So I moved to a new house with my family when I was about 6-7 years old. My parents and my sister and I. Me and my sis made friends with all the kids on the block, oh yeah and my sister was two years younger than me. Well, anyways, our best friends on this neighborhood was two kids down the street, a brother and sister named Zach and Ashley. Ashley was my sister's age, two years younger than me, and Zach was even younger, and he was kind of annoying. So me and my sis always hung out with Ashley. She was cool, and her and my sis were tight, like real best friends, BFF's or whatever.
So as we grew up with each other, we became close friends. I mean always over at each other's houses daily and playing whatever games, and running through sprinklers in the summer. As we got a little older, whenever my sister wasn't around Ashley and I would pick on each other. Well, that's not true, we always picked on each other, she actually left scratches lots of the time on me, she had crazy nails. I think Ashley liked me from the beginning. And well, she was starting to grow on me, she was the first girl I ever liked and when she wore her hair in ponytails it drove me crazy. Anyways, so when my sis wasn't around we'd push each other and she'd try to land against my crotch and I'd try to touch her ass anyway I could. We were older by this time, like just starting to find the opposite sex attractive, and well, I know girls develop earlier than guys and start humping pillows and masturbating sooner and thinking guys are hot, so that's must have been what she was into.
Anyways, we were spending the nights at each others houses by then, and I would sleep in Zach's room over at her house, which was right across the hall from hers, and when she'd spend the night, she would sleep in my sister's room, which was on the other wall next to my room. So one night she spent the night, however this is not the night in question just yet. But we were flirting and she ended up, just horsing around, standing in front of the doorway to my room, bending over, and pulling down her pajama bottoms and underwear and flashing me her nicely formed bare-naked ass. She stood there like that with her face turned away from me for at least 10 seconds. She wanted to make sure I got a good look. And I did, I couldn’t stop looking at that perfectly shaped ass. I mean, she was slender – the perfect body type, not at all a small petite girl, average height, and perfect straight brunette hair that went down to right below her shoulder blades and which she usually kept in a ponytail. She was taller than my sister but she was developing some nice curves around her waist and hips, which is probably why she had a nicely shaped rear-end. A total cutie. I must have looked like a fool, jaw open, just staring hard at her naked ass. So then she slipped her PJ’s back up her butt and quickly trotted back to my sister’s room next door. But not before I shot a quick remark: “I dare you to do that again.” Remember when it was all about dares? And how you wanted to do the dare so bad, even if someone dared you to drop your pants and underwear right in front of them? Well, she obviously heard me because she came back a minute later, and dropped her underwear down again and mooned me her sweet ass one more time. She waited a few seconds, then slipped them back up with her PJ bottoms and turned to go back to my sister’s room. I uttered, “Nice” before she trotted off. I’m not sure she heard. I wasn’t masturbating yet, so I didn’t know about jacking off, but I’m pretty sure I had some sweet dreams that night. Longer story short, my family ended up moving by the time I was 13, but just down the way like 7 blocks over. Her family stayed there in the same house, but the school system changed and my sister had to change elementary schools, while Ashley satyed in the same one, a street down from her house and our old one. We used to walk home all the time from school. Anyways, I was just starting middle school by then since I was 13 and my sister and Ashley went to different schools, so they didn’t see each other that much anymore. She came over one more time when her and my sister were both about 14. I never knew why she came over to our new house this one time, cuz right soon after my sister and her stopped being friends and haven’t spoken since. But she came over to stay the night, so needless to say I was excited. I think I was hoping to see her naked in my sister’s room getting dressed after the shower, I don’t know, my hormones were raging and I had the hots for her after all these years still. So anyways, she shows up sporting a ponytail which drove me nuts, and looking hotter than ever! She was developing some cute dimples, more curves and small, round titties. I couldn’t believe that she was here, after all those years of unresolved feelings. So anyways I caught her flirting with me and smiling at me a few times, actually acting nicer than she ever had towards me, and wearing some cute number that showed off her curves subtly. I know now that she was trying to catch my attention, but back then I was a dumb horndog and completely oblivious. So anyways, we all