---
DISCLAIMER: This story is a work of absolute fiction based on nothing real or plausible at all. Fantasy is legal and this is all made up. Thanks for reading.And a huge THANK YOU goes out to the man, the legend, NDFakes for coming up with the cover and the bonus pictures.
---
As some of you probably know, in 2017 Lily Collins published UNFILTERED, a book of essays about her life where she talked very openly about things that women struggle with: Body image, self-confidence, relationships, family, dating, etc. The book became a best-seller and inspired thousands of young girls around the world.
I've been informed by one of my sources that, due to its success, Lily spent most of her free time throughout quarantine working on a similar project, albeit with one very important difference. This next book is all about sex. She hopes that, by talking about her past experiences in a completely honest and explicit manner, she can help other women free themselves from the stigmas surrounding sex and the female body, and that they will find the strength to embrace their own sexuality with no shame and no regrets.
The following is one of the chapters I've managed to get my hands on through my Foktonian contact.
- Noopster.
---
---
DEFLOWERING A LILY, PART 1.
This might surprise you, but I wasn't a popular girl in high school; not until my last year at least. In my first book, “Unfiltered”, I talked about how I was born in the U.K. but moved to Los Angeles with my mom when I was seven; and the transition wasn’t easy. Kids used to make fun of my accent and they would make mean comments about my eyebrows all the time, which made me very insecure and shy around people in general. That’s not to say I was a complete loner, I had a nice group of friends. But it was a small group, and I kept most of my socializing within that circle, where I felt safe. And when it came to the opposite sex, well, boys were interested in me from a very young age, but for the most part the feeling wasn't mutual. I don't know exactly why, but up to that point I had mostly been interested in friendship and nothing else. Of course I had fantasies of marrying a handsome prince and spending the rest of my life with him in a fairytale castle, just like any other girl my age, but when I looked at the boys around me, none of that seemed real, they just weren’t the charming prince type.
That was until I discovered Ryan Waller. He was the most gorgeous boy I had ever seen. He had everything a young girl could want: Blonde hair, green eyes, a chiseled jaw that made him look like he was destined to be a movie star, and the tanned, muscular body to go with it. Not only was he handsome, but he was also super popular. As the star basketball player of our school, he orbited in a different world than I did. Everyone knew who he was, whereas I tended to blend into the background. My crush on Ryan was so big that I used to stutter and blush each time he walked by my locker, even if he wasn't paying attention to me at all. So naturally, I was thinking of Ryan Waller the first time I masturbated.
As luck would have it, after a couple of years of silently fawning over him from afar, we got partnered in chemistry class by the teacher in my senior year of High School. I was so intimidated by him. We had never spoken a word to each other before and then suddenly there he was, breathing on my neck as I looked through the microscope, my voice stammering out the data for our assignment as I trembled in my chair. To him I was just another unremarkable girl acting all nervous and giddy around him, but for me, it was a mind-blowing, life-altering occasion.
After school I went home feeling like I was walking on air. I threw my things on the bed and got ready to take a bath, as was my routine, but everything seemed different that day. I put my hand behind my back to undo the clasp of my bra, and I turned to see myself in the mirror. Though not as big as I would have preferred, my breasts had a nice shape to them. They were perky and cute, and the pink shade of my nipples looked really nice opposite my pale skin. Almost immediately I thought of Ryan and what he would think if he could see them. Would he like them or would he make fun of them for their small size? I started to blush while my nipples began to harden and I brushed the tips with my fingers, feeling delicious shivers coursing through me as I explored my sensitive areolas, loving the way they reacted to the soft caress. I paused, but only to lock the bathroom door, even though I knew my mom was not back home yet. Then I returned to the mirror, fascinated by my body's reaction to my own touch. My hands went lower, first to my belly and then lower still, to the hem of my underwear. I hooked my thumbs onto the sides of my black cotton thong, taking my time to slide it down in a way I had never done before, surprised by how the crotch clung to my virgin lips for a moment before letting go. I looked at myself for a while as I stood there completely naked, it was the first time I had looked at my own body trying to see it as someone else would; as a boy would. More specifically, as Ryan Waller would. I remember feeling a little guilty as I stared at my vagina, my fingers spreading it wide, imagining what it would be like to show it to someone, the idea that it was forbidden only making me feel warmer and more daring.
Down on the floor, the crotch of my thong was clearly wet, and as I carefully prodded into my opening, I felt a current coursing through me, and realized just how moist and sticky it was down there. The events of chemistry class had awakened a curiosity about my own body and what it could do. Not just for me, but for others too. I thought I was too young to be having those kinds of thoughts, but the more I tried to push them away, the more I found myself lured by the idea that Ryan Waller should be my first. Ryan was not a virgin, the school knew of his escapades with the popular girls, so it was imperative that before we could be together, I got to know myself intimately, so that I could be close to his level when we did. In my young, naive mind, the fact that he hadn’t talked to me the 3 years of high school before barely mattered because now he knew I existed, he knew my name, and destiny would surely take care of everything else.
I turned to check my backside in the mirror. My bottom was well rounded and my thighs nice and full, tapering down to well-shaped calves and petite feet. I felt pretty and ready for more. I sat on the toilet before the big mirror, spreading my legs, then spreading my lips, trying to get a good glimpse of my hidden treasure. I stared at my pink opening for a while, trying to imagine what it would be like to have something or someone going inside of it. Then I gingerly inserted a finger inside myself, thinking about Ryan as I started to feel my way around. It wasn't long before I started to moan as my fingers brushed the nub at the top of my slit. I had been brought up under the assumption that good girls were not supposed to think sexual thoughts, that it was something dirty to be avoided, but on that day curiosity and pleasure overrode the guilt, and soon my fingers drummed up a steady rhythm around my clit.
I looked at my image in the mirror while I continued playing with myself and it was like I was watching someone else. The tiny, pale girl in the mirror with her legs spread wide open and a finger in her pussy, mouth half open in a silent moan...that could not be me. 'If Ryan could see her now...' I said to myself as I pushed my fingers in and out of my vagina, which kept growing wetter with every ingress. It wasn't long before I felt my abdomen throbbing and the convulsions of my very first orgasm coming on. I remember feeling scared of what I was feeling for a few seconds; those feelings were completely novel to me and I didn't know what to do with them, but I couldn’t stop so I kept on going, kept pushing my fingers deeper as my body tensed up and suddenly everything went beyond my control, sending me into the throes of rapture.
I felt like I had died and gone to heaven as all of that incredible pleasure washed over me, and when it ended I pulled my fingers out and marveled at the way they glistened with my own arousal as I leaned back, completely spent, enjoying the sensations, my heart beating wildly, my breath ragged and heavy.
I started to become aware of my surroundings again as my breathing slowly returned to normal and I noticed the blush spread across my pale reflection in the mirror. My mother would be returning soon, so I stood up, my legs wobbling as I placed my hand under my pussy, now sopping wet, and felt a shiver run through me again before I carefully stepped into the shower to clean myself. The warm water invigorated me, and as I closed my eyes, reveling in the sensations, Ryan's image came back to me. I started to imagine him caressing my entire body, kissing me softly at first, like they did in the movies, before holding me close and taking me in his strong arms. My body responded to the new stimulus, and as my fantasies became more graphic, I started thinking about the time I’d found a pornographic magazine in one of my Dad’s drawers. I must have been 13 or 14 at the time, and the photos of a busty secretary kneeling in front of her boss with his penis in her mouth had shocked me to the core, enough to keep me from snooping around in my father’s belongings ever again. The memory of that woman kept flashing in my mind as I stood there playing with myself. I parted my lips and sucked on the same two fingers I had put inside of me, sucking on them as if I was that secretary and my fingers were that man’s member. With my free hand I began to contour my neck, cupping my breasts, playing with my stiff nipples, moaning openly now as I pinched and pulled them. And then the movie in my head changed, it was Ryan's manhood I was sucking on now, imagining myself on two knees, pleasuring him with nothing but my mouth. Then my hand moved down my belly, finding the nub of my clit again, extra sensitive to the touch after having already orgasmed once. I knew my mom would be coming home soon but I couldn’t stop moaning. My legs splayed wider as the soap and warm water aided my fingers in penetrating deep between my tender inner walls and just as I thought of Ryan finishing inside my mouth, like the man in the magazine had, I felt myself climaxing once more and sank down to the shower floor as my legs gave way and the waves of pleasure washed over me, moaning Ryan’s name over and over again.
