Innocent Game of Unexpected Kisses

**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."

So I stood beside her and massaged one arm from the shoulder to the hand while she used her other one to turn her pages. After I finished, I started to climb over her to sit on the other side and do her other arm. I got a little mischievous, and kissed her cheek on my way over. She didn't even flinch, looked at me, and said, "Seriously? I'm pissed and you want to annoy me with that?"

I felt bad, so I said, "Sorry", and started massaging the other arm. After a minute she stopped reading and told me a funny story that happened in school that morning. We both laughed about it, and that made me relax to know she wasn't still fuming. After finishing her arm and starting her hand, I spread two of her fingers out real wide and gave a sloppy kiss in the webbing between the fingers. She said, "What the heck?!?!" and instinctively jerked away and wiped it off. She saw me grinning, so she pulled out her phone to mark down my point. We made eye contact and then both started laughing because I got her with an unexpected sloppy kiss in a strange place.

That laugh brought back my playfulness, and I started trying to get her with kisses on her arm while I finished massaging her hand. Then I straddled her and sat down on her butt to begin a back massage. I rubbed her shoulders and back down, and every few minutes tried to give a hard or sloppy kiss to make her flinch or wipe it off. Problem was that I could mainly only reach her shoulders or the top of her head when I bent over, so it wasn't very effective. I kept trying though.

After 10 or 15 minutes, she asked me to focus more on her lower back. Sitting on her butt lets me reach her shoulders easier, but my legs get a little in the way of the lower back, so I don't usually spend as much time on that. But I scooted down so that I was sitting on the back of her upper thighs so that I could spend more time on the lower half of her back. After a minute, she said, "No, my lower back, not the whole lower half. Just that lower part feels like it needs it."

Well focusing on only the lower part meant that I would inadvertently touch her upper butt more frequently. Normally no big deal since I would go this low with everyone if I was standing beside them. But then I bent down for another kiss, and I noticed that my lowered distance allowed me to reach more than the top of her head and her shoulders. So I made a last second adjustment and kissed her right in the bend of her neck. She jumped a little, so I knew I had a point, but between the bending over, kissing in a sensual place, and her little jump, I was then suddenly very aware of my crotch pressed against her ass. I sat back up slowly and I saw her mark down my point.

Once in a while, I would bend over for another kiss in the same spot, or on the other side of her neck. She didn't flinch anymore, but it seemed like the points didn't matter to me anymore. All I could focus on was being pressed against her ass while I gave her a kiss that started to mean more than just a game. And while I did this, I massaging the top of her butt more and more frequently. Once when I bent for a kiss, it felt almost like she backed herself into me more while I kissed her. I wasn't sure, but I knew I was heading down a slippery slope, especially if she didn't think of me the same way that I love her, so I decided to turn around and do the legs.

I picked up one leg so it was bent upwards at 90 degrees. I massaged her foot, and would occasionally give her kisses on the foot or calf. I switched to her other foot and started doing the same thing. Then I massaged up and down her calves before moving to her thighs. I laid her feet down and scooted back so I was sitting a little above her butt. I massaged her thighs, which was feeling much more sexual than any other time I had done this for her. I kept bending over to kiss random spots on her legs, which would press my crotch into her ass again.

Once while my hands were moving up her perfect thighs, I thought of that from middle and high school called "Are you nervous yet?" You would start with your hand at her knee, and then slowly move up pausing with every inch moved until she said "stop", which was when it was her turn to do the same to you. The point of the game was to work up to where she would let you cop a feel, and to sneakily say stop at just the right moment so she gets a little further than last time, but doesn't get grossed out that you let her slide all the way up to your crotch.

So anyways, I thought of this game, but my hands were already moving all over her, so I decided to try it with kisses. Despite that I was beginning to be aroused, I wasn't planning on kissing her ass or anything. I just wanted something entertaining towards the end of this long massage. So I bent over to start, and I realized I couldn't start at the knee from how I was sitting, so I started at her ankle. I used one hand to support myself and my other hand to keep massaging her thighs. Fairly quickly, I went all the way up to a little above her knee, so I went back down the other leg. When I kissed her other knee, I felt her butt tense a little under my crotch. I knew I could get another point if I have a sloppy one there next time! But after reaching her second ankle, I realized that was too quick and not as fun, so I kissed three in a row before moving up. One on one side of her ankle, one on her heel, and one on the other side, and I snaked up like this while I did, slowly getting sloppier and sloppier. Then when I switched legs, I gave her a big wet one on the back of her knee, and she jerked under me.

I looked back at her and laughed, and I saw her mark another point on her phone. She said, "Get off of me! You're crushing me, and I don't want you to scare me like that again!"

So I did, and I asked, "So I guess we're done. Are you feeling better now?"

She had an expression on her face that I hadn't seen before. Tentatively and quietly she said, "No. Um... Since you've been sitting on my butt this whole time, now it's sore. Can you somehow relax it?"

I halfway didn't believe what she just asked me. "Well, I've never given a butt massage before, but I'm willing to try if you want."

She said, "Okay", so I stood behind her. She scooted down on the bed so her feet were hanging off, and I stood between her legs. I could feel my hands starting to shake as I started massaging the top of her butt. I slowly and carefully worked my way around the whole thing. After one nervous pass, I got a little more confident and started massaging it like it was no big deal.

But it still felt awkward just staring at her and rubbing it, so I wanted to do something else. My aroused mind had reached stupid mode, so the only thing I could remember was the "are you nervous" game I was playing earlier. So I stretched my arms up to continue massaging while I started kissing from as low as I could reach, which was about mid-calf. I didn't like the dry skin on dry lips, so with every kiss, I puckered my lips and opened them a little so there was a little moisture. I started snaking my way up, and she said, "Not behind the knee."

So I skipped the knee and went to her thigh. I kissed back and forth and slowly upwards. I kissed about an inch away from the pants leg of her already very short shorts, which meant I had kissed higher up my sister's thigh than any brother probably should. So I switched to her other leg at about the same place where I stopped and I started moving down. I skipped her knee again, and I moved a little down her calf. I realized what a pain it was to stretch out so far while giving a massage, so from then on, I just started above the knee.

With the next pass back and forth, I kissed right along the hem of her shorts. With each pass after that, I started grabbing more and more of her ass in my hands, reaching deeper into her crack and inner thighs while simultaneously pulling her shorts up higher so I could kiss higher on her thigh. Eventually I got them up to the point where I was kissing right along the liner inside the shorts, which basically meant I was kissing her panty line.