This is my first story, so be nice. The people are real, the situation is real, but the names are different and this is how I dreamed of it happening
Ok, first let me start off with a little background information. My name is Chris and this story takes place in the summer between my senior year in high school and my freshman year in college. I was 17 at the time. I have a sister, Jill, who is 3 years younger than I am, which makes her 14 at this time. Her best friend since kindergarden, Allison, or Allie as we all call her, is also 14 at this time. Jill and I do not get along at all. We might as well be from different planets. We are always butting heads and are always getting on each other’s nerves. I could not wait until the day I moved away to college, 1000 miles away to college… Things didn’t always used to be that way though. Back when we were younger, say elementary school aged, we got along just fine. We often rough housed with each other, slept in the same bed together (we called them our little sleepovers, even though it was just that, sleeping, nothing sexual at all), and even bathed together. That all changed as soon as she hit puberty around 10 years old. At that time, I was in puberty full force and couldn’t help but noticing my kid sister deveolping into a woman. I knew it was wrong to fantasize about her, but I did anyway, and she knew it. She would always flash me her cute little panties, clinging to that sweet petite butt of hers, and during the summer when we went swimming in our pool , she would often let her bikini ride up into her butt crack and flaunt it around me, and she even flashed me her cute little AA titties every once in a while. That all changed when she turned 12 and starting having her period. No more showing off and I was getting sick of not having any new images to jack off to. I knew it was wrong, she being my sister and all, but I didn’t care. I figured as long as our parents never found out, it would all be good.
Anyway, enough useless information… onto the story.
It all started a couple days before my grad party. Allison was spending the weekend here with Jill (as they often did) which kept Jill out of my hair so I had no complaints about all of the extra noise. Allie is a very interesting person. I’ve always had a little crush on her, but I could never act on it because of the 3 year age difference. She’s just the cutest person in the world. Long, breast-length blonde hair, sky-blue eyes, her face covered in freckles, and a rack and a tight bum that made you know she was a woman and not just a cute little kid. She’s normally a very bubbly and happy person, but this week was different. She had just gone through a nasty breakup with her boyfriend, and wasn’t talking much about it. She would occasionally lock herself up in my sister’s room and I’d find out that she would just be lying there on the bed crying for an hour or more.
Now before I go any further, I should probably give some information about myself. I’m 6 feet 2 inches tall, and weigh anbout 210 pounds. I’m by no means fat, but I could afford to drop a few pounds. But I’m built pretty well and I have a lot of muscle, but it’s not toned very well. I have been told by numerous, unbiased people, that I am a very attractive person, but I don’t think so. You see, I’ve had self-esteem issues since middle school. I had (and sometimes still get) very bad acne and even though my wide football-player build gives the impression of a well-toned body, it’s not. I don’t play any sports and I spend my free time either playing computer games or trying to pick up extra hours at work. I’ve only had one girlfriend, and that only lasted 3 weeks before we broke up and we didn’t get any further than kissing. Obviously, I’m still a virgin (at this point in the story, anyway) at 17 years old and with the way my life was going, I was not going to get laid anytime soon.
Well, the day before my grad party, that all changed. Jill and Allie had decided to go for a bikeride that lovely Friday morning around 11:00, or so that’s what I was told in my sister’s text message (I was working 6am to 1:30pm that day). I wasn’t really hot out, but it was just enough that you had to have the AC on in the house. When I got home from work, they were still gone, and I figured they’d return soon. I started the long, labor-intensive task of cleaning my room to help make the house look presentable for my grad party the next day. About a half hour later, the door opens they both walk in, drenched with sweat , panting hard, and just looking exhausted. They told me they were going to take a shower. As teenage girls usually do, they boareded themselves up in the bathroom and remained in there for what seemed to be an eternity. When I heard the water running, I figured one of them was in the shower and the other was just waiting there for “moral support.” A little while later I heard the water turn off and a door open, but I didn’t know that Allie had left the bathroom and gone into my sister’s room to get dressed. While I was putting away the laundry that had just been piling up on the end of my bed over the last week, I came across one of Jill’s socks folded into one of my shirts. I headed to her room to return it, and the door wasn’t open, but it wasn’t closed either. There was about 2 inches open, so I opened it up all the way thinking nothing of it.
