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Hey all. This is a really long one, but I just couldn’t leave any of this out. This was one of the best thing I’ve ever experienced in my entire life, not just my sex life. I still can’t believe it happened. I have three parts that Ill release right away if anyone asks. I hope yall still read this despite the length, because the background is really crucial and the sex was so amazing I couldnt leave one thing out. This all happend a two weekends ago. We all have that one high school crush that defines and molds our fantasies as a teenager. Sure, we go through phases and different crushes throughout those awkward, tongue-tied years. But I think most of us have that one girl or guy who was just out of our league, or that dated a best friend, or that just never seemed attainable. You find yourself wanting what you can’t have, and some of us obsess and fantasize about that person for far too long. For me, this was especially true. For me, that crush was Katie. We went to a small private high school together, but she never really fit in. Nearly every girl at my little Catholic school was a rich, white, Republican goody-goody two shoes from the suburbs of Kansas City. You know the type. All destined for an expensive education and sorority life at some big state university. Katie didn’t fit that mold, and she was a bit of an outcast for it. She definitely had the hipster vibe going on before "hipster" was the annoying and overused term it is today. She went and got a really short pixie haircut when she was a junior and was accused of being a lesbian by some of the other girls. She was an avowed atheist, which sat very poorly with the whole community. She was fascinated with the Riot Grrl movement, loved punk rock, adored psychedelic music, and would debate you in politics any day of the week. Politically she was pretty liberal and that again pissed off every girl she came into contact with. However, the I believe the real reason she wasn’t liked from the get go by most of the other girls was that she was gorgeous and different at the same time. She came in her sophomore year, one of only two new students. And she knew she owned at least half of the school on her first day: the boys. She had every guy she came into contact with under her spell. Katie even hooked up with our school’s football captain superstar, the classic high-school center of attention, just because she could. His ex-girlfriends and future girlfriends hated her beyond belief. She could also be a bitch. Not so much an evil-behind-your-back-bitch, but more of a fuck-you-dont-mess-with-me-bitch. But let me just try to describe her physically in a way that does some justice. Her perfect pale skin would make any other teenage girl curse God’s name. We usually associate glowing skin with someone who has a tan. But hers was somehow glowing and also nearly translucent, and I even remember her ripping on a girl for her fake tan. Loved it. Her glances flashed the brightest and biggest green eyes you have ever seen, and they were sparked by an attractive intelligence and fire you couldn’t ignore. You’d drown in them. Her frame was the definition of petite and she had a cute little butt on her that hypnotized you when she walked around in her schoolgirl skirt. We’d have mass on Thursdays, and the stockings would drive me out of my mind. She had tiny but elegant little arms and legs that made her look completely powerless, despite her rebel girl demeanor. A beautiful pair of pouty lips greeted you with every smile and made your heart melt. She had a small, round face with an elegant little jawline that rested on an even more elegant little neck. Sandy blonde hair overflowed in waves down her back and chest and was usually a little messy, but was just perfect no matter how she wore it, and the little pixie hair cut she eventually sported separated her from the mundaneness of every other girl I knew at my school. Despite all of these cute and sexy little traits, despite the rebel girl demeanor that separated her from the rest of the girls, there was really only one reason she made every teenage boy within twenty yards short of breath. She had a pair of tits that were just absurd. On her tiny frame, they looked like a pair from some sort of sexy anime film. You know those female cartoon images that people say destroy the self-confidence of little girls everywhere because those proportions are literally impossible? She was a real life version of that. Her boobs were just obnoxiously disproportionate to the rest of her body in the absolute best way possible. I am not kidding you, her boobs would qualify as triple DDDs on a girl six inches taller and fifty pounds heavier than her. You’d