The Oblivious Teen (Skylar Pt. 1)

Older brother (16) sees his sister (14) naked and slowly obsesses over her. (No sex, a little bit of mast, but mostly set up for more)

Parts of this story are true, parts of it are fantasies I've had for years now. Depending on how well this one does, I'll post a part 2.

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I remember the first time I started to have sexual feelings towards my little sister. It was summer break, I had just gotten home from my friend Jackson's house. We were talking about how badly we wanted girlfriends, or at least a naked girl that we could play with and explore. This was in the early days of the internet, pre-iPhone, and both our families only had one PC. Mine was in the living room, right in the middle of our house, while Jackson's was in the basement of his house. We'd take turns watching porn and jerking off while the other one played video games on the TV downstairs. The computer was located around the corner from the stairs, right next to the bathroom, so anytime we'd hear someone open the door we were able to quickly close out tabs and duck into the bathroom so nobody would know what we were doing.

I was right in the middle of watching a cute blonde teen get fucked from behind when Jackson's dad said he needed to use the computer for work for a little bit. I quickly closed out of all browser and hit the power down button before whipping around the corner into the bathroom. After a few minutes I flushed the toilet, washed my hands, sprayed a bunch of air freshener and turned on the fan and acted like I had been taking a dump. Jackson's dad looked at me with a smirk on his face, "Looking a little sweaty there kiddo, you alright Levi?" He asked.

"Just fine Mr. R!" I said, thinking of an excuse for why my face was flushed, "the sun shining threw the window just keeps the bathroom warm is all."

I was thankful that Mr. Roland always announced himself at the top of the stairs before coming down. Jackson's mom would just open the door and walk down with a plate of cookies, pizza rolls, or other snacks from time to time when we were down there. Which wasn't ever a problem when we were actually playing video games. One time I started running up the stairs and bumped into her, knocking a full plate of bagel bites to the ground on "accident" because Jackson had decided to plug some headphones in and listen to his porn on full blast while beating his meat. I made a bunch of noise apologizing to his mom hoping that he'd hear it. After helping her clean up the mini bagels and pizza sauce I returned down to tell him he's lucky I saved him.

When I turned the corner I saw my best friends pants still around his ankles, stroking away at his dick oblivious to the world. I looked to the computer screen to see what he was so focused on, and instantly popped an erection of my own. There was a young girl on the screen, she couldn't have been older than 15 or 16, stroking a cock with a mouthful of cum. It was the first time I had seen a scene with someone my age in it, and watching the cum drip out of her mouth and onto her growing rack had me in a trance. I finally snapped out of it when I heard Jackson start grunting and realized I was about to see my friend splooge all over himself. Having already felt like I crossed a boundary seeing his dick without him noticing, I turned back around the corner and hopped on the couch and started playing Mortal Kombat, acting like I hadn't seen his illicit video, or his dick.

Jackson and I went upstairs after his dad kicked us out of the basement for the day. I decided I was going to walk home and try to find my dad's porno mags before my parents got home since I was still horny. On the 10 minute walk back to my house, the memory of that teen girl dripping cum kept playing in my head. I was going to have to ask Jackson where he found it or have him show me the sight so I could jerk of to it too.

I walked in the door and the lights were all off. Mom and dad wouldn't be home from work for another couple hours, and my sister Skylar was probably at her friend Molly's house as she usually was during the week. I walked to my parents walk in closet to start searching for my dad's porn and grab a wash cloth for once I finished. My sister and I's portion of the house was being redone, our shared bathroom as well as our rooms were being remodeled, so all the towels were in our parents side of the house. That was also the only working shower we had at the time.

As I turned the corner into my parent's closet I saw my little sister in the amour grabbing a towel. She was completely naked, her little butt pushed slightly out while she leaned forward, likely looking for "one of the softer towels" she liked to use. I had seen my sister naked plenty of times before but it was only a quick flash here and there as she changed since she'd hit puberty, and I'd never done it intentionally.

For the first time I saw how rounded her little ass was. I looked down and saw the tone of her small, athletic, cheerleader legs. For the first time in my life, I was getting turned on by my sister; fantasizing about her reaching back and spreading her little cheeks apart and exposing her butt hole. As she opened the next cabinet door in the amour to grab a washcloth, she dropped it on the ground in front of her. I watched her bend at the waist, giving me a full view of her developing butt. I saw the smallest little folds of skin underneath her as she bent down, getting my first ever glance at real life pussy lips.

