Diary of a Cadet Ch.4: Our First Time [MF] [F18] [18,18] – Short Sex Story

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Hey everyone! Welcome to my first time writing about actual, full blow, sex. Chase and I’s first time together, and the first time I’d spent the whole night in the arms of a lover. I hope you enjoy this one as much as I do! <3 Taylor

Chase had touched me. I had given him oral in the woods. He had cum all over a thong I’d given him. We were a couple. Two months at military school had gone places I hadn’t even remotely imagined it would go. Parents weekend was here in a flash, a milestone I never wondered I’d reach in some of my lowest moments here at college that I wouldn’t have reached without the support of Julie and Chase. My parents weren’t able to make it up, but I was quickly adopted by Julie’s mom and dad who are truly saints. Parents weekend passed with the excitement of marching in a ordinary parade of the entire corps of cadets, a tailgate on the parade field and going watch our football team play after marching the corps into the stadium and into the stands. Julie’s parents had made friends with Chase’s mom since we all kinda forced the group together as we finally got to let our hair figuratively down. Since the groups of parents were joined at the hip, when it came time to tour barracks, I found Chase’s mom standing in front of the neatly made bed that days ago I’d posed in my underwear to take pictures for her son. I struggled to hide my blush. We also got the chance to go out to dinner Friday and Saturday night, our first real meals outside of dining hall meals with Cadre or delivery drop off in our rooms. It was genuinely a great weekend and it gave me a wondered about how to finally have my night with Chase that I so desperately wanted.

When my college has special events, restrictions get lifted for brief periods so that family and friends can actually enjoy time with their cadets, regardless of what class we’re in and the privileges we’re normally entitled to. The next big event after parents weekend is Homecoming. It’s not a massive thing at every school, but at mine, it’s the big deep breath half way through fall term. And on Saturday night, if you go to the dance for a specified period of time, you’re entitled to go out with your date for the night within the County our college is located in. Julie is really the one who hatched our plan. She had two friends from high college that went to a school down the road, both of whom had boyfriends. If Julie and I wanted a night away with our boyfriends that we couldn’t take to the dance, we would just need boyfriends, and our boyfriends would need girlfriends. Julie messaged her friends Elise and Anne, both of whom, upon hearing the predicament we were in and agreed to help as long as we got the hotel rooms for the weekend. It would be fun! In short, Elise and Anne’s boyfriends would sit with Julie and I at a football game and Chase and Eric would sit with Elise and Ann and then at the dance, we would pose for pics at the door with our respective partners, let everyone mix around at the dance, and then leave as a group and go to the hotel with the correct people. A little complicated, but we’re all genuinely good friends, so what’s a little complicated to help a friend? Besides, with our college’s zeal for enforcement of PDA rules, it’s not like anyone was gonna be messing around or doing any funny company.

With the plan figured out, there was just the matter of waiting 2 long weeks before we finally got to have our chance. Cadre, college (midterms the week before homecoming), and cross country practice and a meet kept our noses to the grind stone, and nothing really substantial happened between Chase and I. But that was substantial itself. It was a period where we learned about eachother, endured struggles together, and pushed eachother to not only make it through, but to excel in the classroom and in our military school lives. On top of learning about eachother, our little quirks, more of our dreams and goals, we also took time to learn about eachother sexually as well.

Sitting in the library late one evening, the conversation turned to sex. Not like “omg let’s do it right now”, but more of the genuine curiosity of two people, both relatively new to having sex, wanting to learn about eachother’s experiences, likes and dislikes. Chase went first. Unsurprisingly for a band kid, Chase was pretty inexperienced on the dating front. He had had 1 girlfriend in high college, for a little over a year, from the middle of sophomore year to just before summer of junior year. They had messed around a little, but it wasn’t until junior prom that he had had sex for the first time, your ordinary discover an empty bedroom at the afterparty. Chase told me that they’d done it a few more times at her house in the weeks that followed but then the relationship ended and he spent senior year fully focused on trying to get an air force scholarship, and then come to military school totally focused on his career, not unlike my own goals. I learned that Chase isn’t a massive adult entertainment viewer, and genuinely enjoys casual but sexy in everyday situations to get him going.