have to say they were fake, if she wasn’t sixteen years old at the time. School uniforms sported blouses that were intentionally baggy and buttoned all the way up. Even girls with a nice pair of C cups couldn’t give us boys a hint of what was underneath even if they tried. Katie was the exception. Not even a blouse designed for modesty by a Catholic school could contain her rack. Occasionally, we’d have days where uniforms didn’t apply. Retreats, field trips, etc. It was on these days she would bust out a little white or yellow tank top, kept on her body by two tiny spaghetti straps, her cleavage looking like it was about to explode from her bra. Even she wore a blouse that wasn’t low cut, it didn’t matter. Her tits would push up and out towards you because they had nowhere else to go. In summary, Katie was the purest definition of busty petite. Now, I’m sounding pretty voyeuristic at this point. But we were actually friends and spent a lot of time together, so these details were engraved in me. We were friends through our love of music and went to see a few concerts together. I wasn’t the best at talking with girls but certainly not the worst. Of course, when we’d hang out, I’d fantasize about her constantly and the thoughts just built up after years and years. We eventually went out on one "date", and I tried to make a move and it ended awkwardly. I never tried again until I was 22. Fast-forward four years. I’ve graduated, and we’re both 22 years old. I’ve changed a lot. I am more confident. I lift weights. I have a good job. She’s changed too. And when I say changed, I mean she’s only gotten more gorgeous. She’s older now, more elegant, knows who she is, and her hair is long and wavy again. But one thing hasn’t changed. Shes still the poster child for impossible proportions. 5’2, tiny as can be, with a rack that is no doubt is responsible for at least a few fender benders. Now, we’ve kept in touch but not frequently. I haven’t checked her out actively on Facebook in probably two years though. A few months after graduation, I see on her Facebook, message her, and find that she got a job in St. Louis just like me. Cool. I get a little twinge of my teenage angst after our conversation, remembering my three year long crush on her in high school. I look through some of her pictures, not sure how I’ll feel. And of course, inevitably, all of those horny teenage memories hit me like a truck when I find her in string bikini from a spring break album. Fuck, I’d forgotten what a heartbreaker she is. That string bikini is taking a lot of abuse and looks like it’s going to pop off any second. She sticks out like a sore thumb. Surrounded by all her friends with fresh spray tans and bodies that dont even compare, Katie is a white, transparent ghost in the blazing sun. A sexy fucking ghost. That night, brushing my teeth, I recalled my one attempt almost six years ago that ended so damn awkwardly. Then, looking at myself in the mirror, it hits me. I’m not the same person anymore. I could make this happen. I’m 22. I’m not 16. I have a job. I am good looking. We haven’t really hung out in years. I could try this one more time with a clean slate. Over the next week, the idea possesses me. I’ll admit, after a little self-reflection, I started feeling a little pathetic. I am a completely different person now. I shouldn’t be reverting back to my high-school days of obsessing over this one little crush. But why not try? I’ll regret it if I don’t. I text her and tell her we should catch up sometime. She agrees and now I’m getting pretty excited. We meet for coffee two days later, chat, and I’m trying my best to keep it cool, which seems to be working. More than anything, I’m glad she seems to recognize I look a lot different from the last time we saw each other three or so years ago. I’m getting glances I would never have received back in high school, but the overall feel of the conversation is still very platonic. Weeks go by, and we’re texting regularly and go out to see a movie once. The flirting hasn’t died down, but I’m starting to worry. It always seems so hit and miss. I’m losing hope. I just make something happen. Make a move. Anything. Luckily, I never had to. I text her later that day. Me: "Hey Katie. What’s up?" Katie: "Not much. I’m really bored at home. You?" Me: "Same. Let me entertain you." Katie: "Haha. How?" Me: "Fuck, marry, kill. Hitler, Dick Cheney, Hannibal Lector." [We both have a weird, fucked up sense of humor] Katie: "Fuck Cheney, marry Lector, kill Hitler." Me: "Good picks lol." Katie: "Your turn. Fuck, marry, kill. Jennifer Lawrence, Queen Elizabeth, and me." My heart stops. I’m staring at my phone. Why would she put herself in the mix? To be funny? To get me to admit