I was just getting my breath back when there was a knock on the door, and my mother calling out my name. "I'll be out in a moment!" I said, opening my eyes to take stock of myself, sprawled on the shower floor, realizing just how long I had been there and praying that she had not heard me.
---
The next day at school was a strange one for me. I almost felt like a different person after those two amazing orgasms; less an inexperienced girl, more of a woman. And even though I was the only one that knew, I was walking with more confidence, feeling more assertive in my interactions with others. And from that day on, I started looking at Ryan differently during chemistry class. It felt like I knew him intimately now, like we had shared something special together, even though it all had taken place in my mind. Chemistry class became my reason for being. Ryan was so charming and sweet that I found myself falling even more for him as I got to know him a little more, and I kept trying to memorize every little thing about him so I could conjure it later in the privacy of my bathroom. The veins in his arms, the cut of his jaw, the flow of his hair. I was head over heels for him, and from that point on touching myself after school to the thought of him became a steady part of my routine.
Sometimes I would fantasize about us having sex, and sometimes I would imagine myself going down on him. And yet, I had no idea what it was like to actually do any of those things. I had never even seen a penis aside from that incident with my Dad’s magazine, Biology textbooks or a quick glance from one of the blurry 240p videos people had on their phones at the time. Eventually, after a couple of months of doubting myself, curiosity got the best of me, and I did what every teenager usually does in that situation. I searched the internet for porn.
I remember how intimidating it was to click on those shady, seedy sites, entering a world I knew nothing about. I didn't even click on anything at first, I would just scroll down and get intimidated by looking at the thumbnails of well-endowed men having sex with big buxomed women who looked nothing like me. But eventually, I stumbled upon a "teen" site, and everything changed. A lot of the girls in the thumbnails looked like me. Pale skin, brown hair, slight frame. That made the sex feel less intimidating and more real. It gave me the courage to finally go all the way and finally click on one of the thumbnails that took me to a gallery. I clicked on the first photo and it blew up on my screen. I will never forget that image. A young, innocent-looking girl, not much older than me and more on the side of cute than hot, small breasts too, same as me. She was leaning over an older man, who must've been in his 40s by the looks of it, and her hand was wrapped around his huge, veiny member. The sight of that immediately fascinated me. I looked at my own hand and it looked just like hers. Was that what it would look like if I was grabbing Ryan's penis? Surely he couldn't be that big, although in my innocence I kinda hoped that it would because bigger had to be better, right?. Suffice it to say that adult Lily would eventually learn that’s not always the case; but that’s a story for another chapter.
I was mesmerized by those pictures of that young girl handling that huge, swollen organ, and oh was it making me so horny. I then noticed the handjob tag below the picture and decided to focus my research on that for the time being, since anything else was still too intimidating. I must've watched half a dozen short videos of young girls pleasuring older men with nothing but their hands, closely studying the way they jerked and caressed, using one hand sometimes, using both some other times. And I would touch myself, trying to make myself orgasm just as the man in the video exploded all over her. I even went as far as to practice with a cucumber, just so I could pretend it was the real thing as I did my best to imitate what I saw on screen. I know what you must be thinking, did I ever do anything else with that girthy vegetable? The truth, unexciting as it might be, is that I did try it and couldn’t go through with it. One particular day I got home feeling extra motivated after having watched Ryan during gym class, I put that cucumber against my entrance and felt the shivers running through my body as the tip made its way inside, but the second I felt the girth starting to stretch me I got scared and chickened out, choosing to finish myself with my finger instead.
As luck would have it, Ryan and I got paired up by the teacher again that same week for a special project. I was a straight As student and he was… well, more athletically inclined. I had told my mom about him and knew that if we went to my place she would likely embarrass me by asking all sorts of questions and putting me on the spot, so I suggested we do the project at his house instead.
Ryan's dad worked nights so by 6 PM he was gone. It was the first time I had gotten to talk to him outside of school and I was so nervous to be alone with him, but I was pleasantly surprised at how down to earth and nice he actually was. His dad was divorced and so was my mom so we had that in common, and now that he was away from all the popular kids at school he didn’t seem like a golden God, just a normal person that happened to look like a golden God. That's not to say I had stopped being in awe of him, if anything I was feeling even more attracted to him than ever before. He was still gorgeous and confident and charming as hell, but I was starting to fall in love with what I thought was the real Ryan, the one most people never got to see.
An hour passed, then another one, and we started getting more comfortable with each other as the night went on. At one point he had to excuse himself because it was time to put his little brothers to bed and I thought that was the sweetest thing ever. I just could not keep my eyes off of him, even to the detriment of our science project. And then the most amazing thing happened as I was leaning over the table to reach for a marker. I somehow felt his eyes on me and when I looked back I saw that he was checking out my butt. I had picked a pair of jeans that were especially form-fitting around my posterior, and checked myself in the mirror a thousand times before leaving home to make sure the white button-up shirt looked good with them.
I had even snuck out a pair of my mother’s high heels, hiding them in my bag so she wouldn’t see them and putting them on right before I rang Ryan’s doorbell; all for a school project. My feet were already killing me but it had definitely worked, I could see it in his eyes.
I couldn't believe it. Me, the girl with the bushy eyebrows, getting Ryan Waller's undivided attention. I felt myself blushing and when he saw that I had caught him he just smiled in this incredibly charming way that would've disarmed me completely if not for the fact that I had already been under his spell for years.
"Sorry, I... couldn't help it," he said as I straightened up.
"No, it's fine, really, I'm... flattered," I replied, stumbling over my own words, feeling my face turning red, not knowing what to do with my hands and fearing my head was about to explode.
"It's just that..." He took a step towards me, "You look really hot tonight."
"I... I do?" I said, shaking.
"Yeah, I guess I never noticed before how pretty you are."
By this point he was almost on top of me, my body pinned between his and the dinning table. I felt him lean on me and in an instant, his broad chest pressed against my small breasts as he kissed me very gently on the lips. I was shocked and only managed to blurt out an awkward "Thank you" before returning the kiss. He ran his hand through my hair and broke our kiss so he could look into my eyes. It wasn't just any look, it was a lover's look, although looking back on it now I realize it was more like he was sizing me up, making sure I was under his spell before going in for the kill. I totally was, of course, and he knew it, but at the time I thought that was true love burning in his eyes. "W--what?" I stuttered, trembling uncontrollably. He smiled, his emerald eyes piercing my soul. Slowly, he ran the tip of his fingers from my lips down my body. My neck, between my breasts, creating a trail down my abdomen until they reached right under my belly button. Low rise jeans were in fashion at the time and he caressed the exposed skin right above my pubis, tickling me a little before deftly undoing the button and slipping his hand under the waistband.
It seemed to be happening in slow motion, Ryan Waller’s hand in my pants, going down between my legs, where no one else but me had been before. He ventured further down, his fingertips brushing over my short trimmed pubes. I was so nervous, but my body was aching to be touched. He continued further down and when I felt the tip of his fingers brush my lips I gasped and my hips moved forward on their own, inviting him to continue. I remember holding on to the edge of the table, my knees shaking from pure excitement as his finger teased my pussy lips while he looked straight at me. "R--Ryan," I began to say. I don't know what was going to follow because right then his finger found my entrance and slipped inside of me. A rush of blood to the head froze me and I leaned my body back and pushed my hips further forward so he could really slide all the way into me. His free hand came up, unzipped me and hastily pulled my jeans down to my knees.
Before leaving home that day, as I was picking my outfit, it had taken me a long time to decide on what kind of underwear I’d be wearing. And I never actually believed he’d be in a position to see them, much less pull them off me, but I wanted to feel confident and sexy in everything I had on me, so I'd picked a pair of white lace bikini panties that I had bought without my mom knowing.
I was terrified. Suddenly my little bush was in full view, right there in his family’s kitchen. I felt my whole face turning red, things were moving so fast I felt like I could do nothing but watch as that finger moved inside of me. Don’t get me wrong, I was scared of the moment, not him. Despite all the time I had spent dreaming about that moment, I was still not even close to being ready to go through with it. And yet, the way he was taking charge was making me feel not only aroused, but reassured somehow that this needed to happen. After all those times I had pleasured myself thinking of him, now Ryan Waller himself was the one doing it for me. As I folded in his hands, I told myself that it had to be fate and we were destined to be together. It was too perfect not to be true.
I was trying to keep up with his tongue thrashing around in my mouth when he pulled back to put two fingers inside of me. I had never felt anything like it, the closest I had gotten was that cucumber, and as I mentioned before, I had bailed on it at the last second. But I was under Ryan’s spell and his thick fingers were pushing all the way inside of me, making my knees buckle as I moaned his name lightly on his lips.
