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Introduction:

This is a fictional story about two 16 year old friends and their adventurous time together one night. This is a bit long, but if you can stick with it, I am sure you will enjoy the story. Please comment as this is my first story and want to know what I can improve.
Hi, my name is David. I am 16 years old and live in a relatively small town in New England. My life has been rather uneventful the last few years, particularly while in high school. It seems as though everyone around me is out having fun on the weekends, while I stay in my room playing video games and hoping that one day I may be with the girl I love.
She is perfect. Amber is the most stunningly beautiful girl I have ever laid eyes on. Her beauty is not conventional…and I can’t help but feel like that is part of the attraction. She wears the most interesting clothing. The garments are almost like dresses, but very casual and full of bold colors like magenta, evergreen, and blood red. Now, the story of how I got to know her is a long one so I will spare you the gritty details.
All you really need to know is that she lives next door to me, and has as long as I can remember. We have been friends ever since grade school, which is where we really started to notice the others existence…but you know how it is as a young kid. We have been playing outside together, going to movies together, basically doing everything together since we were both around 6.
Now, obviously for most of my life she was just my friend, but something had started coming over me a few years ago. I started noticing her beauty. Realizing that she was no longer a girl but developing into a fine young woman.
Okay so now to the story I have been wanting to tell. A little less than a year ago, when we had both just turned 16 (our birthdays are a month apart, mine in October, hers in November), we hung out over at her house like we often did. I could not help but notice that the vibe in her room was a little obscure and abstract from the normal good feelings I get when I enter. I am not so sure how to describe it, but I definitely noticed something peculiar.
After a while of talking about friends from school, teachers that bored us, school sports that meant nothing to us, and the general lackadaisical conversation that pretty much occurred every day…Amber asked something. “Hey David…have you ever had an actual girlfriend?” I did not think much of it and quickly replied: “No. Why?” “No reason” she said sort of quivering after she said that. “Oh come on, there has to be a reason you said that. We never talk about shit like this.” After pausing a bit, seemingly reluctant to say anything, she mentions “Well it is just that…well…er…just forget it lets talk about something else.” I accepted that she was not feeling correctly about something and dropped the conversation for another day.
As far as I know, neither of us has had sex yet. Neither of us has experimented either. Though I can not know this for sure, as for some reason there has always been a barrier between us about those sorts of things. Fortunately that changed the next day.
I called up Amber the next morning and told her that we never really properly celebrated her birthday. She acknowledged, and asked what I wanted to do. I said just to come over my house tonight, ask her parents to stay the night here (which had not happened since we were little kids) and we would throw her a little party. She told me that her parents had left town for the weekend and that she was going to be home alone and figured that there was no point in calling and asking. So, she showed up a few hours later and we had pizzas with my parents and a little cake. After all of this was done, we went down to the basement (which was refinished into my game room, where I spent most of my time when not in my room) to talk.
At this point, it was probably around 7pm. I suggested playing some board games and some video games to pass the time. So, by the time we had run out of things to play it was around 11 that night. As I folded out the futon bed I recall her asking me something very personal: “Hey David….um…have you ever been with a girl. You know like intimately?” Shocked at her question I hesitated a bit and then said “No, have you ever been with a guy before?” “No, I was just wondering.” That was a relief, I did not want my precious flower to have been soiled by some jerk at school.
After a while of trying to decide what we wanted to do for the rest of the night (movies, games, etc. were all mentioned), I had a sinister idea to perhaps be her first. I mentioned that maybe we should make up a game. She was all ears and grabbed a piece of paper to write down the score and perhaps some rules. “Okay” I said, “Basically this is a game of bravery. You score one point for every easy challenge and 2 points for a difficult challenge. Now, once you choose to hear the challenge from the other person, you must act on whatever they challenge you with. You can choose not to hear the challenge, but you lose one point of you do. The first to 10 points wins. Sound fair?” “Sure, this sounds like fun!”
So, trying not to blow my cover, I offer to challenge her first (with something simple to ease into things). She accepts, and waits to hear my challenge. “Here is your task worth one point: Stand on your head.” She thinks nothing of it and stands on here head with ease, which prompted her dress-like clothing to fall to the floor a bit, exposing her bare legs. On her turn she says “For a 2 point challenge: kiss me.” Uh….WHAT! No kidding. She actually wants me to kiss her. This may be easier than I thought. As I lean forward I can see her lips quivering a bit. Once I make contact, we sweetly kiss for about 10 seconds and she pulls away. Wow. Just wow.
Not wanting to beat around the bush now…I say: “Um, Amber. Why did you ask me to kiss you?” “Simple, I think I love you David. I think I always have. We are meant to be together, and if you really want to know what I want for my birthday it is to be with you…but I can’t.” Crap. “Why not?” I asked, hoping there is some simple fix to things. “Well, I am just not ready to be with a guy yet.” This was devastating. I called off the game and told her it was alright (which was a lie) and just to get ready for bed. She went into the bathroom down in the basement to change and I went upstairs to do the same.
She sat down on the couch and as I came back down, I could not help but notice how cute she looked. At 5’5” she was not exactly short, but not nearly as tall as I was at 5’10”. She had her reddish brown hair down from the pony tail it was in before. The natural waves of her hair were enticing. She was wearing a pink and red pajama top, which showed off her enigmatic, B cup sized breasts. Her pajama pants matched the top and were equally as cute, only reaching the top of her ankles. She was going to sleep on the futon and I was going to sleep on an inflatable bed which was right next to her…only I had a plan.