slept out in the downstairs living room den area that night, my parents had a room upstairs on the other end of the house, but mine and my sister’s rooms were just down the hall from the den, by a bathroom. So my sister and Ashley had a few blankets spread out on the floor and their own sleeping bags on top, sleeping next to each other, and I simply slept on the couch, since we all had stayed up talking that night until we fell asleep. Well I don’t know what got into me, but like I said, I was a horny teenager with raging hormones, but I slipped out of my covers in the middle of the night when everyone was asleep and went to go see if I could see that sweet naked ass of Ashley’s that I had remembered from those few years back. She was sleeping atop her sleeping bag, with a heavy duty cloth blanket and a sheet over her, sleeping on her stomach, head on her pillow. The broken VCR was pointed in her general direction, and was flashing 12:00 repeatedly, so I could see in the dark pretty good, but it was still dark. I was scared shitless thinking about her waking up, and my nerves wouldn’t settle. I got butterflies in my stomach. So I just sat there for a few moments trying to relax myself, and trying to maintain my composure. When I built up enough courage, I crawled up to her and took the blanket and sheet that she was draped in and drew it back over her backside. Her hair and her aroma smelled so good, I wanted to kiss her all over, especially on the lips. Which just told me that I really wanted her to be my girlfriend. So I continued to draw it back until her whole back and her butt and the tops of her legs were uncovered. She was wearing a cute little navel shirt that was small and tight with no sleeves, and little booty shorts that girls used to wear for PJs back in the 1990s, I’m not sure what those are called, and her hair was let down from her ponytail since she was sleeping. Anyways I could hear her breathing calmly and steadily, which assured me she wasn’t just pretending to be asleep, and I touched her butt with my hands on her shorts, and ran them across. So smooth, now I knew I wanted to see it again. I put my fingertips at the waistline to her booty shorts and slowly and gently pulled them down, to the tops of her legs. Very slowly. She was still asleep, good. So now I put my fingertips at the waistband of her underwear and gently and slowly pulled those down, too.
There was her naked ass, I was staring right at her nakedness again, for what had seemed like too long of a time. I had pulled enough of her clothing down to see underneath her ass, too. Nothing smelled any different until I leaned in to touch her ass and gently kiss it. I was a horny virgin, I had no idea what I was doing. But now I could smell a sweeter aroma, her pussy. After giving her sweet ass some gentle soft kisses, I checked to see if I had woken her – nope – and moved down lower between her legs. Not touching her, my nose went directly under her ass and in between her thighs, and I breathed in a huge whiff of what her pussy smelled like. It was pure heaven.
I had never done anything like this before, but feeling as brave as I was, I tried to kiss it, but her legs were too close together, so I stuck my tongue out and tasted just a little bit of the lowest part of her vagina. Mmm… As I lapped up what I had tasted, my dick was hard beneath my Adidas shorts, and I was touching it with my hand over them as tried to keep that sweet taste in my mouth for as long as I could keep tasting that sweet taste. I took my other hand and pointed my index finger outward and opened up her folded lip, to which to my surprise, made the smell much stronger. I kept it going, until it was partly in her pussy, and then suddenly it got trapped by a very tight hole, to which I very slowly and carefully pushed inside. The hole in her pussy could only wrap around my index finger, and I pushed it in about halfway and then brought it back out. I brought my finger up to my nose and smelled it, and it smelled like nothing I’d ever smelled before. I loved it, and I placed that finger in my mouth and licked it all up silently. Mmm… Then I moved the bottom of her pussy lips apart again, and I couldn’t really make out her inner lips as it was dark but I could just barely see her pussy. It looked light pink on the inside, and by this time my hand was in my shorts, moving up and down slowly on my raging circumcised hard-on. I then slowly inched my finger back inside her tight vagina as her lips folded back around it. I kept inching it in further, and she made no movement or squeal whatsoever. She just kept breathing loud like she was in deep sleep. This time my finger went inside her more easily, and it was a little slimy inside there now. I don’t know why that is but the only reason I can think of to this day was that she was somewhat awake when I did all this to her. Remember she really liked me from when we were little kids. So as I pushed it in, I slid it back out, then pushed it in slow, then brought it out of her slow. I was slowly fingerbanging her pussy and I was stroking my hard dick while I did it, all the while staring at her naked ass.