And there in front of me stood Allie, dripping wet and completely naked. For a short few seconds (but what seemed like an eternity at the time) neither one of us said anything. Here was Allie, someone I’ve known for 12 years and have always had a little crush on, completely in her perfect form. I couldn’t help but let out an audible sigh as I admired her contours, her shapely legs, her perfectly round 34B breasts with light pink nipples, her flat stomach that led down to her carefullly trimmed snatch, and her wet wavy hair to top it all off.
Allie and I have always had an interesting relationship, we always joked around with each other and it was fairly obvious that she had a little crush on me, but we both knew we could never be together. Our age difference and my sister would bring way too many complications to a relationship, so we both just brushed it off as nothing. Her relationships would come and go, but no matter what she would always find time for me. And now here I was, seeing her naked at her most vulnerable moment, I couldn’t help but feel sorry for her.
Before I could say anything, Allie quickly grabbed her towel and wrapped herself up in it, sat down on the bed, and starting sobbing softly.
“Allie, I’m so sorry I barged in like that. I didn’t know anyone was in here, I’m really sorry Allie!” I said as I sat down next to her in an attempt to comfort her. She didn’t say anything, she just kept crying. “Allie? Allie?” I repeated, “C’mon, I didn’t mean to scare you like that. I would never wanna do anything to hurt you.”
“You could have at least knocked before you came in,” she sniped back at me.
“Oh Allie, I’m so sorry, please stop crying, please,” I begged as I tried to giver her a hug. She initailly winced a little bit, but then she let me hug her. “Everything’ll be fine,” I reassured her.
She sniffled a little bit, turned around, and looked me in the eye. The look wasn’t of disdain or hurt, it was of trust, trust that I had built up with her over the years. We just sat there, looking into each other’s eyes, and then the feelings hit. It was like a spark. I slowly moved in, closer to her face, and seeing that she wasn’t backing away, moved in for the kiss. It was just a light peck on the lips at first, then it gradually started to become more intense. She opened her mouth, and I opened mine, and our tounges began to dance with each other, exploring each other. About a minute later, she broke the kiss and shifted back a little bit. Her faced turned a deep red color as she looked away from me.
“You know we shouldn’t have done that,” she said horsely while trying to catch her breath. “I’m too young for you, and what if Jill finds out?”
“Allie,” I said as I began to lay my heart out on the line, “I’ve always liked you and I’ve always thought you were the prettiest girl in the world. I don’t care if you’re 3 years younger than I am or that you’re my sister’s best friend, I need you.”
Allie just sat there and didn’t say a word. About 15 seconds went by before I got up. I apologized to her and began heading towards the door.
“Wait, don’t leave,” Allie piped at me, “Ever since I saw you I’ve thought you were a really cute and sweet guy. That’s why I like hanging out here rather than my house, because I get to see you. I know we can’t be together, but who has to know about right now?”
I walked over and sat back down on the bed next to Allie and we resumed our embrace. As our kiss grew more passionate, I could feel her hand running up my leg to the ever-growing bulge in my pants. She started to rub the outside of my shorts as she began to moan. Taking that cue, I placed my hand on her shoulder, and started to rub down her arm, over her hand, and onto her stomach, and by doing so releasing the towel covering her to fall to the floor. Allie giggled.
“You know, I’m sitting here completely naked and you’re still fully clothed,” Allie said as she began to take my shirt off. “I don’t think that’s fair.” I chuckled and lifted my arms to let her remove my shirt more easily. “We’re not quite there yet,” she quipped as she motioned to my pants, and the rather large bulge in the center of them. Without giving me a chance to object, she grabbed my shorts and boxers at the same time and started to wiggle them off. I lifted myself up from the bed to make it easier for her, but she stopped as soon as she got my pants down far enough to where my erection sprang up, all 7 inches in their glory. “Wow! That’s so big!”
“That’s what she said,” I stammered, thinking of something else to follow that up with.
