Hi! I’m Cindy. I can’t believe it has been almost one whole year since I last posted a story on reddit. I work constantly and I barely have time to write longer stories these days, but even if it’s just for me I try to write a little every day because it helps me to remember my memories, if that makes sense. Due to world events I suddenly find myself with too much time, but at least I can finally write as much as I want and I have been really, really looking forward to remembering this particular experience! This is a true story about what happened between me and a guy I met online last spring. I’m sorry that it’s so long and mostly about exploring all my memories, I hope it’s not boring to read and I thank you in advance for being so patient with me!
I met Nathan online after I responded to one of his posts. Nathan was fairly local to me, which is somewhat unusual because I live in a small town and his town is pretty much just down the road. I’m divorced in my early 30s and at the time I was happy to be free of distracting, needy men. I put everything into forwarding my career and for a while it was okay, but when the spring arrived, I somehow became lonely and depressed. I know they say you’re only supposed to get depressed in the winter when it’s darker and miserable (at least where I live!) but last year it was really the opposite for me. When you work late, for me it feels better to leave the office when it’s already night, don’t know why, but when you leave work late and the sun is still only just setting, it only reminds me of a day wasted. I don’t really know how to explain it, but with the divorce and all that entailed it wasn’t easy for me to cope with normal life, especially when it seemed like everywhere I looked I saw happy families enjoying a beautiful summer. I felt like my life was slipping past me too quickly, I was missing out on something special, and the summer felt like it would be long and lonely for me.
Anyway, my social life at the time was mostly just chatting with guys on my phone late at night from under my downy covers, just before bed. To be honest, most of the time I fell asleep very disappointed and frustrated. I never messaged guys who lived anywhere even remotely near me just because I found it boring and not really part of the fantasy! For a little while I had a friend from Australia and another friend from Europe, but these kinds of friends tend to fizzle out pretty fast when the fun stuff wears off and personalities become part of the equation. I don’t know if that makes sense but that’s my experience with online “dating” for the most part. I have an old ex boyfriend that I would hook up with from time to time after my divorce but that was around the time I really started souring on his attitude too and it’s been ages now since we connected even in text. Otherwise I get my share of lingering gazes from men at work and the gym but I’m hardly ever approached by anyone beyond a smile and hello. I am a big smiler but I guess I also give off a bit of a standoffish vibe at the gym. At work I’m all professional and guys can tell, so while I sometimes notice when they are obviously admiring my butt or my legs or something nobody wants a harassment so I’m left alone all the time. I’ve only ever had one fling at work but that was a long time ago even before I started college.
So I decided to message Nathan not just because I was feeling lonely but also because he wrote a really funny post and I connected with it on a superficial level. We started messaging back and forth and had a really great conversation and it went really well! He is younger than me and he was barely finished with his college at the time, working in an office downtown and living in the same tiny studio apartment near his campus from when he was still a student. I don’t mind putting it out in the open that Nathan is a great conversational writer and he doesn’t ask annoying questions over and over and yet somehow he could keep me interested all the time. Most of my experience online is with guys trying to prove how smart they are or who otherwise seem to be performing in some way. Nathan is different. We eventually shared photos and long story short we had some video chats that were sexy and really funny too, we were both very nervous for some reason and kept making stupid jokes. We started on a thing where we had long conversations super late at night and I’d even fall asleep with the sun coming up and his voice in my ear as I drifted. On the negative side I had many days in a row where I didn’t get much sleep and only managed to get through my days by looking forward to break times, lunch naps, and rushing home to chat with Nathan and sharing a few moments with his smile and his voice before sleep.