what she’s known for years? That I want to fuck her brains out? Or am I reading way too much into it? With any other girl, I would respond immediately and assume shes hinting at sex with me. But this is Katie. All those years of fantasizing and those sparse moments of embarrassing rejection have me running in circles. Fuck it. Me: "I’d marry Jennifer Lawrence, kill queen Elizabeth, and fuck you. But if the sex blew my mind, I’d kill Lawrence and marry you instead." An agonizing six minutes passes before I get a response. Katie: "Good answer haha. What could I do to blow your mind? What are you into?" I can’t believe this conversation is taking place. She’s asking what I like in bed. I decide to go all out and be honest and graphic to get her imagine going. But first I’ll make her admit she’s interested. Me: "Oh shit haha. I’m into some pretty kinky stuff. I’m sure you don’t want to hear about all of that :P" Katie: "Tell me! Maybe our preferences will match up haha. I don’t get embarrassed about that stuff." Me: "Okay. Fine. I’m not usually into the vanilla, lovey dovey sort of sex. I always love to talk dirty, spank, pull hair, choke, bite, all that sort of stuff. I love to be in control, dominate, pin a girl down and make her beg. I love giving orders and just taking control." Katie: "Uhhhh yeah it sounds like you’re a little more kinky than me but I’ve never had many guys who were into that anyway lol. Definitely don’t mind a guy who takes control." Me: "Haha fair enough. So what are you into that most guys would be surprised about?" Katie: "Well. I was deathly afraid of getting pregnant in high school so my first boyfriend and I only did anal haha. Doing that so much I got used to it and then started loving it so yeah guys are always surprised by that lol" This conversation had already given me a slight boner. That message quite literally took me from half-mast to one of the most furious erections in my life in maybe twenty seconds. After that, things just snowballed and we were talking about all of our fantasies, best ex-partners, favorite little tricks in the bedroom. Talk of toys, sexual communication, our Kinsey scale rating, whatever we felt like. I finally told her that this conversation was making me pretty horny and that I may need to take a break to relieve some steam. Then she dropped another bomb on me. Katie: "What? Can’t do two things at once. I’m working getting off right now :P" My heart drops out of my chest. Without hesitation, without thinking, I take a SnapChat and send it to her that says: "Prove it." I didn’t even care if the face of curiosity I was making looked sexy in the picture or not. I was dying here. Not a minute later, I get a SnapChat back of her soaked fingers covering her bare pussy from her perspective lying down, her pale skin glowing and her tiny little hips making the perfect hourglass shape. And just like that it’s gone. Curse her. Three-second window. The whole interaction was over about ten minutes later when she said her friends were coming over to go out. I told her that this wasn’t over, and she agreed. Now, I obviously felt pretty confident going forward. In fact, I texted her the next day saying I wanted her at my place alone that night. She said she couldn’t, but that she’d be over tomorrow night at 7:00. I had never prepared for a "date" so thoroughly before in my life. My studio apartment was spotless. My vinyl collection reorganized and my gramophone turned on and ready for a little music. I bought lube, and lots of it. Condoms, and some new rope if she was feeling something kinkier. I bought a new sex toy, one of those rabbits that stimulates the clit while the ridged dildo spins and vibrates at the same time. She had mentioned wanting to try one in one of our talks, and I read the fucking manual and everything. I go to the gym for a light workout a few hours before, get a fresh haircut, by the most expensive razors at Wal-Mart I can find, shaved, brushed my teeth three times, used this new expensive mouth wash, the list went on and on. Everything had to be perfect. And at the end of that day, when the clock hit about 6:30, I was feeling sort of ridiculous. Would she notice how God damn hard I was trying? What if she shows up in sweatpants and a fucking tank-top and I’m sitting hear in my brand new button up and jeans? Doorbell rings, and my fears melt away as she takes off her winter coat. She was clearly thinking about me all day too. She’s wearing a soft gray sundress with a neckline of medium depth that would look fairly modest on any other girl, if her giant chest wasn’t trying to escape from the top where the fabric cuts off. Eye shadow and a healthy dose of makeup highlight her huge green eyes, and her long, sandy