It Happened One Night [m/f] | 2016

Hello fellow readers! I'm a long time reader and I figured I would start sharing some of my more intimate life experiences with you all since you've shared so many with me. Little background on me, I am a mid-20's male who, only until recent years, kept to himself with regards to women or casual sex encounters. I consider myself husky and hobo-esque with my beard and longer than normal hair, but I tend to not have any trouble attracting women (and apparently some guys too) regardless of my looks.

Bit of backstory on this event. I was around 19 and a Freshman in college when this story occurs. The start of the semester was a whirlwind of new experiences for me as I suddenly found myself hanging out with newer crowds of people rather than just the same sort of clique from High School. The best part was that a good number of incoming Freshman happened to be from my same high school class of graduating seniors, so the new experiences were balanced out with close to everyone knowing everyone else. Some might say that this would be a drawback as some old high school drama might follow us into college, but on the whole, everyone seemed adamant to start fresh with one another and leave high school as high school.

To my benefit, this "fresh start" mentality enabled me to open up to the women of my graduating class like I had never dreamed of. I found myself sharing notes and gossip with 3 of the hottest girls from our class and it always made me laugh when I thought back on how mortified I would have been in high school if I ever tried anything like this. Unfortunately, most of the girls on campus were either already dating or were in the middle of hooking up with another guy and I was petrified of being labeled as a homewrecker in my Freshman year. So I kept it tame with them and became friends with a plethora of people.

There was one girl I spoke with a lot that struck me in a totally different way compared to the other girls on the campus. We'll call her Mary. Mary was a freshman who came to the college from a district that was far north of my old one. She was always a little timid in crowds, but when she was around her friends she was all bright smiles and mousy laughs. To paint the picture for you guys, she was around 5'2" with a very skinny body, think ballerina except a little more pudge (the cute kind). She had dark brown hair that surrounded her head in a little bob cut, milky white skin, and big watery hazel eyes hidden behind a pair of large rim glasses. Because it was the beginning of the Fall semester, she usually wore large sweaters and jackets with skinny jeans and converse. She wore only enough make-up to cover up the few freckles she had but otherwise that was her. To me, she was the cutest girl I'd ever seen. We met in the Film and Production History course we had together. She ended up arriving to the class late and stole the empty seat next to mine then broke the ice by asking me for some paper and a pen after she realized she'd forgot her bags. We occasionally whispered to each other throughout the class and learned that we had almost the exact same time-schedule, but with different classes, for the semester. Naturally, we managed to hang out quite a bit thanks to that stroke of coincidence.

Through our talks in and out of class, I learned that her father was a regular set/costume designer for Cirque Du Soleil and she was in school to try and earn a degree so that she could work professionally with her father and his friends. I thought it was strange that she was taking a Film class of all things, but she ended up explaining that she took it because she loved older films and loved studying the history behind modern day cinema. This piqued my interest in her because I was taking the class for the same reasons. We became close friends over the course of the semester and often invited one another to parties and concerts that we each heard about. I never really considered sex as an option between the two of us since she was almost always studying or working when she was in class or at the rare party. I also never got the "Hey, I'm attracted to you." vibe from her so I never really brought it up.

However, toward the end of the semester our Instructor assigned the class a fairly hefty workload that involved watching a few modern films of our choice and writing reports on them. Luckily it was a group assignment and the two of us decided to jump on it together. We decided to meet at my house the following weekend to burn through the films and get everything done in under a night. As you can imagine I spent a good while making my house presentable and visitor friendly because it almost never is (roommates....). Speaking of, they happened to be out of town in Vegas for the weekend which was perfect because at the time I imagined she'd be a little nervous being around 3 other dudes she didn't know.

She arrived at my place at around 7 wearing pretty much her normal attire with the one oddity being a knee high skirt and some stockings. I didn't say anything, but I can imagine her chuckle when I opened the door was because she noticed me staring just a smidge too long. I ended up grabbing the both of us some hot tea and we instantly set right to watching "The King's Speech." Nothing really noteworthy happened during that viewing, she seemed to be pretty engrossed in the film, especially the bits involving Helena Bonham Carter, which I thought was pretty cute. I had already seen the movie so I zoned out on the bits that dragged a bit, and I started to notice that the room was oddly quiet, despite the movie that was on. So quiet that I could hear her softly breathing across the couch. For some unknown reason I found myself slipping in and out of the film and her breathing which sounded like it was becoming louder, but I knew she hadn't changed anything at all. When the movie was done we sat around my coffee table and typed up our first comparison paper in very little time. Again, through the clicking of the keys I noticed her soft breaths and I frequently caught myself zoning out into my screen just listening. She seemed a bit confused when I wound up finishing my paper 20 minutes after she did. She asked if I was ok since she noticed me zoning out during the movie. I told her I was fine and that I'd get us some more tea. She narrowed her eyes at me in a confused "alright..." kind of way. I walked into the kitchen poured us some more teas and worked to calm myself down while I did so. As I said before, Mary had never been anything more than the cute girl from my film class, but now that she was here my mind had started spinning out of control with possible scenarios that involved her and I in some fairly explicit situations. This all started from me listening to her breathing and quietly imagining what her chest looks like when it rises and falls with her breathes...come to think of it I'd never seen her without a jacket on so I had no idea how large or small her chest was....