“You’re so cute and funny,” Allie giggled as she threw my pants to the floor and began kissing me again. Pretty soon, we began to let our hands wander again. Mine found its way to her breasts, squezzing them and fondling them, and hers found their way to my aching member. As she began to stroke me slowly and gently, I picked her up, and laid her down on the bed and crawled ontop of her. I planted another passionate kiss on her soft, tender lips, while I massaged her breasts. All the while, my throbbing cock was aching for relief. I could feel it rubbing up against the inside of her thighs and feeling her wetness. I don’t know why, but I wasn’t feeling selfish at all. I wanted to please her before I tended to my own needs. I broke our kiss and gradually moved down to her chin and neck, continuing to her chest. My tounge swirled around her left nipple, while my hand had attention on her right. Then I switched. All I could hear was the sound of licking and sucking coming from my mouth, and the soft moans and coos coming from Allie’s. I knew she was enjoying this and I wanted to give her more. I moved down away from her breast, past her stomach, and then reached her inner thighs. She was very wet and the smell of her sex was the most intoxicating smell I can ever remember. Even though this was my first time eating a girl out, and doing anything sexual for that matter, I had learned what to do through internet help files, sex stories, and the like. I gently began to rub the outside of her sweet little pussy while I licked around her thighs, moving toward the center once in a while to tease her clit. Her moans were getting fiercer and more pronounced, and I took that as my cue to get on with it. I moved toward the entrance of her love tunnel and started to lick her pussy lips, teasing her ever more. I searched for her elusive clit and I knew I found it when she let out a loud grunt and folded her legs behind my head, trapping me. I worked fiercly on her little clit as Allie began gyrating and thrashing on the bed out of control. Then without warning she grabbed the back of my head and forced my face into her crotch. With a loud, high pitched moan, she came, and flooded my mouth with her sweet, supple juices. I’ll never forget how good they tasted. As she lay there panting and out of breath, I moved back up to her and began kissing her again, letting her taste her own juices while she laid there almost helpless. Then Allie broke the kiss with 5 simple words.
“I want you inside me,” she said, still trying to catch her breath, “I want you to fuck me now!”
“But,” I stammered, “You’re only 14, and…”
“Screw that! I need you inside me right now, Chris! Please fuck me!” she interrupted me.
I got up on my knees and positioned my throbbing cock at the entrance of her steamy love hole. I gently guided it into her. The feeling was simply incredible. Her hot, tight, twat was like a vice grabbing hold of my member sending intense pleasure rushing through my body. I gradually went deeper and deeper until I hit her hymen. The look in Allie’s eyes told me to proceed and so I grabbed her and forced my way through her virginity and into the deep recesses of her womanhood. She began to cry from the pain of me breaking through her hymen and I gradually pulled out leaving just an inch inside her while I kissed away each tear running down from her eyes. We just laid there in our embrace for a few moments before Allie motioned me to proceed. I started out slow and gradually picked up the pace as she began to meet my thrusts with hers.
“Ugh, ohhh, ahhh, ugg, don’t stop. This feels so good,” panted Allie, “Fuck me harder, faster!”
I knew I wasn’t going to last long at all, and judging from the far off, euphoric look in Allie’s eyes, she wouldn’t last much longer either. I picked up the pace and soon enough, I was nearing my climax.
“Allie, I’m gonna cum,” I managed to say as I fucked her harder.
“Don’t pull out! I want you to cum inside me! Don’t you dare pull out!” she responded between breaths.
At that point we were both in such a far off euphoric state that neither one of us cared about what would happen if I finished inside her. As I was nearing my climax, I felt the walls of her vagina tighten up and grip my cock like nothing else, and she crossed her legs behind my butt keeping me inside her. She began to orgasm and the feeling of her juices running over my cock and the tightness of her little twat was more than I could handle. I met her orgasm with mine as I shot thick load after load of cum up into her love tunnel. That climax topped any I had previously had with masturbation 100 fold. Once her sweet devirginized little pussy had stopped milking my cock of all its worth, I collapsed ontop of Allie, both of us completely out of breath. When we eventually regained our composure and just gazed into each other’s eyes.
“I love you Chris,” she said.
“I love you too Allie,” I replied.
I rolled off of her and we were both on our sides facing each other when we began kissing again, more passionately than ever.
“Do you think we could ever do this again?” Allie asked.
“I’ll make sure we do,” I answered.
We remained in our embrace of love and in a state of bliss until we heard a knock on the doorway. We both jumped up and our stomachs sank when we saw Jill standing in the doorway.