Jill will enjoy that,” I told them.

The next morning, I woke around eight o’clock, grabbed a shower and a quick breakfast. It was almost an hour drive to the airport and I didn’t want to be late picking up Jill. I was out the door at nine-thirty and arrived at the airport about twenty minutes past ten. I had a cup of coffee to kill a little time before I made my way to Jill’s gate. Finally, I heard over the loudspeaker that her flight was arriving, so I stood up to be able to spot her. As I was watching passenger after passenger come through the gate, my gaze fell upon a gorgeous pair of legs in high heels. My eyes followed the long, tanned, legs up and up, they seemingly went on forever. Finally, high upon the thigh, came the hem of a short skirt. My eyes continued upwards, taking in the gentle curve of the hips and I could only imagine the outstanding ass that skirt must be concealing. I slowly continued my upward stare. At the top of the skirt was a bit of a bare, flat midriff, the same color as the legs, before the bottom edge of a tight t-shirt. My eyes continued to drink in the fabulous form. Next came the full, round, swell of the breasts. Beneath the thin fabric of the tight t-shirt, I could see the dark circles of the areolas and the erect nipples themselves, taking the time to even notice the wisps of golden blonde hair hanging down that framed this fantastic womanly chest. This fabulous figure was slowly moving directly towards me as my eyes continued upwards. The blonde hair was becoming thicker as my eyes moved over the neck, encircled by a single gold chain, over the slightly pointed chin, up to a perfect set of smiling, white teeth behind two full, red lips. Finally, I was staring at this vision of loveliness dead on in the face with an obvious bulge in my tight jeans, when I thought to myself, “Holy shit!”

“Jack!” I heard the familiar voice.

“Jill?” I asked, utterly astounded.

My sister flung herself into my arms and hugged me tightly. I was acutely aware of her belly pressing closely against my bulging crotch, knowing full well she must be feeling it.

“My god, Jill. Is that really you? I can’t believe it,” I said when she had stepped back.

“It’s really me,” she said with a smile. “I was going to ask you how you liked my new look, but I already ‘felt’ your answer,” she said with a grin and a wink.

I could feel my face becoming beet red with embarrassment. “I...I didn’t know it was you,” I stammered.

Jill laughed. “It’s alright big brother. I seem to elicit that kind of response from guys these days.”

“What happened to you? I mean, when did this...? How did this happen?” I was still flabbergasted.

“What do you say we get my luggage first and I’ll tell you all about it in the car on the way home?” she said.

“Yeah, sure. Don’t know where my mind is,” I said, still in a daze.

“I’ll bet I can guess,” Jill said and winked at me again.

She asked me to put her bags in the back seat when we reached the car, and soon Jill and I were on the road. I couldn’t help myself. Every chance I got, I would steal a glance at Jill’s long legs, which were even more exposed, with her short skirt riding up even higher as she sat.

“So, are you gonna tell me who you really are and where my shy, conservative, little sister is?” I joked.

“Remember I told you about my friend Connie?” she asked me. “Well, this is all her doing. I guess you could say she got me out of my shell.”

“How’d she do that?” I asked her.

“By being my friend,” Jill answered.

“Are you forgetting about Lisa?” I asked. “I thought she was your friend?”

“She is,” Jill began, “but Lisa was in the same boat as I was. She was the same as me. I love Lisa to death, but she couldn’t show me what I had been missing. Connie is different. She was popular when she was in high school, so she knew about things that Lisa didn’t. Besides, it’s not so much of a change. Just a little make-up here and there, I let my hair down, bought a few new outfits, and there you go.”

“You sure have ‘let your hair down’, I’ll give you that,” I said.

“Seriously, Jack. I’ll tell you. One night, Connie drags me over to her dorm room. She says she’s gonna give me a make over. She pushes me in the bathroom and tells me to take a shower and wash my hair. So I take a shower and wash my hair, and when I get out, Connie fixes my hair, show’s me how to do my make-up and dresses me up in some of her clothes. When she’s finished, she tells me to go look in the mirror, and when I do I look like you did a minute ago,” she laughed. “Connie tells me this is what I could be, if I wanted to. I was amazed. Then she tells me we’re going out and I’m like, ‘No way’. But she drags me out with her to a bar, and from the time we walk in, I notice all these guys staring at me and asking me to dance and wanting my phone number! And guess what, Jack? I liked it! I liked the looks and the attention. It was great!”