"Scott?"

I jumped way higher than I should have when I heard her voice and panicked when I spilt the tea kettle on the floor. She busted up laughing her mousy laugh as I, wide-eyed and red faced, slowly realized what happened. I had been leaning against the front of my oven for the last 5 minutes calming myself while she sat alone in the room wondering why I was taking so long to pour two drinks. I laughed nervously and grabbed a towel to start wiping up the floor. Mary, now leaning against the back of my bar stool to stay on her feet after laughing for so long, asked if I was honestly ok. I lied and told her that I was fine and that I just need a little fresh air. I knew she didn't buy that for a second because she snickered and told me to hurry up and "calm" down. Then she spun around and slowly sauntered away making obvious air quotes as she left the kitchen.

The way she said "calm" stuck with me. To me it sounded pretty sexy. Coupled with the fact that she chose to sway her hips very obviously as she walked left me feeling a little cold and turned on. I walked back into the living room and she had parked herself on the edge of the couch where I sat before. She looked up from her laptop and snickered again as I walked in. I rolled my eyes, sighed loudly, and grabbed the next movie. True Grit.

This was a movie I was excited about as Mary was the one who brought it and I'd never seen it. She chuckled when she saw my eyes light up as I looked at the front of the case. I popped in the disc, grabbed the last of our hot tea from the kitchen and returned to the room where I found her now sitting in the middle of the couch with her bare feet on the armrest. This annoyed me a little but now I saw an opportunity to do something a little risky and provocative to get back at her for the kitchen incident. I walked up to where she was sitting, set the teas on the table, snatched her laptop from her lap (with a satisfying "Hey!" to follow), picked her legs up off the armrest, sat myself down and replaced her legs where they were before. As I handed her the laptop again I noticed her eyes were wide in surprise, but she didn't move to change her position or tell me off. Instead she slammed her heels against my thigh, called me a dunce, and fixed up the pillows behind her so she was comfortable. It was around the time that she finally wiggled back into a sitting position and hid her face behind the laptop screen that I had realized exactly what I had done and exactly what kind of position I was in....because the remote was still on the coffee table out of arms reach.

I leaned forward to grab it but she smacked her legs into my stomach. I rolled my eyes and continued to lean forward to grab the remote. Suddenly she moved one of her feet back into my groin and loudly told me "If you keep fidgeting I'll slam your junk!" I laughed and made one last lunge to the remote (and my tea) and finally swiped it up. Like an ass, I tauntingly waved the remote if front of her monitor and got another kick in the thigh for it. We started up the movie but I realized that her foot was still parked against my groin and I could slightly feel her heel against my junk. I nervously glanced in her direction, but her face was now hidden behind the monitor. So I gulped down some tea and sat through about thirty minutes of the film with her one leg parked over mine and her other parked between mine.

Thankfully the fan from from her computer was now blocking out her breathing, but one stimulant was replaced by another as I noticed she adjusted her seat quite a few times during the movie. Everytime she moved she would press her foot more and more against me and at times it got uncomfortable, but I didn't say a word because FUCK was it hot. So much so that I noticed my cock was slowly begin to harden under the pressure. I kept my eyes focused on the movie and nothing else, but I couldn't help but notice her head turn in my direction everytime my cock pulsed against her. She knew, I knew, the only people who didn't know were Jeff Bridges and Matt Damon. I stretched my hands up and let out a yawn in an effort to play it off, but that only inspired her to rub her foot against my cock. I instantly tensed up and grabbed her knee, which, and I swear upon everything in this world, made her gasp a little. I could feel my zipper digging more and more into my ever-growing bulge and so I tipped her monitor screen down and told her I was going to go and change. She smiled and lifted her legs off of mine.

