The Deep End


I was a bit of a young prodigy.  In some ways I was quite advanced for my age.  In other ways I was really immature.  Overnight it seemed like all the girls in my class had grown breasts and gotten interested in dating boys.  I was more interested in math, physics, and to a lesser extent, chess.  If I thought about my pussy at all, it was an annoyance; it had developed a habit of bleeding once a month.  As far as sex was concerned, I really couldn’t see what all the fuss was about.

One night, after having spent most of the evening working until my brain hurt on a proof involving the construction of a regular pentagon inscribed in a circle, I happened to pick up a book that my sister Valerie had left lying under the couch.  It was one of those cheesy paperbacks that she liked to read.  The cover featured a lurid picture of a frightened-looking blonde girl with enormous breasts and a very short skirt surrounded by leering thugs in leather jackets.  I couldn’t imagine what my prim and proper older sister got out of reading this kind of tripe.

Flipping through the pages, I quickly realized that the subject matter wasn’t simply lurid; it was downright pornographic.  The plot seemed to tell the story of a sweet innocent girl who was kidnapped by a biker gang and subjected to indignity after indignity.  Before I even looked at the clock, an hour and a half had passed, and I was halfway through the book.
While I was reading, I found myself been absently touching myself between my legs.  At some point I realized that I was starting to get seriously turned on. The sex scenes were affecting me in a way that nothing ever had before.  And while the bikers and their sweaty hard cocks certainly got me going, especially when they took their pleasure in violating the poor girl’s ass, what really did it for me (though it would be a long time before I would admit it, even to myself) was the obligatory lesbian scene where two captive girls did things to each other.  Things I had never before even bothered to imagine.

Nothing like that had ever happened to me before. I had a habit of playing with my pussy before I went to sleep; it was relaxing and felt kind of nice. This was a whole different ball game.  I was super-sensitive down there, and the sensations were amazing! My entire being seemed centered between my legs.  I could tell that my cunt had gotten really juicy and slurpy. My clitoris seemed to have swollen until it was the size of a marble. I couldn’t stop; I didn’t want to stop. I rubbed and rubbed until waves of pleasure washed all over me like surf at the seashore. So that was orgasm, huh?! No wonder everyone seemed to obsess out them so much… it was the best feeling ever. I knew right away that I had struck gold.  I immediately set out to have more.

From then on I masturbated every day. Occasionally I would get myself off multiple times in a day. I would give myself an orgasm or two before I went to sleep. Sometimes I sneakily borrowed Valerie’s trashy paperbacks (they were all roughly the same idea: Young British Lady Gets Abducted By Pirates; Dreamy American Tourist Girl Is Captured By Arabs; Innocent School Girl Falls In With Drug-Crazed Hippies; but none were as good as the first one I had stumbled upon). More often I just used my imagination.  I thought about sex a lot. I was very curious. Mom had, of course, explained the mechanics of reproduction and the female body to me when I had first started getting my period. She was a nurse, and had given me a very thorough clinical explanation of sexuality. That was fine, as far as it went; I certainly didn’t want to end up pregnant; but I desperately wanted to know about the good stuff.

I wasn’t very interested in the boys at school, and frankly they didn’t seem very interested in me either. I was kind of a freak. In my experience, nothing scares off the guys like a smart girl.  I wasn’t exactly a boy magnet.

My friend Aya lived up the block. We were the same age, and we had been best friends since junior high. Aya was half Caucasian and half Vietnamese, and still had the body of a little girl. She was short and had curly black hair, and a flatter chest than me. From behind, you might have thought you were looking at a twelve year old boy. Puberty seemed to have completely passed her over. We had never really talked much about sex, but one evening she called over to our house. “Lilly, come over here! I found something I’ve just got to show you!”

Aya had found a stack of old pornographic magazines from the ‘70s and ‘80s in a box in her attic, and we looked through one of them that evening while her mom and dad were out. I had never seen this kind of stuff before.  So when we leafed through the glossy pages, I giggled and said “Ewww gross!” the way I thought she expected me to, though secretly I found it weirdly hot. I really liked looking at the pictures of these naked women exposing themselves so blatantly.  Even though they had big, hair-sprayed hair and they all wore too much make up, I thought they were all incredibly sexy in a way I couldn’t imagine I ever would be.  I was jealous of their curvy, skinny, airbrushed bodies, their big round tits and perfect asses, and their fluffy, furry pussies. There was even a spread of two girls doing it to each other!  The girls on the black leather couch didn’t quiiiite touch each other, but they came really close, with extended tongues and scary red fingernails. In it’s own way, this was even better than Val’s nasty books.  By the time I went home, I was super turned on, all sensitive and juicy, and I couldn’t wait to run up to my bedroom and play with my clitty. Maybe I could get Aya to loan me one of the magazines. Or maybe, just maybe, Aya would want to act out some of the pictures we had seen.

I hadn’t expected anyone to be home at our house. Mom worked nights at the hospital, and Valerie was supposed to be out on a date. Valerie was 21 and she had a steady boyfriend, but she was a “good girl” and had told me before that sex was painful and gross, something that women were obligated to do for their husbands. Me, I had other ideas. I didn’t think that sex was gross at all.  I wasn’t scared.  I was obsessed, full of the burning zeal of the converted, a prude no longer.

There was a car parked in our driveway that I didn’t recognize, a beige beat-up Mazda that I suspected belonged to Valerie’s boyfriend, but all the lights in the house were off. I quietly let myself in and locked the door after me. I was about to head upstairs to my bedroom when a noise in the living room stopped me in my tracks.

Hardly daring to breathe, I tiptoed up the hallway and peeked in. There on the sofa was my saintly-ass sister and her boyfriend, Dave.

Dave was in his early or mid-twenties, tall and slim, with thick rimmed glasses and big ears and unruly hair. I had seen him before, and I thought he was really hot. I don’t think he had ever really noticed me before; he probably thought I was just a kid.

