Aileen’s Sleepover (m/g, oral, anal, 1st, ws)

Aileen’s Sleepover (m/g, oral, anal, 1st, ws)

Prologue: a little girl tells you about her first time with her teenage crush. Disclaimer: Based on fantasy

Author: OxyGreen

I’ll tell you my story but you have to promise not to tell. Its about how I had sex for the first time this year, and it was great…but weird.

My name is Aileen and I’m 9 years old. When my story happened, I lived in Connecticut – we just moved. My house was in a town near a beach that isn’t a very good one because there are too many big rocks that hurt your feet when you try to play there. My house is – was – at the top of a little hill. In the distance, from my window, you could see a big tower on Long Island with red blinking lights. BUT!

This story doesn’t take place at my house, it takes place at my friend Leah’s. Leah is my best friend in the whole world. Leah and I have been friends since we were six. We used to play magic dolphins, where we would pretend we were dolphins saving the ocean from pollution. We invented that game the first week we were friends because Wallie the Whale Man came to school to teach us about the whales (he talked about dolphins, too), and how the oceans are in trouble.

We’d go into some bushes outside my house to play magic dolphins, and one time when no one was looking we both watched each other pee. I think that was the day we officially became best friends. You probably think I’m gross. Do you think I’m gross? Oh. My. God I can’t believe I just told you that. There’s something exciting about telling a stranger embarrassing things. And besides, I’ll never even meet you. Leah has an older brother named Mike and his best friend’s name is Josh.

I had such a crush on Josh! He’s thirteen, with wavy brown hair that comes down just past his ears, deep brown eyes and a face that reminds me of an elf. He’s really cool and fun to talk to. The day I got a crush on him, I remember it. One time I came over for a play-date with Leah and Josh was already there with Mike. He stood holding a blue electric guitar in the living room when I pranced in. I was wearing purple corduroys and a yellow long sleeve, I remember because he started singing about me and my clothes.

“Purple Pants are in my brain!” He was practicing the same song he’d been practicing with Mike at school in the music room (Mike plays drums). It was an old song called Purple Haze and it was super awesome, I really liked it. It was so intense and deep sounding, you could hear the haze in the music. Except he changed Haze to Pants.

“Whatever it is, that girl / Put a spell on me.” Wow-wow Wooow, w’Wow Wow Wooow, w’Wow Wow Wooow. He played the notes and pushed his foot down on a little metal see-saw.

The most amazing sounds burst from the guitar like juice from a crushed fruit, his fingers zigzagging and picking and sending the sound waves everywhere. It was like the melody was telling a story or reading a poem, like if the Purple Haze had a funny magic tiger running through it, looking for a way out. And as he played, he got down on one knee and tilted the guitar so that the part with the knobs pointed up toward the ceiling, launching a sound rocket.

That was a month before the good part of our story, but I remembered it so clearly. I couldn’t stop thinking about him making those sounds, swaying, my purple pants in his brain.

I began to have daydreams about him. He would take me out on a romantic date by candle light, or maybe we’d go to a movie, or alone in some weird closet, or adrift on a lifeboat… I wanted to be in another place, alone with him, and I even imagined kissing him. French kissing.

The real thing, like the movies. But there was more. I wanted him to fill me up inside, up to the brim, or to somehow be wrapped in him like a blanket. Thinking about it made me tingle.

It made me feel like itchy wires were spreading through my body, guitar strings that played themselves. At first, they came out from my bellybutton; I imagined them spreading from there up to my chest, into my cheeks, then down my arms and out my fingers. But they began to yank and pull and vibrate somewhere else: my pussy. I remember the first time I really tried playing with my pussy.

You know, like that. On the wall opposite my bed was a full-length mirror, and right next to that near the floor was a little night light. I turned on the night light, turned off the regular light, stood in front of the mirror, and stripped down to my blue panties. I have a little girl body, no doubt about it. My chest is totally flat, not even any poky nipples.

My hips and butt are boxed in. And I definitely haven’t started growing any hair around my privates. For a moment, I wanted to be older, older for Josh. And when you look in the mirror, you always think you’re a little bigger than you are.

But while I stood there, I remembered when two 8th grade girls wandered past my classroom while the door was open, and one said to the other “Oh. My. God. Were we really that little?” Yup, I’m little. That’s the way it is for now. But, I thought, what if he just liked me the way I am now? What if I didn’t have to wait to be big?