He must've liked that, because he went from slowly massaging me to pistoning his fingers in and out without any caution. I didn't know any better, I figured that was just how guys did it, so I bit my lip and took it, tilting my head back as he kissed up and down my neck, the initial pain being replaced by the electric build-up of pleasure I had grown accustomed to in my bathroom, but greatly intensified by Ryan's presence. I felt myself getting wetter, more than I thought was possible and, in complete disregard for his little brothers sleeping in the next room, I started moaning louder and louder. I threw caution to the wind as Ryan started pulling at the buttons on my shirt, telling myself it was okay because he was the love of my life, so I helped him open them before he pulled one of the cups on my girly white bra down and latched his mouth around my breast. That was the greatest thing that had ever happened to me and I held his head and pulled him closer, loving the way his tongue ran in circles over my aroused nipple as I continued to moan and push my hips against his wrist. I remember feeling the cold edge of the wooden table digging into my bare bottom and thinking how wrong it was to be there naked in his dining room, even as I begged him not to stop.
At that point he must've known he had me, because he pulled the other cup of my bra down before just ripping the whole thing off of me. I barely had time to gasp before he was on my other breast, squeezing and sucking, clamping his lips and pulling on my hardened nipple while he continued pumping his finger in and out - his fingers all the way in now, in and out, relentlessly.
"Yes, yes, yes!" I eventually started screaming, loud enough that, in retrospect, there was no way his siblings didn't hear me. I lost control of myself; I forgot everything my mother had taught about how a proper young lady should act and openly begged him to make me cum. Suddenly, I felt my pussy gripping his fingers tightly and it took every last bit of self control in me to keep myself from crying in ecstasy as a wave of pleasure washed over me. I felt Ryan holding me with one strong arm as his fingers continued to slip in and out of my quivering pussy, and myself gushing all over it while I hugged him tightly and moaned into his shoulder.
Now that I’m older I understand that was nothing but a young girl’s crush, but in that moment, as I held on to him and felt his fingers slowing down, I thought what I was experiencing was true love; and I wished we could stay like that forever. In all honesty and after all the things I’ve experienced since, there still are times I wish I could return to that blissful ignorance, when life was simpler and having a cute boy’s fingers inside of me was a life-altering moment.
And then, as soon as I started coming back to earth, a wave of shame came over me when I realized I had just come on his hand, in his dining room, with his two brothers sleeping in the next room. I didn't know what to say or how to act as I started to compose myself. I remember stuttering something after he removed his hand from between my legs and then an impish smile on his face as he looked at my wetness all over his fingers. I looked at his hand too and right below it, his fully erect penis, under his jeans. I really wanted to touch it, to feel it in my hand, but this was our first time hanging out and I had already crossed so many lines, I was terrified of what he would think of me if I did. I was trying to come up with something to say, anything to make the moment less awkward, and then I watched him slowly raise those wet fingers and bring them to my face, giving me enough time to see how they glistened from up close before he said to me, "Lick them."
"Wh--wh--what?" I stuttered like an idiot.
"Come on, give ‘em a lick," he replied.
My mind was racing. Was that something boys wanted to see? I had no idea, I wasn't sure if he was joking or messing with me, but then he pressed those fingers to my lips and I felt the warmness of my own sex and smelled my own arousal. I was so embarrassed, but seeing his delighted reaction after I stuck out my tongue and licked one of his fingers made me feel amazing, so sexy and grown up (or so I thought at the time). I became more daring and made a point of slowly dragging my tongue from his knuckle to the tip, holding back a giggle as I watched his face contort into an expression of pure, unbridled lust. It was so incredibly exciting to realize I could have that effect on someone, especially him. Ryan Waller, losing his cool because of me, completely captivated by me, hard as a damn rock for me. I felt like I was floating, and not just because I had just had the best orgasm of my life, but because it seemed like all my dreams and fantasies were finally coming true.
"You're so fucking hot," he said to me before he pushed those two fingers deep into my mouth. I was happy to let him do it, happy to close my lips around them and taste myself, happy to look him in the eye as he pushed them in and out of my mouth, the same way he’d done with my pussy, even if I didn't quite understand what he was preparing me for.
Finally, he pulled them out and kissed me again. I could feel his hard penis, still trapped in his shorts, poking my navel and his hand squeezing my butt cheek as he said to me, "Let's go to my room." I was about to say yes, and this story would've been completely different, if not for the fact that my mom decided to call me right at that moment. The phone ringing startled me and I jumped in his arms. I didn't answer, of course, I wasn't even close to being in the right mental state for that, but just seeing her name on the screen was enough to bring me back to my senses. What the hell was I doing? Letting some boy in my class who I hadn't even gone on a date with finger me? Even if he was my future husband and we were destined to be together, letting him take me to his room so soon did not fit with the romantic ideal I’ve built up in my head. I told myself that was not how my mother had raised me and, after gathering all of my courage, I politely declined. I told Ryan things were moving too fast for me and asked if he could take me home. It was very evident he was not thrilled but, to his credit, he was a perfect gentleman about it. He didn't get angry, he didn't pressure me, he just said, "Okay," and drove me home.
Except, that's not the whole story, dear reader. I was about to do something a little bit dumb and a little bit reckless that would end up shaping the rest of my high school experience as well as my interactions with men for years to come.
---
You see, the ride home was super awkward. As he was driving me home I had started to feel embarrassed that I had chickened out. Everyone at school knew that Ryan hung out with college girls on the regular. He was accustomed to being with women who were older, hotter and way more experienced and sophisticated than I could ever hope to be at that age. Girls that were cool and didn't have muppet eyebrows like me. Meanwhile, I was the dorky girl reading Harry Potter books during lunch who, for some reason I still couldn't figure out, had actually gotten the attention of the hottest, most popular guy in school; and I had rejected him! Me, the virgin who had been fantasizing about him for years, dreaming of the day he would finally say something to me across the hall, pleasuring myself almost daily while thinking about him… about my first time being with him... that same girl had panicked and asked him to take her home like a total loser when she could have had the thing she desired most.
Obviously I realize now just how immature those thoughts were, and let me be clear that all women (especially young teenage girls like I was) should always have the right to say No at any point, but back then I didn't know what I do now. 'He must think I'm an idiot' I kept thinking, 'He'll probably never want to talk to me again'. I started imagining what it would be like at school the next day, with him avoiding me or worse, telling the other kids that I was both a tease and a prude. By the time we parked outside my house, I was completely freaking out.
"We're here," he said with a very distant, almost emotionless tone. I turned to him and thanked him, but something took over me as I leaned in. All I knew was that if I said good night and got out of the car, I would regret it for the rest of my life, so instead of kissing him on the cheek I went for the lips. I put my hand on his thigh and realized he still had an erection right before he kissed me back. He was still into me, I still had an opportunity! That was all that I needed, I decided to go for it right then and there and my hand moved to his crotch. I held his penis in my hand and it was incredible. Even with his pants still in the way, all I could think of were the girls in those videos, and how my fantasies were finally coming true. I felt him getting harder as our tongues wrestled and I was ecstatic, it didn't even matter that we were parked right outside my house, that my mom or one of the neighbors could catch us if they looked our way, all that mattered was that he still liked me and that my silly white wedding dreams were still possible. So I kept going, pawing at his penis while he helped me unzip him. I took it out of his boxers and found that it wasn’t as big as some of the ones I had seen in those pornos, but it certainly wasn’t small, and more importantly, it looked so swollen and juicy, twitching in my palm as I wrapped my fingers around it. He forced his hand inside my blouse and a couple of the buttons popped off, but I didn’t care, too excited and frantic about the fact that I was touching his penis for the very first time. Oh his big, strong fingers clenching around my small breast had me moaning in his mouth right away and my little hand tightened its grip on his hard, warm cock. I gave it a little squeeze, and saw the clear droplet appearing at the slit, his precum plainly visible thanks to the bright street lights coming through the driver’s window. Fascinated by this, I leaned closer, getting a good look at the tip, and inhaling the scent of his manhood while his other hand slipped into the back of my pants to grab my butt. Still curious, I reached out with my index finger and tapped at the slit opening. Ryan hissed, reacting to that sudden pleasurable sensation, and as I lifted my finger, the fluid stretched up, clinging to my fingertip as well as his slit. I loved it so much, I wanted to play with it like that for a longer time, familiarize myself with every vein and bump, but then I remembered where we were.