I turned around the corner and hid against the wall of my parents room hoping Skylar hadn't caught me sneaking a peak at her. I was rock hard, my young 6 inch shaft putting a full tent in the athletic shorts I was wearing. I heard my sister close the door to the closet and walk away down the hall towards the bathroom and turn the water on. She hadn't seen me. I don't think she even knew I was home. I got on all fours and crawled my way to the bathroom. As I peaked my head around the corner slowly, I saw my sister testing the water temperature. As she turned to the faucet to make the water hotter, I got the a quick glance of her from the side. Her little tits were coming in more; she just made the move to a training bra a few weeks ago, having worn tank tops under most of her shirts before that. From the side, her boobs looked like little pointy pyramids; the couldn't have been bigger than half an orange each.

Her light brown hair was down, going halfway down her back. She pulled it all back behind her and out of her face before stepping in. As she did I saw one of her nipples. Her small areolas topped her conical little breasts, her young nipples poking out slightly; like a perfect little cherry on an ice cream cone. As I was crawling down the hallway I must have shimmied out of my shorts without noticing, because I was suddenly aware of my cock out, the cool air of the hallway on my shaft as my hand reached around it.

I kept watching my sister hungrily, this was the first time I'd ever seen a girl naked. I started to see my baby sister as someone I wanted to have sex with, not just an annoying little pest I had to share a room with while our house was remodeled.

At 4'10" and less than 100lbs, Skylar was one of the shorter girls in her class. She was picked to be the flyer on the cheer squad in 8th grade because she was the smallest out of all the girls. She was constantly picked on by the girls that weren't in cheer for her small frame and lack of tits. I had heard her crying about it to mom after school one day, asking when she'd start to develop more and get tits like the girls in school. My mom had told her that she had grown 4 bust sizes and shot up 5 inches right before she had turned 16. She had to produce extra identification at the DMV to get her drivers license because of how much she had grown in the 6 months since getting her learners permit; the man doing her paperwork didn't believe it was her before.

Skylar was still small for her age, looking at her most people would have probably assumed she wasn't even a teenager yet. She still had a small baby face, her large hazel eyes and freckled face peering up at everyone she talked to. Maybe that was the reason I hadn't realized she was starting to develop. But as I stroked myself watching her shower, all I could imagine was running my hands along her nude body. Licking every inch of her skin and rubbing the swollen head of my dick against her. I thought about the girl in Jackson's porn. I pictured my little sister, gagging on my cock, my cum and her spit running down her face. Imagining her stroking me as covering her little tits in streams of my cum.

Picturing my little sister rubbing my cum on her nipples sent me over the edge. I quickly looked around for something to catch it. 2 feet in front of me I saw my sisters clothes. I quickly lunged forward and grabbed them, pulling them back into the hallway out of sight as I shot a load into my sisters pink training bra. It was the biggest load I had ever shot to that point. I must have let out a grunt or a noise, "Levi? Dad? Whose there?" I heard my sister scream, a slight note of terror in her voice.

"Its just me Sky," I panted, light and the rest of the world coming back into focus, "I just ran home from Jackson's and was gunna hop in then saw your clothes sitting out here and heard the shower running" I said from the hallway, hoping that I could trick her into thinking she stripped before getting to the bathroom.

"I'll go ahead and throw your dirty clothes in the wash with mine, hurry up so I can clean up too!" I said, as I walked down the hallway that connects the bathroom to the master bath.

"I got here firrrrrrst" Skylar shouted in a sing-song voice, "you'll just have to wait! But you can take my clothes!" I heard her say as I walked towards the laundry room.

I grabbed a towel out of my parents closet, and walked out. I wiped the still leaking cum off my cock and into my sisters bra as I walked to the laundry room. Thinking about my cum being where her nipples were not even 10 minutes ago was getting me hard again. As I tossed her cum covered bra into the washer and stripped, a perverted idea crossed my mind. I pulled her underwear out of her shorts like they were made of gold. I looked at them, trying to figure out which side was which. They had one of the care bears on one side, and were plain purple on the other. I figured the side with the bear must be the front. I flipped them inside out and put them to my nose, inhaling her scent deeply.