The night light covered me in orange, and made my red wavy hair look like a candle in the dark. My freckly skin was made of sunbeams and whipped cream. I felt like the ocean girl standing in the seashell in the famous painting. I turned to my bed, which I share with Puff the giant white teddy bear. But instead of Puff, I pretended it was Josh, lying back, telling me how beautiful I am. I told him he’s so handsome, like a prince, as I got into bed. I was driving myself crazy.

The sheets seemed softer, my fingers felt bright, and when I wrapped myself around Puff – I mean Josh – I melted. I was in the song, I was the purple haze girl putting a spell on him. I turned on my side and wrapped my legs around him. I buried my head in Puff and pretended Josh was French kissing me, like in the movies. I was surrounded by the song, and it made me tingle between my legs.

I slipped off my undies and slid my hand down my body to my slit. I had only ever played with my vagina a little, and I had certainly never done it with the clear picture of a boy I knew kissing me and touching me all over. As I imagined him laying his hands on my chest, I felt the wonderful itch down there grow. My finger found my clit, I brought a hand to my leg and ran my fingers up and down before grabbing my butt.

The silly feeling instantly traveled from my button back to my butt crack, around my cheeks and up my spine. And every part of my body felt like I was touching it for the first time. I felt a mounting wave of something coming. Coming from a place way down inside, down in a place that had always been locked. The muscles down in my privates were being pulled in toward the gathering force, and as I kept rubbing my button and butt-cheeks, I knew that soon they would explode.

They did. An amazing blast pulsed across my skin and through my body. My vagina clenched and then relaxed as I was hit by a rolling wave. I arched my back and drops of sweat rolled down. I once visited California, and I was in a small earthquake. They don’t rattle or shake, earthquakes, they roll into you like the big, slow waves of the sea in the west. That’s what I felt. I felt what the earth must feel when there’s an earthquake. I felt how a beach feels a wave.

* * * About a week later, Leah invited me for a sleepover on Friday night. “Josh will be sleeping here too.” It was the last time she even brought up Josh. I think she knew somehow.

It was a rainy day, so we were stuck inside. And because we were stuck inside, Leah and me went crazy. And when we get crazy, we do weird things like covering Leah’s old Barbies in ketchup and baby oil. Leah’s mom yelled at us, and made us put the baby oil and ketchup away.

We got in trouble and I was almost sent home before Mrs. Bauman finally told me I could stay if Leah and I cleaned up. We put away the ketchup. We forgot to put away the baby oil.

For some reason, the baby oil got dropped in the TV room with the small couch. I would learn that later, after the dinner when Josh and I had the running joke about the dog, and kept laughing and talking a lot, and after dinner when Josh fell on the floor after sneaking a glass of wine, I was behind him and I landed on him. Later, when it was really, really late, like 2:00am, and everyone was asleep, I couldn’t sleep, so I went into the TV room with the small couch.

I was just going to put on the TV on low volume, maybe then I would get tired. I turned on the TV just as a face cream commercial was playing. Then I heard footsteps. Josh came in. “Hi,” I said quietly. I didn’t want him to feel unwelcome, but I was very nervous. “I can’t sleep,” he whispered. “Neither can I,” I whispered back. “I feel antsy.” “Antsy in your pantsy?” he said with a nervous giggle.

“Yeah,” I giggled back. I was sitting up on the couch now, my hands under my butt. My heart was pounding. “Have you made sure the bear doesn’t poop out his stuffing again?”

I giggled. The old teddy bear on the back of the couch had safety pins holding his guts in. “He’s fine.” Then I said what I needed to say. “Wanna see?” Josh came over to see what he knew he would see, the safety pins holding the bears butt closed.

I grabbed it and stuffed it in his face, giggling. “Why, you-” he said, making his voice sound like an angry Daffy Duck. Then he reached out and grabbed my sides and tickled me, before sorta tickling but mostly grabbing me. I almost howled in laughter, and as my laughs died down, his hands didn’t move away. “You’re a gorgeous girl,” he said. That’s it. I almost completely died. If I had had to pee I would have done it right there.