I looked around us, the lights inside my house were off and the curtains were drawn, the street seemed completely empty... I was going for it. For all the shame and fear of getting caught, my pussy was still burning. The sensation of Ryan's fingers inside me had left me just wanting more and, as mortifying as it was to be doing that in front of my own house, with my mother just a few feet away, I was actually shocked at just how irresistible the impulse to keep going was. And so, with half his right hand in my butt crack and the other one pawing at my breasts, I began to stroke him, my face moving closer and closer to his crotch as if pushed by an invisible force. His cock was pointing straight out, pointing at my face, and I eventually got close enough to let it touch my cheek. "Umm," he moaned and I smiled to myself while I felt its warmth and hardness on my face, and the wet precum that stuck to my skin. I was like a little kitten rubbing myself on a foreign object when he pulled his hand out of my pants and put it on top of mine, aiming the tip of his penis at my mouth. I saw there was another drop of precum beginning to ooze its way out of the eye as he held his cock and I hesitated. I had only watched handjob videos up to that point, I had no idea what giving oral sex was supposed to be like.
"Come on, what are you waiting for?" he said to me. Not the most romantic of lines, I know, but in that moment it did have the desired effect on me. I was already there, kneeling on the seat with my butt in the air, holding his penis in my hand, risking getting caught... What was I waiting for?
I stopped waiting and finally opened my mouth and stuck out my tongue so I could lick the moisture off the tip. "Ohhhh yeah," he sighed, and the way he said it, so full of relief, made me open my mouth wider. I let him push it in. His cock was warm, thick, and almost pulsing. I didn't know what I was doing so I just licked around the underside as he began to slide it in and out ever so gently, carefully fucking my mouth with his cock, something I’d never even heard about before. I felt so dirty, but also a little relieved that he had taken the lead so I wouldn't embarrass myself by doing a poor job.
"Ohhh yeah, Lily, ooohhh shit, Lily," I heard him saying, and knowing that he was enjoying it and repeating my name like that turned me on so much that I almost didn't notice the car passing by until it was right next to us. It was probably going too fast to notice us, and there's no way they could've seen me while I was down there in his lap, but I still felt a rush of shame for doing something like that right on the street like some kind of hooker. 'Am I a skank? This isn't what proper young ladies do,' I kept telling myself as he continued using my mouth. But even as these thoughts crept into my mind, his cock between my lips just felt so right and helped to ease my doubts.
"Oh yeah, Lily, oh yeah, just like that."
Wanting to impress him, I copied a move from the handjob videos I had seen and cupped his testicles, gently squeezing them while the spit from my mouth covered them and my fingers. We spent I don’t know how long like that, Ryan moaning and thrusting into my mouth, and me doing my best to keep myself from falling while I let him use my mouth as he needed to, hoping he’d explode just like in the videos.
"Ohhhh, Lily, FUCK! I'm gonna cum, I'm gonna cum soon!" he told me just as another car went past us, and I started getting scared again that someone would see us; the thought of my mom finding out shaming me to no end. And yet as I felt him throb, I wanted him to finish, to help him feel as good as he had made me feel in his kitchen. But more than that, I wanted him to know that I wasn't just a tease, that I was just as cool as the other girls he usually hung around with.
"That's it, that's it. Ooohh, yeah, suck my cock, Lily, suck it!" he said, grabbing the back of my head and thrusting it down to his cock, ramming it deeper into my mouth. I felt a mix of shame and excitement at his words. I wasn't doing any actual sucking, he was pretty much doing all the work himself, but I still loved hearing him saying my name like that, the same way I had heard the men talk in those videos I had been secretly watching.
"Fuck, I'm gonna cum, fuck, fuck, FUCK!"
His thrusting became more urgent and his cock started hitting the back of my throat. I didn't enjoy that part of it to be perfectly honest, but I knew that soon he was going to finish so I hung in there, trying my best not to ruin the experience for him. ‘Ryan Waller is going to cum in my mouth! Ryan Waller is going to cum in my mouth!’ I kept telling myself, as if I had just won some strange lottery, and even though I had no idea what that would feel like, I still wanted it so bad.
It didn’t take long for my wish to come true, but right before he came, Ryan made the strangest sound. It was this raspy, drawn out groan, like something invisible had just wounded him. I’ve been with many men since and I feel like I’ve seen and heard it all at this point, but that was my first time seeing and hearing a man achieving climax in real life, and it freaked me out so much that I started to fear that somehow I had done something wrong.
When I think about it now it’s so funny to me just how terrified I was of doing “a bad job”, as if pleasuring a man wasn’t the easiest thing in the world. But of course I didn’t know that then, and when he all of a sudden tensed up and I felt the first blast of semen hit the back of my throat, I audibly gasped and instinctively recoiled. None of the clips I had been watching in secret had prepared me for how powerful his ejaculation was, and just as it slipped out of my mouth, Ryan held me there and the next spurt hit the top of my forehead. It was a shocking sensation and it was happening so fast, but somehow I realized that getting cum on my hair would not be a good thing once I had to face my mom, so I tilted my head so that the head of his cock was pressed against my cheek to keep it in check somehow. I remember feeling the force of it pumping under my thumb, shooting sperm all over the side of my face and Ryan sighing loudly as he neared the end. He pulled his cock from my grasp and jerked it himself as I watched the last white drops splashing onto my forehead, my eyebrow, my lips.
When he was done, I had cum running down the entire left side of my face. I could feel some of it stuck to my lashes, and a thick wad dangling from my chin as I started looking around for something to wipe it down with.
"Oh honey, your makeup is all runny! Have you been crying? Is everything okay?"
"Uh, yeah, I just-- I was watching a really sad movie."
"Movie? But I thought you were gonna work on a school project?"
"Yeah, yeah, we, uh, finished early."
I closed my bedroom door behind me and let out the biggest sigh of my life. I was still so full of adrenaline that instead of going to bed I spent the next few hours reliving everything. After all those months rehearsing by myself in the bathroom, I had gotten my first real sexual experience with a boy. And not just any boy, Ryan Waller, the boy I had had a crush on for so long, he had been in my mouth, he had made me cum with his fingers, and he had cum between my lips, his taste still fresh on my tongue. Even though the night had ended on a weird note, I still felt like the luckiest girl in the world. I felt such power at having made him cum that I couldn’t keep myself from running my hands over my face, trying to re-experience the feel of his seed all over my face, remembering the smell and the taste and the texture for God knows how long, until I realized I still had to finish the damn science project.
I told myself that having to stay up late doing homework was a small price to pay for what had just happened between Ryan and me and right away I started dreaming about what the next day at school would be like. There was a connection between us, I was so sure. He’d didn’t just tell me I was pretty, he'd said I was “fucking hot”. No one had ever said that to me. Surely after that-- and everything else that had happened in his car-- he would have to ask me to be his girlfriend. I was beaming. Me, the dorky girl with the bushy eyebrows, I was about to be Ryan Waller's girlfriend.
I was freaking out, even after I’d finished the assignment I still couldn't sleep. I laid in bed, touching myself to the fresh memories of Ryan’s cock in my mouth, and I knew that my high school life was about to change forever. But I never would have guessed exactly how.
---
I can’t help but laugh and cringe at myself when I think about it now. I was so innocent and clueless that it never crossed my mind that what had happened could be anything but the beginning of a beautiful, movie-like romance, when in reality I’d just had my first experience with casual sex. The first of many, as you will discover in later chapters of this book. But let me make it clear for all my young readers out there, casual sex can be incredibly fun and satisfying when it’s between two consenting adults that understand it’s all about pleasure and living in the moment. When you’re young and you don’t really know what you’re doing, I believe it’s best to make sure you’re doing it with someone who you know you can trust, someone who’s proven to be worthy of that trust and not just the popular guy at school.
And that’s a lesson I learned with Ryan every step along the way.
END OF PART 1.
As some of you probably know, in 2017 Lily Collins published UNFILTERED, a book of essays about her life where she talked very openly about things that women struggle with: Body image, self-confidence, relationships, family, dating, etc. The book became a best-seller and inspired thousands of young girls around the world.
I've been informed by one of my sources that, due to its success, Lily spent most of her free time throughout quarantine working on a similar project, albeit with one very important difference. This next book is all about sex. She hopes that, by talking about her past experiences in a completely honest and explicit manner, she can help other women free themselves from the stigmas surrounding sex and the female body, and that they will find the strength to embrace their own sexuality with no shame and no regrets.
The following is one of the chapters I've managed to get my hands on through my Foktonian contact.
- Noopster.
