My most adventurous few days [FM] [FM] (long)

Almost a year ago I wrote here about my first cheating experience:

[https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/](https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/)

The TL;DR is that then-37-year-old, petite, professional, married Asian Good Girl me hooked up with a grad student at a conference, and I was still feeling both excited and tremendously guilty about it. Quite a lot has changed in my life since then, and maybe I’ll write more about some of that later. But for now I want to reminisce about the wildest fling I had in my single days. It was also at a conference, but when I was myself a grad student, and part of what still gets me feeling frisky every time I attend one of these things, though after getting married I never acted on it. Until last year, of course.

I was a grad student, and at my first major conference while single. At 26, I had strayed from my UsuallyGoodGirl self barely at all; I had sexual experience, but (almost) only with serious boyfriends, and I was a pretty horny girl. I worried sometimes (at 26! How naïve!) that my prime sexual years would go by without really exploring. I told myself that I was free to leave UsuallyGoodGirl behind and get a little wild for this event, but I also set some ground rules. I wasn’t going to do anything unsafe, and I wasn’t going to do anything to make my roommate uncomfortable (we had to share hotel rooms; cheap department!). That meant that my own room was pretty much off limits. (Well, I could and did take care of myself in the shower, obviously, but nothing beyond that. And it turned out she wasn’t as innocent as I thought, anyway! But I didn’t know that yet. And no, don’t get excited, she’s not in this story.) The conference was spread out over a few nearby locations, but many of the events (keynote, parties, etc) were in the same hotel where I was staying.

This happened a long time ago and I’ve altered a few details for anonymity and filled in a few gaps in my memory, so I hope you’ll all forgive a little bit of embellishment.

**Day 1**

The evening of the first full day of the conference, there was a party/mixer just for grad students, with free booze. I was chatting with a couple of friends from my own university when I was approached by “Jorge,” a tall Spanish guy, about my age, with broad shoulders and a five o’clock shadow. Unquestionably hot, and he was hitting on me pretty hard from the get-go. So much so that my friends got the point and left us alone, after my roommate gave me the “you ok?” look and got what must have been a stupid excited grin in return. Jorge and I chatted for a while about the usual stupid stuff — where we were each from, what we studied, what we thought of the city we were in. I’m pretty sure I was engaged enough in the conversation, but I don’t remember any of the answers. I was just checking him out the entire time, and getting more and more horny.

He obviously noticed the attention, and finally, in the middle of small-talk, he outright asked if I wanted to come up to his room and “make love.” I practically spit out my drink. It was like something out of a cheesy movie where the sophisticated European guy picks up the naïve American and teaches her about romance. I am sure I giggled, but also, fuck it, yes, I did want to go upstairs with him. I told him I needed to make a quick stop first, so he gave me his room number. I found my roommate and let her know I might be late or absent; she got a little wide-eyed, but nodded. I went back to my own room first, cleaned myself up a little, and put together an overnight bag, then went to Jorge’s room.

We were making out like horny teenagers immediately. He was the tallest guy I’d ever made out with, and I’m pretty petite, so it was a new experience for me. But it turned out he wasn’t just naturally tall and broad-shouldered, he was *ripped*, and he had no problem picking me up so I could wrap my legs around him and kiss him, while I felt his cock pressing through his trousers against me. It was unbelievably hot. He was still holding me up like that when I unbuttoned his shirt, and then he set me down so I could run my hands through his chest hair and kiss his nipples. He was the first guy with a real six-pack I’d been with, and while I don’t really go for the gym-obsessed athletic type, from a purely animal point of view it really was exciting.

Jorge helped me pull my own dress off, then lifted me up again to lay me down on the bed. We made out like that, him hovering over me, while he rubbed my nipples with his thumbs, roughly, through my bra, and finally unclasped it. He started gently licking and sucking on my nipples. I had my eyes closed and was breathing pretty heavily, so I didn’t notice his hand reach down and very lightly brush between my legs, over my panties, and I think I cried out loud — I had not realized how much I was aching for it. My reaction emboldened him, and soon he reached his hand under the panties and was rubbing me, still gently, but faster and faster. By the time his big fingers made it to my clit, I was almost ready to cum, and I did so, loudly, while he was still sucking on my nipple.

