Long time lurker, first time poster because I figure in an effort to remember these exciting encounters that are now years behind me I should at least write *one* of them here before it’s a lost memory.
When I was in my early twenties I had a bit of a wild ride (pun intended) with dating and hook-up culture. I spent my adolescence being the social nerd, a goody-two-shoes, girl-next-door type that no one was interested in, despite my yearning… and then suddenly, without warning, in my twenties guys were interested in me. I didn’t feel like I had changed at all, so I was a bit blindsided by the attention. Physically I suppose I was bustier than most but I was had never really lacked in that department, as was proven by the boys in high school who would stare at my chest rather than look at my face. Maybe more time on this planet gave me confidence? Maybe I finally got over my ex? Who knows.
Whatever it was, suddenly encounters with friends of friends or acquaintances at parties were getting very flirty, guys I had gone to school with were asking me out, and I had more matches on Tinder than I knew what to do with. (That’s hardly bragging, though, most women have more matches on apps than they know what to do with.)
To be clear, I am not saying any of this to be smug. I am not nor have ever been conventionally hot. Most people would call me “cute,” which used to irk me to no end. Additionally, I was MISERABLY lonely and pining for love in my twenties before I met my husband, so it’s not like this was all fun and games. But, some of it was fun, and there were games to be had…
This story is 100% true, although anonymized.
—
INTRO
Rewind almost ten years to my early 20’s. I was at my favorite music festival and having a blast, drinking, dancing, and just enjoying my summer vacation with my friends on a rare weekend we all were together. One of the days I was there, I unexpectedly ran into an old coworker of mine, we can call him Jake. He was roughly ten years older than me and I looked up to him like an older brother. At our job, we had spent hours spilling our guts out while we worked, and although there was some sexual tension, we were ultimately just pals. In those long shifts I had heard all about his best friend, Peter, and their antics over the years. Jake happened to be there at the festival with the legendary Peter, and they were off their ass on LSD, which considering it was a festival wasn’t all that out of place despite it being midday.
I was surprised to meet Peter because he was my type of guy. He was tall, quick-witted, bearded, and sporting a man bun… all of which was made at least 40% hotter by his Australian accent. I had never seen a photo of him but was impressed with how handsome Jake’s friend was. I was SO excited to see Jake, so I asked Peter to take a few photos of me and Jake with my phone. I was wearing a black cropped tank top that hardly hid a neon pink push-up bra and a healthy amount of cleavage. I also had on a pair of my infamous super skin tight skinny jeans that emphasized my very long legs (as I’m quite tall), and Nike Air Force 1s. My chestnut hair was long and straightened and I was covered in an unintentional concoction of glitter, sunscreen, and other people’s sweat.
I’m an absurdly observant person and I noticed *immediately* that Peter seemed to really take in how I looked. Jake did, too, probably because it was the most skin he had ever seen on me – even at work parties I was never showing cleavage. To illustrate this point, there was one time our colleagues dragged me to a club to celebrate a birthday and I was literally wearing a sweater, jeans, and boots… so you get the idea. I was happy to blend in as “one of the guys,” even if I was treated more as if I were a close friend’s little sister to them—they were protective of me, but also flirty with me, albeit never to a point where I felt uncomfortable. I didn’t mind it at all.
Jake hugged me for our photo and I was self conscious of how on display I felt. Here I was: single, ten years their junior, hanging out with two guys who had a slight look of appreciation among the intoxication in their eyes. It was titillating.
Jake’s hands lingered on me as we hugged for the photo and even afterward, and Peter’s rough hands touched mine for just a second too long when he gave me back my phone. I sat down with them for a while, and although my friend Jake seemed fairly out of it, Peter still seemed sharp and like he had complete control of the situation. He kept giving me this particular smile as if he knew something I didn’t, which I just chalked up to the drugs. He had this super sexy lopsided grin accentuated by his foreign accent that still lingered despite years of being away from home. We casually flirted as the energy between us seemed to ignite with the hint of sex appeal. I didn’t think much of it, I’d never see him again after this weekend, anyway.
Eventually, we parted ways and vowed to meet up again the next day. That night, after an incredible time dancing with strangers (read as: grinding with drunk college boys who kept buying me beers) to some of my favorite artists, I made it back to my friends. Going through my camera roll for social media I found that prior to taking the photos of me and Jake, Peter had taken a few selfies. They made me smile, and my heart fluttered like when a crush signs onto AIM (dated reference, I know, but apt if you’ve ever experienced it!) I felt that was a bold move, and I was impressed at his quick thinking.