I quickly walked into my room, tore my pants and boxers off and yanked on a pair of pajama bottoms. I then wondered why I bothered taking off my boxers but I heard Mary loudly call for me to come back as I was missing an important part (Matt Damon got shot). I walked back into the room and found Mary sitting with her feet still parked on the armrest, the only difference this time was her computer had been shut and laid on the coffee table. I caught her eyeballing my choice of pants and grinning, but she quickly waved me over to sit in the couch with her again. I walked up to the couch and expected her to lift her legs, but she sat there smiling up at me with those big hazel eyes of hers. I groaned as obnoxiously as I could, grabbed her legs and yanked them up so I could sit down. Then, almost as if to show off, she wrapped her hands around her knees and the end of her skirt and pressed her legs against her body as they stuck straight up to the ceiling. I must've looked like an idiot when she did this because I sat there for for felt like forever just looking at her as she displayed this stupendous amount of flexibility to me.

"That's amazing" was all the wide-eyed 19 year old me could stammer out as I slowly sat down next to her. She laughed a bit, thanked me for the compliment and laid her legs down on top of mine. This time when she laid her legs down, her bum was now wedged up against my right thigh and her feet dangled over the edge of the armrest. She organized the pillows so that she could comfortably lay back and we stayed like this for the rest of the movie. While in this position, I could feel her wiggle her bum against my thigh and at the height of it all I could swear I felt the heat coming off her. As the film ended we both stretched a little and she got up and asked where my AC was controlled from. Being a college student, I couldn't afford an AC in my home so I broke the news to her. She just shrugged and lifted her sweater up over her head. Holy FUCK was she hot under that. She was so skinny underneath that huge sweater, it was like I was looking at a whole new person. Her tits weren't large at all, but I couldn't give two shits about the size of her chest at this point because I was more focused on the newfound curviness of her hips. Her skirt was hiding the rest of her and I was LOATHE of that thing, but I'm pretty sure she knew exactly what she was doing because she threw her jacket on the couch and proceeded to sway that magnificent hips toward my kitchen for some water. If I wasn't turned on before I certainly was now. I had to play it cool though, I didn't want to fuck this up at all. I hoped up from the chair and grabbed our last movie for the night. Black Swan. Never seen it, but I was curious so I popped it in as she came back. Without saying a word we resumed our old positions on the couch and I hit play.

I couldn't help but watch her more than I watched the movie, she was absolutely stunning and she was very nearly sitting on my lap. I thought that my glances at her had been sneaky enough, but around the 20th or so time she finally turned to face me as I looked at her. She asked if anything was wrong and I as I started to answer her I felt her slide her legs up and down my thighs. I choked on my words and she tilted her head and asked what was wrong. I gave her a playful glare and slipped my hand under her right foot. Her eyes went wide.

"Nothing" I said as I tickled her bare foot. She instantly started laughing and flailing her feet to get away from my fingers. I wrapped my other hand around her ankle to stop her violent flailing and continued to tickle her feet through the black stockings she wore. She was now laughing hysterically and practically heaving as she tried to push me and get her foot free. Her glasses finally came off and her hair was now a static-y mess from rubbing against my couch but I persisted in my attack. She finally started kicking my shoulder with her left foot, but I countered by quickly leaning forward and slamming back onto her foot when it was caught between my back and the couch. I stopped tickling her foot but I didn't let it go. She was now lying on her back, with the pillows strewn everywhere, and looking up at me whimpering slightly. With those watery hazel eyes, now extra watery and a puffy red from all the laughing. We stared at each other like this for a long while. Beads of sweat beginning to form on both of our bodies as we sat there and looked at each other. She suddenly yanked her foot away and got right up in my face, inches away from my lips.

"I'll be right back" was all she said.

She hopped off the couch and quickly ran to my bathroom. I was a little perplexed at the whole ordeal but I sat silently and waited for her to come back. About 30 seconds later she walked back into the room, but something was much different about her and I couldn't quite put my finger on it. She quickly sat down on the couch next to me and glanced at me, almost as if searching for some kind of reassurance. Then it hit me like a ton of bricks. She'd taken her stockings off. My look of shock made her smile and she hopped up and sat directly on top of my lap. I was in utter disbelief at this point. She was actually doing this. I grabbed her hips to steady her and scooted the both of us forward toward the edge of the seat. My cock was quickly becoming harder and harder as I felt her small butt roll around on the top of my lap. Her breathing had become much deeper and I found myself once again enthralled in her breathing, which made my dick even harder. She pressed her heels against my shins and shimmied them apart with surprising strength which made my cock harder. Then she pressed her hands against my pants and maneuvered my cock out of the hole in my pajama bottoms, pressing it directly against her butt and making it EVEN harder. Then she sat up slightly and shimmied her skirt up above her waist, pressing my dick against wetness. Soft, squishy, warm wetness. Fleshy wetness. She'd taken off her panties as well. I felt the tip of my cock right at her opening. She felt it too because she shivered and let out a loud long moan. With the tip of my cock pressed against her opening I squeezed my eyes shut, clenched her arms and held her there. She whined and rolled her waist against my cock, but I lifted her up, stood myself up, pressed myself against her back and whispered into her ear.