Skylar's 14 year old panties were still warm and fragrant. They smelled a little like sweat, and something sweet and musky. I was rock hard as I pulled them away from my face, and thats when I faint line of moisture inside them. Not knowing what discharge was, I assumed at the time it was pee. Not caring about what it was, I immediately started licking it. Whatever it was it tasted sweet, and had a smooth feel as it coated my tongue. I was jerking myself off while I sucked on my sisters panties. In bliss at the little bit of taste I could suck out of her freshly worn undergarments.

I moaned, knowing my sister was in the shower and too far away to hear. I imagined licking her little pussy while she jerked me off. As my balls tightened for the second time in less than 10 minutes, I felt another orgasm coming over me. "Oh fuck Sky, you taste so good" I said, pulling her panties out of my mouth and covering my dick with them.

I watched, feeling slightly guilty for getting off to my baby sister, as her wrapped her saliva soaked panties around the head of my cock. The warmth from my spit, the taste of her young pussy on my tongue, it was heaven. I felt my member jerk in my hands as I saw her childish underwear get darker with my cum. My legs almost gave out right there in the laundry room as I filled her little undies with my seed.

When I regained my composure I threw her soiled underwear into the washer. They were almost completely covered in a mix of my spit and semen. I wiped the last bit of my dribbling cum onto her shirt, before tossing that and her shorts into the wash. I stripped, putting my dirty clothes into the laundry as well, before wrapping the towel I grabbed around my waist. I threw the couple clothes in our shared room into the wash, loaded it with detergent and softener, and hit start, washing away the evidence of what I had just done.

I sat on the couch, red faced and panting in my towel, waiting for my sister to get out of the shower. As my dick deflated, I was hit the guilt over what I had done. I felt like a pervert for fantasizing about my sister. But no matter how hard I tried, I couldn't get the image of her naked body out of my head. The little bumps of her breasts. Her sexy little bottom. Her little virgin "... wait a minute" I thought. I hadn't actually seen her pussy. I couldn't imagine it because I hadn't seen it. What'd her bush look like? How hairy was she? Did she have big lips or small lips?

As I sat on the couch trying not to get a third hard on in an hour, my sister came out from my parents room. Her wet hair was matted to her face and shoulders, her arm holding the towel up around her chest and bottom. "Damn those 'soft towels', they're longer then the regular ones" I told myself, "maybe I'd get a glimpse of her ass or her pussy if she was using a regular one"

Then an idea popped into my head "hey come here real quick Sky" I said to her as she walked by the couch

My sister walked over to me, a questioning look on her face, "what do you want Levi?" she asked

I looked her up and down, water still dripping from her hair, as I tried to think of how to see her naked "I was just wondering where you went today, when did you get home?" I said, trying to act casual

Skylar looked at the clock, "like a half hour ago maybe" she said, "me and Holly were exploring the little woods they have, and I didn't wanna be dirty when mom got home"

"Oh, well next time leave some lights on or something, I almost walked into the bathroom to take a shower and didn't know you were home." I told my sister

I stood up and started towards my bathroom, holding onto my towel as I walked past my sister. "Well get home earlier next time and you can turn the lights on" Skylar said sassily, "I don't know when I will and won't be back, Holly and I wanna explore all the way to the creek this summer"

My sister started walking towards our rooms when the idea hit me.

"Next time you guys go, I hope you have a good TRIP!" I said, kicking out my foot and giving her a little shove in the shoulder.

Skylar tripped over my foot and lost the grip she had on her towel. I quickly stepped on the end of her towl as she stumbled and pulled it off her as she fell away from me. She screamed as she fell to the floor, "you know its summer time not fall" I laughed as she landed on her knees away from me.

When Skylar landed, knees spread out to try and brace herself, I got the shortest glimpse of her cute little hole, it was clenched tightly as she flexed her body in pain hitting the ground. Before I could appreciate the sight in front of me my sister was back on her feet and turned around. My nude sister stood less than 3 feet from me. I put my hand out in front of my face, partly to block the hit I knew she was going to throw at me, but mostly so that she couldn't see my eyes looking straight at her crotch as she turned around. She didn't have a bush like I was expecting. There was just the littlest bit of hair, almost what I had when I tried to grow my first mustache. The small patch of light brown - almost blonde hair, hadn't even fully grown yet.