I went to text Jake about meeting up tomorrow and he said his phone was going to die, so I should text Peter, and gave me Peter’s number. I don’t know if he was intentionally trying to give me and Peter a way to connect, or if it was coincidence. We never did end up meeting up the next day, but either way it definitely worked out for me…
—
THE BUILD UP
After that point, Peter and I would just randomly text one another about various things. It was always flirtatious but never crossed the boundary into being overtly sexual.
That is, until one night when I was really, REALLY horny after being stood up by a previous one-night-stand at a party. (He made out with me on our way from our mutual friend’s house to the bar we were all headed to together by pulling me into an alley and up against the wall, got me all hot and bothered, and then later left for the night! Cue Michelle Tanner’s “How rude!” But in retrospect, he was an asshat and I was only making out with him because I liked the attention. It worked out for the best; I don’t think I ever saw him again.) I somehow ended up tipsily texting Peter at some ungodly hour. I was annoyed that this one night stand’s moves had given off a vibe to the other guys that I was his, so they all backed off. I had no outlet for my frustration and as a shot in the dark tried Peter, who I knew kept bizarre hours.
It started innocent enough but pretty quickly turned into a conversation about our kinks. I’ve always had a healthy sexual appetite, even as a teenager, despite being passed over by all the guys at my school (which frankly was probably the best case scenario as they were worse than the mean girls you expect in high school). For as long as I’ve known how to masturbate, I’ve been really into the idea of being submissive and being used to fulfill someone else’s desires. Naturally, this came up as I was still tipsy and figured he seemed like he’d be into some fun things himself.
Much to my surprise, Peter said he’s into being rough and in charge, and that he wanted nothing more than to pin me down and use me, if I’d be comfortable with that. Mind you, the sun was rising at this point and I was on the couch at my friend’s place with people asleep all around me, so I couldn’t touch myself despite the fact that I had an incredibly intense feeling of warmth and wetness that I wanted to explore while imagining him inside of me.
I don’t remember how we ended the conversation, but I believe I had begged him to come visit me. At the time, I was living in the suburbs of a major city and he was living with Jake while he was temporarily between apartments in said major city. I was going to be moving in less than a week to a different city altogether and he wasn’t going to be here when I got back, so our window of opportunity was fleeting. It seemed like an impossibility, and I knew that this would likely just became a scenario I’d endlessly fantasize about because it would never happen, so I didn’t think much of teasing him with the possibility.
Over the next few days, I kept texting him tantalizing photos of myself. I’ve never sent a full-on nude photo, MTV’s “Catfish” made me paranoid about that, but I’ve certainly teased my fair share of guys with suggestive photos. I had just recently chopped my hair into an edgy bob and dyed it purple, and I had been working out a bunch, so I had this confident and indestructible hot girl vibe going for me at the time. I’d bite my lip and take a photo of my clothed yet ample cleavage, or send a photo of me in just a t-shirt at a full length mirror before bed. I think I got him worked up enough that he decided to make it work; he was going to figure out a way to get to me.
—
THE MAIN EVENT
When Peter showed up next Thursday night, I think we were both feeling awkward as we hugged hello. Here he was… a friend of a friend, who on a whim decided to travel like two hours to have casual sex with a younger woman that he had met exactly once before. The reality of the situation was sobering for both of us.
I had dressed to seem like this was no big deal to me, but I also wanted to be subtly irresistible, like subliminal messaging for his hormones. I had no intention of wasting this opportunity. I wore a crop top graphic t-shirt, my shortest shorts with pockets longer than the shorts themselves and that exposed the bottom part of my cute ass, both concealing a matching black lace bralette and thong. He was wearing a t-shirt and jeans, also achieving a “no big deal” look, and carried a small backpack with his belongings for the night. We drove to a bar and had a drink or two, just to get reacquainted (and I really, really needed the mental lubrication because I was nervous!)