Now my finger was a lot more slimy from being inside her, so I brought it out and up to my nose and oh my god, the smell was 10 times as strong. Not knowing it, I pulled my big dick out of my shorts and continued stroking it slow. I lapped up Ashley’s sweet pussy smell and taste from my finger, until I couldn’t take it anymore, and then I looked down and realized that I was fully exposed, playing with myself right in front of her. Oh my god, my dick was SO HUGE. I looked at it, looked at Ashley’s turned face sleeping on her pillow, then looked at her naked bottom area, then looked back at my huge throbbing dick. The head was so big and round and shiny. And I was incredibly turned on by all this. To make matters worse, her small boob was pressed against the sleeping bag and blankets and moved to the side, pointing outward, and I could see her tit protruding from the corner of her sleeveless top by her arm. I jerked off a little faster, still very silently, and leaned over to grope her small pink nipple.
As I petted and touched her pepperoni-sized light pink nipple, it became hard all of a sudden. I could feel her tit perk up, and the nipple protruded outward, becoming erect to my touch. I squeezed it very lightly and gently. Wow, Ashley’s tittie. I cupped as much as was exposed in my palm, and it fit perfectly as I traced it with my hand, the hard nipple poking my palm. Very firm. I looked back at the back of her head again, she still hadn’t moved, then back to my raging boner, back at her naked ass and her exposed nipple. I immediately turned over on my back next to her (on the floor), and slid off my shorts and boxers. Now I was naked from the waist down, big hard dick hanging all out, and got back up on my knees again to look at her. I felt so taboo with both of us naked from the waist down, looking at the bottom of her pussy exposed beneath her ass cheeks and nipple which was shifting back into her shirt.
I scooted very close to her, and lifted one knee and leg up and placed it on the other side of her. Now I was spread out, over the top of her ass, on my knees. I put my finger down to her folds and felt inside a little and it was warm and still a little slimy. I figured screw it this is my only chance, and bent down some to place my big dick on her ass crack. Still asleep. I leaned back some, and now my 8 inch dick was just below her pussy. In the same spot I had place my index finger, I held onto my circumcised dick and pushed that up to her folds. It was warm. I pushed. My dick head went in through her folds. God, that felt good. I had no idea… I pushed a little farther and my dick head went through her lips and stopped at her hole. My big round dick head was all swallowed up by her pussy, but it wasn’t quite inside her yet. And she was still breathing the same, so I slowly thrust my butt down and in went my dick head slipping up her tight channel. I kept inching slowly and my dick went inside her, and I could feel her slimy walls around my shaft. It was SO TIGHT. It almost hurt at first, but then it started to feel better. I slowly pulled out some, then thrust my butt down again, a little faster this time, and my dick went inside her pussy with ease. I heard a slippery sound down there, and I didn’t know what it was but I liked it. I pulled out a little, and pushed my big dick back in her, and it went all the way in this time, and so much easier. Her pussy was getting so slimy, too. Not touching her with my legs or leaning on her at all, I started thrusting my butt up and down, at a slow, rhythmic pace and my huge hardened dick was pumping slowly in and out of her wet vagina really good. I could hear more slippery slurping sounds every time I thrusted outwards from her pussy, and it was making my dick bigger when I'd shove it back in, and my dick-head was pulsating inside Ashley. I could feel the cum rising in my dick and it was starting to throb as I steadily fucked it in and out of her tight vagina hole. Oh my god, this felt SOOO FUCKING GOOD! I had to literally hold my breath, because I didn't want to wake her or my sister up, who was sleeping on her stomach right next to us, from me groaning. My dick was the hardest it had ever gotten then, and so sensitive inside her very tight pussy. Inside her, her wet walls were gripping tight and clinging at my cock, and if I wasn't pumping it in and out of her so slowly, I would have liked to have given it to her rough, pull on her ponytail and smack her beautiful ass, tell her how beautiful she was and that I've always wanted to fuck her, and came so hard... But I had to stop a few times just for a couple seconds, because the cum was rising through my dick and before it got to my dick-head, I would wait, then once it went back down a little, I'd slowly pump her wet canal some more.
I was fucking Ashley Raelee Speece! This had been my dream for three years, since I had started masturbating basically, I mean she was my dream girl, and here I was fucking her pussy with my big raging dick in the middle of the night. I kept pumping her pussy, a little faster now, not too fast, but not real slow, and it glided inside her wetness pretty good. I wasn’t touching her at all, holding my breath, and dick slipping in and out of her. I mean if I didn’t stop I was gonna cum inside her real soon. I silently muttered her name, “Ashley…” as I gave it to her fast a few more times. The slippery sound was so hot, and as I brought my hand down to pull my dick out slowly, I heard a little quief sound from her hole as my head came out and lots of that slippery sound as her lips and folds closed back up. I brought my leg back over and now I was on the side of her again on my knees, and my dick was all wet. I was still very hard, and I went to pull her underwear back on her. As I did, I leaned over and smelled her vagina one last time. Wow, the stench of her pussy was so strong and overwhelming, after sticking my dick in there and due to it being more wet. I sat back up and pulled her underwear on her slowly. Then I gently lifted her pelvis as I pulled her booty shorts up. I finished by putting the sheet and blanket back over her, covering her back up.