He slowly worked down the rhythm with his fingers, then stood up and just looked at me, but just for a moment. before undoing his belt and taking off his trousers and underwear. I sat up to check out what he was packing. It was a bit longer than average for those I’d seen, average girth, and my first uncircumcised one. I reached out my hand and stroked it gently, and started to lean forward to kiss it, but he put his hand on my head and gently pushed me back. “No. I’m going to fuck you.” At least it wasn’t “make love” this time! I got up, got out a condom and lube from my overnight bag, and applied both, then lay down on the bed, and he climbed on top.

He worked his way into me slowly, but didn’t waste a lot of time before he was pounding pretty hard. Which was just what I wanted, but it also led to a weird kind of… almost out-of-body experience, like I was looking at what was happening from the outside. Jorge and I didn’t have any kind of deep connection, and unlike if we had been dating, neither of us was either trying to build one or trying to fool the other into thinking there was one. This was purely transactional. We both wanted to fuck. Even the pretty devoted fingering he’d been doing a few minutes earlier was just to get me ready so he could fuck me. And that was all fine. In fact, looking at it from the outside, this attractive guy wanting to do that to me — and then doing it to me, with great gusto — was hot, and I was enjoying it! But it was a new thing for me, that was engaging some of my mind to process even as the rest was turned totally to enjoying the moment.

After a few minutes of this, he came into the condom in me, and rolled off of me. We didn’t really talk about it; after a few minutes rest and clean-up, we were sitting up, drinking some cheap wine from the minibar and exchanging the same inane small talk we’d had earlier. After a while I was getting tired and wondering whether I’d spend the night there or get dressed and go back to my room, when he matter-of-factly asked if I was ready to go again. I was, and the second round was actually a lot hotter. This time I was on all fours on the bed, facing a mirror on the wall, watching the reflection as he took me doggy style. That’s always one of my favorite positions, but somehow seeing his large frame towering over me as he thrust made it even better. I think very few people like looking at their own naked body, and I’m no different, but in that moment it was *hot*, especially with my hair and makeup still mussed from the last round. Of all the things that happened over those few days, this is the moment that I fantasize about the most, even though it wasn’t the naughtiest thing that I did — the image in the mirror of my UsuallyGoodGirl-self being fucked like that really imprinted itself on me, like my own personalized porn. I didn’t cum from the sex itself, but after he finished, he reached around and used his fingers on me until I did. It was a gentle orgasm, but satisfying. I heard him get up to clean himself up, but then I fell asleep there before he got back.

I initiated the third round in the morning, when I woke up before him but found he had gotten hard again in his sleep. Impressive, really! I stroked it with my hand until he woke up, then pushed him gently until he rolled onto his back. I fetched another condom, and I climbed on top. This time I took care of myself with my fingers as I rode him slowly. After I had cum, he grabbed my waist with both hands and thrust upward into me at a faster pace until he finished, too.

When I made the walk of shame back to my room to shower and get ready for the day, I wasn’t sure if I’d see Jorge again. We did exchange numbers, and I had enjoyed the time and had no regrets, but part of me felt like it was something to leave in the past.

**Day 2(a)**

I met my next conquest almost immediately the next morning, though I didn’t know it right away. I got to my first session of the day a few minutes late, and ran into “Doug” while hurriedly grabbing coffee and one of those cheap bagels that form the universal conference breakfast. We were both a little embarrassed for walking in as the first speaker was being introduced and grabbed two seats at the back. We exchanged comments, occasionally snarky ones, through the session. We didn’t even get each other’s names until the first speaker was done, and didn’t have a real conversation until later. But he was typical young anglophile academic; average height, skinny-to-normal build, clean shaven, glasses, messy brown hair. The type that would probably wear tweed when he was older, but for now, neither stylish nor frumpy. Maybe a year or two younger than I was. (Most of this, of course, I only really took in later — in the morning, he was a colleague, not a conquest.)

We parted with a simple “nice to meet you” for the next session, but I ran into Doug again at lunch, and we sat together. It turned out he was both whip smart and pretty funny, whether in small talk or in academic jargon. It turned out we would be attending another session together in the afternoon, and he very sweetly asked if I wanted to have dinner with him afterward, so it was a date!

We went to dinner at a not-fancy-but-nice-enough-by-grad-student-standards French restaurant not too far from the cluster of hotels where the conference was centered, and it was actually pretty great. We really hit it off. Under different circumstances, we might have dated long term. But knowing that wasn’t likely made the evening even better, knowing we could just have a fun date without worrying about the future.