The conversation was actually really easy and Peter was fun to talk to. The beer eased the awkwardness and we learned more about one another as actual people in the world. He flirted with the Irish bartender but in a casual, European way and flirted with me in a confident “we’re totally fucking later” way. I felt comfortable with him, maybe it was because he was best friends with my buddy Jake, but I really felt like I could trust him. You don’t often get that with guys you’ve just met, especially if they’re from the internet, so I knew this was going to “hit different” to use today’s parlance.
He drove us back to my place and used my computer to put on some music. After lighting some candles and lowering the lights, I stood next to him at my desk chair as he browsed our listening options, and he lightly grazed his fingers across my long, smooth legs. After picking the music, he pulled me onto his lap at the desk, my back to his chest, both of us “looking at music” while internally I was waiting with anticipation of what was going to happen, how this would all start.
Peter turned his attention from the music onto me, and traced his fingers up my legs to my ass, which he could feel because of how short my shorts were. He purred a satisfied approval in my ear, that I was a good girl for wearing those shorts. I basically melted right there.
Peter was a big guy, barrel-chested and tattooed with a necklace and some rings. He was strong, he was dexterous, and he had that fucking accent and his adorable, boyish smile.
While I was on his lap, he asked if he could take a picture of us to send to Jake. He explained that Jake didn’t know where he was, just that he was out for the night. I hesitantly agreed… I felt it might be awkward for Jake to know that I was hooking up with Peter, but at the same time, kind of hot in a way. And I loved that Peter wanted to show him. I liked that maybe he was bragging, and that made me kind of smug even if it made me a bit uncomfortable. He kept one hand on my ass (not visible in the frame) as we posed for the selfie. He sent it, and then immediately resumed. To this day I have no idea what Jake’s response was!
Peter lifted me up and led me onto the couch, got on top of me, and we made out for as long as we could stand. He was an excellent kisser. With ten years more experience it was pretty clear he knew what he was doing, and I was enjoying every second of it. His teeth found my bottom lip and I involuntarily moaned when he bit it. Our breathing got heavier and we got handsy, finally exploring one another until he wrapped a hand around my throat, gentle but with enough pressure to make me squirm with the anticipation of what he might have in store for me. Against my leg, I could tell he was already rock hard under his jeans. I couldn’t help but smile with a little satisfaction.
He briefly came up for air long enough to pull me into the bedroom. He pushed me onto the bed, face down, and with a hand keeping me in place recited a few rules: He was only going to do anything with my consent, so if I was uncomfortable then I was to let him know and he would stop. He would wear a condom any time he entered me. I was to do as he said when he said it. And I was to thank him for each spank I was about to receive. I gasped at that last part. By this point, my thong was entirely soaked, and I wanted him in me so fucking bad that I started whimpering as he pushed my body harder into the bed and held my hands against my back.
He pulled down my shorts, removed my thong, and cupped my ass appreciatively. He seemed to be enjoying the view of a younger woman in front of him, legs spread and laid against a bed for him to use. I took great pleasure in being the thing he was admiring. He even growled a little with anticipation, a primal sound that made me giddy with excitement of what would happen next. He then began to spank me. I said “thank you,” and he insisted I was to say “thank you, sir.” So I did, my face burning with humiliation. I had never been with a man who required me to call him “sir” before. He spanked me over and over and each time, I thanked him for doing so, although I could feel how tender my ass was getting and how much wetter I was becoming. He expressed his appreciation for how fast my ass turned pink at his touch while gently caressing me.
Without warning, he flipped me over and seemed to be appreciating the sight of me in front of him some more. I had shaved myself almost entirely, and I was painfully aware of how I was now on full display, anticipating his next move. He pulled my shirt off of me and expertly unhooked my bra while I hoisted his own shirt off and over his head. I started to unclasp his jeans but he stopped me, telling me not to rush it, I’d be taking care of him later. Internally, I swooned.
He pulled my hips toward him in one swift move and reached one hand for my right nipple, the other firmly holding my hips in place as he bent down and teased me with his tongue. He started with my inner thighs, working his way up to my labia and gently tickling me with his mouth. I was whimpering at this point, I wanted him to make me climax so badly. He paused and told me that he’d go as slow as he wanted to go, and if I kept making noise he would stop altogether. That shut me up REAL quick. He placed a pillow under my hips for a better angle and resumed his teasing.