Dave and Val were on the couch, making out. They were kissing deeply, with open mouths, and Valerie’s shirt was open, her bra unsnapped, and her glorious big boobs were totally exposed. Dave was playing with her tits as they kissed, and she seemed to be encouraging him. Her nipples were erect, stiff and red and the size of gumdrops. I had always wished that I could have boobs like hers. From where I was standing in the dark hall, I could see the bulge in the front of Daves pants where his penis was straining to get out.

‘I SO wish I was Valerie right now’ I thought to myself. I was rubbing myself through my own pants ‘I would be all over that action!’

As I watched, Valerie’s skirt seemed to ride up all by itself. I saw her white panties, stretched tight over her pussy. Her legs seemed to spread as Daves’ hand found its way down there, petting her through her underwear. I was creaming in my pants.

Suddenly Valerie stopped him. “That’s enough!” she said in a voice that left no room for argument. I couldn’t believe it! Neither could Dave. He begged, reasoned, and pleaded, but her mind was made up. No more fooling around.

“Besides, my little sister could get home any minute. You don’t want her to catch us here like this do you?” My heart thumped in my chest.

“Could you at least give me a handjob?” Dave asked “I’m so turned on, I’m about to come in my pants.”

“No way!” Valerie made a face. She relented a little. “I understand that guys have… needs. If you really need to, you can masturbate in the bathroom.”

‘Masturbate in the bathroom?!’ I couldn’t believe what a prude my big sister was! And what a waste! What was this totally hot guy doing dating her? He could have any girl he wanted. If only I was the older sister…

It was a split-second decision. Quiet as a mouse, I slipped into the hall bathroom and sat down on the toilet seat.

Dave walked in a couple of heartbeats later. He flipped on the light and closed the door. Then he saw me.

“Lilly!” he hissed “What are you doing here? What did you see?”

“Ssh!” I whispered “We don’t have much time. I heard what Val said, and I felt bad for you. I’ll give you a handjob.”

“What? You’re too young!”

“Am not! I’m old enough.” I said, eyeing the bulge in his pants lustfully. “Come on, take it out, I’ll show you.”

Dave really wasn’t in any condition to argue. He unsnapped his jeans, dropping them around his ankles. His hard prick eagerly sprang out of his boxer shorts.

I was a little surprised at how big it was. All that was supposed to fit up inside your pussy? Still, it looked really nice. His cock was a thing of beauty, a throbbing, pulsing, obscenely sexy living sculpture.  I wrapped my hand around it. My fingers barely reached around its girth. It was scalding hot in my hand. He was rock hard and quivering. The mushroom shaped head was bright purple, and oozing clear liquid from his pee-hole. Tentatively I stroked it. I was surprised at how silky soft he was, despite being so hard. It felt really good to touch him. His balls were drawn up tight. ‘How weird’ I thought ‘To have so much stuff hanging out between your legs!’

“Hurry up!” he whispered “I don’t want Valerie to get suspicious.”

It didn’t take very long at all. I loved stroking his cock. It made me feel incredible; powerful and sexy. I mashed my thighs together as I jerked him off, squishing my swollen cunt-lips together. I squeezed his penis hard and moved my hand as fast as I could. Suddenly it happened. He half moaned, half growled, and his entire body went rigid as he squirted glob after glob of pearly white juice out of the end of his penis.

“Don’t stop” he whispered as I milked his softening prick. More and more leaked out. Of course I knew that sperm came out of a guys penis, but I had never imagined that it would be so much, or so forceful. How cool! It had gone everywhere; onto the wall, onto the toilet, on the floor, on my hand. I tasted a little. Not bad, a little salty.

“Dave, are you done yet?” Valerie was just outside the bathroom.

He kissed me softly on my head. “I’m just cleaning up. I’ll be out in a sec!”

“Hurry up!” my sister said from out in the hall “I’ve got to go to the bathroom.”

Dave and I hurriedly mopped up his semen with toilet paper and flushed the evidence down the toilet. He kissed me again, on the forehead. Then I hid behind the shower curtain.

I heard Valerie sit down and pee. I expected her to flush and leave, so that I could make my escape up to my bedroom. Instead, Valerie stayed sitting on the commode. I heard little squishing noises, heard her breath change and become more rapid, and I knew that she was masturbating. I never would have imagined that she did it; she was such a good girl. Well, I had just given her boyfriend a handjob. I suppressed a giggle.


I gave myself three or four orgasms that night, and more over the next couple days as I replayed the memories of Dave and his big sexy dick. I was hungry for more.

“Are you going out with Dave tonight?”

“Yeah” Valerie answered absently “We’re going to see a movie. Why?”

“Could you get him to drive me over to my friends’ house? Her mom said she’d drive me back home? Please?”

It took a little begging and wheedling, but Valerie agreed to ask Dave for me. Dave didn’t seem to mind too much.

“Where does your friend live?” he asked as we drove down the block. The car was humming with sexual tension. I was wearing my pink party dress, which was a couple years old and a little small on me. It rode halfway up my thigh. I wasn’t wearing any panties.

“Right there” I replied, pointing back at Aya’s house. “Keep on driving.”

“Listen” Dave said “About the other night…”

“Did I do a good job?” I asked.

“Yeah” he said “Yes you did, but…”

I could see the bulge that had formed in the crotch of his jeans. I could tell he was at least as horny as I was. “I want to do it again” I said “I want you to teach me all about sex.”

“We shouldn’t. I’m too old for you.  You’re too young.  It wouldn’t be right. I’m dating your sister.” he added almost as an afterthought. “We can’t have sex, Lilly.”

“But we could do the other stuff” I persisted. I was a little disappointed; I was really looking forward to losing my cherry to him. But I wasn’t going to give up that easily. “Like you could teach me how to give a blowjob.”

He pulled up into a driveway, and used a remote controller to open the garage door, which closed after us. We were alone in the dark.

“This is my place.” He said “Don’t worry, my roommate isn’t home. We don’t have much time though. Valerie thinks I’m just dropping you off.”