---
DEDICATION
For all those who have ever felt ashamed of the things they enjoy…
To the incredibly beautiful young men and women around the world whom I hope will be inspired to be open to new experiences and to explore every aspect of their sexuality. And to all those that have shared a moment of intimacy with me and helped me discover myself along the way, thank you for your encouragement, your passion and affection, and for all the pleasure you’ve given me. Your willingness and enthusiasm to bare your body and soul has inspired me to do the same.
Love Always and Forever.
For all those who have ever felt ashamed of the things they enjoy…
To the incredibly beautiful young men and women around the world whom I hope will be inspired to be open to new experiences and to explore every aspect of their sexuality. And to all those that have shared a moment of intimacy with me and helped me discover myself along the way, thank you for your encouragement, your passion and affection, and for all the pleasure you’ve given me. Your willingness and enthusiasm to bare your body and soul has inspired me to do the same.
Love Always and Forever.
---
DEFLOWERING A LILY, PART 1.
This might surprise you, but I wasn't a popular girl in high school; not until my last year at least. In my first book, “Unfiltered”, I talked about how I was born in the U.K. but moved to Los Angeles with my mom when I was seven; and the transition wasn’t easy. Kids used to make fun of my accent and they would make mean comments about my eyebrows all the time, which made me very insecure and shy around people in general. That’s not to say I was a complete loner, I had a nice group of friends. But it was a small group, and I kept most of my socializing within that circle, where I felt safe. And when it came to the opposite sex, well, boys were interested in me from a very young age, but for the most part the feeling wasn't mutual. I don't know exactly why, but up to that point I had mostly been interested in friendship and nothing else. Of course I had fantasies of marrying a handsome prince and spending the rest of my life with him in a fairytale castle, just like any other girl my age, but when I looked at the boys around me, none of that seemed real, they just weren’t the charming prince type.
 |
| High School me. |
As luck would have it, after a couple of years of silently fawning over him from afar, we got partnered in chemistry class by the teacher in my senior year of High School. I was so intimidated by him. We had never spoken a word to each other before and then suddenly there he was, breathing on my neck as I looked through the microscope, my voice stammering out the data for our assignment as I trembled in my chair. To him I was just another unremarkable girl acting all nervous and giddy around him, but for me, it was a mind-blowing, life-altering occasion.
After school I went home feeling like I was walking on air. I threw my things on the bed and got ready to take a bath, as was my routine, but everything seemed different that day. I put my hand behind my back to undo the clasp of my bra, and I turned to see myself in the mirror. Though not as big as I would have preferred, my breasts had a nice shape to them. They were perky and cute, and the pink shade of my nipples looked really nice opposite my pale skin. Almost immediately I thought of Ryan and what he would think if he could see them. Would he like them or would he make fun of them for their small size? I started to blush while my nipples began to harden and I brushed the tips with my fingers, feeling delicious shivers coursing through me as I explored my sensitive areolas, loving the way they reacted to the soft caress. I paused, but only to lock the bathroom door, even though I knew my mom was not back home yet. Then I returned to the mirror, fascinated by my body's reaction to my own touch. My hands went lower, first to my belly and then lower still, to the hem of my underwear. I hooked my thumbs onto the sides of my black cotton thong, taking my time to slide it down in a way I had never done before, surprised by how the crotch clung to my virgin lips for a moment before letting go. I looked at myself for a while as I stood there completely naked, it was the first time I had looked at my own body trying to see it as someone else would; as a boy would. More specifically, as Ryan Waller would. I remember feeling a little guilty as I stared at my vagina, my fingers spreading it wide, imagining what it would be like to show it to someone, the idea that it was forbidden only making me feel warmer and more daring.
Down on the floor, the crotch of my thong was clearly wet, and as I carefully prodded into my opening, I felt a current coursing through me, and realized just how moist and sticky it was down there. The events of chemistry class had awakened a curiosity about my own body and what it could do. Not just for me, but for others too. I thought I was too young to be having those kinds of thoughts, but the more I tried to push them away, the more I found myself lured by the idea that Ryan Waller should be my first. Ryan was not a virgin, the school knew of his escapades with the popular girls, so it was imperative that before we could be together, I got to know myself intimately, so that I could be close to his level when we did. In my young, naive mind, the fact that he hadn’t talked to me the 3 years of high school before barely mattered because now he knew I existed, he knew my name, and destiny would surely take care of everything else.
I turned to check my backside in the mirror. My bottom was well rounded and my thighs nice and full, tapering down to well-shaped calves and petite feet. I felt pretty and ready for more. I sat on the toilet before the big mirror, spreading my legs, then spreading my lips, trying to get a good glimpse of my hidden treasure. I stared at my pink opening for a while, trying to imagine what it would be like to have something or someone going inside of it. Then I gingerly inserted a finger inside myself, thinking about Ryan as I started to feel my way around. It wasn't long before I started to moan as my fingers brushed the nub at the top of my slit. I had been brought up under the assumption that good girls were not supposed to think sexual thoughts, that it was something dirty to be avoided, but on that day curiosity and pleasure overrode the guilt, and soon my fingers drummed up a steady rhythm around my clit.
I looked at my image in the mirror while I continued playing with myself and it was like I was watching someone else. The tiny, pale girl in the mirror with her legs spread wide open and a finger in her pussy, mouth half open in a silent moan...that could not be me. 'If Ryan could see her now...' I said to myself as I pushed my fingers in and out of my vagina, which kept growing wetter with every ingress. It wasn't long before I felt my abdomen throbbing and the convulsions of my very first orgasm coming on. I remember feeling scared of what I was feeling for a few seconds; those feelings were completely novel to me and I didn't know what to do with them, but I couldn’t stop so I kept on going, kept pushing my fingers deeper as my body tensed up and suddenly everything went beyond my control, sending me into the throes of rapture.
I felt like I had died and gone to heaven as all of that incredible pleasure washed over me, and when it ended I pulled my fingers out and marveled at the way they glistened with my own arousal as I leaned back, completely spent, enjoying the sensations, my heart beating wildly, my breath ragged and heavy.
I started to become aware of my surroundings again as my breathing slowly returned to normal and I noticed the blush spread across my pale reflection in the mirror. My mother would be returning soon, so I stood up, my legs wobbling as I placed my hand under my pussy, now sopping wet, and felt a shiver run through me again before I carefully stepped into the shower to clean myself. The warm water invigorated me, and as I closed my eyes, reveling in the sensations, Ryan's image came back to me. I started to imagine him caressing my entire body, kissing me softly at first, like they did in the movies, before holding me close and taking me in his strong arms. My body responded to the new stimulus, and as my fantasies became more graphic, I started thinking about the time I’d found a pornographic magazine in one of my Dad’s drawers. I must have been 13 or 14 at the time, and the photos of a busty secretary kneeling in front of her boss with his penis in her mouth had shocked me to the core, enough to keep me from snooping around in my father’s belongings ever again. The memory of that woman kept flashing in my mind as I stood there playing with myself. I parted my lips and sucked on the same two fingers I had put inside of me, sucking on them as if I was that secretary and my fingers were that man’s member. With my free hand I began to contour my neck, cupping my breasts, playing with my stiff nipples, moaning openly now as I pinched and pulled them. And then the movie in my head changed, it was Ryan's manhood I was sucking on now, imagining myself on two knees, pleasuring him with nothing but my mouth. Then my hand moved down my belly, finding the nub of my clit again, extra sensitive to the touch after having already orgasmed once. I knew my mom would be coming home soon but I couldn’t stop moaning. My legs splayed wider as the soap and warm water aided my fingers in penetrating deep between my tender inner walls and just as I thought of Ryan finishing inside my mouth, like the man in the magazine had, I felt myself climaxing once more and sank down to the shower floor as my legs gave way and the waves of pleasure washed over me, moaning Ryan’s name over and over again.
I was just getting my breath back when there was a knock on the door, and my mother calling out my name. "I'll be out in a moment!" I said, opening my eyes to take stock of myself, sprawled on the shower floor, realizing just how long I had been there and praying that she had not heard me.
---
The next day at school was a strange one for me. I almost felt like a different person after those two amazing orgasms; less an inexperienced girl, more of a woman. And even though I was the only one that knew, I was walking with more confidence, feeling more assertive in my interactions with others. And from that day on, I started looking at Ryan differently during chemistry class. It felt like I knew him intimately now, like we had shared something special together, even though it all had taken place in my mind. Chemistry class became my reason for being. Ryan was so charming and sweet that I found myself falling even more for him as I got to know him a little more, and I kept trying to memorize every little thing about him so I could conjure it later in the privacy of my bathroom. The veins in his arms, the cut of his jaw, the flow of his hair. I was head over heels for him, and from that point on touching myself after school to the thought of him became a steady part of my routine.