After an excruciatingly long time, he finally went for it, using both strong hands to hold me at the right angle for him to lean into me. His beard tickled but ultimately felt good as he licked my clit, and entirely honestly I have no idea what he did to me but it felt mind-blowingly incredible. It was the best oral sex I had experienced up to that point, and despite my downstairs neighbors, I was moaning loudly because I couldn’t remember they even existed.
He could tell I was getting ready to climax on his face because I got quiet and my body tensed up, so he pulled himself up and gave me that devilish grin again, glistening this time with my wetness in the candlelight, when I looked up in horror.
“How badly do you want me in you?” He said, two fingers teasing me and continuing to look me straight on. I felt silly saying the words out loud, but I conceded.
“I want you so fucking badly. I want you to fill me up.”
“Good girl,” he replied, as he once again maneuvered me into a position of his pleasing. I was now fully naked, kneeling on the bed with my ass up, waiting for him. Behind me, he pulled off his jeans and boxer briefs, slipped on a condom, and crawled up onto the bed to kneel behind me. He gripped onto my hips and proceeded to grind his hard dick against me without entering me. He commanded me to beg for it. I whimpered again, wishing I didn’t have to speak and that he could just read my mind.
I blushed as I pleaded in a whimpering voice I hardly recognized, “Please, I want you inside me.”
“…Sir,” he said gruffly.
“Please, I want you inside me…sir.”
I am certain my face flushed red with embarrassment of having to say that out loud. Writing this out now I’m actually a bit flushed!
With that, he grabbed onto my hair with one hand, gripped my hip with the other, and slipped himself inside of me- an easier than normal task because of how wet I was from being teased so mercilessly. He grunted in a sexy, manly way as he felt me envelop him.
Peter started somewhat slow but forceful, pushing into me so I could feel his hard cock fill me entirely and his balls slap my clit as he thrust purposefully in and out. He was driving me crazy as he’d start to go faster, only to stop himself and slow down, giving me a second to catch my breath. After a few new stimuli (playing with my breasts, twisting my nipples, rubbing my clit, placing his big, strong hands around my throat) he eventually settled on holding me more upright and having me bounce up and down against his legs. My back was still to him, and he reached one hand up to cover my mouth as he whispered a growl in my ear, “I’m going to cum in you” and picked up the pace. That was enough to set me off, and I started screaming “fuck!” into the palm of his hand as he pulled me down onto him over and over while my muscles tightened and spasmed over him, finally culminating in a growl-like groan, a shudder, and a release from him.
After untangling ourselves from one another and cleaning up a little, we got back into bed and cuddled for a while, while he embraced me and told me how sexy I was. I truly felt it, flushed from the excitement of sexual synergy and having been used to his satisfaction.
After dressing and going for a quick excursion for a midnight snack, praying we wouldn’t run into anyone I knew as he fondled my ass in public while we waited for our order, we came back and quickly embarked on round two. This is where the details get hazy for me and events start to blur together because of how blissful it all was and how long it all went, we were up a significant portion of the night with him using me to his liking. This included me kneeled in front of him with him rewarding me with his cock in my mouth for my previous good behavior and his hands holding my head in place by my hair while he fucked my mouth and I swallowed every last drop of cum he gifted me.
Each time he had new requirements, and each time I would orgasm harder than before. I remember drifting to sleep with my head on his chest as I was so exhausted from the night’s activities, and he was stroking my hair, talking about philosophy and poetry. I was so content.
I distinctly recall being relieved and yet also regretful that I would be moving because I knew for sure I would develop feelings for him if we were to see each other again, and I didn’t want to do that… but also strangely mourned the lost opportunity. We were sexually compatible but definitely not meant to be together in any other way, and I’ve always had a hard time separating sex from real relationships so I knew continuing to see him would have been impossible for me. Although my heart was a little heavy, I fell asleep in his arms, and woke up still in his embrace.
—-
THE END
The next day, after a light breakfast we said our goodbyes. I kind of knew I’d never see him again but couldn’t help hoping maybe we’d get a second night of sexual bliss someday.
But, we never saw each other in person after that. When I moved I ended up meeting my now-husband in my new city, and Peter moved to the other side of the country where he met his now-fiancée.
I still fantasize about this night, and although I know he’s been with many more people than me, I hope he does too.
I don’t regret a thing!
Source: reddit.com/r/gonewildstories/comments/un1q4v/experienced_aussie_from_the_music_festival
Brilliant story and you surely write well.