**Background**:
My name is Jake. I have one older sister, one younger, and one youngest brother. I am 22 and in graduate school. I'm 5'9", and I work out, but not often. So I'm not fat, but also not muscular or toned. I don't know what a girl would say about me, but I believe I'm a little above moderately handsome. My last girlfriend was when I was 18, freshman year of college. She was a borderline slut, and I guess you couldn't really call us boyfriend/girlfriend since we didn't get much one-on-one time. It was more like friends with benefits, minus sex. Whenever we were together, we were either with a big group of friends or we were alone kissing and petting instead of getting to know each other. The last couple weeks we were dating, I started getting my hand in her pants, which ramped up into eating her out. Since that was the first girl I've done that with, I wasn't any good, but I learned some of the dos and don'ts. But she never returned the favor, and that was the furthest I had ever gone with a girl.
My younger sister's name is Jackie. She's 19 and in her last year of high school. She was held back a couple years for comprehension disorder that no one had diagnosed. But she's not dumb, and after they discovered it and gave her accommodations, she's been doing well enough to attend a summer camp this summer that our state does. The camp is for the smartest kids in the state, and if you get accepted to the camp, the state will pay your tuition to any state university. So there's a little less than 3 years between us, but we're 5 grades apart.
Jackie is 5'4" with dirty blonde hair about shoulder length and a naturally attractive face. She's one of those girls that spend an hour every day working on her hair and makeup, so she always looks very pretty. She wears 32C bra, which should tell you she's shapely without being fat. She has a noticeable hourglass shape and a butt the size of a basketball. Okay, the butt might be an exaggeration, but my point is that she doesn't work out and it still seems like the only place on her with any fat is her butt and chest. She also has a personality that everyone enjoys. There are plenty of people she doesn't like, but I can't think of a single person who thinks negatively of her. She has a very welcoming, kind, and charismatic personality and has the gift of striking up conversations that are interesting to people of any background. So this amazing personality, shapely body, and beautiful face/hair combines to form a girl who guys literally fight over. Her last breakup was at the beginning of summer with a guy who didn't want to be tied down to her while she was away at that scholarship camp all summer.
We were open with our relationship details. I knew she had never had sex or let a guy see her naked. She told me one time that her last boyfriend tried to finger her, but there was no kissing or anything to lead up and she was nervous, so she was too dry for him to get a finger all the way in. But I did know that she masturbated with her fingers starting in early high school. One of my friends and I accidentally walked in on her once, and as a joke we bought her a vibrator. I knew it was a joke and I really didn't think she would keep it, but after that I could hear a light buzzing sometimes when I passed by her bedroom door.
One last thing about Jackie is that she always wears thongs. She first started wearing them in early high school only with dresses and tight clothes so the panty line wouldn't show. But then she started to like the feeling, so she moved to only wearing thongs. The only exception is when she's wearing athletic shorts, the baggy kind with the inside liner, not the skintight ones. She always rolls them down so the waist is low and the legs are high, and she never wears underwear with them because "it already has the liner."
**Our relationship**:
Jackie and I have always been a lot closer to each other than our other siblings. I mean, we care about our other siblings, but the older one has a different personality, and the youngest can be annoying. We usually hung around each other despite being 5 grades apart. When I went to college, we called each other about once a week. I'm not sure why I didn't get a girlfriend after my last one. I always figured I just wasn't interested. Then I started talking to Jackie gradually more frequently until it got to the point where we were texting through most of the day every single day my senior year. Over Christmas break, I gave in to the thought that I might be attracted to Jackie, and as soon as I broke that mental barrier, I realized I am in love with her. I knew there was nothing I could do about it, and I have really good control over not letting my emotions control my words or actions, so I was just able to push it aside for the next year and a half, but I couldn't get rid of it to the point where I was willing to chase other girls. At this point, I have no idea what Jackie thinks of me, but I didn't suspect that she had any feelings for me because that's not how brothers and sisters usually feel.
Jackie and I have two very strange elements to our relationship. One is that I frequently give her massages. When I was in early high school, my friend's mom was a masseuse. I stayed at his house one night, and she randomly decided to teach us both how to give massages (on each other). It was weird and awkward when she taught us, but I'm forever grateful for that because of my ability to relax girls by feeling their bodies! I didn't care who I gave a massage to, and it usually wasn't sexual. I'm a nice person and I like to know that my talent can help my friends. Of course it feels different when I massage a crush, but I would give massages to anyone who asked me, which was usually my family, girls who were friends, and girlfriends. But no one asked for more massages than Jackie. She ran track until she was 16, and she would often ask me to work out her cramps. After she could drive, she quit sports and got a job, and her legs and back would be sore after every shift from standing for so long. Like I said, there was nothing sensual at this point, even when I massaged her after I realized I love her, but it still wasn't a normal brother/sister relationship.