Now it was my turn to laugh. “Sounds like a little payback is in order.”

“Nah, nothing like that. It’s just that, for the first time, I didn’t feel invisible,” Jill sighed. “Anyway, since that night, I’ve been looking and dressing like this because it gets me noticed.”

“What about what you always used to say? ‘Brains over beauty any day.’” I asked her.

“Jack, I’m still me. But that naive little girl has grown up a little. In the real world, people notice things like how you look. I’m not saying that it’s right, but that’s how it is. Besides, no one ever said you couldn’t look good and be smart at the same time. I do still have a perfect 4.0 grade point average,” she chided.

“I guess. But hair and make-up and clothes are one thing. I never would have suspected what was hiding under those baggy clothes you used to wear,” I told her.

“Well, what can I say? It’s always been there, I just never used to show it off.”

My sister was certainly showing it off now though. I was still having a hard time getting over the change in her, let alone still having a hard time in my pants as well. I just couldn’t keep my eyes off her, even though I was driving. Jill didn’t seem to mind me glancing at her. In fact, I think she actually was enjoying it a little. She kept shifting in her seat, uncrossing and crossing her gorgeous legs over and over. She was teasing me, and I think she knew it. What’s more, I think she was enjoying it.

“Hey, Jack. You just drove right past our turn-off,” Jill said.

“Oh yeah, I forgot to tell you. Dad gave me a hundred dollars last night and said to take you shopping or to a movie or something,” I told her. “They’re not expecting us back until supper time.”

“Cool!” Jill squealed.

“So, what do you wanna do?” I asked my sister.

“Let’s hit the mall. I wanna get some new lingerie and maybe a new bikini,” Jill said smiling.

I drove us to the mall, and Jill’s first stop was in a lingerie store. I didn’t want to go in there with her, so I just gave her the hundred dollar bill and told her I’d be over at the computer store.

“What’s the matter, are you embarrassed?” she giggled.

I just gave her a little smirk and told her to take her time. I wanted to look at the digital camcorders and a few other things. I love computers and could get lost in that store. In fact, before I knew it, an hour and a half had passed when I felt a tap on my shoulder.

“Are you ready? I’m hungry, let’s get something to eat.” I turned around and Jill was standing behind me holding a couple of bags.

“Yeah, just browsing,” I told her. “I’m ready if you are.”

We stopped and had lunch and I asked Jill what she had bought. She said she would show me later. We hopped back in the car, and after just a mile or two down the road, Jill got up on her knees and leaned over the back of the seat.

“What are you doing?” I asked. Her ass was up in the air as I heard her opening one of her suitcases.

“I brought some of my old things. I want to change into them before we get home. I don’t wanna spring my new look on Mom and Dad just yet,” she answered.

As she was leaning over, fumbling in her suitcase, her little skirt had risen to the point where I could almost see the bottom of her ass cheeks. Jill was giving the oncoming traffic quite a show as well, as we received several whoops and hollers as well as honking horns. Finally, she settled back down in her seat.

“You want me to pull over someplace so you can change?” I asked her.

“No, it’s getting late. We don’t have time. I’ll just change here,” Jill said.

She kicked off her heels and, using the seat back as a brace, raised her hips high in the air so she could reach behind her to unzip her skirt. Slowly, she tugged it down over her gently rounded hips and down her lovely thighs before she plopped her gorgeous ass back down on the car seat. I glanced over while Jill had her long legs raised and was sliding her skirt down her shapely calves, and saw she was wearing a tiny pair of thong panties. Good god, but she had an awesome body, as the stiff cock in my pants could attest to. Jill reached for and pulled on a baggy pair of jeans. Then she slid her fingers under the edge of her cropped t-shirt and began to raise it. I nearly lost it and wrecked the car when the bottom of her breasts became exposed just before she stopped.

“Ooops, I forgot. I’m not wearing a bra,” she stated, as if I needed to be told. The way her nipples strained against the thin material, that fact was more than obvious. So instead, she slipped her loose blouse on over her t-shirt and buttoned it up. A pair of tennis shoes completed her ensemble, and much to my chagrin, she was beginning to look like the “old” Jill. However, knowing what was under the baggy clothing was enough to keep my dick hard all the way home.