Sometimes I would fantasize about us having sex, and sometimes I would imagine myself going down on him. And yet, I had no idea what it was like to actually do any of those things. I had never even seen a penis aside from that incident with my Dad’s magazine, Biology textbooks or a quick glance from one of the blurry 240p videos people had on their phones at the time. Eventually, after a couple of months of doubting myself, curiosity got the best of me, and I did what every teenager usually does in that situation. I searched the internet for porn.
I remember how intimidating it was to click on those shady, seedy sites, entering a world I knew nothing about. I didn't even click on anything at first, I would just scroll down and get intimidated by looking at the thumbnails of well-endowed men having sex with big buxomed women who looked nothing like me. But eventually, I stumbled upon a "teen" site, and everything changed. A lot of the girls in the thumbnails looked like me. Pale skin, brown hair, slight frame. That made the sex feel less intimidating and more real. It gave me the courage to finally go all the way and finally click on one of the thumbnails that took me to a gallery. I clicked on the first photo and it blew up on my screen. I will never forget that image. A young, innocent-looking girl, not much older than me and more on the side of cute than hot, small breasts too, same as me. She was leaning over an older man, who must've been in his 40s by the looks of it, and her hand was wrapped around his huge, veiny member. The sight of that immediately fascinated me. I looked at my own hand and it looked just like hers. Was that what it would look like if I was grabbing Ryan's penis? Surely he couldn't be that big, although in my innocence I kinda hoped that it would because bigger had to be better, right?. Suffice it to say that adult Lily would eventually learn that’s not always the case; but that’s a story for another chapter.
I was mesmerized by those pictures of that young girl handling that huge, swollen organ, and oh was it making me so horny. I then noticed the handjob tag below the picture and decided to focus my research on that for the time being, since anything else was still too intimidating. I must've watched half a dozen short videos of young girls pleasuring older men with nothing but their hands, closely studying the way they jerked and caressed, using one hand sometimes, using both some other times. And I would touch myself, trying to make myself orgasm just as the man in the video exploded all over her. I even went as far as to practice with a cucumber, just so I could pretend it was the real thing as I did my best to imitate what I saw on screen. I know what you must be thinking, did I ever do anything else with that girthy vegetable? The truth, unexciting as it might be, is that I did try it and couldn’t go through with it. One particular day I got home feeling extra motivated after having watched Ryan during gym class, I put that cucumber against my entrance and felt the shivers running through my body as the tip made its way inside, but the second I felt the girth starting to stretch me I got scared and chickened out, choosing to finish myself with my finger instead.
As luck would have it, Ryan and I got paired up by the teacher again that same week for a special project. I was a straight As student and he was… well, more athletically inclined. I had told my mom about him and knew that if we went to my place she would likely embarrass me by asking all sorts of questions and putting me on the spot, so I suggested we do the project at his house instead.
Ryan's dad worked nights so by 6 PM he was gone. It was the first time I had gotten to talk to him outside of school and I was so nervous to be alone with him, but I was pleasantly surprised at how down to earth and nice he actually was. His dad was divorced and so was my mom so we had that in common, and now that he was away from all the popular kids at school he didn’t seem like a golden God, just a normal person that happened to look like a golden God. That's not to say I had stopped being in awe of him, if anything I was feeling even more attracted to him than ever before. He was still gorgeous and confident and charming as hell, but I was starting to fall in love with what I thought was the real Ryan, the one most people never got to see.
An hour passed, then another one, and we started getting more comfortable with each other as the night went on. At one point he had to excuse himself because it was time to put his little brothers to bed and I thought that was the sweetest thing ever. I just could not keep my eyes off of him, even to the detriment of our science project. And then the most amazing thing happened as I was leaning over the table to reach for a marker. I somehow felt his eyes on me and when I looked back I saw that he was checking out my butt. I had picked a pair of jeans that were especially form-fitting around my posterior, and checked myself in the mirror a thousand times before leaving home to make sure the white button-up shirt looked good with them.
 |
| My outfit for a science project. |
I had even snuck out a pair of my mother’s high heels, hiding them in my bag so she wouldn’t see them and putting them on right before I rang Ryan’s doorbell; all for a school project. My feet were already killing me but it had definitely worked, I could see it in his eyes.
 |
| Trying to look cool in my mom's shoes. |
I couldn't believe it. Me, the girl with the bushy eyebrows, getting Ryan Waller's undivided attention. I felt myself blushing and when he saw that I had caught him he just smiled in this incredibly charming way that would've disarmed me completely if not for the fact that I had already been under his spell for years.
"Sorry, I... couldn't help it," he said as I straightened up.
"No, it's fine, really, I'm... flattered," I replied, stumbling over my own words, feeling my face turning red, not knowing what to do with my hands and fearing my head was about to explode.
"It's just that..." He took a step towards me, "You look really hot tonight."
"I... I do?" I said, shaking.
"Yeah, I guess I never noticed before how pretty you are."
 |
| The girl Ryan never noticed before. |
By this point he was almost on top of me, my body pinned between his and the dinning table. I felt him lean on me and in an instant, his broad chest pressed against my small breasts as he kissed me very gently on the lips. I was shocked and only managed to blurt out an awkward "Thank you" before returning the kiss. He ran his hand through my hair and broke our kiss so he could look into my eyes. It wasn't just any look, it was a lover's look, although looking back on it now I realize it was more like he was sizing me up, making sure I was under his spell before going in for the kill. I totally was, of course, and he knew it, but at the time I thought that was true love burning in his eyes. "W--what?" I stuttered, trembling uncontrollably. He smiled, his emerald eyes piercing my soul. Slowly, he ran the tip of his fingers from my lips down my body. My neck, between my breasts, creating a trail down my abdomen until they reached right under my belly button. Low rise jeans were in fashion at the time and he caressed the exposed skin right above my pubis, tickling me a little before deftly undoing the button and slipping his hand under the waistband.
It seemed to be happening in slow motion, Ryan Waller’s hand in my pants, going down between my legs, where no one else but me had been before. He ventured further down, his fingertips brushing over my short trimmed pubes. I was so nervous, but my body was aching to be touched. He continued further down and when I felt the tip of his fingers brush my lips I gasped and my hips moved forward on their own, inviting him to continue. I remember holding on to the edge of the table, my knees shaking from pure excitement as his finger teased my pussy lips while he looked straight at me. "R--Ryan," I began to say. I don't know what was going to follow because right then his finger found my entrance and slipped inside of me. A rush of blood to the head froze me and I leaned my body back and pushed my hips further forward so he could really slide all the way into me. His free hand came up, unzipped me and hastily pulled my jeans down to my knees.
Before leaving home that day, as I was picking my outfit, it had taken me a long time to decide on what kind of underwear I’d be wearing. And I never actually believed he’d be in a position to see them, much less pull them off me, but I wanted to feel confident and sexy in everything I had on me, so I'd picked a pair of white lace bikini panties that I had bought without my mom knowing.
 |
| Appropriate panties for a science project. |
They were a lot more “adult” than the stuff I would normally wear, but I thought I looked really cute in them. But when it came to it, Ryan didn’t even seem to notice them, he just tugged them down with the same recklessness and then wrapped that same hand around my neck, pulling me in for another kiss.
I was terrified. Suddenly my little bush was in full view, right there in his family’s kitchen. I felt my whole face turning red, things were moving so fast I felt like I could do nothing but watch as that finger moved inside of me. Don’t get me wrong, I was scared of the moment, not him. Despite all the time I had spent dreaming about that moment, I was still not even close to being ready to go through with it. And yet, the way he was taking charge was making me feel not only aroused, but reassured somehow that this needed to happen. After all those times I had pleasured myself thinking of him, now Ryan Waller himself was the one doing it for me. As I folded in his hands, I told myself that it had to be fate and we were destined to be together. It was too perfect not to be true.
I was trying to keep up with his tongue thrashing around in my mouth when he pulled back to put two fingers inside of me. I had never felt anything like it, the closest I had gotten was that cucumber, and as I mentioned before, I had bailed on it at the last second. But I was under Ryan’s spell and his thick fingers were pushing all the way inside of me, making my knees buckle as I moaned his name lightly on his lips.