Nathan wasn’t pushy about meeting even though we talked a lot about what would happen if we ever did. We both were taking things slow and I was much more into prolonging the fantasy with Nathan because I’ve learned sometimes that’s really the best part and the part that’s worth chasing and savoring. To me, Nathan was this nearby guy who represented everything I needed at the time, which if we’re being real means, in hindsight, I was guilty of some serious projection. We whispered late fantasies and promises night after night, until finally we had a conversation where it seemed somewhat repetitive and I think we both felt it. When we broke off that night, I remember thinking that perhaps these sorts of relationships can only end in frustration and that maybe I should just block his number and spare myself from whatever was next. I even cried quite a lot that night, before finally drifting off to sleep, though to be fair I was also really tired and at the end of my wits with so many things in my life.
Nathan texted me a few times after that weird conversation and I was very much prepared to look for any fault or reason to ignore him, but he said all the right things! In other words, he wasn’t pushy and didn’t keep giving me advice or instructions! I really hate that, you know! (Okay, sorry I will try to avoid venting my personal life into this post, but it’s funny how old emotions can come to the surface while exploring old memories, isn’t it?) Anyway, when I finally responded, I just texted to Nathan: “can we meet tomorrow for lunch?” I remember staring at my phone with this helpful, hopeful feeling that I’d be standing there forever waiting for a reply, but Nathan replied almost instantly with a big smiley face and after a few minutes we made a date.
Before we get to that part, can I just describe Nathan for a bit? In his post he didn’t really say much about his looks and it was mostly about his interests and stuff like that, so I wasn’t expecting anything when we shared photos. I am very photogenic with my smile and in terms of my appearance I am very fit, fashionable, and pretty, and confident too I know! I don’t share naked pictures or anything like that but I showed him some pics from weddings and other events where I wore really great outfits, but I wasn’t totally sure if he would like me because one never knows. For me, I was hoping for a picture of a real person and not a generic photo from who-knows-where, but the picture he showed me was a handsome face smiling at me, kind brown eyes, curly blondish hair and such a smooth looking jawline, he reminds me of a statue! His eyes are big and probing, even in photos, and I was very happy and a little bit suspicious at first! When we shared more photos, it looked really promising on my side but it was only when we finally did a video with his smile so magnetic that we really started to connect I think. I am petite and I love muscles and Nathan has a great body from working out with resistance training and stuff like that. I wasn’t sure what to expect, but I had so many big ideas and I know he did too because we told each other all about it so many times already late at night! Nothing needed to be said at that point because we knew! We both admitted a strange conceit to one another about how our lunch was just lunch and a chance to say hello, without expectations nor promises… haha I don’t know if it was obvious, still don’t, but I was very, very ready to be swept off my feet and in my vulnerable state Nathan would have to mess up pretty badly to not have his hands full with me!
I love to prepare, that’s what I do, and that morning was no different. I was so nervous and excited! I spent half the morning at the spa getting hair done, then a mani and a pedi. Then the other part of the morning was spent soaking in lavender bathwater and engaging in positive visualization ?. My whole body was soft and creamy and ready. I took forever getting going with my makeup and last minute fragrances! For my outfit I thought long and hard about it but I finally decided to wear the very same yellow jumper dress that he admired in one of my photos and nothing else, nothing at all…. He told me more than once that he loved how my legs looked and he preferred bare legs to stockings or even fishnets, so I wore that short dress and my legs were long, bare, and on display just for him! I didn’t wear a bra either and I knew he would notice that, because who wouldn’t. I hoped my nipples would show beneath the loose fabric of my jumper, and I hoped the feeling would keep me focused! After much, much deliberation I chose a pair of white call it spring pumps as the icing on Nathan’s little cake. I hoped he would like me.
I drove too quickly and arrived at the little café in his neighborhood too early. The place is located in a square and the whole area was fairly deserted despite a cool but sunny Saturday afternoon at that point. I debated waiting in my car but decided instead to sit out on the patio and wait for Nathan to hopefully not stand me up! I chose to leave my phone in my purse and to resist checking over-and-over for his inevitable text cancelling our date. Looking back now as I write this, I don’t know why I was so down and pessimistic, I guess, but I expected the worst pretty much every step of the way with Nathan and yet he continually proved me wrong. Doesn’t matter though, does it? I was pretty cool at that moment and I thought I would order one soy cap and if he didn’t show up by the time I finished, I’d ghost Nathan forever. But to my surprise and nervous delight Nathan showed up before the server even took my order!