“Kiss me.” I said. He hesitated. “I’m not in love with you or anything. Just kiss me, please.”

We kissed for a while, and I thought it was really nice. I liked having his lips pressed against mine, his tongue in my mouth. I was starting to get highly turned on. But he was right; we really didn’t have much time. I would have to figure out a way for us to have some private time together. Meanwhile I wanted to use our time to the best advantage.

I broke off the kiss. “Would you like me to suck your dick?”

His penis could have answered for him: it was practically bursting the zipper of his jeans. “Only if you want to.” he said.

Oh boy did I ever! Some of the girls at school talked about blowjobs like they were something gross; something that girls had to do in exchange for dinner and a movie. Not me. I thought it was super-sexy, and I couldn’t wait to get my mouth on his thing.

He unzipped his jeans, letting his penis out. It was just as big as I remembered, if not bigger. (Looking back, I realize that he was about average size, maybe a little bigger. At the time though, his tool seemed the size of my forearm.) I didn’t know how I was going to get that thing in my mouth, never mind my pussy.

“Just start by licking it” he said “Like a popsicle.”

I lowered my head to his lap, stuck out my tongue, and licked the length of his shaft. He groaned as my tongue reached the sensitive purple head. I tasted the clear liquid that was oozing out of the end. It was sweet and sticky. I was hooked.

So was he, apparently. We took it kind of slow, with him stroking while I licked and (very gently) played with his testicles. As we got into it, and we both got more and more excited, I took the end of his penis in my mouth. I could only get about half of it in, and it filled up my entire mouth. It felt incredible. It was a little bit scary, having that huge living thrusting thing in my mouth like that. I was afraid I might choke, or accidentally bite him. Mostly though, it was just fun and sexy.

I felt his hand on my inner thigh, snaking up under my dress. As I kept sucking, I wriggled around to give him better access. His exploring fingers found my vagina. I reached down and helped him find my clit, which was all swollen and revved-up and sensitive.

Dave rubbing me was even better than me touching myself. He kept his fingers nice and slippery from my oozing vagina, and diddled my button until I thought I had died and gone to heaven. If this was what sex was about, I was all over it!

Dave’s thrusting in my mouth was becoming more insistent as he fingered me. I concentrated (as best I could while his fingers drove me crazy) on sucking him as hard as I could.

“I’m going to come!” I knew what that meant. I wanted to make him do it into my mouth. His fingers momentarily stopped working their magic as his whole body went rigid and his ass lifted up off the drivers’ seat. Suddenly, he was squirting hot, salty, sticky boy-come into my mouth. I swallowed and kept sucking. It wasn’t nearly as much stuff as the other day, but it still felt like a lot. I swallowed all of it. I liked that he was really inside me now.

His fingers started up again as his shrinking wet dick plopped out of my tired mouth. My own body shook as his rubbing sent me over into orgasm. It didn’t stop, it just kept going and going like a wild roller-coaster ride. I thought I was going to pass out as I ground my sticky pussy onto his hand.

At last it was over. I licked his finger off, and we put our clothes back together. I felt like I was floating. We kissed again, like friends this time.

He drove me back to Aya’s house, which was just three houses down the block from my house. On the way, Dave told me that he’d never done that before.

“What?” I asked “Gotten a blowjob or played with a girl’s pussy?”

“Neither one.” he said “Your sister is the only girl I’ve ever seriously dated, and… well you know.”

I was amazed. Dave was 24, worked with computers at an office, and was gorgeous. “Have fun at the movies” I said as he dropped me off in front of Aya’s place “Who knows, maybe you’ll get lucky tonight.”


I had dinner with Aya and her mom and dad. It was hard not to tell her what I had just done. She was my best friend. But it was my secret. I thought about how bad my sister would feel if she ever found out, and I resolved never to tell.

After dinner, while her parents watched a movie downstairs, Aya and I hung out in her room. She got a magazine out from under her bed. We leafed through it, giggling at the pictures and softly reading the stories aloud. I was thinking about the things I had just done with Dave, and getting excited all over again.

Finally I had to ask her. “Aya, do you ever, you know, masturbate?”

She burst out laughing. “Yes! All the time! I was afraid you would think I was a pervert or something!” We both laughed and laughed with relief.

“Do you want to do it?” I asked when we had stopped laughing. “Now?”


I nodded.


We silently stripped out of our clothes and lay down, completely naked on her bed. We held hands as we started rubbing.

“How often do you do it?” she asked me.

“Basically every day.” I answered “Sometimes more than once.”

“Me too.” she replied.

We started out lying side by side, but after a little while, we moved so that we were sitting on the bed facing each other. That way we could watch. Aya’s body was fascinating; all the same parts were there, but it was the differences that were interesting. She was a tiny little thing. Her boobs were smaller than mine, and her brown nipples stood straight out. She only had a thin triangle of black pubic hair, but her pussy lips were puffy and more prominent than mine. I could see her inner lips peeking out, glistening with moisture. I had never really looked at another girl naked before. I thought it was cool. I liked watching her play with herself. It turned me on.

“Oh Lilly” she half whispered “I’m going to come.”

“Me too” I replied.

She spread her legs even further apart, and slipped one finger up into her hole as her other finger stayed busy on her clit. I copied her actions, feeling her eyes on my splayed vagina. We came at almost the same time. It was incredible.

“That was so much fun!”

“I’m glad we did that.”

“I’m glad you’re my friend.”

After that, we got dressed, and I went home. Valerie wasn’t home yet. I went to bed and masturbated one more time. My pussy was tender and sore, but satisfied. What a day it had been!


That Saturday, Val and Dave were going to see a movie in the afternoon. Valerie asked if I wanted to come along

“Sis” I said, feeling guilty “I don’t have to come. I don’t want to screw up your date.”

“It doesn’t matter.” Valerie said “We’re just going to see a movie.”