He must've liked that, because he went from slowly massaging me to pistoning his fingers in and out without any caution. I didn't know any better, I figured that was just how guys did it, so I bit my lip and took it, tilting my head back as he kissed up and down my neck, the initial pain being replaced by the electric build-up of pleasure I had grown accustomed to in my bathroom, but greatly intensified by Ryan's presence. I felt myself getting wetter, more than I thought was possible and, in complete disregard for his little brothers sleeping in the next room, I started moaning louder and louder. I threw caution to the wind as Ryan started pulling at the buttons on my shirt, telling myself it was okay because he was the love of my life, so I helped him open them before he pulled one of the cups on my girly white bra down and latched his mouth around my breast. That was the greatest thing that had ever happened to me and I held his head and pulled him closer, loving the way his tongue ran in circles over my aroused nipple as I continued to moan and push my hips against his wrist. I remember feeling the cold edge of the wooden table digging into my bare bottom and thinking how wrong it was to be there naked in his dining room, even as I begged him not to stop.
At that point he must've known he had me, because he pulled the other cup of my bra down before just ripping the whole thing off of me. I barely had time to gasp before he was on my other breast, squeezing and sucking, clamping his lips and pulling on my hardened nipple while he continued pumping his finger in and out - his fingers all the way in now, in and out, relentlessly.
"Yes, yes, yes!" I eventually started screaming, loud enough that, in retrospect, there was no way his siblings didn't hear me. I lost control of myself; I forgot everything my mother had taught about how a proper young lady should act and openly begged him to make me cum. Suddenly, I felt my pussy gripping his fingers tightly and it took every last bit of self control in me to keep myself from crying in ecstasy as a wave of pleasure washed over me. I felt Ryan holding me with one strong arm as his fingers continued to slip in and out of my quivering pussy, and myself gushing all over it while I hugged him tightly and moaned into his shoulder.
Now that I’m older I understand that was nothing but a young girl’s crush, but in that moment, as I held on to him and felt his fingers slowing down, I thought what I was experiencing was true love; and I wished we could stay like that forever. In all honesty and after all the things I’ve experienced since, there still are times I wish I could return to that blissful ignorance, when life was simpler and having a cute boy’s fingers inside of me was a life-altering moment.
And then, as soon as I started coming back to earth, a wave of shame came over me when I realized I had just come on his hand, in his dining room, with his two brothers sleeping in the next room. I didn't know what to say or how to act as I started to compose myself. I remember stuttering something after he removed his hand from between my legs and then an impish smile on his face as he looked at my wetness all over his fingers. I looked at his hand too and right below it, his fully erect penis, under his jeans. I really wanted to touch it, to feel it in my hand, but this was our first time hanging out and I had already crossed so many lines, I was terrified of what he would think of me if I did. I was trying to come up with something to say, anything to make the moment less awkward, and then I watched him slowly raise those wet fingers and bring them to my face, giving me enough time to see how they glistened from up close before he said to me, "Lick them."
"Wh--wh--what?" I stuttered like an idiot.
"Come on, give ‘em a lick," he replied.
My mind was racing. Was that something boys wanted to see? I had no idea, I wasn't sure if he was joking or messing with me, but then he pressed those fingers to my lips and I felt the warmness of my own sex and smelled my own arousal. I was so embarrassed, but seeing his delighted reaction after I stuck out my tongue and licked one of his fingers made me feel amazing, so sexy and grown up (or so I thought at the time). I became more daring and made a point of slowly dragging my tongue from his knuckle to the tip, holding back a giggle as I watched his face contort into an expression of pure, unbridled lust. It was so incredibly exciting to realize I could have that effect on someone, especially him. Ryan Waller, losing his cool because of me, completely captivated by me, hard as a damn rock for me. I felt like I was floating, and not just because I had just had the best orgasm of my life, but because it seemed like all my dreams and fantasies were finally coming true.
"You're so fucking hot," he said to me before he pushed those two fingers deep into my mouth. I was happy to let him do it, happy to close my lips around them and taste myself, happy to look him in the eye as he pushed them in and out of my mouth, the same way he’d done with my pussy, even if I didn't quite understand what he was preparing me for.
Finally, he pulled them out and kissed me again. I could feel his hard penis, still trapped in his shorts, poking my navel and his hand squeezing my butt cheek as he said to me, "Let's go to my room." I was about to say yes, and this story would've been completely different, if not for the fact that my mom decided to call me right at that moment. The phone ringing startled me and I jumped in his arms. I didn't answer, of course, I wasn't even close to being in the right mental state for that, but just seeing her name on the screen was enough to bring me back to my senses. What the hell was I doing? Letting some boy in my class who I hadn't even gone on a date with finger me? Even if he was my future husband and we were destined to be together, letting him take me to his room so soon did not fit with the romantic ideal I’ve built up in my head. I told myself that was not how my mother had raised me and, after gathering all of my courage, I politely declined. I told Ryan things were moving too fast for me and asked if he could take me home. It was very evident he was not thrilled but, to his credit, he was a perfect gentleman about it. He didn't get angry, he didn't pressure me, he just said, "Okay," and drove me home.
Except, that's not the whole story, dear reader. I was about to do something a little bit dumb and a little bit reckless that would end up shaping the rest of my high school experience as well as my interactions with men for years to come.
---
You see, the ride home was super awkward. As he was driving me home I had started to feel embarrassed that I had chickened out. Everyone at school knew that Ryan hung out with college girls on the regular. He was accustomed to being with women who were older, hotter and way more experienced and sophisticated than I could ever hope to be at that age. Girls that were cool and didn't have muppet eyebrows like me. Meanwhile, I was the dorky girl reading Harry Potter books during lunch who, for some reason I still couldn't figure out, had actually gotten the attention of the hottest, most popular guy in school; and I had rejected him! Me, the virgin who had been fantasizing about him for years, dreaming of the day he would finally say something to me across the hall, pleasuring myself almost daily while thinking about him… about my first time being with him... that same girl had panicked and asked him to take her home like a total loser when she could have had the thing she desired most.
Obviously I realize now just how immature those thoughts were, and let me be clear that all women (especially young teenage girls like I was) should always have the right to say No at any point, but back then I didn't know what I do now. 'He must think I'm an idiot' I kept thinking, 'He'll probably never want to talk to me again'. I started imagining what it would be like at school the next day, with him avoiding me or worse, telling the other kids that I was both a tease and a prude. By the time we parked outside my house, I was completely freaking out.
"We're here," he said with a very distant, almost emotionless tone. I turned to him and thanked him, but something took over me as I leaned in. All I knew was that if I said good night and got out of the car, I would regret it for the rest of my life, so instead of kissing him on the cheek I went for the lips. I put my hand on his thigh and realized he still had an erection right before he kissed me back. He was still into me, I still had an opportunity! That was all that I needed, I decided to go for it right then and there and my hand moved to his crotch. I held his penis in my hand and it was incredible. Even with his pants still in the way, all I could think of were the girls in those videos, and how my fantasies were finally coming true. I felt him getting harder as our tongues wrestled and I was ecstatic, it didn't even matter that we were parked right outside my house, that my mom or one of the neighbors could catch us if they looked our way, all that mattered was that he still liked me and that my silly white wedding dreams were still possible. So I kept going, pawing at his penis while he helped me unzip him. I took it out of his boxers and found that it wasn’t as big as some of the ones I had seen in those pornos, but it certainly wasn’t small, and more importantly, it looked so swollen and juicy, twitching in my palm as I wrapped my fingers around it. He forced his hand inside my blouse and a couple of the buttons popped off, but I didn’t care, too excited and frantic about the fact that I was touching his penis for the very first time. Oh his big, strong fingers clenching around my small breast had me moaning in his mouth right away and my little hand tightened its grip on his hard, warm cock. I gave it a little squeeze, and saw the clear droplet appearing at the slit, his precum plainly visible thanks to the bright street lights coming through the driver’s window. Fascinated by this, I leaned closer, getting a good look at the tip, and inhaling the scent of his manhood while his other hand slipped into the back of my pants to grab my butt. Still curious, I reached out with my index finger and tapped at the slit opening. Ryan hissed, reacting to that sudden pleasurable sensation, and as I lifted my finger, the fluid stretched up, clinging to my fingertip as well as his slit. I loved it so much, I wanted to play with it like that for a longer time, familiarize myself with every vein and bump, but then I remembered where we were.