If I could remember correctly, from the many times we used to have sleepovers, she was a notoriously heavy sleeper. I swear I used to jump up and down on her bed at home and she would hardly flinch. I remember her parents had to come in and shake her rather violently to get her up in time for school one morning. So I was going to use this to my advantage. We both said goodnight, I turned out the lights (which when done in a basement becomes very dark, very quickly), and slowly walked over to my bed. It was not more than 15 minutes later that I could tell she was asleep. I called out her name a few times in increasingly louder tones until I knew she was sound asleep.
This is where the fun would begin. I slowly got up off of my bed and made my way over to her. I could not see very much, so I turned on a side lamp used for camping over by my bed. This light reached just far enough to light her up ever so slightly, but not enough to wake her. I did not know where to begin. Scoping out her body I had so many desires, but I had to be strategic, as to not wake her up. Sure she was a sound sleeper, but there has got to be a limit. Looking at her face, I longed to kiss her again. I knew it would not be the same as before because not getting kissed back is just lame. This brought me to her chest.
Oh how long I had awaited this moment. As my hand went out to grab the bottom of her shirt, my heart was pounding a mile a minute, my hands were shaking so badly I hardly had control. But I was on a mission. Reaching out I finally grabbed hold of the shirt…and slowly lifted it, barely an inch at a time until it reached the very bottom of her breasts. I could not yet see anything, but my penis was standing at complete attention, all 5” of it. Creeping over her breasts I started to see the most beautiful thing I had ever laid eyes on. Her breasts were perfect. Supple, soft in color, and her nipples were formed perfectly. Not too big, but slightly puffy. After a long while, I had completely taken her shirt away from the parts that mattered and contemplated my next move. I wanted to touch them.
I moved my hand down from the pajamas and toward her bosom. I got a good feel all around them, encompassing every inch of her supple, soft flesh. This was a feeling I would never forget. I leaned down and was now almost on top of her, so I shifted over to one of the unused areas of the sofa bed. I moved my head over to her left breast, and started licking it ever so softly. The taste was incredible, I just could not get enough, I soon started sucking and sucking I just could not pull myself away. This was the best night of my life. She tossed a little bit ,which initially scared me a bit, but I stood back up and figured I would have a look down there. I was steadily becoming more confident and less nervous, so I moved my hands toward her pants and moved them down until they were at her knees. Looking straight into her genital area, I examined her vagina. It was shaven, which was a bit of a surprise to me, as she was most likely still a virgin and was not dating anyone.
Knowing that I wanted to have a feel, I completely took off her pajama bottoms and spread her legs a little bit. I got down on the floor, removed my pants, and started playing with myself a little before I look a lick. My dick was throbbing. It was not that big, I say 5” just to be nice, it is probably a bit smaller, and is uncut. I moved the foreskin back and forth over my head a little bit which gave me great joy, and then plummeted into her pussy with my tongue. Feeling around and tasting the sweetness of it, I could tell she was getting aroused. Liquid was starting to flow down towards my tongue, and I fastened my pace in both my licking and my masturbation. Before long I was feeling like I was going to cum, so I stopped both actions and got back up.
I did not know if I wanted to insert it or not. Well, I really, really wanted to, but I felt that would be the wrong thing to do. But, alas, I went to do it anyway. Slowly my cock inched closer to her pussy, I peeled back the foreskin and let it enter. As if at that very second, I could see her eyes open a little, as I was fixated on those amazing breasts of hers. She seemed to not mind, so I started pumping. She moaned a bit as I broke her hymen, which prompted a bit of relaxation on my part knowing she was a virgin. This cave of wonder was impossibly tight. It was almost like there was a bit of suction pulling me into her deeper and deeper. The feeling was sensational, like a wave of pleasure washing over my body. She started to moan again slightly, still only half awake, enjoying the time we were having. Seeing her breasts shake in constant motion with my thrusts got me really excited. I was about ready to cum when she shouted to stop. I was confused, as I thought she was really enjoying herself. Turns out she was.
As I stood there, dick pointed out after being happier than ever before, she told me to come lay by her. She soon got on her knees and focused in on my dick. Before I knew it my dick was in her hand and she was pumping away. Watching my foreskin go up and down enveloping my head and then back down again was mesmerizing. Looking at her content face and staring out at her breasts I reach for them for a feel. Now, her face lowers and she starts licking my cock. I am not so sure I can take much more. She pulls the skin back over it and inserts her tongue in between and starts circling around the head. This was sensational. She slowly starts bobbing her head up and down and I am cringing in excitement trying not to explode. I soon let out a slight groan and tell her I am going to cum soon, so she stops and gets on her back. She instructs me to grab her tits, place my cock in , and pump away. After getting in there for a few seconds, feeling this astounding feeling once again, and touching her mounds of glory with both my hands and my dick, I look down. I see myself inserting and coming out over and over again. I see her face yearning to feel the end. As I feel I am ready to cum, a tingling first starts at my feet. It quickly races throughout my body. up my legs, into my arms, around my waist, and finally into my penis. I then shoot out continuous streams of cum all over her tits and mouth and she is overjoyed.
After all is said and done, no words are spoken. I climb back into bed, she puts her clothes back on and says but one thing: “David, I am not mad. I was awake that entire time. I love you.” I went to bed and the night was through. Thus ended the best night of my life.
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