For my own half of the experience story, I told him about the 3 guys I’d dated, a quick mistake of a relationship freshman year that nothing happened with, dating a Senior my sophomore year whom I’d lost my virginity to after his prom in the back of his mom’s minivan, and my final, more successful relationship my senior year with a guy from my cross country team that I actually got to explore a bit of my sexuality with, before we ultimately decided that school cross country careers on opposite coasts of the country probably wouldn’t work out. I told him that one of my biggest turnons is teasing, especially through pictures. While I’m not entirely comfortable emailing him pictures of myself, it’s the medium we have to live with for 4 more months until we get to have our phones again, and I trust Chase to respect what I chose to distribute only with him. We both agree that we have some growing and learning to do in the sexual realm, and we decide it’d be healthy to spend some time candidly talking about our experiences together from time to time as we go along this wild ride together.

Homecoming weekend was finally here. Friday had parade #1 and dinner with our friends, Saturday would bring parade #2, tailgating and football game, a dance with our fake dates and then…finally. Chase. The Friday parade passed without incident, Julie’s friends, Elise and Anne as well as their boyfriends were all genuinely impressed and treated us to a lovely dinner out. The entire time, I imagined being out on a date with just Chase, the two of us at some romantic, candlelit dinner and he sweeps me off my feet as we return and he takes me to bed for dessert. A girl can long for things…just a few more months to January…just a few more hours to Chase. When Julie and I make it back to our room Friday night, my mind reaches back to Chase talking about loving casual nudity in typical settings being a turn on for him. I flip open my laptop and point it towards the corner of our room that has my wall locker, desk and bed and I tell Julie to stay on her side of the room unless she wants Chase to see her silly unicorn print panties one of her friends had sent her as a gag gift to military school that she now occasionally rocks under her black spandex in a quiet display of individual expression.

Julie bursts out laughing when she realizes what I’m doing, “oh my God you little horndog, you’re letting him watch you get dressed for bed now” she spits out through genuine fits of laughter. “God I thought I wanted it bad but geez girl, go on and give Chase a show”. I press record on the video camera of my laptop and start to unbutton my dress shirt and unbuckel and unzip my pants.

“Girl, if I wanted to give Chase a show, I wouldn’t do it with you here” I say to my best friend, a figue outside the camera’s view. She replies that “it’s fine hun, I know I’ve shared more than my fair share of naughtier things than this with Eric while you’re at practice and I have the room to myself” I blush bright red, knowing Chase will hear that when he watches this video as my pants, spandex and generic black bikini cut panties come down in one quick motion and I lift my white undershirt over my head, continuing the conversation in only a plain white sports bra as I turn around, my bare butt to the camera as I look for the grey sweatpants I generally sleep in. I grab them and a plain pair of white, bikini cut panties out of the drawer after bending over slightly, giving Chase a teasing view of my butt in an appealing position. I turn back to face my laptop, Chase getting a full frontal nude view of my thin, muscular body that is currently devoid of any excess hair “down there” in preparation for fun after the dance. I’m slightly self conscious about my smaller, B Cup breasts when even my own roommate beats me in that category. Some of the outfits Julie is able to wear with a full C just don’t look right when I try myself. But on the other hand, I can go braless in situations she cannot so…you win some you lose some, and despite my own body consciousness, Chase is absolutely winning as he gets to watch this all unfold. I slip the sports bra over my head, momentarily nude until I quickly pull on the underwear and sweats, making some bit of modesty before I lean down to the camera, my small breasts hanging free and tell Chase through the lense “try not to use up everything in my thong tonight ” slyly referring to the panties I gave him after the library that he now sometimes masturbates with. Julie catches the phrase that I wondered only the camera would hear “Taylor!!!! You slut!” Julie laughes and yells at me from across the room. She yells to the camera “Chase you get your butt over here and give my wife back her lady things” I absolutely lose my shit laughing, oblivious to the fact that I’m still currently topless and outside the camera’s view, Julie is dressed for bed in a tshirt and underwear and not much else. I quickly slip on a cross country shirt to sleep in and blow a kiss to the camera, wishing Chase goodnight before turning off the camera and getting into bed. I send the video over to Chase with a quick note telling him to enjoy (;