blonde hair comes down perfectly straight behind her back and over her chest. It’s at that moment that I realize I have nothing for us to do. No excuse for my intentions. I tell her to make herself comfortable and she has a seat on the couch. We chit-chat, she says she loves my place, I say thank you. I ask her if she wants some wine. She smiles and says no, that’s okay. Do you want to watch a movie? No, not really she says sort of sheepishly. My heart is now pounding as I stand in the kitchen and she sits on the couch observing my apartment. Now I’m nervous. Now I’m unsure. Now I’m transformed back into the awkward, scared, sixteen year old self as the woman I’ve been fantasizing about for years, who I’ve been sexting for weeks, sits ten feet away from me in my empty apartment. Silence. One second, two seconds, three seconds. I realize in that moment, four seconds after that awkward silence, I’m an idiot. I scream at every negative, self-doubting thought in my mind to get the fuck out. You’re banished. Now. I walk over to the couch, she looks up at me with that heartbreaker smile, and I lean over and kiss her. She kisses me back, and all the voices in my head just fade away. I’m content. I could only get this far and I’d be content because I had wanted to do kiss this girl since I was sixteen. Her warm lips are wrapped around mine and her breath speeds up ever so slightly. She sticks a tongue in my mouth and I’m a little shocked at first. I’ve never had a girl decide on French kissing ten seconds into making out. But it’s not a lusty, dive into your throat French kissing. She’s lightly whipping the tip of her tongue on mine, softly licking the inside of my lips. In all honesty, it was sort of funny to me. There’s no other way to describe it: she was a weird kisser. Not that I was complaining. I mirrored her motions. After a minute of standing over her and kissing her, I pushed her on her back and came over her, continuing our make out session. After a few more minutes I ran my hands over her arms and legs and neck ever so slightly, and the kissing got a little more intense. I kissed her elegant little neck as lightly as I could for a minute, then started licking, nibbling, and softly biting it. She was really silent, and I get off to the noises a girl makes during sex, so I was waiting for anything, a sign I was doing the right thing. Finally, as I lightly sucked on the area right below her earlobe, she gave out the most adorable, but barely audible, moan of pleasure. That little noise sent me into an entirely new frame of mind, my aggressive and dominant side really waking up for the first time. Now, I had been so focused on my job of warming her up that I had gotten lost in my own little world. When I finally pulled back up for air, away from her neck and mouth, another wave of realization washed over me. This was Katie. She looked up at me with those big green eyes I had gotten lost in hundreds of times before, her enormous tits now heaving from my attention, and I was just blown away this was happening. In that moment, I decided I was going to give this 110%. She was going to get fucked like she had never been fucked before. I scooped her up in my arms and sat her up on the couch, going in for another kiss. More aggressive, more urgent, sticking my tongue into her mouth and letting it swirl with hers. After a moment of this, I grabbed her under her arms and stood her up abruptly. In that moment remembered one of our texting sessions. She said she loved being watched. An idea came to me. "Katie," I said. "Yeah," she replied in a raspy whisper. "Take three steps back." "W-what?" she asked, confused. "Take three steps away from me. Now." I was using a voice that I just can’t replicate in everyday life. A voice totally possessed by lust and desire, one that I only really have control over in these moments. Sort of confused but obviously excited to be ordered around a bit, she did as I said. I took a seat on couch, leaving her standing in the middle of the room alone. "Take off that dress," I commanded. "Slowly." I don’t know what exactly possessed me to get her naked like this. I usually love stripping a girl down myself. But I think it had something to do with the build up that spanned over years of maddening curiosity. How many times had I pictured her naked? I didn’t want to just pull her dress off over her shoulders like Id do any other girl.. I wanted to drink her in, on my own time, just watching. As soon as I said the words, her face lit up. She obviously seemed to like this idea. Gripping the fabric at her thighs, she slowly peeled it off in one long motion. It wasnt necessarily sultry, like a strip tease. It was just a long, slow reveal. First thing I get to adore are