Before we arrived, Jill had put her hair in a ponytail and had removed most of her make up with a moist towelette. By the time we walked in the front door, she looked almost like she had in high school, but I knew better. It was a good thing for me that I was carrying my sister’s bags or else I wouldn’t have been able to hide the huge bulge in my jeans from my parents.

The following week dragged by. Most of my time was spent poolside with my laptop, in the den on our parent’s desktop, or in front of the television. Jill and I went into town a couple of times and saw several people we knew in high school. Jill continued to be conservative, dressing in baggy clothing like she had all through school. But the images of my sister’s new look stayed with me and were enough to have me jerking off to them on an almost nightly basis. Afterwards, though, I would feel guilty about it. How on earth could I be spanking my monkey to my mental images of my own sister? At the time, however, I had never been more turned on. I was a good-looking, popular guy in college and had gotten my share of action with several of the campus honeys, but every time I tried replaying one of those scenes in my head, the girl I was with always turned into Jill, and I would ultimately fire a huge load of cum high into the air and all over my chest. I just couldn’t get Jill out of my head.

Finally, the day came for our parents to go on vacation. They had gone out the night before for some last minute things and the next morning I let Jill sleep in while I drove our parents to the airport.

As I was seeing them off at the gate, my father said, “Your mother and I left something for you in the den on the desk. Hope you enjoy it.”

“Thanks, Dad. You and Mom have a great time on vacation and don’t worry about us,” I said.

“Jack,” Mom said, “try and spend some time with your sister. She doesn’t have many friends and we don’t want her spending her summer being lonely.”

“I will, Mom, I promise,” I assured her. I watched them board their plane and stayed until it took off before heading back home.

Like a child at Christmas, I went straight to the den when I got back and found a bag on the desk from Mom and Dad. I looked inside and, lo and behold, it was the digital video camera I had been looking at in the computer store in the mall. I took it over to the couch, flipped on the television, and began reading the manual.

“Are they gone?” I heard a whisper from the doorway. I looked up and saw Jill standing there in her bathrobe, peeking her head around the corner.

“Good morning,” I said. “Yeah, I just got back from the airport.”

“Yippee!” she cried and came bouncing into the room and flopped down on the couch beside me. “Whatcha got?”

“The video camera I was looking at the other day. It’s from Mom and Dad,” I told her.

“Wow, lucky you,” Jill said in mock surprise. “Wonder how they knew which one to get?” A sly grin crept across her face. “So, whatcha gonna record?”

“Well, nothing until tomorrow. I’ll have to charge the batteries for a day,” I told her.

“Awww, too bad,” she pouted. “Well, we got the whole house to ourselves for the next three weeks anyway. I’m sure something will happen in that time that you can tape.”

“We’ll see,” I looked up from the camera’s manual and smiled. “Got any plans for today?”

“As a matter of fact, I do. Lisa got home yesterday and I’m going over and spend some time with her. You got any plans?” Jill asked.

“Probably just play around on the computer and watch some television,” I told her.

“Oh, poor baby, no one to hang out with?” Jill asked.

“Hey, I’m on vacation. I’m just gonna be lazy for a while. Trust me, I don’t mind a bit.”

“Ok, well you have a good time being lazy. I’m gonna take a shower,” Jill said standing up and stretching. As she did, her long robe fell open, exposing her gorgeous legs. I watched Jill’s ass sway back and forth as she walked from the room, then went back to my manual. I had a feeling that watching television and playing on the computer wasn’t all I’d be doing today.

After I finished reading the manual, I installed the software on my laptop, then jumped on my parents’ desktop and connected to the internet. I messed around there for a couple hours, then watched a movie on television for another couple hours. The movie was a soft-core porn with some hot looking babes, and halfway through I had my dick out of my pants and was lazily stroking it. As had become the norm lately, my thoughts were turning to Jill. Why was I doing this, fantasizing about my own sister that way? It was so wrong. For crying out loud, this was my sister I was getting a hard-on for! But my imagination just wouldn’t let it go. I turned the television off and decided to take my boner upstairs to my room with me. I’d feel guilty about it later, but right now I had to take care of business.