first times and fuckups [MF] [21/18]

*NB: none of this is embellished, it’s written exactly how I remember it but it’s been a few years so some of the details are hazy. Names are changed to protect the not-so-innocent. All parties were adults at the time.*

EMILIA

This is a story about one of the ones that got away. The thing about Emilia is she was a freshman when I was in third year of design school, she was super smart which means she was freshly 18 and definitely inexperienced. I noticed her long dark hair, piercing blue eyes, and prominent cheekbones and clavicles in the studio fall semester but felt skeezy going after someone barely out of high school, so I didn’t. Her youthful runner’s build wasn’t what I typically was into, but she was so striking that I couldn’t look away. She must have caught me, because she was suddenly everywhere I needed to be and it couldn’t have been coincidental. She pursued me without really knowing how. I later found out she never had a boyfriend, had barely been kissed, but the magnetic attraction I had to her was mutual.

The first time we hooked up was after a late night in studio that, like many, included some secret booze. I walked her home to the freshman girls’ dorm across campus. I totally felt like a predator despite her invitations, having been at school a few years at this point and having more partners. I wanted her to take the lead to ensure she was comfortable, and we climbed into her loft bed with our underwear on, her erect, puffy nipples poking through a thin tank top. She was shaking when we kissed. She had so much built up passion from her hard-driving parents and academic upbringing that her entire body was vibrating against me, smooth pale skin and lanky limbs with a growing wet spot in both her cotton underwear and mine. I asked if I could touch her and she nodded, eyes half closed, mouth in a silent O, and I let my fingertips explore her body. Dark freckles on pale skin. Lithe muscle just beneath the surface. Abs clenching as she twitched when my hand drifted to the crest of her hips and below her belly. I hadn’t even touched her pussy yet but her nipples were threatening to shred her shirt. She gasped when I circled her small tits, spiraling slowly toward the nipple like Robert Smithson in the Great Salt Lake. When I ventured beneath her soaked panties she began to haltingly gasp and I soon realized she was almost on the edge of orgasm just from me lightly stroking her vulva, then parting her labia and teasingly dipping a fingertip into her slick heat. I had barely raised a slippery middle finger to her clit when her hips began to convulse, head thrown back, eyes wide open. I can’t take any credit for that orgasm, that was years of repression finally finding an outlet.

I didn’t cum that night. After Emilia came she was completely spent so I held her until she was sound asleep and then slipped out. I’m sure I blew a massive load once I got home but I was beyond elated to have given her that experience. She definitely made up for it soon after when she became orally obsessed. She must have watched a ton of porn because she started giving me the filthiest blowjobs, aggressively deep throating me, slapping her face with my cock, and using tricks I’d never experienced before— some of which were not my thing. But she was a quick study and took critique well, and soon she knew exactly how to edge me with her hands and mouth, how I liked my balls sucked, and the perfect switchy blend of needy and dominant to make me drip, then demand I cum on her face. It was a fucking dream.

If I could ever get my dick out of her mouth and her pants off, I was greeted with one of those archetypal tiny, tight little pussies that some of us grew up seeing only in magazines we’d find stashed in the woods. Just a fuzzy, puffy peach no longer than a finger, oozing with the sweetest clear nectar.

I know, I know. Guys like to hyperbolize vaginal secretions. I am not afraid to say they’re not always pleasant, often on a scale from tart to pungent and sometimes, unfortunately, beyond. Texture and color varies as any vagina owner knows, but for the most part spreading Emilia’s cunt was like opening a can of ripe peaches and letting the heavy syrup drip onto my tongue. Her hypersensitivity from our first time subsided thankfully, and she was soon able to enjoy me edging her orally almost as much as I enjoyed teasing and tasting her. I can still see her eyes half closed, brows raised, and lips curled in a particular way as she approached orgasm from the days I spent between her legs.

Eventually, after some time of careful fingering and gentle escalation, I was willing to try penetrating her. I knew she was a virgin and there was the whole emotional and societal baggage around that, plus she was just really fucking tight even if she just came. Like one finger tight. When we finally tried it, we teased each other orally for a while, then I laid her on her back and slowly licked her to orgasm before placing my tip at her entrance and letting her wrap her legs around my back. I wanted her to pull me in, to control the depth. Which she did, millimeter by millimeter. I felt her spreading, stretching, clenching around me like I never had with other partners, and I saw the emotions flooding across her face inches from mine. It’s still one of the most intimate things I’ve ever done. I experienced relativity firsthand when it felt like it took most of an hour to fully enter her, and then we stayed that way, bodily entwined and feeling each other’s pulse through our most private extents. With how tight she was I couldn’t really stroke or thrust without being worried about hurting her or making myself cum too soon, so we let our hips engage in conversation with a rhythmic call and response— press, grind, release.

Honestly I don’t remember her coming that first time, but I know her grin went wide when she felt me start pulsing and unloading inside the condom. Perfect white teeth and a deep belly laugh. I fucking loved her.

We hooked up on and off for a few years, but it always felt like we had the worst timing and we were just ships passing in the night, meeting up for a weekend romp but never living in the same place or, in our youth, emotionally ready to commit to each other. Sometimes our text thread would turn from memes and ranting about our industry to sexual stuff, then she’d be on my doorstep in a dress with nothing underneath, and five minutes later I’m covered from ear to ear in her delicious wetness.

The mistake I made with Emilia was having a plan for both of our best interests, but failing to communicate that to her. Because she had never dated anyone nor had sex with anyone else I knew if we started dating that we’d get married. We had that type of chemistry. What I meant was for her to casually date a couple other guys, get some life experience under her belt, and then come back to me forever. But I fucked up and what I think she heard was that I didn’t want to be with her, not that I wanted us to see other people temporarily. I was crushed, I still think about how badly that went, but I think she’s happy and I’m not a home wrecker.

Source: reddit.com/r/gonewildstories/comments/ucio0p/first_times_and_fuckups_mf_2118