Homecoming day is go go go from the begin. Breakfast formation, March down to the meal with random alumni, families and dates taking pictures like this is something special rather than how we all get to meals twice a day. Parade, is followed by a quick change into our standard white pants, white shirt with a black zip up duty jacket to fend off the cool fall breeze for tailgating with Julie’s friends and their boyfriends aka our dates. We all hang out, having lunch off a grill that Kyle had packed in his truck while Evan jokes around with everyone that we’re all about to be an 8 way family after tonight. This is almost true. Elise and Anne are still around, with Julie, Chase, Eric and I. Sadly but not really, Kyle and Evan don’t make it to Christmas because Elise and Anne are nowadays a couple, not just friends. Still the atmosphere is light as we have lunch in the field, blending in with the crowd of 1600 other cadets doing the exact same thing. The football game brings us a rare glimpse of our team actually winning a game and before long its time to dance.

Uniform for homecoming is the same as for class, with the exception that girls may choose to wear the knee length white uniform skirt instead of pants if they so choose. Julie and I both opt for the modest skirt and black low heels option with our short sleeve button down dress shirts, my thick curly hair pulled back into as neat of a bun as I can manage, and soon we are out to the door and off to the large open gym that’s been converted to a dance hall for the evening, decorated by the cadet event staff and DJ’d by a local talent that actually is pretty good and sets the mood to let our hair down and just be school kids. I’m jealous of the mid thigh length party dresses that Anne and Elise get to wear and am super jealous to see Anne on Chase’s arm as we walk into the venue as a group. I cannot really complain though, walking in on the arm of a handsome collegiate lacrosse player, Kyle, of course rocking khaki pants and a smartly tailored navy sport coat. Julie and Evan look equally at home together but you can tell she is slightly jealous that Elise gets to walk on the arm of her Eric. Walking in, we see a few heads turning from upper classmen that are shocked thay some freshman actually have dates that don’t look like they’re highschool girlfriends that are…still in highschool. No one suspects that we’re anything but a group of friends hanging out with our dates. Certainly no funny company here. We get in a few dances to some upbeat club music followed by a variety of country bar tunes and back again, the DJ catering to all tastes. When the magic allotted minimum time hits so we can leave and take the night off campus, about 1/3 of the couples, upperclassmen and freshmen, make for the door, while the rest finish out a genuinely fun dance at their own pace. We pile into Kyle’s truck and make for the hotel rooms that they checked into yesterday. We say our goodnights and four couples go to four rooms to finally have our night alone.

The door shuts and Chase and I drop our overnight bags by the door, quickly surveying the room with 2 queen beds. We don’t jump straight into anything wild, your girl has to pee lol it was a long dance. When I come out of the bathroom, my heart is racing in anticipation. Chase has already started to get comfortable, kicking off his shoes and socks while hanging his class shirt in the closet to keep it from getting wrinkled. As I step closer to him, not knowing how quickly we should move, Chase pulls me into his arms, lifts my chin to look into his dark brown eyes before planting kiss after kiss onto my lips. My arms are around his waist, my hands holding his back, pulling him close to me as our kisses deepen and and our tongues intertwine. After what seems like forever, we come up for air. Chase moves his hands to the zipper at the side of my plain white skirt, letting it drop to the floor, leaving me in a plain black athletic thong and my button down class shirt. Chase’s firm hands are holding my butt as he holds me close, my hands between us working to undo the buttons of my class shirt.