I don’t even remember what the movie was about. I think it was a comedy. I sat next to Dave, and he sat next to Val. Hardly anyone else was in the theatre. Dave and Valerie held hands. I played with Daves penis through his pants. It felt naughty and exciting and super fun. He was so hard! I didn’t want to make him come in his jeans. I was just priming him for later. When Val got up to go to the bathroom, I stuck my hand down his pants, and gave his hot erection a squeeze. He took the opportunity to reach down between my legs, where I was already quite moist, teasing and petting my wet pussy through the frustratingly dense material of my pants.

“Try and play with her pussy!” I whispered in his ear. “I bet she lets you.”

When Valerie sat back down, Dave casually let his hand fall onto her lap. She didn’t seem to mind. As I surreptitiously watched, his hand slipped under her skirt. She still didn’t object. Her skirt rode up and up her thighs, which were now slightly parted.  At last I could see her white panties in the dark movie theatre.  Dave’s hand kept busy between her legs while I softly stroked his penis through the denim of his jeans.

After the movie, Valerie said she had homework to do. My bet was that she was going to go masturbate. I asked Dave if he would drop me off at my friends’ house. He said sure.

“Did you make her come?” I asked as soon as we were alone.

“I don’t know.” he said “I don’t think so.”

“I want to taste your finger” I giggled “Is that weird?”

“I don’t mind.” he said, extending his finger for me. I sucked on it, pretending it was his dick. I thought I could still taste my sisters’ pussy juice on it. I felt so horny I thought I was going to go crazy.

“Where are we going?” I asked.

“I don’t know. We’ve got all afternoon, but we can’t go back to my house. My roommate is there.”

“What about the park?”

“It’s a nice Saturday. Everybody will be there. But I do know a place we can go there. It’s kind of a long walk.”

We pulled into the state park. Dave was right; the parking lot was almost full. He took me along a hiking trail, deep into the woods. Abruptly, we left the trail, and made off into the forest.

This seemed private enough to me, although the ground was going to be a little scratchy. Dave pointed up ahead though. A finger of rock rose out of the ground, catching the sunlight. It was big as a house, and seemed totally unclimbable. I didn’t know what he was planning until he pointed out a place where the rock jutted out. Behind that was a hidden gully that led straight to the top.

The top was like a stone table, smooth and bare and warm and sunny. “I found this place when I was a kid.” Dave said “I don’t think anybody else knows about it. I’ve never shown anyone before.”

I was glad that Dave had shown me his secret place. It was really nice there. For a few minutes, we just sat together, enjoying it.

Dave lay down on his back, and I lay down on top of him. We kissed for a while. Then I sat up. “Take off your clothes” I said “I want to see you all the way naked.”

“I want to see you too.” He said as he stood up and started stripping. His body was beautiful, slender and pale, with just a hint of a beer-belly and a little treasure-trail leading up to his navel. I loved seeing him naked. He had the cutest tight butt. His penis hung thick and halfway hard between his legs. “Your turn.” he said.

I felt suddenly self-conscious, but I stood up and started taking off my clothes. I hoped he wouldn’t be too disappointed in my body.

“You’re beautiful” he said, and from the sound of his voice and the look in his eyes, I could tell he meant it. I glowed.

“Did you like playing with Valerie while I played with you?” I asked “I thought it was really sexy.”

His dick swelled at the memory.

“What did her pussy feel like?”

“Like yours, but more hair.” He grinned.

“I think hairy pussies are nice.” I said “I wish I had big boobs like Valerie’s. Why do you think she’s so weird about sex?”

He frowned “I think she had a bad experience when she was younger. She doesn’t like to talk about it.”

I thought about that. It kind of made sense. She had never said anything about it to me, but she was always warning me about guys, and she seemed so anti-sex, even though she had this hot boyfriend. Who I wanted to fuck really bad, I thought guiltily.

“If Valerie ever has sex with you, will you still want to do things with me?” I asked.

“Yes” he answered “Sure I will.”

“Do you want to do things with me now?”

“Yeah I do.”

“Do you want to fuck me?”

He looked at me. His dick was getting hard again. “We can’t do that.”

“You won’t get me pregnant. I have a condom in my jacket pocket.”

“I don’t want to hurt you.”

I pouted a little.

“Lilly” he said “I’m dating your sister. I can’t fuck you.”

I guessed that was a line he couldn’t cross. I didn’t really understand the distinction, but I could hardly force him to fuck me. I figured I should be happy with what I had got.

“I’d like to eat your pussy.” he said “If you’ll let me.”

Of course I’d let him! He kissed his way down my neck, down my chest, nibbling on my small boobs and planting kisses all over my stomach until I was just frantic with lustful anticipation.  As soon as his mouth was between my legs, I was in heaven. His tongue was all over me, dancing around my pussy, eating me alive, tantalizing my engorged eager clit.

“Put a finger inside me!” I begged. I was still turned on from the action in the theatre, and I knew I wouldn’t last very long.

Gently, he complied. His finger felt huge invading the hole where only my small index finger had been before. For a second I was glad that he wasn’t going to fuck me. I didn’t know if he would be able to fit his penis in without ripping me in half! His finger was big enough! I gasped as he invaded me. It didn’t hurt though, and as my little pussy got used to it, it felt really good, especially when he started moving it in and out.

He kept his tongue on my clit as he finger fucked my pussy, and I had an orgasm like I had never had before! I moaned and writhed and kicked my legs, but he held me tight against his face until I was all done.

I kissed him all over his face, tasting my tangy juice on his lips and chin. “Thank you thank you thank you!” I told him “Now it’s your turn.”

He let me explore all over his body. I kissed every inch of him, from his toes to his ears, avoiding for now the succulent treat between his legs. I sucked playfully on his nipples, which weren’t that much smaller than my own. I kissed his tummy, sticking my tongue into his bellybutton, which made him giggle. I kissed his tight butt, and even kissed down into the dark musky crease between his cheeks.