I recognized Nathan even before he saw me from across the street since I was scanning to try to spot him. He told me he would wear a black leather jacket and, at first, I thought there might be a million people who would walk past looking just like that, but upon finally glimpsed him I immediately knew it was my Nathan! He looked the same, only three dimensional! As he approached, I squirmed in my chair and tried to be comfortable and pretty for the moment when he would see me for the first time. When he reached my side of the street, approaching the café, I crossed and re-crossed my legs and eased back into my chair. In my mind, I pretended to be aloof, not a care in the world, but my heart was racing and I suddenly felt very exposed and vulnerable. Then he saw me, and he smiled. I smiled back, and that was it.
I stood to greet him as Nathan climbed the wooden patio stairs, and when he took my hand I felt so small next to him. I blushed when he kissed the back of my hand, and then we both cracked up laughing somehow and the tension just melted away. We ordered our coffees and talked, but he kept remarking on how amazing he thought I looked and I was very amenable to his compliments! We weren’t even done our drinks before I was snuggling up closer to him on the bench and my fingernails scratched his jeans ever so softly. He kept smelling my hair. When I looked up at him, we stopped talking and he leaned in, taking a big risk. I rewarded him. I parted my lips and he kissed me very softly and tentatively for just a moment before his tongue darted out boldly to taste my lips. I licked his tongue right back and smiled as we kissed again, barely giggling. Nathan is a great kisser, patient but not slow, eager but not rushed, and we established a beautiful rhythm to our kiss that we had to break with a heavy sigh and guilty gaze…. our embrace only lasted for a moment but it sent me into a fluttery haze! My lips almost felt allergic to his touch, raw.
You’re such a good kisser, I cooed near his ear, still smiling, giving his lips another quick peck.
So are you, he somehow managed, barely above a grunt. I didn’t expect much conversation from Nathan from that point onward, but he’d surprise me yet again! Such a confident, handsome man! I could sense his nerves and uncertainty, but he never wavered and kept smiling. I knew that Nathan is the youngest of six brothers, so maybe he learned from the best! Either way, I was so relieved that I didn’t have to lead him or reassure him or anything, which is totally not what I’m used to! I was falling deeply, deeply in lust with my handsome Nathan on that cool May patio. Thinking back now, if the whole “alpha” thing is real then Nathan doesn’t really qualify because he isn’t aggressive or “dominant”, but he never seems *too* unsure, he can take a joke without becoming defensive, and he really knows how to listen and talk without making it a competition. I’m pointing all of this out now because I suppose I miss Nathan and it’s a special quality to find someone you can connect with on that level. Nathan is very confident, but it isn’t a performance for him any more than it is for me. I can spot that kind of thing immediately in a person and Nathan was absolutely melting me right there. I know that it is all just comfortable, friendly conversation, but somehow finding someone with whom I can do that reliably and consistently (i.e. for the rest of my days on this planet!) has been the hardest part of living life for me.
Okay, get on with it, Cindy, right? Right. I’m only getting a little nostalgic now I guess, so I’ll probably just edit out all that corny stuff later. Anyways, after our kiss, I looked into his eyes with as much eagerness as I could project and asked Nathan if we could go. Of course, suddenly he was in his feet like a marine. He rather awkwardly paid for our coffees with debit (when he’s more experienced with dating he’ll learn to leave a $20 on the table and rush me back to his cave!), so I just stood there for what seemed like forever just balancing in my heels while the server fumbled with receipts. Hurry up, Nathan! When everything was finally sorted out and everyone got their 15%, I took his arm and Nathan lead me to the sidewalk where we walked a few short blocks to his place. We didn’t say much, he just kept nervously insisting it was only a few seconds away, and suddenly we seemed somehow rushed and awkward. My heels clicked and almost seemed to echo the whole way and I felt so conspicuous even though nobody was around.