After dinner, we decided to go to the hotel bar at one of the *other* hotels, not the one where we (and most of our friends) were staying, just to avoid gossip. But as we were walking there, a wave of naughtiness hit me. I was thinking about the fact that if I wanted to, I was probably going to have sex with this guy. I had never done anything with two guys in the same day before, and that was a lot for this UsuallyGoodGirl to process! Suddenly my feelings about Doug were rapidly shifting from “fun crush” mode to “horny” mode, and I wanted something to happen NOW — and I had an idea. So when we got to the hotel, instead of going to the bar, I grabbed his hand and led him up the stairs to the second floor, where all the conference rooms were. I knew the sessions were long ended by then, and figured, correctly, that the janitorial/service staff would be finished too. I led him silently, but it wasn’t hard to guess what I was doing, and we were practically kissing each other before we’d even gotten into the dark room.

As we made out, I did the math in my head. Doug was a fantastic kisser, but I wasn’t going to be satisfied with that. My condoms were back in my room. That left… sitting down in one of the front row chairs, unbuckling his belt and dropping his pants and underwear, and going down on him, which is exactly what I did. It happened so quickly as to startle him, but I ignored his “are you sure” protests and went right to it, and before long he was moaning my name. I had my left hand on his now-bare ass, and my right went back and forth between reaching up under his shirt to stroke his chest, and stroking the base of his cock, while I did the best I could on him with my tongue and lips. I dare say I knew what I was doing. My *count* for how many guys I had done this to was not that high, but I had plenty of experience on those few. By the time I could feel him getting close — which couldn’t have been more than a few minutes — my pussy was aching for more, but my head was just straight enough to know there wasn’t much more I could do right here, so I focused on finishing him off. And finish he did, with several strong spurts into my mouth. I kept sucking until I knew he was really done (I’ve had my clothes, or the guy’s, dribbled on after I thought I had everything before), milked him as clean as I could, and stood up and smiled at him before swallowing. I suspect that move didn’t come off as sexy as I‘d hoped in the dark, but *I* felt like a champion slut, and I loved it.

Doug pulled up his pants and stumbled into a chair before he collapsed. He was breathing hard and muttering under his breath, and when I could finally get him to look at me full on, all he could say for a minute was “Wow” with a shit-eating grin. He seemed to almost feel guilty about it, but I assured him I had wanted to do it and really enjoyed it, which was true!

After he had regained his composure, we decided to skip the drink and head back to his room. He asked me to give him a few minutes — I’m guessing his hotel room already had the messy bachelor look — and that, of course, he’d need some recharge time. I told him I wanted to stop by my own room to clean up and gather some things anyway, so we agreed to meet in an hour.

**Day 2(b)**

As I was heading back to my room, I got a text from Jorge, asking if I wanted to meet up again. (It was the kind of text that a few years later would probably have just been an eggplant emoji and a question mark.) I was about to text back an apology when my “you’re allowed to be wild” instincts kicked in again. I had already been with two guys in the same day, but this was my chance to have two in the same *hour*. It was like somebody else had taken control of my hands to text back “15min”. I rushed to my room, cleaned myself up a bit, and put my overnight bag back together, and hurried down to Jorge’s room.

Jorge was waiting for me with two glasses of champagne. I didn’t hide anything from him. I told him I didn’t have much time because I had another date. I suspected he wouldn’t be offended by this, and he wasn’t. In fact, he told me he was glad that my beautiful body would be enjoyed the way it should. I found that a little demeaning and a little flattering at the same time. I told him about what I’d already done with Doug, and for the first time he seemed jealous. He told me he was sorry he hadn’t gotten to experience my oral skills, and asked if I would give him a blowjob too.

I got onto my knees in front of him as he dropped his trousers and got started. The second cock in my mouth in less than an hour! As I started sucking him, Jorge was talking dirty to me, calling me a filthy slut who was going to suck his cock and drink his cum just like I had with another guy I had just met. In the moment that was a turn-on, but in fact the blowjob was nothing like the last one. With Doug I had been completely in control, but here, after a minute with my tongue and to get him fully hard, Jorge was just flat-out fucking my face. Not too hard or too deep for me to handle, but basically his hands gently on the sides of my head, pulling me toward him with each gentle thrust. My lips were basically a fuck toy for him. Just as the day before, it was hot to be used so matter-of-factly like this. He told me when he was getting close, and I reached up and tickled the underside of his balls and formed a tight seal around the head with my lips as he started to spurt into my mouth. Unsurprisingly, there wasn’t a whole lot of volume of cum after the several rounds he’d already done in the last 24 hours, but he still seemed to be pretty satisfied. I released his cock and let it slide out, trailing a tiny bit of his stuff onto my chin, and made sure he saw it before licking what I could and dabbing the rest with a tissue. We toasted with the champagne, which I had barely started before, and I swizzled a bit around my mouth before draining the glass. He told me he hoped the rest of my evening was “very satisfying”, and I took my bag and headed down to Doug’s room. It was about an hour and a quarter from when we had parted.