At long last, I kissed my way up his ball sac, and finally put my mouth on his delicious cock. I could tell he was really turned on, and I wanted him to feel as good as he had made me feel.

He lay on his side as I curled up at his knees and sucked him. I still couldn’t get the whole thing in my mouth, but I got as much as I could in, and stroked the rest with one hand. He started slowly humping my mouth. I knew he was being gentle and making sure not to hurt me, which I thought was sweet. He played with my hair while I sucked him.

I let my free fingers explore between his muscular butt cheeks. He didn’t stop me, so I guessed he didn’t mind. I thought his ass was so sexy. Touching him there, in that private place, made me just melt. I heard him groan, and his whole body quivered when I found the ring that I knew must be his butt hole. Ever so softly, not wanting to hurt him, hoping he didn’t think it was gross, I tickled his butt. He seemed to respond by humping my mouth more urgently. His cock seemed to swell in my mouth. Throwing caution to the wind, I pressed my finger against his hole. He seemed to open right up, letting my finger in to the second knuckle. It felt incredibly sexy to be up inside him like that. As gently as I could, I started fucking his butt with my index finger, the way he had done my pussy before.

He erupted in my mouth, filling me with spurt after spurt of his semen. I hungrily swallowed it all. I kept sucking until his penis got too sensitive, and I had to let it out of my mouth. My finger popped out of his butt, and we cuddled in the sun, naked together.

I hoped he didn’t think it was weird that I had played with his butt. He didn’t say anything about it. After a while, we started to get turned on again. I could feel the end of his penis tickling my tummy. We kissed and touched for a little while, until he was rock hard again, and I was just melting. Dave rolled over onto his back on the warm flat rock, and I climbed on top of him, facing his toes, and we “69ed”.

I just couldn’t get enough of his dick. I licked and kissed it, mostly using my hand to stroke him so I could watch as he got more and more excited. I wanted to see him come again.

Meanwhile he was busy between my thighs. His kisses and licks down there were coming close to pushing me over the edge. My butt felt naked and exposed. I hoped that he would play with it the way I had done his.

I felt his breath between my butt cheeks, and then I felt his tongue exploring back there. I took a huge breath and started jerking his cock wildly. The sensation of his tongue near my anus was incredible. He slipped his finger into my ready pussy and tentatively licked my asshole. In seconds, I was coming again, wiggling my butt, trying to get more of Dave’s tongue and finger inside me. He came too, splashing his white come onto my face and his tummy. There wasn’t a lot this time, but it was thick and gooey. I licked up the droplets on his stomach, and he licked himself off my face. After a while, we got dressed again, and walked back to his car. He dropped me at the end of our block, and I walked home. I couldn’t wait to get together with him again.


Aya had found something else in the box of dirty magazines. At the bottom of the stack, she had found a large manila envelope. In it were all the love letters her parents had sent while they were in college. Some of them were really explicit.

“Dear Jack” Aya read aloud as she lay on her bed. I was leafing through an old Penthouse Magazine. We had told her parents that we were studying together. It was actually kind of true.

“‘Last weekend was too wonderful for words'” Aya read on. “‘I get wet and have to touch myself just thinking about it. Five weeks seems like an eternity. I wish we went to the same school, or lived in the same town. I can’t wait to see you again, to sleep next to you, to be in your arms, to have your hot cock inside me again.'”

Aya looked over at me. “Oh my god” she said “I can’t believe my mother wrote that. About my Dad!”

I thought it was hot. She read on “The next time I come over, I want to have you every way possible. After I suck you and you lick my pussy, I am going to climb on top of you and fuck you until you come inside me. Then, when you are ready again, I am going to make your dick nice and slippery, and I’ll bend over and spread my cheeks wide and you can fuck me in the asshole.”

“Can you believe this?” It was a little hard to picture: Aya’s dad was a big guy, and her mom was a tiny little thing, smaller even than Aya herself. “She wanted my Dad to have anal sex with her. Do you think that’s weird?”

I dodged the question. “Aya, I need to masturbate. Is that ok?”

“Of course” she said “I’m horny too. Let’s do it.”

We quickly wriggled out of our pants and underwear, leaving our tops on. We lay on our stomach on her bed, silently reading more of her Mom and Dad’s sexy letters to each other. I thought they were better than looking at pictures. Her parents had had a really hot sex life. We played with ourselves as we read, getting more and more turned on.

Suddenly Aya stopped reading and raised herself up on her elbows. “Lilly can I tell you a secret?”

“Of course” I said

“Promise you won’t laugh at me or think I’m weird”

“Of course I won’t. I’m your friend. What is it?”

Aya leaned over and rummaged around under her bed. She had a really tiny little butt. I had an urge to caress her, but of course I didn’t.

She came up with a big pink dildo. It was made of clear material with sparkles in it, and it was realistically shaped like a penis. It was even bigger than Dave’s dick.

“Oh Aya!”

“Sometimes when I masturbate, I use this” she said “Is that too gross?”

“No!” I said “I think it’s really sexy.” I was tempted to tell her my secret, but I couldn’t. “Maybe you could let me borrow it sometimes?”

“Sure” she grinned shyly “Any time you want. I used to use my hairbrush, but this is SO much better.”

She pulled her shirt off and lay back on the bed, legs spread. She started rubbing the dildo up and down her slit. She turned a knob, and it hummed as she worked. She pressed the end of it against her entrance, and her pussy seemed to open up like a time-lapse picture of a rose blooming. I couldn’t believe that thing fit inside her little body, but it slipped right up into her pussy.

“Oh Lilly” she moaned as she fucked herself “It feels so good! I can’t believe you’re watching me do this.”

I couldn’t believe it either. I was so turned on. I couldn’t help myself; I knelt next to her and put my hand on the end of the dildo protruding from her pussy. She relinquished control, moving her hands up to her erect nipples.