those slender little legs. Then a lacy black thong encircling her small but shapely hips, a pierced bellybutton and a toned stomach, just on the brink of lady abs. And then of course she struggled to peel the rest of it past her tits. After a few seconds fighting her absurd breasts, the sundress literally pops under the strain and frees her breasts entirely. They were held up by a matching black lace bra that quite literally couldnt handle her breasts… about a quarter inch of her areolas protruded from the tops of the cups. I guess they dont make bras for a diaphragm to boob ratio like hers. As soon as she had the dress over her heard, she even tried to pull the front of her bra up a bit to fix it, but I could still make out the outlines of her nipples areolas peaking over the tops of the black lace. She immediately reached around to remove it entirely, but I stopped her right away. I was going to make this last as long as I could. "No," I said. "Not yet." I was just doing whatever I wanted now, doing things my way. I couldnt help it. I was possessed. The nerves had been replaced by animalistic desire. Desire that had been the net result of hundreds of hours of sneaking glances down tank tops. Of surfing Facebook for slutty Halloween pictures. Of hiding erections after every hug. Or failing to hide erections during a hug. Desire that had sent me into a masturbating frenzy hours after wed go swimming together. Desire that had built up and reached its climax when she sheepishly rejected my first attempt to kiss her. Confused but still allowing me to take the lead, she dropped her arms to her sides. I took my foot and pushed my wooden coffee table across the hardwood floor right next to her. "Come here," I motioned to the spot directly in front of me where the coffee table had been. She obeyed, standing over me, looking down, stripped right down to her panties and bra. I drank the site of her in and I could tell my expression alone was turning her on. I was giving her orders, but she knew who had the real power. "Turn around," I said. She obliged. Her tight little ass was now three feet from my face, and I resisted the urge to bury myself in it. The back of her thong was thinner than a shoelace. A thought that crossed my mind: she probably had the most under appreciated ass on the planet with those tits taking up all the attention. I’d have to change that tonight. I handed her a pillow. "Bend over on that coffee table. On your elbows. Use this. [Handing her the pillow.] Mmmm good, Katie. Now peel those panties off slowly." To my immense satisfaction, this exhibition without physical contact was clearly driving her wild. My commands alone were shortening her breath. She got on her knees, rested her chest on the pillow and reached around with both hands to slide off her panties. Now fully engaged in this game, she really took her time. Maybe an inch came down every five seconds, but it felt like a thousand. I, a man who had never rimmed a woman before in my life, knew instantly that that was about to change tonight. Her tight little asshole was so clean and cute and it just begged to be played with. When she finally got to her pussy, the lace took with it a sticky little streak of cum and she was already soaked. She must have given this night some thought, because I know the different between a shave and a full on bikini wax. She looked so smooth and soft. Her pussy itself was tiny, but she had long, pink labia that dripped with her juices. I was going to take my time with this game of striptease. "Katie, spread your pussy for me," I said in my now raspy, strained voice. My dick was starting to hurt under the strain of my jeans. "With both hands. That’s it. God, you’re already soaked. Katie, wider. Spread your lips as wide as you can. Mhmmm. Like that." Then the first words came out of her mouth since I had kissed her. With her pussy gaping open and with full knowledge that I was drinking in the site of her little hole, she said: "Mmmm. Fuck." That was it. No real dirty talk, just a moan and a whimpered "fuck". I leaned over and, without warning, literally as lightly as I could, pressed my warm tongue to her perineum. It didn’t seem right to lick her pussy yet. I would make this evening last forever if I could. She shuddered with surprise, as I slowly and gently ran my tongue up and down the length of her perineum. I then took one of her soaked outer lips in between my lips and sucked gently for a few seconds before letting go. She squirmed with pleasure, pushing her ass as high she could and arching her back so much it looked like it should hurt, hoping I’d go in for some more. But of course I didn’t. "Katie, stand up. I’m not done watching you strip." crushingonthroways [3 comments]