On the walk and elevator ride up to Doug’s room, I had my first pangs of — shame? guilt? — over what I was doing. Some of it was my UsuallyGoodGirl self peeking back through. Girls like me don’t do things like this! I was literally going back and forth between two men for sex! I had only once before ever done *any* sex act before the third date, and now I had given blowjobs to two men, fucked one of them and was on my way to fuck the other, who I had just met. And some of it was a feeling of guilt that I was somehow cheating on Doug, though not on Jorge. Jorge knew exactly what was happening, and there were no feelings there besides lust. But I actually felt a connection with Doug. I doubt I would have wanted to try for a long-term relationship anyway, but that wasn’t out of the question, and it was like I was cheating with him *in the middle of our first date*, which seemed about as low as I could go.

But it didn’t stop me, and I never told Doug. When I got to his room, things were basically right where we’d left off, which of course to him they basically were. After some more pretty hot makeout, he undressed me, started kissing me all over, and then pushed me down on the bed to go down on me. I always appreciate that, and he went at it with great gusto. But while it did feel good, somehow I didn’t feel the buildup I usually get when something is going to make me cum. I tried guiding him through the things I usually like, and he wasn’t doing anything wrong. I just wasn’t feeling it, probably because of the guilt/shame that was still hanging over me. I didn’t want to cut things short, though, so I finally pulled him up gently with my hands and said “I want you inside me.” Which was true enough.

He asked if I was sure I wanted him to stop with the oral. What a gentleman! But he was clearly also eager to move on to the next stage. He took off his own clothes, giving me the first good look at his dick, since we’d been in the dark when I had blown him earlier. It was a little shorter but a little thicker than Jorge’s — and another wave of guilt hit me when I automatically made that comparison in my head, but how could I not? — and already mostly erect when I gave it a gentle stroke. To my surprise, he didn’t climb on top of me, but instead lifted me up and took me to the side of the room; I hadn’t even noticed that his room, on a higher floor than mine, had a small balcony. I was apprehensive at first when he turned out the room lights and started to open the curtain, but I realized that the only way anybody would really see what they were doing would be with binoculars from the next building. He had slippers for us both, and had already set a condom out on the table on the balcony. I admired his presumption, and told him so. I did grab lube from my bag, and returned to him putting on the condom. I lubed it and myself up.

Although I hadn’t cum from the oral attention, I had gotten plenty wet and ready. So when he bent me over the balcony railing and took me from behind, he didn’t have any trouble sliding in. Pretty soon I was gripping the railing hard, trying to keep my eyes open to take in the fact that I had an amazing view of the city while I was getting fucked from behind. At the beginning, he was reaching around to finger me or rub my nipples, but eventually he had both hands gripped hard on my waist to thrust harder.

A strange thing happened during that session, something that never happened to me before or since. It felt really good to be fucked like that, but as with the oral before, I wasn’t feeling a build-up to orgasm. But suddenly, with only a second or two of warning, I felt my whole body tense up and then shudder, hard, involving just about every muscle in my body. I was briefly afraid I was going to lose control and pee myself or something, but fortunately not. I did feel my knees buckly, and I fell forward — more like I threw myself forward involuntarily, really — and off of Doug’s cock. It was probably the most intense orgasm I’d ever had, but not really in a good way. It felt fine, but it wasn’t *euphoric* in the way an orgasm usually is. There was just a hint of that, but it was totally dominated by the *release* aspect of an orgasm, like my body was shedding all kinds of energy that I didn’t even know had built up. It wasn’t a wave of pleasure as much as a wave of relief.