The second weird thing is we give each other what we call "unexpected kisses." It started when we were kids with "unexpected taps." We would tap each other and try to surprise the other person. If you could surprise the other, you got one point. We would keep track of points on a piece of paper at first, then on our phones as we got older. We kept track of each other's points to make sure they didn't cheat. Then the next time we went out to dinner, whoever had the most points would have to buy the other person's drink, even if our parents or someone else was paying for the rest of the meal. Sodas aren't expensive, but they always tasted better knowing you made the other person pay for it, and while we were in grade school, we weren't usually allowed to have a soda unless we bought it ourselves, so it was a rare treat and satisfaction of winning. But anyways, the taps eventually stopped working as often, so taps grew to pushes, slaps, and sometimes hits (we were in grade school). Our parents obviously didn't want their children beating the shit out of each other for a soda, so mom suggested we do "unexpected kisses" where you would get a point if you could make them flinch, try to get away, or wipe off the kiss. Being in grade school, we didn't think it was weird, so we would try to rush in at their face for a kiss trying to make them flinch, kiss them in front of friends or other embarrassing places to make them try to get away, or give them sloppy kisses on the cheek or other places to try to make them wipe it off. When we got older, we knew kisses on the lips were weird (but we would still do it to make them try to get away), so we mostly stuck with the cheek/arm/leg/etc. But because we kissed so much as kids, I guess that broke that taboo for us, so we never stopped playing that game and this was never a sexual thing for us.
**The Story**:
So as I was saying, my sister is 19 and looking at colleges. Since she went to that camp, my parents really want her to go to a college in state, but she's on the fence between one out of state and one in state (my college). So I was going home for 2 weeks between my summer and fall semesters, and my parents asked me to take her back with me for a week so I could take her to classes with me and to university activities and do things in the city. They thought that a week having fun at this college might convince her to stay in state instead of leaving.
The first week home passed uneventfully. I gave Jackie daily massages (even on days she didn't work because she missed them), and we kept playing "unexpected kisses," but I'm good at keeping my emotions in check, so there was nothing sensual about this. Most of my old friends were out of town, so I spent most of my time with my family or hanging out with Jackie. It's a 3 bedroom house, so we had parents, girls, and boys split up. I stayed in my brother's room, but our older sister lives by herself, so Jackie had her own room. We spent most of our free time in her room watching movies that our brother wasn't allowed to and our mom wouldn't approve of, but we were adults, so they let us do what we wanted.
Her school started the second week I was there. There was a competition that over a quarter of our school goes to every year, but it's always mid-late August. So every year, the school starts 3 days (Wed, Thu, Fri) before everyone else, then has 3 days off, then continues as normal. So my parents said we could leave on Friday, her last day of the first week, go to my school for a week (she would skip Thu and Fri of her second week), and then my parents would pick her up from my apartment.
On the Wed before we left, she came home exhausted. The geology teacher at our high school is a dick (I warned her to choose a different science elective), and he always gives a test the first week of class over a bunch of geology terminology that you shouldn't know. He says it's so you can retake the test after a month and see how much you've improved, except this first test is worth 5% of your total grade for the entire year! Then she had work straight after class. So she came bursting in her room (where I was watching a movie) after getting off work at 8. She said, "Jake, stop your movie and give me a massage. I'm pissed as hell about this test, and customers at work are fucking idiots, and [my boss] is an idiot, and I really need to calm down."
I said, "Okay". I must have looked confused because she apologized and asked me to follow her to the bathroom. She always washes her feet after work just to make sure they don't smell so that I will give her a foot massage. So while she washed off, she talked about the stupid things people did at her work, then she asked me to wait while she changed out of her work clothes. When she opened her bedroom door again, she was wearing a loose tshirt and athletic shorts (which means no underwear). I was wearing a tshirt and athletic shorts as well, although I still had boxers on. She lay on the bed on her stomach and opened her geology book to start studying the questions at the end of the chapters.
From her frustration, I knew she wanted more than a foot and shoulder rub. I can take 30 minutes to an hour doing a good full body massage, so I started mentally prepping myself for the long haul. I can give a massage while standing on the side, and it's actually a little easier, but you need a thin bed so that you can stand on both sides, or make them get up and turn around halfway through. I decided against any kind of bothering her, so the best way to get both sides is sitting on top, with my butt on her butt. I was about to climb on, and she said, "Wait. Do my arms first. They're sore from carrying stuff at work today."