As I grabbed my shorts and boxers and silently snuck up and out of that side of the den towards the couch, I sensed her shift or move just a little. As I covered up on the couch and put my boxer shorts and Adidas underneath my pillow, I saw her turn her head where she was sleeping and then a minute later she rolled over onto her back. Whether she was just doing this in the middle of sleep, or because she was awake and pretended to be asleep the entire time I was gently fucking her, I don’t know for sure. Whatever the case, I didn’t think about it too much, because I proceeded to jack off right there underneath my covers just 10 feet away, as I had stopped before I had cum while I was fucking her, because I didn't want to get her pregnant, and I didn't want to pull it out and squirt my warm gooey liquids all over her ass cheeks (there would have been a whole lot of it, she really turned me on! As I was in lust with her). There I was, big dick and all, stroking hard while I still faintly tasted her pussy in my mouth, and at one point threw the covers off while I stroked, trying to be quiet about it. I had my eyes closed the whole time, and if she were awake through all this, she would have definitely looked above her pillow and seen what my dick looked like, as she had never seen me naked before, and she would have known how big it was from feeling the length of it being inside her just minutes ago.
I lost my virginity that night, and I'm pretty sure she did too, there was no blood although it hurt going in, so her hymen was already broken I know tampons can do that or if she was already sticking things up there that can explain how my big dick fit so easily even though she was so tight being a virgin, plus she was pretty wet after I slipped it inside her, making me think she might have been awake, and just pretending to sleep, enjoying me fucking her and feeling my cock inside her, I think that's what she wanted was to see my dick and for us to fuck. Also I'm not sure if a girl can get wet if she's sleeping... Can someone tell me if that is true or not?
The next morning she took a long time in the shower, I figured she must be playing with herself after last nights events, that is if she had been awake during them. While she was doing this I snuck into my sister's bedroom downstairs where Ashley's backpack was while my sister watched TV upstairs. I went through her bag and found her underclothes that she had wore the day before. I inspected her bra to see what size cup she wore so I would know her tittie size, a B cup, and then found her underwear. I took the crotch area and proceeded to sniff and smell my way back to heaven as my dick became hard again. I took it out and jacked off while I smelled the scent of her pussy aroma, and my dick stood straight out a full 9 inches. While I played through the night's events in my head, I remembered what it felt like being inside of Ashley, her soggy vagina clenching my big dick tight, and suddenly my cum was rising. I kept thinking about it more, how her nipple was sticking out just enough for me to see it and then after I stopped fondling her breast, her nip went a little soft which made it shift back into her shirt. I remembered watching her fine smooth ass while I pushed and pumped my manhood into her, forcing her to take my hard cock, knowing how she secretly wanted it from years before. I remembered her pussy hole making that squishy sound every time I fucked my dick inside her, and suddenly I was climaxing. After smelling her pussy from her underwear crotch area one last final time, I held them below my dick and slapped my dick-head really fast and hard. My cum shot spurting out, all over the crotch of her underwear, and as I pulled it, I let the rest of my white sticky load gush and guzzle and drip onto her briefs. I put my pants back up. Her underwear soaked with my cum in the crotch area, I folded them back up and placed them back into her bag and zipped it back up. Ashley was finishing up her shower, which meant she would be down there any minute.
She conversated with us some more and then left after breakfast and her and my sister never spoke again, due to some falling out in middle school. During the breakfast conversations, she aggressively asked me sister this: "Did you keep pulling my shorts and panties down last night?" ...???!?!?! I was shocked. Of course, I was on the other side of the upstairs kitchen in the family room watching TV, but still Ashley made sure it was in earshot and that I had heard her. What a little minx. She had enjoyed last night, and now suddenly everything made sense. She never came back over, but I saw her years later at the college, she was still cute and very hot, with the same perfectly shaped ass. It’s too bad, really. Had my family stayed on the block, she would have been my girlfriend.