I’ve come up with lots of explanations for why it happened like that. Was this my mind’s way of trying to shed the shame and guilt over what I’d been doing so I could relax and enjoy things? Maybe it was a way of ridding bad emotions through physical exertion, like when somebody goes running or punches a punching bag to release anger. Maybe it was a regular orgasm, but my mind was punishing me for the way I’d achieved it. Probably none of these explanations make sense. But whatever it was, the release did clear a big mental roadblock for me, and while the shame wasn’t gone, it didn’t get in my way for the rest of the trip.

I did feel bad about the circumstances here, though, once I had composed myself. It turned out that Doug was cumming at basically the same time I was. Ordinarily, simultaneous orgasm is a moment for a really deep emotional connection with deep kissing and staring into each other’s eyes, or, depending on the circumstances, maybe a congratulatory high-five. (After I had made a big deal about one with an ex in the past, he had responded with “achievement unlocked,” which was perfect really.) Having it happen *the first time we have sex* might have led me to want to immediately marry this guy and run off somewhere to do nothing except hump like rabbits all day. In this case, though, I had apparently clenched down hard on Doug’s cock and then slid off of him just as he started to cum, leaving him just hanging out there in the night air while spurting into the condom, as he caught me from collapsing completely on the balcony and tried to make sure I was ok. Between that and my own joyless orgasm, it was a pretty poor example of what should have been an incredible shared experience.

It was also pretty funny, though, thinking of his poor cock wanting to unload into me and getting that instead. After a couple minutes to recover, we were both laughing about it. Still, I wanted to make it up to him at least a little. I led him to the bathroom, removed the condom, and took him to the shower to clean him up. Normally I won’t do oral after condom-sex, since I hate the taste of latex and I don’t want to inflict it on anybody else, either, but I made an exception here. I licked his stuff off of his now semi-erect cock and milked everything I could out of the tip, then tried to scrub him as clean as I could with a warm wet washcloth. Since we were there and naked, we decided to go ahead and shower there together. It was the first time I’d gotten to really explore his body, and he knew how to handle mine. After we’d gotten each other pretty clean, he started sucking on my nipples, which hadn’t gotten much attention throughout, and which started getting me worked up again. As he concentrated on my chest, I detached the shower head and started using the warm water and my fingers on my crotch. We didn’t have sex again that night, but I did get myself off with his help — a nice, normal, pleasurable, emotional orgasm this time. I offered to do more for him, too, but he said he thought it would be better in the morning. We dried each other off and fell asleep naked together.

I woke up the next morning to Doug reaching around to finger me as his cock pressed up against my ass. Once I stirred, he asked if he could go down on me again. I think he felt self conscious about not getting me off on his previous attempt. This time, I was relaxed, and not weighed down by guilt. The build-up was slow, but Doug was persistent and listened to my directions, and eventually brought me to a glorious orgasm.

When he climbed up to see me face-to-face, my own wetness was still on Doug’s chin, which really brought home for me both how much he wanted me and how much he wanted to please me. We kissed passionately until I felt him pressing up against me, and I had to gently remind him “Condom.” He put one on, entered me missionary position, and started thrusting. Throughout this session, he would alternate between kissing and lifting himself up onto his elbows to stare me in the eyes. This was the real “lovemaking” of the weekend. When he was getting close, he lifted my legs up so he could go deeper, then held deep and kissed me as he came. He kept kissing me for a moment after he’d finished, then rolled over next to me.

We lay in silent bliss for a bit, and then talked about how we felt. We were both honest about feeling a real connection, and that we wished we were closer. I suspect Doug might have wanted to try a long-distance relationship. I would have been reluctant to do that anyway, but especially given the way our physical relationship had started, I know I wouldn’t have been able to live with myself. We had already exchanged contact info, and agreed to keep in touch. I got dressed and headed back to my room to clean up and change clothes before the last session of the conference.

**Aftermath**

I saw Doug a few more times. All but one of these were at other conferences, and after I’d started dating my now-husband, so nothing happened there. But once was when I was on vacation with my family near his area, and I did manage to split off and see him, and there were more sparks. But that was the last time.

I said a quick hello to Jorge when I ran into him at the last day of the conference, but that was the last time I ever saw him.

After that weekend, I was mostly back to my UsuallyGoodGirl self. I eased up my standards about how fast I would move with a guy a bit, but there was nothing else particularly adventurous until my encounter with Mark last year.

Source: reddit.com/r/gonewildstories/comments/diam1e/my_most_adventurous_few_days_fm_fm_long