I pull away to remove the button down and hang it along with my skirt in the closet with Chase’s shirt. Chase removes his pants and hangs them up. And we soon discover ourselves in just our underwear, Chase in plain black boxer briefs, and me in a plain black pushup bra and simple black athletic thong. I giggle to Chase that “look hun, we match!” laughing at the accidental matching scheme that’s actually kinda unavoidable at military school. He laughs as he takes me into his arms, and I wrap my legs around his waist, his hands making their way to my nearly bare bum, his strong hands spreading my cheeks as my thong disappears down the middle and my lips discover his as I wrap my arms around his neck, kissing him passionately. I reach back and deftly unclasp my plain black bra with one hand, allowing it to fall between us, exposing my bare breasts to Chase for the first time in person. I toss it apart, my arms wrapped around his neck, as he kisses his way from my lips to behind my ear, trailing down my neck and to my chest as I lean my head back, my long curly hair falling away behind us as I expose myself more to his kisses as my breath quickens, my heart races and arousal builds between my legs.

Chase tosses me down to the bed before joining me on the pillows himself. There is a longing in our eyes, his brown, mine grey blue as we stare at eachother from across the pillow, smiling eagerly at our lover. I push Chase onto his back and start the same trail of kisses from his lips, to his chin, behind his ear and under his jaw, down his neck, across his tone chest and down his firm abs, stopping only at the top of his boxer briefs, where his firm arousal is evident as a buldge under the tight black fabric. I run a teasing hand across his front, gently gripping him, teasingly stroking him over his briefs as I sit on folded knees along side him, my small plain black athletic thong preserving my only bit of modesty. I kiss him softly on the lips as I reach into his underwear, stroking his firm six inches as I tease him into arousal. I break our kiss, hop off the bed and pull my panties to the floor, exposing myself to him fully for the first time. I feel the cold air of the room hardening my small, pink nipples into firm arousal. The wet folds between my legs make it impossible to hide my feelings there. My body is a mix of tan lines from uniforms and running clothes and a few left over from tanning over the summer. I’m toned and the strongest I’ve ever been in my life. Chase lifts up his butt, sliding his boxer briefs to his knees and I take them the rest of the way off before climbing up between his legs, preparing to tease him further with my mouth, wanting to draw our pleasure out as much as feasible.

As I crawl up between Chase’s legs, a firm hand reaches for my butt, grasping for one cheek and tugging it around to have me face away from Chase. Taking the hint, I lift one leg over Chase’s torso and back my now spread, exposed, soaking wet vagina up to Chase’s face, where his tongue eagerly greets my entrance, sending waves of pleasure through my core as the tip of his tongue finds the small bundle of nerves at the center of my pleasure. I almost forget myself in the moment, my hands on either side of my lover’s hips, supporting my weight as I lower myself onto his willing face. His own arousal is evident, right there below me and I drop to my elbows, taking him in one hand as I tease the tip of his manhood with an outstretched tongue. I run soft lines of pleasure with my tongue down his length, cupping his balls in my hand as I lick my way across every inch of his manhood, pausing to take each one in my mouth for a moment, an odd fleshy feeling that sends audible moans from Chase straight into my center where his tongue has not stopped its task of trying to lick me into heaven.