I relished fucking her. I slid the dildo deep inside her and then pulled it almost all the way out. Her labia seemed to cling to it like a baby nursing a bottle. The pink toy glistened with her wetness. I pushed it back up inside her and she moaned. I fucked her harder and faster, until my arm started to ache. Her clit peeked out near the top of her vagina, pink and swollen and cute as a button. Not knowing what she would think, I lowered my mouth to her crotch. Still fucking her, I stuck out my tongue and touched her clit with the tip of my tongue. I heard her sharply inhale. I pressed on, licking her clit and fucking her pussy. She tasted tangy and nice. Her body twisted and shook, but I didn’t stop. I kept my tongue pressed against her little clit and the dildo deep in her pussy until her body finally relaxed.

“Lilly” Aya gasped when she found her voice again “That was beautiful! May I?”

I lay back and let Aya crawl between my legs. Her tongue and fingers on my sex felt great. Like Dave, but different: gentler and more tentative. I was so turned on I was sure I was leaving a huge puddle on Aya’s sheets. She pressed the pink toy against my hungry cunt, and I opened up for her. I was a little afraid that it was going to hurt, but it didn’t, not at all. I just felt really full. The buzzing and friction inside my pussy was incredible. I felt a finger brush against my super-sensitive asshole. An accident? I moaned aloud and gave myself over to the pleasure.

When it was over, we rested for a while, just holding hands.

“I liked that.” said Aya. I could still see my come drying on her face.

“Me too” I said

“Does this make us lesbians?”

“I don’t think so” I said, thinking of Dave.

“Me either” she said “but I’d like to do that again, if you don’t mind.”

“I’d like that too.” I was thinking about that dildo of hers, and all the things that we could do together.


I snuck out the back door when I heard Dave drop off Valerie at our front door. I knew I was taking a risk, but I was pretty sure I could get away with it. Val probably wouldn’t check up on me, and if she did look into my room, I had arranged the pillows so it looked like I was sleeping under the covers. Mom wouldn’t be home until 6 a.m. That should leave plenty of time.

I met him at the end of the block. Nobody saw his car pause at the stop sign while I got in.

“Did you have a good date?” I asked

“It was pretty fun. She gave me a handjob. And she let me play with her pussy again.”

I felt a little jealous, but not very. He was her boyfriend after all. And I was glad my sister was loosening up. “Did she make you come?”

“Yeah.” He laughed “She was kind of grossed out by it.”

“Did you save some for me?” I hoped I didn’t sound plaintive.

“Oh yeah, don’t worry Lilly” he said, and kissed me, “There’s plenty left for you.”

“Are you going to fuck me tonight?” I asked, only half teasing.

“I can’t” he answered. “You know that.”

I still didn’t understand the logic of his ethos; we were already doing stuff we knew we shouldn’t be doing.  What was the difference if he was putting his penis in my vagina or somewhere else?

“You know” I said, trying to sound casual “I heard at school that some people like to do it in the butt.”

“Do girls actually like that?” he asked.

“Some of us do” I said, looking up into his eyes “I think.”

“Do you want that?” he asked “With me?”

“Yeah” I said “But we should get some lube. You need lots of lube. That’s what I heard.”

We pulled into a drugstore, and he came back red faced with a small bag in his hand. There was a little bottle in the bag, full of clear liquid. The label said ‘AstroGlide’. I couldn’t believe we were actually going to do this.

We went over to his apartment. His roommate was out. We climbed up onto his bed and kissed and made out for a while, taking our time undressing each other. I liked it when he played with my nipples. Just having him kiss them made them super sensitive, and sent jolts down to my little clit.

“I want to do everything with you” I said.

“Someday Lilly” he answered “Some day.”

“Tonight” I said “I want you to be in my ass.”

“Are you sure you want it?” he asked.

“Oh Yeah”

“Are you sure it will fit?”

“I’m sure” I said, trying to sound confident.

“Ok” he said. “Just tell me if it hurts too much.”

I climbed on top of him, and we did the 69. I used my mouth to play with his dick, bringing him to rigid excitement. He concentrated on my ass, licking and touching my hole until I thought I would go crazy with anticipation. My little pussy was drooling all over his face. I felt his fingertip invading me back there. It felt good.

“Please, Dave I want your dick.”

I crawled off him, and got down on my hands and knees, displayed lewdly like one of the models from Aya’s dirty magazines. Dave got the little bottle out, and as I watched, he spread lubricant all over his cock. I wanted him so badly.

He squirted a bunch of lube onto my asshole. It felt cold, and made me giggle.

“Are you ready?”

“God yes” I answered, wiggling my behind in what I hoped was a sexy way “Please put your penis in my butt”

He knelt behind me, and as I watched, guided his erection between my butt cheeks. When the head of his penis bumped against my anus, a jolt of sexual electricity shot through me. I moaned and closed my eyes, pressing back against him.

At first I didn’t think it was going to go in at all. It was like pushing against a brick wall. Suddenly, I felt something let go, and he slipped in.

It hurt. I was scared that I couldn’t take it, that my ass would be split open. I felt this huge pressure stretching my butt. I couldn’t help but make a little whimper.

“Are you ok?”

“Yeah” I whispered “How much of it is in me?”

“Just the head” he said “Do you want me to take it out?”

“No” I said “Just don’t move for a second.”

I don’t know how long we stayed like that, with the head of his penis buried in my poor little asshole. He patiently stroked my hair as I knelt there, trying to get used to the sensation. I really wanted it; I really didn’t want him to have to take it out.

“Try putting a little more in”

He pushed forward, and I felt his dick sliding up my asshole. I realized that it didn’t hurt anymore. I just felt incredibly full.

“Try a little more.”

He pushed forward a little more, and I pressed back against him. It felt really good. Just a little scary still, like I was right on the brink between pleasure and pain. I didn’t want to stop.

It took a long time, but finally I felt his soft pubes against my butt, and he whispered in my ear that he was all the way inside.

