Jake and I always had a pretty lax relationship. It was definitely something that was for monetary gain; he'd pay for the movie tickets, the tacos, and all that, and he also had a car. I had the advantage of being pretty good-looking and having a good personality, charisma, intelligence. But besides money, there was something else that had always kept us friends, and that was his sister.
Jake's sister, Kaitlyn, was the only redhead in his family. She had just turned 14, so a lot of my interest in her had to do with the fact that I shared a few hobbies with her, and it wasn't sexual; she was really into video games and comic books, and that sort of thing, but don't get me wrong: she wasn't one of those hipster-type girls. Kaitlyn was the kind of girl you'd never believe would even pick up a comic book, because there was something very ... feminine about her. I could never put my finger on it. At the time, I didn't think it was sexual at all, so I never hesitated to greet Kaitlyn and chat her up. Sometimes my eyes would quiver and fall upon her cleavage (or what little she had), but that happens to every guy, doesn't it?
So I was hanging out at Jake's place, and Jake told me he wanted to go make a run down to Fry's to capitalize on a deal. Fry's was about 45 minutes away, and his parents weren't home, so he told me it was alright if I stayed at his house and kept an eye on his sister. For some reason, I happily agreed to stay at his house; Kaitlyn and I had been watching Scrubs on TV for the past hour, and we weren't getting bored, so Jason left and drove off.
We were talking about the characters on TV; Kaitlyn liked animated shows and started talking about Avatar: The Last Airbender. I'd seen the show a few times, so I was able to talk about it pretty thoroughly. We started talking about how the relationship between Aang and Katara never consummated, and how disappointing it was Katara never realized how much Aang liked her. The conversation was making me more excited than it should have, but pretty soon, I could tell she was getting bored. I didn't know what else to say, so we sat in an awkward silence as she bounced softly on the cushion, watching Scrubs credits for a couple minutes, until she finally said, "Be right back..."
"Better get your ass back here soon!" I responded jokingly. Immediately, I realized I'd overstepped my bounds. We didn't really know each other very well, so she gave me kind of a strange look, but then finally darted off upstairs. Pretty soon, I heard the water running through the pipes and realized she was taking a shower. Now I was starting to feel a little out of place, regretting my agreement to Jake. My dick had been rubbing a little bit all day, so I took a look around me, then stuck my hand in my pants and adjusted myself. I was also getting sort of hard. This was the opposite of what I wanted; I didn't want to seem like some weird horndog to Kaitlyn, so I decided to make a trip to the bathroom to rub one off, just so I'd be less horny.
I walked into the hall bathroom and shut the door, turning on only the shower light, which was very dim. I whipped out my dick and started rubbing it; I saw a bit of lavender oil on the countertop, and squirted some on my dick, and then started masturbating rapidly; I was already about to cum, but I slowed down and held it. Once the sensation had gone away, I started in again; my dick was getting so hard it almost hurt, but that made it better. Suddenly, I noticed that the water had stopped; Kaitlyn must have finished with her shower. I hurried to try and finish up; I was still too hard to put my pants back on.
Then I heard a creak by the door, but I didn't respond because I assumed Jake's sister knew I was in the bathroom. But to my horror, the door swung wide open seconds later, and I heard a gasp. I saw Kaitlyn standing in the doorway, a white towel wrapped around her slender body, her red hair still wet. The muted light played upon her features and accentuated her silhouette. I gulped.
"What are you doing?!" she exclaimed. I struggled to put my cock back into my pants, but at the same time, still slowly rubbing it. "Err ... Sorry ... I was just..." "Ewww!" "I know, sorry; here, let me shut the door!" I stumbled at her, but she was standing right in the doorway, blocking me. "I'm telling Jake! And I need something from in here, so GET OUT!"
She was still blocking the door, but I shoved my still-hard cock all the way back into my pants and uncoordinatedly navigated around her. I didn't know where to go, so I just stood in the doorway as she pushed past me into the bathroom. She started bending over to open the cabinet, and I hurriedly looked away. I mumbled random apologies under my breath. I couldn't help but look back; I could see most of her thighs, which were very pale and perfectly smooth, and I could see a clear outline of her round, soft-looking buttocks through the damp towel; my cock pressed out against my pants.
"Hey ... could you get this?" Kaitlyn pointed at a small bottle. "Uhuh ... sure," I muttered, and reached down for the object. I pulled it out and realized that it was a bottle of lubricant. "Kaitlyn, what do you need this for?" "I use it for my hair. It makes it, like ... shiny."
"Heh, strange. You know what this is, right?" I handed her the lube, but she didn't take it. Instead, what she did surprised me. She placed her hand on my arm and slowly looked up into my eyes. Her eyes were a deep aquamarine, and seemed to be slightly wet, perhaps from tears. I stiffened up, confused, my cock still bulging out from my jeans.
"I ... I've always wondered what you thought of me ... Do you think I'm pretty?" she asked, on the verge of tears.
I hesitated. My eyes moved down along her body, and she started loosening her towel. Her skin was very pale, and soft, with a sort of milky tone and a few freckles here and there. She was very slender, but didn't look too thin; she just looked like a young girl. One that was probably way too young for me. Her feet were bare, but still showed signs of nail polish; her toes were slightly curled.
"Of course I think you're pretty, Kaitlyn ... You're beautiful." I wrapped my hand around her child-like arm. She took a deep breath, loosening her towel even more ... then it abruptly dropped. There she was, standing in the bathroom, completely naked and dewy from her shower. Her waist was quite narrow, and her breasts were perky but supple. Her nipples were pink and slightly puffy. Her hair dripped down on her narrow shoulders, and we kept eye contact. I reached out with my other hand and rested it on her waist, and she put one of her arms around me and pressed her lips against my chest. She was only about 5 foot, so she couldn't reach any higher.
I pulled her closer to me until her breasts pressed against my stomach. She pushed me out of the bathroom and down the hall until I fell backwards onto the couch. I dropped the lube and sat up, while she sat on top of me. I started licking and massaging Kaitlyn's breasts, slightly dazed by her unexpected advances, but absolutely intent. My tongue moved further down along her soft, pale flesh until I reached her pussy. It wasn't completely shaven; she had some firebush there. It was soft and pleasant though, and my tongue ran up and down her entire crotch area, finally arriving at her perfect pussy.
Kaitlyn shuddered with pleasure as I ate her out, and my hands stroked her petite body up and down, my fingers caressed her breasts. My hands skated down her frame, and I grabbed her asscheeks, kissing her lips. The more I squeezed her, the deeper she'd thrust her tongue into my mouth.
I started pulling my jeans down. Once my pants were off, I felt a sudden burst of energy and picked her up, throwing her into the couch. She landed on her back; I took off my shirt, then mounted her. She yelped and struggled, but she was looking into my eyes and I could tell she wanted it. I stroked my cock, but it was already hard as rock. I pressed the head up to her clit and rubbed up and down, then slowly started pushing my dick into her vagina. She was extremely tight, and squirmed as I pushed in deeper. Then I felt a sudden rush of warmth and she squealed, grabbing me and shaking ... some blood came out, which told me I was her first, popping her cherry. I was a little worried, since I was about 8.5 inches, and as thick as a can of Red Bull. But my hormones outweighed my own worries and I drove my dick all the way in with a powerful thrust.
.... There is more of this story ...