I kicked her towel at her "oh god cover up!" I yelled, hoping I sounded convincing.

My sister, not being shy, and probably forgetting that she shouldn't be nude around boys, especially her brother, swatted the towel away and lunged at me. "You're such a dick!" My sister screamed, her arms flailed wildly towards my face.

Being nearly a foot taller, and at least 60 pounds heavier than her, I was able to catch my sisters wrist in my hand with ease. She swung at me with her other hand, and I moved her wrist to catch it. I now had both my sisters arms in one hand being pulled up over her head. Skylar looked up at me with a look of anger on her face. As that little freckled face glared up at me, I looked her sexy little body up and down and felt myself getting aroused again.

My sister looked up at me and stared into my face, if she had laser vision she'd have been burning my eyes out of my head. I looked into her eyes, noticing the little grey flecks in her green eyes. After a moment my gaze started to drift downwards towards her young breasts. My sister blushed and yanked her hands away, covering her small tits with one arm and her little mound with the other. I grabbed her towel from the floor, pulling my torso back to try and hide my hard on. "Sorry sis, I guess that wasn't as funny as I thought" I half heartedly said.

"Don't push me like that, it isn't very nice" Skylar said, a look of hurt on her face as she took her towel from me. "What if I'd have slipped and broke my neck because I was wet?" She asked

An image of my motionless, naked, little sister passed out on the floor went through my head. "Guess that would have been bad... Sorry" I told her, walking away to go take my shower.

While I did feel bad about hurting Skylar, the idea of having her body all to myself gave me my third hard on since getting home. I stroked myself in the shower thinking about her, About feeling every inch of her. Covering her in cum while she laid there. Tasting her sweet little pussy, running my hands through sparse bit of peach fuzz she had on her crotch. Sucking on her little nipples. For the third time that day, I came thinking of my little sister.

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Everything was normal for awhile after that. My sister was a little embarrassed for a day or two and couldn't make eye contact with me except to give me dirty looks. But she got over it before the weekend.

Since our rooms, and the bathroom, were bring remodeled at the time, we shared a room. Both of our rooms were getting bigger, our bathroom was getting turned into one of those Jack and Jill bathrooms. We were both looking forward to the bigger space, and the ability to brush our teeth and get ready at the sink while someone else was using the shower or toilet, but that was still at least one, if not two months off from being finished. In the meantime, we were both in what WAS my sisters room while mine got worked on. We had our beds on opposite sides of the room, and both had a pop up closet type thing between them, making a makeshift wall of a sorts so we could change. But I realized that if my sister's lamp was one while she was getting dressed, the back side of the "closet" was almost see through.

Whenever my sister would go shower at night, I would make sure the lamp was on for her side and turn mine off. "I'm tired, I want my side dark so I can sleep" I'd tell her.

In reality, I would be slowly stroking my cock waiting for her to get in from the bathroom and change into her night clothes. Sometimes I'd cum while she was getting dressed. One night I caught her playing with her boobs a little before throwing on a nightgown. From my spot in my bed "sleeping" I could hear her let out a loud sigh when she pinched her nipple. The look on her face was like she had enjoyed it. I came right there looking at her. She turned and looked at the closet, unable to see through "What was that noise?" She asked

I mumbled, trying to act like she had just woken me up. "What noise? Me?" I said, half lifting my head, feeling my cum puddle in my lap. I continued to play with my shrinking cock as I watched my sister.

"Its a good thing I'm a heavy sleeper," Skylar said "You snore sometimes and make noises before I fall asleep, its annoying"

"Sorry" I told her, laying there forming an idea.

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Names have been changed, and this happened over 10 years ago. But most of those details in this one are the same. Its when I started obsessing over my little sister. She was the first pussy I ever tasted. She ended up being my first for a lot of different things. Part 2 will have a bit more fantasy, but will include real details about how I started touching my sister in her sleep. To this day, I don't think she knows how much I touched her. But I did eventually cover her little chest in my cum, twice.