We reached his apartment fairly quickly, a second-floor walk-up right off the sidewalk of a busy street. He unlocked the door and held it open for me and I turned my hips slowly as I balanced my way up the stairs with Nathan close behind me, my skirt short but not so short as to reveal my little surprise. At the top, he unlocked another door and we were inside his warm, cramped, hideously carpeted apartment. The air was thick with Mr. Clean, a fragrance I know well, and it warmed my heart somehow to imagine Nathan scrambling to clean his bathroom on what he must have thought was the slight, infinitesimal chance that I’d go home with him. Yet there I was, in the middle of his living room clutching my heels in one hand, bare feet sinking into the carpet, and wondering how long until he would finally take me.
To my delight, Nathan held my hips from behind and began kissing my shoulders. I sighed and sank into his touch, running my fingers through his hair and arching my back into him. His hands ran along my sides up to my breasts and cupped them while I gripped him tight, holding on for dear life. His mouth was all over my left shoulder and my neck, kissing and tasting me, and I couldn’t help but moan his name over-and-over the whole time. He massaged my breasts and pinched both my nipples at the same moment, shocking my body and causing me to stand straight, as if on instinct. I gasped and turned to face him and fell into his chest as he took me in his arms. We kissed deeply and desperately, his hands all over me in a frenzy, as if he couldn’t contain himself.
I took a step back and unzipped the side of my dress, allowing it to tumble to the floor at my feet, revealing my soft, creamy naked body. He gazed upon me but his eyes did not cause any modesty in me—instead, I felt his joy. He finally smiled and looked into my eyes again, and it was a look of gratitude, somehow. I smiled back and shoved him hard, pushing him back onto the futon, where I perched on his lap and allowed him to explore my body. Nathan sucked hard on my nipples and I gasped again at his eagerness. Oh Nathan, I whimpered, trembling as his strong hands roamed my body, gripping my butt and finally holding me like that while we continued kissing and tasting one another. I felt his cock hardening through his jeans and I started grinding on him as best I could, but Nathan had a better idea and cupped my pussy in his palm so I could rock back and forth on it. Our eyes were locked as I bit my lip and rotated my hips in little circles. His bottom of his palm was pressed hard against me and his wrist was so strong I could grind on him like that and make myself cum if I tried. But I had other ideas.
I curled down into his lap and lowered myself to my knees, unbuttoning his shirt and running my fingernails all over his chiseled, sculpted chest. His muscles were young and powerful, so well defined—just like his jaw, almost like marble to the eye. To the touch, his body was hard but yielded to me under a soft, youthful shell that would one day harden with years of work and its ritual abuses. But Nathan was all energy and potential in my hands, young and eager to prove something to me I didn’t need proven. I kissed his chest, leaving soft marks of ruby lipstick as I descended, finally unzipping his jeans to reveal his thick, raging cock. I held him in my fingers and kissed along the shaft, eyes on him the whole time as he stared back at me awkwardly. I popped him into my mouth and before I knew it I was working him hard and really giving everything I had to pleasuring him. He smelled like baby powder. As I was blowing Nathan, he held the back of my head and finally seemed to be bracing himself as I took him deep with each bob of my head. I finally popped him out of my mouth and smacked his dick against my tongue, giving it another wet kiss.
Mmm, I love your dick baby.