I looked around us, the lights inside my house were off and the curtains were drawn, the street seemed completely empty... I was going for it. For all the shame and fear of getting caught, my pussy was still burning. The sensation of Ryan's fingers inside me had left me just wanting more and, as mortifying as it was to be doing that in front of my own house, with my mother just a few feet away, I was actually shocked at just how irresistible the impulse to keep going was. And so, with half his right hand in my butt crack and the other one pawing at my breasts, I began to stroke him, my face moving closer and closer to his crotch as if pushed by an invisible force. His cock was pointing straight out, pointing at my face, and I eventually got close enough to let it touch my cheek. "Umm," he moaned and I smiled to myself while I felt its warmth and hardness on my face, and the wet precum that stuck to my skin. I was like a little kitten rubbing myself on a foreign object when he pulled his hand out of my pants and put it on top of mine, aiming the tip of his penis at my mouth. I saw there was another drop of precum beginning to ooze its way out of the eye as he held his cock and I hesitated. I had only watched handjob videos up to that point, I had no idea what giving oral sex was supposed to be like.
"Come on, what are you waiting for?" he said to me. Not the most romantic of lines, I know, but in that moment it did have the desired effect on me. I was already there, kneeling on the seat with my butt in the air, holding his penis in my hand, risking getting caught... What was I waiting for?
I stopped waiting and finally opened my mouth and stuck out my tongue so I could lick the moisture off the tip. "Ohhhh yeah," he sighed, and the way he said it, so full of relief, made me open my mouth wider. I let him push it in. His cock was warm, thick, and almost pulsing. I didn't know what I was doing so I just licked around the underside as he began to slide it in and out ever so gently, carefully fucking my mouth with his cock, something I’d never even heard about before. I felt so dirty, but also a little relieved that he had taken the lead so I wouldn't embarrass myself by doing a poor job.
"Ohhh yeah, Lily, ooohhh shit, Lily," I heard him saying, and knowing that he was enjoying it and repeating my name like that turned me on so much that I almost didn't notice the car passing by until it was right next to us. It was probably going too fast to notice us, and there's no way they could've seen me while I was down there in his lap, but I still felt a rush of shame for doing something like that right on the street like some kind of hooker. 'Am I a skank? This isn't what proper young ladies do,' I kept telling myself as he continued using my mouth. But even as these thoughts crept into my mind, his cock between my lips just felt so right and helped to ease my doubts.
"Oh yeah, Lily, oh yeah, just like that."
Wanting to impress him, I copied a move from the handjob videos I had seen and cupped his testicles, gently squeezing them while the spit from my mouth covered them and my fingers. We spent I don’t know how long like that, Ryan moaning and thrusting into my mouth, and me doing my best to keep myself from falling while I let him use my mouth as he needed to, hoping he’d explode just like in the videos.
"Ohhhh, Lily, FUCK! I'm gonna cum, I'm gonna cum soon!" he told me just as another car went past us, and I started getting scared again that someone would see us; the thought of my mom finding out shaming me to no end. And yet as I felt him throb, I wanted him to finish, to help him feel as good as he had made me feel in his kitchen. But more than that, I wanted him to know that I wasn't just a tease, that I was just as cool as the other girls he usually hung around with.
"That's it, that's it. Ooohh, yeah, suck my cock, Lily, suck it!" he said, grabbing the back of my head and thrusting it down to his cock, ramming it deeper into my mouth. I felt a mix of shame and excitement at his words. I wasn't doing any actual sucking, he was pretty much doing all the work himself, but I still loved hearing him saying my name like that, the same way I had heard the men talk in those videos I had been secretly watching.
"Fuck, I'm gonna cum, fuck, fuck, FUCK!"
His thrusting became more urgent and his cock started hitting the back of my throat. I didn't enjoy that part of it to be perfectly honest, but I knew that soon he was going to finish so I hung in there, trying my best not to ruin the experience for him. ‘Ryan Waller is going to cum in my mouth! Ryan Waller is going to cum in my mouth!’ I kept telling myself, as if I had just won some strange lottery, and even though I had no idea what that would feel like, I still wanted it so bad.
It didn’t take long for my wish to come true, but right before he came, Ryan made the strangest sound. It was this raspy, drawn out groan, like something invisible had just wounded him. I’ve been with many men since and I feel like I’ve seen and heard it all at this point, but that was my first time seeing and hearing a man achieving climax in real life, and it freaked me out so much that I started to fear that somehow I had done something wrong.
When I think about it now it’s so funny to me just how terrified I was of doing “a bad job”, as if pleasuring a man wasn’t the easiest thing in the world. But of course I didn’t know that then, and when he all of a sudden tensed up and I felt the first blast of semen hit the back of my throat, I audibly gasped and instinctively recoiled. None of the clips I had been watching in secret had prepared me for how powerful his ejaculation was, and just as it slipped out of my mouth, Ryan held me there and the next spurt hit the top of my forehead. It was a shocking sensation and it was happening so fast, but somehow I realized that getting cum on my hair would not be a good thing once I had to face my mom, so I tilted my head so that the head of his cock was pressed against my cheek to keep it in check somehow. I remember feeling the force of it pumping under my thumb, shooting sperm all over the side of my face and Ryan sighing loudly as he neared the end. He pulled his cock from my grasp and jerked it himself as I watched the last white drops splashing onto my forehead, my eyebrow, my lips.
When he was done, I had cum running down the entire left side of my face. I could feel some of it stuck to my lashes, and a thick wad dangling from my chin as I started looking around for something to wipe it down with.
"Fuck, that was good," He said to me as he pulled up his jeans and looked at my cum-covered face. "Yeah? You... liked it?" was all I managed to reply before I found a single tissue in the glove box to try and clean myself with. "Yeah, you were great. I mean we didn't finish the assignment but I'm sure you’ll take care of that, right? I mean you're so smart, I’d really just be a hindrance anyway."
Before I could figure out what to say, he leaned in and opened the car door for me. "It’s really late, I should, uh... get back to my little brothers." I didn't know what else to do but to obediently step out of the car.
And then just like that he was gone. I didn’t even get a chance to say good night. I just stood there on the sidewalk, frozen, holding my ripped shirt closed with the smell of his semen all around me, my lips and cheek still wet with his cum, trying to convince myself that I had not imagined what had just happened.I had no idea if my mom was still up so I knew I had to be cautious before I went inside. My hands were shaking as I checked if there was still any evidence on me. My face felt sticky but mostly dry. I ran my fingers through my hair and did my best to get the cum out and cover the wet patch with dry hair. Then I took a deep breath and I opened the front door. I had almost made it to my room when mom caught up to me.
"Oh honey, your makeup is all runny! Have you been crying? Is everything okay?"
"Uh, yeah, I just-- I was watching a really sad movie."
"Movie? But I thought you were gonna work on a school project?"
"Yeah, yeah, we, uh, finished early."
I closed my bedroom door behind me and let out the biggest sigh of my life. I was still so full of adrenaline that instead of going to bed I spent the next few hours reliving everything. After all those months rehearsing by myself in the bathroom, I had gotten my first real sexual experience with a boy. And not just any boy, Ryan Waller, the boy I had had a crush on for so long, he had been in my mouth, he had made me cum with his fingers, and he had cum between my lips, his taste still fresh on my tongue. Even though the night had ended on a weird note, I still felt like the luckiest girl in the world. I felt such power at having made him cum that I couldn’t keep myself from running my hands over my face, trying to re-experience the feel of his seed all over my face, remembering the smell and the taste and the texture for God knows how long, until I realized I still had to finish the damn science project.
I told myself that having to stay up late doing homework was a small price to pay for what had just happened between Ryan and me and right away I started dreaming about what the next day at school would be like. There was a connection between us, I was so sure. He’d didn’t just tell me I was pretty, he'd said I was “fucking hot”. No one had ever said that to me. Surely after that-- and everything else that had happened in his car-- he would have to ask me to be his girlfriend. I was beaming. Me, the dorky girl with the bushy eyebrows, I was about to be Ryan Waller's girlfriend.
I was freaking out, even after I’d finished the assignment I still couldn't sleep. I laid in bed, touching myself to the fresh memories of Ryan’s cock in my mouth, and I knew that my high school life was about to change forever. But I never would have guessed exactly how.
---
I can’t help but laugh and cringe at myself when I think about it now. I was so innocent and clueless that it never crossed my mind that what had happened could be anything but the beginning of a beautiful, movie-like romance, when in reality I’d just had my first experience with casual sex. The first of many, as you will discover in later chapters of this book. But let me make it clear for all my young readers out there, casual sex can be incredibly fun and satisfying when it’s between two consenting adults that understand it’s all about pleasure and living in the moment. When you’re young and you don’t really know what you’re doing, I believe it’s best to make sure you’re doing it with someone who you know you can trust, someone who’s proven to be worthy of that trust and not just the popular guy at school.
And that’s a lesson I learned with Ryan every step along the way.
END OF PART 1.
Comments
Post a Comment