Almost stuttering, I said “I think you’re really handsome.” There was a long silence as his hands stayed at my sides, finger tips gently shifting. His face, his chest were so close now, I was shaking, so was he. His breath was getting hotter, then his lips brushed mine and… …I thought a thousand dolphins would burst out of a wrapped up ball inside and fly in a star pattern into the rainbow heart of the universe. At first it was just dry lips on mine, puckered up.

Then our mouths loosened and ah, it was wet! I gasped and pressed my face in. His mouth widened a little more and oh, his tongue! His tongue touched mine. I had to breath through my nose, and that’s when I really smelled him. It was a sharp, spicy smell, so different from the kids I knew. Almost like a grownup (eww!) but younger, so much younger, and sweeter and cleaner.

I loved that smell, that big boy smell. Then I realized, if I liked the smell of him, he must like the smell of me, the smell of a little girl. “You smell spicy,” I said. “I feel spicy,” he said. I felt power coming from him. “What do I smell like?” “Like sweet milk and cookies.” I was sweet milk and cookies, and he was my spicy meal. “Oh Josh, I feel like I’m dreaming.” “Me too,” he answered as he rubbed my back, and I rubbed his big boy shoulders and ran a hand through his messy hair.

Then his hands drifted to the hem of my shirt, and then he was lifting it up, and suddenly my shirt was off, and I moaned as his finger tips rubbed my nipples, and this whole time he was kissing me. Then he stopped, and kissed my cheek instead, then my neck, and now his lips were traveling down my body, sending goosebumps rippling as his lips brushed my nipples, and as he kissed and nibbled his hands moved to my lap.

He brushed his fingers against my tummy, then gently traced them across my hips and to my thigh, tracing sexy circles until he worked his way in, until…oh god, he touched my crotch through my panties, right on my clit.

As my vagina shuddered and my hips shook from the feeling, I thought it was time for a bold move of my own, so I slipped my hand straight into his pants, no underwear rubbing. I was so excited I could pop. I felt his thing, his wonderful big boy penis. It had a small patch of hair at the base, but was smooth. I pulled on it and he breathed heavily. Moments later, he slipped off his pants, pulled off his shirt and was totally naked. But I still had my panties on.

“What do we do now,” I asked? Without a word, his hand went into my panties. His fingers pressed into my crotch, in the front. I don’t think he expected it to be so soft.

His sweaty hands pushed in as they pushed down, toward my clit. I guided his hand with mine, to make him get the right spot. Then I lay back, and stared at the ceiling in my own personal heaven as he worked his fingers into my cunny.

We said nothing as his hands pounded my pussy, rubbing my clit and, oh, teasing the hole, searching the tickle zone between my pussy and my thighs, making me laugh and moan, the feeling building, until suddenly…”muuhh!” a small squirt of pee came out of me. “Oops!” I giggled, and he laughed too. I got up and ran to the bathroom. I barely made it. I felt so weird, I didn’t even know I had to pee until it was almost too late. The bathroom shared the same wall as the couch in the den. I hope he heard me.

When I got back, my panties were back on. I loved the feeling of him taking them off, and wanted to “restart” the adventure. I threw myself into his arms, straddling him, feeling his dick on my panties. We kissed for god knows how long.

Then he spoke again: “Aileen,” he whispered, “I’ve been thinking about you for so long. Your gorgeous red hair, your beautiful eyes, you’re wise smile.” Wise smile? Okay, that sounded corny, but it was still a compliment and maaaaan was he cute. “And your adorable, round butt!” He liked my butt! What a crazy idea, but also a good one. Before I could think, I jumped off his lap and lay on my stomach. I shivered with butterflies in my tummy, not knowing what would come next. He kissed the back of my neck and gave me goosebumps.

Then started massaging me. “Now, Aileen, baby,” he said softly, “I want you to do what you do in P.E. class, when you shake out all your muscles before stretching. I want you to wiggle the tightness out of your toes, legs, hiney,” he lightly tapped me there and I giggled, and each body part he told me to wiggle out and relax I did, finally with my head.

“Would you like me to rub your back?” “Yes, please,” I said. I was still nervous and excited, but after a while, his hands rubbing into my little back muscles made me limp as a fish. He was the baker and I was the dough. He reached my waist and stopped before kissing me on the base of my spine. I remember giggling into the teddy bear and some spit got into his fur. “Aileen, (smooch) baby, you’re so beautiful. Like a blossoming flower.” Feeling brave, I said “like the flowers on my undies!” and wiggled my butt. “Yeah, just like the flowers covering your little butt.”