"Let me do something for you first."

She was breathing heavily and trembling hard, but she turned her head and nodded slightly. I laid her on the couch and quickly removed her skirt, baring her glistening pussy to me. I saw her shut her eyes and cover them with her hands, whimpered in what I'm guessing was embarrassment. I asked her if it was ok and she opened her fingers and stared at me with those watery hazel eyes, nodding her head. I dove into her wetness and set to kissing, licking, nibbling, sucking, and lapping up every inch of it I could reach. She moaned loudly and often, bucking her hips hard into my face whenever I reached a particularly sensitive spot and softly whispering "right there" or "harder" or "faster." Her being so small allowed my tongue to lap up all of her wetness whenever I felt like licking all of it off. Her bucking and trembling became more and more violent and her breathing became shorter and shorter. As a sort of finale, I whetted two of my fingers and slowly started to finger her while I used my tongue to softly lick on and around her clit. I looked up to see the effect this was having. Her eyes were shut tight and her lips were forming an "O" shape as her moans became louder and shorter. Her hands were grabbing at her chest and grabbing my hair, pushing me harder and harder against her. I suddenly saw her eyes open wide and roll up into her head. She and her body screamed as her orgasm tore through her for a solid 25 seconds, finally leaving her limp and splayed on my couch. I stood up and she opened her eyes to look at me. I was worried she might be regretting what we did, but before I could say a thing she crawled onto the floor and shoved my cock into her mouth. I was still sitting there trying to find the words to ask if if she was ok when my body was overcome with an enormous wave of pleasure. She was sucking me off like I was fast melting popsicle. Her tongue snaking it's way under my cock, then over it, then against the tip of it and damn near into it. Her mouth was small enough that I could slightly feel her teeth rub against the tip when she brought it in, but it was an amazing feeling against the tip of my cock. She then looked up at me as I watched her and I could tell she was grinning a mischievous little grin while my cock was in her mouth.

After another few minutes of what was easily the best blowjob of my life up to that point, she finally popped me out of her mouth and promptly sat me down on the edge of my couch. She finally took off her shirt and her bra, revealing the greatest set of A cup tits I've ever seen, and then climbed onto me and quickly guided my cock deep into her pussy. As tight as it was for me, it must've been 3 times as tight feeling for her, because the second I was buried to the hilt her eyes widened and rolled. She grabbed my shoulders, trembling hard, to steady herself and I thought up something incredibly hot. As her gaze focused and she rolled her head back to face mine I quickly grabbed her, picked her up with my cock still inside her, wrapped her legs around my waist and fucked her standing. Her moans came out of tiny screams as my cock reached further and further inside her. Her fingernails were scratching my shoulders and my back as she fought to stay propped up. Her legs gripped my back tighter and tighter, eventually forcing me to lay her down on my couches armrest where I continued to fuck her senseless. I felt myself growing closer and closer to an orgasm and stupidly I picked now of all times to remember my condoms. Almost like a psychic, she grabbed my arm and screamed for me to cum inside her. I was about to ask her about the pill when she followed up with the fact that she was on it. I think the idea of cumming inside of her bareback, coupled with all the teasing from earlier in the night finally pushed me over. I felt my legs tense as her legs gripped me against her (resolute in keeping me there until the very end) and I felt my orgasm explode out of me and deep into her waiting and welcoming pussy. I shut my eyes and moaned loudly as I released what felt like a gallon of cum deep into her and I completely missed the fact that she was cumming too. Shot after shot met contraction after contraction as she milked my cock dry and left me crumpled on the floor with my heading resting against her knee.

Following this, we agreed to start dating one another and ended up having even more eventful encounters spread throughout the span of a year and a half! Unfortunately, we decided to break it off after she decided to study abroad for a year and it became clear that even after her trip was done she would be transferring schools to continue her program elsewhere. We keep in touch though, and her eyes are still as watery and hazel as the day I met her.