“Now fuck me” I commanded him. He started slowly sliding his thing in and out of my ass. The pain had all gone away, and now it was all sweet sweet pleasure. I can’t even describe the sensation. Every time he pushed inside me, it seemed like his dick bumped into the back of my clit. I was delirious.

My finger found my clit. It was hard to keep my finger on my button with him thrusting into me, but it didn’t matter. Orgasm was washing over me like a tide. It was beautiful. I felt his finger slip inside my cunt as he fucked my ass harder and harder.

“Please come in me Dave” I begged “Please come in my asshole!”

I ground myself back on him as his cock spasmed in my ass. His finger in my pussy sent shockwaves through my body. I loved feeling him come inside me.

We extricated his soft cock from my ass. I felt tender and happy and a little sleepy. I wanted to cuddle, but he seemed kind of antsy, so he drove me home.  In the car, he talked about how he thought he was in line for a promotion to manager.  It was about then that I came to the realization that he wasn’t much of a conversationalist: all he ever wanted to talk about was office politics, computers, and a smattering of NASCAR.  Two of those three didn’t interest me at all, and the aspect of computers I was interested in was algorithms and logic trees, not which model had the fastest processor.  He dropped me off with plenty of time before Mom came home.  I crawled sleepily into bed, with Dave’s juice still leaking from my butt.


“Are you fucking my boyfriend?”

I was sitting at my desk doing homework.   Half of my mind was working on differential equations; the other half was happily daydreaming. My ass was still a little tender and buzzy from the other night. I was wondering if I could get Aya to fuck me in the butt with her vibrator. I wondered if she’d let me lick her there.  Would that be too weird for her?”

Valerie was standing in my doorway. “Are you sleeping with Dave, Lilly?”

My heart stopped. I had never wanted to hurt Val. “No” I said “But we’ve been doing… stuff together.”

“What kind of ‘stuff’?”

Oh God.  I felt like a shit.  “He’s been teaching me things… oral sex and anal sex…”

“He did that to you?!”

“No!  I mean, yes, but I asked him too.  It was all my fault, really.  I started it.  I’m sorry Valerie.”

She came in and sat down on my bed.  She looked hard at me, and I felt like I might shrivel up.  “Lilly, did you know I lost my virginity when I was your age?”

I shook my head ‘No’.

“It wasn’t my choice.  Two of the counselors at Camp Kinnikinnick did it to me.  They were bigger than I was, there wasn’t really anything I could do.  It hurt pretty bad, but the way I felt afterward was much worse.

“I hope you know what you’re doing,” she said to me, shaking her head, “The world is a bigger and scarier place than you know.  You’re swimming in the deep end of the pool now, sis.”

It was really chilly around our house for about a week.  Mom must have known there was something wrong; her two daughters weren’t speaking to each other; but of course she didn’t know what the problem was.  We generally got along pretty well, and when we did fight, we usually got over it in short order.

So the next Friday, when I was moping around my room, not concentrating on the chess problem I had set up on the board, thinking instead about Dave and his big dick, hating Aya for going out of town with her parents for the weekend, Valerie tapped on my bedroom door.

When I let her in, her face had a softer expression on it.  I began to think that maybe she didn’t hate me forever.

“Lilly, do you really want to have sex with Dave?”

“Well…” I replied, figuring honesty might be the best policy, “Yeah, I do, but…”

“I’ll let you do it,” she said, “Just once.  On one condition.”

“Really?  For real?  What’s the condition?”

“That I get to watch.”


It was Sunday afternoon, and Mom had just left for work, when Val came to visit me in my room again.

“Dave’ll be over pretty soon,” she said, “You should get undressed.”

I stood up from my desk and stripped naked under her watchful gaze.  I felt really self-conscious getting naked while Valerie watched.  When I was all the way undressed, she nodded approvingly.  “Nice.” she said, “Now lie down on your bed.  I’d like to tie you up.  You don’t mind, do you?”

I didn’t object.

Valerie took out a length of clothesline and used it too lash my wrists together to the top of my bed.  It wasn’t so tight that it was uncomfortable, but I didn’t think I could get out of it very easily either.

“Now wait here.” Valerie said with a wink, and left the room, closing the door behind her.  My clit was already humming with anticipation.

It was a good ten or fifteen minutes before she came back in with Dave in tow.  She had stripped down to her underwear: big white no-nonsense panties and her Battleship Missouri bra.  Dave was nude.  His dick was already half-hard, and when he saw me tied naked to the bed, it rose straight up to full attention.

“Doesn’t she look cute like that?” Valerie asked, licking her lips like a cat, “She wants to suck your dick, don’t you sis?”

I nodded my head eagerly.  I most certainly did!

Dave climbed up on the bed and presented my hungry lips with the big juicy head of his glorious dick.  I was looking forward to showing off my skills to Valerie, and giving Dave some serious pleasure with my mouth and tongue.

“Put your penis in her mouth!” she instructed Dave, and slid the end of his cock in between my eager lips.  With an impatient eye-roll, Valerie reached behind my head, grabbed my pony tail and forced my head down on his cock until I gagged.  First I was surprised, then appalled, then turned-on by it, but mostly I was struggling to breathe around his big rampaging dick.  I tried to say something, but all that came out was a gurgle.

I felt like one of the kidnapped princesses in Valerie’s trashy novels, and with a flash, I realized that was exactly what I was.  I could see a few stray hairs around the crotch of Valerie’s panties, soft and dark, and I reveled in the lust of it all.

I’m not sure how long that went on.  Just when we were starting to get some kind of a rhythm going on, Valerie put a stop to it.  Reluctantly, Dave pulled his wet dick out of my gaping open mouth.  My jaw muscles ached, and my windpipe breathed a literal sigh of relief.

Valerie grabbed my ankle and pulled my foot up toward my ear.  “Do you want to fuck her?” she asked Dave, “Look at her vagina.  She wants you!  Do you want to fuck that horny little pussy?”  He nodded dumbly.

“Well then you’d better put on a condom then, huh?”