He said as he tapped me back there again. “you have such a sexy little ass, has anyone ever told you that?” So many times that night my world had been spun around like a top. I never imagined that a boy touching my nipples, kissing my neck, running his hands all over my skin, could possibly feel nice and not just tickle a lot.

And now we went from “beautiful butt” to “sexy ass. I could understand him thinking my face was beautiful (he did think that), but my butt was different. Butts are supposed to just be funny, right? They’re for farting and pooping, things you don’t want boys to know you do. I couldn’t stop laughing as I scrunched up a bit from the weird idea, but I played along. “I’m glad you love my beautiful, luxurious ass, Josh.” Luxurious, like the voice in the soap commercial Leah and I kept seeing that day. The luxurious lather of Cove Essentials Moisturizing Soap.

“I’m going to love it even more in a second,” said Josh. I knew deep down this would happen, and it did. He tucked his thumbs into the elastic around my waist and pulled down my panties. He could see my naked butt with nothing covering it. Oh my god. Can you believe it? If a boy saw your butt you’d probably scream and yell at him.

And part of me wanted to do that but I was scared I would wake up Mike or his mom, or Leah, and I didn’t even want her seeing this now, even though she’s my best friend. But I liked that he could see my butt, even though I didn’t know why I liked it. And because I didn’t know why, it felt mysterious, which made it all more exciting. He began to gently rub my bare butt-cheeks, first up and down, then in circles. It felt amazing. It was like what I had done in my bed with Puff only better.

When a boy touches you, its better than when you touch yourself. Like, my science teacher told me the reason you can’t tickle yourself is that your body knows what your hands are going to do, but not with someone else’s! Anyway, he kept rubbing, and I could feel that the fingers of his right hand moving in circles, and my butt cheek moved with it.

And then said “Oh, my sweet little Aileen.” And I felt a kiss land on my skin. “Ohhh,” I squealed in surprise, as he laid kisses all over that sent waves of tickley, gooey pleasure down to my button in front and also up my spine to my head, pumping up the goosebumps like balloons. And as his kisses turned into nibbles and licks, he began to move toward the center, you know, toward my crack. I stopped making noises.

I wasn’t sure where this was going. He pulled my cheeks apart slowly, then planted a kiss on the inside of both. I could feel his hot breath like a tropical breeze, drying the sweat on my skin, refreshing the center of my crack. Then he dove in. His tongue hit my most secret of secret places, even more private than my vagina: my butt-hole! Oh my god, I couldn’t believe it! I was (I still am) nine years old; I had spent the whole day watching Disney and playing with Leah’s stuffed animals, running outside, and now a thirteen year old boy was licking my…my asshole! I clenched and unclenched my butt-hole as he licked. It felt so good but so nasty. Imagine if a boy walked in on you in the bathroom and saw you pooping. It was like on that level!

His tongue was licking right where my poop came out. Could he taste it? What did it smell like to him? Did I miss a spot? Those thoughts made me want to tighten up at first, but the licking was tingly and wet and it sent a dull, silly feeling up my butt. It should not have felt good, all the rules said it should not have — which is exactly why it was. And my skin right on my butthole and around it felt so sensitive and itchy, like it was ready to be licked. “Ohhgh, Josh!” I moaned “mhhmm” or something like that. He answered with a “mmmhmm” of his own, and poked his stiff tongue past my opening, and in. Oh, it felt so wonderful, as if an endless stream of silky warmth were pouring into my butt.

I pushed my hips higher to really jam it in. Suddenly, I felt a single finger slip in between my legs, searching around until it found my clitoris. Another went straight up my vagina. The feeling from both places was so powerful, I had to bury my face in the teddy bear to keep my moans from waking the whole house. The silly itch was still mounting, it had been growing this whole time. But it was getting stronger, as if there was a dam and the water was going to burst through. Any moment I was going to burst.

Any moment, my button and my butt-hole were going to collapse like a tower of blocks. “Josh, it’s gonna happen. Josh!” He poked his tongue in farther than ever, then pulled it out suddenly. He stopped everything and got up. I turned around to look at him. “Keep going.” “Hang on, baby. I want to try something.” “What?” “What about something bigger going in there?” “Like what?” I looked back and saw his stiff penis in the light that cut through the shades.

