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 13, 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 eachother 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…”
“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.
“Ooohhhahhhhh!!!” she cried. Her fingertips ran down my waist, and she clenched her teeth.
“Fuck yes, Kaitlyn! You little slut!” I bobbed my dick in and out, feeling up against her pussy walls; I wasn’t all the way in, but I couldn’t go any further. So I pulled my dick almost all the way out up to the head, and then thrust it back in, bouncing off the walls, then again, and again. I was thrusting so hard her entire body slid up and down the couch. I lifted one of her legs up and dug in even deeper. Kaitlyn struggled with her fingers to try to guide and control me, but my primal instincts ignored her.
“Uh! Uh! Uh! Ohh!” she cried out.
Sweat ran down her sides and slid up against me. The faster I went, the more we sweat. Her crotch area was unbelievably wet, and with a final intense thrust, I came. She whimpered and I pounded her even more until her pussy started creaming. I kissed her chest and she tenderly moaned.
“Uhhh…” said Kaitlyn. “Wow...you’re big.”
I grinned and collapsed on the couch next to her, and she rolled onto her side.
“Let’s go to my room,” said Kaitlyn. “We’re right in the living room.”
I eagerly stood, grabbed the lube and my jeans, picked her up, and then climbed the stairs with her limp, exhausted body in my arms. I could tell which room was hers from the decorations, and I went in, locking the door and dumping Kaitlyn onto her bed. She lay there, rubbing her pussy. My mind was in a state of frenzy; I was still very horny, and my dick was sticking straight out.
“Hey…” I started tentatively. “I’m just wondering…” She looked at me.
“Have you ever done anal?” I asked, without thinking, still in the heat of passion.
“Uhh…I’ve tried it, actually, with, you know…Sharpies,” she responded. I felt a rush of enthusiasm.
“Would you ever do it with me?”
“Well, why don’t you try it and see?” she responded coyly.
I jumped onto the bed, grinning. She lay on her side, still rubbing her pussy. I grabbed the lube from off the floor and started rubbing her silky, hairless thighs with it. She bit her lip and propped herself up on her elbows and knees, arching her ass up, wagging her hips playfully. I squirted lube onto her asscheeks and massaged them with my palms, slapping them gently until they were slightly red. Then I bent down and started licking her tight, pink asshole. Her sphincter muscles tightened and she rubbed her pussy even more.
I lubed up my fingers, and stuck one of my digits halfway in. She tilted forward, arching her ass up even higher and moaning softly. My finger slid even deeper, and I inserted a second finger, her asshole squeezing my fingers together. Realizing that she might be too tight for me, I lubed up a finger on my other hand and stuck it in as well, and began prying in opposite directions to try to loosen her up. Her toes curled and her feet rubbed up against my legs. I could tell she was enjoying getting her asshole worked open. Her sphincter muscles slackened enough for me to slide another 2 fingers in, totaling 5 fingers, which doesn’t sound like a lot, but her asshole was so tight it felt like bending steel.
After a few minutes of massaging the inside of her ass with my fingers, I propped my dick up against her and starting lubing it up. I squirted a bit more lube on her asshole.
“You ready, baby?” I asked.
She responded by angling her ass toward me and quickly rubbing it with her fingers, sliding her middle finger in, and then licking it off. I grabbed her wrist and pressed the head of my cock against her anus. Then I started applying forward pressure to her hole; the head slowly pierced the opening. Kaitlyn lurched forward suddenly and cried out, ejecting my dick and squeezing herself shut. I tried to shove my cock in again, but she wouldn’t budge.
“Kaitlyn, you have to relax. It will feel good once I’m all the way in,” I reassured her.
“Unngh…It still hurts!” She was biting her lip.
“Once the pain goes away, it’ll be easier,” I said. She nodded slowly, then spat on her fingers and rubbed my dick.
“Okay…I’m ready,” she said hesitantly, taking a deep breath.
My cock was harder than ever now, so I didn’t wait a moment. Squirting some more lube on her asshole, I pressed up to it again. Now my head could slide all the way in. She held her breath, clearly in pain, so I let my head stay inside her for a minute. Then I started pushing the rest in. I could feel the muscles tremor, then release as she let out cries of bliss. My dick eased through the first sphincter, which squeezed tight around me. I pushed more and more into her ass as it opened up, until I hit her second sphincter. Instead of trying to go even deeper, I started pushing in and out just to try and work her out even more. Kaitlyn groaned as she started taking longer strokes, and her colon began to protest, so I pulled my cock halfway out and spat on her ass, then tried sliding in again. Now my cock slid in easily, and as I thrust harder, she rocked her hips back and forth in a seesaw motion. Her ass felt slicker with every stroke, and her groans of discomfort were replaced by screams of enjoyment.
Once her rectum was sufficiently open, I clutched her asscheeks and made her stop moving. I wanted to see just how deep she’d let me go. I pulled my dick all the way out of her ass, and it made a slurping noise, opening up to reveal a beautiful gape. She constricted her ass a few times, but the gape remained. I squirted a little lube into her gaping ass with a primal feeling of accomplishment for stretching her out so much. Kaitlyn felt her dilated anus using her fingers, then forced the air out and squeezed shut.
“Mmm…” she moaned.
“Don’t get too comfortable yet. We haven’t even gotten to the hard part!”
I gave my cock a brief preliminary rub, and then put it back into her asshole, causing Kaitlyn to pitch forward. About 6 inches glided in easily, but I still had at least two inches to go. With my dick still in her ass, I pulled Kaitlyn’s legs out from under her and laid her on her side. Then I grabbed her buttocks, and starting pulling her toward cock. Her second sphincter was extremely tight, and had clearly never been penetrated before, so I took it slow. I went an inch deeper, and my cock pressed hard against the sphincter. I finally felt it give way, letting my cock plunge all the way in.
My balls slapped up against her satiny buttcheeks as all 8.5” penetrated her colon. She cried out, grasping my hand, her tiny frame seizing. I tugged my dick a couple inches back, and then went balls deep again. I could feel her ass juices flowing around me, and I started slamming her violently, giving deep strokes. She looked back up at me and down at her ass again with an expression of delight and disbelief. Without pulling out, I rolled her onto her tummy.
“Spread your buttcheeks,” I told her. She pulled her cheeks apart, and I pivoted my cock to get an even better angle. For the next 5 minutes, I plundered her ass as fast, hard, and deep as I could, rebounding off of her spongy insides. Her face was getting flushed, and she stopped making noise but for the occasional grunt and moan. Realizing that at this point I might be the only one getting pleasure, I moved her hand out of the way and rubbed her pussy. She was wetter than ever, and she began making more noise, until I finally felt her body spasm and writhe in pleasure. She jerked around much more vigorously than I thought a 90 pound girl capable. I thrusted one final time, and then lay down on top of her, leaving my cock inside. We both breathed sighs of relief.
“Your ass is amazing…” I said. I still couldn’t believe I was fucking my friend’s sister’s ass. It was even harder to believe that she was only 13, given the punishment she’d just taken.
“That felt…good,” she said as her chest pushed in and out.
“You’re a newfound anal whore, aren’t you? I’ve gotta cum. Get up!” I insisted.
Kaitlyn promptly got on her knees and put her hands behind her back. I grabbed a tuft of her red hair and started jacking off. She probably didn’t know what was coming, as she didn’t shut her eyes, but when I squirted my load on her face, she flinched suddenly and twisted away. When she turned back, I saw cum dripping from her eyes, and her lip quivered. I let go of Kaitlyn’s hair and she collapsed onto her bed, staring up at the ceiling, her face covered in tears and ejaculate. Then she looked at me.