Thanks, he managed. I tried not to laugh as I went back to work, sucking him until I was worried he would cum if I kept it up for much longer. I finally let him go and his cock flopped to his chest and I tongued his balls, scratching my fingernails on his thighs and teasing him even more. I was more than ready for sex and I didn’t want to wait, so I climbed back into his lap and sank right down on his cock in one motion. I had condoms with me in my purse but I forgot all about them at that moment, and when I did remember I didn’t care. Nathan felt so amazing inside me and it had been so long since I felt that way. He was so incredibly hard and straight, it felt like I was impaled on a tusk. I rocked my hips in little circles again as I adjusted to him, and in his eyes I could see surprise and even a little fear, even though his body seemed to betray those emotions. Nathan was more than ready for me, obviously. I started to ride him slowly and our rhythm increased every time we moaned. A few moments later I was bouncing on Nathan’s cock and riding him to a deep, satisfying orgasm that I rode out the whole way. When I finally came around, Nathan held my trembling body in his strong arms and I came down slowly and beautifully, as if floating on a cloud.
I kept rotating my hips as we kissed and I was ready to turn around and let Nathan take me from behind, but I felt him stiffening up right then and I made a decision. I sank down even deeper, my pussy tightening around him and he began to tremble. I bounced in his lap and held his shoulders, whispering in his ear: “Cum for me, baby. Please cum inside me…”
It didn’t take much coaxing for me to get what I wanted. Nathan stiffened up and released me from his grip, roaring as his cum exploded up inside me, so warm. I continued to rock back and forth and I could feel his dick spasming as he ejaculated pulse-after-pulse. I was so tight around him I felt every delicious pulse. Nathan held me in his arms again and we kissed as I felt our cum oozing out of me and down his thick shaft. It felt so wonderful to be with him, sharing that moment, all the pent-up frustrations and anticipations all released in one beautiful instant. We kissed and kissed. He sucked my breasts again and explored my body while we waited for his cock to soften, but it never did. Before long, I was riding him hard again and he seemed ready for much, much more.
So I slowed down and rolled my hips, keeping his cock barely inside me while I teased the head by almost popping him out of me. He groaned in a mix of agony and ecstasy. You’re still hard, baby, I cooed, my pussy gripping him tight again as if to prove it. He could only smile. I slipped off his cock and reached down, gripping it in my little fist, and I repositioned myself over him. I smiled and eased myself down as he gazed up in astonishment. We were so slick and sloppy from our cum that I managed to slip right down onto him in a grip still so tight Nathan grit his teeth the whole time. I fucked him like that, eyes locked, intense.
I love you in my ass, I whispered, increasing the pace. Nathan grunted agreement, trying to hold on. Fuck me, baby, fuck my ass, I moaned into his ear, and he was eager to do as he was told. I wondered if he would last for hours now, if I had properly drained him or if he had more. But it didn’t take long for me to feel him stiffening up again. My eyes were wide and I gazed down on him, grinding my ass on his cock and I prepared for him again. Cum again, Nathan, I whispered, cum in my ass, oh please cum in my ass, I want it. Nathan didn’t roar that time—he merely bit his lip and made what sounded like confused grunts. I felt his sperm flowing into me and I pushed down as far as his cock would let me, absorbing everything I could get. Nathan, spent and then some, could barely open his eyes when I climbed off him and hopped barefoot over to his bathroom. I used his brand-new box of tissues to catch our fluids before they spilled down my legs, and I suddenly regretting not wearing any underwear!
After we cleaned up, I hung around for a few minutes before I reminded him that I couldn’t stay. Nathan didn’t put up too much of a fight… he seemed like it would take a few months for him to get his strength back after I was done with him! So I left, and that was that.
Anyway, that was what happened with Nathan, pretty much. I won’t lie and pretend that we never got together again—we did, a few times– but it was never like that first time and I honestly doubt I will ever have such a hot and crazy experience like that again. That’s why I decided to write about it, so I can remember!
I hope that was okay to read. Thanks so much for your attention and I hope you have a happy, healthy, and safe spring!
Cindy xoxo
Source: reddit.com/r/gonewildstories/comments/flg26k/fm_about_the_time_i_had_sex_with_a_guy_i_met