I saw him reach for the bottle of lotion that Leah had been playing with. “How about my dick? Would…do you think you would like that?” He was so nervous, his voice shook. I really should have freaked out, but I didn’t. At this point, it somehow made sense that he’s want to do that.

I just wanted something, anything, to go up my ass and scratch the itch he had planted there. “Do it,” I whispered. He paused, then I heard him unsnap the cap of the baby oil, and rub what sounded like a lot of oil on his penis. He leaned forward, wrapped his arms under my chest, with one hand sticky from the stuff. Then he kissed me on the cheek, and lowered the tip of his penis onto my butt. His dick found my crack, and I could feel it slide between my cheeks.

I imagined how soft and smooth it felt for him. It must have felt good for his dick. I clenched up, and my hole caught the very tip of his penis and pulled it for a sec before it popped away. I was hooked. “If you promise to be gentle, stick it in.” He did. “Ungh!” I groaned into the teddy bear.

I felt like I was pooping backwards! I felt the mushroom head of his hard penis slide through my butthole and into…into where? Into my guts??? I remembered the poster of the inside of the human body in my homeroom at school, with the intestines like someone spilled sausages everywhere. Was that where his penis was? Oh god! Before I could think about it for too long his dick went really far in (later he’d tell me it only went in about half way) and met the itch that had been planted in my asshole and was growing up my spine like ivy.

My sweet Josh was shaking, he was so nervous. Oh god, so hot, so full. I felt stretched to the breaking point. I imagined his penis growing into my whole body through my butthole like a tree. Josh started to relax, becoming more sure of himself. As he did, he sped up, and started talking. “Yeah, you like that. Take it.” And oh, did I take it. Took it deep into fantasy land, rode the Pegasus, down into the crystal cave and up to the stars beyond. I was an astronaut, and Josh was my rocket. Purple haze, up my ass! And again, “you’re so beautiful, Aileen.”

His fingers on my pussy rubbed even faster, and with his other arm he held me, firm but lovingly. Then, I broke.

“Ehhhhhhhhhhhhhhhehhhhhhhhehhhhh,” I let out as my body quivered and my ass shook. I felt like my asshole was eating Josh’s dick, the way it clenched and quivered. Something was happening inside that made the earthquake I felt in my own bed seem like nothing. I didn’t feel waves crashing, I felt the ocean, the Big Pink Ocean of Sex entering me like an unplugged drain, like I was getting sucked into myself. Josh exploded moments later. I felt his dick pump something into me, and the inside of my butt grew warmer.

Like microwaved honey splattering everywhere. A long moment later he pulled out his cock and I felt this stuff, this wonderful stuff spill out of my butthole and trickle down to my pussy, spilling into my vagina and even around it, tickling my clit. My butthole pulsed a few times and even more came out. I lay in silence for a while. I felt warm. I felt good. Finally, after like a minute, I said “Josh” quietly. Silence. We held each other for a while, kissing. Then he got up. I lay with my eyes buried in the cushions, then looked up to see he was gone.

I looked for him, my boy, my sweetie, but could not find him. I listened into the bathroom, tiptoed up to Mike’s room where I knew Josh was sleeping on the floor, even checked the basement. Nothing.

The next day, he spent the whole time in Mike’s room, the door closed. For weeks after, I would sometimes see him at school. I smiled and waved, and he would wave back. But over time he stopped doing that. He stopped wanting to look at me. I saw fear on his face when he saw me.

A few times, I thought I saw his lips say “I’m sorry.” Sorry for what? Then one day, he got into a fight. He punched like two other kids. I didn’t see it happen, but I heard one of the kids he punched said the name “Aileen.” Was he protecting me?

I’ll never know. He got suspended, and last week we moved. I wish I could text or Snapchat him, but I can’t find him. My heart is broken, but my mind is filled with hidden things, secret and sexy things.

The world is full of unknown passages to fun, behind every tree and rock, car or plane, or best friend’s big brother’s best friend.

I don’t know what happened to Josh, but I know why I’m here, now: I want to tell stories. I want to create new Joshes for myself when I can’t have real ones. When I grow up, I want to be a writer!


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