I take a breath before positioning Chase’s saliva coated penis in front of my lips, opening wide and swallowing as much of his shaft as the position with allow. Chase bucks his hips in pleasure, hitting the back of my throat and causing me to gag slightly before recomposing myself and I start to suck him in and out of my mouth in a rhythm imitating the rhythm I want to ride him to in a few short minutes. I feel his fingers spread me wide as one finger slips inside my soaking wet vagina as his tongue circles my clit. I’m so exposed, with both of my holes inches from Chase’s face and I am quickly building to an orgasm I didn’t know was about to break until suddenly a second finger slips inside me and it crashes through me like a wave against the shore. My inner walls clench around Chase’s fingers as I press my clit hard against Chase’s tongue, the friction drawing out even more pleasure and prolonging the pleasure of the orgasm that has me over the edge of bliss. At the same time, equally suprised by my sudden orgasm and hips thrusting myself onto his mouth, Chase bucks up his own hips, burying his shaft all the way into my throat with my lips pressed against his pubic bone, his penis all the way in my mouth. It shocks me and I start to gag, but the waves of pleasure coursing through me make me not want to adjust my position. I hold my face against his pubic bone, shaft down my throat as we both rock our hips mimicking the act yet to come as I ride my orgasm to its end before I lift up, red faced with long lines of drool coming from my mouth, coming down from one of the best orgasms of my life.

Getting up and grabbing a drink of water and wiping my mouth, I walk back over to Chase, naked and rock hard on the center of the bed and climb on top of him, this time aligning our hips, straddling him with my vagina, slick with arousal, rubbing along the shaft of his penis as I lean down, my long dark curly hair creating a veil around our faces as I kiss him passionately. I rock my hips teasingly, my slit rubbing my arousal up and down his shaft as Chase grips my buttcheeks, spreading me wide as our kisses continue. I lean up, peering down into Chase’s eyes as I reach between my legs, grasping his shaft and position his head at my entrance. I lower myself onto him, his length stretching me in methods that I haven’t felt in months and I’ve longed for since we first became romantically involved. I sink down, letting out a moan of pleasure as I lower myself until my lips meet his pubic bone, his shaft completely buried inside me, almost touching my cervix, the perfect fit. I lift myself up, his head almost slipping out of me before dropping back down again and again and again. Soon I’m bouncing up and down on Chase’s shaft as he reaches up, squeezing my B cup breasts as my nipples harden between his fingers. He squeezes as I ride, pulling me down to kiss my lips as I bury him deep inside and then grind my clit against his pubic bone without lifting up, stimulating my bundle of nerves while filled completely with his manhood.

Moments later Chase begins to thrust from underneath me. I’m on my knees, face buried in his neck as he grips my butt, spreading me wide and holding me in place as he begins to pound a rhythm faster and faster. My vagina clenched down around him, my orgasm breaking as I cry out, moaning for “Chase, Chase, Baby please don’t stop, please don’t stop” as I feel myself get noticeably wetter inside my core, releasing the pent up pleasure I’ve been begging for. In a moment of his own passion, Chase firmly grips my butt, squeezing hard as he buries himself in me and erupts in thick streams of passion deep inside me in a stream of one, two, three, and a fourth firm thrust as he fills me like I’ve never felt before.

I am utterly spent, breathless, sweating and covered in a musk of sex that comes from shared passion without a care. We lay there kissing for a few moments as Chase goes soft and slips out of me, releasing the mix of both of our orgasms out of me and onto the bed. We get up and shower together, each of us helping the other wash away the day and night we’ve just had. Afterwards, we spend the night watching TV, with Chase in some boxers, me in a big tshirt and bikini cut panties underneath before we fall asleep, Chase spooning behind me keeping me safe and clutching my breast in his hand.

The next morning, we meet our friends and return to Post, saying goodbye to Elise and Anne and thanking them for all of their help. When we get to our room, I have Julie spill the beans on her first time with Eric. “It wasn’t my first with him silly goose”…Jaw. Dropped. Since when were you holding out on me? I learned that during tailgating, the two of them had “gone to the bathroom ” and instead made their way to our room and had sex with Julie bent over the sink. Way to go girl! Also, thanks for giving me the idea to try with Chase! Overall it was a perfect weekend and opened doors for more later!

Thank you for reading! As at all times, I’d love to get your critiques as the story continues! Have a great day! <3 Taylor

NSFW: yes