I watched eagerly as Dave carefully rolled the condom onto his cock.  He looked even bigger and juicier than ever.  My cunt was beyond wet; I was soaking.  I felt like I had already made a big wet puddle on my bed.  My pussy felt like it was absolutely gushing.

My legs were spread wide apart.  Dave climbed up onto the bed, his rock-hard, latex-covered dick bobbing happily.  He brought the end of his dick to my pussy lips, rubbing gently up and down, teasing my opening.  It felt great.  I was so horny I could just kill, but I also felt incredibly vulnerable and exposed and just a little bit scared, much more so than when I had presented him with my ass.  “I’ll be gentle,” he whispered.

Valerie had taken off her bra in the meantime, setting her gorgeous, perfect, big round breasts free.  Her nipples, pink and swollen, pointed almost straight out from her boobs.  For just a second, I thought about sucking on those nipples, rubbing my own breasts against those boobs, pressing my pussy against her thigh… and then Ewww!! I realized I was thinking those thoughts about my own sister!

Dave had nudged the mushroom-head of his cock in between my labia, and it felt fantastic!  My clit was screaming at me.  I was seized with an animal lust to be filled up, right now, stuffed full of cock.  His dick seemed unreasonably big between my thighs, larger than it had ever seemed before, and suddenly I was scared.

Just as I opened my mouth to tell him to go slow, Valerie smacked him across the ass with a *whack* so hard I winced in sympathy.  “Fuck her!” she hissed, “Fuck that little slut!”

Dave lurched forward, burying his meat inside me.  There was a disorienting jolt of pain as I felt my flesh tearing.  It hurt, a lot more than I had ever expected it too.  My poor pussy protested as it was rudely invaded and stretched.

I screamed.

Dave seemed to hesitate.  “Go on, fuck her!” Valerie had one hand down the front of her panties.  “Fuck that cunt!”

He started pounding in and out of my poor torn quim.  My head lolled from side to side.  I wasn’t sure I could take this.  Just as I started to protest, to tell them that this wasn’t ok, that they had to stop, the pain started to fade into the background, and the sensations of pleasure started to take over, and suddenly I didn’t want it to stop.  I wanted more!

I could feel an orgasm, a really big one, building inside me like a thunderhead.  I looked down and saw Dave’s condom-wrapped dick, streaked with my blood and come, impaling my wide-open pussy.  From the strained look of sweaty concentration on his face, I knew he must be close too.

With the hand that wasn’t busy inside her white panties, Valerie grabbed my left nipple, puling and twisting mercilessly.  It hurt, and it was pushing me over the edge.  “Fuck her harder!” she urged Dave, “Make her come on your dick!”

That was all it took for me.  I surrendered to the orgasm, bucking and thrashing on the bed, trying to raise my hips and cram more cock up my cunt as he pounded me and the most intense waves of pleasure washed through me over and over.  I think I had been screaming the whole time.

“Oh yeah,” Valerie said as I slowly drifted back to earth.  Her panties were halfway down, and her thick, curly dark bush was exposed.  She had let go of my distended nipple, but the hand between her own legs had never stopped moving.  “Come on her face!” she told Dave, “Put your sperm all over her face right now!  Come on her face or I’ll never let you touch my pussy again!”

Dave withdrew from my gasping pussy mid-stroke, ripped off the condom, sending it flying.  He scooted up the bed, red-hot dick in hand, pointed right at me.  With a wail, he shot off, squirting his hot sticky boy-come all over my face: all over my cheek, up my nose, into my eye and in my mouth.  I reveled in it.

After that, Valerie untied me, holding me close as I sobbed, asking me over and over if I was alright.  “Yes, yes, yes!” I tried to assure her.  Dave stood by, naked and depleted and looking kind of awkward and uncertain as Valerie cleaned me off and held me until the crying stopped.

“Thank you!” I was finally able to gasp, “That was amazing!”

Dave and Valerie left the room hand in hand.  I took a very hot shower, and then slept harder than I had slept in a very long time.


We never talked about what had happened.  Val and Dave dated for another couple of months before breaking it off.

Several years later, when I was deep in my militant-vegetarian-lesbian phase, and Valerie was engaged to be married, she said to me pretty much out of the blue, “Remember Dave?”

“Of course,” I said.

“He was kind of a wanker, wasn’t he?”

“Yeah he was,” I thought about it, “he was kind of a tool.”

“But he had a nice dick, didn’t he?”

“Yeah he did.  He had a very nice dick.”


( an earlier version of this story was posted at Literotica under the title ‘Valerie’)


  1. K said

    Depraved? Maybe. Slutty? Most definitely…
    The reason they’re called ‘classics’ is because they are as sinfully amazing the 100th time you read them as they were the first.

  2. ElsieFanny said

    This a great rewrite of “Valerie.” It is even better than the original, more consistent in mood, and more plausible (no proposal during the threesome), although I do kind of miss the sister incest hints from the earlier version. Thanks!

  3. Randy Swaim said

    Amazing as always. I have read this story over and over and it gets hotter each time. I’ve exploded every time I have read it. The best and most talented writer ever!!!!

  4. smutkitten said

    Wow, I think this is my favourite story of yours. I love characters like Lilly — young and innocent, full of lust and desire but still ever so slightly out of her depth. I love how long this story is and how I felt like I’d really got to know the characters. It made the sexy stuff more intense somehow!

    I loved the sound of Valerie’s novels — they’re exactly my kind of thing. Any chance you’ll feel like writing one of those, someday? XD

    • elsiewrites said

      Yes, I thought about (am still thinking about) writing a spoofy version of Valerie’s novel, and linking it, as a kind of story-within-a-story. We’ll see, one of these times. Thanks so much for the comments!

  5. John Cowan said

    It’s always worth considering whether the last line (or few lines) are worthwhile. Personally, I’d stop at “‘Of course’, I said.”

    • elsiewrites said

      I agree with you in general; but after re-reading, I still like the way I chose to end this one. I appreciate the critique though!

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